The document describes the market potential of quaternary ammonium compounds. Its application as disinfectant for various types of virus, bacteria, fungus and algae. It explains the preparation of benzalkonium chloride, cetyl pyridinium chloride, tallow alkyl dimethyl ammonium chloride,etc. It also explains the formulations as home care,hand wash, wipes, etc..

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Quaternary ammonium compounds
- Market and Production
Chandran Udumbasseri, Technical Consultant
Chandran.udumbasseri@gmail.com; cudumbasseri@yahoo.co.in.
QAC Market- Introduction
Quaternary ammonium compounds, also known as quats, belong to anti-microbial;
compounds that are potent in disinfectant activity. QACs eliminate gram positive and
gram negative bacteria. QACs are solids which are soluble in water forming
colourless and non-irritating deodorants and cationic disinfectants. They are used
alone or in combination and added to cleaning products. The use of personal care
products has increased the market of QACs. QAC acts as disinfectants, fabric
softeners, surfactants, wood preservatives and antistatic agents.
As personal products it is used as conditioning agents in clothes, skin and hair
softeners. It is used as disinfectants in food industry. They are used in toilet
cleaners, shampoos, shaving creams, hand soaps, body washes anti-cling, dryer
sheets, etc.
Health risks associated with QAC are fertility issues, birth defects, allergy, irritation,
etc. QAC can cause asthma and breathing troubles.
The global demand is expected to grow at a rate of CAG 6.8%
In hospitals, especially surgical depts., an increase in caesarean delivery,
appendicitis operation and cosmetic surgery the need for these products are
increasing; the cleaning of surgical instruments augments the demand for cleaning
and disinfection. In US 1.3 million children every year bare born through caesarean
operation.
The wide spread of coved pandemic have fuelled the demand of high quality surface
disinfectants due to the urge in hospitals and other public places. Pharmaceutical
grade highly pure products with maximum absorption are in demand. Pharmaceutical
products should be >99% and more pure without additives like fillers, binders, dyes,
etc. in 2019 pharmaceutical grade held a market of >68%.
QACs are very famous for their antiseptic property in the use of topical products
such as cream, liquids and gels. They act on a wide range of microorganisms,
yeasts, molds and gram positive and gram negative bacteria. They can work at all
pH and soluble in aqueous and oily phases disinfectants dominated 25% market in
2019.customers are used to order materials online at company price with variety and
markets brands of goodwill which is a time saving retail process for the customers.

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In Europe QACs are used as disinfectants bas pesticides. But the entry of pesticides
in the food chain is restricted to 0.1mg per Kg based on health risk assessment.
Europe finds a growth rate of CAG 7%, QACs are effective as non-tainting with some
detergent property. So they provide both disinfection and cleaning. They cause
minimum corrosion to the material of construction used in food processing. QACs
are utilized for soil removal and fabric softening in laundry detergents.
Mono alkonium salts used in fabric softening was >16% in 2019. Diethylene triamide
compounds are more biodegradable compared to dialkonium salts
The use of QACs in agriculture, oil & gas, textile, leather and use of end-use
products such as food, beverage, paints and coatings will propel the market demand.
The global market for disinfectants is propelled to reach USD 1.25 billion by 2024
from 0.84 billion in 2019.
The surface disinfectant market is based on liquids, wipes, and sprays. Single use
disinfectant wipes form the faster growing market segment. Wipes offer several
advantage like zero water consumption, lesser chance of cross contamination and
ease of use.
Based on application in-house surface segments like instrument disinfection of
hospitals in acquired infection and high volume of requirements in cleaning the
surface are major segments of application. Hospital settings, diagnostic labs,
pharmaceutical and biotechnology companies and research laboratories are the
areas where the disinfectant consumption is in bulk. Out of all hospital settings
where HAI (hospital acquired infection) cause large volume of patients. The stringent
regulations in hospital settings promote use of surface disinfectants to reduce the
rate of HAIs.
DuPont, Clariant AG, KAO Corporation, Merck KGaA, Huntsman, BASF SE, Croda,
Xiamen Pioneer Technology, Evonik Industries AG, and Novo Nordisk Pharmatech
A/S are the major manufacturers of the product and good profit makers.
Disinfection
Environmentally compatible disinfecting processes are mainly based on the use of
active oxygen compounds, such as hydrogen peroxide. Hydrogen peroxide is an
effective disinfectant and at 25mg/l it inhibits bacterial growth but for very effective
result high concentration with UV radiation is required. When infecting large volumes
of water the requirements and cost increases substantially and impractical and
uneconomical.
Bactericides used for sterilizing water are very useful in commercial applications.
The given treatment should control growth of sulphate reducing bacteria as these
organisms cause carrion to pipelines. These bacteria reduce rapidly sulphate to
sulphide which causes plugging in pipelines and formation.

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It was found that when small amount of a few selected bactericide is added to
hydrogen peroxide, they together form synergistic effect promoting very effective
performance as bactericide at low concentration.
Adding 1 to 1,000 p. p.m. (parts per million) of an alkyl quaternary ammonium salt
bactericide, wherein the alkyl radical has less than 20 carbon atoms, and a small but
synergistic adjuvant amount, preferably from 1 to 1,000 ppm of hydrogen peroxide
gives excellent bactericide effect
It further mixing 10 ppm. of hydrogen peroxide and 20 ppm. of the bactericide, i.e. a
synergistic combination with a hydrogen peroxide/bactericide ratio of 0.5, is quite
effective
Phenols as bactericides
Bius phenols, tris phenols and chlorinated (halogenated) phenols such as 2,2'-
methylene bis-4-chlorophenol, sodium pentachlorophenate,and 2,2'-methylene bis-4-
bromo phenol
Alkyl ammonium salts (QACs)
The alkyl radical may be paraffinic, olefinic, diolefinic, acetylinic, or otherwise
unsaturated.cetylinic, or otherwise unsaturated.
Examples,
Dioctyl dimethylammonium chloride, didodecyl dimethylammonium chloride, dodecyl
tri methylammonium chloride, dihexadecyl dimethylammoni um chloride, hexadecyl
trimethylammonium chloride, dioctadecyl dimethylammonium chloride, octadecyl tri
methylammonium chloride, dioctadecenyl dimethylammonium chloride,
dioctadecadienyl dimethylammonium chloride, hexadecyl octadecyl
dimethylammonium chloride, octadecynyl trimethylammonium bromide, hexa decynyl
trimethylammonium iodide, and octyl trimethyl ammonium fluoride
.
Mixtures
Tallow trimethylammonium chloride and di-coconut dimethyl ammonium chloride in
50% propanol
Amines
Decyl amine, dodecyl amine, tetradecyl amine, hexadecyl amine, octadecxyl amine,
octadecenyl amine, octdecadienyl amine, octadecenylamine chloride, dodecyl amine
bromide and dodecyl amine phosphate
,
QAC Structure
Basic structure

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Efficacy
Many antimicrobial products contain mixtures of QACs and other adjuncts to
increase their efficacy or to target a specific group of organisms. The wide variety of
chemical structures possible with QACs has allowed an evolution of their
effectiveness and an expansion of their applications over the last century. This has

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resulted in a continued increase in efficacy while reducing costs and lowering
toxicity.
QACs are used for all the below bacteria, virus, protozoa, fungus and algae.
Bacteria
1. Gram/Gram
2. Mycobacterium
3. Bacillus spores
4. Listeria monocytogenes
5. Antibiotic resistant
Virus
1. Enterovirus
2. Rotavirus
3. Norovirus
4. Influenza virus
5. Hepatitis A virus
Protozoa
1. Aconthamoeba polyphaba
2. Cryptospondium parvum
Fungus
1. Trichophyton
Algae
Mechanism of action
QACs are membrane-active agents (i.e., with a target site predominantly at the
cytoplasmic (inner) membrane in bacteria or the plasma membrane in yeasts).
(i) adsorption and penetration of the agent into the cell wall;
(ii) reaction with the cytoplasmic membrane (lipid or protein) followed by
membrane disorganization;
(iii) leakage of intracellular low-molecular-weight material;
(iv) degradation of proteins and nucleic acids; and
(v) wall lysis caused by autolytic enzymes. There is thus a loss of structural
organization and integrity of the cytoplasmic membrane in bacteria,
together with other damaging effects to the bacterial cell
Preparation of quaternary ammonium halide salt
a. Amination Reaction to form a Tertiary Amine
Alkyl chloride + Alkyl methylamine => Dialkylmethylamine
 A mixture of 1 mole of alkylmethylamine, 1 mole of alkyl chloride and 1.17
moles of 50% caustic soda, was taken in a 2liter reaction flask
 Heated the mixture to 190o
C and continued heating for 6 hours
 Cooled the reaction mixture and washed with water.
 Purified the product by fractional distillation
b. Quaternization of tertiary amine with methyl chloride
Dialkyl methyl amine + methyl chloride => dialkyl dimethyl ammonium chloride
 Charged the autoclave with 1 mole of dialkyl methyl amine and pumped 1.1
mole of methyl chloride gas into the autoclave
 Added ethanol as solvent( or water can be used as solvent)

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 Heated the content to 85o
C to 105o
C and maintained for 4-5 hours
 The quaternary ammonium salt in solution was discharged. Depending upon
the solvent added the solution would be 50-90% concentration
 The concentration of ethanol in the product could be 0-50%
Example1 : Decylisononyldimethyl ammonium chloride
a. Amination Reaction to form a Tertiary Amine
Isononyl chloride + Decylmethylamine => Decylisononylmethylamine
 A mixture of 300 moles of decylmethylamine, 300 moles of isononyl chloride
and 350 moles of 50% caustic soda, contained in a 190 Lts (50 gallon)
reactor, was heated for 6 hours at a temperature of 190°C.
 The organic mixture was cooled, washed with water and further purified by
fractional distillation.
 The amination process afforded a yield of 83% decylisononyl- methylamine
b. Quaternization of a Tertiary Amine with Methyl Chloride
Decylisononylmethylamine + Methyl chloride -> Decylisononyldimethyl ammonium
Chloride
 150 moles of decylisononyldimethylamine, contained in an autoclave, is mixed
with ethanol and/or water as solvent.
 Thereafter, 165 moles of methyl chloride gas is pumped into the autoclave
and the contents are heated at about 85-1 05°C for about 4-5 hours.
 Decylisononyldimethylammonium chloride, the quaternary ammonium salt
product, is left in solution, its concentration being about 50-90%, depending
upon the quantity of solvent used in the reaction.
 The concentration of ethanol in the quaternary ammonium salt product is 0-
50%, preferably between 0-20%..
Example 2: Cetyl pyridinium chloride
Recipe
1. Cetyl chloride 10Kg
2. Pyridine 28 Kg
Catalyst 0.2Kg Catalyst is a mixture of EDTA, N-methyl
morpholine, N,N-bis(carboxymethyl) glycine and phosphoric acid
Procedure
1. Charge above chemicals into a RB flask and heated to 100o
C
2. Maintain at this temperature for 6-8 hrs
3. Cool and filterand wash with ethyl acetate
4. The final product (12.6Kg) cetyl pyridinium chloride of 99.5% purity is
collected

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Example 3: Benzalkonium chloride
1. Alkyldimethyl amine 603g
2. Benzyl chloride 327g
3. Propylene glycol 436g
4. Water 419g
Procedure
1. Charge above chemicals (1,2,&3) to a 3 liter RB flask
2. Heat the mixture to 95-100o
C and maintain at this temperature for 5 hours
3. Add water to the reaction mixture and continue heating for additional 1 hour.
4. Cool the reaction mixture to RT
Example 4: Benzalkonium chloride
1. Dodecyl dimethylamine 5.39 kgs
2. Benzyl chloride 3.04 Kgs
3. Butyl glycol 33.3 lts
4. MIBK 66.7 Lts
Procedure
1. Take all the above chemicals in a reactor (250Lt)
2. Mix well to dissolve. If not dissolving heat to 80o
C for making a homogenous
solution.
3. Continue heating for 10hours
4. Cool to room temperature
5. The product will form as crystals and filter off
6. Recrystallize from Butyl glycol + MIBK mixture
7. 99% pure product can be separated.
Example 5: High yield Benzalkonium chloride
1. Dodecyl Dimethyl Amine 20 mol（5.39kg）；
2. Benzyl chloride 15 mol (1.89kg)；
3. Thiocarbamide (thiourea) 10 mol (0.76kg)；
4. Benzenediol 40L,
5. AEO (polyethoxyethylene ether fatty alcohol0： 60L.
Procedure
6. Take all the above chemicals in a reactor (250Lt)
7. Mix well to dissolve. If not dissolving heat to 80o
C for making a homogenous
solution.
8. Continue heating for 10hours
9. Cool to room temperature

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10.The product will form as crystals and filter off
11.Recrystallize from benzenediol + AEO mixture
12.99% pure product can be separated.
Aqueous compositions based on quaternary ammonium salts
Preparation of a concentrate formulation
The following manufacturing steps are performed in a polyethylene vessel and with
equipment (e.g. passivated stainless steel stirring apparatus) which are resistant to
hydrogen peroxide. The apparatus and equipment is beforehand cleaned well and
rinsed with demineralized water with conductivity < 10 μS/ cm.
1. 2500 grams of a 50% by weight hydrogen peroxide is added to 2425 grams of
demineralized water with conductivity <10 μS/cm.
2. While stirring, there is added, as a stabilizer, 0.5 gram of a diethylene triamine
penta(methylenephosphonate) sodium salt as a 33% solution in water and,
one minute thereafter, 80.8 grams of didecyldimethylammonium chloride in
the form of a solution in water and isopropanol.
3. Finally, the formulation is stirred for about 15 minutes until a transparent
homogeneous product is obtained
Formulation
The formulation has the following (weight by weight) composition:
1. Water - 73.0 %,
2. Hydrogen peroxide,- 25.0 %
3. Stabilizer - 0.002 %,
4. Monomeric quaternary ammonium compound,- 0.75 %
5. Isopropanol - 0.75 %
An aqueous disinfecting liquid composition containing hydrogen peroxide, one or
more monomeric quaternary ammonium compounds and an amount of water to
make up to 100%, with below mentioned characteristics. :
 The weight ratio of hydrogen peroxide to the monomeric quaternary
ammonium compounds in the composition is from 0.1 to 50 weight %.
 The viscosity of the said liquid composition is < 20 mPa.s.
 The molecular weight of the monomeric quaternary ammonium compound is
not above about 600.
It may contain the following:
 Stabilizers
 Corrosion inhibitors
 Fragrances.
Fabric softening
 There are three types of commercial products of QACs for fabric softening
 4-8 wt % dispersion of quaternary ammonium compound is added to the rinse
cycle of the washing process by the washing machine user.

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 The second commercial product is a quaternary ammonium compound
formulation applied to a nonwoven sheet or a polyurethane foam
 This product formulation contains a transfer agent, usually a fatty-acid ester,
which allows the quaternary ammonium com- 40 pound to transfer from the
substrate to the wet clothes
 The third type of product is a combined detergent, softener and antistatic
formulation containing quaternary ammonium compounds, which allows the
introduction of all necessary ingredients into the wash cycle of the washing
process
 In all cases, the benefits to the user are fabric softening, anti- static
properties, ease of ironing, and odor improvement, the latter because of the
common addition of perfumes to the formulation
 The most widely used, and most effective, quaternary ammonium compounds
used for fabric softening pur- 45 poses are the dimethyl bis[hydrogenated
tallow] ammonium chlorides and methyl sulfates
Hair treatment
 Another significant use for quaternary ammonium compounds is in certain
cosmetics, particularly for hair treat- ment.
 Quaternaries have a high affinity for proteinaceous substrates,
 They impart antistatic effects, increase hair wetting, improve wet and dry
combing, and improve feel and luster.
Deinking wastepaper
Quaternary ammonium compounds is used as deinking chemicals by aqueous
flotation process utilizing organo-clays which is formed in situ in the deinking
apparatus by the use of QAC,
.
Example 6: Tallow alkyl 2-ethyl hexyl methyl ammonium chloride
1. Tallow amine 341.9g
2. Palladium on carbon catalyst 1.7g (0.5%)
3. 2-ethyl hexylaldehyde 123.6g
Quaternization
1. Above amine 271.5g
2. Isopropyl alcohol 79.1g
3. Sodium carbonate 76.2g
4. Sodium bisulfite 2g
Procedure
1. Add 1&2 into a pressure autoclave and purge the reactor with nitrogen and
vent three times
2. Heat the content to 135o
C
3. Pressurize to 300psig with hydrogen
4. Add 2-ethylhexyl aldehyde gradually over a period of three hours
5. Draw a sample and check GS chromatography for 94% coversion to
secondary amine

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6. Digest the reaction mixture for further 2-3hours at 135oC
7. Pressurize the reactor with hydrogen at 400psig
8. Discharge the reaction mixture next day.
9. Separate water layer and use secondary amine for reaction with methyl
chloride
10.2-ethylhexanal was added gradually and at a substantially uniform rate over
the next three hours.
Quaternization
1. Add items 1-4 into an autoclave. Purge with nitrogen
2. Heat the autoclave to 100o
C
3. Add methyl chloride until the pressure is 180psig
4. Continue the temperature and pressure for additional 5houirs for reaction
completion
5. Discharge the content and separate water to get the final product.
Residual disinfection
The present world witnesses many unknown diseases that are infected through
environment, people, animals, other living beings who are carriers. The immunity
system of human beings is continuously getting reduced and the healthcare world
fails to find a medicine, antidote for these diseases.
Healthcare
Hospitals and healthcare systems where cross contamination and spreading through
individuals diseases are at higher risk level and cause Hospital Acquired Infection,
also called nosocomial infection. This type of infection cause severe pneumonia,
urinary track infection, etc due to fungus and bacteria.
In US such hospital associated infection was reported to 1.7 million cases and 1
million deaths every year. Gram negative bacterial infection was reported in Europe
to instances with 9000 to 10000 deaths every year.. hospital and healthcare facilities
care more for serious cases with negligence to nosocomial infections which cause
severe spreading of such patients un-monitored. The six ESKAPE pathogens are
antibiotic resistant and are nosocomial infection brooders. HAIs are direct or indirect
contact transmitting infections. Indirect transmission results from contact with
contaminated object or surface.
Home care & household environment also breed microbe and the use of
disinfectants may not totally remove microbes from surfaces and possibility of re
contamination. So for a home care and household cleaner that kills microbes quickly
on contact, then acts as a residual disinfectant but yet does not have this
undesirable sticky or tacky effect is the ideal one.
Food service industry faces contamination at work place. Here also disinfectants
with residual activity are more applicable.
Biofilms are a layer of microorganisms adhering to a surface. Usually existing
disinfectants cannot work with such films on the surface.
In summary, formulations which can to confer a residual biocidal activity to treated
surfaces are needed. If the formulations were combined with a surface disinfectant ,
to enable a single cleaning to both disinfect and impart the residual biocidal effect
would be more practical

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Home care uses
Recommended formulation with residual disinfection,
Ethanol 70%
Polyethyloxazoline 2%
Quaternary ammonium compound 0.8-1.2%
Wetting agent / Surfactant. 0.1
Water 27%
Wipes
 Wipe is made out of natural material , synthetic material, linen , silk , wool ,
hemp , flax, polypropylene , polystyrene , polyester , nylon , rayon , acrylic , or
spandex , made of water absorbent or water adsorbent and woven or non -
woven
 Contains combination of quaternary ammonium compounds in a ratio to poly (
2 - ethyl - 2 - oxazoline ) of 1 : 4 to 1 : 1. The quaternary ammonium
compound is in an amount of at least 0. 2 weight percent
 The poly ( 2 ethyl - 2 - oxazoline ) is in an amount of 1 weight % to 5 weight%
 The surfactant is an alcohol ethoxylate (linear alcohol ethoxylate with at least
9 moles of ethylene oxide) in an amount of 0 . 05 weight % to 0 . 5 weight%
 The fragrance is in an amount of 0 weight % to 0 . 5 weight % ,
A wipe is having a residual biocidal property,
Wipe formulation
Water soluble polymer 1.50
Alkyl dimethyl benzylammonium chloride
and dialkyl dimethyl ammonium chloride
QAC mixture 1.40
Alcohol ethoxylate 9 ethylene oxide 0.20
Fragrance 0.10
Water balance
Hard surface disinfectant against SARS CoV2 the noval coronavirus that causes the
disease COVID 19

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Costing
Alkyldimethyl benzyl chloride
Raw material price
Alkyl dimethyl amine Rs 170/Kg
Benzyl chloride Rs 175/Kg
Propylene glycol Rs 125/Kg
Water Rs 5/kg
Formulation
1. Alkyldimethyl amine 603Kg

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2. Benzyl chloride 327Kg
3. Propylene glycol 436Kg
4. Water 419Kg
---------
Total 2204 kg
URMC
1. Alkyl dimethyl amine 603x170 = 102510
2. Benzyl chloride 327x175 = 57225
3. Propylene glycol 436x125 = 54500
4. Water 419x5 = 2095
------------
Total 216330
Unit cost 216330/2204 = Rs 98.15/kg
Add interest for 3 months, 3.25 = 3.19
Factory overhead, 20% = 19.63
Profit margin 15% = 14.72
Price /Kg = 98.15+ 3.19+19.63+14.72 = Rs 135,69/Kg
Market price Rs 250 – 300/Kg
Generated by
Chandran Udumbasseri
Consultant