3850:
3805:
81:
8505:
91:
2332:
1489:
1466:
1438:
541:
332:
3822:
61:
2338:
51:
4324:
4364:
1009:
4369:
4344:
1014:
9734:
1093:
2567:
8487:
1089:
9698:
2022:
2679:
107:
3783:
3879:
8496:
9722:
9710:
10673:
1357:
3135:, first described in 1949 by Otto Hromatka and Heinrich Ebner. In this method, alcohol is fermented to vinegar in a continuously stirred tank, and oxygen is supplied by bubbling air through the solution. Using modern applications of this method, vinegar of 15% acetic acid can be prepared in only 24 hours in batch process, even 20% in 60-hour fed-batch process.
3112:. As the demand for vinegar for culinary, medical, and sanitary purposes increased, vintners quickly learned to use other organic materials to produce vinegar in the hot summer months before the grapes were ripe and ready for processing into wine. This method was slow, however, and not always successful, as the vintners did not understand the process.
1094:
4258:
Prolonged inhalation exposure (eight hours) to acetic acid vapours at 10 ppm can produce some irritation of eyes, nose, and throat; at 100 ppm marked lung irritation and possible damage to lungs, eyes, and skin may result. Vapour concentrations of 1,000 ppm cause marked irritation of eyes, nose and
2617:
out. As of 2003–2005, total worldwide production of virgin acetic acid was estimated at 5 Mt/a (million tonnes per year), approximately half of which was produced in the United States. European production was approximately 1 Mt/a and declining, while
Japanese production was 0.7 Mt/a.
1781:
name "Eisessig" ("ice vinegar"), the name comes from the solid ice-like crystals that form with agitation, slightly below room temperature at 16.6 °C (61.9 °F). Acetic acid can never be truly water-free in an atmosphere that contains water, so the presence of 0.1% water in glacial acetic
4271:
and irritation of the eyes, nose, and throat, with pharyngeal oedema and chronic bronchitis. Unacclimatised humans experience extreme eye and nasal irritation at concentrations in excess of 25 ppm, and conjunctivitis from concentrations below 10 ppm has been reported. In a study of five workers
4266:
In 12 workers exposed for two or more years to an airborne average concentration of 51 ppm acetic acid (estimated), symptoms of conjunctive irritation, upper respiratory tract irritation, and hyperkeratotic dermatitis were produced. Exposure to 50 ppm or more is intolerable to most persons and
3756:
of vegetables and other foods. Table vinegar tends to be more diluted (4% to 8% acetic acid), while commercial food pickling employs solutions that are more concentrated. The proportion of acetic acid used worldwide as vinegar is not as large as industrial uses, but it is by far the oldest and
3516:
with alcohol, which are then esterified with acetic acid. The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA, more commonly known as PGMEA in semiconductor manufacturing
2241:
4272:
exposed for seven to 12 years to concentrations of 80 to 200 ppm at peaks, the principal findings were blackening and hyperkeratosis of the skin of the hands, conjunctivitis (but no corneal damage), bronchitis and pharyngitis, and erosion of the exposed teeth (incisors and canines).
1092:
3714:
Acetic acid is an effective antiseptic when used as a 1% solution, with broad spectrum of activity against streptococci, staphylococci, pseudomonas, enterococci and others. It may be used to treat skin infections caused by pseudomonas strains resistant to typical antibiotics.
1645:
is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC. Acetic acid is also known as acetyl hydroxide (AcOH).
4386:
Concentrated acetic acid can be ignited only with difficulty at standard temperature and pressure, but becomes a flammable risk in temperatures greater than 39 °C (102 °F), and can form explosive mixtures with air at higher temperatures with
2586:, explained below. The biological route accounts for only about 10% of world production, but it remains important for the production of vinegar because many food purity laws require vinegar used in foods to be of biological origin. Other processes are
2618:
Another 1.5 Mt were recycled each year, bringing the total world market to 6.5 Mt/a. Since then, the global production has increased from 10.7 Mt/a in 2010 to 17.88 Mt/a in 2023. The two biggest producers of virgin acetic acid are
2883:. These side-products are also commercially valuable, and the reaction conditions may be altered to produce more of them where needed. However, the separation of acetic acid from these by-products adds to the cost of the process.
2014:. The presence of water in vinegar has such a profound effect on acetic acid's properties that for centuries chemists believed that glacial acetic acid and the acid found in vinegar were two different substances. French chemist
2364:
can be detected. Dimers also occur in the liquid phase in dilute solutions with non-hydrogen-bonding solvents, and to a certain extent in pure acetic acid, but are disrupted by hydrogen-bonding solvents. The dissociation
4288:) solution, with the most significant increases in hazard levels at thresholds of 25% and 90% acetic acid concentration by weight. The following table summarizes the hazards of acetic acid solutions by concentration:
1110:
3747:
Acetic acid has 349 kcal (1,460 kJ) per 100 g. Vinegar is typically no less than 4% acetic acid by mass. Legal limits on acetic acid content vary by jurisdiction. Vinegar is used directly as a
3533:. The worldwide production of acetic anhydride is a major application, and uses approximately 25% to 30% of the global production of acetic acid. The main process involves dehydration of acetic acid to give
3517:
processes, where it is used as a resist solvent). This application consumes about 15% to 20% of worldwide acetic acid. Ether acetates, for example EEA, have been shown to be harmful to human reproduction.
3115:
One of the first modern commercial processes was the "fast method" or "German method", first practised in
Germany in 1823. In this process, fermentation takes place in a tower packed with wood shavings or
1022:
2866:
and pressures designed to be as hot as possible while still keeping the butane a liquid. Typical reaction conditions are 150 °C (302 °F) and 55 atm. Side-products may also form, including
2369:
of the dimer is estimated at 65.0–66.0 kJ/mol, and the dissociation entropy at 154–157 J mol K. Other carboxylic acids engage in similar intermolecular hydrogen bonding interactions.
4432:
Acetic acid that is manufactured by intent, rather than recovered from processing (such as the production of cellulose acetates, polyvinyl alcohol operations, and numerous acetic anhydride acylations).
7904:
5910:
7898:
6861:
989:
5777:
Sim JH, Kamaruddin AH, Long WS, Najafpour G (2007). "Clostridium aceticum—A potential organism in catalyzing carbon monoxide to acetic acid: Application of response surface methodology".
7844:
2232:; in all previous ISM molecular discoveries made in the millimetre and centimetre wavelength regimes, single dish radio telescopes were at least partly responsible for the detections.
3231:
to metabolize sugars directly, or to produce acetic acid from less costly inputs, suggests that these bacteria could produce acetic acid more efficiently than ethanol-oxidizers like
973:
7969:
7957:
7838:
7832:
7868:
6834:
3031:
have made acetic acid, in the form of vinegar. Given sufficient oxygen, these bacteria can produce vinegar from a variety of alcoholic foodstuffs. Commonly used feeds include
6677:
2783:. This remains the second-most-important manufacturing method, although it is usually not competitive with the carbonylation of methanol. The acetaldehyde can be produced by
8107:
7963:
6109:
Ryssel H, Kloeters O, Germann G, Schäfer T, Wiedemann G, Oehlbauer M (August 2009). "The antimicrobial effect of acetic acid--an alternative to common local antiseptics?".
6005:"Performance of alternative strategies for primary cervical cancer screening in sub-Saharan Africa: systematic review and meta-analysis of diagnostic test accuracy studies"
7826:
3159:, can convert sugars to acetic acid directly without creating ethanol as an intermediate. The overall chemical reaction conducted by these bacteria may be represented as:
6486:
Duan X, Page M (1995). "Theoretical
Investigation of Competing Mechanisms in the Thermal Unimolecular Decomposition of Acetic Acid and the Hydration Reaction of Ketene".
9047:
8817:
8777:
8269:
6854:
4284:
to skin. These burns or blisters may not appear until hours after exposure. The hazardous properties of acetic acid are dependent on the concentration of the (typically
3089:
and kept in a warm, airy place will become vinegar over the course of a few months. Industrial vinegar-making methods accelerate this process by improving the supply of
1064:
2760:
and more efficient and has largely supplanted the former process. Catalytic amounts of water are used in both processes, but the Cativa process requires less, so the
2117:
developed a methanol carbonylation pilot plant as early as 1925. However, a lack of practical materials that could contain the corrosive reaction mixture at the high
1095:
8978:
8953:
8943:
8160:
7814:
7765:
7759:
1732:. Its production and subsequent industrial use poses health hazards to workers, including incidental skin damage and chronic respiratory injuries from inhalation.
3674:
Glacial acetic acid is used in analytical chemistry for the estimation of weakly alkaline substances such as organic amides. Glacial acetic acid is a much weaker
10591:
7820:
3678:
than water, so the amide behaves as a strong base in this medium. It then can be titrated using a solution in glacial acetic acid of a very strong acid, such as
2327:
of 2.4, indicating that merely 0.4% of the acetic acid molecules are dissociated. Only in very dilute (< 10 M) solution, acetic acid is >90% dissociated.
10743:
9349:
8677:
8618:
8526:
8034:
7994:
7988:
7929:
7802:
6847:
5641:
Misono M (2009). "Recent progress in the practical applications of heteropolyacid and perovskite catalysts: Catalytic technology for the sustainable society".
10599:
10274:
9882:
9438:
9254:
9189:
9129:
9057:
8963:
8857:
8727:
8682:
8353:
8223:
8215:
8196:
8177:
7771:
4568:
4546:
1213:
928:
9518:
10345:
8983:
8827:
8797:
7915:
3259:
and concentrating it. As a result, although acetogenic bacteria have been known since 1940, their industrial use is confined to a few niche applications.
2157:
built the first plant using this catalyst in 1970, and rhodium-catalyzed methanol carbonylation became the dominant method of acetic acid production (see
80:
10270:
8913:
8893:
8566:
8235:
7808:
2643:
8938:
1370:
6521:
6054:"Efficacy of 1% acetic acid in the treatment of chronic wounds infected with Pseudomonas aeruginosa: prospective randomised controlled clinical trial"
10124:
10109:
10009:
9836:
7796:
7790:
5847:
5809:
5512:
5459:
5160:
8576:
8278:
8933:
8262:
5031:
Briggs JM, Nguyen TB, Jorgensen WL (1991). "Monte Carlo simulations of liquid acetic acid and methyl acetate with the OPLS potential functions".
4736:
1117:
6828:
10748:
8603:
3017:
It is thought to be competitive with methanol carbonylation for smaller plants (100–250 kt/a), depending on the local price of ethylene.
9149:
8546:
3287:
monomer (VAM). In 2008, this application was estimated to consume a third of the world's production of acetic acid. The reaction consists of
1402:
8697:
580:
8608:
5383:
Yoneda N, Kusano S, Yasui M, Pujado P, Wilcher S (2001). "Recent advances in processes and catalysts for the production of acetic acid".
6805:
4769:
3911:. Reduction of acetic acid gives ethanol. The OH group is the main site of reaction, as illustrated by the conversion of acetic acid to
8255:
6813:
6717:
5731:
Partridge EP (1931). "Acetic Acid and
Cellulose Acetate in the United States A General Survey of Economic and Technical Developments".
2331:
9476:
8792:
6644:
6686:
6371:
5510:
Zoeller JR, Agreda VH, Cook SL, Lafferty NL, Polichnowski SW, Pond DM (1992). "Eastman
Chemical Company Acetic Anhydride Process".
5420:
5758:
Hromatka O, Ebner H (1949). "Investigations on vinegar fermentation: Generator for vinegar fermentation and aeration procedures".
3251:
strains that can produce vinegar in concentrations up to 20%. At present, it remains more cost-effective to produce vinegar using
2503:(glycerine triacetate) is a common food additive and is found in cosmetics and topical medicines; this additive is metabolized to
6601:
Brantley LR, Cromwell TM, Mead JF (1947). "Detection of acetate ion by the reaction with arsenious oxide to form cacodyl oxide".
3849:
5476:
3804:
9008:
8767:
8687:
6801:
6742:
3275:, closely followed by acetic anhydride and ester production. The volume of acetic acid used in vinegar is comparatively small.
2205:
896:
7520:
7301:
6769:
6270:
5893:
5685:
5575:
5364:
5204:
5114:
4931:
4870:
4674:
4628:
4603:
4494:
3730:
2975:, Japan, in 1997, commercialised a cheaper single-stage conversion of ethylene to acetic acid. The process is catalyzed by a
869:
395:
90:
9389:
6809:
2125:
or more) discouraged commercialization of these routes. The first commercial methanol carbonylation process, which used a
4245:
Amounts of acetic acid used in these other applications together account for another 5–10% of acetic acid use worldwide.
6405:
2228:
source). Acetic acid has the distinction of being the first molecule discovered in the interstellar medium using solely
1845:
of acetic acid. (The symbol Ac for the acetyl functional group is not to be confused with the symbol Ac for the element
9771:
9641:
5864:
5826:
5177:
1849:; context prevents confusion among organic chemists). To better reflect its structure, acetic acid is often written as
1365:
3271:
for the production of chemical compounds. The largest single use of acetic acid is in the production of vinyl acetate
60:
10179:
9541:
6355:
555:
5598:
Sano K, Uchida H, Wakabayashi S (1999). "A new process for acetic acid production by direct oxidation of ethylene".
1103:
6789:
2928:
Using modern catalysts, this reaction can have an acetic acid yield greater than 95%. The major side-products are
2153:) was discovered that could operate efficiently at lower pressure with almost no by-products. US chemical company
1377:
50:
10733:
9666:
4980:
958:
4582:
2542:, and acetic acid is produced naturally as fruits and other foods spoil. Acetic acid is also a component of the
106:
6389:"Departmental Consolidation of the Food and Drugs Act and the Food and Drug Regulations – Part B – Division 19"
5058:
Togeas JB (June 2005). "Acetic acid vapor: 2. A statistical mechanical critique of vapor density experiments".
4837:
4117:
solution, which results in a deeply red colour that disappears after acidification. A more sensitive test uses
2433:
properties of acetic acid make it a useful industrial chemical, for example, as a solvent in the production of
2217:
2429:
at all compositions, and solubility of acetic acid in alkanes declines with longer n-alkanes. The solvent and
2409:, but also non-polar compounds such as oils as well as polar solutes. It is miscible with polar and non-polar
2109:
are commodity raw materials, methanol carbonylation long appeared to be attractive precursors to acetic acid.
1889:, the abbreviation HAc is sometimes used, where Ac in this case is a symbol for acetate (rather than acetyl).
9591:
5888:. RSC Paperbacks Series. Vol. 38 (2nd ed.). Great Britain: Royal Society of Chemistry. p. 80.
3652:
3621:
131:
10723:
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9626:
2402:
1484:
1054:
488:
327:
5456:
439:
10713:
8822:
5911:"Determination of Water Content in Perchloric acid 0,1 mol/L in acetic acid Using Karl Fischer Titration"
5222:"Reversible lysine acetylation controls the activity of the mitochondrial enzyme acetyl-CoA synthetase 2"
5132:
Bulletin de l'Académie
Polonaise des Sciences, Série des Sciences Chimiques, Géologiques et Géographiques
3644:
2575:
2209:
1752:
name, is constructed according to the substitutive nomenclature. The name "acetic acid" derives from the
1445:
519:
17:
6003:
Fokom-Domgue J, Combescure C, Fokom-Defo V, Tebeu PM, Vassilakos P, Kengne AP, et al. (July 2015).
5668:
Chotani GK, Gaertner AL, Arbige MV, Dodge TC (2007). "Industrial
Biotechnology: Discovery to Delivery".
4067:
are also used for this purpose. Metal acetates can also be prepared from acetic acid and an appropriate
1060:
10663:
4478:
4323:
3633:
2526:
2297:
1237:
1224:
729:
8040:
6839:
4751:
2779:
Prior to the commercialization of the
Monsanto process, most acetic acid was produced by oxidation of
2229:
269:
10753:
10495:
9581:
9576:
8757:
7513:
7294:
6314:
6286:
4141:
Organic or inorganic salts are produced from acetic acid. Some commercially significant derivatives:
3831:
3700:
3691:
2614:
339:
2459:, formally derived from acetic acid, is fundamental to all forms of life. Typically, it is bound to
9621:
5539:
Hintermann L, Labonne A (2007). "Catalytic
Hydration of Alkynes and Its Application in Synthesis".
4475:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
4206:
Halogenated acetic acids are produced from acetic acid. Some commercially significant derivatives:
2761:
2639:
1461:
1140:
536:
433:
10546:
9919:
9824:
9701:
7753:
7337:
7262:
4400:
4052:
3132:
2011:
1501:
1339:
760:
4363:
3128:. The improved air supply in this process cut the time to prepare vinegar from months to weeks.
2405:(dielectric constant) of 6.2, it dissolves not only polar compounds such as inorganic salts and
1008:
209:
191:
10698:
10578:
10191:
10168:
10039:
9764:
9556:
8521:
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8303:
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4702:
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3932:
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2434:
2068:
1886:
845:
9749:
6819:
6560:
6260:
4862:
4855:
4368:
4343:
3939:
can be formed. When heated above 440 °C (824 °F), acetic acid decomposes to produce
2257:(−COOH) in carboxylic acids such as acetic acid can separate from the molecule by ionization:
1926:
to air because acetic acid-producing bacteria are present globally. The use of acetic acid in
1013:
10693:
10522:
10514:
10368:
10303:
10255:
10211:
10157:
10032:
10024:
9939:
9931:
9611:
9586:
9224:
8842:
8389:
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7874:
7747:
7052:
5881:
4797:
4304:
4195:
3924:
3526:
3121:
2895:
2464:
2225:
2041:
1036:
1001:
696:
7941:
7935:
10728:
10703:
10570:
10391:
10329:
10017:
10001:
9912:
9843:
9672:
9656:
9281:
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8504:
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8016:
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7342:
7287:
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6774:
6610:
5673:
5492:
5067:
4995:
4946:
4902:
4824:
4234:
4214:
3537:
at 700–750 °C. Ketene is thereafter reacted with acetic acid to obtain the anhydride:
2648:
2627:
2515:
2061:
2049:
1790:
1745:
497:
119:
6703:
6651:
5478:
Acetic Acid Market Size & Share Analysis - Growth Trends & Forecasts (2023 - 2028)
3903:. With strong bases (e.g., organolithium reagents), it can be doubly deprotonated to give
2356:
In solid acetic acid, the molecules form chains of individual molecules interconnected by
8:
10562:
10487:
10356:
10199:
9968:
9923:
9616:
9596:
9409:
9099:
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8451:
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8313:
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3405:
2984:
2606:
2543:
2201:
2057:
289:
157:
7862:
7850:
6784:
6614:
6522:"Corrosion by Acetic Acid—A Report of Task Group T-5A-3 On Corrosion by Acetic Acid (1)"
5677:
5428:
5071:
4999:
4950:
4906:
2193:, and has largely supplanted the Monsanto process, often in the same production plants.
2078:, a product of the distillation of wood. The acetic acid was isolated by treatment with
1677:, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in
249:
167:
10530:
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10070:
10062:
9714:
9636:
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9551:
9428:
9404:
8903:
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8513:
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6424:
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4228:
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4114:
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3144:
2631:
2037:
2033:
1983:
1957:
1786:
1488:
1465:
540:
331:
229:
5396:
3096:
The first batches of vinegar produced by fermentation probably followed errors in the
2972:
1437:
10738:
10503:
10479:
10337:
10139:
10078:
10054:
9978:
9904:
9817:
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6823:
6626:
6541:
6503:
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6210:
Page MJ, Green S, Mrocki MA, Surace SJ, Deitch J, McBain B, et al. (June 2016).
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Scientific literature reviews on generally recognised as safe (GRAS) food ingredients
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3593:
3341:
2799:
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Two related processes exist for the carbonylation of methanol: the rhodium-catalyzed
2361:
2204:
acetic acid was discovered in 1996 by a team led by David Mehringer using the former
2122:
2075:
1690:
1670:
1666:
1662:
1319:
1303:
8247:
5790:
5627:
3821:
2987:. A similar process uses the same metal catalyst on silicotungstic acid and silica:
10718:
10383:
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10047:
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9855:
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5003:
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2213:
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2154:
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2007:
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1973:
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and industrial chemical across various fields, used primarily in the production of
1589:
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1549:
1514:
1412:
1299:
1068:
949:
939:
773:
683:
603:
6685:. Virginia Department of Health Division of Health Hazards Control. Archived from
5169:
4962:
4059:, aluminium tanks are used to transport acetic acid. Containers lined with glass,
3696:
Acetic acid injection into a tumor has been used to treat cancer since the 1800s.
3247:
strains can produce vinegar in concentrations of only a few per cent, compared to
10677:
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10538:
10287:
10247:
10240:
10224:
10149:
10098:
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4388:
4259:
upper respiratory tract and cannot be tolerated. These predictions were based on
4213:(monochloroacetic acid, MCA), dichloroacetic acid (considered a by-product), and
4110:
4060:
4056:
3912:
3775:
3679:
3513:
3501:
3190:
2980:
2841:
2757:
2670:
2337:
2293:
2190:
2106:
2083:
1778:
1678:
1650:
1327:
1307:
1269:
1153:
809:
373:
6577:
6144:
6122:
5973:
Yamamoto S, Iguchi Y, Shibata N, Takesue M, Tsunoda T, Sato K (April 1998). "".
5845:
Held H, Rengstl A, Mayer D. "Acetic Anhydride and Mixed Fatty Acid Anhydrides".
4716:
Adet PA (1798). "Mémoire sur l'acide acétique" [Memoir on acetic acid].
4486:
3895:
of a carboxylic acid. Upon treatment with a standard base, it converts to metal
2578:. About 75% of acetic acid made for use in the chemical industry is made by the
461:
10610:
10292:
10232:
10219:
10120:
9892:
9873:
9571:
9536:
9319:
9209:
9174:
9159:
9094:
9089:
8988:
8888:
8807:
8782:
8747:
8692:
8667:
8536:
8384:
8101:
8046:
8028:
7723:
7651:
7597:
7549:
7450:
7427:
7206:
7185:
6991:
6981:
6873:
6537:
6187:
6170:
5226:
Proceedings of the National Academy of Sciences of the United States of America
4260:
4145:
4076:
3940:
3726:
3617:
3509:
3497:
3397:
3194:
3155:
3120:. The alcohol-containing feed is trickled into the top of the tower, and fresh
2961:
2880:
2753:
2690:
2587:
2390:
2386:
2304:
2254:
2221:
2182:
1988:
1943:
1892:
The carboxymethyl functional group derived from removing one hydrogen from the
1808:
1701:, derived from acetic acid, is fundamental to all forms of life. When bound to
1348:
1323:
1279:
747:
709:
6779:
6463:
Bamford CH, Dewar MJ (1949). "608. The thermal decomposition of acetic acid".
6227:
5611:
5288:
5008:
4542:
1762:
1195:
1177:
10687:
10266:
9859:
9601:
9456:
9339:
9314:
9295:
9239:
9119:
9077:
9072:
8812:
8802:
8762:
8637:
8531:
8486:
8461:
8343:
8323:
8204:
8185:
8154:
8089:
8022:
8000:
7711:
7699:
7633:
7627:
7615:
7579:
7573:
7541:
7440:
7435:
7397:
7367:
7362:
7268:
7119:
7109:
7069:
7042:
7024:
6890:
6630:
6545:
6507:
6319:
World Health Organization model list of essential medicines: 22nd list (2021)
5856:
5818:
5619:
4405:
4294:
4199:
4126:
3841:
3722:, no high quality evidence supports this treatment for rotator cuff disease.
3719:
3439:
3389:
3381:
3284:
2941:
2929:
2872:
2662:
2579:
2555:
2357:
2110:
2087:
2030:
1725:
1682:
1477:
1433:
1315:
1311:
826:
672:
662:
365:
320:
145:
Vinegar (when dilute); Hydrogen acetate; Methanecarboxylic acid; Ethylic acid
5949:
5320:
Fiume MZ (June 2003). "Final report on the safety assessment of triacetin".
5238:
5130:
Zieborak K, Olszewski K (1958). "Solubility of n-paraffins in acetic acid".
4560:
3189:
bacteria produce acetic acid from one-carbon compounds, including methanol,
2094:
of glacial acetic acid, around 30% of which was used for the manufacture of
1390:
10090:
9677:
9531:
9384:
9324:
9304:
9276:
9204:
9084:
9067:
9022:
8973:
8878:
8598:
8551:
8399:
8132:
8095:
7951:
7729:
7687:
7663:
7639:
7567:
7561:
7555:
7455:
7417:
7315:
7246:
7236:
7139:
7124:
7104:
7074:
7006:
6881:
6291:
World Health Organization model list of essential medicines: 21st list 2019
6245:
6196:
6130:
6087:
6038:
5704:
Hromatka O, Ebner H (1959). "Vinegar by Submerged Oxidative Fermentation".
5341:
5306:
5257:
5087:
4153:
4121:
with iodine and ammonia to give a blue solution. Acetates when heated with
4064:
3711:
and if an area of white appears after about a minute the test is positive.
3489:
3105:
2945:
2937:
2899:
2780:
2496:
2484:
2472:
2065:
1931:
1741:
1710:
1698:
1694:
1291:
944:
934:
5986:
5552:
1116:
9651:
9561:
9526:
9493:
9419:
9394:
9234:
9109:
8993:
8908:
8898:
8628:
8556:
8148:
7735:
7603:
7591:
7407:
7157:
7134:
7129:
7114:
7099:
7094:
7014:
6986:
6928:
6923:
6918:
6870:
6578:"The Lanthanum Nitrate Test for Acetatein Inorganic Qualitative Analysis"
6472:
6449:
6440:
Blake PG, Jackson GE (1968). "The thermal decomposition of acetic acid".
3664:
3640:
3589:
3428:
3149:
3027:
2968:
2933:
2876:
2863:
2686:
2574:
Acetic acid is produced industrially both synthetically and by bacterial
2566:
2520:
2480:
2430:
2015:
1654:
1275:
1129:
689:
6499:
6327:
6299:
5744:
5717:
5044:
3055:
mashes. The overall chemical reaction facilitated by these bacteria is:
1102:
309:
9566:
9508:
9471:
9446:
9344:
9154:
9017:
8126:
7533:
7469:
7387:
7377:
7372:
7352:
7256:
7226:
7201:
7089:
7079:
6976:
6933:
6908:
6898:
6877:
6869:
4793:
4218:
3125:
3104:
is fermented at too high a temperature, acetobacter will overwhelm the
3097:
2678:
2488:
2468:
2460:
2414:
2382:
2095:
1706:
1702:
1109:
621:
385:
340:
280:
31:
7498:
6622:
6069:
6020:
5333:
5220:
Schwer B, Bunkenborg J, Verdin RO, Andersen JS, Verdin E (July 2006).
5079:
4958:
3636:(PET). In 2006, about 20% of acetic acid was used for TPA production.
3508:
removers, and wood stains. First, glycol monoethers are produced from
9498:
9363:
9199:
9003:
8883:
8737:
8712:
8166:
7487:
7477:
7465:
7412:
7402:
7324:
7311:
7241:
7180:
7084:
7061:
6962:
6952:
6002:
4378:
4349:
4281:
4171:
4048:
4007:
3995:
3920:
3749:
3296:
2976:
2848:
2693:
2511:
2500:
2079:
2053:
1948:
1918:
was known early in civilization as the natural result of exposure of
1774:
1406:
1295:
1046:
796:
508:
5670:
Kent and Riegel's Handbook of Industrial Chemistry and Biotechnology
5493:"Reportlinker Adds Global Acetic Acid Market Analysis and Forecasts"
4785:
3647:. For example, one stage in the commercial manufacture of synthetic
1724:
per year (t/a). Most of the world's acetic acid is produced via the
1720:
The global demand for acetic acid as of 2023 is about 17.88 million
1347:
Except where otherwise noted, data are given for materials in their
9466:
9378:
9179:
9042:
9027:
8998:
8867:
8642:
8466:
8410:
8404:
8373:
8318:
8286:
7392:
7175:
7149:
4915:
4890:
4587:
4157:
4015:
3753:
3656:
3401:
3353:
3345:
3299:
3288:
3198:
3186:
3117:
2957:
2887:
2868:
2856:
2666:
2619:
2610:
2595:
2583:
2504:
2426:
2366:
2320:
2118:
2102:
2090:
to recover acetic acid. At that time, Germany was producing 10,000
1969:
1846:
1729:
1686:
1674:
1425:
1075:
422:
415:
357:
300:
4932:"Thermodynamic Quantities for the Ionization Reactions of Buffers"
4540:
3878:
3782:
190:
9781:
9631:
9461:
9414:
9373:
9329:
9271:
9266:
9229:
9219:
9214:
9169:
9164:
9104:
9037:
8928:
8923:
8873:
8752:
8742:
8495:
7482:
7231:
6943:
6171:"Acetic acid treatment of pseudomonal wound infections--a review"
4185:
4167:
4149:
4019:
3944:
3896:
3871:
3742:
3648:
3625:
3597:
3505:
3435:
3377:
3272:
3268:
2791:
2635:
2599:
2551:
2492:
2446:
2410:
2394:
2308:
2186:
2178:
2134:
2003:
1995:
1935:
1927:
1915:
1812:
1757:
1658:
1642:
752:
652:
448:
84:
Skeletal formula of acetic acid with all explicit hydrogens added
4198:, used as a catalyst for organic coupling reactions such as the
2240:
2021:
9779:
9682:
9503:
9485:
8948:
8918:
8420:
4464:"Chemistry", volume 5, Encyclopædia Britannica, 1961, page 374.
3948:
3708:
3639:
Acetic acid is often used as a solvent for reactions involving
3605:
3534:
3485:
3292:
3109:
3090:
3052:
3040:
2891:
2852:
2803:
2591:
2453:
2422:
2418:
2378:
2285:
2126:
1953:
1893:
1833:
1794:
260:
5219:
4701:(Part 1, Organic ed.). London: Crosby Lockwood. pp.
2794:
components are readily oxidized by oxygen or even air to give
2445:
At physiological pHs, acetic acid is usually fully ionised to
1930:
extends into the third century BC, when the Greek philosopher
1526:
8717:
8647:
7529:
4565:
Immediately Dangerous to Life or Health Concentrations (IDLH)
4268:
4130:
3999:
3936:
3928:
3900:
3443:
3373:
3365:
3349:
3032:
3025:
For most of human history, acetic acid bacteria of the genus
2547:
2535:
2406:
2398:
2323:
solution (about the concentration of domestic vinegar) has a
1842:
1753:
1749:
1721:
1244:
TWA 10 ppm (25 mg/m) ST 15 ppm (37 mg/m)
472:
240:
180:
7309:
6650:. Centers for Disease Control and Prevention. Archived from
6169:
Nagoba BS, Selkar SP, Wadher BJ, Gandhi RC (December 2013).
6108:
5972:
2570:
Purification and concentration plant for acetic acid in 1884
1558:
1450:
524:
4011:
4003:
3604:. Acetic anhydride is also a reagent for the production of
3101:
3048:
3044:
3036:
2539:
2531:
2292:), acetic acid has acidic character. Acetic acid is a weak
2130:
1961:
1923:
1919:
1767:
1570:
1561:
1555:
1517:
1250:
1203:
642:
406:
6706:. International Programme on Chemical Safety. 5 June 2010.
6645:"Occupational Safety and Health Guideline for Acetic Acid"
5776:
5667:
5359:. Vol. 1 (6th ed.). London: Chapman & Hall.
4648:(3rd ed.). Tokyo: McGraw Hill Kogakusha. p. 135.
4454:. National Technical Information Service. 1974. p. 1.
2798:, which decompose to produce acetic acid according to the
1964:
boiled soured wine to produce a highly sweet syrup called
677:
118 to 119 °C; 244 to 246 °F; 391 to 392 K
6829:
Swedish Chemicals Agency. Information sheet – Acetic Acid
6377:. United States Food and Drug Administration. March 1995.
6347:
6313:
6285:
5509:
4840:, Harold A. Wittcoff, Bryan G. Reuben, Jeffery S. Plotkin
4374:
4189:
3369:
2476:
2091:
1837:
from acetic acid. The name "acetate" can also refer to a
1828:
1714:
1573:
1532:
1042:
6303:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
6168:
4891:"Detection and Confirmation of Interstellar Acetic Acid"
4888:
2771:
may also be produced in plants using rhodium catalysis.
2673:
react to produce acetic acid according to the equation:
2074:
By 1910, most glacial acetic acid was obtained from the
2040:
for the first time. This reaction sequence consisted of
6265:(5th ed.). Elsevier Health Sciences. p. 367.
5382:
3731:
World Health Organization's List of Essential Medicines
3496:. In addition, ether acetates are used as solvents for
2787:. This was the dominant technology in the early 1900s.
2623:
2324:
2162:
5886:
The Chemistry of Fragrances: From Perfumer to Consumer
5273:"Acetate Metabolism in Physiology, Cancer, and Beyond"
4643:
3624:
to purify organic compounds. Acetic acid is used as a
667:
16 to 17 °C; 61 to 62 °F; 289 to 290 K
10661:
8277:
6775:
National Pollutant Inventory – Acetic acid fact sheet
6344:
Food Composition Data: Production, Management and Use
6209:
5597:
5427:. SRI International. p. 602.5000. Archived from
5030:
4929:
4819:
Wagner FS (1978). "Acetic acid". In Grayson M (ed.).
4569:
National Institute for Occupational Safety and Health
4547:
National Institute for Occupational Safety and Health
3989:
3124:
supplied from the bottom by either natural or forced
1576:
1567:
1552:
1535:
1523:
1426:
358:
6833:
Process Flow sheet of Acetic acid Production by the
6600:
6212:"Electrotherapy modalities for rotator cuff disease"
4744:
New Haven Section Bulletin American Chemical Society
4329:
3283:
The primary use of acetic acid is the production of
2840:
Such oxidations require metal catalyst, such as the
2487:. Most of the acetate generated in cells for use in
2360:. In the vapour phase at 120 °C (248 °F),
1529:
6442:
Journal of the Chemical Society B: Physical Organic
6422:
6341:
3663:; here acetic acid acts both as a solvent and as a
2129:catalyst, was developed by German chemical company
1789:for acetic acid is AcOH (or HOAc), where Ac is the
1564:
1520:
394:
6718:"Standard Operating Procedure Glacial Acetic Acid"
5270:
5102:
4889:Mehringer DM, Snyder LE, Miao Y, Lovas FJ (1997).
4861:. Cambridge: Royal Society of Chemistry. pp.
4854:
4774:Journal of the American Institute for Conservation
5538:
5129:
3368:of acetic acid are commonly used as solvents for
3131:Nowadays, most vinegar is made in submerged tank
2764:is suppressed, and fewer by-products are formed.
2689:as an intermediate, and occurs in three steps. A
1934:described how vinegar acted on metals to produce
208:
30:"Acetic" redirects here. Not to be confused with
27:Colorless and faint organic acid found in vinegar
10685:
5271:Bose S, Ramesh V, Locasale JW (September 2019).
5158:Cheung H, Tanke RS, Torrence GP. "Acetic Acid".
3404:reaction from acetic acid and the corresponding
2224:North molecular cloud (also known as the Sgr B2
2189:-catalyzed production of glacial acetic acid is
1773:"Glacial acetic acid" is a name for water-free (
460:
6145:"Antiseptics on Wounds: An Area of Controversy"
5802:
5800:
5157:
4939:Journal of Physical and Chemical Reference Data
4821:Kirk-Othmer Encyclopedia of Chemical Technology
1748:. The systematic name "ethanoic acid", a valid
1091:
166:
6575:
5975:Gan to Kagaku Ryoho. Cancer & Chemotherapy
5848:Ullmann's Encyclopedia of Industrial Chemistry
5810:Ullmann's Encyclopedia of Industrial Chemistry
5378:
5376:
5161:Ullmann's Encyclopedia of Industrial Chemistry
4978:
2971:, which opened an ethylene oxidation plant in
2944:than acetic acid and are readily separated by
2613:will remain liquid while the acetic acid will
2165:Chemicals commercialised the Cativa catalyst (
1782:acid lowers its melting point by 0.2 °C.
10744:World Health Organization essential medicines
9765:
8263:
7514:
7295:
6855:
6558:
5840:
5838:
5757:
5703:
5418:
4623:(2nd ed.). CRC Press. pp. 102–104.
4227:, which is esterified to produce the reagent
3592:agent. As such, its major application is for
6594:
6462:
6439:
6335:
5844:
5797:
5593:
5591:
5589:
5587:
5199:. Lexington, Mass: D.C. Heath. p. 627.
4848:
4846:
4644:Hendrickson JB, Cram DJ, Hammond GS (1970).
4593:
3886:Two typical organic reactions of acetic acid
2479:. Unlike longer-chain carboxylic acids (the
1744:"acetic acid" is the most commonly used and
6569:
6216:The Cochrane Database of Systematic Reviews
6051:
5699:
5697:
5373:
4575:
2594:to acetic acid, and gas phase oxidation of
1972:that was produced in lead pots was rich in
9772:
9758:
8270:
8256:
7521:
7507:
7302:
7288:
6862:
6848:
6394:. Health Canada. August 2018. p. 591.
5998:
5996:
5835:
5354:
5153:
5151:
5149:
5147:
5145:
5109:(5th ed.). Brooks/Cole. p. 818.
3931:of acetic acid can likewise be formed via
3085:A dilute alcohol solution inoculated with
2696:is needed for the carbonylation (step 2).
2530:. These bacteria are found universally in
1487:
1464:
1436:
539:
330:
288:
6696:
6565:(4th ed.). CUP Archive. p. 110.
6326:
6298:
6235:
6186:
6077:
6028:
5957:
5730:
5584:
5414:
5412:
5410:
5408:
5406:
5296:
5247:
5237:
5007:
4914:
4852:
4843:
4734:
4728:
4690:
4688:
4686:
3915:. Other substitution derivatives include
3138:
3020:
2774:
2661:Most acetic acid is produced by methanol
2656:
2626:Chemicals. Other major producers include
2483:), acetic acid does not occur in natural
496:
6675:
6488:Journal of the American Chemical Society
6485:
6479:
5694:
5123:
4930:Goldberg R, Kishore N, Lennen R (2002).
4923:
4770:"Identification of dyes on old textiles"
4767:
4761:
4541:NIOSH Pocket Guide to Chemical Hazards.
4467:
3278:
2565:
2336:
2239:
2020:
7528:
6770:International Chemical Safety Card 0363
6552:
6429:. London: Blackie and Son. p. 155.
6372:"CPG Sec. 525.825 Vinegar, Definitions"
6307:
6279:
5993:
5931:
5902:
5570:(3rd ed.). Springer. p. 151.
5565:
5192:
5142:
5100:
4658:
4598:(6th ed.). Butterworth-Heinemann.
4581:IUPAC Provisional Recommendations 2004
2967:In more recent times, chemical company
2609:using an ice bath. The water and other
2499:. However, the artificial triglyceride
1460:
657:1.049 g/cm (liquid); 1.27 g/cm (solid)
535:
438:
308:
14:
10686:
9802:
6780:NIOSH Pocket Guide to Chemical Hazards
6410:Official Journal of the European Union
6175:Journal of Infection and Public Health
5733:Industrial & Engineering Chemistry
5706:Industrial & Engineering Chemistry
5640:
5634:
5403:
5057:
5051:
5024:
4981:"The crystal structure of acetic acid"
4884:
4882:
4818:
4812:
4698:Industrial and Manufacturing Chemistry
4694:
4683:
4618:
4612:
4536:
4534:
4532:
4503:
2554:, where it appears to serve as a mild
2206:Berkeley-Illinois-Maryland Association
2196:
1584:, is an acidic, colourless liquid and
1478:
1148:427 °C (801 °F; 700 K)
321:
10749:Organic compounds with 2 carbon atoms
10468:
9753:
8251:
7502:
7283:
6843:
6412:. European Commission. February 2016.
6406:"Commission Regulation (EU) 2016/263"
6321:. Geneva: World Health Organization.
6293:. Geneva: World Health Organization.
6258:
5319:
4972:
4857:Green Chemistry, an Introductory Text
3718:While diluted acetic acid is used in
3620:, acetic acid is frequently used for
3239:bacteria are less acid-tolerant than
2951:
2862:The typical reaction is conducted at
2421:. With higher alkanes (starting with
2373:
2181:for greater efficiency. Known as the
1411:
1134:40 °C (104 °F; 313 K)
567:Key: QTBSBXVTEAMEQO-UHFFFAOYSA-N
564:InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
268:
248:
6735:
5934:"Injection of Acetic Acid in Cancer"
5879:
5873:
5348:
4715:
4596:Purification of Laboratory Chemicals
4517:
4280:Concentrated acetic acid (≥ 25%) is
4248:
4217:. MCA is used in the manufacture of
4136:
3765:
3340:Vinyl acetate can be polymerised to
2767:By altering the process conditions,
2467:enzymes, where it is central to the
2341:Cyclic dimer of acetic acid; dashed
948:
938:
6637:
6423:Bernthsen A, Sudborough JJ (1922).
5908:
5806:
5322:International Journal of Toxicology
5060:The Journal of Physical Chemistry A
4879:
4529:
3927:from two molecules of acetic acid.
3529:of two molecules of acetic acid is
3520:
3359:
2898:to produce acetic acid can oxidize
2890:are used for butane oxidation, the
1685:, acetic acid is controlled by the
1649:Acetic acid is the second simplest
451:
421:
414:
94:Ball and stick model of acetic acid
24:
9642:Nexus for Exoplanet System Science
7905:6,9,12,15,18,21-Tetracosahexaenoic
6669:
6342:Greenfield H, Southgate D (2003).
3990:Reactions with inorganic compounds
3891:Acetic acid undergoes the typical
2956:Acetaldehyde may be prepared from
1087:
89:
79:
59:
49:
25:
10765:
9542:Atomic and molecular astrophysics
8279:Molecules detected in outer space
7899:9,12,15,18,21-Tetracosapentaenoic
6763:
3611:
3400:. They are typically produced by
3147:, including members of the genus
1766:", which is related to the word "
967:
10671:
9780:Acetyl halides and salts of the
9732:
9720:
9708:
9697:
9696:
8503:
8494:
8485:
6792:(US Permissible exposure limits)
6785:Method for sampling and analysis
6052:Madhusudhan VL (December 2016).
5882:"4.2.15 Bicyclic Monoterpenoids"
4737:"This month in chemical history"
4621:Organic Chemist's Desk Reference
4367:
4362:
4342:
4322:
3877:
3848:
3820:
3803:
3781:
2677:
2605:Acetic acid can be purified via
2330:
2296:. In aqueous solution, it has a
1976:, a sweet substance also called
1548:
1513:
1355:
1012:
1007:
105:
9667:Polycyclic aromatic hydrocarbon
7310:Drugs used for diseases of the
6710:
6514:
6465:Journal of the Chemical Society
6456:
6433:
6416:
6398:
6381:
6364:
6252:
6203:
6162:
6137:
6102:
6045:
5966:
5925:
5791:10.1016/j.enzmictec.2006.09.017
5779:Enzyme and Microbial Technology
5770:
5751:
5724:
5661:
5559:
5532:
5503:
5485:
5469:
5450:
5444:Chemical & Engineering News
5435:
5357:Dictionary of Organic Compounds
5313:
5264:
5213:
5186:
5094:
4979:Jones RE, Templeton DH (1958).
4831:
4709:
4652:
4637:
4426:
4417:
4237:, which is a common reagent in
4129:, which can be detected by its
4075:+ vinegar" reaction giving off
3699:Acetic acid is used as part of
2440:
2284:Because of this release of the
2220:. It was first detected in the
1735:
1351:(at 25 °C , 100 kPa).
976:(Pharmacy medicine) and S6
54:Skeletal formula of acetic acid
6576:Neelakantam K, Row LR (1940).
6562:Qualitative Inorganic Analysis
6532:(11): 79–88. 1 November 1957.
5568:Survey of Industrial Chemistry
5499:. June 2014. p. contents.
4735:Goldwhite H (September 2003).
4553:
4458:
4444:
3685:
3302:, conducted in the gas phase.
3243:. Even the most acid-tolerant
2979:metal catalyst supported on a
2964:, and then oxidised as above.
2347:lines represent hydrogen bonds
2218:Owens Valley Radio Observatory
1777:) acetic acid. Similar to the
64:Spacefill model of acetic acid
13:
1:
9592:Extraterrestrial liquid water
6820:Acetic acid bound to proteins
6603:Journal of Chemical Education
6559:Charlot G, Murray RG (1954).
5397:10.1016/S0926-860X(01)00800-6
5170:10.1002/14356007.a01_045.pub2
5033:Journal of Physical Chemistry
4895:Astrophysical Journal Letters
4524:Lange's Handbook of Chemistry
4438:
3707:. The acid is applied to the
3653:Wagner-Meerwein rearrangement
3488:, however, are produced from
3434:For example, acetic acid and
2590:isomerization, conversion of
2561:
2507:and acetic acid in the body.
2491:is synthesized directly from
2235:
1991:among the Roman aristocracy.
1896:group of acetic acid has the
1841:containing this anion, or an
1218:(US health exposure limits):
5672:. Springer. pp. 32–34.
5655:10.1016/j.cattod.2008.10.054
5600:Catalysis Surveys from Japan
5526:10.1016/0920-5861(92)80188-S
5481:. Mordor Intelligence. 2023.
5419:Malveda M, Funada C (2003).
5385:Applied Catalysis A: General
4838:Industrial Organic Chemicals
4665:. Cengage Learning. p.
4662:Common Medical Abbreviations
4594:Armarego WL, Chai C (2009).
4113:for salts of acetic acid is
3760:
3632:(TPA), the raw material for
2752:, and the iridium-catalyzed
2510:Acetic acid is produced and
2403:relative static permittivity
2351:
2060:and aqueous chlorination to
2002:described the production of
7:
8823:Protonated hydrogen cyanide
6796:ChemSub Online: Acetic acid
6790:29 CFR 1910.1000, Table Z-1
6723:. UCMERCED. 19 October 2012
6676:Sherertz PC (1 June 1994).
6123:10.1016/j.burns.2008.11.009
6058:International Wound Journal
5807:Roscher G. "Vinyl Esters".
5425:Chemicals Economic Handbook
4487:10.1039/9781849733069-00648
4394:
4275:
3108:naturally occurring on the
2253:The hydrogen centre in the
2210:Hat Creek Radio Observatory
1166:or concentration (LD, LC):
75:
45:
10:
10770:
10470:
6538:10.5006/0010-9312-13.11.79
6331:. WHO/MHP/HPS/EML/2021.02.
6188:10.1016/j.jiph.2013.05.005
5355:Buckingham J, ed. (1996).
4823:(3rd ed.). New York:
4619:Cooper C (9 August 2010).
4479:Royal Society of Chemistry
4391:of 5.4–16% concentration.
3740:
3689:
3634:polyethylene terephthalate
3348:, which are components in
3267:Acetic acid is a chemical
2940:, all of which have lower
2527:Clostridium acetobutylicum
2248:
1910:
1823:), is thus represented as
1231:TWA 10 ppm (25 mg/m)
1208:16000 ppm (rat, 4 h)
29:
9804:
9789:
9691:
9582:Earliest known life forms
9577:Diffuse interstellar band
9517:
9437:
9362:
9253:
9188:
9128:
9056:
9048:Protonated cyanoacetylene
8962:
8856:
8818:Protonated carbon dioxide
8778:Hydromagnesium isocyanide
8726:
8512:
8483:
8294:
8285:
8214:
8195:
8176:
8117:
8074:
7979:
7914:
7781:
7540:
7464:
7426:
7323:
7219:
7194:
7166:
7148:
7060:
7051:
7033:
7005:
6961:
6942:
6889:
6835:Carbonylation of Methanol
6704:"ICSC 0363 – ACETIC ACID"
6315:World Health Organization
6287:World Health Organization
6228:10.1002/14651858.CD012225
5289:10.1016/j.tcb.2019.05.005
5009:10.1107/S0365110X58001341
4263:and industrial exposure.
4253:
3701:cervical cancer screening
3692:Acetic acid (medical use)
3645:Friedel-Crafts alkylation
1938:useful in art, including
1500:
1495:
1476:
1444:
1424:
1419:
1401:
1396:
1345:
1338:
1333:
1261:
1212:
1162:
988:
983:
921:
819:
596:
576:
551:
150:
142:
130:
118:
113:
104:
74:
44:
9627:Iron–sulfur world theory
9622:Photodissociation region
9325:Methyl-cyano-diacetylene
7958:7,10,13-Octadecatrienoic
6810:dynamic liquid viscosity
5857:10.1002/14356007.a01_065
5819:10.1002/14356007.a27_419
5497:Market Research Database
4411:
3757:best-known application.
3736:
2762:water-gas shift reaction
2756:. The latter process is
2177:), which is promoted by
2086:was then acidified with
2025:Crystallised acetic acid
1334:Supplementary data page
1055:Precautionary statements
223:AcOH (acetyl hydroxide)
9702:Category:Astrochemistry
9292:, fullerene, buckyball)
8979:Cyanobutadiynyl radical
8954:Silicon-carbide cluster
8944:Protonated formaldehyde
7338:Aluminium acetotartrate
7263:Lactobacillus fermentum
5950:10.1136/bmj.2.305.512-a
5851:. Weinheim: Wiley-VCH.
5813:. Weinheim: Wiley-VCH.
5612:10.1023/A:1019003230537
5239:10.1073/pnas.0603968103
5164:. Weinheim: Wiley-VCH.
5018:2027/mdp.39015077597907
4401:Acetic acid (data page)
4152:industry and as a food
4055:acid-resistant film of
3588:Acetic anhydride is an
3262:
2886:Similar conditions and
2029:In 1845 German chemist
2018:proved them identical.
2012:ketonic decarboxylation
1987:, which contributed to
1831:resulting from loss of
1705:, it is central to the
1693:and as a condiment. In
1543:, systematically named
1502:Acetic acid (data page)
1340:Acetic acid (data page)
761:Magnetic susceptibility
10734:Photographic chemicals
9715:Outer space portal
9557:Circumstellar envelope
8522:Aluminium(I) hydroxide
8432:Phosphorus mononitride
8309:Aluminium monofluoride
8304:Aluminium monochloride
8108:7,10,13-Eicosatrienoic
7964:9,12,15-Eicosatrienoic
7446:Fluocinolone acetonide
6972:Diiodohydroxyquinoline
5446:: 67–76. 11 July 2005.
5277:Trends in Cell Biology
4988:Acta Crystallographica
4750:(3): 4. Archived from
4583:Chapter P-12.1; page 4
4339:4.16–14.99 mol/L
3994:Acetic acid is mildly
3933:Fischer esterification
3139:Anaerobic fermentation
3021:Oxidative fermentation
2785:hydration of acetylene
2775:Acetaldehyde oxidation
2657:Methanol carbonylation
2571:
2435:dimethyl terephthalate
2425:), acetic acid is not
2348:
2245:
2161:). In the late 1990s,
2026:
1761:
1657:). It is an important
1184:3.31 g/kg, oral (rat)
1098:
917:−875.50–874.82 kJ/mol
890:−483.88–483.16 kJ/mol
95:
85:
65:
55:
9612:Interplanetary medium
9587:Extraterrestrial life
9225:Octatetraynyl radical
8843:Tricarbon monosulfide
8390:Magnesium monohydride
5553:10.1055/s-2007-966002
5462:23 April 2022 at the
5442:"Production report".
4825:John Wiley & Sons
4481:. 2014. p. 745.
4359:>14.99 mol/L
4319:1.67–4.16 mol/L
4267:results in intensive
4196:Palladium(II) acetate
4071:, as in the popular "
4018:gas and salts called
3703:in many areas in the
3628:in the production of
3608:and other compounds.
3380:. The esters include
3291:and acetic acid with
3279:Vinyl acetate monomer
2685:The process involves
2569:
2465:acetyl-CoA synthetase
2340:
2243:
2230:radio interferometers
2226:Large Molecule Heimat
2064:, and concluded with
2024:
1952:, a green mixture of
1097:
647:Heavily vinegar-like
132:Systematic IUPAC name
93:
83:
63:
53:
9739:Chemistry portal
9727:Astronomy portal
9673:RNA world hypothesis
9657:PAH world hypothesis
9350:Heptatrienyl radical
9282:Buckminsterfullerene
9170:Methylcyanoacetylene
8678:Silicon carbonitride
8653:Methylidynephosphane
8619:Magnesium isocyanide
8527:Aluminium isocyanide
8329:Carbon monophosphide
7343:Aluminium triacetate
6473:10.1039/JR9490002877
6450:10.1039/J29680001153
6262:Clinical Dermatology
4853:Lancaster M (2002).
4235:Trifluoroacetic acid
4215:trichloroacetic acid
3255:, rather than using
2628:Millennium Chemicals
2518:, notably the genus
2516:acetic acid bacteria
2244:Acetic acid crystals
2133:in 1963. In 1968, a
2082:, and the resulting
2062:trichloroacetic acid
2050:carbon tetrachloride
1994:In the 16th-century
1885:. In the context of
1791:pseudoelement symbol
1746:preferred IUPAC name
1196:median concentration
1080:(fire diamond)
120:Preferred IUPAC name
10724:Household chemicals
10709:Commodity chemicals
9617:Interstellar medium
9597:Forbidden mechanism
9410:Hydrogen isocyanide
9100:Hexatriynyl radical
8683:c-Silicon dicarbide
8588:Hydrogen isocyanide
8452:Silicon monosulfide
8427:Phosphorus monoxide
8395:Methylidyne radical
8354:Fluoromethylidynium
8314:Aluminium(II) oxide
6743:"C&L Inventory"
6615:1947JChEd..24..353B
6500:10.1021/ja00123a013
5745:10.1021/ie50257a005
5718:10.1021/ie50598a033
5678:2007karh.book......
5566:Chenier PJ (2002).
5431:on 14 October 2011.
5232:(27): 10224–10229.
5193:Zumdahl SS (1986).
5072:2005JPCA..109.5438T
5045:10.1021/j100161a065
5000:1958AcCry..11..484J
4951:2002JPCRD..31..231G
4907:1997ApJ...480L..71M
4768:Schweppe H (1979).
4659:DeSousa LR (1995).
3725:As a treatment for
3525:The product of the
3494:Tishchenko reaction
2985:silicotungstic acid
2802:, illustrated with
2665:. In this process,
2607:fractional freezing
2544:vaginal lubrication
2303:value of 4.76. Its
2197:Interstellar medium
2076:pyroligneous liquor
2058:tetrachloroethylene
2038:inorganic compounds
1887:acid–base reactions
1393:
1202:5620 ppm (mouse, 1
684:Solubility in water
629: g·mol
230:Beilstein Reference
41:
10714:E-number additives
9637:Molecules in stars
9607:Intergalactic dust
9552:Circumstellar dust
9494:Naphthalene cation
9429:Trihydrogen cation
9405:Hydrogen deuteride
9330:Methyltriacetylene
9165:Hexapentaenylidene
8984:E-Cyanomethanimine
8904:Cyclopropenylidene
8838:Tricarbon monoxide
8828:Silicon tricarbide
8798:Methylene amidogen
8788:Isothiocyanic acid
8703:Thioxoethenylidene
8663:Trihydrogen cation
8477:Titanium(II) oxide
8437:Potassium chloride
8416:Sulfur mononitride
8359:Helium hydride ion
8334:Carbon monosulfide
8161:8,11-Eicosadienoic
8041:Dihomo-γ-linolenic
7970:β-Eicosatetraenoic
7869:Dihomo-α-linolenic
7754:Heptatriacontanoic
5932:Barclay J (1866).
5101:McMurry J (2000).
4968:on 6 October 2008.
4511:"acetic acid_msds"
4261:animal experiments
4229:ethyl bromoacetate
4164:Copper(II) acetate
4115:iron(III) chloride
3893:chemical reactions
3193:, or a mixture of
3145:anaerobic bacteria
2952:Ethylene oxidation
2632:Sterling Chemicals
2572:
2374:Solvent properties
2349:
2246:
2027:
1958:copper(II) acetate
1687:food additive code
1389:
1378:Infobox references
1262:Related compounds
1253:(Immediate danger)
1099:
724:mmHg (20 °C)
637:Colourless liquid
96:
86:
66:
56:
39:
10659:
10658:
10653:
10652:
9747:
9746:
9662:Pseudo-panspermia
9358:
9357:
9305:Cyanodecapentayne
9245:N-Methylformamide
9220:Methyldiacetylene
9145:Aminoacetonitrile
9115:Methyl isocyanate
9033:Methyl isocyanide
8914:Isocyanoacetylene
8894:Cyanoformaldehyde
8773:Hydrogen peroxide
8658:Potassium cyanide
8614:Magnesium cyanide
8567:Disilicon carbide
8562:Dicarbon monoxide
8369:Hydrogen fluoride
8364:Hydrogen chloride
8245:
8244:
7766:Nonatriacontanoic
7760:Octatriacontanoic
7496:
7495:
7383:Hydrogen peroxide
7277:
7276:
7215:
7214:
6623:10.1021/ed024p353
6494:(18): 5114–5119.
6426:Organic Chemistry
6272:978-0-323-08037-8
6259:Habif TP (2009).
6070:10.1111/iwj.12428
6021:10.1136/bmj.h3084
5895:978-0-85404-824-3
5712:(10): 1279–1280.
5687:978-0-387-27842-1
5577:978-0-306-47246-6
5466:. SRI Consulting.
5366:978-0-412-54090-5
5334:10.1080/747398359
5328:(Suppl 2): 1–10.
5206:978-0-669-04529-1
5116:978-0-534-37366-5
5105:Organic Chemistry
5080:10.1021/jp058004j
5066:(24): 5438–5444.
4959:10.1063/1.1416902
4872:978-0-85404-620-1
4718:Annales de Chimie
4695:Martin G (1917).
4676:978-0-8273-6643-5
4646:Organic Chemistry
4630:978-1-4398-1166-5
4605:978-1-85617-567-8
4496:978-0-85404-182-4
4477:. Cambridge: The
4384:
4383:
4249:Health and safety
4239:organic synthesis
4211:Chloroacetic acid
4178:Aluminium acetate
4137:Other derivatives
4119:lanthanum nitrate
3766:Organic chemistry
3661:isobornyl acetate
3630:terephthalic acid
3622:recrystallization
3602:photographic film
3594:cellulose acetate
3417:COO−H + HO−R → CH
3342:polyvinyl acetate
3093:to the bacteria.
2800:chemical equation
2644:Svensk Etanolkemi
2381:acetic acid is a
2137:-based catalyst (
2036:acetic acid from
2010:of lead acetate,
1827:. Acetate is the
1793:representing the
1691:acidity regulator
1671:polyvinyl acetate
1667:photographic film
1663:cellulose acetate
1599:(also written as
1507:
1506:
1446:CompTox Dashboard
1386:Chemical compound
1384:
1383:
1320:Potassium acetate
1304:Chloroacetic acid
1287:Related compounds
1037:Hazard statements
971:
767:−31.54·10 cm/mol
718:kPa (20 °C)
520:CompTox Dashboard
192:Interactive image
100:
99:
70:
69:
16:(Redirected from
10761:
10754:Acetyl compounds
10676:
10675:
10674:
10667:
9793:
9792:
9774:
9767:
9760:
9751:
9750:
9737:
9736:
9735:
9725:
9724:
9723:
9713:
9712:
9711:
9700:
9699:
9647:Organic compound
9547:Chemical formula
9452:Dihydroxyacetone
9400:Hydrogen cyanide
9085:Cyanodiacetylene
8939:Propadienylidene
8833:Thioformaldehyde
8708:Titanium dioxide
8673:Sodium hydroxide
8594:Hydrogen sulfide
8582:Hydrogen cyanide
8542:Carbonyl sulfide
8507:
8498:
8489:
8447:Silicon monoxide
8380:Hydroxyl radical
8292:
8291:
8272:
8265:
8258:
8249:
8248:
8216:ω−12 Unsaturated
8197:ω−11 Unsaturated
8178:ω−10 Unsaturated
7881:Eicosapentaenoic
7875:Eicosatetraenoic
7839:Palmitolinolenic
7833:Myristolinolenic
7748:Hexatriacontylic
7523:
7516:
7509:
7500:
7499:
7347:Burow's solution
7304:
7297:
7290:
7281:
7280:
7207:Methylrosaniline
7058:
7057:
6864:
6857:
6850:
6841:
6840:
6758:
6757:
6755:
6753:
6739:
6733:
6732:
6730:
6728:
6722:
6714:
6708:
6707:
6700:
6694:
6693:
6692:on 4 March 2016.
6691:
6684:
6673:
6667:
6666:
6664:
6662:
6656:
6649:
6641:
6635:
6634:
6598:
6592:
6591:
6589:
6587:
6582:
6573:
6567:
6566:
6556:
6550:
6549:
6518:
6512:
6511:
6483:
6477:
6476:
6460:
6454:
6453:
6437:
6431:
6430:
6420:
6414:
6413:
6402:
6396:
6395:
6393:
6385:
6379:
6378:
6376:
6368:
6362:
6361:
6339:
6333:
6332:
6330:
6311:
6305:
6304:
6302:
6283:
6277:
6276:
6256:
6250:
6249:
6239:
6207:
6201:
6200:
6190:
6166:
6160:
6159:
6157:
6155:
6149:www.medscape.com
6141:
6135:
6134:
6106:
6100:
6099:
6081:
6064:(6): 1129–1136.
6049:
6043:
6042:
6032:
6000:
5991:
5990:
5970:
5964:
5963:
5961:
5929:
5923:
5922:
5920:
5918:
5906:
5900:
5899:
5880:Sell CS (2006).
5877:
5871:
5870:
5842:
5833:
5832:
5804:
5795:
5794:
5785:(5): 1234–1243.
5774:
5768:
5767:
5755:
5749:
5748:
5728:
5722:
5721:
5701:
5692:
5691:
5665:
5659:
5658:
5649:(3–4): 285–291.
5638:
5632:
5631:
5595:
5582:
5581:
5563:
5557:
5556:
5547:(8): 1121–1150.
5536:
5530:
5529:
5507:
5501:
5500:
5489:
5483:
5482:
5473:
5467:
5454:
5448:
5447:
5439:
5433:
5432:
5416:
5401:
5400:
5391:(1–2): 253–265.
5380:
5371:
5370:
5352:
5346:
5345:
5317:
5311:
5310:
5300:
5268:
5262:
5261:
5251:
5241:
5217:
5211:
5210:
5190:
5184:
5183:
5155:
5140:
5139:
5127:
5121:
5120:
5108:
5098:
5092:
5091:
5055:
5049:
5048:
5039:(8): 3315–3322.
5028:
5022:
5021:
5011:
4985:
4976:
4970:
4969:
4967:
4961:. Archived from
4936:
4927:
4921:
4920:
4918:
4886:
4877:
4876:
4860:
4850:
4841:
4835:
4829:
4828:
4816:
4810:
4809:
4807:
4805:
4796:. Archived from
4765:
4759:
4758:
4757:on 4 March 2009.
4756:
4741:
4732:
4726:
4725:
4713:
4707:
4706:
4692:
4681:
4680:
4656:
4650:
4649:
4641:
4635:
4634:
4616:
4610:
4609:
4591:
4585:
4579:
4573:
4572:
4557:
4551:
4550:
4538:
4527:
4521:
4515:
4514:
4507:
4501:
4500:
4471:
4465:
4462:
4456:
4455:
4448:
4433:
4430:
4424:
4421:
4389:explosive limits
4380:
4376:
4371:
4366:
4351:
4346:
4331:
4326:
4291:
4290:
4225:Bromoacetic acid
4182:iron(II) acetate
4123:arsenic trioxide
4105:
4043:
3985:
3968:
3947:, or to produce
3917:acetic anhydride
3910:
3881:
3864:
3852:
3838:
3824:
3807:
3797:
3785:
3705:developing world
3584:
3559:
3531:acetic anhydride
3521:Acetic anhydride
3502:acrylic lacquers
3480:
3426:
3394:isobutyl acetate
3360:Ester production
3336:
3227:This ability of
3223:
3181:
3081:
3039:, and fermented
3013:
2924:
2836:
2769:acetic anhydride
2750:Monsanto process
2744:
2727:
2714:
2681:
2652:
2346:
2334:
2318:
2291:
2280:
2278:
2277:
2274:
2214:Millimeter Array
2176:
2159:Monsanto process
2155:Monsanto Company
2152:
2115:British Celanese
2071:to acetic acid.
2046:carbon disulfide
2008:dry distillation
2000:Andreas Libavius
1956:salts including
1906:
1898:chemical formula
1884:
1872:
1864:
1856:
1836:
1826:
1822:
1806:
1679:descaling agents
1659:chemical reagent
1640:
1625:
1610:
1598:
1590:chemical formula
1586:organic compound
1583:
1582:
1579:
1578:
1575:
1572:
1569:
1566:
1563:
1560:
1557:
1554:
1542:
1541:
1538:
1537:
1534:
1531:
1528:
1525:
1522:
1519:
1491:
1480:
1469:
1468:
1454:
1452:
1440:
1428:
1415:
1394:
1392:
1388:
1368:
1362:
1359:
1358:
1300:Acetic anhydride
1270:carboxylic acids
1154:Explosive limits
1119:
1112:
1105:
1090:
1070:
1066:
1062:
1048:
1044:
1016:
1011:
969:
966:
952:
942:
913:
886:
863:158.0 J/(K⋅mol)
859:
839:123.1 J/(K⋅mol)
835:
820:Thermochemistry
774:Refractive index
723:
717:
628:
615:
604:Chemical formula
544:
543:
528:
526:
500:
464:
453:
442:
425:
418:
398:
374:Gmelin Reference
360:
342:
334:
323:
312:
292:
272:
252:
212:
194:
170:
109:
76:
46:
42:
38:
21:
10769:
10768:
10764:
10763:
10762:
10760:
10759:
10758:
10684:
10683:
10682:
10672:
10670:
10662:
10660:
10655:
10654:
10618:
10614:
10603:
10595:
10582:
10574:
10566:
10558:
10550:
10542:
10534:
10526:
10518:
10507:
10499:
10491:
10483:
10395:
10387:
10382:
10380:
10372:
10367:
10360:
10355:
10353:
10349:
10341:
10333:
10307:
10296:
10278:
10273:
10269:
10259:
10251:
10246:
10244:
10236:
10228:
10215:
10207:
10203:
10195:
10190:
10187:
10183:
10172:
10161:
10153:
10143:
10123:
10113:
10102:
10094:
10086:
10081:
10074:
10066:
10058:
10053:
10051:
10043:
10038:
10036:
10028:
10023:
10021:
10013:
10005:
9997:
9987:
9967:
9951:
9947:
9943:
9938:
9935:
9930:
9927:
9922:
9918:
9916:
9908:
9900:
9895:
9881:
9868:
9858:
9851:
9847:
9842:
9840:
9832:
9828:
9823:
9821:
9785:
9778:
9748:
9743:
9733:
9731:
9721:
9719:
9709:
9707:
9687:
9513:
9489:
9480:
9433:
9423:
9366:
9354:
9335:Propionaldehyde
9310:Ethylene glycol
9299:
9291:
9287:
9258:
9256:
9249:
9205:Cyanohexatriyne
9191:
9184:
9131:
9124:
9059:
9052:
9012:
8965:
8958:
8929:Methoxy radical
8859:
8852:
8848:Thiocyanic acid
8729:
8722:
8632:
8572:Ethynyl radical
8508:
8502:
8501:
8500:
8499:
8493:
8492:
8491:
8490:
8481:
8472:Sulfur monoxide
8457:Sodium chloride
8442:Silicon carbide
8349:Diatomic carbon
8339:Carbon monoxide
8281:
8276:
8246:
8241:
8210:
8191:
8172:
8119:ω−9 Unsaturated
8113:
8076:ω−7 Unsaturated
8070:
8035:Dihomo-linoleic
7995:12-Octadecenoic
7989:8-Tetradecenoic
7981:ω−6 Unsaturated
7975:
7930:Palmitovaccenic
7916:ω−5 Unsaturated
7910:
7893:Docosahexaenoic
7827:Myristolinoleic
7821:Myristovaccenic
7783:ω−3 Unsaturated
7777:
7718:Hentriacontylic
7536:
7527:
7497:
7492:
7460:
7428:Corticosteroids
7422:
7358:Chloramphenicol
7319:
7308:
7278:
7273:
7252:Povidone-iodine
7211:
7190:
7162:
7144:
7047:
7029:
7001:
6957:
6938:
6914:Oxytetracycline
6904:Chloramphenicol
6885:
6874:anti-infectives
6868:
6814:surface tension
6800:Calculation of
6766:
6761:
6751:
6749:
6741:
6740:
6736:
6726:
6724:
6720:
6716:
6715:
6711:
6702:
6701:
6697:
6689:
6682:
6674:
6670:
6660:
6658:
6657:on 8 March 2020
6654:
6647:
6643:
6642:
6638:
6599:
6595:
6585:
6583:
6580:
6574:
6570:
6557:
6553:
6520:
6519:
6515:
6484:
6480:
6461:
6457:
6438:
6434:
6421:
6417:
6404:
6403:
6399:
6391:
6387:
6386:
6382:
6374:
6370:
6369:
6365:
6358:
6350:. p. 146.
6340:
6336:
6312:
6308:
6284:
6280:
6273:
6257:
6253:
6222:(6): CD012225.
6208:
6204:
6167:
6163:
6153:
6151:
6143:
6142:
6138:
6107:
6103:
6050:
6046:
6001:
5994:
5971:
5967:
5930:
5926:
5916:
5914:
5913:. Sigma-Aldrich
5907:
5903:
5896:
5878:
5874:
5867:
5843:
5836:
5829:
5805:
5798:
5775:
5771:
5756:
5752:
5729:
5725:
5702:
5695:
5688:
5666:
5662:
5643:Catalysis Today
5639:
5635:
5596:
5585:
5578:
5564:
5560:
5537:
5533:
5513:Catalysis Today
5508:
5504:
5491:
5490:
5486:
5475:
5474:
5470:
5464:Wayback Machine
5455:
5451:
5441:
5440:
5436:
5417:
5404:
5381:
5374:
5367:
5353:
5349:
5318:
5314:
5269:
5265:
5218:
5214:
5207:
5191:
5187:
5180:
5156:
5143:
5138:(2): 3315–3322.
5128:
5124:
5117:
5099:
5095:
5056:
5052:
5029:
5025:
4983:
4977:
4973:
4965:
4934:
4928:
4924:
4887:
4880:
4873:
4851:
4844:
4836:
4832:
4817:
4813:
4803:
4801:
4786:10.2307/3179569
4766:
4762:
4754:
4739:
4733:
4729:
4714:
4710:
4693:
4684:
4677:
4657:
4653:
4642:
4638:
4631:
4617:
4613:
4606:
4592:
4588:
4580:
4576:
4559:
4558:
4554:
4539:
4530:
4522:
4518:
4509:
4508:
4504:
4497:
4473:
4472:
4468:
4463:
4459:
4450:
4449:
4445:
4441:
4436:
4431:
4427:
4422:
4418:
4414:
4397:
4297:
4278:
4256:
4251:
4139:
4111:colour reaction
4103:
4099:
4095:
4091:
4087:
4083:
4061:stainless steel
4057:aluminium oxide
4042:
4038:
4034:
4030:
4026:
3992:
3983:
3979:
3975:
3971:
3967:
3963:
3959:
3955:
3923:is produced by
3913:acetyl chloride
3908:
3904:
3889:
3888:
3887:
3884:
3883:
3882:
3875:
3867:
3866:
3865:
3862:
3858:
3854:
3853:
3845:
3844:
3836:
3832:
3826:
3825:
3818:
3810:
3809:
3808:
3800:
3799:
3796:
3792:
3787:
3786:
3779:
3776:acetyl chloride
3768:
3763:
3745:
3739:
3729:, it is on the
3694:
3688:
3680:perchloric acid
3614:
3582:
3578:
3574:
3570:
3566:
3562:
3557:
3553:
3549:
3545:
3541:
3523:
3514:propylene oxide
3478:
3474:
3470:
3466:
3462:
3458:
3454:
3450:
3424:
3420:
3416:
3412:
3362:
3334:
3330:
3326:
3322:
3318:
3314:
3310:
3306:
3281:
3265:
3221:
3217:
3213:
3209:
3205:
3191:carbon monoxide
3179:
3175:
3171:
3167:
3163:
3141:
3079:
3075:
3071:
3067:
3063:
3059:
3023:
3011:
3007:
3003:
2999:
2995:
2991:
2981:heteropoly acid
2954:
2922:
2918:
2914:
2910:
2906:
2834:
2830:
2826:
2822:
2818:
2814:
2810:
2777:
2742:
2738:
2734:
2730:
2725:
2721:
2717:
2712:
2708:
2704:
2700:
2671:carbon monoxide
2659:
2646:
2564:
2443:
2413:such as water,
2376:
2354:
2342:
2316:
2312:
2301:
2294:monoprotic acid
2289:
2275:
2272:
2271:
2269:
2265:
2261:
2251:
2238:
2216:located at the
2212:and the former
2199:
2174:
2170:
2166:
2150:
2146:
2142:
2107:carbon monoxide
2084:calcium acetate
1913:
1904:
1900:
1882:
1878:
1874:
1870:
1866:
1862:
1858:
1854:
1850:
1832:
1824:
1820:
1816:
1804:
1800:
1738:
1651:carboxylic acid
1639:
1635:
1631:
1627:
1624:
1620:
1616:
1612:
1608:
1604:
1600:
1596:
1592:
1551:
1547:
1516:
1512:
1472:
1448:
1434:(preservatives)
1387:
1380:
1375:
1374:
1373: ?)
1364:
1360:
1356:
1352:
1328:Thioacetic acid
1326:
1322:
1318:
1314:
1310:
1308:Acetyl chloride
1306:
1302:
1298:
1294:
1288:
1278:
1272:
1254:
1241:
1228:
1207:
1199:
1193:
1181:
1175:
1145:
1142:
1124:
1123:
1122:
1121:
1114:
1107:
1100:
1096:
1088:
1057:
1039:
1025:
1004:
979:
931:
914:
911:
905:
901:
898:
897:Std enthalpy of
887:
884:
878:
874:
871:
870:Std enthalpy of
860:
857:
850:
847:
836:
829:
812:
802:
790:
784:
782:
764:
738:
721:
719:
715:
686:
626:
613:
609:
606:
592:
589:
584:
583:
572:
569:
568:
565:
559:
558:
547:
529:
522:
503:
483:
467:
454:
428:
401:
388:
376:
366:(preservatives)
352:
315:
295:
275:
255:
232:
215:
197:
184:
173:
160:
146:
138:
137:
126:
125:
35:
28:
23:
22:
15:
12:
11:
5:
10767:
10757:
10756:
10751:
10746:
10741:
10736:
10731:
10726:
10721:
10716:
10711:
10706:
10701:
10696:
10681:
10680:
10657:
10656:
10651:
10650:
10647:
10644:
10641:
10638:
10635:
10632:
10629:
10626:
10623:
10620:
10616:
10612:
10608:
10605:
10601:
10597:
10593:
10589:
10585:
10584:
10580:
10576:
10572:
10568:
10564:
10560:
10556:
10552:
10548:
10544:
10540:
10536:
10532:
10528:
10524:
10520:
10516:
10512:
10509:
10505:
10501:
10497:
10493:
10489:
10485:
10481:
10477:
10473:
10472:
10469:
10466:
10465:
10462:
10459:
10456:
10453:
10450:
10447:
10444:
10441:
10438:
10435:
10432:
10429:
10426:
10423:
10420:
10417:
10414:
10411:
10407:
10406:
10403:
10400:
10397:
10393:
10389:
10385:
10378:
10374:
10370:
10362:
10358:
10351:
10347:
10343:
10339:
10335:
10331:
10327:
10324:
10321:
10318:
10315:
10312:
10309:
10305:
10301:
10298:
10294:
10290:
10284:
10283:
10280:
10276:
10264:
10261:
10257:
10253:
10249:
10242:
10238:
10234:
10230:
10226:
10222:
10217:
10213:
10209:
10205:
10201:
10197:
10193:
10185:
10181:
10177:
10174:
10170:
10166:
10163:
10159:
10155:
10151:
10147:
10145:
10141:
10137:
10131:
10130:
10127:
10118:
10115:
10111:
10107:
10104:
10100:
10096:
10092:
10088:
10084:
10076:
10072:
10068:
10064:
10060:
10056:
10049:
10045:
10041:
10034:
10030:
10026:
10019:
10015:
10011:
10007:
10003:
9999:
9995:
9991:
9989:
9985:
9981:
9975:
9974:
9971:
9962:
9959:
9956:
9953:
9949:
9945:
9941:
9933:
9925:
9914:
9910:
9906:
9902:
9898:
9889:
9888:
9885:
9876:
9871:
9866:
9862:
9853:
9849:
9845:
9838:
9834:
9830:
9826:
9819:
9815:
9809:
9808:
9805:
9803:
9801:
9799:
9791:
9790:
9787:
9786:
9777:
9776:
9769:
9762:
9754:
9745:
9744:
9742:
9741:
9729:
9717:
9705:
9692:
9689:
9688:
9686:
9685:
9680:
9675:
9670:
9664:
9659:
9654:
9649:
9644:
9639:
9634:
9629:
9624:
9619:
9614:
9609:
9604:
9599:
9594:
9589:
9584:
9579:
9574:
9572:Cosmochemistry
9569:
9564:
9559:
9554:
9549:
9544:
9539:
9537:Astrochemistry
9534:
9529:
9523:
9521:
9515:
9514:
9512:
9511:
9506:
9501:
9496:
9491:
9487:
9483:
9478:
9474:
9469:
9464:
9459:
9454:
9449:
9443:
9441:
9435:
9434:
9432:
9431:
9426:
9421:
9417:
9412:
9407:
9402:
9397:
9392:
9390:Formyl radical
9387:
9382:
9376:
9370:
9368:
9360:
9359:
9356:
9355:
9353:
9352:
9347:
9342:
9337:
9332:
9327:
9322:
9320:Methyl acetate
9317:
9312:
9307:
9302:
9297:
9293:
9289:
9285:
9279:
9274:
9269:
9263:
9261:
9251:
9250:
9248:
9247:
9242:
9237:
9232:
9227:
9222:
9217:
9212:
9210:Dimethyl ether
9207:
9202:
9196:
9194:
9186:
9185:
9183:
9182:
9177:
9175:Methyl formate
9172:
9167:
9162:
9160:Glycolaldehyde
9157:
9152:
9147:
9142:
9136:
9134:
9126:
9125:
9123:
9122:
9117:
9112:
9107:
9102:
9097:
9095:Glycolonitrile
9092:
9090:Ethylene oxide
9087:
9082:
9081:
9080:
9070:
9064:
9062:
9054:
9053:
9051:
9050:
9045:
9040:
9035:
9030:
9025:
9020:
9015:
9010:
9006:
9001:
8996:
8991:
8989:Cyclopropenone
8986:
8981:
8976:
8970:
8968:
8960:
8959:
8957:
8956:
8951:
8946:
8941:
8936:
8931:
8926:
8921:
8916:
8911:
8906:
8901:
8896:
8891:
8889:Cyanoacetylene
8886:
8881:
8876:
8871:
8864:
8862:
8854:
8853:
8851:
8850:
8845:
8840:
8835:
8830:
8825:
8820:
8815:
8810:
8808:Methyl radical
8805:
8800:
8795:
8790:
8785:
8783:Isocyanic acid
8780:
8775:
8770:
8765:
8760:
8755:
8750:
8748:Isocyanic acid
8745:
8740:
8734:
8732:
8724:
8723:
8721:
8720:
8715:
8710:
8705:
8700:
8695:
8693:Sulfur dioxide
8690:
8685:
8680:
8675:
8670:
8668:Sodium cyanide
8665:
8660:
8655:
8650:
8645:
8640:
8635:
8630:
8626:
8621:
8616:
8611:
8606:
8601:
8596:
8591:
8585:
8579:
8577:Formyl radical
8574:
8569:
8564:
8559:
8554:
8549:
8544:
8539:
8537:Carbon dioxide
8534:
8529:
8524:
8518:
8516:
8510:
8509:
8484:
8482:
8480:
8479:
8474:
8469:
8464:
8459:
8454:
8449:
8444:
8439:
8434:
8429:
8424:
8418:
8413:
8408:
8402:
8397:
8392:
8387:
8385:Iron(II) oxide
8382:
8377:
8371:
8366:
8361:
8356:
8351:
8346:
8341:
8336:
8331:
8326:
8321:
8316:
8311:
8306:
8300:
8298:
8289:
8283:
8282:
8275:
8274:
8267:
8260:
8252:
8243:
8242:
8240:
8239:
8233:
8227:
8224:4-Hexadecenoic
8220:
8218:
8212:
8211:
8209:
8208:
8201:
8199:
8193:
8192:
8190:
8189:
8182:
8180:
8174:
8173:
8171:
8170:
8164:
8158:
8152:
8146:
8140:
8130:
8123:
8121:
8115:
8114:
8112:
8111:
8105:
8099:
8093:
8087:
8080:
8078:
8072:
8071:
8069:
8068:
8062:
8056:
8050:
8044:
8038:
8032:
8026:
8020:
8014:
8004:
7998:
7992:
7985:
7983:
7977:
7976:
7974:
7973:
7967:
7961:
7955:
7949:
7939:
7933:
7927:
7920:
7918:
7912:
7911:
7909:
7908:
7902:
7896:
7890:
7884:
7878:
7872:
7866:
7860:
7854:
7848:
7842:
7836:
7830:
7824:
7818:
7812:
7806:
7800:
7794:
7787:
7785:
7779:
7778:
7776:
7775:
7772:Tetracontanoic
7769:
7763:
7757:
7751:
7745:
7739:
7733:
7727:
7721:
7715:
7709:
7703:
7697:
7691:
7685:
7679:
7673:
7667:
7661:
7655:
7649:
7643:
7637:
7631:
7625:
7619:
7613:
7607:
7601:
7595:
7589:
7583:
7577:
7571:
7565:
7559:
7553:
7546:
7544:
7538:
7537:
7526:
7525:
7518:
7511:
7503:
7494:
7493:
7491:
7490:
7485:
7480:
7474:
7472:
7462:
7461:
7459:
7458:
7453:
7451:Hydrocortisone
7448:
7443:
7438:
7432:
7430:
7424:
7423:
7421:
7420:
7415:
7410:
7405:
7400:
7395:
7390:
7385:
7380:
7375:
7370:
7365:
7360:
7355:
7350:
7340:
7335:
7329:
7327:
7321:
7320:
7307:
7306:
7299:
7292:
7284:
7275:
7274:
7272:
7271:
7266:
7259:
7254:
7249:
7244:
7239:
7234:
7229:
7223:
7221:
7217:
7216:
7213:
7212:
7210:
7209:
7204:
7198:
7196:
7192:
7191:
7189:
7188:
7186:Amphotericin B
7183:
7178:
7172:
7170:
7164:
7163:
7161:
7160:
7154:
7152:
7146:
7145:
7143:
7142:
7137:
7132:
7127:
7122:
7117:
7112:
7107:
7102:
7097:
7092:
7087:
7082:
7077:
7072:
7066:
7064:
7055:
7049:
7048:
7046:
7045:
7039:
7037:
7031:
7030:
7028:
7027:
7022:
7017:
7011:
7009:
7003:
7002:
7000:
6999:
6994:
6992:Broxyquinoline
6989:
6984:
6982:Chlorquinaldol
6979:
6974:
6968:
6966:
6959:
6958:
6956:
6955:
6949:
6947:
6940:
6939:
6937:
6936:
6931:
6926:
6921:
6916:
6911:
6906:
6901:
6895:
6893:
6887:
6886:
6867:
6866:
6859:
6852:
6844:
6838:
6837:
6831:
6826:
6817:
6816:of acetic acid
6806:liquid density
6802:vapor pressure
6798:
6793:
6787:
6782:
6777:
6772:
6765:
6764:External links
6762:
6760:
6759:
6747:echa.europa.eu
6734:
6709:
6695:
6668:
6636:
6593:
6568:
6551:
6513:
6478:
6455:
6432:
6415:
6397:
6380:
6363:
6356:
6334:
6306:
6278:
6271:
6251:
6202:
6181:(6): 410–415.
6161:
6136:
6117:(5): 695–700.
6101:
6044:
5992:
5981:(5): 751–755.
5965:
5924:
5901:
5894:
5872:
5866:978-3527306732
5865:
5834:
5828:978-3527306732
5827:
5796:
5769:
5750:
5739:(5): 482–498.
5723:
5693:
5686:
5660:
5633:
5583:
5576:
5558:
5531:
5502:
5484:
5468:
5449:
5434:
5402:
5372:
5365:
5347:
5312:
5283:(9): 695–703.
5263:
5212:
5205:
5185:
5179:978-3527306732
5178:
5141:
5122:
5115:
5093:
5050:
5023:
4994:(7): 484–487.
4971:
4945:(2): 231–370.
4922:
4916:10.1086/310612
4878:
4871:
4842:
4830:
4811:
4800:on 29 May 2009
4780:(1/3): 14–23.
4760:
4727:
4708:
4682:
4675:
4651:
4636:
4629:
4611:
4604:
4586:
4574:
4552:
4528:
4516:
4502:
4495:
4466:
4457:
4442:
4440:
4437:
4435:
4434:
4425:
4415:
4413:
4410:
4409:
4408:
4403:
4396:
4393:
4382:
4381:
4372:
4360:
4357:
4353:
4352:
4347:
4340:
4337:
4333:
4332:
4327:
4320:
4317:
4313:
4312:
4307:
4305:GHS pictograms
4302:
4299:
4277:
4274:
4255:
4252:
4250:
4247:
4243:
4242:
4232:
4222:
4204:
4203:
4193:
4175:
4161:
4148:, used in the
4146:Sodium acetate
4138:
4135:
4107:
4106:
4101:
4097:
4093:
4089:
4085:
4077:sodium acetate
4045:
4044:
4040:
4036:
4032:
4028:
3991:
3988:
3987:
3986:
3981:
3977:
3973:
3969:
3965:
3961:
3957:
3941:carbon dioxide
3906:
3885:
3876:
3869:
3868:
3860:
3856:
3855:
3847:
3846:
3834:
3829:
3828:
3827:
3819:
3812:
3811:
3802:
3801:
3794:
3790:
3789:
3788:
3780:
3773:
3772:
3771:
3770:
3769:
3767:
3764:
3762:
3759:
3741:Main article:
3738:
3735:
3727:otitis externa
3690:Main article:
3687:
3684:
3618:protic solvent
3613:
3612:Use as solvent
3610:
3600:also used for
3596:, a synthetic
3586:
3585:
3580:
3576:
3572:
3568:
3564:
3560:
3555:
3551:
3547:
3543:
3522:
3519:
3510:ethylene oxide
3498:nitrocellulose
3482:
3481:
3476:
3472:
3468:
3464:
3460:
3456:
3452:
3432:
3431:
3427:, R = general
3422:
3418:
3414:
3398:propyl acetate
3361:
3358:
3338:
3337:
3332:
3328:
3324:
3320:
3316:
3312:
3308:
3280:
3277:
3264:
3261:
3225:
3224:
3219:
3215:
3211:
3207:
3195:carbon dioxide
3183:
3182:
3177:
3173:
3169:
3165:
3156:Acetobacterium
3140:
3137:
3083:
3082:
3077:
3073:
3069:
3065:
3061:
3022:
3019:
3015:
3014:
3009:
3005:
3001:
2997:
2993:
2962:Wacker process
2953:
2950:
2942:boiling points
2926:
2925:
2920:
2916:
2912:
2908:
2881:propionic acid
2838:
2837:
2832:
2828:
2824:
2820:
2816:
2812:
2776:
2773:
2754:Cativa process
2746:
2745:
2740:
2736:
2732:
2728:
2723:
2719:
2715:
2710:
2706:
2702:
2691:metal carbonyl
2683:
2682:
2658:
2655:
2588:methyl formate
2563:
2560:
2442:
2439:
2391:protic solvent
2375:
2372:
2358:hydrogen bonds
2353:
2350:
2319:). A 1.0
2314:
2305:conjugate base
2299:
2282:
2281:
2267:
2263:
2255:carboxyl group
2250:
2247:
2237:
2234:
2222:Sagittarius B2
2198:
2195:
2183:Cativa process
2172:
2168:
2148:
2144:
2052:, followed by
1989:lead poisoning
1944:lead carbonate
1912:
1909:
1902:
1880:
1876:
1868:
1860:
1852:
1818:
1809:conjugate base
1802:
1737:
1734:
1637:
1633:
1629:
1622:
1618:
1614:
1606:
1602:
1594:
1505:
1504:
1498:
1497:
1493:
1492:
1482:
1474:
1473:
1471:
1470:
1457:
1455:
1442:
1441:
1430:
1422:
1421:
1417:
1416:
1409:
1399:
1398:
1385:
1382:
1381:
1376:
1354:
1353:
1349:standard state
1346:
1343:
1342:
1336:
1335:
1331:
1330:
1324:Sodium acetate
1289:
1286:
1283:
1282:
1280:Propionic acid
1273:
1267:
1264:
1263:
1259:
1258:
1255:
1249:
1246:
1245:
1242:
1236:
1233:
1232:
1229:
1223:
1220:
1219:
1210:
1209:
1200:
1191:
1189:
1186:
1185:
1182:
1173:
1171:
1168:
1167:
1160:
1159:
1156:
1150:
1149:
1146:
1139:
1136:
1135:
1132:
1126:
1125:
1115:
1108:
1101:
1086:
1085:
1084:
1083:
1081:
1072:
1071:
1065:P305+P351+P338
1058:
1053:
1050:
1049:
1040:
1035:
1032:
1031:
1026:
1021:
1018:
1017:
1005:
1000:
997:
996:
986:
985:
981:
980:
978:
977:
963:
961:
955:
954:
932:
927:
924:
923:
919:
918:
915:
909:
903:
895:
892:
891:
888:
882:
876:
868:
865:
864:
861:
855:
844:
841:
840:
837:
825:
822:
821:
817:
816:
813:
808:
805:
804:
799:
793:
792:
788:
785:
780:
772:
769:
768:
765:
759:
756:
755:
750:
748:Conjugate base
744:
743:
740:
736:
726:
725:
712:
710:Vapor pressure
706:
705:
702:
693:
692:
687:
682:
679:
678:
675:
669:
668:
665:
659:
658:
655:
649:
648:
645:
639:
638:
635:
631:
630:
624:
618:
617:
611:
607:
602:
599:
598:
594:
593:
591:
590:
587:
579:
578:
577:
574:
573:
571:
570:
566:
563:
562:
554:
553:
552:
549:
548:
546:
545:
532:
530:
518:
515:
514:
511:
505:
504:
502:
501:
493:
491:
485:
484:
482:
481:
477:
475:
469:
468:
466:
465:
457:
455:
447:
444:
443:
436:
430:
429:
427:
426:
419:
411:
409:
403:
402:
400:
399:
391:
389:
384:
381:
380:
377:
372:
369:
368:
362:
354:
353:
351:
350:
346:
344:
336:
335:
325:
317:
316:
314:
313:
305:
303:
297:
296:
294:
293:
285:
283:
277:
276:
274:
273:
265:
263:
257:
256:
254:
253:
245:
243:
237:
236:
233:
228:
225:
224:
221:
220:Abbreviations
217:
216:
214:
213:
205:
203:
199:
198:
196:
195:
187:
185:
178:
175:
174:
172:
171:
163:
161:
156:
153:
152:
148:
147:
144:
140:
139:
135:
134:
128:
127:
123:
122:
116:
115:
111:
110:
102:
101:
98:
97:
87:
72:
71:
68:
67:
57:
26:
9:
6:
4:
3:
2:
10766:
10755:
10752:
10750:
10747:
10745:
10742:
10740:
10737:
10735:
10732:
10730:
10727:
10725:
10722:
10720:
10717:
10715:
10712:
10710:
10707:
10705:
10702:
10700:
10699:Acids in wine
10697:
10695:
10692:
10691:
10689:
10679:
10669:
10668:
10665:
10648:
10645:
10642:
10639:
10636:
10633:
10630:
10627:
10624:
10621:
10619:
10609:
10606:
10604:
10598:
10596:
10590:
10587:
10586:
10583:
10577:
10575:
10569:
10567:
10561:
10559:
10553:
10551:
10545:
10543:
10537:
10535:
10529:
10527:
10521:
10519:
10513:
10510:
10508:
10502:
10500:
10494:
10492:
10486:
10484:
10478:
10475:
10474:
10467:
10463:
10460:
10457:
10454:
10451:
10448:
10445:
10442:
10439:
10436:
10433:
10430:
10427:
10424:
10421:
10418:
10415:
10412:
10409:
10408:
10404:
10401:
10398:
10396:
10390:
10388:
10381:
10375:
10373:
10366:
10363:
10361:
10354:
10344:
10342:
10336:
10334:
10328:
10325:
10322:
10319:
10316:
10313:
10310:
10308:
10302:
10299:
10297:
10291:
10289:
10286:
10285:
10281:
10279:
10272:
10268:
10265:
10262:
10260:
10254:
10252:
10245:
10239:
10237:
10231:
10229:
10223:
10221:
10218:
10216:
10210:
10208:
10198:
10196:
10189:
10178:
10175:
10173:
10167:
10164:
10162:
10156:
10154:
10148:
10146:
10144:
10138:
10136:
10133:
10132:
10128:
10126:
10122:
10119:
10116:
10114:
10108:
10105:
10103:
10097:
10095:
10089:
10087:
10080:
10077:
10075:
10069:
10067:
10061:
10059:
10052:
10046:
10044:
10037:
10031:
10029:
10022:
10016:
10014:
10008:
10006:
10000:
9998:
9992:
9990:
9988:
9982:
9980:
9977:
9976:
9972:
9970:
9966:
9963:
9960:
9957:
9954:
9952:
9937:
9929:
9921:
9917:
9911:
9909:
9903:
9901:
9894:
9891:
9890:
9886:
9884:
9880:
9877:
9875:
9872:
9870:
9863:
9861:
9857:
9854:
9852:
9841:
9835:
9833:
9822:
9816:
9814:
9811:
9810:
9806:
9800:
9798:
9795:
9794:
9788:
9783:
9775:
9770:
9768:
9763:
9761:
9756:
9755:
9752:
9740:
9730:
9728:
9718:
9716:
9706:
9704:
9703:
9694:
9693:
9690:
9684:
9681:
9679:
9676:
9674:
9671:
9668:
9665:
9663:
9660:
9658:
9655:
9653:
9650:
9648:
9645:
9643:
9640:
9638:
9635:
9633:
9630:
9628:
9625:
9623:
9620:
9618:
9615:
9613:
9610:
9608:
9605:
9603:
9602:Homochirality
9600:
9598:
9595:
9593:
9590:
9588:
9585:
9583:
9580:
9578:
9575:
9573:
9570:
9568:
9565:
9563:
9560:
9558:
9555:
9553:
9550:
9548:
9545:
9543:
9540:
9538:
9535:
9533:
9530:
9528:
9525:
9524:
9522:
9520:
9516:
9510:
9507:
9505:
9502:
9500:
9497:
9495:
9492:
9490:
9484:
9482:
9475:
9473:
9470:
9468:
9465:
9463:
9460:
9458:
9457:Methoxyethane
9455:
9453:
9450:
9448:
9445:
9444:
9442:
9440:
9436:
9430:
9427:
9425:
9418:
9416:
9413:
9411:
9408:
9406:
9403:
9401:
9398:
9396:
9393:
9391:
9388:
9386:
9383:
9380:
9377:
9375:
9372:
9371:
9369:
9365:
9361:
9351:
9348:
9346:
9343:
9341:
9340:Butyronitrile
9338:
9336:
9333:
9331:
9328:
9326:
9323:
9321:
9318:
9316:
9315:Ethyl formate
9313:
9311:
9308:
9306:
9303:
9301:
9294:
9283:
9280:
9278:
9275:
9273:
9270:
9268:
9265:
9264:
9262:
9260:
9252:
9246:
9243:
9241:
9240:Propionitrile
9238:
9236:
9233:
9231:
9228:
9226:
9223:
9221:
9218:
9216:
9213:
9211:
9208:
9206:
9203:
9201:
9198:
9197:
9195:
9193:
9187:
9181:
9178:
9176:
9173:
9171:
9168:
9166:
9163:
9161:
9158:
9156:
9153:
9151:
9148:
9146:
9143:
9141:
9138:
9137:
9135:
9133:
9127:
9121:
9120:Vinyl alcohol
9118:
9116:
9113:
9111:
9108:
9106:
9103:
9101:
9098:
9096:
9093:
9091:
9088:
9086:
9083:
9079:
9078:Vinyl cyanide
9076:
9075:
9074:
9073:Acrylonitrile
9071:
9069:
9066:
9065:
9063:
9061:
9055:
9049:
9046:
9044:
9041:
9039:
9038:Pentynylidyne
9036:
9034:
9031:
9029:
9026:
9024:
9021:
9019:
9016:
9014:
9007:
9005:
9002:
9000:
8997:
8995:
8992:
8990:
8987:
8985:
8982:
8980:
8977:
8975:
8972:
8971:
8969:
8967:
8961:
8955:
8952:
8950:
8947:
8945:
8942:
8940:
8937:
8935:
8934:Methylenimine
8932:
8930:
8927:
8925:
8922:
8920:
8917:
8915:
8912:
8910:
8907:
8905:
8902:
8900:
8897:
8895:
8892:
8890:
8887:
8885:
8882:
8880:
8877:
8875:
8872:
8869:
8866:
8865:
8863:
8861:
8855:
8849:
8846:
8844:
8841:
8839:
8836:
8834:
8831:
8829:
8826:
8824:
8821:
8819:
8816:
8814:
8813:Propynylidyne
8811:
8809:
8806:
8804:
8803:Methyl cation
8801:
8799:
8796:
8794:
8791:
8789:
8786:
8784:
8781:
8779:
8776:
8774:
8771:
8769:
8766:
8764:
8763:Fulminic acid
8761:
8759:
8756:
8754:
8751:
8749:
8746:
8744:
8741:
8739:
8736:
8735:
8733:
8731:
8725:
8719:
8716:
8714:
8711:
8709:
8706:
8704:
8701:
8699:
8696:
8694:
8691:
8689:
8686:
8684:
8681:
8679:
8676:
8674:
8671:
8669:
8666:
8664:
8661:
8659:
8656:
8654:
8651:
8649:
8646:
8644:
8641:
8639:
8638:Nitrous oxide
8636:
8634:
8627:
8625:
8622:
8620:
8617:
8615:
8612:
8610:
8607:
8605:
8602:
8600:
8597:
8595:
8592:
8589:
8586:
8583:
8580:
8578:
8575:
8573:
8570:
8568:
8565:
8563:
8560:
8558:
8555:
8553:
8550:
8548:
8545:
8543:
8540:
8538:
8535:
8533:
8532:Amino radical
8530:
8528:
8525:
8523:
8520:
8519:
8517:
8515:
8511:
8506:
8497:
8488:
8478:
8475:
8473:
8470:
8468:
8465:
8463:
8462:Sodium iodide
8460:
8458:
8455:
8453:
8450:
8448:
8445:
8443:
8440:
8438:
8435:
8433:
8430:
8428:
8425:
8422:
8419:
8417:
8414:
8412:
8409:
8406:
8403:
8401:
8398:
8396:
8393:
8391:
8388:
8386:
8383:
8381:
8378:
8375:
8372:
8370:
8367:
8365:
8362:
8360:
8357:
8355:
8352:
8350:
8347:
8345:
8344:Cyano radical
8342:
8340:
8337:
8335:
8332:
8330:
8327:
8325:
8324:Carbon cation
8322:
8320:
8317:
8315:
8312:
8310:
8307:
8305:
8302:
8301:
8299:
8297:
8293:
8290:
8288:
8284:
8280:
8273:
8268:
8266:
8261:
8259:
8254:
8253:
8250:
8237:
8234:
8231:
8228:
8225:
8222:
8221:
8219:
8217:
8213:
8206:
8203:
8202:
8200:
8198:
8194:
8187:
8184:
8183:
8181:
8179:
8175:
8168:
8165:
8162:
8159:
8156:
8153:
8150:
8147:
8144:
8141:
8138:
8134:
8131:
8128:
8125:
8124:
8122:
8120:
8116:
8109:
8106:
8103:
8100:
8097:
8094:
8091:
8088:
8085:
8082:
8081:
8079:
8077:
8073:
8066:
8063:
8060:
8057:
8054:
8051:
8048:
8045:
8042:
8039:
8036:
8033:
8030:
8027:
8024:
8021:
8018:
8015:
8012:
8008:
8005:
8002:
7999:
7996:
7993:
7990:
7987:
7986:
7984:
7982:
7978:
7971:
7968:
7965:
7962:
7959:
7956:
7953:
7950:
7947:
7943:
7942:β-Eleostearic
7940:
7937:
7936:α-Eleostearic
7934:
7931:
7928:
7925:
7922:
7921:
7919:
7917:
7913:
7906:
7903:
7900:
7897:
7894:
7891:
7888:
7885:
7882:
7879:
7876:
7873:
7870:
7867:
7864:
7861:
7858:
7855:
7852:
7849:
7846:
7843:
7840:
7837:
7834:
7831:
7828:
7825:
7822:
7819:
7816:
7815:Laurolinoleic
7813:
7810:
7807:
7804:
7801:
7798:
7795:
7792:
7789:
7788:
7786:
7784:
7780:
7773:
7770:
7767:
7764:
7761:
7758:
7755:
7752:
7749:
7746:
7743:
7740:
7737:
7734:
7731:
7728:
7725:
7722:
7719:
7716:
7713:
7710:
7707:
7704:
7701:
7698:
7695:
7692:
7689:
7686:
7683:
7680:
7677:
7674:
7671:
7668:
7665:
7662:
7659:
7656:
7653:
7650:
7647:
7644:
7641:
7638:
7635:
7632:
7629:
7626:
7623:
7620:
7617:
7614:
7611:
7608:
7605:
7602:
7599:
7596:
7593:
7590:
7587:
7584:
7581:
7578:
7575:
7572:
7569:
7566:
7563:
7560:
7557:
7554:
7551:
7548:
7547:
7545:
7543:
7539:
7535:
7531:
7524:
7519:
7517:
7512:
7510:
7505:
7504:
7501:
7489:
7486:
7484:
7481:
7479:
7476:
7475:
7473:
7471:
7467:
7463:
7457:
7454:
7452:
7449:
7447:
7444:
7442:
7441:Dexamethasone
7439:
7437:
7436:Betamethasone
7434:
7433:
7431:
7429:
7425:
7419:
7416:
7414:
7411:
7409:
7406:
7404:
7401:
7399:
7398:Nitrofurazone
7396:
7394:
7391:
7389:
7386:
7384:
7381:
7379:
7376:
7374:
7371:
7369:
7368:Ciprofloxacin
7366:
7364:
7363:Chlorhexidine
7361:
7359:
7356:
7354:
7351:
7348:
7344:
7341:
7339:
7336:
7334:
7331:
7330:
7328:
7326:
7322:
7317:
7313:
7305:
7300:
7298:
7293:
7291:
7286:
7285:
7282:
7270:
7269:Copper usnate
7267:
7265:
7264:
7260:
7258:
7255:
7253:
7250:
7248:
7245:
7243:
7240:
7238:
7235:
7233:
7230:
7228:
7225:
7224:
7222:
7218:
7208:
7205:
7203:
7200:
7199:
7197:
7193:
7187:
7184:
7182:
7179:
7177:
7174:
7173:
7171:
7169:
7165:
7159:
7156:
7155:
7153:
7151:
7147:
7141:
7138:
7136:
7133:
7131:
7128:
7126:
7123:
7121:
7120:Propenidazole
7118:
7116:
7113:
7111:
7110:Fenticonazole
7108:
7106:
7103:
7101:
7098:
7096:
7093:
7091:
7088:
7086:
7083:
7081:
7078:
7076:
7073:
7071:
7070:Metronidazole
7068:
7067:
7065:
7063:
7059:
7056:
7054:
7050:
7044:
7043:Sulfatolamide
7041:
7040:
7038:
7036:
7032:
7026:
7025:Ascorbic acid
7023:
7021:
7018:
7016:
7013:
7012:
7010:
7008:
7007:Organic acids
7004:
6998:
6995:
6993:
6990:
6988:
6985:
6983:
6980:
6978:
6975:
6973:
6970:
6969:
6967:
6964:
6960:
6954:
6951:
6950:
6948:
6945:
6941:
6935:
6932:
6930:
6927:
6925:
6922:
6920:
6917:
6915:
6912:
6910:
6907:
6905:
6902:
6900:
6897:
6896:
6894:
6892:
6888:
6883:
6879:
6875:
6872:
6871:Gynecological
6865:
6860:
6858:
6853:
6851:
6846:
6845:
6842:
6836:
6832:
6830:
6827:
6825:
6821:
6818:
6815:
6811:
6807:
6803:
6799:
6797:
6794:
6791:
6788:
6786:
6783:
6781:
6778:
6776:
6773:
6771:
6768:
6767:
6748:
6744:
6738:
6719:
6713:
6705:
6699:
6688:
6681:
6680:
6672:
6653:
6646:
6640:
6632:
6628:
6624:
6620:
6616:
6612:
6608:
6604:
6597:
6579:
6572:
6564:
6563:
6555:
6547:
6543:
6539:
6535:
6531:
6527:
6523:
6517:
6509:
6505:
6501:
6497:
6493:
6489:
6482:
6474:
6470:
6466:
6459:
6451:
6447:
6444:: 1153–1155.
6443:
6436:
6428:
6427:
6419:
6411:
6407:
6401:
6390:
6384:
6373:
6367:
6359:
6357:9789251049495
6353:
6349:
6345:
6338:
6329:
6324:
6320:
6316:
6310:
6301:
6296:
6292:
6288:
6282:
6274:
6268:
6264:
6263:
6255:
6247:
6243:
6238:
6233:
6229:
6225:
6221:
6217:
6213:
6206:
6198:
6194:
6189:
6184:
6180:
6176:
6172:
6165:
6150:
6146:
6140:
6132:
6128:
6124:
6120:
6116:
6112:
6105:
6097:
6093:
6089:
6085:
6080:
6075:
6071:
6067:
6063:
6059:
6055:
6048:
6040:
6036:
6031:
6026:
6022:
6018:
6014:
6010:
6006:
5999:
5997:
5988:
5984:
5980:
5976:
5969:
5960:
5955:
5951:
5947:
5943:
5939:
5935:
5928:
5912:
5905:
5897:
5891:
5887:
5883:
5876:
5868:
5862:
5858:
5854:
5850:
5849:
5841:
5839:
5830:
5824:
5820:
5816:
5812:
5811:
5803:
5801:
5792:
5788:
5784:
5780:
5773:
5765:
5761:
5754:
5746:
5742:
5738:
5734:
5727:
5719:
5715:
5711:
5707:
5700:
5698:
5689:
5683:
5679:
5675:
5671:
5664:
5656:
5652:
5648:
5644:
5637:
5629:
5625:
5621:
5617:
5613:
5609:
5605:
5601:
5594:
5592:
5590:
5588:
5579:
5573:
5569:
5562:
5554:
5550:
5546:
5542:
5535:
5527:
5523:
5519:
5515:
5514:
5506:
5498:
5494:
5488:
5480:
5479:
5472:
5465:
5461:
5458:
5453:
5445:
5438:
5430:
5426:
5422:
5421:"Acetic Acid"
5415:
5413:
5411:
5409:
5407:
5398:
5394:
5390:
5386:
5379:
5377:
5368:
5362:
5358:
5351:
5343:
5339:
5335:
5331:
5327:
5323:
5316:
5308:
5304:
5299:
5294:
5290:
5286:
5282:
5278:
5274:
5267:
5259:
5255:
5250:
5245:
5240:
5235:
5231:
5227:
5223:
5216:
5208:
5202:
5198:
5197:
5189:
5181:
5175:
5171:
5167:
5163:
5162:
5154:
5152:
5150:
5148:
5146:
5137:
5133:
5126:
5118:
5112:
5107:
5106:
5097:
5089:
5085:
5081:
5077:
5073:
5069:
5065:
5061:
5054:
5046:
5042:
5038:
5034:
5027:
5019:
5015:
5010:
5005:
5001:
4997:
4993:
4989:
4982:
4975:
4964:
4960:
4956:
4952:
4948:
4944:
4940:
4933:
4926:
4917:
4912:
4908:
4904:
4900:
4896:
4892:
4885:
4883:
4874:
4868:
4864:
4859:
4858:
4849:
4847:
4839:
4834:
4826:
4822:
4815:
4799:
4795:
4791:
4787:
4783:
4779:
4775:
4771:
4764:
4753:
4749:
4745:
4738:
4731:
4723:
4720:(in French).
4719:
4712:
4704:
4700:
4699:
4691:
4689:
4687:
4678:
4672:
4668:
4664:
4663:
4655:
4647:
4640:
4632:
4626:
4622:
4615:
4607:
4601:
4597:
4590:
4584:
4578:
4570:
4566:
4562:
4561:"Acetic acid"
4556:
4548:
4544:
4537:
4535:
4533:
4525:
4520:
4512:
4506:
4498:
4492:
4488:
4484:
4480:
4476:
4470:
4461:
4453:
4447:
4443:
4429:
4420:
4416:
4407:
4406:Acids in wine
4404:
4402:
4399:
4398:
4392:
4390:
4373:
4370:
4365:
4361:
4358:
4355:
4354:
4348:
4345:
4341:
4338:
4335:
4334:
4328:
4325:
4321:
4318:
4315:
4314:
4311:
4308:
4306:
4303:
4300:
4296:
4295:Concentration
4293:
4292:
4289:
4287:
4283:
4273:
4270:
4264:
4262:
4246:
4240:
4236:
4233:
4230:
4226:
4223:
4220:
4216:
4212:
4209:
4208:
4207:
4201:
4200:Heck reaction
4197:
4194:
4191:
4187:
4183:
4179:
4176:
4173:
4169:
4165:
4162:
4159:
4155:
4151:
4147:
4144:
4143:
4142:
4134:
4132:
4128:
4127:cacodyl oxide
4124:
4120:
4116:
4112:
4082:
4081:
4080:
4078:
4074:
4070:
4066:
4062:
4058:
4054:
4050:
4025:
4024:
4023:
4021:
4017:
4013:
4009:
4005:
4001:
3997:
3970:
3954:
3953:
3952:
3950:
3946:
3942:
3938:
3934:
3930:
3926:
3925:loss of water
3922:
3918:
3914:
3902:
3898:
3894:
3880:
3874:
3873:
3851:
3843:
3839:
3823:
3817:
3816:
3806:
3798:
3784:
3778:
3777:
3758:
3755:
3752:, and in the
3751:
3744:
3734:
3732:
3728:
3723:
3721:
3720:iontophoresis
3716:
3712:
3710:
3706:
3702:
3697:
3693:
3683:
3681:
3677:
3672:
3671:carbocation.
3670:
3666:
3662:
3658:
3654:
3650:
3646:
3642:
3637:
3635:
3631:
3627:
3623:
3619:
3609:
3607:
3603:
3599:
3595:
3591:
3561:
3540:
3539:
3538:
3536:
3532:
3528:
3518:
3515:
3511:
3507:
3503:
3499:
3495:
3491:
3487:
3484:Most acetate
3455:COO−H + HO−CH
3449:
3448:
3447:
3445:
3441:
3440:ethyl acetate
3437:
3430:
3411:
3410:
3409:
3407:
3403:
3399:
3395:
3391:
3390:butyl acetate
3387:
3383:
3382:ethyl acetate
3379:
3375:
3371:
3367:
3357:
3355:
3351:
3347:
3343:
3305:
3304:
3303:
3301:
3298:
3294:
3290:
3286:
3285:vinyl acetate
3276:
3274:
3270:
3260:
3258:
3254:
3250:
3246:
3242:
3238:
3234:
3230:
3204:
3203:
3202:
3200:
3196:
3192:
3188:
3162:
3161:
3160:
3158:
3157:
3152:
3151:
3146:
3136:
3134:
3129:
3127:
3123:
3119:
3113:
3111:
3107:
3103:
3099:
3094:
3092:
3088:
3058:
3057:
3056:
3054:
3050:
3046:
3042:
3038:
3034:
3030:
3029:
3018:
2990:
2989:
2988:
2986:
2982:
2978:
2974:
2970:
2965:
2963:
2959:
2949:
2947:
2943:
2939:
2935:
2931:
2930:ethyl acetate
2905:
2904:
2903:
2901:
2897:
2893:
2889:
2884:
2882:
2878:
2874:
2873:ethyl acetate
2870:
2865:
2860:
2858:
2854:
2850:
2846:
2843:
2809:
2808:
2807:
2805:
2801:
2797:
2793:
2788:
2786:
2782:
2772:
2770:
2765:
2763:
2759:
2755:
2751:
2729:
2716:
2699:
2698:
2697:
2695:
2692:
2688:
2680:
2676:
2675:
2674:
2672:
2668:
2664:
2663:carbonylation
2654:
2650:
2645:
2641:
2637:
2633:
2629:
2625:
2621:
2616:
2612:
2608:
2603:
2601:
2597:
2593:
2589:
2585:
2581:
2580:carbonylation
2577:
2568:
2559:
2557:
2556:antibacterial
2553:
2549:
2545:
2541:
2537:
2533:
2529:
2528:
2523:
2522:
2517:
2513:
2508:
2506:
2502:
2498:
2494:
2490:
2486:
2485:triglycerides
2482:
2478:
2474:
2473:carbohydrates
2470:
2466:
2462:
2458:
2455:
2450:
2448:
2438:
2436:
2432:
2428:
2424:
2420:
2416:
2412:
2408:
2404:
2400:
2396:
2393:, similar to
2392:
2388:
2384:
2380:
2371:
2368:
2363:
2359:
2345:
2339:
2335:
2333:
2328:
2326:
2322:
2310:
2306:
2302:
2295:
2287:
2260:
2259:
2258:
2256:
2242:
2233:
2231:
2227:
2223:
2219:
2215:
2211:
2208:array at the
2207:
2203:
2194:
2192:
2188:
2184:
2180:
2164:
2160:
2156:
2140:
2136:
2132:
2128:
2124:
2120:
2116:
2112:
2111:Henri Dreyfus
2108:
2104:
2101:Because both
2099:
2097:
2093:
2089:
2088:sulfuric acid
2085:
2081:
2077:
2072:
2070:
2067:
2063:
2059:
2055:
2051:
2047:
2043:
2039:
2035:
2032:
2031:Hermann Kolbe
2023:
2019:
2017:
2013:
2009:
2005:
2001:
1997:
1992:
1990:
1986:
1985:
1979:
1978:sugar of lead
1975:
1971:
1967:
1963:
1959:
1955:
1951:
1950:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1917:
1908:
1899:
1895:
1890:
1888:
1848:
1844:
1840:
1835:
1830:
1814:
1810:
1799:
1796:
1792:
1788:
1783:
1780:
1776:
1771:
1769:
1765:
1764:
1759:
1755:
1751:
1747:
1743:
1733:
1731:
1727:
1726:carbonylation
1723:
1722:metric tonnes
1718:
1716:
1712:
1711:carbohydrates
1708:
1704:
1700:
1696:
1692:
1688:
1684:
1683:food industry
1680:
1676:
1672:
1668:
1664:
1660:
1656:
1652:
1647:
1644:
1591:
1587:
1581:
1546:
1545:ethanoic acid
1540:
1511:
1503:
1499:
1494:
1490:
1486:
1483:
1481:
1479:ECHA InfoCard
1475:
1467:
1463:
1462:DTXSID5024394
1459:
1458:
1456:
1447:
1443:
1439:
1435:
1431:
1429:
1423:
1418:
1414:
1410:
1408:
1404:
1400:
1397:Clinical data
1395:
1379:
1372:
1367:
1350:
1344:
1341:
1337:
1332:
1329:
1325:
1321:
1317:
1316:Ethyl acetate
1313:
1312:Glycolic acid
1309:
1305:
1301:
1297:
1293:
1290:
1285:
1284:
1281:
1277:
1274:
1271:
1266:
1265:
1260:
1256:
1252:
1248:
1247:
1243:
1240:(Recommended)
1239:
1235:
1234:
1230:
1227:(Permissible)
1226:
1222:
1221:
1217:
1216:
1211:
1205:
1201:
1197:
1188:
1187:
1183:
1179:
1170:
1169:
1165:
1161:
1157:
1155:
1152:
1151:
1147:
1144:
1138:
1137:
1133:
1131:
1128:
1127:
1120:
1113:
1106:
1082:
1079:
1078:
1074:
1073:
1059:
1056:
1052:
1051:
1041:
1038:
1034:
1033:
1030:
1027:
1024:
1020:
1019:
1015:
1010:
1006:
1003:
999:
998:
994:
992:
987:
982:
975:
965:
964:
962:
960:
957:
956:
951:
946:
941:
936:
933:
930:
926:
925:
922:Pharmacology
920:
916:
908:
900:
894:
893:
889:
881:
873:
867:
866:
862:
854:
849:
843:
842:
838:
833:
828:
827:Heat capacity
824:
823:
818:
814:
811:
810:Dipole moment
807:
806:
800:
798:
795:
794:
786:
779:
775:
771:
770:
766:
762:
758:
757:
754:
751:
749:
746:
745:
741:
735:
731:
728:
727:
713:
711:
708:
707:
703:
701:
700:
695:
694:
691:
688:
685:
681:
680:
676:
674:
673:Boiling point
671:
670:
666:
664:
663:Melting point
661:
660:
656:
654:
651:
650:
646:
644:
641:
640:
636:
633:
632:
625:
623:
620:
619:
608:
605:
601:
600:
595:
586:
585:
582:
575:
561:
560:
557:
550:
542:
538:
537:DTXSID5024394
534:
533:
531:
521:
517:
516:
512:
510:
507:
506:
499:
495:
494:
492:
490:
487:
486:
479:
478:
476:
474:
471:
470:
463:
459:
458:
456:
450:
446:
445:
441:
437:
435:
432:
431:
424:
420:
417:
413:
412:
410:
408:
405:
404:
397:
393:
392:
390:
387:
383:
382:
378:
375:
371:
370:
367:
363:
361:
356:
355:
348:
347:
345:
343:
338:
337:
333:
329:
326:
324:
322:ECHA InfoCard
319:
318:
311:
307:
306:
304:
302:
299:
298:
291:
287:
286:
284:
282:
279:
278:
271:
267:
266:
264:
262:
259:
258:
251:
247:
246:
244:
242:
239:
238:
234:
231:
227:
226:
222:
219:
218:
211:
207:
206:
204:
201:
200:
193:
189:
188:
186:
182:
177:
176:
169:
165:
164:
162:
159:
155:
154:
149:
141:
136:Ethanoic acid
133:
129:
121:
117:
112:
108:
103:
92:
88:
82:
78:
77:
73:
62:
58:
52:
48:
47:
43:
37:
33:
19:
10694:Acetic acids
9796:
9695:
9678:Spectroscopy
9532:Astrobiology
9385:Formaldehyde
9277:Benzonitrile
9139:
9068:Acetaldehyde
9023:Methanethiol
8974:Acetonitrile
8879:Carbodiimide
8758:Formaldehyde
8753:Cyanoethynyl
8604:Iron cyanide
8599:Hydroperoxyl
8400:Nitric oxide
8236:8-Eicosenoic
8230:Petroselinic
8136:
8010:
8007:Linolelaidic
7945:
7887:Clupanodonic
7845:Palmitidonic
7682:Pentacosylic
7658:Heneicosylic
7622:Pentadecylic
7456:Prednisolone
7418:Tetracycline
7332:
7261:
7247:Furazolidone
7237:Policresulen
7140:Flutrimazole
7125:Butoconazole
7105:Ketoconazole
7075:Clotrimazole
7035:Sulfonamides
7019:
6997:Oxyquinoline
6750:. Retrieved
6746:
6737:
6725:. Retrieved
6712:
6698:
6687:the original
6678:
6671:
6659:. Retrieved
6652:the original
6639:
6606:
6602:
6596:
6584:. Retrieved
6571:
6561:
6554:
6529:
6525:
6516:
6491:
6487:
6481:
6464:
6458:
6441:
6435:
6425:
6418:
6409:
6400:
6383:
6366:
6343:
6337:
6328:10665/345533
6318:
6309:
6300:10665/325771
6290:
6281:
6261:
6254:
6219:
6215:
6205:
6178:
6174:
6164:
6152:. Retrieved
6148:
6139:
6114:
6110:
6104:
6061:
6057:
6047:
6012:
6008:
5978:
5974:
5968:
5944:(305): 512.
5941:
5937:
5927:
5915:. Retrieved
5904:
5885:
5875:
5846:
5808:
5782:
5778:
5772:
5763:
5759:
5753:
5736:
5732:
5726:
5709:
5705:
5669:
5663:
5646:
5642:
5636:
5606:(1): 55–60.
5603:
5599:
5567:
5561:
5544:
5540:
5534:
5520:(1): 73–91.
5517:
5511:
5505:
5496:
5487:
5477:
5471:
5452:
5443:
5437:
5429:the original
5424:
5388:
5384:
5356:
5350:
5325:
5321:
5315:
5280:
5276:
5266:
5229:
5225:
5215:
5195:
5188:
5159:
5135:
5131:
5125:
5104:
5096:
5063:
5059:
5053:
5036:
5032:
5026:
4991:
4987:
4974:
4963:the original
4942:
4938:
4925:
4898:
4894:
4856:
4833:
4820:
4814:
4802:. Retrieved
4798:the original
4777:
4773:
4763:
4752:the original
4747:
4743:
4730:
4721:
4717:
4711:
4697:
4661:
4654:
4645:
4639:
4620:
4614:
4595:
4589:
4577:
4564:
4555:
4523:
4519:
4505:
4474:
4469:
4460:
4451:
4446:
4428:
4419:
4385:
4279:
4265:
4257:
4244:
4205:
4166:, used as a
4154:preservative
4140:
4108:
4065:polyethylene
4046:
3993:
3890:
3870:
3814:
3813:
3774:
3746:
3724:
3717:
3713:
3698:
3695:
3673:
3667:to trap the
3641:carbocations
3638:
3615:
3587:
3527:condensation
3524:
3490:acetaldehyde
3483:
3433:
3385:
3363:
3339:
3327:C−CO−O−CH=CH
3311:C−COOH + 2 C
3282:
3266:
3256:
3252:
3248:
3244:
3240:
3236:
3232:
3228:
3226:
3184:
3154:
3148:
3142:
3130:
3114:
3100:process. If
3095:
3086:
3084:
3026:
3024:
3016:
2966:
2955:
2946:distillation
2938:formaldehyde
2927:
2900:acetaldehyde
2885:
2864:temperatures
2861:
2839:
2789:
2781:acetaldehyde
2778:
2766:
2747:
2705:OH + HI → CH
2684:
2660:
2604:
2576:fermentation
2573:
2525:
2519:
2509:
2451:
2444:
2441:Biochemistry
2377:
2355:
2343:
2329:
2283:
2252:
2202:Interstellar
2200:
2138:
2121:needed (200
2100:
2080:milk of lime
2073:
2066:electrolytic
2042:chlorination
2028:
1993:
1981:
1977:
1974:lead acetate
1965:
1947:
1939:
1932:Theophrastus
1914:
1891:
1784:
1772:
1742:trivial name
1739:
1736:Nomenclature
1719:
1699:acetyl group
1695:biochemistry
1648:
1544:
1509:
1508:
1292:Acetaldehyde
1214:
1163:
1141:Autoignition
1076:
1028:
990:
959:Legal status
906:
879:
852:
831:
777:
733:
698:
473:RTECS number
151:Identifiers
143:Other names
40:Acetic acid
36:
10729:Otologicals
10704:Antiseptics
9652:Outer space
9562:Cosmic dust
9527:Abiogenesis
9439:Unconfirmed
9395:Heavy water
9235:Ethanethiol
9150:Cyanoallene
9140:Acetic acid
9110:Methylamine
8994:Diacetylene
8909:Formic acid
8899:Cyanomethyl
8557:Diazenylium
8547:CCP radical
8423:(molecular)
8407:(molecular)
8376:(molecular)
8084:Palmitoleic
8053:Arachidonic
8017:γ-Linolenic
7924:Myristoleic
7863:α-Parinaric
7857:Stearidonic
7851:α-Linolenic
7803:Decadienoic
7742:Ceroplastic
7706:Nonacosylic
7646:Nonadecylic
7534:fatty acids
7470:anesthetics
7408:Polymyxin B
7333:Acetic acid
7158:Terconazole
7135:Oxiconazole
7130:Omoconazole
7115:Azanidazole
7100:Tioconazole
7095:Isoconazole
7053:Antifungals
7020:Acetic acid
7015:Lactic acid
6987:Dequalinium
6965:derivatives
6929:Clindamycin
6924:Mepartricin
6919:Carfecillin
6891:Antibiotics
6878:antiseptics
6752:13 December
6727:19 February
6679:Acetic Acid
5909:Felgner A.
5760:Enzymologia
5457:Acetic Acid
4423:= 10 = 0.4%
4269:lacrimation
4073:baking soda
4053:passivating
3951:and water:
3815:acetic acid
3686:Medical use
3665:nucleophile
3651:involves a
3616:As a polar
3590:acetylation
3429:alkyl group
3257:Clostridium
3253:Acetobacter
3249:Acetobacter
3245:Clostridium
3241:Acetobacter
3237:Clostridium
3235:. However,
3233:Acetobacter
3229:Clostridium
3150:Clostridium
3143:Species of
3087:Acetobacter
3033:apple cider
3028:Acetobacter
2969:Showa Denko
2934:formic acid
2877:formic acid
2842:naphthenate
2722:I + CO → CH
2687:iodomethane
2647: [
2615:precipitate
2521:Acetobacter
2481:fatty acids
2431:miscibility
2383:hydrophilic
2167:[Ir(CO)
2143:[Rh(CO)
2034:synthesised
2016:Pierre Adet
1689:E260 as an
1655:formic acid
1510:Acetic acid
1485:100.000.528
1420:Identifiers
1391:Acetic acid
1276:Formic acid
1178:median dose
1164:Lethal dose
1143:temperature
1130:Flash point
1023:Signal word
801:1.22 mPa s
634:Appearance
597:Properties
440:Acetic+acid
328:100.000.528
250:CHEBI:15366
124:Acetic acid
18:Acetic Acid
10688:Categories
9567:Cosmic ray
9509:Silylidyne
9472:Hemolithin
9447:Anthracene
9364:Deuterated
9345:Pyrimidine
9155:Ethanimine
9018:Ketenimine
8874:Butadiynyl
8698:Thioformyl
8552:Chloronium
7694:Carboceric
7676:Lignoceric
7670:Tricosylic
7610:Tridecylic
7586:Pelargonic
7466:Analgesics
7388:Miconazole
7378:Gentamicin
7373:Clioquinol
7353:Boric acid
7257:Protiofate
7227:Clodantoin
7202:Ciclopirox
7090:Ornidazole
7080:Miconazole
7062:Imidazoles
6977:Clioquinol
6934:Pentamycin
6909:Hachimycin
6899:Candicidin
6609:(7): 353.
4901:(1): L71.
4804:12 October
4724:: 299–319.
4526:, 10th ed.
4439:References
4298:by weight
4219:indigo dye
4131:malodorous
4096:COONa + CO
4031:COOH → (CH
4014:, forming
4002:including
3833:Li[AlH
3669:rearranged
3643:, such as
3575:=C=O → (CH
3492:using the
3364:The major
3218:COOH + 2 H
3187:acetogenic
3126:convection
3098:winemaking
2611:impurities
2562:Production
2550:and other
2532:foodstuffs
2489:acetyl-CoA
2469:metabolism
2461:coenzyme A
2415:chloroform
2236:Properties
2096:indigo dye
1998:alchemist
1960:. Ancient
1940:white lead
1770:" itself.
1707:metabolism
1703:coenzyme A
1002:Pictograms
899:combustion
714:1.54653947
622:Molar mass
498:Q40Q9N063P
386:IUPHAR/BPS
281:ChemSpider
179:3D model (
158:CAS Number
9499:Phosphine
9367:molecules
9300:fullerene
9200:Acetamide
9004:Formamide
8884:Cyanamide
8738:Acetylene
8713:Tricarbon
8624:Methylene
8609:Isoformyl
8514:Triatomic
8287:Molecules
8102:Paullinic
8047:Sciadonic
8029:Pinolenic
7809:Lauroleic
7724:Lacceroic
7652:Arachidic
7598:Undecylic
7550:Propionic
7542:Saturated
7488:Phenazone
7478:Lidocaine
7413:Rifamycin
7403:Ofloxacin
7325:Infection
7242:Nifuratel
7181:Natamycin
7150:Triazoles
7085:Econazole
6963:Quinoline
6953:Acetarsol
6946:compounds
6631:0021-9584
6546:1938-159X
6526:Corrosion
6508:0002-7863
6154:15 August
6015:: h3084.
5620:1384-6574
5541:Synthesis
5196:Chemistry
4310:H-Phrases
4301:Molarity
4282:corrosive
4184:—used as
4172:fungicide
4133:vapours.
4092:COOH → CH
4049:aluminium
4027:Mg + 2 CH
4008:magnesium
3996:corrosive
3976:COOH → CH
3960:COOH → CH
3921:anhydride
3761:Reactions
3750:condiment
3421:COO−R + H
3402:catalyzed
3354:adhesives
3344:or other
3297:palladium
2977:palladium
2888:catalysts
2849:manganese
2796:peroxides
2743:COOH + HI
2501:triacetin
2401:. With a
2352:Structure
2266:COOH ⇌ CH
2119:pressures
2069:reduction
2054:pyrolysis
2006:from the
1982:sugar of
1949:verdigris
1905:−C(=O)−OH
1863:−C(=O)−OH
1785:A common
1775:anhydrous
1756:word for
1681:. In the
1673:for wood
1588:with the
1496:Data page
1413:Monograph
1407:Drugs.com
1296:Acetamide
993:labelling
872:formation
846:Std molar
797:Viscosity
791:= 18.19)
509:UN number
480:AF1225000
349:200-580-7
341:EC Number
270:ChEMBL539
10739:Solvents
10678:Medicine
9897:NaH(OAc)
9486:Linear C
9467:Graphene
9379:Ammonium
9180:Acrolein
9043:Propynal
9028:Methanol
8999:Ethylene
8868:Ammonium
8643:Nitroxyl
8467:Sulfanyl
8411:Imidogen
8405:Nitrogen
8374:Hydrogen
8319:Argonium
8296:Diatomic
8205:Gadoleic
8186:Sapienic
8155:Nervonic
8090:Vaccenic
8023:Calendic
8001:Linoleic
7797:Decenoic
7791:Octenoic
7712:Melissic
7700:Montanic
7634:Margaric
7628:Palmitic
7616:Myristic
7580:Caprylic
7574:Enanthic
7393:Neomycin
7176:Nystatin
7168:Polyenes
6467:: 2877.
6346:. Rome:
6317:(2021).
6289:(2019).
6246:27283591
6197:23999348
6131:19286325
6088:25851059
6039:26142020
5938:Br Med J
5628:93855717
5460:Archived
5342:14555416
5307:31160120
5258:16788062
5088:16839071
4571:(NIOSH).
4549:(NIOSH).
4395:See also
4356:>90%
4276:Solution
4186:mordants
4051:forms a
4047:Because
4020:acetates
4016:hydrogen
3980:=C=O + H
3754:pickling
3657:camphene
3554:=C=O + H
3378:coatings
3346:polymers
3300:catalyst
3289:ethylene
3199:hydrogen
3118:charcoal
3076:COOH + H
2983:such as
2960:via the
2958:ethylene
2869:butanone
2857:chromium
2694:catalyst
2667:methanol
2620:Celanese
2596:ethylene
2584:methanol
2552:primates
2512:excreted
2505:glycerol
2497:pyruvate
2427:miscible
2411:solvents
2367:enthalpy
2103:methanol
1936:pigments
1847:actinium
1730:methanol
1427:E number
1268:Related
1077:NFPA 704
984:Hazards
929:ATC code
803:1.22 cP
787:1.371 (V
763:(χ)
690:Miscible
359:E number
301:DrugBank
10719:Flavors
10600:Th(OAc)
10592:Ac(OAc)
10579:Yb(OAc)
10571:Tm(OAc)
10563:Er(OAc)
10555:Ho(OAc)
10547:Dy(OAc)
10539:Tb(OAc)
10531:Gd(OAc)
10523:Eu(OAc)
10515:Sm(OAc)
10504:Nd(OAc)
10496:Pr(OAc)
10488:Ce(OAc)
10480:La(OAc)
10471:
10392:Bi(OAc)
10384:Pb(OAc)
10377:Pb(OAc)
10369:Tl(OAc)
10357:Hg(OAc)
10338:Au(OAc)
10330:Pt(OAc)
10304:Lu(OAc)
10293:Ba(OAc)
10256:Sb(OAc)
10248:Sn(OAc)
10241:Sn(OAc)
10233:In(OAc)
10225:Cd(OAc)
10212:Pd(OAc)
10192:Ru(OAc)
10169:Mo(OAc)
10158:Zr(OAc)
10140:Sr(OAc)
10110:As(OAc)
10099:Ga(OAc)
10091:Zn(OAc)
10083:Cu(OAc)
10071:Ni(OAc)
10063:Co(OAc)
10055:Fe(OAc)
10048:Fe(OAc)
10040:Mn(OAc)
10033:Mn(OAc)
10025:Cr(OAc)
10018:Cr(OAc)
10010:VO(OAc)
10002:Ti(OAc)
9994:Sc(OAc)
9984:Ca(OAc)
9924:Al(OAc)
9913:Al(OAc)
9905:Mg(OAc)
9818:Be(OAc)
9782:acetate
9632:Kerogen
9519:Related
9462:Glycine
9415:Propyne
9374:Ammonia
9272:Benzene
9267:Acetone
9259:or more
9230:Propene
9215:Ethanol
9105:Propyne
8924:Methane
8793:Ketenyl
8743:Ammonia
8143:Gondoic
8133:Elaidic
8096:Rumenic
8059:Adrenic
7952:Punicic
7730:Psyllic
7688:Cerotic
7664:Behenic
7640:Stearic
7568:Caproic
7562:Valeric
7556:Butyric
7483:Cocaine
7232:Inosine
6944:Arsenic
6822:in the
6611:Bibcode
6237:8570637
6096:4767974
6079:7949569
6030:4490835
5987:9571976
5959:2310334
5917:27 July
5674:Bibcode
5298:6699882
5249:1502439
5068:Bibcode
4996:Bibcode
4947:Bibcode
4903:Bibcode
4863:262–266
4794:3179569
4543:"#0002"
4336:25–90%
4316:10–25%
4286:aqueous
4168:pigment
4150:textile
3945:methane
3919:; this
3897:acetate
3872:ethanol
3743:Vinegar
3649:camphor
3626:solvent
3598:textile
3506:varnish
3436:ethanol
3406:alcohol
3295:over a
3273:monomer
3269:reagent
3133:culture
2911:CHO + O
2831:H + 2 H
2792:naphtha
2758:greener
2735:COI + H
2640:Eastman
2636:Samsung
2600:ethanol
2558:agent.
2493:ethanol
2447:acetate
2395:ethanol
2309:acetate
2249:Acidity
2191:greener
2187:iridium
2179:iridium
2135:rhodium
2004:acetone
1928:alchemy
1916:Vinegar
1911:History
1855:−C(O)OH
1813:acetate
1805:−C(=O)−
1758:vinegar
1653:(after
1643:Vinegar
1371:what is
1369: (
1257:50 ppm
947: (
945:S02AA10
943:)
937: (
935:G01AD02
848:entropy
815:1.74 D
753:Acetate
730:Acidity
653:Density
616:
588:CC(O)=O
449:PubChem
310:DB03166
235:506007
168:64-19-7
32:Ascetic
10664:Portal
10275:I(OAc)
10150:Y(OAc)
9932:Al(OH)
9848:O(OAc)
9837:B(OAc)
9829:O(OAc)
9683:Tholin
9504:Pyrene
8949:Silane
8919:Ketene
8421:Oxygen
8238:(20:1)
8232:(18:1)
8226:(16:1)
8207:(20:1)
8188:(16:1)
8169:(20:3)
8163:(20:2)
8157:(24:1)
8151:(22:1)
8149:Erucic
8145:(20:1)
8139:-18:1)
8129:(18:1)
8110:(20:3)
8104:(20:1)
8098:(18:2)
8092:(18:1)
8086:(16:1)
8067:(22:5)
8065:Osbond
8061:(22:4)
8055:(20:4)
8049:(20:3)
8043:(20:3)
8037:(20:2)
8031:(18:3)
8025:(18:3)
8019:(18:3)
8013:-18:2)
8003:(18:2)
7997:(18:1)
7991:(14:1)
7972:(20:4)
7966:(20:3)
7960:(18:3)
7954:(18:3)
7948:-18:3)
7938:(18:3)
7932:(16:1)
7926:(14:1)
7907:(24:6)
7901:(24:5)
7895:(22:6)
7889:(22:5)
7883:(20:5)
7877:(20:4)
7871:(20:3)
7865:(18:4)
7859:(18:4)
7853:(18:3)
7847:(16:4)
7841:(16:3)
7835:(14:3)
7829:(14:2)
7823:(14:1)
7817:(12:2)
7811:(12:1)
7805:(10:2)
7799:(10:1)
7736:Geddic
7604:Lauric
7592:Capric
7530:Lipids
6629:
6586:5 June
6544:
6506:
6354:
6269:
6244:
6234:
6195:
6129:
6094:
6086:
6076:
6037:
6027:
5985:
5956:
5892:
5863:
5825:
5766:: 369.
5684:
5626:
5618:
5574:
5363:
5340:
5305:
5295:
5256:
5246:
5203:
5176:
5113:
5086:
4869:
4792:
4673:
4627:
4602:
4493:
4254:Vapour
4170:and a
4039:Mg + H
4010:, and
4000:metals
3949:ketene
3937:amides
3935:, and
3929:Esters
3709:cervix
3606:heroin
3571:H + CH
3550:H → CH
3535:ketene
3486:esters
3467:COO−CH
3438:gives
3396:, and
3374:paints
3366:esters
3350:paints
3293:oxygen
3185:These
3176:→ 3 CH
3110:grapes
3091:oxygen
3068:OH + O
3053:potato
2936:, and
2915:→ 2 CH
2892:oxygen
2879:, and
2855:, and
2853:cobalt
2823:→ 4 CH
2804:butane
2790:Light
2739:O → CH
2642:, and
2592:syngas
2548:humans
2538:, and
2454:acetyl
2423:octane
2419:hexane
2417:, and
2407:sugars
2379:Liquid
2362:dimers
2286:proton
2185:, the
2127:cobalt
1996:German
1984:Saturn
1962:Romans
1954:copper
1946:) and
1894:methyl
1873:, and
1807:; the
1795:acetyl
1787:symbol
1779:German
1763:acetum
1697:, the
1366:verify
1363:
1158:4–16%
1029:Danger
972:
742:4.756
722:
716:
704:−0.28
627:60.052
581:SMILES
423:D00010
416:C00033
261:ChEMBL
210:B00009
202:3DMet
114:Names
10615:(OAc)
10365:TlOAc
10350:(OAc)
10288:CsOAc
10220:AgOAc
10204:(OAc)
10184:(OAc)
10135:RbOAc
10125:BrOAc
10079:CuOAc
9969:ClOAc
9948:(OAc)
9920:ALSOL
9893:NaOAc
9874:AcOOH
9856:AcOAc
9813:LiOAc
9669:(PAH)
9257:atoms
9192:atoms
9132:atoms
9130:Eight
9060:atoms
9058:Seven
8966:atoms
8860:atoms
8730:atoms
8718:Water
8648:Ozone
8590:(HNC)
8584:(HCN)
8137:trans
8127:Oleic
8011:trans
7946:trans
7793:(8:1)
7774:(C40)
7768:(C39)
7762:(C38)
7756:(C37)
7750:(C36)
7744:(C35)
7738:(C34)
7732:(C33)
7726:(C32)
7720:(C31)
7714:(C30)
7708:(C29)
7702:(C28)
7696:(C27)
7690:(C26)
7684:(C25)
7678:(C24)
7672:(C23)
7666:(C22)
7660:(C21)
7654:(C20)
7648:(C19)
7642:(C18)
7636:(C17)
7630:(C16)
7624:(C15)
7618:(C14)
7612:(C13)
7606:(C12)
7600:(C11)
7594:(C10)
7220:Other
7195:Other
6721:(PDF)
6690:(PDF)
6683:(PDF)
6661:8 May
6655:(PDF)
6648:(PDF)
6581:(PDF)
6392:(PDF)
6375:(PDF)
6111:Burns
6092:S2CID
5624:S2CID
4984:(PDF)
4966:(PDF)
4935:(PDF)
4790:JSTOR
4755:(PDF)
4740:(PDF)
4705:–331.
4412:Notes
4125:form
4084:NaHCO
3909:COOLi
3901:water
3857:(ii)
3842:ether
3737:Foods
3444:water
3331:+ 2 H
3323:→ 2 H
3210:+ 4 H
3106:yeast
3051:, or
3041:grain
2845:salts
2819:+ 5 O
2709:I + H
2651:]
2536:water
2457:group
2399:water
2387:polar
2344:green
1843:ester
1798:group
1754:Latin
1750:IUPAC
1626:, or
1432:E260
1215:NIOSH
556:InChI
513:2789
379:1380
364:E260
241:ChEBI
181:JSmol
10271:IOAc
10121:BrAc
9979:KOAc
9965:ClAc
9883:FOAc
9860:ROAc
9797:AcOH
9190:Nine
8858:Five
8768:HCCN
8728:Four
8688:SiNC
8167:Mead
7588:(C9)
7582:(C8)
7576:(C7)
7570:(C6)
7564:(C5)
7558:(C4)
7552:(C3)
7468:and
6876:and
6754:2023
6729:2024
6663:2013
6627:ISSN
6588:2013
6542:ISSN
6504:ISSN
6352:ISBN
6267:ISBN
6242:PMID
6220:2016
6193:PMID
6156:2016
6127:PMID
6084:PMID
6035:PMID
5983:PMID
5919:2017
5890:ISBN
5861:ISBN
5823:ISBN
5682:ISBN
5616:ISSN
5572:ISBN
5545:2007
5361:ISBN
5338:PMID
5303:PMID
5254:PMID
5201:ISBN
5174:ISBN
5111:ISBN
5084:PMID
4867:ISBN
4806:2005
4671:ISBN
4625:ISBN
4600:ISBN
4491:ISBN
4379:H314
4375:H226
4350:H314
4330:H315
4190:dyes
4188:for
4180:and
4158:E262
4088:+ CH
4069:base
4035:COO)
4012:zinc
4004:iron
3964:+ CO
3943:and
3905:LiCH
3899:and
3830:(i)
3793:SOCl
3676:base
3463:→ CH
3442:and
3376:and
3370:inks
3352:and
3263:Uses
3214:→ CH
3206:2 CO
3197:and
3180:COOH
3102:must
3072:→ CH
3049:rice
3045:malt
3037:wine
3004:→ CH
2973:Ōita
2907:2 CH
2669:and
2622:and
2598:and
2540:soil
2524:and
2477:fats
2475:and
2452:The
2397:and
2131:BASF
2105:and
2092:tons
1970:Sapa
1966:sapa
1924:wine
1922:and
1920:beer
1871:COOH
1839:salt
1768:acid
1740:The
1715:fats
1713:and
1675:glue
1665:for
1597:COOH
1403:AHFS
1251:IDLH
1069:P310
1061:P280
1047:H314
1043:H226
720:11.6
697:log
643:Odor
614:COOH
489:UNII
434:MeSH
407:KEGG
396:1058
10649:No
10646:Md
10643:Fm
10640:Es
10637:Cf
10634:Bk
10631:Cm
10628:Am
10625:Pu
10622:Np
10607:Pa
10588:**
10511:Pm
10464:Og
10461:Ts
10458:Lv
10455:Mc
10452:Fl
10449:Nh
10446:Cn
10443:Rg
10440:Ds
10437:Mt
10434:Hs
10431:Bh
10428:Sg
10425:Db
10422:Rf
10419:Lr
10416:**
10413:Ra
10410:Fr
10405:Rn
10402:At
10399:Po
10326:Ir
10323:Os
10320:Re
10314:Ta
10311:Hf
10282:Xe
10267:IAc
10263:Te
10176:Tc
10165:Nb
10129:Kr
10117:Se
10106:Ge
9973:Ar
9955:Si
9936:OAc
9887:Ne
9879:FAc
9869:OAc
9807:He
9784:ion
9481:NCO
9381:ion
9288:, C
9255:Ten
8964:Six
8870:ion
7316:S02
7312:ear
6882:G01
6824:PDB
6619:doi
6534:doi
6496:doi
6492:117
6469:doi
6446:doi
6348:FAO
6323:hdl
6295:hdl
6232:PMC
6224:doi
6183:doi
6119:doi
6074:PMC
6066:doi
6025:PMC
6017:doi
6013:351
6009:BMJ
5954:PMC
5946:doi
5853:doi
5815:doi
5787:doi
5741:doi
5714:doi
5651:doi
5647:144
5608:doi
5549:doi
5522:doi
5393:doi
5389:221
5330:doi
5293:PMC
5285:doi
5244:PMC
5234:doi
5230:103
5166:doi
5076:doi
5064:109
5041:doi
5014:hdl
5004:doi
4955:doi
4911:doi
4899:480
4782:doi
4703:330
4483:doi
4100:+ H
4063:or
3998:to
3659:to
3655:of
3579:CO)
3512:or
3475:+ H
3319:+ O
3307:2 H
3153:or
3122:air
3000:+ O
2896:air
2894:in
2847:of
2811:2 C
2726:COI
2582:of
2546:of
2514:by
2495:or
2471:of
2463:by
2317:COO
2307:is
2279:+ H
2139:cis
2123:atm
2113:at
2056:to
2048:to
2044:of
1980:or
1901:−CH
1829:ion
1825:AcO
1821:COO
1760:, "
1728:of
1709:of
1641:).
1451:EPA
1238:REL
1225:PEL
991:GHS
950:WHO
940:WHO
910:298
883:298
856:298
525:EPA
462:176
452:CID
290:171
10690::
10611:UO
10476:*
10346:Hg
10317:W
10300:*
10200:Rh
10188:Cl
10180:Ru
9961:S
9958:P
9944:SO
9940:Al
9928:OH
9865:NH
9825:Be
9298:70
9290:60
9286:60
9284:(C
9009:HC
7532::
6812:,
6808:,
6804:,
6745:.
6625:.
6617:.
6607:24
6605:.
6540:.
6530:13
6528:.
6524:.
6502:.
6490:.
6408:.
6240:.
6230:.
6218:.
6214:.
6191:.
6177:.
6173:.
6147:.
6125:.
6115:35
6113:.
6090:.
6082:.
6072:.
6062:13
6060:.
6056:.
6033:.
6023:.
6011:.
6007:.
5995:^
5979:25
5977:.
5952:.
5940:.
5936:.
5884:.
5859:.
5837:^
5821:.
5799:^
5783:40
5781:.
5764:13
5762:.
5737:23
5735:.
5710:51
5708:.
5696:^
5680:.
5645:.
5622:.
5614:.
5602:.
5586:^
5543:.
5518:13
5516:.
5495:.
5423:.
5405:^
5387:.
5375:^
5336:.
5326:22
5324:.
5301:.
5291:.
5281:29
5279:.
5275:.
5252:.
5242:.
5228:.
5224:.
5172:.
5144:^
5134:.
5082:.
5074:.
5062:.
5037:95
5035:.
5012:.
5002:.
4992:11
4990:.
4986:.
4953:.
4943:31
4941:.
4937:.
4909:.
4897:.
4893:.
4881:^
4865:.
4845:^
4788:.
4778:19
4776:.
4772:.
4748:20
4746:.
4742:.
4722:27
4685:^
4669:.
4667:97
4567:.
4563:.
4545:.
4531:^
4489:.
4377:,
4160:).
4109:A
4079::
4022::
4006:,
3972:CH
3956:CH
3840:,
3733:.
3682:.
3567:CO
3563:CH
3546:CO
3542:CH
3504:,
3500:,
3471:CH
3459:CH
3451:CH
3446:.
3413:CH
3408::
3392:,
3384:,
3372:,
3356:.
3201::
3170:12
3047:,
3043:,
3035:,
3008:CO
2948:.
2932:,
2919:CO
2902:.
2875:,
2871:,
2859:.
2851:,
2827:CO
2817:10
2806::
2731:CH
2718:CH
2701:CH
2653:.
2649:sv
2638:,
2634:,
2630:,
2624:BP
2602:.
2534:,
2449:.
2437:.
2389:)
2325:pH
2313:CH
2298:pK
2270:CO
2262:CH
2163:BP
2098:.
1968:.
1907:.
1879:CO
1875:CH
1867:CH
1865:,
1859:CH
1857:,
1851:CH
1817:CH
1811:,
1801:CH
1717:.
1669:,
1628:HC
1611:,
1605:CO
1601:CH
1593:CH
1571:oʊ
1527:iː
1192:50
1190:LC
1174:50
1172:LD
1067:,
1063:,
1045:,
995::
974:S2
968:AU
953:)
902:(Δ
875:(Δ
739:)
732:(p
610:CH
10666::
10617:2
10613:2
10602:4
10594:3
10581:3
10573:3
10565:3
10557:3
10549:3
10541:3
10533:3
10525:3
10517:3
10506:3
10498:3
10490:3
10482:3
10394:3
10386:4
10379:2
10371:3
10359:2
10352:2
10348:2
10340:3
10332:2
10306:3
10295:2
10277:3
10258:3
10250:4
10243:2
10235:3
10227:2
10214:2
10206:4
10202:2
10194:3
10186:4
10182:2
10171:2
10160:4
10152:3
10142:2
10112:3
10101:3
10093:2
10085:2
10073:2
10065:2
10057:3
10050:2
10042:3
10035:2
10027:3
10020:2
10012:3
10004:4
9996:3
9986:2
9950:4
9946:4
9942:2
9934:2
9926:2
9915:3
9907:2
9899:2
9867:4
9850:4
9846:2
9844:B
9839:3
9831:6
9827:4
9820:2
9773:e
9766:t
9759:v
9488:5
9479:2
9477:H
9424:D
9422:2
9420:N
9296:C
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