Esters of amino carboxylic acids and a process to prepare them

Patent metadata

Field	Value
Publication number	US-11629117-B2
Application number	US-201917250265-A
Country	US
Kind code	B2
Filing date	Jul 1, 2019
Priority date	Jul 3, 2018
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

The present disclosure relates to a process to prepare esters of an amino carboxylic acid of the formula (I) comprising the steps of reacting an aminocarboxylic acid present as a cyclic amide of the formula II and an alkanol of the formula R—(O-A)mOH in the presence of the Brønsted-Lowry acid at a temperature of between 60 and 200 degrees C. wherein the total molar amount of aminocarboxylic acid to the molar amount of the alkanol is between 1:0.8 and 1:1.5 and wherein the Brønsted-Lowry acid is not added to the reaction mixture until least 50% of the total of the alkanol and cyclic amide are added to the reaction mixture.

First claim

What is claimed is:

1. A process to prepare an ester, said method comprising the steps of:
reacting via ring-opening alcoholysis:
a cyclic amide chosen from caprolactam, pyrrolidine-2-one, and combinations thereof, and
an alkanol chosen from 2-ethylhexanol, isodecanol, and combinations thereof,
in the presence of a Brønsted-Lowry acid chosen from hydrochloric acid, sulfuric acid, phosphoric acid, and combinations thereof,
at a temperature of between 60 and 200° C.,

wherein the molar ratio of the alkanol to the Brønsted-Lowry acid is from about 1.01:0.3 to about 1.01:1,
wherein the total molar amount of cyclic amide to the molar amount of the alkanol is between 1:0.9 and 1:1.1,
wherein the Brønsted-Lowry acid is not added to the cyclic amide and/or alkanol until at least 50% of the total of the alkanol and cyclic amide are combined, wherein the cyclic amide and the alkanol are combined before addition of the Brønsted-Lowry acid such that a molar amount of water present in the combination to the total moles of cyclic amide in the combination is between about 0 and about 2 mole %; and
wherein the process is free of an organic solvent.

2. Process of claim 1 wherein the cyclic amide is caprolactam, the alkanol is 2-ethylhexanol, and the Brønsted-Lowry acid is hydrochloric acid.

3. Process of claim 1 wherein the cyclic amide is caprolactam, the alkanol is 2-ethylhexanol, and the Brønsted-Lowry acid is sulfuric acid.

4. Process of claim 1 wherein the cyclic amide is caprolactam, the alkanol is isodecanol, and the Brønsted-Lowry acid is sulfuric acid.

5. Process of claim 1 wherein the cyclic amide is caprolactam, the alkanol is 2-ethylhexanol, and the Brønsted-Lowry acid is phosphoric acid.

6. Process of claim 1 wherein the cyclic amide is pyrrolidine-2-one, the alkanol is 2-ethylhexanol, and the Brønsted-Lowry acid is sulfuric acid.

7. Process of claim 1 wherein the cyclic amide is caprolactam, the alkanol is or 2-ethylhexanol, and the Brønsted-Lowry acid is hydrochloric acid.

8. Process of claim 5 wherein the total molar amount of caprolactam to the molar amount of the or 2-ethylhexanol is about 1:1.

Assignees

• Nouryon Chemicals Int Bv

Inventors

• Venderbosch Rudolf Antonius Maria
• Wetzel Alexander Michael
• Schwarzmayr Louis Eckhard
• Jacobson Ingemyr Hanna Ingrid Birgitta
• Smolko Schwarzmayr Natalija

Classifications

• C07C227/22 Primary

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

• C07C229/08

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