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
Show more names
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
- Formal charge
- 0
- Complexity
- 145
Experimental & physicochemical properties
Cosmetics
Cosmetic ingredients (Stearamine) -> CIR (Cosmetic Ingredient Review)
Personal care product
Antistatic
Density
0.8618 at 68 °F (NTP, 1992) - Less dense than water; will float
0.8618 @ 20 °C/4 °C
0.86 g/cm³
Solubility
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
Flash Point
300 °F (NTP, 1992)
148 °C c.c.
Boiling Point
660 °F at 760 mmHg (NTP, 1992)
346.8 °C @ 760 mm Hg
346.8 °C
Melting Point
120 to 126 °F (NTP, 1992)
52.9 °C
49 - 52 °C
52.9 °C
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
- storage temp.
- 30 °C · Store below +30°C.
- form
- Prills
- pka
- 10.6 · 10.6(at 25℃)
- color
- White
- Water Solubility
- practically insoluble
- FreezingPoint
- 53.1 ℃ · 53.1℃
- BRN
- 636111 · 636111
- Henry's Law Constant
- 1 · 1.0×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
- Cosmetics Ingredients Functions
- ANTISTATIC
- InChI
- 1S/C18H39N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-19H2,1H3
- InChIKey
- REYJJPSVUYRZGE-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCCCCCCCCCCN
- LogP
- 4.33 at · 4.33 at 25℃
- CAS DataBase Reference
- 124 · 124-30-1(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- OCTADECYLAMINE
- FDA 21 CFR
- 173.31 · 173.310
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 58 UNY7O · FFV58UNY7O
- NIST Chemistry Reference
- 1 · 1-Octadecanamine(124-30-1)
- EPA Substance Registry System
- Stearamine (124-30-1)
- UNSPSC Code
- 12352116 · 12352116
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 5 · GHS05,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 304 · H304-H315-H318-H373-H410
- Precautionary statements
- 273 · P273-P280-P301+P310-P305+P351+P338+P310-P331-P501
- target organs
- Liver,Gastrointestinal tract,Immune system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,N,Xn
- Risk Statements
- 36 · 36/37/38-41-38-65-50/53-48/22
- Safety Statements
- 26 · 26-36-37/39-28B-62-61-60-36/37/39
- RIDADR
- 3259 · 3259
- WGK Germany
- 2 · 2
- RTECS
- 4150000 · RG4150000
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29211980 · 29211980
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Skin Irrit. 2STOT RE 2
- Hazardous Substances Data
- 124 · 124-30-1(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2395 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
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
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
Fire Hazards
This compound is combustible. (NTP, 1992)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary
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]
Reactivity Profile
OCTADECYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Hazard Classes and Categories
Acute Tox. 4 (49.3%)
Aspiration hazard - category 1
Skin corrosion/irritation - Category 2
Serious eye damage/eye irritation - Category 1
Asp. Tox. 1
Safety & protection
Fire Fighting
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
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
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.
Nonfire Spill Response
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
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.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.
Toxicology
Environmental Fate
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).
Toxicity Summary
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
Cough. Sore throat.
Redness. Pain.
Redness. Pain.
Soil Adsorption/Mobility
The Koc of octadecylamine is estimated as approximately 3.198X10+5(SRC), using an estimated log Kow of 7.7(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that octadecylamine is expected to be immobile in soil(SRC).
Human Toxicity Excerpts
SAID TO BE PRIMARY SKIN SENSITIZER.
The effects of non-drug-containing liposomes of different compositions and sizes on the proliferation of nine cancer-derived and one normal cultured human cell lines were determined. Stearylamine- and cardiolipin-containing liposomes were toxic (ID50) at 200 uM liposomal lipid concentrations or less ...
Environmental Bioconcentration
An estimated log BCF of 5.6 was calculated for octadecylamine(SRC), using an estimated log Kow of 7.7(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
The Henry's Law constant for octadecylamine is estimated as 9.4X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(1). This Henry's Law constant indicates that the neutral form of octadecylamine is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 167 hours(SRC). A pKa of 10.65(3) indicates octadecylamine will exist predominately in the protonated form at environmental pHs and therefore volatilization from water and moist soil surfaces is not expected to be an important fate process(SRC). Octadecylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.4X10-5 mm Hg at 25 °C(4).
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- RG4150000
- ridadr
- 3259
- hs_code
- 29211980
- Toxicity
- LD50 orally in Rabbit: 2395 mg/kg
- risk_code
- 36/37/38-41-38-65-50/53-48/22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS08,GHS09
- hazard_code
- Xi,N,Xn
- safety_code
- 26-36-37/39-28B-62-61-60-36/37/39
- hazard_class
- 8
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Liver,Gastrointestinal tract,Immune system
- Hazard statements
- H304-H315-H318-H373-H410
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Skin Irrit. 2STOT RE 2
- Precautionary statements
- P273-P280-P301+P310-P305+P351+P338+P310-P331-P501
- Hazardous Substances Data
- 124-30-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
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
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
General Manufacturing Information
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: An 18-carbon primary aliphatic amine.
Related reactions
Linked notes
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