# US 5,349,109 A · Molybdenum-catalyzed amination of olefins

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- Number: US 5,349,109 A
- Document ID: US5349109A
- Status: Granted
- Kind: A
- Application number: 08/112,908
- Filed: 1993-08-26
- Granted: 1994-09-20
- Earliest claimed: 1991-06-04
- Assignees: The Board of Regents of the University of Oklahoma
- Inventors: Kenneth M. Nicholas; Anurag S. Srivastava
- Web page: https://patentgrep.com/patent/US5349109A

## CPC

- C07C 209/60: by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).

## Claims

### Claim 1

A process for making unsaturated .alpha.-amines from olefins wherein the .alpha.-amines have a base chain of carbon atoms having the same number of carbon atoms as the olefin, comprising:
placing a liquid olefin having at least three carbons and an .alpha.-hydrogen; a catalyst having the general formula LL'MoO(X-Y) wherein L is selected from a group consisting of monoanionic ligands, and dianionic ligands, L' is a neutral oxygen, nitrogen, or sulfur neutral donor and X-Y is selected from a group consisting of, a peroxo ligand or a nitroso ligand; and an aminating agent having the general formula RNHZ wherein Z is selected from a group consisting of,
a hydroxyl,
an alkoxy,
a halo, and
a sulfonate ester, and
wherein R is selected from a group consisting of,
a hydrogen,
an alkyl,
an aryl,
a carbonyl
a carboalkoxy or
a carboxamido,
in a reaction vessel.

### Claim 2 (depends on 1)

The process of claim 1 wherein the reaction vessel contains a nitrogen atmosphere.

### Claim 3 (depends on 2)

The process of claim 2 wherein the liquid olefin and the catalyst are added to the reaction vessel before the aminating agent.

### Claim 4 (depends on 3)

The process of claim 3 wherein the reaction vessel is maintained at a temperature of between 20.degree. and 100.degree. Centigrade during the reaction.

### Claim 5 (depends on 3)

The process of claim 3 wherein L' is selected from a group consisting of
water
alcohols,
ethers,
esters,
ketones,
amides,
nitroalkanes,
sulfoxides,
sulfoes,
nitriles and
phosphoric acid triamides.

### Claim 6 (depends on 3)

The process of claim 3 wherein the aminating agent is added at a rate wherein significant formation of aminating agent byproducts is suppressed.

### Claim 7 (depends on 3)

The process of claim 3 wherein L is selected from a group consisting of amino dicarboxylates, amino diphenolates, dithiocarbamates and carboxylates.

### Claim 8

A process for making unsaturated .alpha.-amines comprising:
placing an olefin having at least three carbons and an .alpha.-hydrogen; a solvent; a catalyst with the general formula LL'MoO(X-Y) where L is selected from a group consisting of a monoanionic ligand and a dianionic ligand, L' is a neutral oxygen, nitrogen, or sulfur donor, and X-Y is selected from a group consisting of, a peroxo ligand, or a nitroso ligand; and an aminating agent having the general formula RNHZ wherein Z is selected from a group consisting of,
a hydroxyl,
an alkoxy,
a halo, and
a sulfonate ester, and
wherein R is selected from a group consisting of,
a hydrogen,
an alkyl,
an aryl,
a carbonyl
a carboalkoxy or
a carboxamido,
in a reaction vessel.

### Claim 9 (depends on 8)

The process of claim 8 wherein the reaction vessel contains a nitrogen atmosphere.

### Claim 10 (depends on 9)

The process of claim 9 wherein the liquid olefin and the catalyst are added to the reaction vessel before the aminating agent.

### Claim 11 (depends on 10)

The process of claim 10 wherein the solvent is an organic solvent selected from a group consisting of hydrocarbons, ethers, halogenated alkanes, esters, amides, sulfoxides, nitriles, nitroalkanes, and phosphoric acid triamides.

### Claim 12 (depends on 10)

The process of claim 10 wherein the reaction vessel is maintained at a temperature of between 20.degree. and 100.degree. Centigrade during the reaction.

### Claim 13 (depends on 10)

The process of claim 10 wherein L' is selected from a group consisting of:
water
alcohols,
ethers,
esters,
ketones,
amides,
nitroalkanes,
sulfoxides,
sulfones,
nitriles and
phosphoric acid triamides.

### Claim 14 (depends on 10)

The process of claim 10 wherein the aminating agent is added at a rate wherein significant formation of aminating agent byproducts is suppressed.

### Claim 15 (depends on 10)

The process of claim 10 wherein L is selected from a group consisting of amino dicarboxylates, amino diphenolates, dithiocarbamates and carboxyiates.