Octadecylamine

Base Information

• Chemical Name: Octadecylamine
• CAS No.: 124-30-1
• Deprecated CAS: 1341-47-5,8038-60-6,258339-97-8,457883-16-8,1533423-47-0,2031250-41-4,52953-83-0,54385-93-2,54693-04-8,56572-34-0,8031-10-5,8035-05-0,8035-06-1,2407463-37-8,258339-97-8,457883-16-8,8038-60-6
• Molecular Formula: C18H39N
• Molecular Weight: 269.514
• Hs Code.: 29211980
• European Community (EC) Number: 204-695-3,262-976-6
• ICSC Number: 1365
• NSC Number: 9857
• UN Number: 1759
• UNII: FFV58UNY7O
• DSSTox Substance ID: DTXSID1025801
• Nikkaji Number: J10.159A
• Wikidata: Q2013790
• Metabolomics Workbench ID: 43924
• ChEMBL ID: CHEMBL55860
• Mol file: 124-30-1.mol

Synonyms:1-octadecanamine, hydrochloride;1-octadecanamine, hydrochloride (1:1);1-octadecylamine;octadecyl ammonium chloride;octadecylamine;octadecylamine hydrochloride;stearamine;stearyl amine;stearylamine;stearylamine hydrochloride;stearylammonium chloride

Chemical Property of Octadecylamine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 10 mm Hg ( 72 °C)
• Melting Point: 50-60 °C
• Refractive Index: 1.4522
• Boiling Point: 348.875 °C at 760 mmHg
• PKA: 10.6(at 25℃)
• Flash Point: 154.077 °C
• PSA: 26.02000
• Density: 0.818 g/cm³
• LogP: 6.90690
• Storage Temp.: Store below +30°C.
• Water Solubility.: practically insoluble
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 16
• Exact Mass: 269.308250248
• Heavy Atom Count: 19
• Complexity: 145
• Transport DOT Label: Corrosive

Purity/Quality:

98% , ^*data from raw suppliers

Octadecylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-41-38-65-50/53-48/22
• Safety Statements: 26-36-37/39-28B-62-61-60-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aliphatic
• Canonical SMILES: CCCCCCCCCCCCCCCCCCN
• 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.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• 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. 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. 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. Octadecylamine (ODA) is used:To induce hydrophobicity in nanodiamond (ND) powders.In the surface modification of graphite and fullerenes.As a dual source of carbon and nitrogen in the synthesis of N-doped carbon nanotubes (CNTs).To synthesize a single-chain cationic surfactant, bis(amidoethylcarbamoylethyl) octadecylamine.
• Production method: It can be obtained from stearic acid via ammoniation and hydrogenation. Send stearic acid and ammonia continuously and quantitatively into the liquid phase reaction tower for ammoniation at 350 ℃ to generate octadecane nitrile. After washing with water and refinement, it was sent to the autoclave and was subject to hydrogenation reaction under 130 ℃ and the pressure of about 3.5MPa with the nickel catalyst for generation of Octadecanamine. The hydrogenated product was subject to precipitation for removing the catalyst to derive the final products. During laboratory preparation, the octadecane nitrile and anhydrous ethanol are subject to boiling under reflux and further put into sodium metal for reaction. Pour the reaction mixture into the dilute hydrochloric acid with cooling obtaining the Octadecanamine hydrochloride. Further treat with 20% sodium hydroxide solution treated with 20% sodium hydroxide solution can produce Octadecanamine. The yield is 85%. Fixed consumption amount of material: stearic acid: 1165kg/t, ammonia 151kg/t, hydrogen gas: 211m3, nickel catalyst: 6kg/t.

Technology Process of Octadecylamine

There total 36 articles about Octadecylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.2%

stearonitrile (638-65-3) → 1-aminooctadecane (124-30-1)

Guidance literature:

With sodium hydroxide; hydrogen; nickel; In water; at 135 ℃; for 3h; under 14251.4 Torr;

Reference yield: 95.0%

2-octadecylisoindoline-1,3-dione (20332-12-1) → 1-aminooctadecane (124-30-1)

Guidance literature:

With hydrazine hydrate; In methanol; at 95 ℃; for 1h;

DOI:10.1021/acs.joc.8b00161

Reference yield: 93.0%

N-trityloctadecan-1-amine (1262670-57-4) → 1-aminooctadecane (124-30-1)

Guidance literature:

With ammonium cerium (IV) nitrate; water; acetic acid; In dichloromethane; at 20 ℃; for 40h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.10.118

upstream raw materials:

1-chlorooctadecane

Methyl stearate

Dioctadecylamine

stearamide

Downstream raw materials:

N-octadecylpyrrolidone

(N-octadecyl)maleamic acid

N-octadecylacetamide

2,5-dichloro-3,6-bis-octadecylamino-[1,4]benzoquinone

Refernces

• 1、 -. "Non-Cryogenic, Ammonia-Free Reduction of Aryl Compounds". . . Retrieved 2022/03/31.
• 2、 Adam, Rosa,Alberico, Elisabetta,Baumann, Wolfgang,Drexler, Hans-Joachim,Jackstell, Ralf,Junge, Henrik,Beller, Matthias. "NNP-Type Pincer Imidazolylphosphine Ruthenium Complexes: Efficient Base-Free Hydrogenation of Aromatic and Aliphatic Nitriles under Mild Conditions". . p. 4991 - 5002. Retrieved 2016/04/05.