Process for the manufacture of an amino ester

Patent metadata

Field	Value
Publication number	US-10266483-B2
Application number	US-201415037446-A
Country	US
Kind code	B2
Filing date	Nov 18, 2014
Priority date	Nov 18, 2013
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

Process for the manufacture of an amino ester of formula (I) R 1 —O—C(O)—(CH 2 ) n —NH 2 (I) in which n is an integer from 10 to 15 from an unsaturated ester responding to formula (II) R 1 —O—C(O)—(CH 2 ) m —CH═CH—R 2 (II) in which R 1 is either H or a saturated alkyl group containing from 1 to 5 carbon atoms; R 2 is either H or an alkyl group containing from 1 to 10 carbon atoms, either saturated or containing 1 or 2 unsaturations and bearing optionally a hydroxyl, a carboxylic or an ester group, and m is equal to 7, 8, 9, 10 or 11; said process comprising: submitting the unsaturated ester of formula (II) to a catalytic cross-metathesis reaction with a pentenenitrile chosen among 2-pentenenitrile or 3-pentenenitrile in order to obtain a ester-nitrile responding to formula (III) R 1 —O—C(O)—(CH 2 ) m —CH═CH—(CH 2 ) p —CN (III) in which m is equal to 7, 8, 9, 10 or 11 and p is equal to 0 or 1, and submitting the obtained ester-nitrile of formula (III) to an hydrogenation in order to obtain the amino ester of formula (I).

First claim

The invention claimed is:

1. A method for the manufacture of an ester-nitrile corresponding to formula (III)
R 1 —O—C(O)—(CH 2 ) m —CH═CH—(CH 2 ) p —CN  (III)

from an unsaturated ester responding to formula (II)
R 1 —O—C(O)—(CH 2 ) m —CH═CH—R 2   (II)

in which
R 1 is either H or a saturated alkyl group containing from 1 to 5 carbon atoms,
m is equal to 7, 9, 10 or 11, and
p is equal 1,

wherein
when m is equal to 7, R 2 is an alkyl group containing from 2 to 8 carbon atoms, either saturated or containing 1 or 2 unsaturations and bearing optionally a hydroxyl, a carboxylic or an ester group;
when m is equal to 9, R 2 is a saturated alkyl group containing from 6 to 8 carbon atoms;
when m is equal to 10, R 2 is a saturated alkyl group containing 5 carbon atoms; and
when m is equal to 11, R 2 is a saturated alkyl group containing 8 carbon atoms;

said method comprising submitting the unsaturated ester of formula (II) to a catalytic cross-metathesis reaction with 3-pentenenitrile in order to obtain the ester-nitrile responding to formula (III).

2. The method according to claim 1 , wherein the unsaturated ester of formula (II) is obtained by a reaction other than a catalytic cross-metathesis reaction.

3. The method according to claim 1 , wherein the unsaturated ester of formula (II) is obtained by a transesterification reaction using a triglyceride and an alcohol of formula R 1 OH as reagents, with R 1 as defined, and/or by a hydrolysis reaction using the triglyceride and water as reagents.

4. The method according to claim 3 , wherein the triglyceride is extracted from a vegetable oil.

5. A method for the manufacture of an amino ester of formula (I)
R 1 —O—C(O)—(CH 2 ) m —NH 2   (I)

in which R 1 is either H or a saturated alkyl group containing from 1 to 5 carbon atoms and n is an integer from 10 to 15,
said method comprising submitting the ester-nitrile of formula (III) manufactured by the method according to claim 1 to an hydrogenation in order to obtain the amino ester of formula (I).

6. The method according to claim 4 , wherein the vegetable oil is selected from the group consisting of canola, safflower, flaxseed, sunflower, corn, olive, soybean, peanut, cottonseed, palm, castor and coconut oils, and mixtures thereof.

7. A process for the manufacture of a polyamide, the process comprising
manufacturing an amino ester by the process according to the method according to claim 5 , and
manufacturing the polyamide by auto-polycondensing said amino ester.

8. The method according to claim 1 , wherein m is equal to 9, 10 or 11.

9. The method according to claim 1 , in which m is equal to 7, R1 is a saturated alkyl group containing from 1 to 5 carbon atoms and R2 is a saturated alkyl group containing 8 carbon atoms.

Assignees

• Rhodia Operations

Inventors

• Marion Philippe
• Morvan Didier

Classifications

• C07C227/04 Primary

  Formation of amino groups in compounds containing carboxyl groups · CPC title

• C07C253/30

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

• C08G69/44

  Polyester-amides · CPC title

• C07C229/08

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title

• C07C255/23

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton · CPC title