Process for synthesizing an amido alkyl betaine starting from an alcohol, an amido alkyl betaine prepared by the process with increased viscosity, and use thereof as a viscoelastic surfactant

Patent metadata

Field	Value
Publication number	US-10577310-B2
Application number	US-201716091205-A
Country	US
Kind code	B2
Filing date	Apr 4, 2017
Priority date	Apr 8, 2016
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

The present invention relates to a new process for synthesizing an amido alkyl betaine starting from a linear alcohol having from 8 to 22 carbon atoms, to an amido alkyl betaine prepared by the process with increased viscosity in water, and also to use thereof as a viscoelastic surfactant in oil and gas applications and home personal care applications. The present invention also relates to a process for synthesizing an amido amine starting from a linear alcohol having from 8 to 22 carbon atoms, and to an amido amine prepared by the process.

First claim

The invention claimed is:

1. A process for synthesizing an amido alkyl betaine from a linear alcohol having from 8 to 22 carbon atoms, the process comprising
a) in a first step, the linear alcohol having from 8 to 22 carbon atoms is condensed with an acrylonitrile to produce a β-alkoxy nitrile or with an alkyl acrylate to produce a β-alkoxy ester;
b) in a second step, the β-alkoxy nitrile or β-alkoxy ester obtained from step a) is reacted with a short chain alcohol having from 1 to 4 carbon atoms to produce a β-alkoxy alkyl ester;
c) in a third step, said β-alkoxy alkyl ester is reacted with an amino alkyl amine to produce an amido amine; and
d) in a fourth step, said amido amine is reacted with an alkylating agent to produce the amido alkyl betaine.

2. The process according to claim 1 , wherein in step a), the acrylonitrile or the alkyl acrylate is added to the linear alcohol having from 8 to 22 carbon atoms for a duration of from 0.5 to 4 hours at a temperature of from 10° C. to 80° C.

3. The process according claim 1 , wherein in step a), the acrylonitrile or the alkyl acrylate is added in an equivalent from 0.8 to 2.0 with respect to the linear alcohol having from 8 to 22 carbon atoms.

4. The process according to claim 1 , wherein step b) is carried out at a temperature of from 50 to 250° C. for a duration of from 0.5 to 72.0 hours.

5. The process according to claim 1 , wherein step c) is carried out at a temperature of from 90 to 150° C. for a duration of from 0.5 to 24.0 hours under an inert atmosphere.

6. The process according to claim 1 , wherein the amino alkyl amine in step c) is dimethylaminopropylamine (DMAPA).

7. The process according to claim 1 , wherein the alkylating agent in step d) is sodium monochloroacetate (SMCA).

8. The process according to claim 1 , wherein step d) is carried out at a temperature of from 60 to 90° C. for a duration of from 0.5 to 24.0 hours under an inert atmosphere.

9. The process according to claim 1 , wherein in step d), the alkylating agent is added in an equivalent from 1.0 to 2.0 with respect to the amido amine.

10. The process according to claim 1 , wherein the linear alcohol having from 8 to 22 carbon atoms is selected from the group consisting of 1-octanol, 1-decanol, 1-dodecanol, 1-tetradecanol, 1-hexadecanol, 1-octadecanol, oleyl alcohol, 1-icosanol, erucyl alcohol, 1-docosanol, and mixtures thereof.

11. A process for synthesizing an amido amine of the following general chemical formula:

wherein R is a saturated or unsaturated linear hydrocarbon radical having from 8 to 22 carbon atoms, from a linear alcohol having from 8 to 22 carbon atoms, the process comprising
a) in a first step, the linear alcohol having from 8 to 22 carbon atoms is condensed with an acrylonitrile or an alkyl acrylate to produce a β-alkoxy nitrile or a β-alkoxy ester respectively;
b) in a second step, the β-alkoxy nitrile or β-alkoxy ester obtained from step a) is reacted with a short chain alcohol having 1 to 4 carbon atoms to produce a β-alkoxy alkyl ester; and
c) in a third step, said β-alkoxy alkyl ester is reacted with DMAPA to produce the amido amine,
wherein in step a), the acrylonitrile or the alkyl acrylate is added in an equivalent from 0.8 to 2.0 with respect to the linear alcohol having from 8 to 22 carbon atoms.

12. The process according to claim 1 , wherein, in step a), the linear alcohol having from 8 to 22 carbon atoms is condensed with an acrylonitrile to produce a β-alkoxy nitrile.

13. The process according to claim 1 , wherein, in step a), the linear alcohol having from 8 to 22 carbon atoms is condensed with an alkyl acrylate to produce a β-alkoxy ester.

14. The process according to claim 12 , wherein:
in step a), the acrylonitrile is added to the linear alcohol having from 8 to 22 carbon atoms for a duration of from 0.5 to 4 hours at a temperature of from 10° C. to 80° C.,
step b) is carried out at a temperature of from 50 to 250° C. for a duration of from 0.5 to 72.0 hours,
step c) is carried out at a temperature of from 90 to 150° C. for a duration of from 0.5 to 24.0 hours under an inert atmosphere, and
step d) is carried out at a temperature of from 60 to 90° C. for a duration of from 0.5 to 24.0 hours under an inert atmosphere.

15. The process according to claim 13 , wherein:
in step a), the alkyl acrylate is added to the linear alcohol having from 8 to 22 carbon atoms for a duration of from 0.5 to 4 hours at a temperature of from 10° C. to 80° C.,
step b) is carried out at a temperature of from 50 to 250° C. for a duration of from 0.5 to 72.0 hours,
step c) is carried out at a temperature of from 90 to 150° C. for a duration of from 0.5 to 24.0 hours under an inert atmosphere, and
step d) is carried out at a temperature of from 60 to 90° C. for a duration of from 0.5 to 24.0 hours under an inert atmosphere.

Assignees

• Rhodia Operations

Inventors

• Back Olivier
• Herve Pascal
• Marion Philippe

Classifications

• C07C253/30

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

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C231/12

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

• C07C67/22

  from nitriles · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title