Octadecylamine

HCID 15793CAS 124-30-1

Basic information

Standard SMILES
CCCCCCCCCCCCCCCCCCN
InChIKey
REYJJPSVUYRZGE-UHFFFAOYSA-N
Molecular formula
C18H39N
Average molar mass
269.5 g/mol
Monoisotopic mass
269.30825025

Overview

Octadecylamine appears as a white solid. Insoluble in water and less dense than water. Hence floats on water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.

Names & identifiers

Preferred name
Octadecylamine
IUPAC
octadecan-1-amine
English name
Octadecanamine
Molecular formula
C18H39N
Molecular weight
269.51

Names & synonyms

OCTADECYLAMINEoctadecan-1-amine124-30-11-OctadecanamineStearylamineStearamine1-Octadecylamine1-Aminooctadecanen-OctadecylamineStearyl amineArmofilmn-Stearylamine
Show more names
OctadecyLA18EighteenaMineFENTAMINE A18
MonooctadecylamineArmeen 18DNissan amine ABOktadecylaminAlamine 7Alamine 7DNoram SHAdogenen 142

Database identifiers

CAS
124-30-1、61788-45-2
PubChem CID
15793
DTXSID
DTXSID1025801
ChEMBL
CHEMBL55860
ChEBI
CHEBI:63866
UNII
FFV58UNY7O
EC Number
204-695-3
Nikkaji
J10.159A

Properties

Computed structural properties

XLogP
8.5
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
16
Heavy atoms
19

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aliphatic
Cosmetics · 3 items

Cosmetic ingredients (Stearamine) -> CIR (Cosmetic Ingredient Review)

Personal care product

Antistatic

LogP7.7
Food AdditivesBOILER WATER ADDITIVE -> FDA Substance added to food
Density · 3 items

0.8618 at 68 °F (NTP, 1992) - Less dense than water; will float

0.8618 @ 20 °C/4 °C

0.86 g/cm³

Solubility · 3 items

less than 1 mg/mL at 72 °F (NTP, 1992)

Insol in water; sol in alcohol, ether, benzene; very sol in chloroform; miscible in acetone

Solubility in water: very poor

Physicochemical properties

Melting point
50 · 50-52 °C(lit.)
Boiling point
232 °C32 · 232 °C32 mm Hg(lit.)
Density
0.862 · 0.862
vapor pressure
10 mm · 10 mm Hg ( 72 °C)
refractive index
1.4522 · 1.4522
Flash point
300 °F · 300 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H304: May be fatal if swallowed and enters airways [Danger Aspiration hazard]

P260, P264, P264+P265, P273, P280, P301+P316, P302+P352, P305+P354+P338, P317, P319, P321, P331, P332+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.8% (7 of 907) of reports.

Danger

H302 (49.3%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 4 items

Chemical: 1-Octadecanamine

1-Octadecanamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Octadecanamine 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: 12-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14418

1-Octadecanamine: HSNO Approval: HSR001542 Approved with controls

Other Safety InformationIMAP assessments - 1-Octadecyl- and hydrogenated tallow alkyl- amines: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards · 2 items

This compound is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsACUTE/CHRONIC HAZARDS: Exposure to this compound may cause sensitization of the skin. (NTP, 1992)
Hazards Summary · 1 item

A skin, eye, and respiratory tract irritant; [ICSC] May cause skin sensitization; A primary skin irritant in animals; A 2-year feeding study of rats showed no adverse effects to food consumption, hematology, or histopathology at 500 ppm; Effects at 3000 ppm include anorexia and some histological changes to GI tract, mesenteric nodes, and liver; [HSDB] A moderate skin irritant in rabbits; [RTECS] A skin irritant that may cause serious eye injury; Not likely to induce skin sensitization; No evidence of mutagenicity; Not likely to have carcinogenic potential or reproductive toxicity; [ECHA] An irritant; Harmful if swallowed; [Alfa Aesar MSDS]

Safety & protection

Fire Fighting · 2 items

Fires involving this compound can be controlled with dry chemical, carbon dioxide or Halon extinguishers. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink.

First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from acids, acid anhydrides, acid chlorides and oxidants.
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

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.

Toxicology

InteractionsIF (3)H-METHOTREXATE IS COMPLETELY ENTRAPPED IN LIPOSOMES CONCN OF DRUG IN LIVER & SPLEEN INCR. IF DICETYL PHOSPHATE IN LIPOSOMES IS REPLACED BY STEARYLAMINE GREATER PROP OF LIPOSOMES IS TAKEN UP BY LIVER & SPLEEN.
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated log Koc value of 5.5(SRC), determined from an estimated log Kow of 7.7(2,SRC) and a regression-derived equation(3), indicates that octadecylamine is expected to be immobile in soil(SRC). A pKa value of 10.65(4) indicates that the protonated form will be the dominant species in moist soil surfaces and cationic molecules generally adsorb strongly to soils(SRC). Volatilization of octadecylamine from moist soil surfaces is not expected to be an important fate process since the protonated form is expected to be the dominant species based on the pKa value(4). Volatilization of octadecylamine from dry soil surfaces is not expected(SRC) based upon the estimated vapor pressure of 4.4X10-5 mm Hg at 25 °C(5). A 32% of theoretical BOD in an activated sludge inoculum was observed over a 15-day incubation period(6), suggesting that biodegradation may be rapid in the environment(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated log Koc value of 5.5(SRC), determined from an estimated log Kow of 7.7(2,SRC) and a regression-derived equation(3), indicates that octadecylamine is expected to adsorb to suspended solids and sediment in water(SRC). A pKa value of 10.65(4) indicates that the protonated form will be the dominant species in water and volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), an estimated log BCF of 5.6(3,SRC), from its estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). A 32% of theoretical BOD in an activated sludge inoculum was observed over a 15-day incubation period(6), suggesting that biodegradation may be rapid in the environment(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), octadecylamine, which has an estimated vapor pressure of 4.4X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase octadecylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hours(SRC) from its estimated rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC), determined from a structure estimation method(3). Particulate-phase octadecylamine will be removed from the atmosphere by wet and dry depostion(SRC).

Exposure RoutesThe substance can be absorbed into the body by ingestion.
Toxicity Summary · 2 items

The safety of Lauramine and Stearamine has not been documented and substantiated. The CIR Expert Panel cannot conclude whether these ingredients are safe for use in cosmetic products until the appropriate safety data have been obtained and evaluated.

The available data are insufficient to support safety

Signs and Symptoms · 3 items

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
RG4150000
ridadr
3259
hs_code
29211980

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Uses & manufacturing

Uses · 6 items

CIR ingredient: Stearamine

Used as a corrosion inhibitor (steam systems), mold releasing agent (manufacturing of battery cases), anti-caking and flotation agent, anti-stripping agent (asphalt emulsions for highways), and chemical intermediate; Also used for various applications in the petroleum industry; [HSDB] Used for metal extraction, refining, and processing of metals; [IUCLID]

Petroleum Production and Refining [Category: Industry]

ANTICORROSIVE AGENT

MOLD RELEASE AGENT IN MFR OF BATTERY CASES; CORROSION INHIBITOR IN STEAM PLANTS; CHEMICAL INTERMEDIATE FOR OCTADECYL ISOCYANATE; CHEMICAL INTERMEDIATE FOR OTHER SURFACE-ACTIVE AGENTS; ANTICAKING AGENT; FLOTATION AGENT; AGENT IN VARIOUS ASPECTS OF PETROLEUM INDUSTRY; ANTISTRIPPING AGENT IN ASPHALT EMULSIONS FOR HIGHWAYS

Surface protection against condensate corrosion in steam systems.

U.S. Production · 4 items

2023: 550,000 - <1,000,000 lb

(1972) 2.46X10+8 GRAMS

(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS

(1984) 1.11X10+9 g

Industry UsesEmulsifier
Methods of ManufacturingCATALYTIC HYDROGENATION OF STEARYL NITRILE
Use ClassificationCosmetics -> Antistatic
General Manufacturing Information · 3 items

All Other Chemical Product and Preparation Manufacturing

1-Octadecanamine: ACTIVE

EIGHTEEN CARBON STRAIGHT CHAIN AMINE SOMETIMES USED AS ANTICORROSIVE AGENT IN LIVE STEAM LINES.

Applications · 5 items

DescriptionOctadecylamine, also known as N-stearylamine or 1-aminooctadecane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Octadecylamine is a very strong basic compound (based on its pKa). An 18-carbon primary aliphatic amine.

UsesIt can be used as the intermediates of organic synthesis for the production of octadecyl quaternary ammonium salts and many kinds of additives such as cationic grease thickener, mineral flotation agents, pesticides and asphalt emulsifier, fabric antistatic agents, softeners, wetting agents and waterproofing agents, surfactants, biocides, color former of color photo and the corrosion inhibitor of the oil refining device. Putting the Octadecanamine in mixture with ethylene oxide in a molar ratio of 1: 2 for reaction at 150-190 ℃ can gives stearyl diethanolamine [10213-78-2] with a yield of 80%. Stearyl diethanolamine belongs to a non-ionic antistatic agent and can be applied to polypropylene, polystyrene and ABS resin.

UsesOctadecylamine is used in biological studies for the formation of ion pairing as alternative to improve encapsulation and stability and to reduce skin irritation of retinoic acid loaded in solid lipid nanoparticles.

UsesOctadecylamine is used to surface functionalize different carbon nanomaterials (graphene oxide, carbon nanotubes) for different applications which include thin film nanocomposite (TFN) nanofilteration and carbon fiber microelectrodes. It can be used for the preparation of butyrylcholinesterase/stearylamine films (Langmuir-Blodgett films) for use in enzymatic field effect transistor (ENFET) based biosensors. Octadecylamine also forms films which can be used in ion exachnge systems. It may also be used in the preparation of metal oxide nano crystals with controlled size and shape.

General DescriptionA white solid. Insoluble in water and less dense than water. Hence floats on water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东隆汇化工有限公司531-88613858 15562516958 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

Additional notes

DefinitionChEBI: An 18-carbon primary aliphatic amine.

Related reactions

158 records

Linked notes

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