Acrylonitrile → Oleic Acid

HRID 1506726Notes

Reaction equation

C(#N)C=C.[C:5]([OH:16])(=[O:15])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14].[C:17]([O:28][CH3:29])(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26]>>[C:5]([OH:16])(=[O:15])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[C:17]([O:28][CH3:29])(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Reactant 3

HCID 7855Acrylonitrile

HCID 617439-Decenoic acid

HCID 1778877Methyl 9-decenoate

Product 2

HCID 445639Oleic Acid

HCID 5364509Methyl Oleate

Procedure

The cross metathesis reaction of acrylonitrile is preferably carried out with a compound chosen from 9-decenoic acid or methyl 9-decenoate, which are obtained from the ethenolysis of oleic acid or of methyl oleate, or of a triglyceride containing oleic acid; 10-undecenoic acid or methyl 10-undecenoate, which are obtained from the cracking of ricinoleic acid or from methyl ricinoleate, oleic acid, or methyl oleate; 9-octadecenedioic acid or methyl 9-octadecenedioate, which are obtained from homometathesis or from the fermentation of oleic acid, erucic acid, and methyl erucate; 12-tridecenoic acid or methyl 12-tridecenoate, which are obtained from the thermal cracking of lesquerolic acid; 13-tetradecenoic acid or methyl 13-tetradecenoate, which are obtained from the ethenolysis of erucic acid, lesquerolic acid and methyl lesquerolate, gondoic acid or methyl gondoate; 11-dodecenoic acid or methyl 11-dodecenoate, which are obtained from the ethenolysis of lesquerolic acid or of gondoic acid.

Sources & evidence

ORD record: ord-8249d626fefd4aeb81b28ff377311801
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221745B2

Reaction notes

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