Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality
View Patent ↗A process is provided comprising contacting 1,3-propanediol with a suitable polymerization catalyst to produce polytrimethylene ether glycol or random polytrimethylene ether ester, wherein the 1,3-propanediol comprises about 10 microg/g or less peroxide compounds, based on the weight of 1,3-propanediol, and about 100 microg/g or less carbonyl compounds based on the weight of the 1,3-propanediol. Preferably, the 1,3-propanediol comprises about 100 microg/g or less of monofunctional alcohol compounds based on the weight of the PDO. In addition, polytrimethylene ether glycol and random polytrimethylene ether ester prepared by the process.
1. A process comprising contacting 1,3-propanediol with a suitable polymerization catalyst to produce polytrimethylene ether glycol, wherein the 1,3-propanediol, before contact, comprises about 10 microg/g or less peroxide compounds, based on the weight of 1,3-propanediol, and about 100 microg/g or less carbonyl compounds based on the weight of the 1,3-propanediol.
2. The process of claim 1 , wherein the 1,3-propanediol further comprises about 100 microg/g or less monofunctional alcohol compounds based on the weight of the 1,3-propanediol.
3. The process of claim 1 , wherein the 1,3-propanediol further comprises about 75 microg/g or less carbony compounds based on the weight of the 1,3-propanediol.
4. The process of claim 1 , wherein the 1,3-propanediol further comprises about 75 microg/g or less monofunctional alcohol compounds based on the weight of the 1,3-propanediol.
5. The process of claim 3 , wherein the 1,3 propanediol further comprises about 75 microg/g or less mono-functional alcohol compounds based on the weight of the 1,3-propanediol.
6. The process of claim 1 , wherein the 1,3-propanediol further comprises about 50 microg/g or less carbonyl compounds based on the weight of the 1,3-propanediol.
7. The process of claim 1 , wherein the 1,3-propartediol further comprises about 50 microg/g or less monofunctional alcohol compounds based on the weight of the 1,3-propanediol.
8. The process of claim 6 , wherein the 1,3-propanediol further comprises about 50 microg/g or less mono-functional alcohol compounds based on the weight of the 1,3-propanediol.
9. The process of claim 1 , wherein the 1,3-propanediol further comprises about 25 microg/g or less carbonyl compounds based on the weight of the 1,3-propanediol.
10. The process of claim 1 , wherein the 1,3-propanediol further comprises about 25 microg/g or less monofunctional alcohol compounds based on the weight of the 1,3-propanediol.
11. The process of claim 9 , wherein the 1,3 propanediol further comprises about 25 microg/g or less monofunctional alcohol compounds based on the weight of the 1,3-propanediol.
12. The process of claim 1 , wherein the 1,3-propanediol is at least 99.95% pure.
13. The process of claim 1 , wherein the 1,3-propanediol comprises biochemically-derived 1,3-propanediol.
14. The process of claim 13 , wherein the 1,3-propanediol is derived from a fermentation process.
15. The process of claim 14 , wherein the 1,3-propanediol is derived from a fermentation process using a renewable biological source.
16. The process of claim 15 , wherein the 1,3-propanediol is produced from a carbohydrate.
17. The process of claim 15 , wherein the 1,3-propanediol is produced from glucose from corn.
18. The process of claim 1 , wherein the 1,3-propanediol has a color value of less than about 10 APHA.
19. The process of claim 1 , wherein the 1,3-propanediol has a color value of less than about 5 APHA.
20. The process of claim 1 , wherein the 1,3-propanediol has a color value less than about 15 APHA when treated with 1 wt. % sulfuric acid at 170° C. for 10 minutes.
21. The process of claim 1 , wherein the polytrimethylene ether glycol has a color of less than about 50 APHA.
22. The process of claim 20 , wherein the polytrimethylene ether glycol has a color of less than 30 APHA.
23. The process of claim 1 , wherein the polytrimethylene ether glycol has a molecular weight of from about 250 to about 5000.
24. The process of claim 10 , wherein the poly-trimethylene ether glycol has a molecular weight of from about 250 to about 5000 and has a color of less than 30 APHA.
25. The process of claim 1 , wherein the polytrimethylene ether glycol comprises a homopolymer.
26. The process of claim 1 , wherein the polytrimethylene ether glycol comprises a copolymer.
27. The process of claim 1 , wherein the polytrimethylene ether glycol comprises a copolymer of 1,3-propanediol, with at least one other C2 or C6 to C12 diol.
28. The process of claim 1 , wherein the 1,3-propanediol has a 50/50 pH of about 6.0-7.5.
29. The process of claim 1 , wherein the 1,3-propanediol has a 50/50 pH of about 6.0-7.0.
30. A process comprising contacting a bio-chemically-derived 1,3-propanediol with a suitable polymerization catalyst to produce polytrimethylene ether glycol, wherein the 1,3-propanediol has a 50/50 pH of about 6.0-7.5 and comprises about 100 microg/g or less carbonyl compounds, about 10 microg/g or less peroxide compounds and about 100 microg/g or less monofunctional alcohol compounds.
31. The process of claim 30 , wherein the 1,3-propanediol has a color of less than about 10 APHA.
32. The process of claim 31 , wherein the polytrimethylene ether glycol has a molecular weight of from about 250 to about 5000.
33. A polytrimethylene ether glycol prepared by providing 1,3-propanediol and polymerization catalyst and polymerizing 1,3-propanediol with the polymerization catalyst to form the polytrimethylene ether glycol, wherein the 1,3-propanediol contains about 100 microg/g or less carbonyl compounds, about 10 microg/g or less peroxide compounds and about 100 microg/g or less monofunctional alcohol compounds, based on the weight of 1,3 propanediol.
34. A polytriznethylene ether glycol composition as claimed in claim 33 .
35. The polytrimethylene ether glycol composition of claim 34 wherein the 1,3-propanediol is bio-chemicallyderived 1,3-propanediol made from a carbohydrate from a renewable source.
36. The polytrimethylene ether glycol composition of claim 35 , wherein the polytrimethylene ether glycol has a molecular weight of from about 250 to about 5000 and has a color of less than 30 APHA.
37. The process of claim 1 wherein the 1,3-propanediol used in the process is selected based upon it comprising about 10 microg/g or less peroxide compounds, based on the weight of 1,3-propanediol, and about 100 microg/g or less carbonyl compounds based on the weight of the 1,3-propanediol.