Oleonitrile

Base Information

• Chemical Name: Oleonitrile
• CAS No.: 112-91-4
• Molecular Formula: C18H33 N
• Molecular Weight: 263.467
• Hs Code.: 2926909090
• European Community (EC) Number: 204-016-0
• UNII: 59F4912BUE
• DSSTox Substance ID: DTXSID3026934
• Nikkaji Number: J193.607G
• Wikidata: Q27261698
• Mol file: 112-91-4.mol

Synonyms:Oleonitrile;(Z)-octadec-9-enenitrile;112-91-4;9-Octadecenenitrile, (9Z)-;Oleic acid nitrile;Oleoylnitrile;Oleic nitrile;Oleylonitrile;Oleyl nitrile;(Z)-9-OCTADECENENITRILE;9-Octadecenenitrile, (Z)-;Olsaeurenitril;Olsaeurenitril [German];(9Z)-octadec-9-enenitrile;HSDB 5580;EINECS 204-016-0;BRN 1102081;UNII-59F4912BUE;9-Octadecenoic acid (cis), nitrile (cis);59F4912BUE;EC 204-016-0;4-02-00-01668 (Beilstein Handbook Reference);olenitrile;Oleanitrile;cis-9-octadecenenitrile;cis-octadec-9-enenitrile;SCHEMBL1958159;DTXSID3026934;C18H33N;CHEBI:133637;C18-H33-N;(Z)-9-OCTADECENENITRILE [HSDB];LS-97739;Q27261698

Chemical Property of Oleonitrile

Chemical Property:

• Vapor Pressure: 3.76E-06mmHg at 25°C
• Melting Point: -1°C
• Refractive Index: 1.4566
• Boiling Point: 385.6°Cat760mmHg
• Flash Point: 191.1°C
• PSA: 23.79000
• Density: 0.842g/cm³
• LogP: 6.54748
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 14
• Exact Mass: 263.261300057
• Heavy Atom Count: 19
• Complexity: 233

Purity/Quality:

99.9% ^*data from raw suppliers

OLEONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC#N
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC#N
• Uses: 9-Octadecenenitrile is used in the production of biofuel and biochar by thermal pyrolysis of linseed seed. It is also used as a fatty nitrile solvent for agricultural formulations.

Technology Process of Oleonitrile

There total 13 articles about Oleonitrile 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: 95.0%

cis-9-octadecenoamide (301-02-0,3322-62-1,94554-98-0) → cis-9-octadecenenitrile (112-91-4)

Guidance literature:

With phosphorus pentoxide; at 150 ℃; for 8h;

DOI:10.1016/S0040-4020(01)88524-0

Reference yield: 95.0%

methanesulfonyl cyanide (24225-08-9) + (Z)-Octadec-9-enoic acid 2-thioxo-2H-pyridin-1-yl ester (119520-40-0) → cis-9-octadecenenitrile (112-91-4)

Guidance literature:

In dichloromethane; at 0 ℃; Irradiation;

DOI:10.1016/S0040-4039(00)92696-0

Reference yield: 95.0%

P-toluenesulfonyl cyanide (19158-51-1) + (Z)-Octadec-9-enoic acid 2-thioxo-2H-pyridin-1-yl ester (119520-40-0) → cis-9-octadecenenitrile (112-91-4)

Guidance literature:

In dichloromethane; at 0 ℃; Irradiation;

DOI:10.1016/S0040-4020(01)88524-0

upstream raw materials:

cis-9-octadecenoamide

cis-Octadecenoic acid

Methyl oleate

urea

Downstream raw materials:

cis-octadec-9-enethiol

(Z)-undec-2-enenitrile

(E)-undec-2-enenitrile

1-Decene

Refernces

• 1、 Witt, Timo,Stempfle, Florian,Roesle, Philipp,H?ussler, Manuel,Mecking, Stefan. "Unsymmetrical α,ω-Difunctionalized Long-Chain Compounds via Full Molecular Incorporation of Fatty Acids". . p. 4519 - 4529. Retrieved 2015.
• 2、 Lu, Guo-Ping,Li, Xinxin,Zhong, Lixiang,Li, Shuzhou,Chen, Fei. "Ru@UiO-66(Ce) catalyzed acceptorless dehydrogenation of primary amines to nitriles: The roles of Lewis acid-base pairs in the reaction". supporting information. p. 5386 - 5393. Retrieved 2019/10/11.