Process for the preparation of organosulfate salts of amino acids esters

Patent metadata

Field	Value
Publication number	US-11739052-B2
Application number	US-201917421288-A
Country	US
Kind code	B2
Filing date	Dec 18, 2019
Priority date	Jan 8, 2019
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

The present invention relates to a process for the synthesis of organosulfate salts of amino acid esters comprising the steps of reacting at least one lactam with at least 3 carbon atoms in the lactam ring with sulfuric acid in an aqueous solution followed by esterification of the reaction product of the previous step with at least 200 mol-% of at least one alcohol selected from the group consisting of linear alkyl alcohol containing one hydroxy group, branched alkyl alcohol containing one hydroxy group, linear alkylether alcohol containing one hydroxy group, branched alkylether alcohol containing one hydroxy group, phenoxyalkanols containing one hydroxy group, and mixtures thereof; followed optionally removal of water and/or removal of excess alcohol.

First claim

The invention claimed is:

1. A process for the synthesis of organosulfate salts of amino acid esters comprising the steps of
(i) reacting at least one lactam with at least 3 carbon atoms in the lactam ring with sulfuric acid in an aqueous solution, wherein the concentration of lactam in water is in the range of from 50% to 90% by weight based on the total weight of lactam and water;
(ii) esterifying the reaction product of step (i) with at least 200 mol-% of at least one alcohol selected from the group consisting of a linear alkyl alcohol containing one hydroxy group, a branched alkyl alcohol containing one hydroxy group, a linear alkylether alcohol containing one hydroxy group, a branched alkylether alcohol containing one hydroxy group, phenoxyalkanols containing one hydroxy group, and mixtures thereof; and
(iii) optionally removing water and/or removing excess alcohol of step (ii).

2. The process according to claim 1 , wherein step (i) and (ii) are carried out in one single step.

3. The process according to claim 1 , wherein the molar ratio of sulfuric acid to lactam is in the range of from 90 to 200 mol-% based on 100 mol % of the lactam.

4. The process according to claim 1 , wherein the molar ratio of alcohol containing one hydroxy group to lactam with at least 3 carbon atoms is in the range of from 200 mol-% to 400 mol-% based on 100 mol % of the lactam.

5. The process according to claim 1 , wherein the molar ratio of alcohol containing one hydroxy group to sulfuric acid is in the range of from 200 mol-% to 400 mol-% based on 100 mol % of the sulfuric acid.

6. The process according to claim 2 , wherein the combined step (i) and (ii) comprises reacting a mixture of sulfuric acid, at least one lactam and at least one alcohol at a temperature of 80 to 200° C. for 1 to 30 h.

7. The process according to claim 2 , wherein the combined step (i) and (ii) comprises reacting a mixture of sulfuric acid, at least one lactam and at least one alcohol in a closed vessel under pressure of from 1.0 up to 10.0 bar.

8. The process according to claim 1 , wherein the lactam used in step (i) is a ε-lactam.

9. The process according to claim 1 wherein the concentration of lactam in water is in the range of from 55% to 90% by weight based on the total weight of lactam and water.

10. The process according to claim 1 wherein the concentration of lactam in water is in the range of from 55% to 80% by weight based on the total weight of lactam and water.

Assignees

• Basf Se

Inventors

• Ebert Sophia
• Boeckh Dieter
• Marczewski Dawid
• Scialla Stefano
• Loughnane Brian Joseph
• Huelskoetter Frank

Classifications

• C07C227/22 Primary

  from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement · CPC title

• C07C303/24

  of esters of sulfuric acids · CPC title

• C07C229/08

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

• C07C305/04

  being acyclic and saturated · CPC title