Thiol ester compositions and processes for making and using same
Thiol ester compositions, methods of making the thiol ester compositions, and methods of using the thiol ester compositions are provided. In some embodiments, the thiol ester compositions include thiol esters, hydroxy thiol esters and cross-linked thiol esters. The thiol ester composition can be used to produce cross-linked thiol esters, sulfonic acid-containing esters, sulfonate containing esters and thioacrylate containing esters. The thiol ester compositions can be used to produce polythiourethanes. The polythiourethanes can be used in fertilizers and fertilizer coatings.
1. A hydroxy thiol ester composition comprising hydroxy thiol ester molecules derived from an epoxidized unsaturated natural source oil, the hydroxy thiol ester molecules having an average of at least 1.5 ester groups per hydroxy thiol ester molecule, having an average of at least 1.5 thiol groups per hydroxy thiol ester molecule, and having an average of at least 1.5 hydroxy groups per hydroxy thiol ester molecule.
2. The composition of claim 1 , wherein the hydroxy thiol ester molecules have an average ranging from 1.5 to 9 thiol groups per hydroxy thiol ester molecule.
3. The composition of claim 1 , wherein the hydroxy thiol ester molecules have an average ranging from 1.5 to 9 hydroxy groups per hydroxy thiol ester molecule.
4. The composition of claim 1 , wherein the hydroxy thiol ester molecules have an average of greater than 2.5 weight percent thiol sulfur.
5. The composition of claim 1 , wherein the hydroxy thiol ester molecules have an average ranging from 5 to 25 weight percent thiol sulfur.
6. The composition of claim 1 , wherein the hydroxy thiol ester molecules have a molar ratio of epoxide groups to thiol groups of less than 2.
7. The composition of claim 1 , wherein the composition is substantially free of epoxide groups.
8. A process for preparing a hydroxy thiol ester composition, comprising the steps of:
a) contacting hydrogen sulfide and an epoxidized unsaturated ester composition comprising an epoxidized unsaturated natural source oil or an expoxidized unsaturated triglyceride; and
b) reacting the hydrogen sulfide and the epoxidized unsaturated natural source oil or the epoxidized unsaturated triglyceride to form the hydroxy thiol ester composition comprising hydroxy thiol ester molecules having an average of at least 1.5 ester groups per hydroxy thiol ester molecule, having an average of at least 1.5 thiol groups per hydroxy thiol ester molecule, and having an average of at least 1.5 hydroxy groups per hydroxy thiol ester molecule. comprises an epoxidized natural source oil.
9. The process of claim 8 , wherein the epoxidized unsaturated ester composition comprises an epoxidized soybean oil.
10. The process of claim 8 , wherein a molar ratio of the hydrogen sulfide to epoxide groups in the epoxidized unsaturated esters is greater than 5 and the reacting step is performed at a temperature greater than 50 ° C.
11. The process of claim 8 , wherein reacting the hydrogen sulfide and the epoxidized unsaturated esters is performed in the presence of a catalyst.
12. The process of claim 8 , wherein the hydroxy thiol ester composition comprises hydroxy thiol ester molecules having an average of greater than 2.5 weight percent thiol sulfur.
13. The process of claim 8 , wherein the hydroxy thiol ester composition comprises hydroxy thiol ester molecules having an average ranging from 5 to 25 weight percent thiol sulfur.
14. The process of claim 8 , wherein the epoxidized unsaturated ester composition comprises epoxidized soybean oil, epoxidized corn oil, epoxidized castor bean oil, or epoxidized canola oil.
15. The process of claim 8 , wherein the process is practiced in the substantial absence of a solvent.
16. The process of claim 9 , wherein the hydroxy thiol ester molecules have an average of 1.5 to 9 thiol groups per hydroxy thiol ester molecule, have an average of from 1.5 to 9 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 7 ester groups per hydroxy thiol ester molecule, and have an average of from 5 to 25 weight percent thiol sulfur.
17. The process of claim 9 , wherein the hydroxy thiol ester molecules have an average of from 2 to 5 thiol groups per hydroxy thiol ester molecule, have an average of from 2 to 5 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 4 ester groups per hydroxy thiol ester molecule, and have an average of from 6 to 15 weight percent thiol sulfur.
18. The process of claim 14 , wherein the hydroxy thiol ester molecules have an average of from 1.5 to 9 thiol groups per hydroxy thiol ester molecule, have an average of from 1.5 to 9 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 7 ester groups per hydroxy thiol ester molecule, and have an average of from 5 to 25 weight percent thiol sulfur.
19. The process of claim 14 , wherein the hydroxy thiol ester molecules have an average of from 2 to 5 thiol groups per hydroxy thiol ester molecule, have an average of from 2 to 5 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 4 ester groups per hydroxy thiol ester molecule, and have an average of from 6 to 15 weight percent thiol sulfur.
20. The composition of claim 1 , wherein the epoxidized unsaturated ester composition comprises epoxidized soybean oil, epoxidized corn oil, epoxidized castor bean oil, or epoxidized canola oil.
21. The composition of claim 20 , wherein the hydroxy thiol ester molecules have an average of from 1.5 to 9 thiol groups per hydroxy thiol ester molecule, have an average of from 1.5 to 9 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 7 ester groups per hydroxy thiol ester molecule, and have an average of from 5 to 25 weight percent thiol sulfur.
22. The composition of claim 20 , wherein the hydroxy thiol ester molecules have an average of from 2 to 5 thiol groups per hydroxy thiol ester molecule, have an average of from 2 to 5 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 4 ester groups per hydroxy thiol ester molecule, and have an average of from 6 to 15 weight percent thiol sulfur.
23. The composition of claim 1 , wherein the epoxidized unsaturated ester composition comprises epoxidized soybean oil.
24. The composition of claim 23 wherein the hydroxy thiol ester molecules have an average of from 1.5 to 9 thiol groups per hydroxy thiol ester molecule, have an average of from 1.5 to 9 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 7 ester groups per hydroxy thiol ester molecule, and have an average of from 5 to 25 weight percent thiol sulfur.
25. The composition of claim 23 , wherein the hydroxy thiol ester molecules have an average of from 2 to 5 thiol groups per hydroxy thiol ester molecule, have an average of from 2 to 5 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 4 ester groups per hydroxy thiol ester molecule, and have an average of from 6 to 15 weight percent thiol sulfur.
26. A hydroxy thiol ester composition comprising hydroxy thiol ester molecules derived from an epoxized unsaturated triglyceride, the hydroxy thiol ester molecules having an average of at least 1.5 ester groups per hydroxy thiol ester molecule, having an average of at least 1.5 thiol groups per hydroxy thiol ester molecule, and having an average of at least 1.5 hydroxy groups per hydroxy thiol ester molecule.
27. The composition of claim 26 , wherein the hydroxy thiol ester molecules have an average ranging from 1 .5 to 9 thiol groups per hydroxy thiol ester molecule.
28. The composition of claim 26 , wherein the hydroxy thiol ester molecules have an average ranging from 1.5 to 9 hydroxy groups per hydroxy thiol ester molecule.
29. The composition of claim 26 , wherein the hydroxy thiol ester molecules have an average of greater than 2.5 weight percent thiol sulfur.
30. The composition of claim 26 , wherein the hydroxy thiol ester molecules have an average ranging from 5 to 25 weight percent thiol sulfur.
31. The process of claim 26 wherein the hydroxy thiol ester molecules have an average of from 1.5 to 9 thiol groups per hydroxy thiol ester molecule, have an average of from 1.5 to 9 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 7 ester groups per hydroxy thiol ester molecule, and have an average of from 5 to 25 weight percent thiol sulfur.
32. The process of claim 26 , wherein the hydroxy thiol ester molecules have an average of from 2 to 5 thiol groups per hydroxy thiol ester molecule, have an average of from 2 to 5 hydroxy groups per hydroxy thiol ester molecule, have an average of from 2 to 4 ester groups per hydroxy thiol ester molecule, and have an average of from 6 to 15 weight percent thiol sulfur.
33. The composition of claim 26 , wherein the composition is substantially free of epoxide groups.