Patent ID: 8895771

Claim:
A method of making an organic compound, the method comprising: (a) providing a starting composition comprising an unsaturated glyceride represented by the formula: CH 2 A-CHB—CH 2 C wherein -A, —B, and —C are independently selected from the group consisting of: —OH; —O(O)C—(CH 2 ) n2 -[—CH═CH—(CH 2 ) n3 -] x —(CH 2 ) n1 —CH 3 ; and —O(O)C—R′; with the proviso that at least one of -A, —B, or —C is —O(O)C—(CH 2 ) n2 —[—CH═CH—(CH 2 ) n3 -] x —(CH 2 ) n1 —CH 3 and wherein R′ is a straight or branched chain alkyl or alkenyl group; n1 is an integer equal to or greater than 0; n2 is an integer equal to or greater than 0; n3 is an integer equal to or greater than 0; and x is an integer equal to or greater than 1; (b) cross-metathesizing the unsaturated glyceride with a short-chain olefin in the presence of a metathesis catalyst to form cross-metathesis products comprising: (i) one or more olefin compounds; and (ii) one or more metathesized unsaturated glycerides, wherein the short-chain olefin is an α-olefin selected from the group consisting of 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, and combinations thereof; (c) separating at least a portion of the one or more metathesized unsaturated glycerides from the cross-metathesis products; (d) isomerizing the separated one or more metathesized unsaturated glycerides to form one or more isomerized separated metathesized unsaturated glycerides having a terminal olefin; and (e) catalytically modifying the carbon-carbon double bond of the one or more separated metathesized unsaturated glycerides or the one or more isomerized separated metathesized unsaturated glycerides by hydrocyanation to form a hydrocyanated glyceride.