Methods and Systems for Making Thiol Compounds from Terminal Olefinic Compounds

A method of producing a thiol ester composition comprising thiol ester molecules, the thiol ester molecules having ester linkages comprising a residue of a polyol and carboxylic acid residues having at least 4 carbon atoms and a thiol group located on a terminal carbon atom or a carbon atom adjacent to the terminal carbon atom, the method comprising:

• a) contacting ethylene and a natural source oil with a metathesis catalyst composition;
• b) forming unsaturated ester molecules having terminal carbon-carbon double bonds at metathesis conditions capable of forming the unsaturated ester molecules having terminal carbon-carbon double bonds;
• c) contacting the unsaturated ester molecules having terminal carbon-carbon double bonds and hydrogen sulfide;
• and
• d) forming the thiol ester composition comprising the thiol ester molecules at conditions capable of forming the thiol ester molecules;
• wherein the average ratio of carboxylic acid residues having a thiol group located on a terminal carbon atom or a carbon atom adjacent to the terminal carbon atom to hydroxyl groups of the polyol of the residue of the polyol is greater than 0.70:1.

A method of producing a thiol ester composition comprising thiol ester molecules, the method comprising:

• a) contacting ethylene and a natural source oil with a metathesis catalyst composition;
• b) forming unsaturated esters molecules having terminal carbon-carbon double bonds at metathesis conditions capable of forming the unsaturated ester molecules having terminal carbon-carbon double bonds;
• c) contacting the unsaturated ester molecules having terminal carbon-carbon double bonds and an oxygen containing compound;
• d) forming epoxide ester molecules having terminal epoxide groups at conditions capable of forming epoxide ester molecules having terminal epoxide groups;
• e) contacting the epoxide ester composition and hydrogen sulfide;
• and
• f) forming the thiol ester composition comprising the thiol ester molecules at conditions capable of forming the thiol ester molecules, the thiol ester molecules having ester linkages comprising:
• i) a residue of a polyol;
• and
• ii) carboxylic acid residues having a terminal α-hydroxy thiol group;
• wherein the average ratio of carboxylic acid residues having a terminal α-hydroxy thiol group to hydroxyl groups of the polyol of the residue of the polyol is greater than 0.70:1.