Methods of making organic compounds by metathesis and hydrocyanation

A method of making an organic compound, the method comprising:

• (a) providing a starting composition comprising an unsaturated glyceride represented by the formula:
• CH2A-CHB—CH2C
• wherein -A, —B, and —C are independently selected from the group consisting of:
• —OH;
• —O(O)C—(CH2)n2-[—CH═CH—(CH2)n3-]x—(CH2)n1—CH3;
• and
• —O(O)C—R′;
• with the proviso that at least one of -A, —B, or —C is
• —O(O)C—(CH2)n2—[—CH═CH—(CH2)n3-]x—(CH2)n1—CH3
• 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.