Organic sulfonic acid salts of amino acid esters and process for their preparation

Patent metadata

Field	Value
Publication number	US-11780802-B2
Application number	US-201816770080-A
Country	US
Kind code	B2
Filing date	Nov 27, 2018
Priority date	Dec 5, 2017
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

Abstract

The application relates to a process for the synthesis of organic sulfonic acid 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 at least one organic sulfonic acid in an aqueous solution, (ii) esterification of the organic sulfonic amino acid salt of step (i) with at least one alcohol with at least 8 carbon atoms comprising at least one hydroxyl group, (iii) optionally removal of water and/or removal of excess alcohol of step (ii). The application also relates to organic sulfonic acid salts of amino acid esters of the general formula (I).

First claim

The invention claimed is:

1. Process for the synthesis of organic sulfonic acid 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 at least one organic sulfonic acid in an aqueous solution,
(ii) esterification of the reaction product of step (i) with at least one alcohol with at least 8 carbon atoms comprising at least one hydroxyl group,
(iii) optionally removal of water and/or removal of excess alcohol of step (ii);
wherein the aqueous solution has a molar ratio of water to the at least one lactam of at least 2.33:1.

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

3. Process according to claim 1 , wherein the molar ratio of organic sulfonic acid to lactam is in the range of from 90 to 200 mol-%.

4. Process according to claim 2 , wherein the combined step (i) and (ii) comprises reacting a mixture of organic sulfonic acid, at least one lactam with at least 3 carbon atoms in the lactam ring and at least one linear or branched C 8 - to C 36 -alcohol comprising at least one hydroxyl group at a temperature of 80 to 200° C. for 1 to 30 h.

5. Process according to claim 1 , wherein the molar ratio of organic sulfonic amino acid salt reaction product of step (i) to hydroxyl groups of the at least one alcohol is in the range of from 50 to 125 mol-% in case a monoalcohol is used in step (ii).

6. Process according to claim 1 , wherein the molar ratio of organic sulfonic amino acid salt reaction product of step (i) to hydroxyl groups of the at least one alcohol is in the range of from 10 to 125 mol-% in case a di- or polyalcohol is used in step (ii).

7. Process according to claim 1 , wherein the alcohol used in step (ii) is selected from the group consisting of mono-alcohols, diols, polyols, alkoxylated mono-alcohols, alkoxylated diols, and alkoxylated polyols.

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

9. Process according to claim 1 , wherein the organic sulfonic acid is selected from the group consisting of dodecylbenzene sulfonic acid, p-toluene sulfonic acid, xylene sulfonic acid, and methanesulfonic acid.

10. Process according to claim 1 , wherein the organic sulfonic acid is methanesulfonic acid.

11. Process for the synthesis of organic sulfonic acid 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 at least one organic sulfonic acid in an aqueous solution,
(ii) esterification of the reaction product of step (i) with at least one alcohol with at least 8 carbon atoms comprising at least one hydroxyl group,
(iii) optionally removal of water and/or removal of excess alcohol of step (ii);
wherein the at least one organic sulfonic acid is not p-toluene sulfonic acid; and wherein the aqueous solution has a molar ratio of water to the at least one lactam of at least 2.33:1.

12. The process according to claim 1 , wherein the aqueous solution has a molar ratio of water to the at least one lactam of 2.33:1 to 5:1.

Assignees

• Basf Se

Inventors

• Ebert Sophia
• Ludolph Bjoern
• Marczewski Dawid

Classifications

• C07C227/22 Primary

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

• C07C303/22

  from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups} · CPC title

• C07C309/30

  of six-membered aromatic rings substituted by alkyl groups · CPC title

• C07C229/08

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

• C07C309/04

  containing only one sulfo group · CPC title