N-Hexadecyltrimethylammonium chloride structure

3D Mol Similar

N-Hexadecyltrimethylammonium chloride

Iupac Name：hexadecyl(trimethyl)azanium;chloride

CAS No.: 112-02-7

Molecular Weight：319.99648

Modify Date.: 2022-11-29 09:05

Introduction: Colorless to pale yellow liquid with an odor of rubbing alcohol. Floats or sinks in water. View more+

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1. Names and Identifiers

1.1 Name: N-Hexadecyltrimethylammonium chloride
1.2 Synonyms: (1-Hexadecyl)trimethylammonium chloride 1631(Cl) barquatct29 C16-alkyltrimethylammonium chloride Hexadecyltrimethylammonium chloride (CTAC) MFCD00011773

1.3 CAS No.: 112-02-7

1.4 CID: 8154

1.5 EINECS(EC#): 203-928-6

1.6 Molecular Formula: C19H42ClN (isomer)

1.7 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

1.8 InChkey: WOWHHFRSBJGXCM-UHFFFAOYSA-M

1.9 Canonical Smiles: CCCCCCCCCCCCCCCC[N+](C)(C)C.[Cl-]

1.10 Isomers Smiles: CCCCCCCCCCCCCCCC[N+](C)(C)C.[Cl-]

2. Properties

2.1 Density: 0.9 at 77 °F (approx.) (USCG, 1999)

2.1 Melting point: 232-234℃

2.1 Boiling point: 100 C

2.1 Refractive index: n20/D 1.3778

2.1 Flash Point: °C

2.1 Precise Quality: 319.30100

2.1 PSA: 0.00000

2.1 logP: 3.17790

2.1 Appearance: White Amorphous Powder

2.2 Storage: Ambient temperatures.

2.3 Autoignition Temperature: 750 °F (USCG, 1999)

2.4 Chemical Properties: Liquid

2.5 Color/Form: White

2.6 Decomposition: When heated to decomposition it emits very toxic fumes of /hydrogen chloride and nitrogen oxides/.

2.7 PH: pH(50g/l, 25℃) : 6.0～8.5

2.8 Water Solubility: Water solubility: 440 mg/l at 30 deg C

2.9 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.10 StorageTemp: Store in a tightly closed container. Keep under a nitrogen blanket. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.

3. Use and Manufacturing

3.1 Definition: ChEBI: The organic chloride salt of cetyltrimethylammonium.

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

3.3 Methods of Manufacturing: Put 250 kg of hexadecane dimethylamine into the reactor.?Add 250L petroleum ether to dissolve.?Introduce 47 kg of methyl chloride.?Stir to heat up under sealed conditions and azeotrope at 80 °C for 1 h.?After cooling, lowering the temperature and lowering the pressure, a mixed solvent of ethanol and ethyl ester is added at normal pressure for recrystallization to obtain a finished product.

3.4 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.] N-Hexadecyltrimethylammonium chloride Preparation Products And Raw materials Preparation Products

3.5 Usage: Barquat(R) CT-29 is a quaternary ammonium based surfactant that finds uses in broad number of industrial cleaning products. Product Data Sheet

4. Safety and Handling

4.1 Symbol: GHS05, GHS09

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R22;R37/38;R41;R50/53

4.1 Safety Statements: S26;S37/39;S60;S61

4.1 Packing Group: I; II; III

4.1 Octanol/Water Partition Coefficient: log Kow= 3.23

4.2 Other Preventative 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.

4.3 Hazard Class: 8

4.3 Hazard Declaration: H315-H318-H400

4.3 DisposalMethods: 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.

4.4 RIDADR: UN 3077

4.4 Fire Fighting Procedures: ...DRY CHEM, /ALCOHOL/ FOAM, OR CARBON DIOXIDE. WATER MAY BE INEFFECTIVE ON FIRE. COOL EXPOSED CONTAINERS WITH WATER. /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/

4.5 Caution Statement: P280-P305 + P351 + P338 + P310

4.5 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

4.6 WGK Germany: 3

4.6 RTECS: ML9145000

4.6 Protective Equipment and Clothing: VAPOR IRRITATING TO EYES, NOSE AND THROAT.
VAPOR IRRITATING TO EYES, NOSE AND THROAT. HARMFUL IF INHALED. LIQUID IRRITATING TO SKIN AND EYES. HARMFUL IF SWALLOWED. /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/

4.7 Skin, Eye, and Respiratory Irritations: VAPOR IRRITATING TO EYES, NOSE AND THROAT.
VAPOR IRRITATING TO EYES, NOSE AND THROAT. HARMFUL IF INHALED. LIQUID IRRITATING TO SKIN AND EYES. HARMFUL IF SWALLOWED. /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/

4.8 Safety: Hazard Codes:Xi,N,Xn
Risk Statements:38-41-50-50/53-37/38-22-43-36/37/38
38:Irritating to the skin
41:Risk of serious damage to eyes
50:Very Toxic to aquatic organisms
50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
37/38:Irritating to eyes, respiratory system and skin
22:Harmful if swallowed
43:May cause sensitization by skin contact
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-39-60-61-37/39-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
39:Wear eye/face protection
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
37/39:Wear suitable protective clothing, gloves and eye/face protection
36:Wear suitable protective clothing
RIDADR:UN 3082 9/PG 3
WGK Germany:3
HS Code:29239000

4.9 Specification: Liquid
usageEng:Barquat(R) CT-29 is a quaternary ammonium based surfactant that finds uses in broad number of industrial cleaning products. Product Data Sheet
Safety Statements:26-39-60-61-37/39-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
39:Wear eye/face protection
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
37/39:Wear suitable protective clothing, gloves and eye/face protection
36:Wear suitable protective clothing

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

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 3

Skin corrosion, Category 1C

Serious eye damage, Category 1

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H311 Toxic in contact with skin H314 Causes severe skin burns and eye damage H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

7. Synthesis Route

112-02-7Total: 3 Synthesis Route

143-27-1 71 Suppliers

112-02-7 310 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 69, p. 2096
Yield: null

74-87-3 71 Suppliers

112-69-6 86 Suppliers

112-02-7 310 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 69, p. 2096
Yield: null

4860-03-1 82 Suppliers

75-50-3 58 Suppliers

112-02-7 310 Suppliers

Literatures:
Journal of Physical Chemistry, , vol. 45, p. 954,958 Chemische Berichte, , vol. 73, p. 1007
Yield: null

8. Precursor and Product

precursor:

143-27-1

74-87-3

4860-03-1

112-69-6

75-50-3

product :

78-67-1

74784-26-2

342808-35-9

9. Other Information

9.0 Storage Conditions: Put 250 kg of hexadecane dimethylamine into the reactor.?Add 250L petroleum ether to dissolve.?Introduce 47 kg of methyl chloride.?Stir to heat up under sealed conditions and azeotrope at 80 °C for 1 h.?After cooling, lowering the temperature and lowering the pressure, a mixed solvent of ethanol and ethyl ester is added at normal pressure for recrystallization to obtain a finished product.

9.1 Experimental Properties: CLEAR TO PALE YELLOW LIQUID; RUBBING ALCOHOL ODOR /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/

9.2 Reactive Group: Non-Redox-Active Inorganic Compounds

9.3 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. Quaternary ammonium salts often serve as catalysts in reactions. They are incompatible with many strong oxidizers and reducing agents, such as metal hydrides, alkali/active metals, and organometallics.

9.4 Autoignition Temperature: 750 °F (USCG, 1999)|750 °F /ISOPROPYL ALCOHOL SOLN OF CETYLTRIMETHYLAMMONIUM CHLORIDE/

9.5 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.

9.6 Fire Hazards: Special Hazards of Combustion Products: Irritating fumes of hydrogen chloride may form in fires. Behavior in Fire: Solvent vapors are heavier than air and may travel to a source of ignition and flash back. (USCG, 1999)

9.7 Nonfire Spill Response: Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

9.8 Personal Protective Equipment: Goggles or face shield; rubber gloves (USCG, 1999)|GOGGLES OR FACE SHIELD; RUBBER GLOVES. /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/

9.9 Fire Fighting Procedures: ...DRY CHEM, /ALCOHOL/ FOAM, OR CARBON DIOXIDE. WATER MAY BE INEFFECTIVE ON FIRE. COOL EXPOSED CONTAINERS WITH WATER. /CETYLTRIMETHYLAMMONIUM CHLORIDE SOLN/

9.10 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.

9.11 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).

9.12 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).

9.13 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).

9.14 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.

9.15 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.

9.16 Volatilization: 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).

9.17 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).

9.18 Mesh: Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

9.19 First Aid: INGESTION: do NOT induce vomiting; drink large quanities of fluid and call a physician immediately. EYES: flush with water for at least 15 min. and call a physician. SKIN: flush with water. (USCG, 1999)

9.20 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.

9.21 Mesh Entry Terms: 1-hexadecyltrimethylammonium chloride

9.22 Production: 1,000,000 - 10,000,000 lb|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1993) 1,420 Kg

9.23 Formulations: 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

9.24 Manufacturing Info: All other chemical product and preparation manufacturing|1-Hexadecanaminium, N,N,N-trimethyl-, chloride (1:1): ACTIVE|Quaternary ammonium compounds, C14-18-alkyltrimethyl, chlorides: ACTIVE|THE PROPERTIES AND USES OF QUATERNARY AMMONIUM COMPD IN COSMETICS, AND ESP IN PRODUCTS FOR THE HAIR, ARE DISCUSSED.

9.25 Use Classification: Cosmetics -> Preservative

9.26 Usage: (1-Hexadecyl)trimethylammonium chloride is used as a topical antiseptic and surfactant. It is used in hair care formulations, cream rinse ingredient, hair conditioners and shampoos as a conditioning agent.

10. Computational chemical data

Molecular Weight: 319.99648g/mol
Molecular Formula: C₁₉H₄₂ClN
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 319.3005780
Monoisotopic Mass: 319.3005780
Complexity: 181
Rotatable Bond Count: 15
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 0
Heavy Atom Count: 21
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADcfB6AAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHAAAAAAACADBAAQCAAMAAAAAAAAAAAAAAAAAAAAAAAAIAAAAAAIAgAAEAAAAAAAAAAEQgIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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N-Hexadecyltrimethylammonium chloride