Basic information
- Standard SMILES
CCCCCCCCCCCCCCCC[N+](C)(C)C.[Cl-]- InChIKey
WOWHHFRSBJGXCM-UHFFFAOYSA-M- Molecular formula
- C19H42N.Cl
- Average molar mass
- 320 g/mol
Overview
Hexadecyltrimethylammonium chloride appears as colorless to pale yellow liquid with an odor of rubbing alcohol. Floats or sinks in water. (USCG, 1999)
Names & identifiers
- Preferred name
- Hexadecyltrimethylammonium chloride
- IUPAC
- hexadecyl(trimethyl)azanium chloride
Names & synonyms
Show more names
Database identifiers
- CAS
112-02-7、68002-63-1- PubChem CID
- 8154
- DTXSID
DTXSID6026901- ChEMBL
CHEMBL1895807- ChEBI
CHEBI:53581- UNII
- UC9PE95IBP
- EC Number
- 203-928-6
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 15
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 181
Experimental & physicochemical properties
Cosmetics
Cosmetics ingredient -> Conditioning/Emollient; Emulsifier; Fragrance; Other (Specify); Preservative/Stabilizer; Solvent; Surfactant
Cosmetic ingredients (Cetrimonium Chloride) -> CIR (Cosmetic Ingredient Review)
Preservative
Physical Description
Hexadecyltrimethylammonium chloride appears as colorless to pale yellow liquid with an odor of rubbing alcohol. Floats or sinks in water. (USCG, 1999)
Liquid; CBI
Solution: Clear to pale yellow liquid; [HSDB] White powder; [MSDSonline]
Autoignition Temperature
750 °F (USCG, 1999)
750 °F /ISOPROPYL ALCOHOL SOLN OF CETYLTRIMETHYLAMMONIUM CHLORIDE/
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (5 of 1105) of reports.
Danger
H302 (49%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1105 reports by companies from 42 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: 1-Hexadecanaminium, N,N,N-trimethyl-, chloride
Hazard Traits - Hazard Trait Undefined
1-Hexadecanaminium, N,N,N-trimethyl-, chloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Hexadecanaminium, N,N,N-trimethyl-, chloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 25-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14219
Cetrimonium chloride: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
HEXADECYLTRIMETHYLAMMONIUM CHLORIDE is a quaternary ammonium compound. Therefore it has a permanently charged nitrogen atom with four alkyl or aryl groups on it. Compounds in this group are generally soluble in water and are near pH 7 (neutral). They do not undergo the acid-base reactions typical of primary, secondary, or tertiary ammonium ions.
Hazard Classes and Categories
Acute Tox. 4 (49%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 4
Acute toxicity (Oral) - Category 4
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Protective Action Criteria (PAC)
2.1 [mg/m3]
23 [mg/m3]
140 [mg/m3]
Personal Protective Equipment (PPE)
Goggles or face shield; rubber gloves (USCG, 1999)
GOGGLES OR FACE SHIELD; RUBBER GLOVES. /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/
Toxicology
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.2X10+5(SRC), determined from a structure estimation method(2), indicates that trimethylhexadecylammonium chloride is expected to be immobile in soil(SRC). Volatilization of trimethylhexadecylammonium chloride from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Trimethylhexadecylammonium chloride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-10 mm Hg(SRC), determined from a fragment constant method(4).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.2X10+5(SRC), determined from an estimation method(2), indicates that trimethylhexadecylammonium chloride is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 71(SRC), from its log Kow of 3.23(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate. The MITI, closed bottle, and Sturm tests revealed no degradation after 10 days, microbial growth after 17 days, and 84% degradation after 13 days, respectively(8). 10-20 ppm trimethylhexadecylammonium chloride was degraded with a half-life of 3.1 days in freshwater collected from the Ohio river 1 mile below discharge from a municipal treatment plant at 20 °C and pH 6.9(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethylhexadecylammonium chloride, which has an estimated vapor pressure of 2.8X10-10 mm Hg at 25 °C(SRC), using a fragment constant estimation method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase trimethylhexadecylammonium chloride may be removed from the air by wet and dry deposition(SRC).
Toxicity Summary
The CIR Expert Panel concluded the following ingredients are safe in the present practices of use and concentration described in the safety assessment when formulated to be non-irritating...Cetrimonium Chloride...
Safe for use in cosmetics, with qualifications
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for trimethylhexadecylammonium chloride can be estimated to be 2.2X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that trimethylhexadecylammonium chloride is expected to immobile in soil.
Human Toxicity Excerpts
VAPOR IRRITATING TO EYES, NOSE AND THROAT. HARMFUL IF INHALED. LIQUID IRRITATING TO SKIN AND EYES. HARMFUL IF SWALLOWED. /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/
Poison by intravenous route.
Artificial Pollution Sources
Trimethylhexadecylammonium chloride's production and use as a coagulant (antibiotic production), conditioning agent (hair products), antistatic agent (textile spin finishes), and softening agent (textile finishes)(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
THE CATIONIC SURFACTANTS BIODEGRADATION IN SEWAGE AND RIVER WATER WAS STUDIED, MEASURING THE REDUCTION OF THE ACTIVE SUBSTANCE BY A COLORIMETRIC METHOD USING SODIUM ALIZARINE SULFONATE.
The MITI, closed bottle, and Sturm tests revealed no degradation after 10 days, microbial growth after 17 days, and 84% degradation after 13 days, respectively(1). 10-20 ppm trimethylhexadecylammonium chloride was degraded with a half-life of 3.1 days in freshwater collected from the Ohio river 1 mile below discharge from a municipal treatment plant at 20 °C and pH 6.9(2).
Environmental Bioconcentration
An estimated BCF of 71 was calculated for trimethylhexadecylammonium chloride(SRC), using an estimated log Kow of 3.23(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.
Volatilization from Water/Soil
The Henry's Law constant for trimethylhexadecylammonium chloride is estimated as 2.9X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trimethylhexadecylammonium chloride is expected to be essentially nonvolatile from water surfaces(2). Trimethylhexadecylammonium chloride's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces will not occur(SRC). Trimethylhexadecylammonium chloride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-10 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts
ARQUAD 16-50 WAS AMONG MANY SURFACTANTS THAT WERE TESTED AND DID NOT INDUCE IN VITRO NEOPLASTIC TRANSFORMATIONS OF HAMSTER EMBRYO CELLS AND WERE NOT MUTAGENIC FOR SALMONELLA TYPHIMURIUM STRAINS TA100 AND TA98 EITHER IN THE PRESENCE OR IN THE ABSENCE OF RAT LIVER ENZYMES.
ALTHOUGH CETYLTRIMETHYLAMMONIUM CHLORIDE INHIBITED TOTAL GROWTH OF THE DIMORPHIC YEAST ENDOMYCOPSIS FIBULIGERA, THE CATIONIC SURFACTANTS INCR GROWTH OF THE YEAST-LIKE CELLS WHILE GREATLY DECREASING GROWTH OF THE FILAMENTOUS CELLS.
STIMULATION OF CHORDA TYMPANI NERVE IN RATS WITH CETYLTRIMETHYLAMMONIUM CHLORIDE INCR SPONTANEOUS DISCHARGES, WHEREAS TREATMENT WITH POLYOXYETHYLENE LAURYL ETHER HAD EITHER NO EFFECT OR CAUSED INHIBITION. PRETREATMENT OF THE TONGUE WITH THE DETERGENT REDUCED THE SUBSEQUENT GUSTATORY RESPONSE TO QUININE, TARTARIC ACID, SODIUM CHLORIDE, AND SUCROSE.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of trimethylhexadecylammonium chloride with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Trimethylhexadecylammonium chloride is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).
Probable Routes of Human Exposure
NIOSH (NOES Survey 1981-1983) has statistically estimated that 16,226 workers (13,148 of these are female) are potentially exposed to trimethylhexadecylammonium chloride in the US(1). Occupational exposure to trimethylhexadecylammonium chloride may occur through dermal contact with this compound at workplaces where trimethylhexadecylammonium chloride is produced or used(SRC). The general population may be exposed to trimethylhexadecylammonium chloride due to the use of consumer products containing trimethylhexadecylammonium chloride(SRC).
Environmental Fate/Exposure Summary
Trimethylhexadecylammonium chloride's production and use as a coagulant (antibiotic production); conditioning agent (hair products); antistatic agent (textile spin finishes); and softening agent (textile finishes) may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 2.8X10-10 mm Hg at 25 °C indicates trimethylhexadecylammonium chloride will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase trimethylhexadecylammonium chloride will be removed from the atmosphere by wet and dry deposition. If released to soil, trimethylhexadecylammonium chloride is expected to have no mobility based upon an estimated Koc of 2.2X10+5. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole. Trimethylhexadecylammonium chloride will not volatilize from dry soil surfaces based upon its estimated vapor pressure. If released into water, trimethylhexadecylammonium chloride is expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. 10-20 ppm trimethylhexadecylammonium chloride was degraded with a half-life of 3.1 days in freshwater at 20 °C and pH 6.9. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 71 suggests the potential for bioconcentration in aquatic organisms is moderate. Occupational exposure to trimethylhexadecylammonium chloride may occur through dermal contact with this compound at workplaces where trimethylhexadecylammonium chloride is produced or used. The general population may be exposed due to the use of consumer products containing this compound. (SRC)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
CIR ingredient: Cetrimonium Chloride
Available as a 25% aqueous solution and 50% solution in isopropyl alcohol and water for use in antifungal formulations and hair conditioners; Also used as a disinfectant/germicide, cationic detergent, fermentation aid, dispersant, coagulant for antibiotic production, and antistatic and softening agent for textile finishes; [HSDB]
Using Disinfectants or Biocides [Category: Clean]
USED IN ANTIFUNGAL FORMULATION; IN HAIR CONDITIONER FORMULATION; DISINFECTANT; CATIONIC DETERGENT
SOFTENER IN HAIR TREATMENTS, EG, CREME RINSES
FERMENTATION AID
U.S. Production
2023: 1,000,000 - <5,000,000 lb
(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS
(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS
(1993) 1,420 Kg
Methods of Manufacturing
PROBABLY BY REACTION OF N-HEXADECYLAMINE WITH METHYL CHLORIDE IN THE PRESENCE OF SODIUM HYDROXIDE; REACTION OF N-HEXADECYLCHLORIDE WITH TRIMETHYLAMINE
n-Hexadecylamine + methyl chloride (quaternisation)
Trimethylamine + cetyl chloride (quaternisation)
Formulations/Preparations
25% SOLN IN WATER; 50% SOLN IN MIXT OF ISOPROPYL ALCOHOL AND WATER... /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/
COMPD CONTAINING A QUATERNARY NH4+ SALT SUCH AS ARQUAD 16/50 AND GREATER THAN 10% OF AN AMPHIPHILIC COMPD SUCH AS CIRRASOL STERILIZE DISPERSIONS OF A SOLID, WATER INSOL FUNGICIDE SUCH AS CAPTAN AN CAPTAFOL IN A SOLN OF A FUNGICIDAL PYRIMIDINE SALT SUCH AS ETHIRIMOL @ A PH 1-1.5.
Available as a 25% or 50% soluble in water
Household Products
Cosmetics product ingredient: Cetrimonium chloride
Information on 368 consumer products that contain Cetrimonium chloride in the following categories is provided:
General Manufacturing Information
Paint and Coating Manufacturing
1-Hexadecanaminium, N,N,N-trimethyl-, chloride (1:1): ACTIVE
THE PROPERTIES AND USES OF QUATERNARY AMMONIUM COMPD IN COSMETICS, AND ESP IN PRODUCTS FOR THE HAIR, ARE DISCUSSED.
Related reactions
Linked notes
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