Heterogeneous hydrocyanation

Patent metadata

Field	Value
Publication number	US-9834506-B2
Application number	US-201415102792-A
Country	US
Kind code	B2
Filing date	Dec 18, 2014
Priority date	Dec 19, 2013
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

The present invention relates to an improved process for addition of hydrogen cyanide across olefins and, in particular, to the use of a specific aluminum oxide to catalyze the reaction. The aluminum oxide catalyst must have total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 3,000 ppm by weight.

First claim

What is claimed is:

1. A process for addition of hydrogen cyanide across an olefin which comprises contacting an olefin with hydrogen cyanide at reaction conditions in the presence of an aluminum oxide catalyst, wherein the aluminum oxide catalyst has total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 3,000 ppm by weight.

2. The process of claim 1 wherein the aluminum oxide catalyst has total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 1000 ppm by weight.

3. The process of claim 1 wherein the aluminum oxide catalyst has total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of from 0 to 100 ppm by weight.

4. The process of claim 1 wherein the alkali metal is selected from the group consisting of sodium, potassium and combinations thereof, and the alkaline earth metal is selected from the group consisting of magnesium, calcium and combinations thereof.

5. The process of claim 3 wherein the alkali metal is sodium and the alkaline earth metal is calcium.

6. The process of claim 1 wherein the olefin comprises a pentenenitrile, a butenenitrile or a combination thereof.

7. The process of claim 6 wherein the olefin is selected from the group consisting of cis-2-pentenenitrile, 3-pentenenitrile, 2-methyl-3-butenenitrile, and combinations thereof.

8. The process of claim 3 wherein the olefin is selected from the group consisting of cis-2-pentenenitrile, 3-pentenenitrile, 2-methyl-3-butenenitrile, and combinations thereof.

9. The process of claim 5 wherein the olefin is selected from the group consisting of cis-2-pentenenitrile, 3-pentenenitrile, 2-methyl-3-butenenitrile, and combinations thereof.

10. The process of claim 1 wherein the reaction conditions include a temperature of from 50 to 450° C. and pressure from 760 to 5,000 mmHg.

11. The process of claim 1 wherein the reaction conditions include a temperature of from 50 to 150° C. and pressure from 760 to 5,000 mmHg.

12. The process of claim 1 wherein the reaction conditions include a temperature of from >150 to 450° C. and pressure from 760 to 5,000 mmHg.

13. A process for manufacturing ethylsuccinonitrile which comprises contacting cis-2-pentenenitrile, 3-pentenenitrile or a combination thereof with hydrogen cyanide in the liquid phase or vapor phase at reaction conditions in the presence of an aluminum oxide catalyst, wherein the aluminum oxide catalyst has total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 3,000 ppm by weight.

14. The process of claim 13 wherein the aluminum oxide catalyst has total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 1000 ppm by weight.

15. The process of claim 13 wherein the reaction conditions include a temperature of from 55 to 125° C. and pressure from 760 to 2,500 mmHg.

16. The process of claim 13 wherein the reaction conditions include a temperature of from 160 to 225° C. and pressure from 760 to 3,500 mmHg.

17. A process for manufacturing 2,3-dimethylsuccinonitrile which comprises contacting cis-2-methyl-2-butenenitrile, trans-2-methyl-2-butenenitrile, 2-methyl-3-butenenitrile or a combination thereof with hydrogen cyanide in the liquid phase at reaction conditions in the presence of an aluminum oxide catalyst, wherein the aluminum oxide catalyst has total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 3,000 ppm by weight.

18. The process of claim 17 wherein the aluminum oxide catalyst has total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 1000 ppm by weight.

Assignees

• Invista North America Sarl
• Invista North America Sarl

Inventors

• Tenn Iii William J
• Aki Sudkir N V K

Classifications

• B01J23/02

  of the alkali- or alkaline earth metals or beryllium · CPC title

• B01J23/06

  of zinc, cadmium or mercury · CPC title

• B01J23/10

  of rare earths · CPC title

• C07C253/10 Primary

  to compounds containing carbon-to-carbon double bonds · CPC title

• B01J21/066

  Zirconium or hafnium; Oxides or hydroxides thereof · CPC title