Quaternary

ammonium cation

In chemistry, quaternary ammonium

cations, also known as quats, are
positively-charged polyatomic ions of the
+
structure [NR4] , R being an alkyl group or
an aryl group.[1] Unlike the ammonium ion
+
(NH4) and the primary, secondary, or
tertiary ammonium cations, the quaternary
ammonium cations are permanently
charged, independent of the pH of their
solution. Quaternary ammonium salts or
quaternary ammonium compounds (called
quaternary amines in oilfield parlance) are
salts of quaternary ammonium cations.
Polyquats are a variety of engineered
polymer forms which provide multiple quat
molecules within a larger molecule.

Quaternary ammonium cation. The R groups may be the same or different alkyl or aryl groups. Also, the R groups may
be connected.
Quats are used in consumer applications
including as antimicrobials (such as
detergents and disinfectants), fabric
softeners, and hair conditioners. As an
antimicrobial, they are able to inactivate
enveloped viruses (such as SARS-CoV-2).
Quats tend to be gentler on surfaces than
bleach-based disinfectants, and are
generally fabric-safe.[2]

+
"Top" view of one view of Bu4N as determined by X-ray crystallography.[3]
 +
"Side" view of Bu4N as determined by X-ray crystallography.[3]

Synthesis
Quaternary ammonium compounds are
prepared by the alkylation of tertiary
amine. Industrial production of commodity
quat salts usually involves hydrogenation
of fatty nitriles, which can generate
primary or secondary amines. These
amines are then treated with methyl
chloride.[4]
The quaternization of alkyl amines by alkyl
halides is widely documented.[5] In older
literature this is often called a Menshutkin
reaction, however modern chemists
usually refer to it simply as
quaternization.[6] The reaction can be used
to produce a compound with unequal alkyl
chain lengths; for example when making
cationic surfactants one of the alkyl
groups on the amine is typically longer
than the others.[7] A typical synthesis is for
benzalkonium chloride from a long-chain
alkyldimethylamine and benzyl chloride:
Reactions
Quaternary ammonium cations are
unreactive toward even strong
electrophiles, oxidants, and acids. They
also are stable toward most nucleophiles.
The latter is indicated by the stability of
the hydroxide salts such as
tetramethylammonium hydroxide and
tetrabutylammonium hydroxide even at
elevated temperatures. The halflife of
Me4NOH in 6M NaOH at 160 °C is >61 h.[8]

Because of their resilience, many unusual

anions have been isolated as the
quaternary ammonium salts. Examples
include tetramethylammonium
pentafluoroxenate, containing the highly
−
reactive pentafluoroxenate (XeF5) ion.
Permanganate can be solubilized in
organic solvents, when deployed as its
+
NBu4 salt.[9][10]

With exceptionally strong bases, quat

cations degrade. They undergo
Sommelet–Hauser rearrangement[11] and
Stevens rearrangement,[12] 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 Hofmann elimination and
Emde degradation.

Benzalkonium chloride is a common type of quat salt used as a biocide, a cationic surfactant, and as a phase transfer
agent.[13] ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-
numbered alkyl chain lengths.

Examples
+
Tetramethylammonium ion: (CH3)4N ,
+
also denoted Me4N (Me = methyl
group)
+
Tetraethylammonium ion: (C2H5)4N ,
+
also denoted Et4N (Et = ethyl group)
 +
Tetrapropylammonium ion: (n-C3H7)4N ,
+
also denoted Pr4N (Pr = propyl group)
+
Tetrabutylammonium ion: (n-C4H9)4N ,
+
also denoted Bu4N (Bu = butyl group)

Applications
Quaternary ammonium salts are used as
disinfectants, surfactants, fabric softeners,
and as antistatic agents (e.g. in
shampoos). In liquid fabric softeners, the
chloride salts are often used. In dryer
anticling strips, the sulfate salts are often
used. Older aluminium electrolytic
capacitors and spermicidal jellies also
contain quaternary ammonium salts.
Quats are also used in contraception
formulations, veterinary products,
diagnostic testing, vaccine production, and
nasal formulations. [14]

Some scientists have raised concerns

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.[15]
Salmonella and 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.[16]

Medicines

Buscopan is one of many spasmo­lytics (anti-spasm drugs) that feature the quaternary ammonium functional group.[17]

Quaternary ammonium compounds have

antimicrobial activity.[18] Quaternary
ammonium compounds, especially those
containing long alkyl chains, are used as
antimicrobials and disinfectants.
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 enveloped viruses
(such as SARS-CoV-2),[19][20] most
quaternary ammonium compounds are
believed to act by disrupting the cell
membrane or viral envelope.[21] (Some
QACs, such as dequalinium and similar
bis-QACs, show evidence of a different
mode of action.)[22]

Quaternary ammonium compounds are

lethal to a wide variety of organisms
except endospores and non-enveloped
viruses, both having no accessible
membrane coat to attack. It is possible to
solve the endospore problem by adding
chemicals which force them to
germinate.[23][24] They have reduced
efficacy against gram-negative bacteria,
mycobacteria, and bacteria in biofilms 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.[22]

Phase transfer catalysts

In organic chemistry, quaternary

ammonium salts are employed as phase
transfer catalysts (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.
Anion exchange resins, in the form of beads, contain quaternary ammonium ions bound to a polymer.[25]

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.[26] Characteristically, the
cations contain one or two long alkyl
chains derived from fatty acids linked to
an ethoxylated ammonium salt.[27] Other
cationic compounds can be derived from
imidazolium, guanidinium, substituted
amine salts, or quaternary alkoxy
ammonium salts.[28]

Cationic surfactants used as fabric

softeners
Distearyldimethylammonium chloride, an
early generation fabric softener with low
biodegradability that was phased out.

Another diesterquat, a contemporary fabric

softener.
Diethyl ester dimethyl ammonium chloride
used as a fabric softener.

Another diesterquat used as a fabric

softener.
The antistatic qualities that make
quaternary ammonium salts useful as
fabric softeners also make them useful in
hair conditioners and shampoos.[29] The
idea was pioneered by Henkel with a 1984
patent.[30] Examples include cetrimonium
chloride and behentrimonium chloride.[31]

Plant growth retardants

Cycocel (chlormequat chloride) reduces

plant height by inhibiting the production of
gibberellins, 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.[32]

Natural occurrence
Several quanternary ammonium
derivatives exist in nature.[33] Prominent
examples include glycine betaine, choline,
carnitine. butyrobetaine, homarine, and
trigonelline. Glycine betaine, an osmolyte,
stabilizes osmotic pressure in cells.[34]

Glycine betaine is a naturally occurring quaternary ammonium cation. Its degradation product, trimethylamine, is
responsible for the odor of spoiled fish.
Choline is a quat compound.

Choline is a precursor for the

neurotransmitter acetylcholine. Choline is
also a constituent of lecithin, which is
present in many plants and animal
organs.[35] It is found in phospholipids. For
example, phosphatidylcholines, a major
component of biological membranes, are a
member of the lecithin group of fatty
substances in animal and plant tissues.[36]
Carnitine participates in the beta-oxidation
of fatty acids.

1-Oleoyl-2-palmitoyl-phosphatidylcholine

Health effects
Quaternary ammonium compounds can
display a range of health effects, amongst
which are mild skin and respiratory
irritation [37] up to severe caustic burns on
skin and the gastrointestinal wall
(depending on concentration),
gastrointestinal symptoms (e.g., nausea
and vomiting), coma, convulsions,
hypotension and death.[38]

They are thought to be the chemical group

responsible for anaphylactic reactions that
occur with use of neuromuscular blocking
drugs during general anaesthesia in
surgery.[39] Quaternium-15 is the single
most often found cause of allergic contact
dermatitis of the hands (16.5% in 959
cases).[40]
Possible reproductive effects in
laboratory animals

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
alkyl dimethyl benzyl ammonium chloride
(ADBAC) and didecyl dimethyl ammonium
chloride (DDAC).[41][42] A similar link was
tentatively identified in nurses.[43] The
studies contradict earlier toxicology data
reviewed by the U.S. Environmental
Protection Agency (U.S. EPA) and the EU
Commission.[44]

Quantification
The quantification of quaternary
ammonium compounds can be
challenging. Some methods include
precipitation of solid salts with
tetraphenylborate. Another method, an
Epton titration, involves partitioning
between water-chloroform in the presence
of an anionic dye. Individual cations are
detectable by ESI-MS and NMR
spectroscopy.[4]
See also
Ammonium

Benzyltrimethylammonium fluoride

Iminium

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Further reading
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". The Science of the Total
Environment. 518–519: 352–362.
Bibcode:2015ScTEn.518..352Z (https://ui.ad
sabs.harvard.edu/abs/2015ScTEn.518..352
Z) . doi:10.1016/j.scitotenv.2015.03.007 (htt
ps://doi.org/10.1016%2Fj.scitotenv.2015.03.
 007) . PMID 25770948 (https://pubmed.ncbi.
nlm.nih.gov/25770948) .

External links
"Toxicities of quaternary ammonium" (ht
tp://www.inchem.org/documents/pims/
chemical/pimg022.htm) . Internationally
Peer Reviewed Chemical Safety
Information (INCHEM). World Health
Organization.

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