Methods of making organic compounds by metathesis

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;
• L2 and L3 are independently neutral electron donor ligands;
• n is 0 or 1;
• m is 0, 1, or 2;
• X1 and X2 are independently anionic ligands;
• R1 and R2 are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups;
• X and Y are independently heteroatoms selected from N, O, S, and P;
• p and q are independently 0 or 1;
• Q1, Q2, Q3, and Q4 are independently linkers selected from the group consisting of hydrocarbylenes and substituted heteroatom-containing hydrocarbylenes;
• w, x, y, and z are independently zero or 1;
• and
• R3, R3A, R4, and R4A are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl.