IP Library Granted Patent US 7,323,539
Granted Patent B2
US 7,323,539 · App. 10/918,079 · Granted Jan 29, 2008

Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality

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Quick Facts
Patent No.
US 7,323,539
App. No.
10/918,079
Granted
Jan 29, 2008
Kind
B2
Abstract

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.

Claims (37)

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.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE ENTITY TYPE PREVIOUSLY RECORDED AT REEL: 049879 FRAME: 0043. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 6, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 050300/0408 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 049879/0043 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 23, 2004
From: SUNKARA, HARI BABU; NG, HOWARD C.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 015389/0199 →