1147:
1315:
652:
1124:
1159:
20:
915:
1063:
1267:
1171:
166:
186:
1252:
1086:. This compound was discontinued because the cation biodegrades too slowly. Contemporary fabric softeners are based on salts of quaternary ammonium cations where the fatty acid is linked to the quaternary center via ester linkages; these are commonly referred to as
1216:, the primary plant hormones responsible for cell elongation. Therefore, their effects are primarily on stem, petiole, and flower stalk tissues. Lesser effects are seen in reductions of leaf expansion, resulting in thicker leaves with darker green color.
1366:
Quaternary ammonium-based disinfectants (Virex and
Quatricide) were tentatively identified as the most probable cause of jumps in birth defects and fertility problems in caged lab mice. The quat ingredients in the disinfectants include
1502:
Kern A, Näther C, Studt F, Tuczek F (August 2004). "Application of a universal force field to mixed Fe/Mo-S/Se cubane and heterocubane clusters. 1. Substitution of sulfur by selenium in the series 2-; X = S/Se and Y = S/Se".
542:
2795:
Warshaw EM, Ahmed RL, Belsito DV, DeLeo VA, Fowler JF, Maibach HI, et al. (August 2007). "Contact dermatitis of the hands: cross-sectional analyses of North
American Contact Dermatitis Group Data, 1994-2004".
1375:(DDAC). A similar link was tentatively identified in nurses. The studies contradict earlier toxicology data reviewed by the U.S. Environmental Protection Agency (U.S. EPA) and the EU Commission.
2153:
Tischer, Maximilian; Pradel, Gabriele; Ohlsen, Knut; Holzgrabe, Ulrike (2 January 2012). "Quaternary
Ammonium Salts and Their Antimicrobial Potential: Targets or Nonspecific Interactions?".
1146:
1123:
1015:, both having no accessible membrane coat to attack. It is possible to solve the endospore problem by adding chemicals which force them to germinate. They have reduced efficacy against
2115:
Cocco AR, Rosa WL, Silva AF, Lund RG, Piva E (November 2015). "A systematic review about antibacterial monomers used in dental adhesive systems: Current status and further prospects".
640:, as well as dealkylation under harsh conditions or in presence of strong nucleophiles, like thiolates. Quaternary ammonium cations containing N−C−C−H units can also undergo the
2997:
Zhang C, Cui F, Zeng GM, Jiang M, Yang ZZ, Yu ZG, et al. (June 2015). "Quaternary ammonium compounds (QACs): a review on occurrence, fate and toxicity in the environment".
880:
also contain quaternary ammonium salts. Quats are also used in contraception formulations, veterinary products, diagnostic testing, vaccine production, and nasal formulations.
2463:
1327:
Quaternary ammonium compounds can display a range of health effects, amongst which are mild skin and respiratory irritation up to severe caustic burns on skin and the
2512:
Anthoni, U.; Christophersen, C.; Hougaard, L.; Nielsen, P.H. (1991). "Quaternary ammonium compounds in the biosphere—An
Example of a Versatile Adaptive Strategy".
2198:"A Quaternary Ammonium Disinfectant Containing Germinants Reduces Clostridium difficile Spores on Surfaces by Inducing Susceptibility to Environmental Stressors"
2978:
Office of
Prevention, Pesticides and Toxic Substances, US EPA (August 2006). "Reregistration Eligibility Decision for Aliphatic Alkyl Quaternaries (DDAC)".
883:
Concerns have been raised about the level of understanding of safety profile of quat disinfectants on people. As of August 2020, half of disinfectants the
2728:
2397:
1972:
1632:
1436:
933:
Quaternary ammonium compounds have antimicrobial activity. Quaternary ammonium compounds, especially those containing long alkyl chains, are used as
902:
exposed to quats have developed cross resistance to antibiotics. A subject of concern is the potential effect of increased use of quats related to
255:
1158:
1665:
Marino MG, Kreuer KD (February 2015). "Alkaline stability of quaternary ammonium cations for alkaline fuel cell membranes and ionic liquids".
884:
1027:
due to them having additional layers that need to be penetrated or disrupted. Some bacteria such as MRSA have acquired resistance genes,
2041:
1915:"Increased Use of Quaternary Ammonium Compounds during the SARS-CoV-2 Pandemic and Beyond: Consideration of Environmental Implications"
2679:"Characterization of occupational exposures to cleaning products used for common cleaning tasks--a pilot study of hospital cleaners"
2485:
2068:"Are Quaternary Ammonium Compounds, the Workhorse Disinfectants, Effective against Severe Acute Respiratory Syndrome-Coronavirus-2?"
3059:
2471:
1331:(depending on concentration), gastrointestinal symptoms (e.g., nausea and vomiting), coma, convulsions, hypotension and death.
2433:
588:
1047:(PTCs). Such catalysts accelerate reactions between reagents dissolved in immiscible solvents. The highly reactive reagent
1888:
2370:
2414:
2319:
1823:
1649:
1129:
1079:
587:
Because of their resilience, many unusual anions have been isolated as the quaternary ammonium salts. Examples include
2661:
1856:
1614:
633:
2005:
Jia Z, shen D, Xu W (June 2001). "Synthesis and antibacterial activities of quaternary ammonium salt of chitosan".
1413:
1372:
1170:
970:
1314:
1181:
The antistatic qualities that make quaternary ammonium salts useful as fabric softeners also make them useful in
677:
of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.
2247:"Different virucidal activities of hyperbranched quaternary ammonium coatings on poliovirus and influenza virus"
1989:
1558:
2541:"Diversity, distribution and roles of osmoprotective compounds accumulated in halophytes under abiotic stress"
1387:
of quaternary ammonium compounds can be challenging. Some methods include precipitation of solid salts with
573:
577:
237:. The reaction can be used to produce a compound with unequal alkyl chain lengths; for example when making
1339:
1467:
966:
241:
one of the alkyl groups on the amine is typically longer than the others. A typical synthesis is for
1384:
954:
896:
1550:
1198:
1044:
873:
2929:
Gaskins AJ, Chavarro JE, Rich-Edwards JW, Missmer SA, Laden F, Henn SA, Lawson CC (March 2017).
3064:
2653:
2647:
1016:
906:
on antibiotic resistance in a larger microbial community in nature and engineered environment.
2977:
1368:
1335:
1328:
946:
942:
655:
637:
242:
178:
3038:
2045:
238:
3069:
3002:
2885:
2258:
1752:
1717:
1674:
1290:
1194:
950:
670:
8:
2489:
1343:
1294:
1012:
751:
687:
641:
230:
92:
3006:
2889:
2872:
Melin VE, Potineni H, Hunt P, Griswold J, Siems B, Werre SR, Hrubec TC (December 2014).
2539:
Slama, Inès; Abdelly, Chedly; Bouchereau, Alain; Flowers, Tim; Savouré, Arnould (2015).
2429:
2262:
1872:
1756:
1721:
1678:
2955:
2930:
2906:
2873:
2772:
2747:
2705:
2678:
2642:
2617:
2592:
2565:
2540:
2352:
2279:
2246:
2222:
2197:
2178:
2092:
2067:
1947:
1914:
1355:
1107:
789:
717:
2018:
1224:
Several quaternary ammonium derivatives exist in nature. Prominent examples include
651:
3018:
2960:
2911:
2854:
2813:
2777:
2763:
2710:
2657:
2622:
2608:
2570:
2525:
2410:
2356:
2315:
2284:
2227:
2170:
2132:
2097:
2022:
1985:
1952:
1934:
1852:
1819:
1784:
1690:
1645:
1610:
1554:
1520:
1475:
1388:
903:
218:, which can generate primary or secondary amines. These amines are then treated with
36:
3014:
2833:"Lab disinfectant harms mouse fertility. Patricia Hunt interviewed by Brendan Maher"
2746:
Harper NJ, Dixon T, Dugué P, Edgar DM, Fay A, Gooi HC, et al. (February 2009).
2182:
1708:
Herriott AW (1977). "Purple benzene: Solubilization of anions in organic solvents".
1446:
3010:
2950:
2942:
2901:
2897:
2893:
2844:
2805:
2767:
2759:
2700:
2690:
2612:
2604:
2560:
2552:
2521:
2402:
2344:
2307:
2274:
2266:
2217:
2209:
2162:
2124:
2087:
2079:
2014:
1977:
1942:
1926:
1844:
1811:
1760:
1725:
1682:
1637:
1583:
1546:
1512:
1450:
1441:
1182:
1137:
1056:
926:
846:
645:
608:
214:. Industrial production of commodity quat salts usually involves hydrogenation of
147:
116:
2874:"Exposure to common quaternary ammonium disinfectants decreases fertility in mice"
2311:
1069:
resins, in the form of beads, contain quaternary ammonium ions bound to a polymer.
2128:
1806:
Pine SH (2011). "The Base-Promoted
Rearrangements of Quaternary Ammonium Salts".
1541:
Weston, Charles W.; Papcun, John R.; Dery, Maurice (2003). "Ammonium
Compounds".
1255:
1225:
1133:
1083:
1048:
865:
842:
246:
219:
143:
2083:
1930:
1815:
1779:
2809:
1308:
1259:
1066:
1007:
Quaternary ammonium compounds are lethal to a wide variety of organisms except
997:
982:
211:
151:
131:
120:
48:
2445:
2348:
2335:
Hellberg PE, Bergström K, Holmberg K (January 2000). "Cleavable surfactants".
1258:
is a naturally occurring quaternary ammonium cation. Its degradation product,
3053:
2588:
2406:
1981:
1938:
1848:
1641:
1587:
1479:
1445:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1351:
1278:
993:
934:
922:
862:
215:
19:
2245:
Tuladhar, E; de Koning, MC; Fundeanu, I; Beumer, R; Duizer, E (April 2012).
1454:
1212:(chlormequat chloride) reduces plant height by inhibiting the production of
992:), most quaternary ammonium compounds are believed to act by disrupting the
914:
537:{\displaystyle {\ce {CH3(CH2)_{\mathit {n}}N(CH3)2{}+ClCH2C6H5->{}+Cl-}}}
3022:
2964:
2915:
2858:
2817:
2781:
2714:
2695:
2626:
2574:
2288:
2231:
2174:
2166:
2136:
2101:
2026:
1956:
1694:
1686:
1524:
1286:
1241:
1062:
1020:
938:
834:
783:
711:
604:
553:
139:
2213:
1391:. Another method, an Epton titration, involves partitioning between water-
2931:"Occupational use of high-level disinfectants and fecundity among nurses"
2556:
2270:
1602:
1395:
in the presence of an anionic dye. Individual cations are detectable by
1213:
1209:
1103:
1001:
958:
838:
821:
745:
565:
2514:
Comparative
Biochemistry and Physiology Part B: Comparative Biochemistry
1764:
1729:
2946:
2395:
Smulders E, Sung E. "Laundry
Detergents, 2. Ingredients and Products".
1392:
1099:
1091:
1052:
1008:
877:
666:
226:
207:
155:
1516:
1361:
127:
forms which provide multiple quat molecules within a larger molecule.
23:
Quaternary ammonium cation. The R groups may be the same or different
1304:
1285:, which is present in many plants and animal organs. It is found in
1233:
962:
891:
contained one of the quats, and often a quat as the sole ingredient.
569:
135:
2849:
2832:
2511:
2374:
1090:-esters or ester-quats and are susceptible to degradation, e.g., by
1004:
and similar bis-QACs, show evidence of a different mode of action.)
632:
With exceptionally strong bases, quat cations degrade. They undergo
1408:
1298:
1282:
1266:
1245:
1237:
1164:
Diethyl ester dimethyl ammonium chloride used as a fabric softener.
989:
918:
888:
858:
663:
611:
112:
72:
3043:
Internationally Peer
Reviewed Chemical Safety Information (INCHEM)
2928:
2733:
Internationally Peer Reviewed Chemical Safety Information (INCHEM)
1418:
1347:
1270:
1229:
1186:
1087:
1024:
985:
978:
869:
850:
674:
659:
557:
229:
is widely documented. In older literature this is often called a
124:
88:
68:
2302:
De Dardel, François; Arden, Thomas V. (2008). "Ion Exchangers".
1607:
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
1043:
In organic chemistry, quaternary ammonium salts are employed as
2244:
1396:
1190:
1111:
854:
159:
2748:"Suspected anaphylactic reactions associated with anaesthesia"
1839:
Lackner M, Guggenbichler JP (2013). "Antimicrobial Surfaces".
552:
Quaternary ammonium cations are unreactive toward even strong
185:
165:
2538:
1095:
974:
617:
95:
ammonium cations are permanently charged, independent of the
60:
24:
2152:
1102:
ammonium salt. Other cationic compounds can be derived from
1889:"Do we know enough about the safety of quat disinfectants?"
561:
64:
28:
2446:"Quaternary ammonium compound hair conditioners US4744977"
1743:
Doheny Jr AJ, Ganem B (1980). "Purple benzene revisited".
1334:
They are thought to be the chemical group responsible for
1251:
1094:. Characteristically, the cations contain one or two long
2871:
2334:
1073:
510:
497:
484:
471:
458:
437:
422:
404:
381:
368:
355:
337:
324:
303:
288:
270:
2794:
925:(anti-spasm drugs) that feature the quaternary ammonium
233:, however modern chemists usually refer to it simply as
1913:
Hora PI, Pati SG, McNamara PJ, Arnold WA (2020-09-08).
1574:
Brasen WR, Hauser CR (1954). "o-Methylbenzyl Alcohol".
1301:
group of fatty substances in animal and plant tissues.
96:
2935:
Scandinavian Journal of Work, Environment & Health
2639:
1912:
2745:
2677:
Bello A, Quinn MM, Perry MJ, Milton DK (March 2009).
2676:
1501:
1468:"The Best Surface Cleaners, Wipes, and Disinfectants"
258:
162:-based disinfectants, and are generally fabric-safe.
130:
Quats are used in consumer applications including as
2065:
1838:
1152:
Another diesterquat, a contemporary fabric softener.
591:, containing the highly reactive pentafluoroxenate (
2502:
Wageningen Agricultural University, The Netherlands
1362:
Possible reproductive effects in laboratory animals
150:. As an antimicrobial, they are able to inactivate
87:) and the primary, secondary, or tertiary ammonium
2649:Biochemistry of Lipids, Lipoproteins and Membranes
2641:
2593:"Choline: an essential nutrient for public health"
2114:
1887:
1609:(5th ed.). New York, NY: Wiley-Interscience.
568:. The latter is indicated by the stability of the
536:
206:Quaternary ammonium compounds are prepared by the
2996:
1969:
1354:is the single most often found cause of allergic
580:even at elevated temperatures. The halflife of Me
3051:
2195:
1970:Bungardt E, Mutschler E (2000). "Spasmolytics".
1540:
1277:Choline is a precursor for the neurotransmitter
2066:Schrank CL, Minbiole KP, Wuest WM (July 2020).
1543:Kirk-Othmer Encyclopedia of Chemical Technology
2798:Journal of the American Academy of Dermatology
2587:
2398:Ullmann's Encyclopedia of Industrial Chemistry
2304:Ullmann's Encyclopedia of Industrial Chemistry
2301:
1973:Ullmann's Encyclopedia of Industrial Chemistry
1919:Environmental Science & Technology Letters
1841:Ullmann's Encyclopedia of Industrial Chemistry
1742:
1633:Ullmann's Encyclopedia of Industrial Chemistry
1262:, is responsible for the odor of spoiled fish.
1176:Another diesterquat used as a fabric softener.
16:Polyatomic ions of the form N(–R)₄ (charge +1)
1118:Cationic surfactants used as fabric softeners
1098:chains derived from fatty acids linked to an
885:United States Environmental Protection Agency
158:). Quats tend to be gentler on surfaces than
2643:"Chapter 2: Lipid metabolism in procaryotes"
2033:
1777:
1664:
1573:
1551:10.1002/0471238961.0113131523051920.a01.pub2
31:groups. Also, the R groups may be connected.
2640:Jackowski S, Cronan Jr JE, Rock CO (1991).
2196:Nerandzic, MM; Donskey, CJ (October 2016).
1038:
2148:
2146:
1600:
1204:
2954:
2905:
2848:
2771:
2704:
2694:
2616:
2564:
2278:
2221:
2091:
2004:
1946:
1465:
1110:, substituted amine salts, or quaternary
245:from a long-chain alkyldimethylamine and
2394:
2373:. Henkelconsumerinfo.com. Archived from
1707:
1318:1-Oleoyl-2-palmitoyl-phosphatidylcholine
1313:
1265:
1250:
1248:, stabilizes osmotic pressure in cells.
1061:
1035:, that pump the cation out of the cell.
973:and domiphen bromide. Also good against
913:
658:is a common type of quat salt used as a
650:
184:
164:
18:
2388:
2143:
2044:. Ohio State University. Archived from
1369:alkyl dimethyl benzyl ammonium chloride
197:as determined by X-ray crystallography.
3052:
2735:. World Health Organization. PIM G022.
2581:
2251:Applied and Environmental Microbiology
1497:
1495:
1074:Fabric softeners and hair conditioners
872:salts are often used. Older aluminium
833:Quaternary ammonium salts are used as
584:NOH in 6M NaOH at 160 °C is >61 h.
225:The quaternization of alkyl amines by
2434:Consumer Product Information Database
2337:Journal of Surfactants and Detergents
1219:
1193:with a 1984 patent. Examples include
589:tetramethylammonium pentafluoroxenate
431:
297:
2999:The Science of the Total Environment
2830:
2824:
1805:
1536:
1534:
1051:is generated via PTC by reaction of
3039:"Toxicities of quaternary ammonium"
1885:
1629:
1492:
1358:of the hands (16.5% in 959 cases).
1281:. Choline is also a constituent of
564:. They also are stable toward most
13:
2989:
2039:
1442:Compendium of Chemical Terminology
1373:didecyl dimethyl ammonium chloride
1130:Distearyldimethylammonium chloride
1080:distearyldimethylammonium chloride
14:
3081:
3031:
1567:
1531:
1378:
1322:
2764:10.1111/j.1365-2044.2008.05733.x
2609:10.1111/j.1753-4887.2009.00246.x
1414:Benzyltrimethylammonium fluoride
1169:
1157:
1145:
1122:
971:didecyldimethylammonium chloride
119:of quaternary ammonium cations.
3015:10.1016/j.scitotenv.2015.03.007
2971:
2922:
2865:
2788:
2739:
2721:
2670:
2646:. In Vance DE, Vance J (eds.).
2633:
2591:, da Costa KA (November 2009).
2532:
2505:
2478:
2470:. November 2007. Archived from
2464:"What is cetrimonium chloride?"
2456:
2438:
2423:
2363:
2328:
2295:
2238:
2189:
2108:
2059:
1998:
1963:
1906:
1879:
1865:
1832:
1799:
1771:
1736:
1082:(DHTDMAC), was introduced as a
949:, methylbenzethonium chloride,
887:suggested as effective against
828:
2898:10.1016/j.reprotox.2014.07.071
2202:Open Forum Infectious Diseases
1701:
1658:
1623:
1594:
1459:
1430:
513:
461:
445:
425:
409:
391:
384:
327:
311:
291:
275:
1:
3060:Quaternary ammonium compounds
2312:10.1002/14356007.a14_393.pub2
2019:10.1016/S0008-6215(01)00112-4
1894:Chemical and Engineering News
1780:"2-Methylbenzyldimethylamine"
1778:Brasen WR, Hauser CR (1963).
1745:Journal of Chemical Education
1710:Journal of Chemical Education
1466:Heffernan T (14 April 2021).
1447:quaternary ammonium compounds
1424:
634:Sommelet–Hauser rearrangement
574:tetramethylammonium hydroxide
105:quaternary ammonium compounds
3045:. World Health Organization.
2526:10.1016/0305-0491(91)90002-U
2129:10.1016/j.dental.2015.08.155
1340:neuromuscular blocking drugs
1189:. The idea was pioneered by
909:
578:tetrabutylammonium hydroxide
547:
201:
123:are a variety of engineered
7:
2084:10.1021/acs.estlett.0c00437
1931:10.1021/acs.estlett.0c00437
1816:10.1002/0471264180.or018.04
1402:
681:
41:quaternary ammonium cations
10:
3086:
2810:10.1016/j.jaad.2007.04.016
2430:Distearyldimonium chloride
1794:, vol. 4, p. 585
1630:Kosswig K. "Surfactants".
967:tetraethylammonium bromide
2349:10.1007/s11743-000-0118-z
2042:"Specific Antimicrobials"
1886:Lim XZ (August 2, 2020).
861:salts are often used. In
101:Quaternary ammonium salts
47:, are positively-charged
2407:10.1002/14356007.o15_013
1982:10.1002/14356007.a24_515
1849:10.1002/14356007.q03_q01
1642:10.1002/14356007.a25_747
1588:10.15227/orgsyn.034.0058
1045:phase transfer catalysts
1039:Phase transfer catalysts
955:cetylpyridinium chloride
2878:Reproductive Toxicology
2401:. Weinheim: Wiley-VCH.
2072:ACS Infectious Diseases
1976:. Weinheim: Wiley-VCH.
1636:. Weinheim: Wiley-VCH.
1455:10.1351/goldbook.Q05003
1338:that occur with use of
1293:, a major component of
1205:Plant growth retardants
1199:behentrimonium chloride
874:electrolytic capacitors
614:, when deployed as its
2696:10.1186/1476-069X-8-11
2371:"Henkel Consumer Info"
2167:10.1002/cmdc.201100404
1687:10.1002/cssc.201403022
1399:and NMR spectroscopy.
1336:anaphylactic reactions
1319:
1297:, are a member of the
1274:
1263:
1244:. Glycine betaine, an
1132:, an early generation
1070:
1017:gram-negative bacteria
1000:. (Some QACs, such as
930:
857:fabric softeners, the
678:
607:can be solubilized in
538:
198:
182:
32:
2729:"Quaternary ammonium"
2652:. Elsevier. pp.
2492:on September 25, 2011
2007:Carbohydrate Research
1329:gastrointestinal wall
1317:
1269:
1254:
1065:
1013:non-enveloped viruses
965:, dofanium chloride,
947:benzethonium chloride
943:benzalkonium chloride
917:
656:Benzalkonium chloride
654:
638:Stevens rearrangement
539:
243:benzalkonium chloride
188:
179:X-ray crystallography
168:
22:
3001:. 518–519: 352–362.
2831:Hunt P (June 2008).
2683:Environmental Health
2271:10.1128/AEM.07738-11
1873:"Quats applications"
1810:. pp. 403–464.
1307:participates in the
1295:biological membranes
1291:phosphatidylcholines
1195:cetrimonium chloride
1140:that was phased out.
951:cetalkonium chloride
671:phase transfer agent
256:
239:cationic surfactants
3007:2015ScTEn.518..352Z
2890:2014RepTx..50..163M
2486:"Growth Retardants"
2452:. 14 November 1985.
2263:2012ApEnM..78.2456T
2214:10.1093/ofid/ofw196
1765:10.1021/ed057p308.1
1757:1980JChEd..57..308D
1730:10.1021/ed054p229.1
1722:1977JChEd..54Q.229H
1679:2015ChSCh...8..513M
1505:Inorganic Chemistry
1344:general anaesthesia
1273:is a quat compound.
878:spermicidal jellies
752:Tetrapropylammonium
688:Tetramethylammonium
642:Hofmann elimination
512:
499:
486:
473:
460:
439:
424:
406:
383:
370:
357:
339:
326:
305:
290:
272:
231:Menshutkin reaction
99:of their solution.
2947:10.5271/sjweh.3623
2557:10.1093/aob/mcu239
2468:naturallycurly.com
1875:. 22 October 2021.
1472:The New York Times
1356:contact dermatitis
1320:
1275:
1264:
1220:Natural occurrence
1071:
1023:, and bacteria in
931:
923:spasmolytics
790:Tetrabutylammonium
718:Tetraethylammonium
679:
534:
500:
487:
474:
448:
443:
412:
407:
394:
371:
358:
345:
314:
309:
278:
273:
260:
199:
183:
71:group. Unlike the
33:
2597:Nutrition Reviews
2123:(11): 1345–1362.
1843:. pp. 1–13.
1808:Organic Reactions
1792:Collected Volumes
1785:Organic Syntheses
1576:Organic Syntheses
1517:10.1021/ic030347d
1511:(16): 5003–5010.
1389:tetraphenylborate
1236:. butyrobetaine,
1183:hair conditioners
904:COVID-19 pandemic
847:antistatic agents
526:
503:
490:
477:
451:
442:
433:
415:
397:
374:
361:
348:
317:
308:
299:
281:
263:
177:as determined by
152:enveloped viruses
148:hair conditioners
109:quaternary amines
51:of the structure
37:organic chemistry
3077:
3046:
3026:
2984:
2983:
2975:
2969:
2968:
2958:
2926:
2920:
2919:
2909:
2869:
2863:
2862:
2852:
2828:
2822:
2821:
2792:
2786:
2785:
2775:
2743:
2737:
2736:
2725:
2719:
2718:
2708:
2698:
2674:
2668:
2667:
2645:
2637:
2631:
2630:
2620:
2585:
2579:
2578:
2568:
2545:Annals of Botany
2536:
2530:
2529:
2509:
2503:
2501:
2499:
2497:
2488:. Archived from
2482:
2476:
2475:
2460:
2454:
2453:
2442:
2436:
2427:
2421:
2420:
2392:
2386:
2385:
2383:
2382:
2367:
2361:
2360:
2332:
2326:
2325:
2299:
2293:
2292:
2282:
2242:
2236:
2235:
2225:
2193:
2187:
2186:
2150:
2141:
2140:
2117:Dental Materials
2112:
2106:
2105:
2095:
2078:(7): 1553–1557.
2063:
2057:
2056:
2054:
2053:
2037:
2031:
2030:
2002:
1996:
1995:
1967:
1961:
1960:
1950:
1910:
1904:
1903:
1901:
1900:
1891:
1883:
1877:
1876:
1869:
1863:
1862:
1836:
1830:
1829:
1803:
1797:
1795:
1788:
1775:
1769:
1768:
1740:
1734:
1733:
1705:
1699:
1698:
1662:
1656:
1655:
1627:
1621:
1620:
1598:
1592:
1591:
1571:
1565:
1564:
1538:
1529:
1528:
1499:
1490:
1489:
1487:
1486:
1463:
1457:
1434:
1311:of fatty acids.
1173:
1161:
1149:
1138:biodegradability
1126:
1114:ammonium salts.
1057:sodium hydroxide
927:functional group
843:fabric softeners
819:
811:
781:
773:
743:
735:
709:
701:
673:. ADBACs are a
646:Emde degradation
628:
627:
626:
602:
601:
600:
543:
541:
540:
535:
533:
532:
531:
524:
522:
521:
516:
511:
508:
501:
498:
495:
488:
485:
482:
475:
472:
469:
464:
459:
456:
449:
440:
438:
435:
434:
428:
423:
420:
413:
405:
402:
395:
388:
382:
379:
372:
369:
366:
359:
356:
353:
346:
341:
338:
335:
330:
325:
322:
315:
306:
304:
301:
300:
294:
289:
286:
279:
271:
268:
261:
196:
176:
144:fabric softeners
86:
85:
84:
81:
59:, where R is an
58:
43:, also known as
3085:
3084:
3080:
3079:
3078:
3076:
3075:
3074:
3050:
3049:
3037:
3034:
3029:
2992:
2990:Further reading
2987:
2980:Epa739-R-06-008
2976:
2972:
2927:
2923:
2870:
2866:
2850:10.1038/453964a
2829:
2825:
2793:
2789:
2744:
2740:
2727:
2726:
2722:
2675:
2671:
2664:
2638:
2634:
2603:(11): 615–623.
2586:
2582:
2537:
2533:
2510:
2506:
2495:
2493:
2484:
2483:
2479:
2462:
2461:
2457:
2444:
2443:
2439:
2428:
2424:
2417:
2393:
2389:
2380:
2378:
2369:
2368:
2364:
2333:
2329:
2322:
2300:
2296:
2243:
2239:
2194:
2190:
2151:
2144:
2113:
2109:
2064:
2060:
2051:
2049:
2038:
2034:
2003:
1999:
1992:
1968:
1964:
1911:
1907:
1898:
1896:
1884:
1880:
1871:
1870:
1866:
1859:
1837:
1833:
1826:
1804:
1800:
1790:
1776:
1772:
1741:
1737:
1706:
1702:
1663:
1659:
1652:
1628:
1624:
1617:
1599:
1595:
1572:
1568:
1561:
1539:
1532:
1500:
1493:
1484:
1482:
1464:
1460:
1435:
1431:
1427:
1405:
1381:
1364:
1325:
1289:. For example,
1256:Glycine betaine
1226:glycine betaine
1222:
1207:
1177:
1174:
1165:
1162:
1153:
1150:
1141:
1134:fabric softener
1127:
1084:fabric softener
1076:
1049:dichlorocarbene
1041:
941:. Examples are
921:is one of many
912:
831:
817:
813:
812:, also denoted
809:
805:
801:
793:
779:
775:
774:, also denoted
771:
767:
763:
755:
741:
737:
736:, also denoted
733:
729:
725:
721:
707:
703:
702:, also denoted
699:
695:
691:
684:
625:
622:
621:
620:
615:
599:
596:
595:
594:
592:
583:
550:
527:
523:
517:
509:
504:
496:
491:
483:
478:
470:
465:
457:
452:
444:
436:
430:
429:
421:
416:
408:
403:
398:
390:
389:
387:
380:
375:
367:
362:
354:
349:
340:
336:
331:
323:
318:
310:
302:
296:
295:
287:
282:
274:
269:
264:
259:
257:
254:
253:
247:benzyl chloride
220:methyl chloride
204:
194:
190:
189:"Side" view of
174:
170:
82:
79:
78:
76:
56:
52:
49:polyatomic ions
17:
12:
11:
5:
3083:
3073:
3072:
3067:
3062:
3048:
3047:
3033:
3032:External links
3030:
3028:
3027:
2993:
2991:
2988:
2986:
2985:
2970:
2941:(2): 171–180.
2921:
2864:
2823:
2804:(2): 301–314.
2787:
2758:(2): 199–211.
2738:
2720:
2669:
2662:
2632:
2580:
2551:(3): 433–447.
2531:
2504:
2477:
2474:on 2012-03-04.
2455:
2450:Google Patents
2437:
2422:
2416:978-3527306732
2415:
2387:
2362:
2327:
2321:978-3527306732
2320:
2294:
2237:
2188:
2142:
2107:
2058:
2032:
1997:
1990:
1962:
1925:(9): 622–631.
1905:
1878:
1864:
1857:
1831:
1825:978-0471264187
1824:
1798:
1770:
1735:
1700:
1673:(3): 513–523.
1657:
1651:978-3527306732
1650:
1622:
1615:
1593:
1566:
1559:
1530:
1491:
1458:
1428:
1426:
1423:
1422:
1421:
1416:
1411:
1404:
1401:
1385:quantification
1380:
1379:Quantification
1377:
1363:
1360:
1324:
1323:Health effects
1321:
1309:beta-oxidation
1260:trimethylamine
1221:
1218:
1206:
1203:
1179:
1178:
1175:
1168:
1166:
1163:
1156:
1154:
1151:
1144:
1142:
1128:
1121:
1119:
1078:In the 1950s,
1075:
1072:
1067:Anion exchange
1040:
1037:
998:viral envelope
935:antimicrobials
911:
908:
830:
827:
826:
825:
815:
807:
803:
799:
787:
777:
769:
765:
761:
749:
739:
731:
727:
723:
715:
705:
697:
693:
683:
680:
623:
597:
581:
572:salts such as
549:
546:
545:
544:
530:
520:
515:
507:
494:
481:
468:
463:
455:
447:
427:
419:
411:
401:
393:
386:
378:
365:
352:
344:
334:
329:
321:
313:
293:
285:
277:
267:
235:quaternization
216:fatty nitriles
212:tertiary amine
203:
200:
192:
172:
169:"Top" view of
132:antimicrobials
115:parlance) are
54:
15:
9:
6:
4:
3:
2:
3082:
3071:
3068:
3066:
3065:Disinfectants
3063:
3061:
3058:
3057:
3055:
3044:
3040:
3036:
3035:
3024:
3020:
3016:
3012:
3008:
3004:
3000:
2995:
2994:
2981:
2974:
2966:
2962:
2957:
2952:
2948:
2944:
2940:
2936:
2932:
2925:
2917:
2913:
2908:
2903:
2899:
2895:
2891:
2887:
2883:
2879:
2875:
2868:
2860:
2856:
2851:
2846:
2843:(7198): 964.
2842:
2838:
2834:
2827:
2819:
2815:
2811:
2807:
2803:
2799:
2791:
2783:
2779:
2774:
2769:
2765:
2761:
2757:
2753:
2749:
2742:
2734:
2730:
2724:
2716:
2712:
2707:
2702:
2697:
2692:
2688:
2684:
2680:
2673:
2665:
2663:0-444-89321-0
2659:
2655:
2651:
2650:
2644:
2636:
2628:
2624:
2619:
2614:
2610:
2606:
2602:
2598:
2594:
2590:
2584:
2576:
2572:
2567:
2562:
2558:
2554:
2550:
2546:
2542:
2535:
2527:
2523:
2519:
2515:
2508:
2491:
2487:
2481:
2473:
2469:
2465:
2459:
2451:
2447:
2441:
2435:
2431:
2426:
2418:
2412:
2408:
2404:
2400:
2399:
2391:
2377:on 2019-10-18
2376:
2372:
2366:
2358:
2354:
2350:
2346:
2342:
2338:
2331:
2323:
2317:
2313:
2309:
2306:. p. 5.
2305:
2298:
2290:
2286:
2281:
2276:
2272:
2268:
2264:
2260:
2257:(7): 2456–8.
2256:
2252:
2248:
2241:
2233:
2229:
2224:
2219:
2215:
2211:
2208:(4): ofw196.
2207:
2203:
2199:
2192:
2184:
2180:
2176:
2172:
2168:
2164:
2160:
2156:
2149:
2147:
2138:
2134:
2130:
2126:
2122:
2118:
2111:
2103:
2099:
2094:
2089:
2085:
2081:
2077:
2073:
2069:
2062:
2048:on 2008-10-15
2047:
2043:
2036:
2028:
2024:
2020:
2016:
2012:
2008:
2001:
1993:
1987:
1983:
1979:
1975:
1974:
1966:
1958:
1954:
1949:
1944:
1940:
1936:
1932:
1928:
1924:
1920:
1916:
1909:
1895:
1890:
1882:
1874:
1868:
1860:
1858:9783527306732
1854:
1850:
1846:
1842:
1835:
1827:
1821:
1817:
1813:
1809:
1802:
1793:
1787:
1786:
1781:
1774:
1766:
1762:
1758:
1754:
1750:
1746:
1739:
1731:
1727:
1723:
1719:
1715:
1711:
1704:
1696:
1692:
1688:
1684:
1680:
1676:
1672:
1668:
1661:
1653:
1647:
1643:
1639:
1635:
1634:
1626:
1618:
1616:0-471-58589-0
1612:
1608:
1604:
1597:
1589:
1585:
1581:
1577:
1570:
1562:
1556:
1552:
1548:
1544:
1537:
1535:
1526:
1522:
1518:
1514:
1510:
1506:
1498:
1496:
1481:
1477:
1473:
1469:
1462:
1456:
1452:
1448:
1444:
1443:
1438:
1433:
1429:
1420:
1417:
1415:
1412:
1410:
1407:
1406:
1400:
1398:
1394:
1390:
1386:
1376:
1374:
1370:
1359:
1357:
1353:
1352:Quaternium-15
1349:
1345:
1341:
1337:
1332:
1330:
1316:
1312:
1310:
1306:
1302:
1300:
1296:
1292:
1288:
1287:phospholipids
1284:
1280:
1279:acetylcholine
1272:
1268:
1261:
1257:
1253:
1249:
1247:
1243:
1239:
1235:
1231:
1227:
1217:
1215:
1211:
1202:
1200:
1196:
1192:
1188:
1184:
1172:
1167:
1160:
1155:
1148:
1143:
1139:
1135:
1131:
1125:
1120:
1117:
1116:
1115:
1113:
1109:
1105:
1101:
1097:
1093:
1089:
1085:
1081:
1068:
1064:
1060:
1058:
1054:
1050:
1046:
1036:
1034:
1030:
1026:
1022:
1018:
1014:
1010:
1005:
1003:
999:
995:
994:cell membrane
991:
987:
984:
980:
976:
972:
968:
964:
960:
956:
952:
948:
944:
940:
939:disinfectants
936:
928:
924:
920:
916:
907:
905:
901:
899:
894:
890:
886:
881:
879:
875:
871:
867:
864:
860:
856:
852:
848:
844:
840:
836:
835:disinfectants
823:
797:
791:
788:
785:
759:
753:
750:
747:
719:
716:
713:
689:
686:
685:
676:
672:
668:
665:
661:
657:
653:
649:
647:
643:
639:
635:
630:
619:
613:
610:
606:
590:
585:
579:
575:
571:
567:
563:
559:
555:
554:electrophiles
528:
518:
505:
492:
479:
466:
453:
417:
399:
376:
363:
350:
342:
332:
319:
283:
265:
252:
251:
250:
248:
244:
240:
236:
232:
228:
227:alkyl halides
223:
221:
217:
213:
209:
187:
180:
167:
163:
161:
157:
153:
149:
145:
141:
140:disinfectants
137:
133:
128:
126:
122:
118:
114:
110:
106:
102:
98:
94:
90:
74:
70:
66:
62:
50:
46:
42:
38:
30:
26:
21:
3042:
2998:
2979:
2973:
2938:
2934:
2924:
2881:
2877:
2867:
2840:
2836:
2826:
2801:
2797:
2790:
2755:
2751:
2741:
2732:
2723:
2686:
2682:
2672:
2648:
2635:
2600:
2596:
2583:
2548:
2544:
2534:
2517:
2513:
2507:
2494:. Retrieved
2490:the original
2480:
2472:the original
2467:
2458:
2449:
2440:
2425:
2396:
2390:
2379:. Retrieved
2375:the original
2365:
2343:(1): 81–91.
2340:
2336:
2330:
2303:
2297:
2254:
2250:
2240:
2205:
2201:
2191:
2161:(1): 22–31.
2158:
2154:
2120:
2116:
2110:
2075:
2071:
2061:
2050:. Retrieved
2046:the original
2035:
2010:
2006:
2000:
1971:
1965:
1922:
1918:
1908:
1897:. Retrieved
1893:
1881:
1867:
1840:
1834:
1807:
1801:
1791:
1783:
1773:
1748:
1744:
1738:
1713:
1709:
1703:
1670:
1666:
1660:
1631:
1625:
1606:
1596:
1579:
1575:
1569:
1542:
1508:
1504:
1483:. Retrieved
1471:
1461:
1440:
1432:
1382:
1371:(ADBAC) and
1365:
1333:
1326:
1303:
1276:
1242:trigonelline
1223:
1214:gibberellins
1208:
1180:
1077:
1055:and aqueous
1042:
1032:
1028:
1021:mycobacteria
1006:
932:
897:
892:
882:
868:strips, the
832:
829:Applications
795:
784:propyl group
757:
712:methyl group
631:
605:Permanganate
586:
566:nucleophiles
551:
234:
224:
205:
129:
108:
104:
100:
73:ammonium ion
44:
40:
34:
3070:Food safety
2884:: 163–170.
2752:Anaesthesia
2155:ChemMedChem
2040:Abedon ST.
1667:ChemSusChem
1108:guanidinium
1104:imidazolium
1100:ethoxylated
1002:dequalinium
959:cetrimonium
839:surfactants
822:butyl group
746:ethyl group
669:, and as a
3054:Categories
2381:2009-06-04
2052:2020-02-14
2013:(1): 1–6.
1991:3527306730
1899:2023-01-08
1751:(4): 308.
1716:(4): 229.
1601:Smith MB,
1560:0471238961
1485:2022-02-17
1425:References
1393:chloroform
1092:hydrolysis
1053:chloroform
1009:endospores
990:SARS-CoV-2
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667:surfactant
208:alkylation
156:SARS-CoV-2
136:detergents
93:quaternary
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2589:Zeisel SH
2357:195343430
1939:2328-8930
1480:0362-4331
1305:Carnitine
1234:carnitine
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988:(such as
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963:cetrimide
910:Medicines
866:anticling
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1025:biofilms
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889:COVID-19
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