Pentenenitrile isomerization

Patent metadata

Field	Value
Publication number	US-9440912-B2
Application number	US-201314649644-A
Country	US
Kind code	B2
Filing date	Dec 5, 2013
Priority date	Dec 7, 2012
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

Disclosed is a process for isomerizing cis-2-pentenenitrile to 3-pentenenitrile in the presence of a non-aluminum metal oxide catalyst, wherein: (a) the metal in the catalyst has an oxidation state in the range from +1 to +4; (b) the metal has a cation radius in the range from 0.35 to 1.0 Å; (c) the metal of the catalyst has a polarizing power, C/r, is in the range from 2 to >8, wherein C is the charge of the metal and r is the ionic radius in Å; (d) the bond network of the catalyst has a % ionicity of >20; (e) the metal oxide has an acidity strength in the range from strong to very weak; and (f) the metal oxide has a basicity (nucleophilicity) strength of weak to strong.

First claim

The invention claimed is:

1. A process for isomerizing cis-2-pentenenitrile to 3-pentenenitrile comprising contacting cis-2-pentenenitrile with a non-aluminium metal oxide catalyst under conversion conditions including a temperature of 50 to 250° C. and a pressure from 0.5 to 50 atmospheres, wherein the non-aluminium metal oxide catalyst is a metal oxide selected from the group consisting of:
(i) ZrO 2 doped with Ce 2 O 3 or La 2 O 3 or both Ce 2 O 3 and La 2 O 3 ; and
(ii) Cr 2 O 3 , ZnO, Fe 2 O 3 , CoO, NiO, CuO and mixtures thereof;
and wherein:
(a) the metal in the catalyst has an oxidation state in the range from +1 to +4;
(b) the metal has a cation radius in the range from 0.35 to 1.0 Å;
(c) the metal of the catalyst has a polarising power, C/r, in the range from 2 to →8, wherein C is the charge of the metal and r is the ionic radius in Å;
(d) the bond network of the catalyst has a % ionicity of >20;
(e) the metal oxide has an acidity strength in the range from strong to very weak; and
(f) the metal oxide has a basicity (nucleophilicity) strength of weak to strong.

2. A process according to claim 1 , wherein the metal oxide is selected from the group consisting of Cr 2 O 3 , ZnO and mixtures thereof.

3. A process according to claim 1 , wherein the isomerization is carried out in the liquid phase.

4. A process according to claim 1 , wherein the isomerization is carried out in the gas phase.

5. A process according to claim 1 , wherein the isomerization is carried out at a temperature in the range from 120° C. to 200° C.

6. A process according to claim 1 , wherein the metal of the catalyst has a polarising power, C/r, in the range from 4 to 8.

7. A process according to claim 1 , wherein the metal has a cation radius in the range from 0.5 to 0.9 Å.

8. A process according to claim 1 , wherein the metal in the catalyst has an oxidation state in the range from +2 to +4.

Assignees

• Invista North America Sarl
• Invista North America Sarl

Inventors

• Aki Sudhir N V K
• Tenn Iii William J
• Vos Thomas E

Classifications

• B01J23/06

  of zinc, cadmium or mercury · CPC title

• B01J23/10

  of rare earths · CPC title

• C07C253/30 Primary

  by reactions not involving the formation of cyano groups · CPC title

• B01J27/053

  Sulfates · CPC title

• B01J23/44

  Palladium · CPC title