Process for the manufacture of an amino ester
View Patent ↗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).
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.