IP Library Granted Patent US 8,754,245
Granted Patent B2
US 8,754,245 · App. 13/392,550 · Granted Jun 17, 2014

Vapor-phase decarbonylation process

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Quick Facts
Patent No.
US 8,754,245
App. No.
13/392,550
Granted
Jun 17, 2014
Kind
B2
Abstract

A process is provided for the synthesis of furan and related compounds by vapor-phase decarbonylation of furfural and derivatives, using a palladium/metal aluminate catalyst that has been promoted with an alkali carbonate, such as cesium carbonate. The use of such catalysts, which are inherently less acidic than alumina, results in improved lifetime and high productivity.

Claims (16)

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

by providing a compound as represented by the following structure of Formula (II)

in the form of a gas, heating a Pd/metal aluminate catalyst that has been promoted with an alkali carbonate, and contacting the Formula (II) compound and the catalyst to produce a Formula (I) product;

wherein R 1 , R 2 , and R 3 are each independently selected from H and a C 1 to C 4 hydrocarbyl group.

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

3. The process according to claim 1 wherein the metal aluminate is an alkali metal aluminate, an alkaline earth metal aluminate, gallium aluminate, lanthanum aluminate, or yttrium aluminate.

4. The process according to claim 3 wherein the alkali metal aluminate is LiAlO 2 .

5. The process according to claim 1 wherein the alkali carbonate is cesium carbonate.

6. The process according to claim 1 where the alkali content of the promoted catalyst is between 1 and 100 mg per g catalyst.

7. The process according to claim 1 wherein hydrogen is co-fed with the Formula (II) compound.

8. The process according to claim 1 wherein water is added to the Formula (II) compound.

9. The process according to claim 1 wherein contacting the Formula (II) compound and the catalyst to produce a Formula (I) product occurs in the gas phase at a temperature that is in the range of from about 200° C. to about 400° C.

10. The process according to claim 9 wherein the temperature is in the range of from about 270° C. to about 330° C.

11. The process according to claim 1 , further comprising purifying the Formula (I) product.

12. The process according to claim 11 , wherein the Formula (I) product is purified by distillation.

13. The 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 20, 2024
From: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
To: COVATION INC.
Reel/Frame 066356/0850 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2024
From: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
To: COVATION INC.
Reel/Frame 066350/0534 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ENTITY FOR ASSIGNEE PREVIOUSLY RECORDED AT REEL: 49879 FRAME: 212. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 6, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 050301/0065 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 049879/0212 →