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423:
256:
58:
2083:
85:
2002:
67:
1681:
974:
855:
850:
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National
Electric Code (NEC) requires consideration for hazardous areas including those where acetylene may be released during accidents or leaks. Consideration may include electrical classification and use of listed Group A electrical components in US. Further information on determining the areas requiring special consideration is in NFPA 497. In Europe, ATEX also requires consideration for hazardous areas where flammable gases may be released during accidents or leaks.
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76:
6479:
5232:
970:
6443:
5241:
6467:
6455:
1094:
1645:
2278:
2435:
The name acetylene is retained for the compound HC≡CH. It is the preferred IUPAC name, but substitution of any kind is not allowed; however, in general nomenclature, substitution is allowed, for example fluoroacetylene , but not by alkyl groups or any other group that extends the carbon chain, nor by
1611:
is quite versatile – not only because the torch is preferred for some sorts of iron or steel welding (as in certain artistic applications), but also because it lends itself easily to brazing, braze-welding, metal heating (for annealing or tempering, bending or forming), the loosening of corroded nuts
1946:
decomposition of long-chain hydrocarbons at temperatures of 1,700 K (1,430 °C; 2,600 °F) and above. Since such temperatures are highly unlikely on such a small distant body, this discovery is potentially suggestive of catalytic reactions within that moon, making it a promising site to
1624:
and in some aerial locations. Oxyacetylene welding may also be used in areas where electricity is not readily accessible. Oxyacetylene cutting is used in many metal fabrication shops. For use in welding and cutting, the working pressures must be controlled by a regulator, since above 15 psi
2390:
Cylinders should be stored in an area segregated from oxidizers to avoid exacerbated reaction in case of fire/leakage. Acetylene cylinders should not be stored in confined spaces, enclosed vehicles, garages, and buildings, to avoid unintended leakage leading to explosive atmosphere. In the US,
1392:
This last reaction is implemented in the process of anaerobic decomposition of methane by microwave plasma. The advantage of this technology is the absence of CO2 emissions and the joint production of hydrogen as a secondary product. It makes it a low-carbon technology production and also an
1239:" (hydrogen quadricarbide), were incorrect because many chemists at that time used the wrong atomic mass for carbon (6 instead of 12). Berthelot was able to prepare this gas by passing vapours of organic compounds (methanol, ethanol, etc.) through a red hot tube and collecting the
973:
998:
2334:-like smell. It is also highly flammable, as are most light hydrocarbons, hence its use in welding. Its most singular hazard is associated with its intrinsic instability, especially when it is pressurized: under certain conditions acetylene can react in an
1164:. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as
1892:
The energy richness of the C≡C triple bond and the rather high solubility of acetylene in water make it a suitable substrate for bacteria, provided an adequate source is available. A number of bacteria living on acetylene have been identified. The
2354:. Consequently, acetylene, if initiated by intense heat or a shockwave, can decompose explosively if the absolute pressure of the gas exceeds about 200 kilopascals (29 psi). Most regulators and pressure gauges on equipment report
2956:
Pässler, Peter; Hefner, Werner; Buckl, Klaus; Meinass, Helmut; Meiswinkel, Andreas; Wernicke, Hans-Jürgen; Ebersberg, Günter; Müller, Richard; Bässler, Jürgen; Behringer, Hartmut; Mayer, Dieter (2008). "Acetylene
Chemistry".
2650:
Pässler, Peter; Hefner, Werner; Buckl, Klaus; Meinass, Helmut; Meiswinkel, Andreas; Wernicke, Hans-Jürgen; Ebersberg, Günter; Müller, Richard; Bässler, Jürgen; Behringer, Hartmut; Mayer, Dieter (2008). "Acetylene
Chemistry".
991:
2504:
1746:, which in turn can be oxidized to acetic acid. Processes leading to acrylates were also commercialized. Almost all of these processes became obsolete with the availability of petroleum-derived ethylene and propylene.
3020:
Habil, Phil; Bartholoméa, E. (1954). "Probleme großtechnischer
Anlagen zur Erzeugung von Acetylen nach dem Sauerstoff-Verfahren (Problems of large-scale plants for the production of acetylene by the oxygen method)".
2992:
Habil, Phil; Sachsse, Hans (1954). "Herstellung von
Acetylen durch unvollständige Verbrennung von Kohlenwasserstoffen mit Sauerstoff (Production of acetylene by incomplete combustion of hydrocarbons with oxygen)".
2602:
4491:"NFPA Free Access to NFPA 497 – Recommended Practice for the Classification of Flammable Liquids, Gases, or Vapors and of Hazardous (Classified) Locations for Electrical Installations in Chemical Process Areas"
4494:
4468:
863:
1534:
corresponds to the melting point (−80.8 °C) at the minimal pressure at which liquid acetylene can exist (1.27 atm). At temperatures below the triple point, solid acetylene can change directly to the
2381:
Information on safe storage of acetylene in upright cylinders is provided by the OSHA, Compressed Gas
Association, United States Mine Safety and Health Administration (MSHA), EIGA, and other agencies.
1880:
and many years later by low-power/high-lumen LEDs. Nevertheless, acetylene lamps remain in limited use in remote or otherwise inaccessible areas and in countries with a weak or unreliable central
2261:
830:
1730:. Except in China, use of acetylene as a chemical feedstock has declined by 70% from 1965 to 2007 owing to cost and environmental considerations. In China, acetylene is a major precursor to
1559:(DMF), the solubility is 51 g. At 20.26 bar, the solubility increases to 689.0 and 628.0 g for acetone and DMF, respectively. These solvents are used in pressurized gas cylinders.
1323:. Approximately 400,000 tonnes were produced by this method in 1983. Its presence in ethylene is usually undesirable because of its explosive character and its ability to poison
4320:
5792:
5562:
5522:
5014:
2378:, which renders it safe to transport and use, given proper handling. Acetylene cylinders should be used in the upright position to avoid withdrawing acetone during use.
1587:
due to the high temperature of the flame. Combustion of acetylene with oxygen produces a flame of over 3,600 K (3,330 °C; 6,020 °F), releasing 11.8
4490:
976:
5723:
5698:
5688:
4464:
4387:
1742:
Prior to the widespread use of petrochemicals, coal-derived acetylene was a building block for several industrial chemicals. Thus acetylene can be hydrated to give
4356:
3373:
Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (15 June 2000),
9254:
8927:
9246:
9023:
8991:
8228:
8204:
8192:
6607:
1607:
have made oxy-fuel welding nearly extinct for many applications. Acetylene usage for welding has dropped significantly. On the other hand, oxy-acetylene welding
3477:
Takashi Ohara; Takahisa Sato; Noboru
Shimizu; Günter Prescher; Helmut Schwind; Otto Weiberg; Klaus Marten; Helmut Greim (2003). "Acrylic Acid and Derivatives".
9238:
9182:
9015:
8983:
8935:
8895:
8672:
8651:
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3169:
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6183:
5999:
5934:
5874:
5802:
5708:
5602:
5472:
5427:
5098:
2528:
1034:
6263:
3801:
Grainger, D., (2001). By cars' early light: A short history of the headlamp: 1900s lights bore port and starboard red and green lenses. National Post. DT7.
3711:
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9071:
9039:
9007:
8959:
8677:
8582:
8558:
6612:
5728:
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5542:
2012:. The reaction is catalyzed by mercury salts. This reaction once was the dominant technology for acetaldehyde production, but it has been displaced by the
9108:
9063:
9055:
9031:
8999:
8919:
8664:
5658:
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5683:
3288:
1107:
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4880:
3247:
2959:
2653:
1441:
The use of this technology has declined worldwide with the notable exception of China, with its emphasis on coal-based chemical industry. Otherwise
2058:. Its bonding to the metal is somewhat similar to that of ethylene complexes. These complexes are intermediates in many catalytic reactions such as
1495:
between the carbons, while on each of the other two ends hydrogen atoms attach also by σ bonds. The two unchanged 2p orbitals form a pair of weaker
9222:
7889:
7795:
7771:
7759:
5321:
5023:
7831:
7819:
7807:
7783:
5678:
5007:
3666:
2903:
7877:
7393:
7381:
5348:
3895:
ten Brink, Felix (2014). "Chapter 2. Living on acetylene. A Primordial Energy Source". In Peter M. H. Kroneck and Martha E. Sosa Torres (ed.).
4436:
7216:
5894:
5291:
3245:
Harreus, Albrecht Ludwig; Backes, R.; Eichler, J.-O.; Feuerhake, R.; Jäkel, C.; Mahn, U.; Pinkos, R.; Vogelsang, R. (2011). "2-Pyrrolidone".
3098:
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2729:
7843:
7719:
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7369:
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4232:
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7580:
7568:
6516:
5353:
1793:
produces a highly electrically conducting material. Although such materials are not useful, these discoveries led to the developments of
1393:
electrified process. For 32 t of methane transformed, production of 26 t of acetylene and 6 t of hydrogen (according to stoichiometry).
8438:
7640:
7628:
7616:
7592:
7341:
5000:
7307:
6221:
5537:
3312:
2477:
2790:
1347:
The heaviest alkanes in petroleum and natural gas are cracked into lighter molecules which are dehydrogenated at high temperature:
4411:
4194:
1591:/g. Oxygen with acetylene is the hottest burning common gas mixture. Acetylene is the third-hottest natural chemical flame after
4132:
Midland, M. M.; McLoughlin, J. I.; Werley, Ralph T. (Jr.) (1990). "Preparation and Use of
Lithium Acetylide: 1-Methyl-2-ethynyl-
2689:
1487:
with one 2p orbital thus forming an sp hybrid. The other two 2p orbitals remain unhybridized. The two ends of the two sp hybrid
5753:
5512:
5432:
4327:
799:
3936:
1842:(also known as lithium acetylide). The carbide can then be reacted with water, as usual, to form acetylene gas to feed into a
4266:
3959:
3912:
3774:
3450:
3394:
3209:
3140:
2588:
2428:
750:
6134:
3780:
3741:
2761:
1434:
1 kg of calcium carbide combines with 562.5 g of water to release 350 liters of acetylene. This reaction was discovered by
905:
9316:
2844:
84:
4383:
4352:
1176:
777:
2210:
1460:. In the US, this process was an important part of the late-19th century revolution in chemistry enabled by the massive
6386:
4961:
4116:
3823:
3264:
2976:
2670:
1785:
films. Polyacetylene, a chain of CH centres with alternating single and double bonds, was one of the first discovered
6286:
4890:
4595:
4291:
2937:
2713:
1102:
437:
4522:
3157:
1114:
929:
6509:
6411:
4971:
3689:
2055:
984:
384:
379:
3547:"Ueber eine neue Methode direkter Addition von Wasser (Hydratation) an die Kohlenwasserstoffe der Acetylenreihe"
2542:
1199:, who identified it as a "new carburet of hydrogen". It was an accidental discovery while attempting to isolate
4057:
3566:
3494:
2387:
catalyses the decomposition of acetylene, and as a result acetylene should not be transported in copper pipes.
1540:
1187:. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°.
573:
3589:
6336:
4531:
109:
17:
3280:
6525:
6371:
4561:
1600:
1584:
895:
354:
251:
75:
5567:
401:
213:
6502:
4552:
Movie explaining acetylene formation from calcium carbide and the explosive limits forming fire hazards
2412:
2183:
1853:
drove much acetylene commercialization in the early 20th century. Common applications included coastal
1778:
1324:
1058:
1045:
901:
854:
627:
3674:
2900:
9311:
8534:
6326:
6321:
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4956:
2500:
933:
263:
1930:
Acetylene is a moderately common chemical in the universe, often associated with the atmospheres of
9321:
6366:
4951:
4885:
4429:
3651:
2008:
The hydration of acetylene is a vinylation reaction, but the resulting vinyl alcohol isomerizes to
1798:
1526:
At atmospheric pressure, acetylene cannot exist as a liquid and does not have a melting point. The
1510:
1011:
418:
57:
3123:
Holzrichter, Klaus; Knott, Alfons; Mertschenk, Bernd; Salzinger, Josef (2013). "Calcium
Carbide".
3091:
2020:, a cheaper feedstock. A similar situation applies to the conversion of acetylene to the valuable
1456:
Calcium carbide production requires high temperatures, ~2000 °C, necessitating the use of an
1219:), which reacted with water to release the new gas. It was rediscovered in 1860 by French chemist
9150:
6446:
2726:
2580:
CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data
1877:
656:
3047:
2869:
849:
8951:
6301:
5266:
5176:
5053:
5048:
4225:
3940:
3430:
3374:
2786:
Note sur une nouvelle série de composés organiques, le quadricarbure d'hydrogène et ses dérivés
2165:
726:
4556:
3840:
1251:
gases. Berthelot later obtained acetylene directly by passing hydrogen between the poles of a
66:
9079:
8943:
8903:
8614:
8061:
8044:
6597:
6592:
6356:
6331:
5969:
5587:
5134:
4588:
3963:
3646:
2409:
Nomenclature of
Organic Chemistry. IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1817:
1794:
1786:
1484:
1130:
877:
842:
31:
3510:
Schobert, Harold (2014). "Production of Acetylene and Acetylene-based Chemicals from Coal".
2929:
1710:, or acrylic esters. Metal catalysts are required. These derivatives form products such as
9214:
9158:
8690:
8606:
8343:
7106:
6417:
6401:
6026:
5397:
5368:
5249:
5073:
4966:
4946:
4844:
3996:
3605:
2828:
2059:
1457:
1316:
672:
363:
97:
2474:
2038:
is used instead of acetylene for some vinylations, which are more accurately described as
925:
233:
8:
9275:
9166:
8851:
8685:
8307:
8081:
7327:
7101:
6602:
6361:
6341:
6154:
5844:
5332:
5196:
5171:
5139:
5058:
4871:
3309:
2783:
2153:
1965:
1897:
1763:
1696:
1626:
1477:
1220:
1204:
127:
4408:
4000:
3609:
2832:
1435:
422:
255:
193:
161:
137:
9296:
8839:
8834:
8743:
8727:
8334:
8168:
8138:
8074:
6459:
6381:
6351:
6296:
6173:
6149:
5648:
5582:
5447:
5407:
5258:
5221:
5181:
5160:
5103:
5078:
4981:
4941:
4921:
4105:
4022:
3865:
3476:
3400:
2797:(Note on a new series of organic compounds, tetra-carbon hydride and its derivatives),
2738:
Report of the Sixth Meeting of the British Association for the Advancement of Science …
2271:
1869:
1831:
1755:
1503:
694:
688:
173:
4190:
2493:
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9198:
9190:
8756:
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8622:
8513:
8498:
8493:
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7517:
6918:
6848:
6708:
6656:
6640:
6632:
6553:
6406:
5989:
5889:
5859:
5777:
5517:
5402:
5358:
5306:
5113:
5108:
5040:
4931:
4545:
4297:
4287:
4262:
4112:
4053:
4014:
3918:
3908:
3870:
3819:
3770:
3527:
3490:
3446:
3404:
3390:
3355:
3260:
3205:
3136:
2972:
2933:
2709:
2686:
2666:
2594:
2584:
2424:
2367:
2299:
2063:
2025:
1866:
1843:
1806:
1692:
1660:
Acetylene is useful for many processes, but few are conducted on a commercial scale.
1603:
was a popular welding process in previous decades. The development and advantages of
1556:
1208:
1207:
with carbon at very high temperatures, he produced a residue of what is now known as
1138:
8787:
4992:
2082:
9301:
8975:
8711:
8698:
8598:
8542:
8503:
8429:
8416:
8370:
8159:
7037:
6681:
6558:
6483:
6471:
6391:
6291:
6196:
6144:
5577:
5452:
5417:
5338:
5326:
5286:
5191:
5124:
4581:
4172:
4145:
4082:
4073:
Reppe, Walter; Kutepow, N; Magin, A (1969). "Cyclization of Acetylenic Compounds".
4045:
4026:
4004:
3987:
3944:
3900:
3860:
3852:
3701:
3613:
3558:
3519:
3482:
3438:
3382:
3345:
3334:"Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited"
3252:
3224:
Handbook of Chemistry and Physics (60th ed., CRC Press 1979–80), p. C-303 in Table
3128:
3030:
3002:
2964:
2925:
2836:
2658:
2416:
2157:
1981:
1810:
1727:
1592:
1461:
587:
495:
8860:
8807:
8394:
3967:
3486:
3256:
3132:
2968:
2662:
1827:(that is, hardening) of steel when the object is too large to fit into a furnace.
8826:
8706:
8550:
8508:
8484:
8470:
8456:
7122:
6773:
6648:
6563:
6543:
6079:
6054:
5592:
5532:
5316:
5216:
5201:
5186:
5093:
5083:
4976:
4849:
4526:
4415:
3764:
3733:
3316:
3102:
3066:
3054:
2907:
2880:
2794:
2755:
2733:
2693:
2481:
2454:
Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013
2449:
2319:
2177:
2039:
2029:
1881:
1839:
1703:
1488:
1402:
1165:
1024:
937:
327:
282:
8519:
6573:
6533:
3904:
3429:
Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (15 June 2000),
2816:
2001:
1243:. He also found that acetylene was formed by sparking electricity through mixed
8801:
8751:
8022:
7114:
6821:
6797:
6785:
6761:
6664:
6548:
6494:
6316:
6281:
6064:
5954:
5919:
5904:
5839:
5834:
5733:
5633:
5552:
5527:
5492:
5437:
5412:
5281:
5129:
4418:
UNITED STATES DEPARTMENT OF LABOR Mine Safety and Health Administration – MSHA.
3597:
2355:
2343:
2267:
2021:
2013:
1985:
1802:
1774:
1767:
1731:
1688:
1573:
1481:
1085:
913:
645:
617:
8000:
7474:
4568:
4551:
4111:(1st ed.). New York: Marcel Dekker, inc. pp. 170–179 & 225–241.
3706:
3562:
2872:
Synthèse de l'acétylène par la combinaison directe du carbone avec l'hydrogène
2524:
1616:
cable-repair technicians still use portable acetylene-fuelled torch kits as a
9290:
6346:
6201:
6084:
6059:
6040:
5984:
5864:
5822:
5817:
5557:
5547:
5507:
5382:
5276:
5231:
5206:
5088:
5068:
4926:
4911:
4176:
4149:
4049:
3442:
3437:, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. a01_279,
3386:
3381:, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. a04_455,
2598:
2576:
2193:
2043:
2035:
1989:
1824:
1782:
1723:
1719:
1715:
1711:
1531:
1465:
1180:
917:
707:
558:
244:
6982:
4301:
3856:
2883:(Synthesis of acetylene by the direct combination of carbon with hydrogen),
2475:
Acyclic Hydrocarbons. Rule A-3. Unsaturated Compounds and Univalent Radicals
1680:
9267:
8818:
8421:
8126:
8114:
7857:
7747:
7666:
6422:
6276:
6129:
6069:
6049:
6021:
5949:
5829:
5812:
5767:
5718:
5623:
5343:
5296:
5144:
4936:
4916:
4875:
4086:
4018:
3922:
3874:
3531:
3359:
3034:
3006:
2371:
2307:
2067:
2009:
1901:
1858:
1850:
1759:
1743:
1707:
1664:
1577:
1527:
1401:
Acetylene is traditionally produced by hydrolysis (reaction with water) of
564:
2578:
2420:
2075:
997:
8461:
8276:
8151:
7865:
7735:
7192:
7180:
7079:
7074:
7069:
7046:
6749:
6737:
6725:
6396:
6306:
6271:
6238:
6164:
6139:
5979:
5884:
5854:
5738:
5653:
5643:
5373:
5301:
1873:
1849:
Acetylene combustion produces a strong, bright light and the ubiquity of
1613:
1604:
1580:
1320:
1196:
1184:
1157:
3897:
The Metal-Driven Biogeochemistry of Gaseous Compounds in the Environment
2623:
1267:
acetylene production is dominated by partial combustion of natural gas.
983:
8180:
8102:
7976:
7204:
6809:
6311:
6253:
6216:
6191:
6089:
5899:
5762:
4862:
3899:. Metal Ions in Life Sciences. Vol. 14. Springer. pp. 15–35.
3617:
3587:
2335:
2054:
Acetylene and its derivatives (2-butyne, diphenylacetylene, etc.) form
1973:
1961:
1854:
1834:. The carbonaceous material in an archeological sample is treated with
1625:(100 kPa), if subjected to a shockwave (caused, for example, by a
1492:
1276:
1275:
Since the 1950s, acetylene has mainly been manufactured by the partial
990:
598:
517:
264:
224:
3523:
3350:
3333:
8035:
7727:
7698:
7544:
7414:
7357:
7168:
7084:
6891:
6243:
6108:
5944:
5748:
5628:
5457:
4906:
4866:
4700:
4695:
3734:"Lighthouse Lamps Through Time by Thomas Tag | US Lighthouse Society"
2840:
2375:
2323:
2201:
2197:
2135:
2042:. Higher esters of vinyl acetate have been used in the synthesis of
1993:
1943:
1935:
1931:
1630:
1617:
1588:
1442:
1332:
1200:
1169:
392:
374:
4540:
4519:
4009:
3982:
3546:
2362:, or 15 psig. It is therefore supplied and stored dissolved in
1084:
Except where otherwise noted, data are given for materials in their
8451:
8030:
7926:
7686:
7556:
7457:
7422:
7315:
7286:
7156:
6953:
6713:
6211:
6123:
5924:
5787:
5772:
5743:
5612:
5387:
5211:
5155:
5149:
5118:
5063:
5031:
4826:
4821:
4780:
4775:
4734:
4729:
4724:
4671:
4666:
3122:
2351:
2303:
2017:
1862:
1668:
1634:
1596:
1328:
1312:
1252:
1248:
1244:
1240:
956:
388:
302:
2522:
1543:. The sublimation point at atmospheric pressure is −84.0 °C.
949:
160:
8290:
7953:
7674:
7536:
7349:
7278:
7264:
7140:
6883:
6856:
6692:
6376:
6206:
6159:
6118:
6074:
6016:
6011:
5974:
5964:
5959:
5914:
5909:
5849:
5782:
5673:
5668:
5618:
5497:
5487:
5240:
4741:
4678:
4632:
2363:
2339:
2161:
1969:
1835:
1621:
1552:
1496:
1280:
610:
606:
548:
314:
3841:"Acetylenotrophy: a hidden but ubiquitous microbial metabolism?"
2708:(4th ed., Saunders College Publishing 1992), pp. 328–329, 1046.
7918:
7910:
7148:
7064:
7059:
7054:
6700:
6427:
6248:
6230:
5693:
5663:
5165:
4857:
4853:
4804:
4787:
4758:
4707:
4649:
4604:
4072:
3332:
Trotuş, Ioan-Teodor; Zimmermann, Tobias; Schüth, Ferdi (2014).
2384:
2347:
2338:
addition-type reaction to form a number of products, typically
2331:
2327:
1939:
1894:
1790:
1672:
1638:
1536:
1336:
1161:
941:
887:
204:
42:
38:
7652:
7528:
5462:
5392:
3690:"Radiocarbon dating problems using acetylene as counting gas"
3244:
1977:
1450:
1264:
338:
184:
150:
3766:
The 100 Most Important Chemical Compounds: A Reference Guide
2583:(2016-2017, 97th ed.). Boca Raton, Florida: CRC Press.
2456:. London: Queen Mary University. Section P-14.3.4.2 (d)
2358:, and the safe limit for acetylene therefore is 101 kPa
1754:
In 1881, the Russian chemist Mikhail Kucherov described the
1644:
909:
406:
4226:"law.resource.org CGA g-1 2009 (incorporated by reference)"
3980:
2318:
Acetylene is not especially toxic, but when generated from
2286:
2277:
1816:
In the 1920s, pure acetylene was experimentally used as an
1649:
1446:
1071:
538:
293:
4573:
3310:
ESAB Oxy-acetylene welding handbook – Acetylene properties
2920:
Gannon, Richard E. (2000). "Acetylene from Hydrocarbons".
2577:
William M. Haynes; David R. Lide; Thomas J. Bruno (2016).
4261:. London; New York: Blackie Academic & Professional.
2955:
2649:
1846:
to measure the isotopic ratio of carbon-14 to carbon-12.
1648:
Acetylene fuel container/burner as used in the island of
4569:
CDC – NIOSH Pocket Guide to Chemical Hazards – Acetylene
1872:. In most of these applications, direct combustion is a
4286:. Warszawa: Wydawnictwo Ministerstwa Obrony Narodowej.
4163:
Coffman, Donald D. (1940). "Dimethylethhynylcarbinol".
4131:
3428:
2857:
Atomic weights of 6 and 12 were both in use for carbon.
3331:
1838:
metal in a small specialized research furnace to form
1770:, this reaction was conducted on an industrial scale.
7473:
5022:
4435:. Office of Environmental Health & Safety (EHS).
3937:"Precursor to Proteins and DNA found in Stellar Disk"
3645:
3372:
3190:
Organic Chemistry 7th ed. by J. McMurry, Thomson 2008
3162:
The Chemical News and the Journal of Physical Science
2624:
R. H. Petrucci; W. S. Harwood; F. G. Herring (2002).
2529:
National Institute for Occupational Safety and Health
2213:
1964:
reactions, H−X compounds add across the triple bond.
1270:
883:
6981:
2817:"The Karlsruhe Congress: A centennial retrospective"
2447:
2322:, it can contain toxic impurities such as traces of
1551:
At room temperature, the solubility of acetylene in
4541:
Acetylene, the Principles of Its Generation and Use
4465:"NFPA free access to 2017 edition of NFPA 70 (NEC)"
2256:{\displaystyle {\ce {HC#CH + RM -> RH + HC#CM}}}
1702:In addition to ethynylation, acetylene reacts with
1595:'s 5,260 K (4,990 °C; 9,010 °F) and
4104:
4075:Angewandte Chemie International Edition in English
3588:Dmitry A. Ponomarev; Sergey M. Shevchenko (2007).
2255:
1572:Approximately 20% of acetylene is supplied by the
3981:John Spencer; David Grinspoon (25 January 2007).
3960:"LPSC: Wednesday afternoon: Cassini at Enceladus"
3433:, in Wiley-VCH Verlag GmbH & Co. KGaA (ed.),
3377:, in Wiley-VCH Verlag GmbH & Co. KGaA (ed.),
37:"Ethyne" redirects here. Not to be confused with
9288:
6524:
4427:
4250:
3957:
3199:
3019:
2727:"Notice of a new gaseous bicarburet of hydrogen"
1599:at 4,798 K (4,525 °C; 8,177 °F).
1311:It is a recovered side product in production of
1227:. Berthelot's empirical formula for acetylene (C
553:1.1772 g/L = 1.1772 kg/m (0 °C, 101.3 kPa)
326:
4520:Acetylene Production Plant and Detailed Process
3816:Carbide Light: The Last Flame in American Mines
3204:(3rd ed.). Prentice Hall. pp. 94–95.
2922:Kirk-Othmer Encyclopedia of Chemical Technology
2757:Acetylene: Its Properties, Manufacture and Uses
1876:, and so acetylene has been replaced, first by
972:
136:
4384:"OSHA 29 CFR 1926.350 Gas Welding and cutting"
4042:Encyclopedia of Reagents for Organic Synthesis
3551:Berichte der Deutschen Chemischen Gesellschaft
3479:Ullmann's Encyclopedia of Industrial Chemistry
3435:Ullmann's Encyclopedia of Industrial Chemistry
3379:Ullmann's Encyclopedia of Industrial Chemistry
3248:Ullmann's Encyclopedia of Industrial Chemistry
3125:Ullmann's Encyclopedia of Industrial Chemistry
3094:Bildung des Acetylens durch Kohlenstoffcalcium
2960:Ullmann's Encyclopedia of Industrial Chemistry
2654:Ullmann's Encyclopedia of Industrial Chemistry
945:
6510:
5008:
4589:
4284:1000 słów o materiałach wybuchowych i wybuchu
3590:"Hydration of Acetylene: A 125th Anniversary"
2016:, which affords acetaldehyde by oxidation of
1942:. Natural acetylene is believed to form from
1900:catalyzes the hydration of acetylene to give
1342:
563:−80.8 °C (−113.4 °F; 192.3 K)
4040:Manchand, Percy S. (2001). "Vinyl Acetate".
3105:(Formation of actylene by calcium carbide),
2991:
2704:Whitten K. W., Gailey K. D. and Davis R. E.
2628:(8th ed.). Prentice-Hall. p. 1072.
2505:Institute for Occupational Safety and Health
2436:characteristic groups expressed by suffixes.
2310:plastics. Halogens add to the triple bond.
8386:
8150:
8073:
7045:
6585:
4125:
4066:
3687:
3544:
2951:
2949:
2049:
1988:are produced industrially by vinylation of
1934:. One curious discovery of acetylene is on
30:"HCCH" redirects here. For other uses, see
7969:
6517:
6503:
5015:
5001:
4596:
4582:
2687:Material Safety and Data Sheet – Acetylene
2543:"Acetylene – Gas Encyclopedia Air Liquide"
1830:Acetylene is used to volatilize carbon in
1663:One of the major chemical applications is
421:
254:
232:
7992:
7856:
7718:
6625:
4881:Fritsch–Buttenberg–Wiechell rearrangement
4008:
3894:
3864:
3705:
3655:. Vol. 1 (14 ed.). p. 119.
3375:"Butanediols, Butenediol, and Butynediol"
3349:
3273:
3200:Housecroft, C. E.; Sharpe, A. G. (2008).
2645:
2643:
2641:
2639:
2637:
2635:
2535:
2484:, IUPAC Nomenclature of Organic Chemistry
2441:
2306:, providing a feedstock for a variety of
1555:is 27.9 g per kg. For the same amount of
921:
581:−84 °C; −119 °F; 189 K (1 atm)
362:
7450:
7413:
6946:
6911:
4098:
4096:
4039:
3509:
2946:
2523:NIOSH Pocket Guide to Chemical Hazards.
2401:
2276:
1643:
1620:tool for sealing lead sleeve splices in
8327:
7946:
7340:
6876:
4162:
4156:
3659:
3327:
3325:
3226:Physical Constants of Organic Compounds
3155:
2930:10.1002/0471238961.0103052007011414.a01
2572:
2570:
2568:
2518:
2516:
2514:
2512:
2164:solutions with ease due to a favorable
1955:
1396:
417:
14:
9289:
8363:
8289:
7909:
7306:
7277:
7139:
6691:
4281:
4256:
3813:
3240:
3238:
2919:
2753:
2632:
2313:
2171:
1516:
1327:. It is selectively hydrogenated into
1019:300 °C (572 °F; 573 K)
245:
7665:
7527:
6841:
6498:
4996:
4577:
4459:
4457:
4421:
4378:
4376:
4374:
4315:
4313:
4311:
4220:
4218:
4216:
4214:
4212:
4102:
4093:
3983:"Planetary science: Inside Enceladus"
3809:
3807:
3762:
3744:from the original on 25 February 2017
3714:from the original on 26 December 2013
2847:from the original on 30 December 2021
2487:
1887:
1749:
449:Key: HSFWRNGVRCDJHI-UHFFFAOYSA-N
212:
192:
4497:from the original on 1 December 2016
4471:from the original on 1 December 2016
4428:Daniel_Sarachick (16 October 2003).
4390:from the original on 1 December 2016
4359:from the original on 1 December 2016
4238:from the original on 10 October 2016
3838:
3569:from the original on 2 December 2020
3322:
3291:from the original on 12 January 2018
2814:
2679:
2565:
2509:
1667:of formaldehyde. Acetylene adds to
1235:), as well as the alternative name "
1195:Acetylene was discovered in 1836 by
4532:Acetylene at Chemistry Comes Alive!
3285:Products and Supply > Fuel Gases
3235:
2760:. Vol. 1. Academic Press Inc.
1612:and bolts, and other applications.
1521:
459:Key: HSFWRNGVRCDJHI-UHFFFAOYAY
317:
301:
24:
6387:Nexus for Exoplanet System Science
4962:Azide-alkyne Huisgen cycloaddition
4454:
4371:
4321:"EIGA Code of Practice: Acetylene"
4308:
4209:
4197:from the original on 11 March 2014
3958:Emily Lakdawalla (17 March 2006).
3943:. 20 December 2005. Archived from
3804:
3411:from the original on 19 March 2022
3172:from the original on 15 April 2021
2764:from the original on 15 April 2021
2685:Compressed Gas Association (1995)
1980:give vinyl thioethers. Similarly,
1737:
1271:Partial combustion of hydrocarbons
968:
25:
9333:
6287:Atomic and molecular astrophysics
5024:Molecules detected in outer space
4513:
4442:from the original on 13 July 2018
3783:from the original on 17 June 2016
3649:(1930). "Acetylene in medicine".
3627:from the original on 11 June 2011
3459:from the original on 9 March 2022
1179:because its two carbon atoms are
6477:
6465:
6453:
6442:
6441:
5248:
5239:
5230:
4353:"OSHA 29 CFR 1910.102 Acetylene"
3107:Annalen der Chemie und Pharmacie
3048:Acetylene: How Products are Made
2293:
2081:
2074:
2056:complexes with transition metals
2000:
1947:search for prebiotic chemistry.
1823:Acetylene is sometimes used for
1679:
1092:
853:
848:
507:
83:
74:
65:
56:
6412:Polycyclic aromatic hydrocarbon
4557:Calcium Carbide & Acetylene
4483:
4402:
4345:
4275:
4183:
4033:
3974:
3951:
3929:
3888:
3832:
3795:
3756:
3726:
3681:
3639:
3581:
3538:
3503:
3470:
3422:
3366:
3303:
3218:
3193:
3184:
3149:
3116:
3084:
3059:
3041:
3013:
2985:
2913:
2894:
2862:
2808:
2776:
2747:
2719:
2698:
2605:from the original on 4 May 2022
2553:from the original on 4 May 2022
2062:to benzene, tetramerization to
1562:
1088:(at 25 °C , 100 kPa).
677:21.4 mW·m·K (300 K)
4136:-3,3-dimethyl-2-norbornanol".
2617:
2468:
2413:The Royal Society of Chemistry
2232:
1258:
501:
13:
1:
6337:Extraterrestrial liquid water
4891:Seyferth–Gilbert homologation
3487:10.1002/14356007.a01_161.pub2
3257:10.1002/14356007.a22_457.pub2
3133:10.1002/14356007.a04_533.pub2
2969:10.1002/14356007.a01_097.pub3
2821:Journal of Chemical Education
2663:10.1002/14356007.a01_097.pub3
2394:
1480:, in each carbon atom the 2s
1039:(US health exposure limits):
6526:Binary compounds of hydrogen
4562:The Periodic Table of Videos
4409:Special Hazards of Acetylene
4103:Viehe, Heinz Günter (1969).
3839:Akob, Denise (August 2018).
2330:, which gives it a distinct
2178:Acetylide § Preparation
1950:
1675:to form α-ethynyl alcohols:
1655:
1502:Since acetylene is a linear
1445:has increasingly supplanted
1190:
603:slightly soluble in alcohol
27:Hydrocarbon compound (HC≡CH)
7:
9317:Synthetic fuel technologies
5568:Protonated hydrogen cyanide
4972:Cadiot–Chodkiewicz coupling
4603:
3905:10.1007/978-94-017-9269-1_2
1766:. Before the advent of the
1706:, acetylene reacts to give
1605:arc-based welding processes
1175:As an alkyne, acetylene is
10:
9338:
4565:(University of Nottingham)
3763:Myers, Richard L. (2007).
3158:"Manufacture of Cyanamide"
2725:Edmund Davy (August 1836)
2448:Moss, G.P. (web version).
2346:, possibly in addition to
2175:
1567:
1471:
1343:Dehydrogenation of alkanes
36:
29:
9266:
9107:
8878:
8535:Transition metal hydrides
8533:
8483:
8060:
7516:
7097:
7036:
6680:
6572:
6532:
6436:
6327:Earliest known life forms
6322:Diffuse interstellar band
6262:
6182:
6107:
5998:
5933:
5873:
5801:
5793:Protonated cyanoacetylene
5707:
5601:
5563:Protonated carbon dioxide
5523:Hydromagnesium isocyanide
5471:
5257:
5228:
5039:
5030:
4899:
4837:
4611:
4191:"Acetylene Specification"
3845:FEMS Microbiology Ecology
3707:10.2458/azu_js_rc.32.1278
3563:10.1002/cber.188101401320
2501:GESTIS Substance Database
2138:, species of the formula
1972:add to acetylene to give
1699:is used as the catalyst.
1574:industrial gases industry
1237:quadricarbure d'hydrogène
1082:
1033:
829:
824:
700:
681:
488:
468:
433:
120:
108:
96:
91:
82:
73:
64:
55:
6372:Iron–sulfur world theory
6367:Photodissociation region
6070:Methyl-cyano-diacetylene
4430:"ACETYLENE SAFETY ALERT"
4282:Korzun, Mikołaj (1986).
4177:10.15227/orgsyn.020.0040
4150:10.15227/orgsyn.068.0014
4050:10.1002/047084289X.rv008
3652:Encyclopaedia Britannica
3545:Kutscheroff, M. (1881).
3443:10.1002/14356007.a01_279
3387:10.1002/14356007.a04_455
3156:Freeman, Horace (1919).
3023:Chemie Ingenieur Technik
2995:Chemie Ingenieur Technik
2274:reagents are effective.
2192:of 25, acetylene can be
2122:at basic conditions (50–
2050:Organometallic chemistry
1799:Nobel Prize in Chemistry
1762:using catalysts such as
1546:
896:Precautionary statements
446:InChI=1S/C2H2/c1-2/h1-2H
6447:Category:Astrochemistry
6037:, fullerene, buckyball)
5724:Cyanobutadiynyl radical
5699:Silicon-carbide cluster
5689:Protonated formaldehyde
4107:Chemistry of Acetylenes
3818:. Bergamot Publishing.
3251:. Weinheim: Wiley-VCH.
3053:20 January 2007 at the
2963:. Weinheim: Wiley-VCH.
2906:28 January 2012 at the
2815:Ihde, Aaron J. (1961).
2657:. Weinheim: Wiley-VCH.
2480:10 October 2000 at the
2066:, and carbonylation to
1797:, as recognized by the
1779:Ziegler–Natta catalysts
1449:as the chief source of
1325:Ziegler–Natta catalysts
1065:C 2500 ppm (2662 mg/m)
657:Magnetic susceptibility
456:InChI=1/C2H2/c1-2/h1-2H
9268:Exotic matter hydrides
6460:Outer space portal
6302:Circumstellar envelope
5267:Aluminium(I) hydroxide
5177:Phosphorus mononitride
5054:Aluminium monofluoride
5049:Aluminium monochloride
4257:Downie, N. A. (1997).
4087:10.1002/anie.196907271
3941:W. M. Keck Observatory
3035:10.1002/cite.330260503
3007:10.1002/cite.330260502
2879:14 August 2020 at the
2754:Miller, S. A. (1965).
2370:(DMF), contained in a
2290:
2289:, commissioned in 2020
2257:
2166:solubility equilibrium
1795:organic semiconductors
1787:organic semiconductors
1652:
1223:, who coined the name
979:
622:44.2 atm (20 °C)
6357:Interplanetary medium
6332:Extraterrestrial life
5970:Octatetraynyl radical
5588:Tricarbon monosulfide
5135:Magnesium monohydride
4957:Pauson–Khand reaction
4525:11 April 2015 at the
4414:24 March 2016 at the
3964:The Planetary Society
3857:10.1093/femsec/fiy103
3814:Thorpe, Dave (2005).
3673:. BOC. Archived from
3671:Products and Services
3647:William Stanley Sykes
3431:"Alcohols, Aliphatic"
2421:10.1039/9781849733069
2415:. 2014. p. 375.
2280:
2258:
1878:incandescent lighting
1818:inhalation anesthetic
1647:
1601:Oxy-acetylene welding
978:
744:200.927 J·mol·K
110:Systematic IUPAC name
32:HCCH (disambiguation)
6484:Chemistry portal
6472:Astronomy portal
6418:RNA world hypothesis
6402:PAH world hypothesis
6095:Heptatrienyl radical
6027:Buckminsterfullerene
5915:Methylcyanoacetylene
5423:Silicon carbonitride
5398:Methylidynephosphane
5364:Magnesium isocyanide
5272:Aluminium isocyanide
5074:Carbon monophosphide
4967:Sonogashira coupling
4952:Diels–Alder reaction
4947:Alkyne trimerisation
4886:Corey–Fuchs reaction
3970:on 20 February 2012.
3947:on 23 February 2007.
3688:Geyh, Mebus (1990).
2793:13 July 2015 at the
2692:11 July 2012 at the
2211:
2060:alkyne trimerisation
1956:Vinylation reactions
1789:. Its reaction with
1506:, it possesses the D
1504:symmetrical molecule
1458:electric arc furnace
1397:Carbochemical method
961:(fire diamond)
793:209.879 kJ·mol
771:227.400 kJ·mol
720:44.036 J·mol·K
673:Thermal conductivity
98:Preferred IUPAC name
8880:Lanthanide hydrides
8487:(Group 17 hydrides)
8066:(Group 16 hydrides)
7520:(Group 15) hydrides
6362:Interstellar medium
6342:Forbidden mechanism
6155:Hydrogen isocyanide
5845:Hexatriynyl radical
5428:c-Silicon dicarbide
5333:Hydrogen isocyanide
5197:Silicon monosulfide
5172:Phosphorus monoxide
5140:Methylidyne radical
5099:Fluoromethylidynium
5059:Aluminium(II) oxide
4872:Dehydrohalogenation
4193:. CFC StarTec LLC.
4001:2007Natur.445..376S
3610:2007JChEd..84.1725P
3315:10 May 2020 at the
3202:Inorganic Chemistry
3101:12 May 2016 at the
3071:Transform Materials
2833:1961JChEd..38...83I
2314:Safety and handling
2283:New acetylene plant
2172:Acid-base reactions
2154:Copper(I) acetylide
2152:, are also common.
1898:acetylene hydratase
1764:mercury(II) bromide
1695:as the by-product.
1687:The reaction gives
1517:Physical properties
1478:valence bond theory
1462:hydroelectric power
1221:Marcellin Berthelot
1205:potassium carbonate
588:Solubility in water
525: g·mol
174:Beilstein Reference
52:
6536:(Group 1) hydrides
6382:Molecules in stars
6352:Intergalactic dust
6297:Circumstellar dust
6239:Naphthalene cation
6174:Trihydrogen cation
6150:Hydrogen deuteride
6075:Methyltriacetylene
5910:Hexapentaenylidene
5729:E-Cyanomethanimine
5649:Cyclopropenylidene
5583:Tricarbon monoxide
5573:Silicon tricarbide
5543:Methylene amidogen
5533:Isothiocyanic acid
5448:Thioxoethenylidene
5408:Trihydrogen cation
5222:Titanium(II) oxide
5182:Potassium chloride
5161:Sulfur mononitride
5104:Helium hydride ion
5079:Carbon monosulfide
4982:Favorskii reaction
4942:Thiol-yne reaction
4333:on 1 December 2016
3618:10.1021/ed084p1725
2732:6 May 2016 at the
2291:
2253:
1888:Natural occurrence
1832:radiocarbon dating
1777:of acetylene with
1750:Niche applications
1653:
1203:metal. By heating
1115:Infobox references
1074:(Immediate danger)
980:
50:
9284:
9283:
9109:Actinide hydrides
8485:Hydrogen halides
8447:
8412:
8411:
8382:
8381:
8359:
8358:
8323:
8322:
8285:
8284:
8146:
8145:
8052:
8018:
8017:
7988:
7987:
7965:
7964:
7942:
7941:
7905:
7904:
7852:
7851:
7714:
7713:
7661:
7660:
7512:
7511:
7469:
7468:
7446:
7445:
7409:
7408:
7336:
7335:
7302:
7301:
7273:
7272:
7135:
7134:
7093:
7092:
7038:Group 14 hydrides
7032:
7031:
6977:
6976:
6942:
6941:
6907:
6906:
6872:
6871:
6837:
6836:
6676:
6675:
6621:
6620:
6492:
6491:
6407:Pseudo-panspermia
6103:
6102:
6050:Cyanodecapentayne
5990:N-Methylformamide
5965:Methyldiacetylene
5890:Aminoacetonitrile
5860:Methyl isocyanate
5778:Methyl isocyanide
5659:Isocyanoacetylene
5639:Cyanoformaldehyde
5518:Hydrogen peroxide
5403:Potassium cyanide
5359:Magnesium cyanide
5312:Disilicon carbide
5307:Dicarbon monoxide
5114:Hydrogen fluoride
5109:Hydrogen chloride
4990:
4989:
4932:Hydrohalogenation
4546:Project Gutenberg
4268:978-0-7514-0352-7
4165:Organic Syntheses
4138:Organic Syntheses
3995:(7126): 376–377.
3939:(Press release).
3914:978-94-017-9268-4
3776:978-0-313-33758-1
3524:10.1021/cr400276u
3452:978-3-527-30673-2
3396:978-3-527-30673-2
3351:10.1021/cr400357r
3211:978-0-13-175553-6
3142:978-3-527-30673-2
3127:. pp. 1–14.
2868:Berthelot (1862)
2782:Bertholet (1860)
2706:General Chemistry
2626:General Chemistry
2590:978-1-4987-5428-6
2430:978-0-85404-182-4
2368:dimethylformamide
2298:Acetylene can be
2251:
2243:
2237:
2231:
2225:
2217:
2160:can be formed in
2064:cyclooctatetraene
2026:hydrochlorination
1844:mass spectrometer
1807:Alan G MacDiarmid
1693:propargyl alcohol
1633:explosively into
1557:dimethylformamide
1491:to form a strong
1209:potassium carbide
1160:and the simplest
1141:with the formula
1139:chemical compound
1123:Chemical compound
1121:
1120:
878:Hazard statements
820:1300 kJ·mol
778:Gibbs free energy
593:slightly soluble
402:CompTox Dashboard
387:(in mixture with
162:Interactive image
16:(Redirected from
9329:
9312:Industrial gases
8445:
8384:
8383:
8361:
8360:
8325:
8324:
8287:
8286:
8148:
8147:
8071:
8070:
8050:
7990:
7989:
7967:
7966:
7944:
7943:
7907:
7906:
7854:
7853:
7716:
7715:
7663:
7662:
7525:
7524:
7471:
7470:
7448:
7447:
7411:
7410:
7338:
7337:
7304:
7303:
7275:
7274:
7137:
7136:
7095:
7094:
7043:
7042:
6979:
6978:
6944:
6943:
6909:
6908:
6874:
6873:
6839:
6838:
6689:
6688:
6623:
6622:
6583:
6582:
6519:
6512:
6505:
6496:
6495:
6482:
6481:
6480:
6470:
6469:
6468:
6458:
6457:
6456:
6445:
6444:
6392:Organic compound
6292:Chemical formula
6197:Dihydroxyacetone
6145:Hydrogen cyanide
5830:Cyanodiacetylene
5684:Propadienylidene
5578:Thioformaldehyde
5453:Titanium dioxide
5418:Sodium hydroxide
5339:Hydrogen sulfide
5327:Hydrogen cyanide
5287:Carbonyl sulfide
5252:
5243:
5234:
5192:Silicon monoxide
5125:Hydroxyl radical
5037:
5036:
5017:
5010:
5003:
4994:
4993:
4817:
4800:
4771:
4754:
4720:
4691:
4662:
4645:
4628:
4598:
4591:
4584:
4575:
4574:
4548:
4507:
4506:
4504:
4502:
4487:
4481:
4480:
4478:
4476:
4461:
4452:
4451:
4449:
4447:
4441:
4434:
4425:
4419:
4406:
4400:
4399:
4397:
4395:
4380:
4369:
4368:
4366:
4364:
4349:
4343:
4342:
4340:
4338:
4332:
4326:. Archived from
4325:
4317:
4306:
4305:
4279:
4273:
4272:
4259:Industrial Gases
4254:
4248:
4247:
4245:
4243:
4237:
4230:
4222:
4207:
4206:
4204:
4202:
4187:
4181:
4180:
4160:
4154:
4153:
4129:
4123:
4122:
4110:
4100:
4091:
4090:
4070:
4064:
4063:
4037:
4031:
4030:
4012:
3978:
3972:
3971:
3966:. Archived from
3955:
3949:
3948:
3933:
3927:
3926:
3892:
3886:
3885:
3883:
3881:
3868:
3836:
3830:
3829:
3811:
3802:
3799:
3793:
3792:
3790:
3788:
3760:
3754:
3753:
3751:
3749:
3730:
3724:
3723:
3721:
3719:
3709:
3685:
3679:
3678:
3663:
3657:
3656:
3643:
3637:
3636:
3634:
3632:
3626:
3594:
3585:
3579:
3578:
3576:
3574:
3542:
3536:
3535:
3518:(3): 1743–1760.
3512:Chemical Reviews
3507:
3501:
3500:
3474:
3468:
3467:
3466:
3464:
3426:
3420:
3419:
3418:
3416:
3370:
3364:
3363:
3353:
3344:(3): 1761–1782.
3338:Chemical Reviews
3329:
3320:
3307:
3301:
3300:
3298:
3296:
3277:
3271:
3270:
3242:
3233:
3222:
3216:
3215:
3197:
3191:
3188:
3182:
3181:
3179:
3177:
3153:
3147:
3146:
3120:
3114:
3088:
3082:
3081:
3079:
3077:
3063:
3057:
3045:
3039:
3038:
3017:
3011:
3010:
2989:
2983:
2982:
2953:
2944:
2943:
2917:
2911:
2898:
2892:
2866:
2860:
2859:
2854:
2852:
2841:10.1021/ed038p83
2812:
2806:
2780:
2774:
2773:
2771:
2769:
2751:
2745:
2723:
2717:
2702:
2696:
2683:
2677:
2676:
2647:
2630:
2629:
2621:
2615:
2614:
2612:
2610:
2574:
2563:
2562:
2560:
2558:
2539:
2533:
2532:
2520:
2507:
2491:
2485:
2472:
2466:
2465:
2463:
2461:
2450:"P-14.3 Locants"
2445:
2439:
2438:
2405:
2300:semihydrogenated
2262:
2260:
2259:
2254:
2252:
2249:
2248:
2241:
2235:
2229:
2223:
2222:
2215:
2182:Acetylene has a
2158:silver acetylide
2151:
2129:
2125:
2121:
2085:
2078:
2040:transvinylations
2004:
1982:vinylpyrrolidone
1926:
1811:Hideki Shirakawa
1758:of acetylene to
1697:Copper acetylide
1683:
1593:dicyanoacetylene
1522:Changes of state
1436:Friedrich Wöhler
1430:
1331:, usually using
1155:
1151:
1105:
1099:
1096:
1095:
1025:Explosive limits
1000:
993:
986:
971:
951:
947:
943:
939:
935:
931:
927:
923:
919:
915:
911:
907:
903:
889:
885:
857:
852:
816:
789:
767:
740:
716:
701:Thermochemistry
666:
524:
509:
503:
496:Chemical formula
426:
425:
410:
408:
366:
330:
319:
305:
283:Gmelin Reference
266:
258:
247:
236:
216:
196:
164:
140:
87:
78:
69:
60:
53:
49:
21:
9337:
9336:
9332:
9331:
9330:
9328:
9327:
9326:
9322:Explosive gases
9287:
9286:
9285:
9280:
9262:
9258:
9250:
9242:
9234:
9226:
9218:
9210:
9202:
9194:
9186:
9178:
9170:
9162:
9154:
9147:
9143:
9136:
9128:
9120:
9103:
9099:
9091:
9083:
9075:
9067:
9059:
9051:
9043:
9035:
9027:
9019:
9011:
9003:
8995:
8987:
8979:
8971:
8963:
8955:
8947:
8939:
8931:
8923:
8915:
8907:
8899:
8891:
8874:
8864:
8855:
8847:
8843:
8830:
8822:
8791:
8777:
8762:
8747:
8739:
8731:
8723:
8715:
8702:
8694:
8681:
8668:
8655:
8642:
8634:
8626:
8618:
8610:
8602:
8594:
8586:
8578:
8570:
8562:
8554:
8546:
8529:
8486:
8479:
8474:
8465:
8442:
8433:
8425:
8408:
8398:
8378:
8374:
8355:
8351:
8347:
8338:
8319:
8315:
8311:
8302:
8281:
8272:
8268:
8260:
8256:
8248:
8244:
8236:
8232:
8224:
8220:
8212:
8208:
8200:
8196:
8188:
8184:
8176:
8172:
8163:
8142:
8134:
8130:
8122:
8118:
8110:
8106:
8098:
8094:
8085:
8065:
8063:
8056:
8048:
8039:
8026:
8014:
8004:
7984:
7980:
7961:
7957:
7938:
7934:
7930:
7922:
7901:
7897:
7893:
7885:
7881:
7873:
7869:
7848:
7839:
7835:
7827:
7823:
7815:
7811:
7803:
7799:
7791:
7787:
7779:
7775:
7767:
7763:
7755:
7751:
7743:
7739:
7731:
7710:
7706:
7702:
7694:
7690:
7682:
7678:
7657:
7648:
7644:
7636:
7632:
7624:
7620:
7612:
7608:
7600:
7596:
7588:
7584:
7576:
7572:
7564:
7560:
7552:
7548:
7540:
7519:
7508:
7504:
7496:
7465:
7461:
7442:
7438:
7434:
7426:
7405:
7401:
7397:
7389:
7385:
7377:
7373:
7365:
7361:
7353:
7332:
7323:
7319:
7298:
7294:
7290:
7269:
7260:
7256:
7248:
7244:
7236:
7232:
7224:
7220:
7212:
7208:
7200:
7196:
7188:
7184:
7176:
7172:
7164:
7160:
7152:
7131:
7126:
7118:
7110:
7089:
7028:
7024:
7016:
7012:
7004:
6973:
6969:
6965:
6957:
6938:
6934:
6930:
6922:
6903:
6899:
6895:
6887:
6868:
6864:
6860:
6852:
6833:
6829:
6825:
6817:
6813:
6805:
6801:
6793:
6789:
6781:
6777:
6769:
6765:
6757:
6753:
6745:
6741:
6733:
6729:
6721:
6717:
6704:
6683:
6672:
6668:
6660:
6652:
6644:
6636:
6617:
6577:
6575:
6568:
6535:
6528:
6523:
6493:
6488:
6478:
6476:
6466:
6464:
6454:
6452:
6432:
6258:
6234:
6225:
6178:
6168:
6111:
6099:
6080:Propionaldehyde
6055:Ethylene glycol
6044:
6036:
6032:
6003:
6001:
5994:
5950:Cyanohexatriyne
5936:
5929:
5876:
5869:
5804:
5797:
5757:
5710:
5703:
5674:Methoxy radical
5604:
5597:
5593:Thiocyanic acid
5474:
5467:
5377:
5317:Ethynyl radical
5253:
5247:
5246:
5245:
5244:
5238:
5237:
5236:
5235:
5226:
5217:Sulfur monoxide
5202:Sodium chloride
5187:Silicon carbide
5094:Diatomic carbon
5084:Carbon monoxide
5026:
5021:
4991:
4986:
4977:Glaser coupling
4895:
4850:Dehydrogenation
4833:
4816:
4812:
4808:
4799:
4795:
4791:
4770:
4766:
4762:
4753:
4749:
4745:
4719:
4715:
4711:
4690:
4686:
4682:
4661:
4657:
4653:
4644:
4640:
4636:
4627:
4623:
4619:
4607:
4602:
4538:
4527:Wayback Machine
4516:
4511:
4510:
4500:
4498:
4489:
4488:
4484:
4474:
4472:
4463:
4462:
4455:
4445:
4443:
4439:
4432:
4426:
4422:
4416:Wayback Machine
4407:
4403:
4393:
4391:
4382:
4381:
4372:
4362:
4360:
4351:
4350:
4346:
4336:
4334:
4330:
4323:
4319:
4318:
4309:
4294:
4280:
4276:
4269:
4255:
4251:
4241:
4239:
4235:
4228:
4224:
4223:
4210:
4200:
4198:
4189:
4188:
4184:
4161:
4157:
4130:
4126:
4119:
4101:
4094:
4081:(10): 727–733.
4071:
4067:
4060:
4038:
4034:
4010:10.1038/445376b
3979:
3975:
3956:
3952:
3935:
3934:
3930:
3915:
3893:
3889:
3879:
3877:
3837:
3833:
3826:
3812:
3805:
3800:
3796:
3786:
3784:
3777:
3761:
3757:
3747:
3745:
3732:
3731:
3727:
3717:
3715:
3686:
3682:
3677:on 17 May 2006.
3665:
3664:
3660:
3644:
3640:
3630:
3628:
3624:
3592:
3586:
3582:
3572:
3570:
3543:
3539:
3508:
3504:
3497:
3475:
3471:
3462:
3460:
3453:
3427:
3423:
3414:
3412:
3397:
3371:
3367:
3330:
3323:
3317:Wayback Machine
3308:
3304:
3294:
3292:
3279:
3278:
3274:
3267:
3243:
3236:
3223:
3219:
3212:
3198:
3194:
3189:
3185:
3175:
3173:
3154:
3150:
3143:
3121:
3117:
3103:Wayback Machine
3089:
3085:
3075:
3073:
3065:
3064:
3060:
3055:Wayback Machine
3046:
3042:
3018:
3014:
2990:
2986:
2979:
2954:
2947:
2940:
2918:
2914:
2908:Wayback Machine
2899:
2895:
2881:Wayback Machine
2867:
2863:
2850:
2848:
2813:
2809:
2795:Wayback Machine
2781:
2777:
2767:
2765:
2752:
2748:
2734:Wayback Machine
2724:
2720:
2703:
2699:
2694:Wayback Machine
2684:
2680:
2673:
2648:
2633:
2622:
2618:
2608:
2606:
2591:
2575:
2566:
2556:
2554:
2541:
2540:
2536:
2521:
2510:
2492:
2488:
2482:Wayback Machine
2473:
2469:
2459:
2457:
2446:
2442:
2431:
2407:
2406:
2402:
2397:
2361:
2320:calcium carbide
2316:
2296:
2244:
2218:
2214:
2212:
2209:
2208:
2190:
2180:
2174:
2149:
2145:
2139:
2127:
2123:
2120:
2116:
2112:
2108:
2104:
2100:
2096:
2092:
2088:
2052:
2030:oxychlorination
1958:
1953:
1924:
1920:
1916:
1912:
1908:
1890:
1840:lithium carbide
1752:
1740:
1738:Historical uses
1704:carbon monoxide
1658:
1570:
1565:
1549:
1524:
1519:
1509:
1489:orbital overlap
1474:
1429:
1425:
1421:
1417:
1413:
1409:
1403:calcium carbide
1399:
1388:
1384:
1380:
1376:
1370:
1366:
1362:
1358:
1354:
1345:
1306:
1302:
1298:
1294:
1290:
1273:
1261:
1234:
1230:
1218:
1214:
1193:
1166:divinyl sulfide
1153:
1150:
1146:
1142:
1131:systematic name
1124:
1117:
1112:
1111:
1110: ?)
1101:
1097:
1093:
1089:
1075:
1062:
1049:
1016:
1013:
1005:
1004:
1003:
1002:
995:
988:
981:
977:
969:
898:
880:
866:
845:
817:
814:
808:
804:
801:
800:Std enthalpy of
790:
784:
780:
768:
765:
759:
755:
752:
751:Std enthalpy of
741:
738:
731:
728:
717:
710:
691:
689:Molecular shape
664:
660:
636:
604:
590:
578:
575:
522:
512:
506:
498:
484:
481:
476:
475:
464:
461:
460:
457:
451:
450:
447:
441:
440:
429:
411:
404:
383:
369:
349:
333:
320:
308:
285:
276:
239:
219:
199:
176:
167:
154:
143:
130:
116:
115:
104:
103:
46:
35:
28:
23:
22:
15:
12:
11:
5:
9335:
9325:
9324:
9319:
9314:
9309:
9304:
9299:
9282:
9281:
9279:
9278:
9272:
9270:
9264:
9263:
9261:
9260:
9256:
9252:
9248:
9244:
9240:
9236:
9232:
9228:
9224:
9220:
9216:
9212:
9208:
9204:
9200:
9196:
9192:
9188:
9184:
9180:
9176:
9172:
9168:
9164:
9160:
9156:
9152:
9148:
9145:
9141:
9138:
9134:
9130:
9126:
9122:
9118:
9113:
9111:
9105:
9104:
9102:
9101:
9097:
9093:
9089:
9085:
9081:
9077:
9073:
9069:
9065:
9061:
9057:
9053:
9049:
9045:
9041:
9037:
9033:
9029:
9025:
9021:
9017:
9013:
9009:
9005:
9001:
8997:
8993:
8989:
8985:
8981:
8977:
8973:
8969:
8965:
8961:
8957:
8953:
8949:
8945:
8941:
8937:
8933:
8929:
8925:
8921:
8917:
8913:
8909:
8905:
8901:
8897:
8893:
8889:
8884:
8882:
8876:
8875:
8873:
8872:
8862:
8857:
8853:
8849:
8845:
8841:
8837:
8832:
8828:
8824:
8820:
8816:
8804:
8799:
8789:
8784:
8773:
8769:
8758:
8754:
8749:
8745:
8741:
8737:
8733:
8729:
8725:
8721:
8717:
8713:
8709:
8704:
8700:
8696:
8692:
8688:
8683:
8679:
8675:
8670:
8666:
8662:
8657:
8653:
8649:
8644:
8640:
8636:
8632:
8628:
8624:
8620:
8616:
8612:
8608:
8604:
8600:
8596:
8592:
8588:
8584:
8580:
8576:
8572:
8568:
8564:
8560:
8556:
8552:
8548:
8544:
8539:
8537:
8531:
8530:
8528:
8516:
8511:
8506:
8501:
8496:
8491:
8489:
8481:
8480:
8478:
8477:
8472:
8468:
8463:
8459:
8454:
8449:
8440:
8435:
8431:
8427:
8423:
8419:
8413:
8410:
8409:
8407:
8406:
8396:
8390:
8388:
8380:
8379:
8377:
8376:
8372:
8367:
8365:
8357:
8356:
8354:
8353:
8349:
8345:
8341:
8336:
8331:
8329:
8321:
8320:
8318:
8317:
8313:
8309:
8305:
8300:
8295:
8293:
8283:
8282:
8280:
8279:
8274:
8270:
8266:
8262:
8258:
8254:
8250:
8246:
8242:
8238:
8234:
8230:
8226:
8222:
8218:
8214:
8210:
8206:
8202:
8198:
8194:
8190:
8186:
8182:
8178:
8174:
8170:
8166:
8161:
8156:
8154:
8144:
8143:
8141:
8136:
8132:
8128:
8124:
8120:
8116:
8112:
8108:
8104:
8100:
8096:
8092:
8088:
8083:
8079:
8077:
8068:
8064:chalcogenides
8058:
8057:
8055:
8054:
8046:
8041:
8037:
8033:
8028:
8024:
8019:
8016:
8015:
8013:
8012:
8002:
7996:
7994:
7986:
7985:
7983:
7982:
7978:
7973:
7971:
7963:
7962:
7960:
7959:
7955:
7950:
7948:
7940:
7939:
7937:
7936:
7932:
7928:
7924:
7920:
7915:
7913:
7903:
7902:
7900:
7899:
7895:
7891:
7887:
7883:
7879:
7875:
7871:
7867:
7862:
7860:
7850:
7849:
7847:
7846:
7841:
7837:
7833:
7829:
7825:
7821:
7817:
7813:
7809:
7805:
7801:
7797:
7793:
7789:
7785:
7781:
7777:
7773:
7769:
7765:
7761:
7757:
7753:
7749:
7745:
7741:
7737:
7733:
7729:
7724:
7722:
7712:
7711:
7709:
7708:
7704:
7700:
7696:
7692:
7688:
7684:
7680:
7676:
7671:
7669:
7659:
7658:
7656:
7655:
7650:
7646:
7642:
7638:
7634:
7630:
7626:
7622:
7618:
7614:
7610:
7606:
7602:
7598:
7594:
7590:
7586:
7582:
7578:
7574:
7570:
7566:
7562:
7558:
7554:
7550:
7546:
7542:
7538:
7533:
7531:
7522:
7514:
7513:
7510:
7509:
7507:
7506:
7502:
7498:
7494:
7490:
7484:
7482:
7467:
7466:
7464:
7463:
7459:
7454:
7452:
7444:
7443:
7441:
7440:
7436:
7432:
7428:
7424:
7419:
7417:
7407:
7406:
7404:
7403:
7399:
7395:
7391:
7387:
7383:
7379:
7375:
7371:
7367:
7363:
7359:
7355:
7351:
7346:
7344:
7334:
7333:
7331:
7330:
7325:
7321:
7317:
7312:
7310:
7300:
7299:
7297:
7296:
7292:
7288:
7283:
7281:
7271:
7270:
7268:
7267:
7262:
7258:
7254:
7250:
7246:
7242:
7238:
7234:
7230:
7226:
7222:
7218:
7214:
7210:
7206:
7202:
7198:
7194:
7190:
7186:
7182:
7178:
7174:
7170:
7166:
7162:
7158:
7154:
7150:
7145:
7143:
7133:
7132:
7130:
7129:
7124:
7120:
7116:
7112:
7108:
7104:
7098:
7091:
7090:
7088:
7087:
7082:
7077:
7072:
7067:
7062:
7057:
7051:
7049:
7040:
7034:
7033:
7030:
7029:
7027:
7026:
7022:
7018:
7014:
7010:
7006:
7002:
6998:
6992:
6990:
6975:
6974:
6972:
6971:
6967:
6963:
6959:
6955:
6950:
6948:
6940:
6939:
6937:
6936:
6932:
6928:
6924:
6920:
6915:
6913:
6905:
6904:
6902:
6901:
6897:
6893:
6889:
6885:
6880:
6878:
6870:
6869:
6867:
6866:
6862:
6858:
6854:
6850:
6845:
6843:
6835:
6834:
6832:
6831:
6827:
6823:
6819:
6815:
6811:
6807:
6803:
6799:
6795:
6791:
6787:
6783:
6779:
6775:
6771:
6767:
6763:
6759:
6755:
6751:
6747:
6743:
6739:
6735:
6731:
6727:
6723:
6719:
6715:
6711:
6706:
6702:
6697:
6695:
6686:
6678:
6677:
6674:
6673:
6671:
6670:
6666:
6662:
6658:
6654:
6650:
6646:
6642:
6638:
6634:
6629:
6627:
6619:
6618:
6616:
6615:
6610:
6605:
6600:
6595:
6589:
6587:
6580:
6578:earth hydrides
6570:
6569:
6567:
6566:
6561:
6556:
6551:
6546:
6540:
6538:
6530:
6529:
6522:
6521:
6514:
6507:
6499:
6490:
6489:
6487:
6486:
6474:
6462:
6450:
6437:
6434:
6433:
6431:
6430:
6425:
6420:
6415:
6409:
6404:
6399:
6394:
6389:
6384:
6379:
6374:
6369:
6364:
6359:
6354:
6349:
6344:
6339:
6334:
6329:
6324:
6319:
6317:Cosmochemistry
6314:
6309:
6304:
6299:
6294:
6289:
6284:
6282:Astrochemistry
6279:
6274:
6268:
6266:
6260:
6259:
6257:
6256:
6251:
6246:
6241:
6236:
6232:
6228:
6223:
6219:
6214:
6209:
6204:
6199:
6194:
6188:
6186:
6180:
6179:
6177:
6176:
6171:
6166:
6162:
6157:
6152:
6147:
6142:
6137:
6135:Formyl radical
6132:
6127:
6121:
6115:
6113:
6105:
6104:
6101:
6100:
6098:
6097:
6092:
6087:
6082:
6077:
6072:
6067:
6065:Methyl acetate
6062:
6057:
6052:
6047:
6042:
6038:
6034:
6030:
6024:
6019:
6014:
6008:
6006:
5996:
5995:
5993:
5992:
5987:
5982:
5977:
5972:
5967:
5962:
5957:
5955:Dimethyl ether
5952:
5947:
5941:
5939:
5931:
5930:
5928:
5927:
5922:
5920:Methyl formate
5917:
5912:
5907:
5905:Glycolaldehyde
5902:
5897:
5892:
5887:
5881:
5879:
5871:
5870:
5868:
5867:
5862:
5857:
5852:
5847:
5842:
5840:Glycolonitrile
5837:
5835:Ethylene oxide
5832:
5827:
5826:
5825:
5815:
5809:
5807:
5799:
5798:
5796:
5795:
5790:
5785:
5780:
5775:
5770:
5765:
5760:
5755:
5751:
5746:
5741:
5736:
5734:Cyclopropenone
5731:
5726:
5721:
5715:
5713:
5705:
5704:
5702:
5701:
5696:
5691:
5686:
5681:
5676:
5671:
5666:
5661:
5656:
5651:
5646:
5641:
5636:
5634:Cyanoacetylene
5631:
5626:
5621:
5616:
5609:
5607:
5599:
5598:
5596:
5595:
5590:
5585:
5580:
5575:
5570:
5565:
5560:
5555:
5553:Methyl radical
5550:
5545:
5540:
5535:
5530:
5528:Isocyanic acid
5525:
5520:
5515:
5510:
5505:
5500:
5495:
5493:Isocyanic acid
5490:
5485:
5479:
5477:
5469:
5468:
5466:
5465:
5460:
5455:
5450:
5445:
5440:
5438:Sulfur dioxide
5435:
5430:
5425:
5420:
5415:
5413:Sodium cyanide
5410:
5405:
5400:
5395:
5390:
5385:
5380:
5375:
5371:
5366:
5361:
5356:
5351:
5346:
5341:
5336:
5330:
5324:
5322:Formyl radical
5319:
5314:
5309:
5304:
5299:
5294:
5289:
5284:
5282:Carbon dioxide
5279:
5274:
5269:
5263:
5261:
5255:
5254:
5229:
5227:
5225:
5224:
5219:
5214:
5209:
5204:
5199:
5194:
5189:
5184:
5179:
5174:
5169:
5163:
5158:
5153:
5147:
5142:
5137:
5132:
5130:Iron(II) oxide
5127:
5122:
5116:
5111:
5106:
5101:
5096:
5091:
5086:
5081:
5076:
5071:
5066:
5061:
5056:
5051:
5045:
5043:
5034:
5028:
5027:
5020:
5019:
5012:
5005:
4997:
4988:
4987:
4985:
4984:
4979:
4974:
4969:
4964:
4959:
4954:
4949:
4944:
4939:
4934:
4929:
4924:
4919:
4914:
4909:
4903:
4901:
4897:
4896:
4894:
4893:
4888:
4883:
4878:
4869:
4860:
4847:
4841:
4839:
4835:
4834:
4832:
4831:
4830:
4829:
4824:
4814:
4810:
4802:
4797:
4793:
4785:
4784:
4783:
4778:
4768:
4764:
4756:
4751:
4747:
4739:
4738:
4737:
4732:
4727:
4717:
4713:
4705:
4704:
4703:
4698:
4688:
4684:
4676:
4675:
4674:
4669:
4659:
4655:
4647:
4642:
4638:
4630:
4625:
4621:
4612:
4609:
4608:
4601:
4600:
4593:
4586:
4578:
4572:
4571:
4566:
4554:
4549:
4536:
4534:
4529:
4515:
4514:External links
4512:
4509:
4508:
4482:
4453:
4420:
4401:
4370:
4344:
4307:
4292:
4274:
4267:
4249:
4208:
4182:
4155:
4124:
4118:978-0824716752
4117:
4092:
4065:
4058:
4032:
3973:
3950:
3928:
3913:
3887:
3831:
3825:978-0976090526
3824:
3803:
3794:
3775:
3755:
3725:
3700:(3): 321–324.
3680:
3658:
3638:
3598:J. Chem. Educ.
3580:
3537:
3502:
3495:
3469:
3451:
3421:
3395:
3365:
3321:
3302:
3272:
3266:978-3527306732
3265:
3234:
3217:
3210:
3192:
3183:
3148:
3141:
3115:
3090:Wohler (1862)
3083:
3067:"How it Works"
3058:
3040:
3029:(5): 253–258.
3012:
3001:(5): 245–253.
2984:
2978:978-3527306732
2977:
2945:
2938:
2912:
2893:
2885:Comptes rendus
2861:
2807:
2799:Comptes rendus
2775:
2746:
2718:
2697:
2678:
2672:978-3527306732
2671:
2631:
2616:
2589:
2564:
2534:
2508:
2486:
2467:
2440:
2429:
2399:
2398:
2396:
2393:
2376:porous filling
2359:
2356:gauge pressure
2344:vinylacetylene
2315:
2312:
2295:
2292:
2268:organometallic
2264:
2263:
2247:
2240:
2234:
2228:
2221:
2188:
2176:Main article:
2173:
2170:
2147:
2141:
2132:
2131:
2118:
2114:
2110:
2106:
2102:
2098:
2094:
2090:
2086:
2079:
2051:
2048:
2022:vinyl chloride
2014:Wacker process
2006:
2005:
1986:vinylcarbazole
1957:
1954:
1952:
1949:
1928:
1927:
1922:
1918:
1914:
1910:
1889:
1886:
1803:Alan J. Heeger
1775:polymerization
1768:Wacker process
1751:
1748:
1739:
1736:
1732:vinyl chloride
1712:acrylic fibers
1685:
1684:
1657:
1654:
1569:
1566:
1564:
1561:
1548:
1545:
1523:
1520:
1518:
1515:
1507:
1493:σ valence bond
1473:
1470:
1432:
1431:
1427:
1423:
1419:
1415:
1411:
1398:
1395:
1390:
1389:
1386:
1382:
1378:
1374:
1371:
1368:
1364:
1360:
1356:
1352:
1344:
1341:
1309:
1308:
1304:
1300:
1296:
1292:
1288:
1272:
1269:
1260:
1257:
1232:
1228:
1216:
1212:
1192:
1189:
1183:together in a
1152:and structure
1148:
1144:
1122:
1119:
1118:
1113:
1091:
1090:
1086:standard state
1083:
1080:
1079:
1076:
1070:
1067:
1066:
1063:
1057:
1054:
1053:
1050:
1044:
1041:
1040:
1031:
1030:
1027:
1021:
1020:
1017:
1010:
1007:
1006:
996:
989:
982:
967:
966:
965:
964:
962:
953:
952:
899:
894:
891:
890:
881:
876:
873:
872:
867:
862:
859:
858:
846:
841:
838:
837:
827:
826:
822:
821:
818:
812:
806:
798:
795:
794:
791:
782:
776:
773:
772:
769:
763:
757:
749:
746:
745:
742:
736:
725:
722:
721:
718:
706:
703:
702:
698:
697:
692:
687:
684:
683:
679:
678:
675:
669:
668:
661:
655:
652:
651:
648:
646:Conjugate acid
642:
641:
638:
634:
624:
623:
620:
618:Vapor pressure
614:
613:
601:
595:
594:
591:
586:
583:
582:
579:
572:
569:
568:
561:
555:
554:
551:
545:
544:
541:
535:
534:
533:Colorless gas
531:
527:
526:
520:
514:
513:
510:
504:
499:
494:
491:
490:
486:
485:
483:
482:
479:
471:
470:
469:
466:
465:
463:
462:
458:
455:
454:
452:
448:
445:
444:
436:
435:
434:
431:
430:
428:
427:
414:
412:
400:
397:
396:
377:
371:
370:
368:
367:
359:
357:
351:
350:
348:
347:
343:
341:
335:
334:
332:
331:
323:
321:
313:
310:
309:
307:
306:
298:
296:
290:
289:
286:
281:
278:
277:
275:
274:
270:
268:
260:
259:
249:
241:
240:
238:
237:
229:
227:
221:
220:
218:
217:
209:
207:
201:
200:
198:
197:
189:
187:
181:
180:
177:
172:
169:
168:
166:
165:
157:
155:
148:
145:
144:
142:
141:
133:
131:
126:
123:
122:
118:
117:
113:
112:
106:
105:
101:
100:
94:
93:
89:
88:
80:
79:
71:
70:
62:
61:
26:
9:
6:
4:
3:
2:
9334:
9323:
9320:
9318:
9315:
9313:
9310:
9308:
9305:
9303:
9300:
9298:
9295:
9294:
9292:
9277:
9274:
9273:
9271:
9269:
9265:
9259:
9253:
9251:
9245:
9243:
9237:
9235:
9229:
9227:
9221:
9219:
9213:
9211:
9205:
9203:
9197:
9195:
9189:
9187:
9181:
9179:
9173:
9171:
9165:
9163:
9157:
9155:
9149:
9139:
9137:
9131:
9129:
9123:
9121:
9115:
9114:
9112:
9110:
9106:
9100:
9094:
9092:
9086:
9084:
9078:
9076:
9070:
9068:
9062:
9060:
9054:
9052:
9046:
9044:
9038:
9036:
9030:
9028:
9022:
9020:
9014:
9012:
9006:
9004:
8998:
8996:
8990:
8988:
8982:
8980:
8974:
8972:
8966:
8964:
8958:
8956:
8950:
8948:
8942:
8940:
8934:
8932:
8926:
8924:
8918:
8916:
8910:
8908:
8902:
8900:
8894:
8892:
8886:
8885:
8883:
8881:
8877:
8870:
8866:
8865:
8858:
8856:
8850:
8848:
8838:
8836:
8833:
8831:
8825:
8823:
8817:
8814:
8810:
8809:
8805:
8803:
8800:
8797:
8793:
8792:
8785:
8783:
8781:
8776:
8770:
8768:
8766:
8761:
8755:
8753:
8750:
8748:
8742:
8740:
8734:
8732:
8726:
8724:
8718:
8716:
8710:
8708:
8705:
8703:
8697:
8695:
8689:
8687:
8684:
8682:
8676:
8674:
8671:
8669:
8663:
8661:
8658:
8656:
8650:
8648:
8645:
8643:
8637:
8635:
8629:
8627:
8621:
8619:
8613:
8611:
8605:
8603:
8597:
8595:
8589:
8587:
8581:
8579:
8573:
8571:
8565:
8563:
8557:
8555:
8549:
8547:
8541:
8540:
8538:
8536:
8532:
8526:
8522:
8521:
8517:
8515:
8512:
8510:
8507:
8505:
8502:
8500:
8497:
8495:
8492:
8490:
8488:
8482:
8476:
8469:
8467:
8460:
8458:
8455:
8453:
8450:
8448:
8444:
8436:
8434:
8428:
8426:
8420:
8418:
8415:
8414:
8404:
8400:
8399:
8392:
8391:
8389:
8385:
8375:
8369:
8368:
8366:
8362:
8352:
8342:
8340:
8333:
8332:
8330:
8326:
8316:
8306:
8304:
8297:
8296:
8294:
8292:
8288:
8278:
8275:
8273:
8263:
8261:
8251:
8249:
8239:
8237:
8227:
8225:
8215:
8213:
8203:
8201:
8191:
8189:
8179:
8177:
8167:
8165:
8158:
8157:
8155:
8153:
8149:
8140:
8137:
8135:
8125:
8123:
8113:
8111:
8101:
8099:
8089:
8087:
8080:
8078:
8076:
8072:
8069:
8067:
8059:
8053:
8049:
8042:
8040:
8034:
8032:
8029:
8027:
8021:
8020:
8010:
8006:
8005:
7998:
7997:
7995:
7991:
7981:
7975:
7974:
7972:
7968:
7958:
7952:
7951:
7949:
7945:
7935:
7925:
7923:
7917:
7916:
7914:
7912:
7908:
7898:
7888:
7886:
7876:
7874:
7864:
7863:
7861:
7859:
7855:
7845:
7842:
7840:
7830:
7828:
7818:
7816:
7806:
7804:
7794:
7792:
7782:
7780:
7770:
7768:
7758:
7756:
7746:
7744:
7734:
7732:
7726:
7725:
7723:
7721:
7717:
7707:
7697:
7695:
7685:
7683:
7673:
7672:
7670:
7668:
7664:
7654:
7651:
7649:
7639:
7637:
7627:
7625:
7615:
7613:
7603:
7601:
7591:
7589:
7579:
7577:
7567:
7565:
7555:
7553:
7543:
7541:
7535:
7534:
7532:
7530:
7526:
7523:
7521:
7515:
7505:
7499:
7497:
7491:
7489:
7486:
7485:
7483:
7480:
7476:
7472:
7462:
7456:
7455:
7453:
7449:
7439:
7429:
7427:
7421:
7420:
7418:
7416:
7412:
7402:
7392:
7390:
7380:
7378:
7368:
7366:
7356:
7354:
7348:
7347:
7345:
7343:
7339:
7329:
7326:
7324:
7314:
7313:
7311:
7309:
7305:
7295:
7285:
7284:
7282:
7280:
7276:
7266:
7263:
7261:
7251:
7249:
7239:
7237:
7227:
7225:
7215:
7213:
7203:
7201:
7191:
7189:
7179:
7177:
7167:
7165:
7155:
7153:
7147:
7146:
7144:
7142:
7138:
7128:
7121:
7119:
7113:
7111:
7105:
7103:
7100:
7099:
7096:
7086:
7083:
7081:
7078:
7076:
7073:
7071:
7068:
7066:
7063:
7061:
7058:
7056:
7053:
7052:
7050:
7048:
7044:
7041:
7039:
7035:
7025:
7019:
7017:
7007:
7005:
6999:
6997:
6994:
6993:
6991:
6988:
6984:
6980:
6970:
6960:
6958:
6952:
6951:
6949:
6945:
6935:
6925:
6923:
6917:
6916:
6914:
6910:
6900:
6890:
6888:
6882:
6881:
6879:
6875:
6865:
6855:
6853:
6847:
6846:
6844:
6840:
6830:
6820:
6818:
6808:
6806:
6796:
6794:
6784:
6782:
6772:
6770:
6760:
6758:
6748:
6746:
6736:
6734:
6724:
6722:
6712:
6710:
6707:
6705:
6699:
6698:
6696:
6694:
6690:
6687:
6685:
6679:
6669:
6663:
6661:
6655:
6653:
6647:
6645:
6639:
6637:
6631:
6630:
6628:
6624:
6614:
6611:
6609:
6606:
6604:
6601:
6599:
6596:
6594:
6591:
6590:
6588:
6584:
6581:
6579:
6571:
6565:
6562:
6560:
6557:
6555:
6552:
6550:
6547:
6545:
6542:
6541:
6539:
6537:
6534:Alkali metal
6531:
6527:
6520:
6515:
6513:
6508:
6506:
6501:
6500:
6497:
6485:
6475:
6473:
6463:
6461:
6451:
6449:
6448:
6439:
6438:
6435:
6429:
6426:
6424:
6421:
6419:
6416:
6413:
6410:
6408:
6405:
6403:
6400:
6398:
6395:
6393:
6390:
6388:
6385:
6383:
6380:
6378:
6375:
6373:
6370:
6368:
6365:
6363:
6360:
6358:
6355:
6353:
6350:
6348:
6347:Homochirality
6345:
6343:
6340:
6338:
6335:
6333:
6330:
6328:
6325:
6323:
6320:
6318:
6315:
6313:
6310:
6308:
6305:
6303:
6300:
6298:
6295:
6293:
6290:
6288:
6285:
6283:
6280:
6278:
6275:
6273:
6270:
6269:
6267:
6265:
6261:
6255:
6252:
6250:
6247:
6245:
6242:
6240:
6237:
6235:
6229:
6227:
6220:
6218:
6215:
6213:
6210:
6208:
6205:
6203:
6202:Methoxyethane
6200:
6198:
6195:
6193:
6190:
6189:
6187:
6185:
6181:
6175:
6172:
6170:
6163:
6161:
6158:
6156:
6153:
6151:
6148:
6146:
6143:
6141:
6138:
6136:
6133:
6131:
6128:
6125:
6122:
6120:
6117:
6116:
6114:
6110:
6106:
6096:
6093:
6091:
6088:
6086:
6085:Butyronitrile
6083:
6081:
6078:
6076:
6073:
6071:
6068:
6066:
6063:
6061:
6060:Ethyl formate
6058:
6056:
6053:
6051:
6048:
6046:
6039:
6028:
6025:
6023:
6020:
6018:
6015:
6013:
6010:
6009:
6007:
6005:
5997:
5991:
5988:
5986:
5985:Propionitrile
5983:
5981:
5978:
5976:
5973:
5971:
5968:
5966:
5963:
5961:
5958:
5956:
5953:
5951:
5948:
5946:
5943:
5942:
5940:
5938:
5932:
5926:
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5882:
5880:
5878:
5872:
5866:
5865:Vinyl alcohol
5863:
5861:
5858:
5856:
5853:
5851:
5848:
5846:
5843:
5841:
5838:
5836:
5833:
5831:
5828:
5824:
5823:Vinyl cyanide
5821:
5820:
5819:
5818:Acrylonitrile
5816:
5814:
5811:
5810:
5808:
5806:
5800:
5794:
5791:
5789:
5786:
5784:
5783:Pentynylidyne
5781:
5779:
5776:
5774:
5771:
5769:
5766:
5764:
5761:
5759:
5752:
5750:
5747:
5745:
5742:
5740:
5737:
5735:
5732:
5730:
5727:
5725:
5722:
5720:
5717:
5716:
5714:
5712:
5706:
5700:
5697:
5695:
5692:
5690:
5687:
5685:
5682:
5680:
5679:Methylenimine
5677:
5675:
5672:
5670:
5667:
5665:
5662:
5660:
5657:
5655:
5652:
5650:
5647:
5645:
5642:
5640:
5637:
5635:
5632:
5630:
5627:
5625:
5622:
5620:
5617:
5614:
5611:
5610:
5608:
5606:
5600:
5594:
5591:
5589:
5586:
5584:
5581:
5579:
5576:
5574:
5571:
5569:
5566:
5564:
5561:
5559:
5558:Propynylidyne
5556:
5554:
5551:
5549:
5548:Methyl cation
5546:
5544:
5541:
5539:
5536:
5534:
5531:
5529:
5526:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5508:Fulminic acid
5506:
5504:
5501:
5499:
5496:
5494:
5491:
5489:
5486:
5484:
5481:
5480:
5478:
5476:
5470:
5464:
5461:
5459:
5456:
5454:
5451:
5449:
5446:
5444:
5441:
5439:
5436:
5434:
5431:
5429:
5426:
5424:
5421:
5419:
5416:
5414:
5411:
5409:
5406:
5404:
5401:
5399:
5396:
5394:
5391:
5389:
5386:
5384:
5383:Nitrous oxide
5381:
5379:
5372:
5370:
5367:
5365:
5362:
5360:
5357:
5355:
5352:
5350:
5347:
5345:
5342:
5340:
5337:
5334:
5331:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5280:
5278:
5277:Amino radical
5275:
5273:
5270:
5268:
5265:
5264:
5262:
5260:
5256:
5251:
5242:
5233:
5223:
5220:
5218:
5215:
5213:
5210:
5208:
5207:Sodium iodide
5205:
5203:
5200:
5198:
5195:
5193:
5190:
5188:
5185:
5183:
5180:
5178:
5175:
5173:
5170:
5167:
5164:
5162:
5159:
5157:
5154:
5151:
5148:
5146:
5143:
5141:
5138:
5136:
5133:
5131:
5128:
5126:
5123:
5120:
5117:
5115:
5112:
5110:
5107:
5105:
5102:
5100:
5097:
5095:
5092:
5090:
5089:Cyano radical
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5069:Carbon cation
5067:
5065:
5062:
5060:
5057:
5055:
5052:
5050:
5047:
5046:
5044:
5042:
5038:
5035:
5033:
5029:
5025:
5018:
5013:
5011:
5006:
5004:
4999:
4998:
4995:
4983:
4980:
4978:
4975:
4973:
4970:
4968:
4965:
4963:
4960:
4958:
4955:
4953:
4950:
4948:
4945:
4943:
4940:
4938:
4935:
4933:
4930:
4928:
4927:Hydroboration
4925:
4923:
4920:
4918:
4915:
4913:
4912:Hydrogenation
4910:
4908:
4907:Deprotonation
4905:
4904:
4902:
4898:
4892:
4889:
4887:
4884:
4882:
4879:
4877:
4873:
4870:
4868:
4867:alkynyl anion
4864:
4861:
4859:
4855:
4851:
4848:
4846:
4843:
4842:
4840:
4836:
4828:
4825:
4823:
4820:
4819:
4806:
4803:
4789:
4786:
4782:
4779:
4777:
4774:
4773:
4760:
4757:
4743:
4740:
4736:
4733:
4731:
4728:
4726:
4723:
4722:
4709:
4706:
4702:
4699:
4697:
4694:
4693:
4680:
4677:
4673:
4670:
4668:
4665:
4664:
4651:
4648:
4634:
4631:
4617:
4614:
4613:
4610:
4606:
4599:
4594:
4592:
4587:
4585:
4580:
4579:
4576:
4570:
4567:
4564:
4563:
4558:
4555:
4553:
4550:
4547:
4543:
4542:
4537:
4535:
4533:
4530:
4528:
4524:
4521:
4518:
4517:
4496:
4492:
4486:
4470:
4466:
4460:
4458:
4438:
4431:
4424:
4417:
4413:
4410:
4405:
4389:
4385:
4379:
4377:
4375:
4358:
4354:
4348:
4329:
4322:
4316:
4314:
4312:
4303:
4299:
4295:
4293:83-11-07044-X
4289:
4285:
4278:
4270:
4264:
4260:
4253:
4234:
4227:
4221:
4219:
4217:
4215:
4213:
4196:
4192:
4186:
4178:
4174:
4170:
4166:
4159:
4151:
4147:
4143:
4139:
4135:
4128:
4120:
4114:
4109:
4108:
4099:
4097:
4088:
4084:
4080:
4076:
4069:
4061:
4055:
4051:
4047:
4043:
4036:
4028:
4024:
4020:
4016:
4011:
4006:
4002:
3998:
3994:
3990:
3989:
3984:
3977:
3969:
3965:
3961:
3954:
3946:
3942:
3938:
3932:
3924:
3920:
3916:
3910:
3906:
3902:
3898:
3891:
3876:
3872:
3867:
3862:
3858:
3854:
3850:
3846:
3842:
3835:
3827:
3821:
3817:
3810:
3808:
3798:
3782:
3778:
3772:
3768:
3767:
3759:
3743:
3739:
3735:
3729:
3713:
3708:
3703:
3699:
3695:
3691:
3684:
3676:
3672:
3668:
3662:
3654:
3653:
3648:
3642:
3623:
3619:
3615:
3611:
3607:
3603:
3600:
3599:
3591:
3584:
3568:
3564:
3560:
3557:: 1540–1542.
3556:
3552:
3548:
3541:
3533:
3529:
3525:
3521:
3517:
3513:
3506:
3498:
3492:
3488:
3484:
3480:
3473:
3458:
3454:
3448:
3444:
3440:
3436:
3432:
3425:
3410:
3406:
3402:
3398:
3392:
3388:
3384:
3380:
3376:
3369:
3361:
3357:
3352:
3347:
3343:
3339:
3335:
3328:
3326:
3318:
3314:
3311:
3306:
3290:
3286:
3282:
3276:
3268:
3262:
3258:
3254:
3250:
3249:
3241:
3239:
3231:
3227:
3221:
3213:
3207:
3203:
3196:
3187:
3171:
3167:
3163:
3159:
3152:
3144:
3138:
3134:
3130:
3126:
3119:
3112:
3108:
3104:
3100:
3097:
3095:
3087:
3072:
3068:
3062:
3056:
3052:
3049:
3044:
3036:
3032:
3028:
3024:
3016:
3008:
3004:
3000:
2996:
2988:
2980:
2974:
2970:
2966:
2962:
2961:
2952:
2950:
2941:
2939:9780471484943
2935:
2931:
2927:
2923:
2916:
2909:
2905:
2902:
2897:
2890:
2886:
2882:
2878:
2875:
2873:
2865:
2858:
2846:
2842:
2838:
2834:
2830:
2826:
2822:
2818:
2811:
2804:
2800:
2796:
2792:
2789:
2787:
2779:
2763:
2759:
2758:
2750:
2743:
2739:
2735:
2731:
2728:
2722:
2715:
2714:0-03-072373-6
2711:
2707:
2701:
2695:
2691:
2688:
2682:
2674:
2668:
2664:
2660:
2656:
2655:
2646:
2644:
2642:
2640:
2638:
2636:
2627:
2620:
2604:
2600:
2596:
2592:
2586:
2582:
2581:
2573:
2571:
2569:
2552:
2548:
2544:
2538:
2530:
2526:
2519:
2517:
2515:
2513:
2506:
2502:
2498:
2497:
2490:
2483:
2479:
2476:
2471:
2455:
2451:
2444:
2437:
2432:
2426:
2422:
2418:
2414:
2411:. Cambridge:
2410:
2404:
2400:
2392:
2388:
2386:
2382:
2379:
2377:
2373:
2369:
2365:
2357:
2353:
2349:
2345:
2341:
2337:
2333:
2329:
2325:
2321:
2311:
2309:
2305:
2301:
2294:Hydrogenation
2288:
2284:
2279:
2275:
2273:
2269:
2245:
2238:
2226:
2219:
2207:
2206:
2205:
2203:
2199:
2195:
2191:
2187:
2179:
2169:
2167:
2163:
2159:
2155:
2144:
2137:
2087:
2084:
2080:
2077:
2073:
2072:
2071:
2069:
2065:
2061:
2057:
2047:
2045:
2044:vinyl formate
2041:
2037:
2036:Vinyl acetate
2033:
2032:of ethylene.
2031:
2027:
2023:
2019:
2015:
2011:
2003:
1999:
1998:
1997:
1995:
1991:
1990:2-pyrrolidone
1987:
1983:
1979:
1975:
1971:
1967:
1963:
1948:
1945:
1941:
1937:
1933:
1907:
1906:
1905:
1903:
1899:
1896:
1885:
1883:
1882:electric grid
1879:
1875:
1871:
1868:
1864:
1860:
1859:street lights
1856:
1852:
1851:carbide lamps
1847:
1845:
1841:
1837:
1833:
1828:
1826:
1825:carburization
1821:
1819:
1814:
1812:
1808:
1804:
1800:
1796:
1792:
1788:
1784:
1783:polyacetylene
1780:
1776:
1771:
1769:
1765:
1761:
1757:
1747:
1745:
1735:
1733:
1729:
1725:
1721:
1717:
1713:
1709:
1705:
1700:
1698:
1694:
1690:
1682:
1678:
1677:
1676:
1674:
1670:
1666:
1661:
1651:
1646:
1642:
1640:
1636:
1632:
1629:), acetylene
1628:
1623:
1619:
1615:
1610:
1606:
1602:
1598:
1594:
1590:
1586:
1582:
1579:
1575:
1560:
1558:
1554:
1544:
1542:
1538:
1533:
1532:phase diagram
1529:
1514:
1512:
1505:
1500:
1498:
1494:
1490:
1486:
1483:
1479:
1469:
1467:
1466:Niagara Falls
1463:
1459:
1454:
1452:
1448:
1444:
1439:
1437:
1408:
1407:
1406:
1404:
1394:
1372:
1350:
1349:
1348:
1340:
1338:
1334:
1330:
1326:
1322:
1318:
1314:
1286:
1285:
1284:
1282:
1278:
1268:
1266:
1256:
1254:
1250:
1246:
1242:
1238:
1226:
1222:
1210:
1206:
1202:
1198:
1188:
1186:
1182:
1178:
1173:
1171:
1167:
1163:
1159:
1140:
1136:
1132:
1128:
1116:
1109:
1104:
1087:
1081:
1077:
1073:
1069:
1068:
1064:
1061:(Recommended)
1060:
1056:
1055:
1051:
1048:(Permissible)
1047:
1043:
1042:
1038:
1037:
1032:
1028:
1026:
1023:
1022:
1018:
1015:
1009:
1008:
1001:
994:
987:
963:
960:
959:
955:
954:
900:
897:
893:
892:
882:
879:
875:
874:
871:
868:
865:
861:
860:
856:
851:
847:
844:
840:
839:
835:
833:
828:
823:
819:
811:
803:
797:
796:
792:
787:
779:
775:
774:
770:
762:
754:
748:
747:
743:
735:
730:
724:
723:
719:
714:
709:
708:Heat capacity
705:
704:
699:
696:
693:
690:
686:
685:
680:
676:
674:
671:
670:
662:
658:
654:
653:
649:
647:
644:
643:
639:
633:
629:
626:
625:
621:
619:
616:
615:
612:
608:
602:
600:
597:
596:
592:
589:
585:
584:
580:
577:
571:
570:
566:
562:
560:
559:Melting point
557:
556:
552:
550:
547:
546:
542:
540:
537:
536:
532:
529:
528:
521:
519:
516:
515:
500:
497:
493:
492:
487:
478:
477:
474:
467:
453:
443:
442:
439:
432:
424:
420:
419:DTXSID6026379
416:
415:
413:
403:
399:
398:
394:
390:
386:
381:
378:
376:
373:
372:
365:
361:
360:
358:
356:
353:
352:
345:
344:
342:
340:
337:
336:
329:
325:
324:
322:
316:
312:
311:
304:
300:
299:
297:
295:
292:
291:
287:
284:
280:
279:
272:
271:
269:
267:
262:
261:
257:
253:
250:
248:
246:ECHA InfoCard
243:
242:
235:
231:
230:
228:
226:
223:
222:
215:
211:
210:
208:
206:
203:
202:
195:
191:
190:
188:
186:
183:
182:
178:
175:
171:
170:
163:
159:
158:
156:
152:
147:
146:
139:
135:
134:
132:
129:
125:
124:
119:
111:
107:
99:
95:
90:
86:
81:
77:
72:
68:
63:
59:
54:
48:
44:
40:
33:
19:
18:Acetylene gas
8868:
8859:
8812:
8806:
8795:
8786:
8779:
8774:
8764:
8759:
8524:
8518:
8437:
8402:
8393:
8387:Livermoranes
8152:Polysulfanes
8075:Polyoxidanes
8043:
8008:
7999:
7500:
7492:
7487:
7478:
7080:Cycloalkynes
7075:Cycloalkenes
7070:Cycloalkanes
7047:Hydrocarbons
7020:
7008:
7000:
6995:
6986:
6586:Monohydrides
6440:
6423:Spectroscopy
6277:Astrobiology
6130:Formaldehyde
6022:Benzonitrile
5813:Acetaldehyde
5768:Methanethiol
5719:Acetonitrile
5624:Carbodiimide
5503:Formaldehyde
5498:Cyanoethynyl
5482:
5349:Iron cyanide
5344:Hydroperoxyl
5145:Nitric oxide
4937:Alkynylation
4917:Halogenation
4876:dihaloalkane
4838:Preparations
4615:
4560:
4539:
4499:. Retrieved
4485:
4473:. Retrieved
4446:27 September
4444:. Retrieved
4423:
4404:
4392:. Retrieved
4361:. Retrieved
4347:
4335:. Retrieved
4328:the original
4283:
4277:
4258:
4252:
4240:. Retrieved
4199:. Retrieved
4185:
4168:
4164:
4158:
4141:
4137:
4133:
4127:
4106:
4078:
4074:
4068:
4041:
4035:
3992:
3986:
3976:
3968:the original
3953:
3945:the original
3931:
3896:
3890:
3878:. Retrieved
3848:
3844:
3834:
3815:
3797:
3785:. Retrieved
3769:. ABC-CLIO.
3765:
3758:
3746:. Retrieved
3737:
3728:
3716:. Retrieved
3697:
3693:
3683:
3675:the original
3670:
3661:
3650:
3641:
3629:. Retrieved
3604:(10): 1725.
3601:
3596:
3583:
3571:. Retrieved
3554:
3550:
3540:
3515:
3511:
3505:
3478:
3472:
3461:, retrieved
3434:
3424:
3413:, retrieved
3378:
3368:
3341:
3337:
3305:
3293:. Retrieved
3284:
3275:
3246:
3229:
3225:
3220:
3201:
3195:
3186:
3174:. Retrieved
3165:
3161:
3151:
3124:
3118:
3110:
3106:
3093:
3086:
3074:. Retrieved
3070:
3061:
3043:
3026:
3022:
3015:
2998:
2994:
2987:
2958:
2921:
2915:
2896:
2888:
2887:, series 3,
2884:
2871:
2864:
2856:
2849:. Retrieved
2824:
2820:
2810:
2802:
2801:, series 3,
2798:
2785:
2778:
2766:. Retrieved
2756:
2749:
2741:
2737:
2721:
2705:
2700:
2681:
2652:
2625:
2619:
2607:. Retrieved
2579:
2557:27 September
2555:. Retrieved
2546:
2537:
2495:
2489:
2470:
2458:. Retrieved
2453:
2443:
2434:
2408:
2403:
2389:
2383:
2380:
2372:gas cylinder
2317:
2308:polyethylene
2297:
2282:
2265:
2194:deprotonated
2185:
2181:
2142:
2133:
2068:hydroquinone
2053:
2034:
2010:acetaldehyde
2007:
1974:vinyl ethers
1959:
1938:, a moon of
1929:
1902:acetaldehyde
1891:
1848:
1829:
1822:
1815:
1772:
1760:acetaldehyde
1753:
1744:acetaldehyde
1741:
1708:acrylic acid
1701:
1686:
1665:ethynylation
1662:
1659:
1608:
1578:oxyacetylene
1571:
1563:Applications
1550:
1528:triple point
1525:
1501:
1476:In terms of
1475:
1455:
1440:
1433:
1418:O → Ca(OH)
1400:
1391:
1346:
1321:hydrocarbons
1310:
1274:
1262:
1236:
1224:
1194:
1174:
1134:
1126:
1125:
1035:
1012:Autoignition
957:
869:
831:
809:
785:
760:
733:
712:
631:
567:at 1.27 atm
565:Triple point
339:RTECS number
214:ChEMBL116336
121:Identifiers
47:
7970:Bismuthanes
6397:Outer space
6307:Cosmic dust
6272:Abiogenesis
6184:Unconfirmed
6140:Heavy water
5980:Ethanethiol
5895:Cyanoallene
5885:Acetic acid
5855:Methylamine
5739:Diacetylene
5654:Formic acid
5644:Cyanomethyl
5302:Diazenylium
5292:CCP radical
5168:(molecular)
5152:(molecular)
5121:(molecular)
4501:30 November
4475:30 November
4394:30 November
4363:30 November
4337:30 November
4242:30 November
3787:21 November
3748:24 February
3718:26 December
3694:Radiocarbon
3667:"Acetylene"
3631:18 February
3573:9 September
3295:30 November
3281:"Acetylene"
3228:(listed as
3176:23 December
2851:29 December
2547:Air Liquide
2200:to form an
2128:25 atm
1874:fire hazard
1855:lighthouses
1801:in 2000 to
1614:Bell Canada
1581:gas welding
1541:sublimation
1511:point group
1464:project at
1339:catalysts.
1259:Preparation
1197:Edmund Davy
1185:triple bond
1177:unsaturated
1158:hydrocarbon
1014:temperature
864:Signal word
667:10 cm/mol
605:soluble in
574:Sublimation
530:Appearance
489:Properties
382:(dissolved)
252:100.000.743
194:CHEBI:27518
9291:Categories
7993:Moscovanes
7858:Phosphenes
7720:Phosphanes
7518:Pnictogen
7475:Flerovanes
6626:Dihydrides
6576:(Group 2)
6312:Cosmic ray
6254:Silylidyne
6217:Hemolithin
6192:Anthracene
6109:Deuterated
6090:Pyrimidine
5900:Ethanimine
5763:Ketenimine
5619:Butadiynyl
5443:Thioformyl
5297:Chloronium
4863:Alkylation
4059:0471936235
3496:3527306730
2891:: 640–644.
2805:: 805–808.
2494:Record of
2395:References
2336:exothermic
2136:acetylides
2124:80 °C
1962:vinylation
1932:gas giants
1863:automobile
1689:butynediol
1631:decomposes
1485:hybridizes
1303:+ CO + 5 H
1277:combustion
1263:Except in
1253:carbon arc
1156:. It is a
843:Pictograms
802:combustion
682:Structure
599:Solubility
576:conditions
518:Molar mass
364:OC7TV75O83
225:ChemSpider
149:3D model (
128:CAS Number
51:Acetylene
9297:Acetylene
8869:predicted
8813:predicted
8796:predicted
8525:predicted
8403:predicted
8062:Hydrogen
8009:predicted
7479:predicted
7451:Plumbanes
7415:Stannanes
7085:Annulenes
6987:predicted
6983:Nihonanes
6947:Thallanes
6912:Indiganes
6682:Group 13
6574:Alkaline
6244:Phosphine
6112:molecules
6045:fullerene
5945:Acetamide
5749:Formamide
5629:Cyanamide
5483:Acetylene
5458:Tricarbon
5369:Methylene
5354:Isoformyl
5259:Triatomic
5032:Molecules
4922:Hydration
4900:Reactions
3738:uslhs.org
3405:178601434
3287:. Linde.
2901:Acetylene
2827:(2): 83.
2599:930681942
2496:Acetylene
2460:24 August
2324:phosphine
2272:inorganic
2246:≡
2233:⟶
2220:≡
2202:acetylide
2198:superbase
2105:O → 2 C
1994:carbazole
1951:Reactions
1944:catalytic
1936:Enceladus
1870:headlamps
1781:produces
1756:hydration
1669:aldehydes
1656:Chemicals
1627:flashback
1618:soldering
1609:equipment
1539:(gas) by
1453:carbon.
1438:in 1862.
1225:acétylène
1201:potassium
1191:Discovery
1170:phosphine
1137:) is the
1127:Acetylene
1029:2.5–100%
834:labelling
753:formation
727:Std molar
650:Ethynium
543:Odorless
393:propylene
375:UN number
346:AO9600000
273:200-816-9
265:EC Number
102:Acetylene
9307:Fuel gas
8782:< 1)
8328:Tellanes
7947:Stibanes
7342:Germanes
6877:Gallanes
6684:hydrides
6231:Linear C
6212:Graphene
6124:Ammonium
5925:Acrolein
5788:Propynal
5773:Methanol
5744:Ethylene
5613:Ammonium
5388:Nitroxyl
5212:Sulfanyl
5156:Imidogen
5150:Nitrogen
5119:Hydrogen
5064:Argonium
5041:Diatomic
4845:Cracking
4523:Archived
4495:Archived
4469:Archived
4437:Archived
4412:Archived
4388:Archived
4357:Archived
4302:69535236
4233:Archived
4195:Archived
4019:17251967
3923:25416389
3875:29933435
3781:Archived
3742:Archived
3712:Archived
3622:Archived
3567:Archived
3532:24256089
3457:archived
3409:archived
3360:24228942
3313:Archived
3289:Archived
3170:Archived
3099:Archived
3051:Archived
2904:Archived
2877:Archived
2845:Archived
2791:Archived
2762:Archived
2744:: 62–63.
2730:Archived
2690:Archived
2603:Archived
2551:Archived
2531:(NIOSH).
2478:Archived
2352:hydrogen
2304:ethylene
2266:Various
2018:ethylene
1966:Alcohols
1921:O → CH
1728:polymers
1635:hydrogen
1622:manholes
1597:cyanogen
1329:ethylene
1317:cracking
1313:ethylene
1249:hydrogen
1245:cyanogen
1241:effluent
958:NFPA 704
825:Hazards
659:(χ)
389:ethylene
9302:Alkynes
8767:< 1)
8364:Polanes
8291:Selanes
8277:more...
8139:more...
7911:Arsanes
7844:more...
7653:more...
7308:Silynes
7279:Silenes
7265:more...
7141:Silanes
7065:alkynes
7060:alkenes
7055:alkanes
6693:Boranes
6377:Kerogen
6264:Related
6207:Glycine
6160:Propyne
6119:Ammonia
6017:Benzene
6012:Acetone
6004:or more
5975:Propene
5960:Ethanol
5850:Propyne
5669:Methane
5538:Ketenyl
5488:Ammonia
4742:Heptyne
4679:Pentyne
4633:Propyne
4605:Alkynes
4027:4427890
3997:Bibcode
3880:28 July
3866:7190893
3606:Bibcode
3463:3 March
3415:3 March
3168:: 232.
3076:21 July
2829:Bibcode
2768:16 July
2525:"#0008"
2503:of the
2499:in the
2374:with a
2364:acetone
2342:and/or
2340:benzene
2162:aqueous
2028:vs the
1970:phenols
1836:lithium
1716:glasses
1691:, with
1673:ketones
1585:cutting
1568:Welding
1553:acetone
1530:on the
1497:π bonds
1482:orbital
1472:Bonding
1451:reduced
1281:methane
1154:H−C≡C−H
1108:what is
1106: (
781:(Δ
729:entropy
628:Acidity
611:benzene
607:acetone
549:Density
315:PubChem
179:906677
138:74-86-2
7667:Azenes
7529:Azanes
6842:Alanes
6428:Tholin
6249:Pyrene
5694:Silane
5664:Ketene
5166:Oxygen
4858:alkene
4854:alkane
4805:Decyne
4788:Nonyne
4759:Octyne
4708:Hexyne
4650:Butyne
4616:Ethyne
4300:
4290:
4265:
4171:: 20.
4144:: 14.
4115:
4056:
4025:
4017:
3988:Nature
3921:
3911:
3873:
3863:
3822:
3773:
3530:
3493:
3449:
3403:
3393:
3358:
3263:
3230:ethyne
3208:
3139:
3113:: 220.
2975:
2936:
2712:
2669:
2597:
2587:
2427:
2385:Copper
2348:carbon
2332:garlic
2328:arsine
2134:Metal
2117:+ FeCO
2089:Fe(CO)
1978:Thiols
1940:Saturn
1895:enzyme
1867:mining
1861:, and
1809:, and
1791:iodine
1726:, and
1724:resins
1720:paints
1639:carbon
1537:vapour
1181:bonded
1162:alkyne
1135:ethyne
1103:verify
1100:
870:Danger
695:Linear
523:26.038
473:SMILES
303:C01548
205:ChEMBL
114:Ethyne
92:Names
43:ethene
39:ethane
6414:(PAH)
6002:atoms
5937:atoms
5877:atoms
5875:Eight
5805:atoms
5803:Seven
5711:atoms
5605:atoms
5475:atoms
5463:Water
5393:Ozone
5335:(HNC)
5329:(HCN)
4440:(PDF)
4433:(PDF)
4331:(PDF)
4324:(PDF)
4236:(PDF)
4229:(PDF)
4201:2 May
4023:S2CID
3851:(8).
3625:(PDF)
3593:(PDF)
3481:: 7.
3401:S2CID
2609:4 May
2196:by a
2126:, 20–
2101:+ 2 H
2093:+ 4 C
1547:Other
1414:+ 2 H
1385:+ 3 H
1367:+ 2 H
1291:+ 3 O
1265:China
1078:N.D.
1052:none
1036:NIOSH
663:−20.8
438:InChI
185:ChEBI
151:JSmol
5935:Nine
5603:Five
5513:HCCN
5473:Four
5433:SiNC
4503:2016
4477:2016
4448:2018
4396:2016
4365:2016
4339:2016
4298:OCLC
4288:ISBN
4263:ISBN
4244:2016
4203:2012
4134:endo
4113:ISBN
4054:ISBN
4015:PMID
3919:PMID
3909:ISBN
3882:2022
3871:PMID
3820:ISBN
3789:2015
3771:ISBN
3750:2017
3720:2013
3633:2009
3575:2019
3528:PMID
3491:ISBN
3465:2022
3447:ISBN
3417:2022
3391:ISBN
3356:PMID
3297:2013
3261:ISBN
3206:ISBN
3178:2013
3137:ISBN
3078:2023
2973:ISBN
2934:ISBN
2853:2021
2770:2021
2710:ISBN
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2611:2022
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2585:ISBN
2559:2018
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2425:ISBN
2360:gage
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2326:and
2287:BASF
2281:The
2270:and
2156:and
2113:(OH)
1992:and
1984:and
1968:and
1865:and
1773:The
1671:and
1650:Bali
1637:and
1583:and
1576:for
1447:coal
1373:2 CH
1287:3 CH
1247:and
1211:, (K
1168:and
1072:IDLH
950:P501
946:P405
942:P403
938:P381
934:P377
930:P340
926:P312
922:P304
918:P271
914:P261
910:P233
906:P210
902:P202
888:H336
884:H220
539:Odor
391:and
385:3138
380:1001
355:UNII
328:6326
294:KEGG
288:210
234:6086
9276:PsH
9255:CfH
9247:CfH
9239:BkH
9231:BkH
9223:CmH
9215:AmH
9207:AmH
9199:PuH
9191:PuH
9183:NpH
9175:NpH
9151:PaH
9133:ThH
9125:ThH
9117:AcH
9096:LuH
9088:LuH
9080:YbH
9072:TmH
9064:TmH
9056:ErH
9048:ErH
9040:HoH
9032:HoH
9024:DyH
9016:DyH
9008:TbH
9000:TbH
8992:GdH
8984:GdH
8976:EuH
8968:SmH
8960:SmH
8952:NdH
8944:NdH
8936:PrH
8928:PrH
8920:CeH
8912:CeH
8904:LaH
8896:LaH
8888:LaH
8861:CnH
8852:HgH
8835:HgH
8827:CdH
8819:ZnH
8808:RgH
8802:CuH
8788:DsH
8772:PtH
8757:PdH
8752:NiH
8744:IrH
8736:RhH
8728:CoH
8720:FeH
8712:FeH
8707:FeH
8699:CrH
8691:CrH
8686:CrH
8678:TaH
8673:TaH
8665:NbH
8660:NbH
8639:HfH
8631:HfH
8623:ZrH
8615:ZrH
8607:TiH
8599:TiH
8591:LuH
8583:LuH
8543:ScH
8520:HTs
8514:HAt
8504:HBr
8499:HCl
8457:HDO
8446:(?)
8443:O–O
8395:LvH
8371:PoH
8051:(?)
8001:McH
7977:BiH
7954:SbH
7919:AsH
7501:FlH
7493:FlH
7488:FlH
7458:PbH
7423:SnH
7350:GeH
7328:SiH
7149:SiH
7021:NhH
7001:NhH
6996:NhH
6954:TlH
6919:InH
6884:GaH
6849:AlH
6665:BaH
6657:SrH
6649:CaH
6641:MgH
6633:BeH
6613:BaH
6608:SrH
6603:CaH
6598:MgH
6593:BeH
6564:CsH
6559:RbH
6549:NaH
6544:LiH
6226:NCO
6126:ion
6033:, C
6000:Ten
5709:Six
5615:ion
4874:of
4865:of
4852:of
4559:at
4544:at
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4083:doi
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3993:445
3901:doi
3861:PMC
3853:doi
3702:doi
3614:doi
3559:doi
3520:doi
3516:114
3483:doi
3439:doi
3383:doi
3346:doi
3342:114
3253:doi
3166:117
3129:doi
3111:124
3031:doi
3003:doi
2965:doi
2926:doi
2837:doi
2659:doi
2417:doi
2366:or
2302:to
2285:of
2146:M−C
2024:by
1960:In
1925:CHO
1917:+ H
1443:oil
1422:+ C
1410:CaC
1377:→ C
1359:→ C
1319:of
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1295:→ C
1279:of
1059:REL
1046:PEL
832:GHS
813:298
764:298
737:298
640:25
480:C#C
407:EPA
318:CID
41:or
9293::
9167:UH
9159:UH
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9140:Th
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8840:Hg
8652:VH
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8575:YH
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8559:YH
8551:YH
8509:HI
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8452:HS
8430:HO
8422:HO
8417:HO
8348:Te
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8312:Se
8303:Se
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8031:NH
8023:HN
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7838:12
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7814:10
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7623:10
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7316:Si
7287:Si
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7223:16
7217:Si
7211:14
7205:Si
7199:12
7193:Si
7187:10
7181:Si
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7157:Si
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7102:CH
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6962:Tl
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6828:22
6824:18
6816:14
6812:10
6804:12
6792:10
6780:11
6756:10
6709:BH
6701:BH
6554:KH
6043:70
6035:60
6031:60
6029:(C
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4856:,
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4211:^
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805:(Δ
756:(Δ
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9217:3
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8978:2
8970:3
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8922:3
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8211:5
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8119:O
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8097:2
8095:O
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8091:H
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8084:2
8082:H
8047:5
8038:5
8025:3
8011:)
8007:(
8003:3
7979:3
7956:3
7933:4
7931:H
7929:2
7921:3
7896:4
7894:H
7892:4
7890:P
7884:3
7882:H
7880:3
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7872:2
7870:H
7868:2
7866:P
7836:H
7832:P
7824:H
7822:9
7820:P
7812:H
7810:8
7808:P
7802:9
7800:H
7798:7
7796:P
7790:8
7788:H
7786:6
7784:P
7778:7
7776:H
7774:5
7772:P
7766:6
7764:H
7762:4
7760:P
7754:5
7752:H
7750:3
7748:P
7742:4
7740:H
7738:2
7736:P
7730:3
7705:4
7703:H
7701:4
7699:N
7693:3
7691:H
7689:3
7687:N
7681:2
7679:H
7677:2
7675:N
7645:H
7641:N
7633:H
7631:9
7629:N
7621:H
7619:8
7617:N
7611:9
7609:H
7607:7
7605:N
7599:8
7597:H
7595:6
7593:N
7587:7
7585:H
7583:5
7581:N
7575:6
7573:H
7571:4
7569:N
7563:5
7561:H
7559:3
7557:N
7551:4
7549:H
7547:2
7545:N
7539:3
7503:4
7495:2
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7477:(
7460:4
7437:6
7435:H
7433:2
7425:4
7398:H
7396:5
7386:H
7384:4
7376:8
7374:H
7372:3
7364:6
7362:H
7360:2
7352:4
7322:2
7320:H
7318:2
7293:4
7291:H
7289:2
7257:H
7245:H
7243:9
7233:H
7231:8
7221:H
7219:7
7209:H
7207:6
7197:H
7195:5
7185:H
7183:4
7175:8
7173:H
7171:3
7163:6
7161:H
7159:2
7151:4
7127:H
7125:2
7123:C
7117:3
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7023:5
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6933:6
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6921:3
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6861:H
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6826:H
6822:B
6814:H
6810:B
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6728:2
6726:B
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