IP Library Granted Patent US 8,658,807
Granted Patent B2
US 8,658,807 · App. 13/262,837 · Granted Feb 25, 2014

Hydrogenation process for the preparation of tetrahydrofuran and alkylated derivatives thereof

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Quick Facts
Patent No.
US 8,658,807
App. No.
13/262,837
Granted
Feb 25, 2014
Kind
B2
Abstract

A process is provided for the synthesis of tetrahydrofuran and related compounds by hydrogenation of furan and derivatives, using a sponge nickel catalyst that has been promoted with iron and chromium.

Claims (15)

1. A process for the synthesis of a compound as represented by the structure of the following Formula (I)

comprising contacting in a reaction mixture a compound as represented by the structure of the following Formula (II)

with hydrogen in the presence of a sponge nickel catalyst that comprises iron and chromium; wherein R 1 , R 2 , and R 3 are each independently selected from H and a C 1 to C 4 alkyl group.

2. A process according to claim 1 wherein R 1 , R 2 , and R 3 are each H.

3. A process according to claim 1 wherein the reaction mixture comprises hydrogen and Formula (II) compound in a ratio of between about 2.0 and about 4.0 moles of hydrogen per mole of Formula (II) compound.

4. A process according to claim 1 wherein the reaction mixture comprises hydrogen and Formula (II) compound in a ratio of between about 2.4 and about 3.0 moles of hydrogen per mole of Formula (II) compound.

5. A process according to claim 1 comprising feeding hydrogen to the reaction mixture at a pressure in the range of from about 200 to about 2500 psig.

6. A process according to claim 1 comprising feeding hydrogen to the reaction mixture at a pressure in the range of from about 500 to about 1000 psig.

7. A process according to claim 1 wherein the sponge nickel catalyst comprises iron in an amount of from about 0.5 to about 6 wt %.

8. A process according to claim 1 wherein the sponge nickel catalyst comprises chromium in an amount of from about 0.5 to about 6 wt %.

9. A process according to claim 1 wherein the reaction mixture has a temperature in the range of from about 30° C. to about 150° C.

10. A process according to claim 1 further comprising a step of decarbonylating a compound as represented by the structure of the following Formula (III)

to provide the Formula (II) compound.

11. A process according to claim 10 wherein the compound of Formula (III) is derived from a biological material which is selected from the group consisting of: straw, corn cobs, corn stalks/corn stover, sugar bagasse, hardwoods, cotton stalks, kenaf, oat hulls, and hemp.

12. A process according to claim 1 further comprising a step of subjecting the Formula (I) compound to a reaction to prepare therefrom a compound, oligomer or polymer.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2025
From: DUPONT US HOLDING, LLC,
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 069866/0734 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2025
From: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
To: COVATION INC
Reel/Frame 069867/0341 →
CORRECTIVE ASSIGNMENT TO CORRECT THE DESIGNATION OF ASSIGNEE AS A DELAWARE CORPORATION TO A DELAWARE LIMITED LIABILITY COMPANY PREVIOUSLY RECORDED ON REEL 049880 FRAME 0001. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 28, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT US HOLDING, LLC
Reel/Frame 051502/0610 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT US HOLDING, LLC
Reel/Frame 049880/0001 →