Hydrogenolysis of Glycerol and Products Produced Therefrom

• US 20080103339A1
• Filed: 10/23/2007
• Published: 05/01/2008
• 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 7,928,148 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 composition, comprising:

a biobased propylene glycol; and

a weight/weight ratio of polyhydric alcohols other than propylene glycol to the biobased propylene glycol of 0.5% or less.

2. The composition of claim 1, further comprising ethylene glycol at a concentration of less than 0.25%.

3. The composition of claim 1, wherein the polyhydric alcohols are selected from the group consisting of 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 2,4-pentanediol, ethylene glycol and any combinations thereof.

4. The composition of claim 1, wherein the biobased propylene glycol is of a glycerol origin.

5. The composition of claim 1, wherein the weight/weight ratio of the polyhydric alcohols to the biobased propylene glycol of 0.25% or less.

6. A composition, comprising:

a biobased propylene glycol; and

polyhydric alcohols other than propylene glycol;

wherein a ratio of the biobased propylene glycol to the polyhydric alcohols is between 100;

1 and 1000;

1.

7. The composition of claim 6, further comprising ethylene glycol at a concentration of less than 0.3%.

8. The composition of claim 6, wherein the biobased propylene glycol is of a glycerol origin.

9. A system for producing biobased propylene glycol, comprising:

a conduit comprising a biobased glycerol containing solution at a concentration of at least 30% glycerol;

a reactor comprising a solid catalyst; and

a second conduit comprising;

a biobased propylene glycol; and

polyhydric alcohols other than propylene glycol, wherein a weight/weight ratio of the polyhydric alcohols to the biobased propylene glycol is 0.5% or less.

10. The system of claim 9, wherein the reactor further comprises a base.

11. The system of claim 10, 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

12. The system of claim 9, wherein the reactor further comprises hydrogen.

13. 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.

14. The process according to claim 13, further comprising measuring a content of the propanediols in the propylene glycol containing solution.

15. The process according to claim 13, 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>.

16. The process according to claim 13, further comprising placing a base in contact with the biobased glycerol containing solution, the hydrogen and the solid catalyst.

17. The process according to claim 16, 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.

18. The process according to claim 13, further comprising maintaining a reaction temperature of between 178-205 degrees Centigrade such that the biobased propylene glycol is formed.

19. The process according to claim 13, 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.

20. A composition, comprising:

polyhydric alcohols obtained from a biobased feed stock;

wherein the polyhydric alcohols comprise;

propylene glycol in an amount of at least 997 g/kg on a dry weight basis; and

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.