HuagongsheHuagongshe Chemistry Print Report · For research reference only
Octadecylamine
OCTADECYLAMINE · STEARYLAMINE · 1-Octadecanamine · N-OCTADECYLAMINE · OctadecyL · 1-OCTADECYLAMINE · A18 · Stearamine
Identifiers & Physical Properties
| CAS No. | 124-30-1 |
|---|---|
| Molecular formula | C18H39N |
| Average molar mass | 269.5 g/mol |
| Monoisotopic mass | 269.30825025 g/mol |
| SMILES | CCCCCCCCCCCCCCCCCCN |
| InChIKey | REYJJPSVUYRZGE-UHFFFAOYSA-N |
| PubChem CID | 15793 |
| ChEMBL | CHEMBL55860 |
| ChEBI | CHEBI:63866 |
| EC No. | 204-695-3 |
| DTXSID | DTXSID1025801 |
Chemical & Physical Properties
| XLogP | 8.5 |
|---|---|
| Topological polar surface area | 26 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 16 |
| Heavy atoms | 19 |
| Formal charge | 0 |
| Complexity | 145 |
| Chemical classes | Nitrogen Compounds -> Amines, Aliphatic |
| Cosmetics | Cosmetic ingredients (Stearamine) -> CIR (Cosmetic Ingredient Review)Personal care productAntistatic |
| LogP (partition coefficient) | 7.7 |
| Food additives | BOILER WATER ADDITIVE -> FDA Substance added to food |
| Density | 0.8618 at 68 °F (NTP, 1992) - Less dense than waterwill float0.8618 @ 20 °C/4 °C0.86 g/cm³0.862 |
| Solubility | less than 1 mg/mL at 72 °F (NTP, 1992)Insol in watersol in alcohol, ether, benzenevery sol in chloroformmiscible in acetoneSolubility in water: very poorpractically insoluble |
| Flash point | 300 °F (NTP, 1992)148 °C c.c. |
| Boiling point | 660 °F at 760 mmHg (NTP, 1992)346.8 °C @ 760 mm Hg232 °C32 mm Hg(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of nitroxides. |
| Melting point | 120 to 126 °F (NTP, 1992)52.9 °C49 - 52 °C50-52 °C(lit.) |
| Vapor density | 9.29 (NTP, 1992) - Heavier than airwill sink (Relative to Air) |
| Vapor pressure | 0.0000438 [mmHg]10 mm Hg ( 72 °C) |
| Refractive index | 1.4522 |
| Storage conditions | Store below +30°C. |
| Physical state | Prills |
| pKa (acidity coefficient) | 10.6(at 25℃) |
| Color | White |
| Freezing point | 53.1℃ |
| BRN | 636111 |
| Henry's law constant | 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 (partition coefficient) | 4.33 at 25℃ |
| CAS DataBase Reference | 124-30-1(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | OCTADECYLAMINE |
| FDA 21 CFR | 173.310 |
| EWG's Food Scores | 1-3 |
| FDA UNII | FFV58UNY7O |
| NIST Chemistry Reference | 1-Octadecanamine(124-30-1) |
| EPA Substance Registry System | Stearamine (124-30-1) |
| UNSPSC Code | 12352116 |
| NACRES | NA.23 |
| GHS pictogram | GHS05,GHS08,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H304-H315-H318-H373-H410 |
| GHS precautionary statements | P273-P280-P301+P310-P305+P351+P338+P310-P331-P501 |
| Target organs | Liver,Gastrointestinal tract,Immune system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi,N,Xn |
| Risk statements (R) | 36/37/38-41-38-65-50/53-48/22 |
| Safety statements (S) | 26-36-37/39-28B-62-61-60-36/37/39 |
| UN transport number | 3259 |
| Water hazard class (WGK) | 2 |
| RTECS number | RG4150000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Skin Irrit. 2STOT RE 2 |
| Packing group | III |
| Customs code | 29211980 |
| Storage class | 11 - Combustible Solids |
| Hazardous substances data | 124-30-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 2395 mg/kg |
| REACH registrations | Active |
| 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) |
Safety & Regulations
| GHS classification | DangerH304: 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.H302 (49.3%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatory information | Chemical: 1-Octadecanamine1-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/144181-Octadecanamine: HSNO Approval: HSR001542 Approved with controls |
| Other safety information | IMAP assessments - 1-Octadecyl- and hydrogenated tallow alkyl- amines: Human health tier II assessment |
| DOT label | Corrosive |
| Fire hazards | This compound is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Health hazards | ACUTE/CHRONIC HAZARDS: Exposure to this compound may cause sensitization of the skin. (NTP, 1992) |
| Hazards summary | A skin, eye, and respiratory tract irritant[ICSC] May cause skin sensitizationA primary skin irritant in animalsA 2-year feeding study of rats showed no adverse effects to food consumption, hematology, or histopathology at 500 ppmEffects 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 injuryNot likely to induce skin sensitizationNo evidence of mutagenicityNot likely to have carcinogenic potential or reproductive toxicity[ECHA] An irritantHarmful if swallowed[Alfa Aesar MSDS] |
| Reactive group | Amines, Phosphines, and Pyridines |
| 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. |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including nitrogen oxides. The solution in water is a weak base. Reacts with acids, acid anhydrides, acid chlorides and oxidants. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (49.3%)Aspiration hazard - category 1Skin corrosion/irritation - Category 2Serious eye damage/eye irritation - Category 1Asp. Tox. 1 |
| 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. |
| Safe storage | Separated from acids, acid anhydrides, acid chlorides and oxidants. |
| 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C. |
| Skin Prevention | Protective gloves. |
| Interactions | IF (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 | 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 routes | The substance can be absorbed into the body by ingestion. |
| 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. |
| ICSC Environmental Data | Environmental effects from the substance have not been investigated adequately. |
| 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 ... |
| Artificial Pollution Sources | Octadecylamine's production and use as a corrosion protection agent in steam plants(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | A 32& of theoretical BOD using an activated sludge inoculum was observed for octadecylamine over a 15-day incubation period(1), suggesting that biodegradation may be rapid in the environment(SRC). |
| 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). |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | RG4150000 |
| UN transport number | 3259 |
| Customs code | 29211980 |
| Toxicity | LD50 orally in Rabbit: 2395 mg/kg |
| Risk statements (R) | 36/37/38-41-38-65-50/53-48/22 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS08,GHS09 |
| Hazard symbols | Xi,N,Xn |
| Safety statements (S) | 26-36-37/39-28B-62-61-60-36/37/39 |
| Hazard class | 8Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Skin Irrit. 2STOT RE 2 |
| Storage class | 11 - Combustible Solids |
| Packing group | III |
| Target organs | Liver,Gastrointestinal tract,Immune system |
| GHS 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 |
| GHS precautionary statements | P273-P280-P301+P310-P305+P351+P338+P310-P331-P501 |
| Hazardous substances data | 124-30-1(Hazardous Substances Data) |
Applications & Uses
Description
Octadecylamine, 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.
Uses
It 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.
Uses
Octadecylamine 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.
Uses
Octadecylamine 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 Description
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.