IP Library Granted Patent US 8,247,561
Granted Patent B2
US 8,247,561 · App. 12/934,465 · Granted Aug 21, 2012

Preparation of methylpentamethylenediamine and methylpiperidine

Assignee: Rhodia Operations
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Quick Facts
Patent No.
US 8,247,561
App. No.
12/934,465
Granted
Aug 21, 2012
Kind
B2
Abstract

Methyl-2-pentamethylenediamine and methyl-3-piperidine are prepared by hydrogenation of methylglutaronitrile in the presence of a catalyst including cobalt, chromium, and nickel, especially a catalyst based on Raney cobalt doped with nickel and chromium.

Claims (16)

1. A process for the preparation of 2-methylpentamethylenediamine and 3-methylpiperidine, comprising hydrogenating methylglutaronitrile in the presence of a catalyst which comprises cobalt doped with nickel and chromium, under an absolute hydrogen pressure of less than 50 bar.

2. The process as defined by claim 1 , wherein the hydrogenation reaction is carried out under an absolute hydrogen pressure ranging from 10 to 35 bar.

3. The process as defined by claim 1 , wherein the hydrogenation is carried out in the presence of a solvent selected from the group consisting of alcohols, water or mixture thereof.

4. The process as defined by claim 1 , wherein the hydrogenation is carried out in the presence of a strong basic inorganic compound selected from the group consisting of alkali metal hydroxides and ammonium hydroxide.

5. The process as defined by claim 1 , wherein the hydrogenation is carried out at a temperature ranging from 60 to 160° C.

6. The process as defined by claim 1 , wherein the percentage by weight of cobalt in the catalyst, expressed as Co, ranges from 85% to 98%, with respect to the weight of catalyst.

7. The process as defined by claim 1 , wherein the percentage by weight of nickel in the catalyst, expressed as Ni, ranges from 0.1% to 4%, with respect to the weight of catalyst.

8. The process as defined by claim 1 , wherein the percentage by weight of chromium in the catalyst, expressed as Cr, ranges from 0.1% to 4%, with respect to the weight of catalyst.

9. The process as defined by claim 1 , wherein the cobalt present in the catalyst comprises a Raney cobalt.

10. A process for the synthesis of β-picoline, comprising dehydrogenating the mixture of 2-methylpentamethylenediamine and 3-methylpiperidine prepared according to the process as defined in claim 1 .

11. A process for the preparation of 2-methylpentamethylenediamine and 3-methylpiperidine, comprising hydrogenating a mixture of dinitriles comprising methylglutaronitrile, ethylsuccinonitrile and adiponitrile, in the presence of a catalyst which comprises cobalt doped with nickel and chromium, under an absolute hydrogen pressure of less than 50 bar.

12. The process as defined by claim 11 , wherein the mixture of dinitriles has the following composition by weight:

Methylglutaronitrile ranging from 70% to 95%

Ethylsuccinonitrile ranging from 5% to 30%

Adiponitrile ranging from 0% to 10%.

13. The process as defined by claim 11 , wherein the mixture of dinitriles is enriched in methylglutaronitrile prior to the hydrogenation stage.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2020
From: RHODIA OPÉRATIONS
To: PERFORMANCE POLYAMIDES, SAS
Reel/Frame 051726/0747 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 29, 2010
From: MARION, PHILIPPE
To: RHODIA OPERATIONS
Reel/Frame 025218/0447 →
Priority Claims (1)
FR 08 01750 · Mar 31, 2008 · national
Continuity (1)
Related Publication 20110034693A1 · Feb 10, 2011