Process for manufacturing carboxylic acids

Patent metadata

Field	Value
Publication number	US-2024300887-A1
Application number	US-202218272658-A
Country	US
Kind code	A1
Filing date	Jan 3, 2022
Priority date	Jan 15, 2021
Publication date	Sep 12, 2024
Grant date	—

Abstract

The present invention is directed towards a process for the synthesis of compounds with the general formula (II) or their respective alkali metal salts by oxidation of compounds of general formula (I) with oxygen

in the presence of a heterogeneous catalyst containing a metal of group 10 of the periodic table of the elements,
wherein R 1 and R 2 and R 3 are same or different and selected from H and C 1 -C 6 -alkyl, non-substituted or substituted with one or more moieties selected from COOH and O-R 4 with R 4 being selected from H and C 1 -C 4 -alkyl.

First claim

1 . A process for synthesizing compounds with the general formula (II) or their respective alkali metal salts, comprising oxidizing compounds of general formula (I) with oxygen

in the presence of a heterogeneous catalyst comprising a catalytically active metal of group 10 of the periodic table of the elements, thereby obtaining a reaction mixture,
wherein R 1 and R 2 and R 3 are same or different and selected from H and C 1 -C 6 -alkyl, non-substituted or substituted with one or more moieties selected from COOH and O-R 4 with R 4 being selected from H and C 1 -C 4 -alkyl, wherein the catalytically active metal is Pt and wherein at least one promotor selected from Cd, Tl, Pb and/or Bi is present in the heterogeneous catalyst, and wherein the oxidation is carried out at a temperature in the range of from −10 to +40° C.

2 . The process according to claim 1 , wherein oxidation is carried out in an aqueous medium.

3 . The process according to claim 1 , wherein the reaction mixture comprises at least 0.9 mol of a base per mol of hydroxyl group in compound of general formula (I).

4 . The process according to claim 1 , wherein the catalytically active metal is deposited on a support.

5 . The process according to claim 1 , wherein partial pressure of oxygen during the oxidation is in the range of from 0.05 to 8 bar.

6 . The process according to claim 1 , wherein R 1 is CH 3 —CH(COOH) or HOOC—(CH 2 ) 2 —CH—COOH, as free acid or at least partially neutralized with alkali.

7 . The process according to claim 1 , wherein compound (I) has an impurity of from 0.01 to 10% by weight of glycols.

8 . The process according to claim 1 , wherein the compound of general formula (I) is a compound according to general formula (I a)

wherein R 1 is defined as above.

9 . The process according to claim 1 , wherein a reaction product comprises of compounds according to general formulae (II a) or (II b)

or the respective alkali metal salts wherein R 1 is defined as above.

10 . The process according to claim 9 , wherein the reaction product comprises compounds according to general formulae (II a) and (II b) in a molar ratio in the range of from 20:1 to 1:1 and in the range of from 2 to 15% by weight glycolic acid, referring to the sum of compounds according to general formulae (II a) and (II b).

11 . A mixture comprising compounds according to general formulae (II a) and (II b)

or their respective alkali metal salts, in a molar ratio in the range of from 2 to 15% by weight glycolic acid, referring to the sum of compounds according to general formulae (II a) and (II b), and less than 0.1% by weight of oxalic acid, or their respective alkali metal salts,
wherein R 1 is selected from H and C 1 -C 6 -alkyl, non-substituted or substituted with one or more moieties selected from COOH and O-R 4 , with R 4 being selected from H and C 1 -C 4 -alkyl and wherein the percentages refer to the respective sodium salts.

12 . The mixture according to claim 11 , wherein R 1 is CH 3 —CH(COOH) or HOOC—(CH 2 ) 2 —CH—COOH, optionally partially or fully neutralized with alkali.

Assignees

• Basf Se

Inventors

• Teles Joaquim Henrique
• Huellmann Michael
• Guthertz Alexandre
• Vautravers Nicolas
• Dodekatos Georgios
• Reinoso Garcia Marta

Classifications

• B01J23/42

  Platinum · CPC title

• C11D3/33

  Amino carboxylic acids · CPC title

• C07C229/16

  to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids · CPC title

• C07C229/12

  to carbon atoms of acyclic carbon skeletons · CPC title

• C07C227/18

  by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters · CPC title