Patent ID: 9120742
Filing Date: 2015-09-01
Classification: B01J,C07C,C07F

Abstract:
1. A method of making a dicarboxylic acid alkene, dicarboxylate ester alkene, or dicarboxylate salt alkene, the method comprising the steps of: (a) providing a starting composition comprising one or more unsaturated fatty acids, unsaturated fatty esters, or unsaturated fatty acid salts, which comprise a residue selected from the group consisting of —C(O)—(CH2)7CH═CH—(CH2)7-CH3, —C(O)—(CH2)7CH═CH—CH2-CH═CH—(CH2)4-CH3, and —C(O)—(CH2)7CH═CH—CH2-CH═CH—CH2-CH═CH—CH2-CH3; (b) cross-metathesizing the composition of step (a) with 1-butene in the presence of a first metathesis catalyst, to form cross-metathesis products comprising: (i) one or more olefins having a terminal carbon-carbon double bond; and (ii) one or more acid-, ester-, or carboxylate salt-functionalized alkenes comprising a —C(O)—(CH2)7-CH═CH—CH2-CH3 residue; (c) separating at least a portion of one or more of the acid-, ester-, or carboxylate salt-functionalized alkenes of step (b) from the one or more olefins of step (b); and (d) self-metathesizing the separated acid-, ester-, or carboxylate salt-functionalized alkenes of step (c) in the presence of a second metathesis catalyst to form a composition comprising: (i) one or more dicarboxylic acid alkenes, dicarboxylate ester alkenes, or dicarboxylate salt alkenes, which comprise a —C(O)—(CH2)7-CH═CH—(CH2)7-C(O)— residue, and (ii) 3-hexene; wherein the first metathesis catalyst is a 2nd Generation Grubbs-type catalyst having the structure of formula (V): wherein: M is a Group 8 transition metal; L n is 0 or 1; m is 0, 1, or 2; X R X and Y are independently heteroatoms selected from N, O, S, and P; p and q are independently 0 or 1; Q w, x, y, and z are independently zero or 1; and R