Process for preparing a hydroxy compound by means of decarboxylation

Patent metadata

Field	Value
Publication number	US-11319270-B2
Application number	US-201917294934-A
Country	US
Kind code	B2
Filing date	Dec 2, 2019
Priority date	Dec 7, 2018
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

The invention relates to a process for preparing a specific hydroxy compound by means of decarboxylation of a specific carboxylic acid compound or a salt of said carboxylic acid compound, to a method for preparing a diaryl carbonate, a bisphenol or a polycarbonate, a diaryl carbonate or bisphenol, a polycarbonate, and to a method for adjusting the isotope ratio of C14 to C12 in a polymer. A specific solvent is used during decarboxylation.

First claim

What is claimed is:

1. A process for producing a hydroxy compound of the formula (I)

in which
R is a linear or branched alkyl group having 1 to 6 carbon atoms,
n is 1 or 2, and
m is 0, 1, 2, or 3,

by decarboxylation of a carboxylic acid compound of the formula (II) or of a corresponding salt of said carboxylic acid compound of the formula (II)

in which R, n, and m are as defined above,

using at least one heterogeneous catalyst, wherein the at least one hydroxy compound of the formula (I) is throughout the decarboxylation reaction present in a stoichiometric excess relative to the carboxylic acid compound of the formula (II), the decarboxylation being carried out at a temperature that is above the melting temperature both of the hydroxy compound of the formula (I) that is formed and of the at least one hydroxy compound of the formula (I) used in a stoichiometric excess.

2. The process as claimed in claim 1 , wherein, before carrying out the decarboxylation reaction, the carboxylic acid compound of the formula (II) or corresponding salt of the carboxylic acid compound of the formula (II) is dissolved in the at least one hydroxy compound of the formula (I) that throughout the decarboxylation reaction is present in a stoichiometric excess relative to the carboxylic acid compound of the formula (II).

3. The process as claimed in claim 1 , wherein the at least one heterogeneous catalyst is a zeolite.

4. The process as claimed in claim 3 , wherein the zeolite has a faujasite structure.

5. The process as claimed in claim 1 , wherein the cation of the salt of the carboxylic acid compound of the formula (II) is selected from the group consisting of alkali metal cations, alkaline earth metal cations, ammonium, phosphonium, cations of manganese, iron, cobalt, nickel, copper, zinc, molybdenum, cadmium, and any desired mixtures thereof.

6. The process as claimed in claim 1 , wherein the carboxylic acid compound of the formula (II) or corresponding salt of the carboxylic acid compound of the formula (II) was obtained by fermentation or from sugars, lignocellulose, lignocellulose-containing materials, furans, and/or lignin.

7. The process as claimed in claim 1 , wherein the produced hydroxy compound of the formula (I) corresponds to the hydroxy compound of the formula (I) that throughout the decarboxylation reaction is present in a stoichiometric excess relative to the carboxylic acid compound of the formula (II).

8. The process as claimed in claim 1 , wherein the hydroxy compound of the formula (I) is phenol.

9. The process as claimed in claim 1 , wherein the carboxylic acid compound of the formula (II) or corresponding salt of the carboxylic acid compound of the formula (II) is selected from the group consisting of 2-hydroxybenzoic acid, 4-hydroxybenzoic acid, and the corresponding salts.

10. A process comprising:
(a1) executing the process as claimed in claim 1 , wherein a molar ratio of the hydroxy compound of the formula (I) that throughout the decarboxylation reaction is present in a stoichiometric excess relative to the carboxylic acid compound of the formula (II), and that is petroleum-based, to the hydroxy compound of the formula (I) as process product of the process as claimed in claim 1 is maintained.

11. A process for producing a bisphenol, wherein the process comprises:
(a2) executing the process as claimed in claim 1 for the production of a hydroxy compound of the formula (I), wherein a hydroxy compound of the formula (I) is obtained,
(b2) reacting the hydroxy compound of the formula (I) from step (a2) with a ketone or an aldehyde to afford a bisphenol.

12. A process for producing a diaryl carbonate, wherein the process comprises:
(a3) executing the process as claimed in claim 1 for the production of a hydroxy compound of the formula (I), wherein a hydroxy compound of the formula (I) is obtained,
(b3) reacting the hydroxy compound of the formula (I) from step (a3) with a carbonyl halide, with carbon monoxide or with dimethyl carbonate to afford a diaryl carbonate.

13. A process for producing a polycarbonate, wherein the process comprises:
(a4) executing the process as claimed in claim 11 for the production of a bisphenol, wherein a bisphenol is obtained,
(b4) reacting the bisphenol from step (a4) with a carbonyl halide, with carbon monoxide or with dimethyl carbonate to afford a polycarbonate.

14. A process for producing a polycarbonate, wherein the process comprises:
(a5) executing the process as claimed in claim 12 for the production of a diaryl carbonate, wherein a diaryl carbonate is obtained,
(b5) reacting the diaryl carbonate from step (a5) with a bisphenol to afford a polycarbonate.

15. A process for producing a polycarbonate, wherein the process comprises:
(a6) executing a process for the production of a bisphenol, wherein a bisphenol is obtained, the process for producing a bisphenol comprising:
(a2) executing the process as claimed in claim 1 for the production of a hydroxy compound of the formula (I), wherein a hydroxy compound of the formula (I) is obtained,
(b2) reacting the hydroxy compound of the formula (I) from step (a2) with a ketone or an aldehyde to afford a bisphenol,

(b6) executing a process for the production of a diaryl carbonate, wherein a diaryl carbonate is obtained, the process for producing a diaryl carbonate comprising:
(a3) executing the process as claimed in claim 1 for the production of a hydroxy compound of the formula (I), wherein a hydroxy compound of the formula (I) is obtained,
(b3) reacting the hydroxy compound of the formula (I) from step (a3) with a carbonyl halide, with carbon monoxide or with dimethyl carbonate to afford a diaryl carbonate,

(c6) reacting the bisphenol from step (a6) with the diaryl carbonate from step (b6) to afford a polycarbonate.

16. The process as claimed in claim 10 , wherein the polymer is a polycarbonate.

17. A process for adjusting a C14 to C12 isotope ratio in a polymer, the process comprising:
(b1) altering the molar ratio from process step (a1) as claimed in claim 10 through the addition either of a hydroxy compound of the formula (I) that is petroleum-based or of a hydroxy compound of the formula (I) obtained by fermentation or from sugars, lignocellulose, furans, and/or lignin;
(c1) producing a diaryl carbonate or bisphenol using the mixture of hydroxy compounds of the formula (I) obtained in process step (b1); and
(d1) producing the polymer using at least one diaryl carbonate and/or bisphenol from process step (c1).

18. A process as claimed in claim 17 , wherein the polymer produced in process step (d1) is a polycarbonate.

Assignees

• Covestro Intellectual Property Gmbh & Co Kg

Inventors

• Bittner Natalie
• Langanke Jens
• Meine Niklas
• Heijl Jan

Classifications

• Y02P20/141

  Feedstock · CPC title

• Y02P20/52

  using catalysts, e.g. selective catalysts · CPC title

• C07C68/04

  from carbon dioxide or inorganic carbonates · CPC title

• C07C37/50 Primary

  by reactions decreasing the number of carbon atoms (C07C37/04, C07C37/045, C07C37/055, C07C37/08 take precedence) · CPC title

• C07C39/04

  Phenol · CPC title