Hydrogenation process

• US 8,324,434 B2
• Filed: 02/28/2009
• Issued: 12/04/2012
• Est. Priority Date: 03/02/2008
• Status: Expired due to Fees

• Current Assignee: Dow Global Technologies LLC (Dow, Inc.)
• Original Assignee: Dow Global Technologies LLC (Dow, Inc.)
• Inventors: Molzahn, David C., Burdett, Kenneth A., Gibson, William L., Mathur, Indresh, Kriel, Karel J., McCreight, James E.
• Primary Examiner(s): Katakam, Sudhakar
• Application Number:
  US12/918,814
• Publication Number:
  US 20110060168A1
• Time in Patent Office: 1,375 Days
• Field of Search: None
• US Class Current: 568/861
• 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

The present invention provides an improved hydrogenation processes wherein heat is efficiently managed so that catalyst productivity is optimized. More particularly, in the processes of the present invention, a nonaqueous solvent is added to a reactant to provide a nonaqueous solvent/reactant mixture that can act as a heat sink and absorb at least a portion of the heat generated within the reactor. Desirably, a reaction product, or a solvent with a minimal number of hydroxyl groups, is utilized so that the formation of unwanted byproducts can be minimized.

Claims

1. A hydrogenation process comprising:

(a) combining a reactant with a nonaqueous solvent to form a nonaqueous solvent/reactant mixture;

(b) contacting the nonaqueous solvent/reactant mixture with hydrogen in the presence of a copper aluminum catalyst within an adiabatic reactor to form a reaction product; and

(c) removing at least a portion of any water present in the reaction product with a water removal process driven at least in part by the heat of reaction of the hydrogenation reaction.

2. The process of claim 1, wherein the reactant is glycerin and the reaction product preferentially comprises propylene glycol.

3. The process of claim 1, wherein the nonaqueous solvent comprises a solvent with a hydroxyl wt % of less than about 45 and a hydroxyl weight equivalent of greater than about 30.

4. The process of claim 3, wherein the nonaqueous solvent comprises the reaction product and the glycerin is crude glycerin.

5. The process of claim 2, wherein the glycerin is crude glycerol.

6. A glycerin hydrogenation process comprising:

(a) combining a glycerin feedstock with a nonaqueous solvent to provide a nonaqueous solvent/glycerin mixture having less than about 5 weight percent water; and

(b) contacting the nonaqueous solvent/glycerin mixture with hydrogen in the presence of a catalyst within an adiabatic reactor to preferentially form a propylene glycol reaction product comprising less than about 17 wt % water.

7. The process of claim 6, wherein the propylene glycol reaction product comprises less than about 6 weight percent water.

8. The process of claim 6, wherein the nonaqueous solvent comprises a solvent with a hydroxyl wt % of less than about 45 and a hydroxyl weight equivalent of greater than about 30.

9. The process of claim 6, nonaqueous solvent comprises a reaction product, and prior to the contacting step, the reaction product/glycerin mixture is subjected to a distillation step.

10. The process of claim 9, wherein the product of the distillation step is subjected to a flash evaporator/condensing step prior to the contacting step.