112-02-7

Basic information

• Product Name: N-Hexadecyltrimethylammonium chloride
• Synonyms: barquatct29;cationpb40;cetac;cetyl;dehyquarta;dodigen1383;genaminctac;hexadecyltrimethyl-ammoniuchloride
• CAS NO: 112-02-7
• Molecular Formula: C₁₉H₄₂N*Cl
• Molecular Weight: 320
• EINECS: 203-928-6
• Product Categories: Hair Care;Home Care;Alkylamine Salts & Quarternary Ammonium Salts (Surfactants);Ammonium Chlorides (Quaternary);Biochemistry;Cationic Surfactants;Cationic Surfactants (for Biochemistry);Functional Materials;Quaternary Ammonium Compounds;Surfactants;Surfactants (for Biochemistry);Water Ttreatment Chemicals;Quaternary ammonium salt;Piperidines ,Piperazines ,Homopiperidines
• Mol File: 112-02-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 232-234 °C
• Boiling Point: 475.54°C (rough estimate)
• Appearance: White/Amorphous Powder
• Density: 0.968 g/mL at 25 °C
• Vapor Pressure: 0.006Pa at 25℃
• Refractive Index: n20/D 1.3778
• Storage Temp.: -196°C
• Water Solubility: Soluble
• BRN: 3657974
• CAS DataBase Reference: N-Hexadecyltrimethylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hexadecyltrimethylammonium chloride(112-02-7)
• EPA Substance Registry System: N-Hexadecyltrimethylammonium chloride(112-02-7)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 38-41-50-50/53-37/38-22-43-36/37/38
• Safety Statements: 26-39-60-61-37/39-36
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• RTECS: ML9145000
• F: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 112-02-7(Hazardous Substances Data)

Usage

Chemical Properties

Liquid

Uses

Different sources of media describe the Uses of 112-02-7 differently. You can refer to the following data:
1. Barquat(R) CT-29 is a quaternary ammonium based surfactant that finds uses in broad number of industrial cleaning products. Product Data Sheet
2. Carsoquat(R) 450I is used in hair care formulations, as hair conditioner, cream rinse ingredient..
3. Carsoquat(R) CT-425 is used in hair care formulations, as hair conditioner, cream rinse ingredient..
4. Carsoquat(R) CT-429 is used in hair care formulations, as hair conditioner, cream rinse ingredient..
5. cetrimonium chloride can be incorporated into a cosmetic preparation for any number of formulatory needs including as an anti-static, an emulsifier, and a surfactant. It can also be used as a preservative and anti-microbial against the proliferation of bacteria, fungi, and yeast.

Definition

ChEBI: The organic chloride salt of cetyltrimethylammonium.

General Description

Colorless to pale yellow liquid with an odor of rubbing alcohol. Floats or sinks in water.

Reactivity Profile

Acidic salts, such as N-Hexadecyltrimethylammonium chloride, are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.

Hazard

A poison by ingestion and skin contact.

Health Hazard

Ingestion may produce toxic effects. Contact with eyes or skin may cause severe damage.

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise the chloride from acetone/ether mixture, EtOH/ether, or from MeOH. [Moss et al. J Am Chem Soc 109 4363 1987, Beilstein 4 IV 819.]

InChI:InChI:1S/C19H42N.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4;/h5-19H2,1-4H3;1H/q+1;/p-1

Synthetic route

methylene chloride (74-87-3) + N,N-dimethylhexadecylamine (112-69-6) → cetyltrimethylammonium chloride (112-02-7)

Conditions	Yield
With Petroleum ether at 80℃;

1-Chlorohexadecan (4860-03-1) + trimethylamine (75-50-3) → cetyltrimethylammonium chloride (112-02-7)

Conditions	Yield
With ethanol at 100 - 105℃;
In isopropyl alcohol for 72h; Heating;

hexadecylamine (143-27-1) → cetyltrimethylammonium chloride (112-02-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous ethanol 2: petroleum ether / 80 °C View Scheme

1,2,4-Triazole (288-88-0) + cetyltrimethylammonium chloride (112-02-7) → hexadecyltrimethylammonium 1,2,4-triazolate (1256752-07-4)

Conditions	Yield
In methanol at 20℃; Alkaline conditions;	99%

MCPA (94-74-6) + cetyltrimethylammonium chloride (112-02-7) → hexadecyltrimethylammonium (4-chloro-2-methylphenoxy)acetate (1082249-42-0)

Conditions	Yield
Stage #1: cetyltrimethylammonium chloride With potassium hydroxide In methanol for 0.166667h; Stage #2: MCPA In methanol at 25℃;	98%
With sodium hydroxide In water at 20℃; for 2h;

3,6-dichloro-O-anisic acid (1918-00-9) + cetyltrimethylammonium chloride (112-02-7) → C19H42N(1+)*C8H5Cl2O3(1-)

Conditions	Yield
Stage #1: cetyltrimethylammonium chloride With potassium hydroxide In methanol for 0.166667h; Stage #2: 3,6-dichloro-O-anisic acid In methanol at 25℃;	98%

N-(phosphonemethyl)glycine (1071-83-6) + cetyltrimethylammonium chloride (112-02-7) → C19H42N(1+)*C3H7NO5P(1-)

Conditions	Yield
Stage #1: N-(phosphonemethyl)glycine With sodium hydroxide at 50℃; Stage #2: cetyltrimethylammonium chloride In water at 20℃; for 1h;	98%

1H-4(5)-nitroimidazole (3034-38-6) + cetyltrimethylammonium chloride (112-02-7) → hexadecyltrimethylammonium 4-nitroimidazolate (1256752-10-9)

Conditions	Yield
In methanol at 20℃; Alkaline conditions;	97%

2,4-Dichlorophenoxyacetic acid (94-75-7) + cetyltrimethylammonium chloride (112-02-7) → n-hexadecyltrimethylammonium (2,4-dichlorophenoxy)acetate

Conditions	Yield
Stage #1: cetyltrimethylammonium chloride With potassium hydroxide In methanol for 0.166667h; Stage #2: 2,4-Dichlorophenoxyacetic acid In methanol at 25℃;	97%

1,2,3-Benzotriazole (95-14-7) + cetyltrimethylammonium chloride (112-02-7) → hexadecyltrimethylammonium benzotriazolate (1256752-04-1)

Conditions	Yield
In methanol at 20℃; Alkaline conditions;	96%

(RS)-2-(4-chloro-o-tolyloxy)propionic acid (93-65-2) + cetyltrimethylammonium chloride (112-02-7) → hexadecyltrimethylammonium (+/-)-2-(4-chloro-2-methylphenoxy)propionate (1354726-01-4)

Conditions	Yield
Stage #1: cetyltrimethylammonium chloride With potassium hydroxide In methanol for 0.166667h; Stage #2: (RS)-2-(4-chloro-o-tolyloxy)propionic acid In methanol at 25℃;	96%

chloroamine-T (127-65-1) + cetyltrimethylammonium chloride (112-02-7) → C19H42N(1+)*C7H7ClNO2S(1-)

Conditions	Yield
In water at 5℃; for 5h;	94%

cetyltrimethylammonium chloride (112-02-7) + 2-methyl-4-nitro-1H-imidazole (696-23-1) → hexadecyltrimethylammonium 2-methyl-4-nitroimidazolate (1256752-14-3)

Conditions	Yield
In methanol at 20℃; Alkaline conditions;	94%

cetyltrimethylammonium chloride (112-02-7) + 2-amino-2-cyanopropane (19355-69-2) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Conditions	Yield
With sodium hypochlorite	93.8%

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + cetyltrimethylammonium chloride (112-02-7) → cetyltrimethylammonium naproxenate

Conditions	Yield
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With sodium hydroxide Stage #2: cetyltrimethylammonium chloride In isopropyl alcohol for 4h; Reflux;	93.1%

bismuth(III) nitrate + water (7732-18-5) + cetyltrimethylammonim bromide (57-09-0) + cetyltrimethylammonium chloride (112-02-7) → BiOCl0.8Br0.2

Conditions	Yield
With acetic acid at 20℃; for 0.5h;	91%

N-(phosphonemethyl)glycine (1071-83-6) + cetyltrimethylammonium chloride (112-02-7) → bis(N,N,N-trimethyl-N-hexadecylammonium) glyphosate

Conditions	Yield
Stage #1: cetyltrimethylammonium chloride With sodium carbonate In acetonitrile at 30℃; for 3h; Stage #2: N-(phosphonemethyl)glycine In acetonitrile at 25℃; for 5h;	91%

iron(III) chloride + cetyltrimethylammonium chloride (112-02-7) → trimethylhexadecylammonium tetrachloroferrate(III) (105010-94-4)

Conditions	Yield
In ethanol Heating;	90%

Nb(CO)6 (12215-29-1) + Na2Se4 + cetyltrimethylammonium chloride (112-02-7) → ((CTA)2NbSe4)

Conditions	Yield
Stage #1: Nb(CO)6; Na2Se4 In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere; Stage #2: cetyltrimethylammonium chloride In N,N-dimethyl-formamide at 70℃; Inert atmosphere;	88.2%

Na2Se4 + cetyltrimethylammonium chloride (112-02-7) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → ((CTA)2MoSe4)

Conditions	Yield
Stage #1: Na2Se4; molybdenum hexacarbonyl In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere; Stage #2: cetyltrimethylammonium chloride In N,N-dimethyl-formamide at 70℃; Inert atmosphere;	86%

25Na(1+)*Li(1+)*2K(1+)*8Mo(2+)*8O(2-)*8S(2-)*4HO(1-)*131H2O*H8P8W48O184(32-) + water (7732-18-5) + cetyltrimethylammonium chloride (112-02-7) → 18C19H42N(1+)*2Na(1+)*6Li(1+)*2K(1+)*8Mo(2+)*8O(2-)*8S(2-)*4HO(1-)*36H2O*H8P8W48O184(32-)

Conditions	Yield
With lithium chloride In chloroform for 1h;	85%

1-bromo-12-cyclohexyldodecane (111040-44-9) + cetyltrimethylammonium chloride (112-02-7) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 1-(12-cyclohexyldodecyloxy)-2,3-propanediol

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol; hexane	74%
With hydrogenchloride; sodium hydroxide In methanol; hexane

phosphotungstic acid + cetyltrimethylammonium chloride (112-02-7) → C19H42N(1+)*PW4O24(1-)

Conditions	Yield
Stage #1: phosphotungstic acid With dihydrogen peroxide In water at 20℃; for 2h; Green chemistry; Stage #2: cetyltrimethylammonium chloride In ethanol; water at 40℃; Green chemistry;	72.3%

CH(COC4H3NC6H2(O(CH2)15CH3)3)2BF2 + cetyltrimethylammonium chloride (112-02-7) → C19H42N(1+)*C119H209BClF2N2O8(1-)

Conditions	Yield
In 1,4-dioxane Heating;	70%

1-bromo-2,2-dimethoxyethane (7252-83-7) + cetyltrimethylammonium chloride (112-02-7) + 3-benzyloxy-2-hydroxypropyl octadecyl ether (108225-24-7) → 3-benzyloxy-2-(2,2-dimethoxyethoxy)propyl octadecyl ether (111040-58-5)

Conditions	Yield
With sodium hydroxide at 85℃; for 20h;	64%

1-bromo-2,2-dimethoxyethane (7252-83-7) + hexane-ethyl acetate-acetone + cetyltrimethylammonium chloride (112-02-7) + 2-(benzyloxy)-3-(octadecyloxy)-1-propanol (86008-21-1) → 3-benzyloxy-2-(2,2-dimethoxyethoxy)propyl octadecyl ether (111040-58-5)

Conditions	Yield
With sodium hydroxide In hexane	64%

1-(12-cyclohexyldodecyloxy)-3-trityloxy-2-propanol + 1-O-(12-cyclohexyl)dodecyl-2-O-methylglycerol (111040-46-1) + cetyltrimethylammonium chloride (112-02-7) + benzyl chloride (100-44-7) → 2-Benzyloxy-3-(12-cyclohexyldodecyloxy)propanol (111040-48-3)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In tetrahydrofuran; 1,4-dioxane; hexane	45%

3-chloromethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione + cetyltrimethylammonium chloride (112-02-7) → 3-Cyanomethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione

Conditions	Yield
In dichloromethane; water; toluene	44.1%

pentacyanocyclopentadienyl anion sodium salt + cetyltrimethylammonium chloride (112-02-7) → C10N5(1-)*C19H42N(1+)

Conditions	Yield
In water for 0.166667h;	15%

vanadium (7440-62-2) + cetyltrimethylammonium hydroxide + phosphoric acid (86119-84-8, 7664-38-2) + cetyltrimethylammonium chloride (112-02-7) + vanadia → VP0.76O4.42(C16H33N(CH3)3)0.62*1.74H2O

Conditions	Yield
With HCl In water 85% H3PO4 added to aq. soln. of cetyltrimethylammonium hydroxide/chloride, followed by addition of V metal and V2O5 at room temp., stirred for 1h, pH of soln. adjusted to 3.36 with dilute HCl, suspension removed to an autoclave, kept at 473 K for 48 h; filtered, resulting powder washed with water, evacuation at room temp. for 5 h, elem. anal.;	4%

p,p'-DDT (50-29-3) + cetyltrimethylammonium chloride (112-02-7) → 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene (72-55-9)

Conditions	Yield
With sodium hydroxide In butan-1-ol at 25℃; Rate constant; dehydrohalogenation, effect of various alcohols (n-butyl and n-hexyl alcohol);

Upstream product

• 143-27-1 hexadecylamine 
• 4860-03-1 1-Chlorohexadecan 
• 75-50-3 trimethylamine 
• 74-87-3 methylene chloride 
• 112-69-6 N,N-dimethylhexadecylamine 

Downstream Products

• 111040-58-5 3-benzyloxy-2-(2,2-dimethoxyethoxy)propyl octadecyl ether 
• 72-55-9 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene 
• 74-87-3 methylene chloride 
• 16023-36-2 2-naphthalenesulfonate 
• 14002-56-3 cetyltrimethylammonium fluoride 
• 342808-35-9 1,5-bis(2,6-dimethoxyphenyl)-1,4-pentadiene-3-one 
• 6673-14-9 1,5-bis-(4-dimethylamino-phenyl)-penta-1,4-dien-3-one 
• 16507-00-9 4-methyl-4-nitrovaleronitrile 
• 342808-28-0 3,5-Bis-(2,6-difluorobenzylidene)-1-methylpiperidin-4-one 
• 342808-36-0 1,5-Bis-(2,3-difluorophenyl)-penta-1,4-dien-3-one 
• 342808-25-7 3,5-Bis-(2-fluoro-3-α,α,α-trifluoromethylbenzylidene)-piperidin-4-one 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 16245-97-9 octadecyl glycidyl ether 
• 111040-48-3 2-Benzyloxy-3-(12-cyclohexyldodecyloxy)propanol 

Relevant articles and documents

The Pseudophase Model of Micellar Catalysis. Addition of Cyanide Ion to N-Alkylpyridinium Ions

Cationic micelles speed addition of cyanide ion to the 4 position of N-alkyl-3-carbamoylpyridinium bromide (alkyl = n-C12H25, n-C14H29, n-C16H33).At high concentration of cetyltrimethylammonium cyanide the reaction rates become almost independent of as substrate binding appraches completion.The rates of these reactions in 0.005 M CN- go through maxima with increasing concentration of cetyltrimethylammonium bromide .The rate-surfactant profiles in both surfactants fit a pseudophase model of micellar catalysis.Using measured binding of the substrates to micelles of CTABr, the second-order rate constants in the micellar pseudophase are almost the same as that in water.Thus, the entire rate enhancement is due to concentration of reactants in the micellar pseudophase.

STABLE COMPOSITIONS OF THIABENDAZOLE AND IODINE-CONTAINING FUNGICIDES

The present invention relates to stable compositions for the fungicidal equipment of thermoplastic polymers, in particular PVC, comprising thiabendazole, at least one iodine-containing fungicide and at least one epoxide and optionally further fungicidally active compounds, and also to methods for preparing these formulations and to uses thereof for the protection of thermoplastic polymers against attack and destruction by microorganisms. Moreover, the invention relates to mold-resistant PVC materials equipped with the compositions according to the invention.

ACTIVE DELIVERY SYSTEMS FORMULATIONS

The present invention relates to active delivery system formulations, and methods of making and using the same. Said formulations, when applied to a substrate surface, form a protective coating on the surface and permit constituent active agents to act on the surface and in the surrounding medium.

3-NITROISOXAZOLES AND THEIR USE IN THE PROTECTION OF MATERIALS

The 3-nitroisoxazoles of the formula (I) in which R1 and R2 are each as defined in the description, some of which are known, are highly suitable for use as biocides for protecting industrial materials.