# US 4,395,554 A · Process for producing alpha-picoline

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- Number: US 4,395,554 A
- Document ID: US4395554A
- Status: Granted
- Kind: A
- Application number: 06/369,296
- Filed: 1982-04-16
- Granted: 1983-07-26
- Earliest claimed: 1981-12-01
- Assignees: Mobil Oil Corporation
- Inventors: Clarence D. Chang; Patrick D. Perkins
- Web page: https://patentgrep.com/patent/US4395554A

## CPC

- C07D 213/06: containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D 213/08: Preparation by ring-closure
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Alpha-picolines are produced by containing aniline or substituted anilines, such as alkyl-, cyclo alkyl-, halo- ; alkoxy- or substituted alkyl-anilines with a crystalline zeolite catalyst having a silica:alumina ratio of at least 12 and a constraint index of 1 to 12. ZSM-5 type catalysts are contacted at elevated temperature to yield alpha-picolines selectively.

## Claims

### Claim 1

A method of making alpha-picoline or a substituted alpha picoline by contacting aniline or a substituted aniline with a crystalline zeolite catalyst.

### Claim 2 (depends on 1)

A method according to claim 1 in which aniline is contacted with the zeolite to form alpha-picoline.

### Claim 3 (depends on 2)

A method according to claim 2 in which the aniline is contacted with the zeolite in the presence of ammonia.

### Claim 4 (depends on 3)

A method according to claim 3 in which the molar ratio of the ammonia to the aniline is from 0.5:1 to 25:1.

### Claim 5 (depends on 1)

A method according to claim 1 in which the zeolite has a silica:alumina ratio of at least 12:1 and a Constraint Index of 1 to 12.

### Claim 6 (depends on 5)

A method according to claim 5 in which the zeolite is ZSM-5.

### Claim 7 (depends on 5)

A method according to claim 5 in which the zeolite is ZSM-11.

### Claim 8 (depends on 5)

A method according to claim 5 in which the zeolite is ZSM-12.

### Claim 9 (depends on 5)

A method according to claim 5 in which the zeolite is ZSM-35.

### Claim 10 (depends on 5)

A method according to claim 5 in which the zeolite is ZSM-38.

### Claim 11 (depends on 2)

A method according to claim 2 in which the aniline is contacted with the zeolite at a temperature from 200.degree. C. to 650.degree. C., a pressure from 200 to 25,000 kPa and a space velocity of 0.1 to 50 WHSV.

### Claim 12

A method of making alpha-picolines by contacting aniline or a substituted aniline with a crystalline zeolite catalyst, said substituted aniline being substituted in the aromatic nucleus or amino group with one or more alkyl, cycloalkyl, alkoxy, halogen, nitro or substituted-alkyl group.

### Claim 13

A catalytic process for converting aniline to alpha-picoline in the presence of ammonia which comprises the steps of
contacting a vapor phase reaction mixture of ammonia and aniline having a molar ratio of about 0.5:1 to 25:1 ammonia to aniline with a ZSM-5 type crystalline aluminosilicate catalyst at a temperature of about 200.degree. C. to 650.degree. C. and a space velocity of about 0.1 to 50 WHSV.