Methods of making organic compounds by metathesis and hydrocyanation

摘要

The invention is directed to methods of making organic compounds by metathesis and hydrocyanation. The method of the invention may be used, for example, to make industrial important organic compounds such as diacids, diesters, acid-amines, acid-alcohols, acid-nitriles, ester-amines, ester-alcohols, and ester-nitriles.

主权项

1. 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; andx 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.