Preparation of Derivative of Polyhydric Alcohols

• US 20080274019A1
• Filed: 04/23/2008
• Published: 11/06/2008
• Est. Priority Date: 04/24/2007
• Status: Abandoned Application

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Archer Daniels Midland Company
• Inventors: Binder, Thomas P., Hilaly, Ahmad K., Beggin, Joseph Robert, Karcher, Lawrence P., Zenthoefer, Brad
• Application Number:
  US12/108,060
• Publication Number:
  US 20080274019A1
• Time in Patent Office: Days
• US Class Current: 422/129
• CPC Class Codes: C07C 29/00 Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
• CPC Class Codes: C07C 29/60 by elimination of -OH groups, e.g. by dehydration C07C29/34 takes precedence
• CPC Class Codes: C07C 31/205 1,3-Propanediol; 1,2-Propanediol
• CPC Class Codes: C07C 31/207 1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol

Abstract

A method for converting a polyhydric alcohol into propylene glycol and butanediols is disclosed. Also disclosed are methods for converting polyhydric alcohols into three-carbon products and four-carbon products. Also disclosed are methods for maximizing conversion of polyhydric alcohols and minimizing formation of reaction products that are difficult to remove from the desired product. In other embodiments, methods are described to optimize use of reactants, including hydrogen, in hydrogenolysis of polyhydric alcohols.

Claims

1. A system for treating glycerol or sorbitol comprising:

a reactor operably configured to convert the glycerol or the sorbitol to a reaction product comprising propylene glycol and a butanediol selected from the group consisting of 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, and combinations of any thereof;

a first conduit comprising the glycerol or the sorbitol operably connected to the reactor;

a product purifier operably configured to remove the butanediol from the reaction product; and

a second conduit comprising the reaction product operably connected to the reactor and the product purifier.

2. The system of claim 1, further comprising a third conduit comprising a product purifier effluent operably connected to the product purifier.

3. The system of claim 2, wherein a content of the butanediol in the reaction product is greater than the content of butanediol in the product purifier effluent.

4. The system of claim 1, wherein the content of butanediol in the reaction product is 0.04 to 2.31 grams/100 grams of solution.

5. The system of claim 1, wherein a content of the butanediol in product purifier effluent is less than 0.02%.

6. The system of claim 1, further comprising means for purifying the glycerol before the glycerol enters the first conduit.

7. The system of claim 6, wherein the means for purifying the glycerol purifies the glycerol by an act selected from the group consisting of placing a solution of glycerol in an electro-dialysis apparatus, distilling a solution of glycerol, subjecting a solution of glycerol to ion exchange, and combinations of any thereof, thus removing salt impurities from the glycerol.

8-9. -9. (canceled)

10. A process for converting a polyhydric alcohol into a three-carbon compound, a four-carbon compound or a combination thereof, the process comprising:

combining the polyhydric alcohol with hydrogen, thus forming a reaction mixture;

heating the reaction mixture;

placing the reaction mixture in contact with a catalyst, thus forming a reaction product;

acidifying the reaction product; and

removing the three-carbon compound, the four-carbon compound, or any combination thereof from the acidified reaction product.

11. The process of claim 10, wherein the polyhydric alcohol comprises glycerol, sorbitol or a combination thereof.

12. The process of claim 10, wherein the four-carbon compound comprises a compound selected from the group consisting of 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, and combinations of any thereof.

17. The process of claim 10, wherein the three-carbon compound product comprises propylene glycol.

18. The process of claim 10, further comprising purifying the three-carbon compound, the four carbon compound or the combination thereof.

19. The process of claim 18, wherein the ratio of three-carbon product to four-carbon product after the purifying is different from the ratio of three-carbon product to four-carbon product before the purifying.

20. The process of claim 18, wherein the purifying comprises an act selected from the group consisting of ion exclusion, electro-dialysis, filtration, distillation, ion exchange, and any combinations thereof.

22. A composition enriched in a four-carbon compound produced by the process of claim 10.

24. A composition enriched in a three-carbon compound produced by the process of claim 10.

32. The process of claim 10, wherein the polyhydric alcohol is glycerol, sorbitol or a combination thereof, the process further comprising:

separating a vapor, a gas or a combination thereof from the reaction product;

wherein the three-carbon compound is propylene glycol and the four-carbon compound is ethylene glycol.

34. The process of claim 32, wherein

the catalyst is a heterogeneous catalyst selected from the group consisting of rhenium, nickel, and a combination thereof;

and

the catalyst is embedded in an activated carbon matrix.

13-16. -16. (canceled)

21. (canceled)

23. (canceled)

25-31. -31. (canceled)

33. (canceled)

35-38. -38. (canceled)

39. A composition comprising a bio-based propylene glycol having a measurable content of butanediol, wherein the content of butanediol is less than 0.25%.

40. The composition of claim 39, wherein the butanediol content is less than 0.1%.

41-45. -45. (canceled)