Hydrogenolysis of Glycerol and Products Produced Therefrom

• US 20080228014A1
• Filed: 05/30/2008
• Published: 09/18/2008
• Est. Priority Date: 10/23/2006
• Status: Active Grant

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Archer Daniels Midland Company
• Inventors: Bloom, Paul
• Granted Patent: US 8,153,847 B2
• Time in Patent Office: Days
• US Class Current: 568/852
• 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

Abstract

Processes for the hydrogenolysis of glycerol, as well as products produced therefrom are disclosed.

Claims

1. A process for producing biobased propylene glycol, the process comprising:

placing a biobased glycerol containing solution at a concentration of at least 30% glycerol by weight and hydrogen in contact with a solid catalyst such that the biobased propylene glycol is formed.

2. The process according to claim 1, further comprising measuring a content of the propanediols in the biobased propylene glycol.

3. The process according to claim 1, wherein the biobased glycerol containing solution in placed in contact with the hydrogen and the solid catalyst at a Liquid Hourly space velocity of between 0.5 hr⁻

1 to 10.0 hr<sup>−

1</sup>.

4. The process according to claim 1, further comprising placing a base in contact with the biobased glycerol containing solution, the hydrogen and the solid catalyst.

5. The process according to claim 4, wherein the base is selected from the group consisting of alkali metal hydroxides, alkoxides and basic salts and alkaline earth metal oxides, alkoxides, hydroxides, basic salts, and combinations of any thereof.

6. The process according to claim 1, further comprising maintaining a reaction temperature of between 178-205 degrees Centigrade such that the biobased propylene glycol is formed.

7. The process according to claim 1, further comprising:

mixing an acylglycerol containing material with an alcohol, thus producing a biodiesel precursor mixture;

subjecting the biodiesel precursor mixture to a condition that allows biodiesel and the biobased glycerol containing material to form; and

fractionating the biobased glycerol containing material from the biodiesel.

8. The process according to claim 7, further comprising purifying the biobased glycerol containing material.

9. The process according to claim 1, further comprising isolating the biobased propylene glycol.

10. The process according to claim 1, wherein a product of the process comprises 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 2,4-pentanediol, ethylene glycol or any combinations thereof at a concentration of less than 0.5% of the biobased propylene glycol concentration on dry weight basis.

11. A process for producing biobased propylene glycol, the process comprising:

placing a bio-derived polyol feedstock containing solution at a concentration of at least 30% of the bio-derived polyol feedstock by weight and hydrogen in contact with a solid catalyst such that the biobased propylene glycol is formed.

12. The process according to claim 11, wherein the solid catalyst comprises a compound selected from the group consisting of palladium, rhenium, nickel, rhodium, copper, zinc, chromium and any combinations thereof.

13. The process according to claim 11, wherein the bio-derived polyol feedstock is selected from the group consisting of glucose, sorbitol, mannitol, sucrose, lactose, maltose, alpha-methyl-d-glucoside, pentaacetylglucose, gluconic lactone, glycerol and any combinations thereof.

14. The process according to claim 11, further comprising isolating the biobased propylene glycol.

15. The process according to claim 11, further comprising placing a base in contact with the bio-derived polyol feedstock containing solution, the hydrogen and the solid catalyst.

16. The process according to claim 11, wherein the bio-derived polyol feedstock is selected from the group consisting of biobased glycerol, biobased sorbitol and a combination thereof.

17. The process according to claim 11, wherein a product of the process comprises 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 2,4-pentanediol, ethylene glycol or any combinations thereof, the 1,2-butanediol, the 1,3-butanediol, the 1,4-butanediol, the 2,3-butanediol, the 2,4-pentanediol, the ethylene glycol or any of the combinations thereof being present at a concentration of less than 0.5% of the propylene glycol concentration on dry weight basis.

18. A process for producing biobased propylene glycol, the process comprising:

placing a biobased glycerol containing solution, a biobased sorbitol containing solution or a combination thereof at a concentration of at least 30% by weight and hydrogen in contact with a solid catalyst such that the biobased propylene glycol is formed; and

isolating the biobased propylene glycol.

19. The process according to claim 18, wherein the solid catalyst comprises a compound selected from the group consisting of palladium, rhenium, nickel, rhodium, copper, zinc, chromium and any combinations thereof.

20. The process according to claim 18, further comprising placing a base in contact with the biobased glycerol containing solution, the biobased sorbitol containing solution or the combination thereof, the hydrogen and the solid catalyst.