IP Library Granted Patent US 12686658
Granted Patent B2
US 12686658 · App. 18/995,184 · Granted Jul 21, 2026

Bidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions

Inventors: Benjamin David Herzog (Wichita, KS); William J. Tenn, III (Beaumont, TX)
Assignee: INV Nylon Chemicals Americas, LLC
C07C253/10C07F9/65746
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Quick Facts
Patent No.
US 12686658
App. No.
18/995,184
Granted
Jul 21, 2026
Kind
B2
Abstract

A bidentate phosphite ligand having the following structure: Formula (I) wherein each R 1 group is an alkyl group or an aryl group and the two R 1 groups bonded to the same phosphorus atom may be interconnected, wherein, when each R 1 group is an alkyl group, the two alkyl groups bonded to the same phosphorous atom are interconnected; and wherein each R 2 group is an alkyl group.

Claims (31)

1 . A process for the hydrocyanation of an organic compound containing at least one olefinic group comprising reacting the organic compound with hydrogen cyanide in the presence of a catalyst complex comprising at least one transition metal and a bidentate phosphite ligand having the following structure:

wherein

each R 1 group is an alkyl group or an aryl group and the two R 1 groups bonded to the same phosphorus atom may be interconnected, and

each R 2 group is an alkyl group.

2 . The process of claim 1 , wherein the organic compound comprises 1,3-butadiene.

3 . The process of claim 1 , wherein the organic compound comprises 3-pentenenitrile.

4 . The process of claim 1 , wherein a product of the hydrocyanation is a monoethylenically unsaturated compound, wherein the process further comprises double bond isomerization of the monoethylenically unsaturated compound comprising contacting the monoethylenically unsaturated compound with the catalyst complex.

5 . The process of claim 4 , wherein the monoethylenically unsaturated compound comprises 2-methyl-3-butenenitrile.

6 . The process of claim 1 , wherein each R 2 group is an alkyl group having 1 to 4 carbon atoms.

7 . The process of claim 1 , wherein each R 2 group is a methyl group.

8 . The process of claim 1 , wherein R 1 is an alkyl group having 1 to 4 carbon atoms and the two R 1 groups bonded to the same phosphorus atom may be interconnected.

9 . The process of claim 1 , wherein R 1 is an alkyl group having 1 to 4 carbon atoms and the two R 1 groups bonded to the same phosphorus atom are interconnected.

10 . The process of claim 1 , wherein the two R 1 groups bonded to the same phosphorus atom are interconnected to form the following structure:

11 . The process of claim 1 , wherein R 1 is a phenyl ring which is substituted with one or more alkyl groups having 1 to 4 carbon atoms.

12 . The process of claim 1 , wherein R 1 is a phenyl ring which is substituted with one or more methyl groups.

13 . The process of claim 1 , wherein R 1 is a xylyl group.

14 . The process of claim 1 , wherein the bidentate phosphite ligand has one of the following structures:

15 . The process of any claim 1 , wherein the at least one transition metal comprises nickel.

16 . A process for the isomerization of a monoethylenically unsaturated compound comprising contacting said compound with a catalyst complex comprising at least one transition metal and a bidentate phosphite ligand having the following structure:

wherein

each R 1 group is an alkyl group or an aryl group and the two R 1 groups bonded to the same phosphorus atom may be interconnected, and

each R 2 group is an alkyl group.

17 . A bidentate phosphite ligand having the following structure:

wherein

each R 1 group is

an alkyl group and the two R 1 groups bonded to the same phosphorus atom are interconnected to form the following structure:

R 1 is a phenyl ring which is optionally substituted with one or more alkyl groups having 1 to 4 carbon atoms, and

each R 2 group is an alkyl group.

18 . The bidentate phosphite ligand of claim 17 having one of the following structures:

19 . A catalyst complex comprising the bidentate phosphite ligand of claim 17 and at least one transition metal comprising nickel.

20 . The bidentate phosphite ligand of claim 17 , wherein R 1 is a phenyl ring which is substituted with one or more alkyl groups having 1 to 4 carbon atoms.