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Quaternary ammonium cation
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==Applications== Quaternary ammonium salts are used as [[disinfectant]]s, [[surfactants]], [[fabric softener]]s, and as [[antistatic agent]]s (e.g. in [[shampoo]]s). In [[liquid]] fabric softeners, the [[chloride]] salts are often used. In [[clothes dryer|dryer]] [[fabric softener|anticling]] strips, the [[sulfate]] salts are often used. Older aluminium [[electrolytic capacitors]] and [[Spermicide|spermicidal jellies]] also contain quaternary ammonium salts. Quats are also used in contraception formulations, veterinary products, diagnostic testing, vaccine production, and nasal formulations. <ref>{{Cite web|date=22 October 2021|title=Quats applications|url=https://novonordiskpharmatech.com/quats-applications/}}</ref> 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 [[United States Environmental Protection Agency]] suggested as effective against [[COVID-19]] contained one of the quats, and often a quat as the sole ingredient.<ref>{{Cite web | vauthors = Lim XZ |date=August 2, 2020 |title=Do we know enough about the safety of quat disinfectants? |url=https://cen.acs.org/safety/consumer-safety/know-enough-safety-quat-disinfectants/98/i30 |url-access=subscription |access-date=2023-01-08 |website=Chemical and Engineering News}}</ref> ''Salmonella'' and [[Escherichia coli O157:H7|''E. coli'' O157:H7]] exposed to quats have developed cross resistance to antibiotics. A subject of concern is the potential effect of increased use of quats related to [[COVID-19 pandemic]] on antibiotic resistance in a larger microbial community in nature and engineered environment.<ref>{{Cite journal | vauthors = Hora PI, Pati SG, McNamara PJ, Arnold WA |date=2020-09-08 |title=Increased Use of Quaternary Ammonium Compounds during the SARS-CoV-2 Pandemic and Beyond: Consideration of Environmental Implications |journal=Environmental Science & Technology Letters |language=en |volume=7 |issue=9 |pages=622–631 |doi=10.1021/acs.estlett.0c00437 |pmid=37566314 |issn=2328-8930 |pmc=7341688}}</ref> ===Medicines=== [[file:Butylscopolamine skeletal.svg|right|thumb|220px|[[Buscopan]] is one of many [[Antispasmodic|spasmo­lytics]] (anti-spasm drugs) that feature the quaternary ammonium [[functional group]].<ref>{{Ullmann |doi=10.1002/14356007.a24_515| title=Spasmolytics | year=2000 | vauthors = Bungardt E, Mutschler E | isbn=3527306730}}</ref>]] Quaternary ammonium compounds have antimicrobial activity.<ref>{{cite journal | vauthors = Jia Z, shen D, Xu W | title = Synthesis and antibacterial activities of quaternary ammonium salt of chitosan | journal = Carbohydrate Research | volume = 333 | issue = 1 | pages = 1–6 | date = June 2001 | pmid = 11423105 | doi = 10.1016/S0008-6215(01)00112-4 }}</ref> Quaternary ammonium compounds, especially those containing long alkyl chains, are used as [[antimicrobial]]s and [[disinfectant]]s. Examples are [[benzalkonium chloride]], [[benzethonium chloride]], methylbenzethonium chloride, [[cetalkonium chloride]], [[cetylpyridinium chloride]], [[cetrimonium]], [[cetrimide]], dofanium chloride, [[tetraethylammonium bromide]], [[didecyldimethylammonium chloride]] and [[domiphen bromide]]. Also good against [[fungi]], [[amoebas]], and [[viral envelope|enveloped]] [[viruses]] (such as [[COVID-19|SARS-CoV-2]]),<ref name=questionable>{{cite web |url=http://www.mansfield.ohio-state.edu/~sabedon/biol2032.htm |title=Specific Antimicrobials | vauthors = Abedon ST |publisher=Ohio State University |access-date=2020-02-14|url-status=dead |archive-url=https://web.archive.org/web/20081015002934/http://www.mansfield.ohio-state.edu/~sabedon/biol2032.htm |archive-date=2008-10-15 }}</ref><ref>{{cite journal | vauthors = Schrank CL, Minbiole KP, Wuest WM | title = Are Quaternary Ammonium Compounds, the Workhorse Disinfectants, Effective against Severe Acute Respiratory Syndrome-Coronavirus-2? | journal = ACS Infectious Diseases | volume = 6 | issue = 7 | pages = 1553–1557 | date = July 2020 | pmc = 7341688 | doi = 10.1021/acs.estlett.0c00437 | pmid = 32412231 }}</ref> most quaternary ammonium compounds are believed to act by disrupting the [[cell membrane]] or [[viral envelope]].<ref>{{cite journal | vauthors = Cocco AR, Rosa WL, Silva AF, Lund RG, Piva E | title = A systematic review about antibacterial monomers used in dental adhesive systems: Current status and further prospects | journal = Dental Materials | volume = 31 | issue = 11 | pages = 1345–1362 | date = November 2015 | pmid = 26345999 | doi = 10.1016/j.dental.2015.08.155 }}</ref> (Some QACs, such as [[dequalinium]] and similar bis-QACs, show evidence of a different mode of action.)<ref name=Tischer>{{cite journal |last1=Tischer |first1=Maximilian |last2=Pradel |first2=Gabriele |last3=Ohlsen |first3=Knut |last4=Holzgrabe |first4=Ulrike |title=Quaternary Ammonium Salts and Their Antimicrobial Potential: Targets or Nonspecific Interactions? |journal=ChemMedChem |date=2 January 2012 |volume=7 |issue=1 |pages=22–31 |doi=10.1002/cmdc.201100404|pmid=22113995 |s2cid=26326417 }}</ref> Quaternary ammonium compounds are lethal to a wide variety of organisms except [[endospores]] and [[non-enveloped virus]]es, both having no accessible membrane coat to attack. It is possible to solve the endospore problem by adding chemicals which force them to germinate.<ref>{{cite journal |last1=Nerandzic |first1=MM |last2=Donskey |first2=CJ |title=A Quaternary Ammonium Disinfectant Containing Germinants Reduces Clostridium difficile Spores on Surfaces by Inducing Susceptibility to Environmental Stressors. |journal=Open Forum Infectious Diseases |date=October 2016 |volume=3 |issue=4 |pages=ofw196 |doi=10.1093/ofid/ofw196 |pmid=28066792|pmc=5198585 }}</ref><ref>{{cite journal |last1=Tuladhar |first1=E |last2=de Koning |first2=MC |last3=Fundeanu |first3=I |last4=Beumer |first4=R |last5=Duizer |first5=E |title=Different virucidal activities of hyperbranched quaternary ammonium coatings on poliovirus and influenza virus. |journal=Applied and Environmental Microbiology |date=April 2012 |volume=78 |issue=7 |pages=2456–8 |doi=10.1128/AEM.07738-11 |pmid=22287007|pmc=3302582 |bibcode=2012ApEnM..78.2456T }}</ref> They have reduced efficacy against [[gram-negative bacteria]], [[mycobacteria]], and bacteria in [[biofilm]]s due to them having additional layers that need to be penetrated or disrupted. Some bacteria such as MRSA have acquired resistance genes, ''qacA/B'' and ''qacC/D'', that pump the cation out of the cell.<ref name=Tischer/> ===Phase transfer catalysts=== In organic chemistry, quaternary ammonium salts are employed as [[phase transfer catalyst]]s (PTCs). Such catalysts accelerate reactions between reagents dissolved in immiscible solvents. The highly reactive reagent [[dichlorocarbene]] is generated via PTC by reaction of [[chloroform]] and aqueous [[sodium hydroxide]].{{cn|date=August 2023}} [[File:Ion exchange resin beads.jpg|thumb|200px|[[Anion exchange]] resins, in the form of beads, contain quaternary ammonium ions bound to a polymer.<ref>{{cite book |doi=10.1002/14356007.a14_393.pub2|chapter=Ion Exchangers |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2008 |last1=De Dardel |first1=François |last2=Arden |first2=Thomas V. |isbn=978-3527306732|page=5 }}</ref>]] ===Fabric softeners and hair conditioners=== In the 1950s, [[distearyldimethylammonium chloride]] (DHTDMAC), was introduced as a [[fabric softener]]. 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 [[betaine]]-esters or ester-quats and are susceptible to degradation, e.g., by [[hydrolysis]].<ref>{{cite journal| vauthors = Hellberg PE, Bergström K, Holmberg K |title=Cleavable surfactants|journal= Journal of Surfactants and Detergents|date=January 2000|volume=3|issue=1|pages=81–91|doi=10.1007/s11743-000-0118-z|s2cid=195343430}}</ref> Characteristically, the cations contain one or two long [[alkyl]] chains derived from fatty acids linked to an [[ethoxylate]]d ammonium salt.<ref>{{cite web |url=http://www.henkelconsumerinfo.com |title=Henkel Consumer Info |publisher=Henkelconsumerinfo.com |access-date=2009-06-04 |archive-url=https://web.archive.org/web/20191018103004/http://www.henkelconsumerinfo.com/products/ |archive-date=2019-10-18 |url-status=dead }}</ref> Other cationic compounds can be derived from [[imidazolium]], [[Guanidinium cation|guanidinium]], substituted amine salts, or quaternary [[alkoxy]] ammonium salts.<ref name=Ullmann>{{Ullmann| vauthors = Smulders E, Sung E |title=Laundry Detergents, 2. Ingredients and Products|doi=10.1002/14356007.o15_013}}</ref> <gallery caption="Cationic surfactants used as fabric softeners" widths="220px" heights="100px"> File:C18x2Me2Cl.png|[[Distearyldimethylammonium chloride]], an early generation [[fabric softener]] with low [[biodegradability]] that was phased out. File:Redrawn diesterquat salt (methanesulfonate anion) related to fabric softeners.png|Another diesterquat, a contemporary fabric softener. File:AltDiesterquatCl.png|Diethyl ester dimethyl ammonium chloride used as a fabric softener. File:DiesterCl.png|Another diesterquat used as a fabric softener. </gallery> The antistatic qualities that make quaternary ammonium salts useful as fabric softeners also make them useful in [[hair conditioner]]s and [[shampoo]]s.<ref>{{CPID|id=1000|name=Distearyldimonium chloride}}</ref> The idea was pioneered by [[Henkel]] with a 1984 patent.<ref>{{cite web |title=Quaternary ammonium compound hair conditioners US4744977 |url=https://patents.google.com/patent/US4744977 |website=Google Patents |language=en |date=14 November 1985}}</ref> Examples include [[cetrimonium chloride]] and [[behentrimonium chloride]].<ref>{{cite web | url = http://www.naturallycurly.com/curlreading/curly-q-a/curlchemist-what-is-cetrimonium-chloride | title = What is cetrimonium chloride? | archive-url = https://web.archive.org/web/20120304041725/http://www.naturallycurly.com/curlreading/curly-q-a/curlchemist-what-is-cetrimonium-chloride | archive-date=2012-03-04 | work = naturallycurly.com | date = November 2007 }}</ref> ===Plant growth retardants=== [[Chlormequat|Cycocel]] (chlormequat chloride) reduces plant height by inhibiting the production of [[gibberellin]]s, 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.<ref>{{cite web|url=http://users.in.gr/dimpet/thesis/growth_retardants.htm |title=Growth Retardants |access-date=July 19, 2012 |url-status=dead |archive-url=https://web.archive.org/web/20110925004831/http://users.in.gr/dimpet/thesis/growth_retardants.htm |archive-date=September 25, 2011 }} Wageningen Agricultural University, The Netherlands</ref>
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