Method for separating mandelic compounds in salified form and use of same for preparing aromatic aldehyde

Patent metadata

Field	Value
Publication number	US-9567283-B2
Application number	US-201415105047-A
Country	US
Kind code	B2
Filing date	Dec 15, 2014
Priority date	Dec 18, 2013
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

The invention describes a method for separating a mandelic compound in salified form from an aqueous reaction medium resulting from the condensation reaction of a hydroxylated aromatic compound with glyoxylic acid in a basic medium, said method comprising a) decanting said reaction medium in such a way as to recover an organic phase formed from the excess of said aromatic compound and an aqueous phase formed from said mandelic compound and a quantity of the excess of said aromatic compound and b) bringing said aqueous phase into contact with an adsorbent support, resulting in the selective adsorption of said aromatic compound and the recovery of an aqueous flow comprising said mandelic compound in salified form, which is subjected to an oxidation step before being converted into hydroxyaromatic aldehyde by electrodialysis.

First claim

The invention claimed is:

1. A process for separating at least one mandelic compound in salified form from an aqueous reaction mixture resulting from condensation, in a basic aqueous medium, of at least one aromatic compound bearing at least one hydroxyl group and in which the para position is free with glyoxylic acid, said process comprising:
a) decanting said reaction medium to recover an organic phase comprising aromatic compound in non-salified form and an aqueous phase comprising the at least one mandelic compound and an amount of the aromatic compound, each in salified form,
b) contacting said aqueous phase with an adsorbent support to selectively adsorb aromatic compound from the aqueous phase on said support and recover an aqueous mixture comprising the at least one mandelic compound in salified form.

2. The process of claim 1 , wherein said aromatic compound is selected from the group consisting of phenol and the hydroxylated aromatic compounds corresponding to formula (I):

wherein:
at least the position para to the hydroxyl group is free,
R represents a hydrogen atom or one or more identical or different substituents,
x, the number of substituents on a ring, is a number less than or equal to 4.

3. The process of claim 2 , wherein said aromatic compound corresponds to formula (I), wherein R represents a hydrogen atom, an alkyl group containing from 1 to 4 carbon atoms, or an alkoxy group containing from 1 to 4 carbon atoms, and x is equal to 1.

4. The process of claim 1 , wherein said aromatic compound is selected from the group consisting of phenol, o-cresol, m-cresol, 3-ethylphenol, 2-tert-butylphenol, guaiacol, and guaethol.

5. The process of claim 1 , wherein said organic phase obtained after decantation is recycled into the condensation reaction.

6. The process of claim 1 , wherein said step b) is performed co-currently.

7. The process of claim 1 , wherein said aqueous stream obtained after said step b) comprises a p-hydroxymandelic compound, an o-hydroxymandelic compound, and a hydroxylated dimandelic compound.

8. The process of claim 1 , further comprising desorbing said aromatic compound and recycling desorbed aromatic compound into said condensation reaction.

9. The process of claim 1 , further comprising:
acidifying said reaction mixture prior to the decanting step, and/or
acidifying said aqueous phase prior to contacting the aqueous phase with the adsorbent support.

10. The process of claim 9 , wherein acidification of said aqueous phase is effective to lower the pH of said aqueous phase 0.1 to 3 points.

11. The process of claim 9 , wherein the acidification is performed by adding strong acid or weak acid or, alternatively, by using CO 2 .

12. The process of claim 1 , further comprising:
c) oxidizing the at least one mandelic compound to at least one alkoxybenzaldehyde hydroxylate compound, and
d) converting the at least one alkoxybenzaldehyde hydroxylate compound into at least one hydroxyaromatic aldehyde.

13. The process of claim 12 , wherein said step d) comprises neutralizing the at least said alkoxybenzaldehyde hydroxylate compound into the hydroxyaromatic aldehyde and producing a saline hydroxide solution.

14. The process of claim 12 , wherein the at least one mandelic compound is selected from the group consisting of p-hydroxymandelic acid salts, 4-hydroxy-3-methoxymandelic acid salts, 3-ethoxy-4-hydroxymandelic acid salts, 4-hydroxy-3-isopropoxymandelic acid salts, and a mixture of 4-hydroxy-3-methoxymandelic and 3-ethoxy-4-hydroxymandelic acid salts.

15. The process of claim 12 , wherein said alkoxybenzaldehyde hydroxylate compound comprises a 4-hydroxy-3-methoxymandelic acid salt and the hydroxyaromatic aldehyde comprises vanillin.

16. The process as of claim 12 , wherein said alkoxybenzaldehyde hydroxylate compound comprises a 3-ethoxy-4-hydroxymandelic acid salt and the hydroxyaromatic aldehyde comprises ethylvanillin.

17. The process of claim 12 , wherein said step d) is performed by electro-electrodialysis using cation-exchange membranes.

18. The process of claim 12 , wherein said step d) is performed by electrolyzing using a two-compartment electrolyzer or a three-compartment electrolyzer.

19. The process of claim 12 , wherein said step d) is performed by bipolar membrane electrodialysis.

20. The process of claim 19 , wherein said step d) is conducted at a temperature of between 45 and 90° C.

21. The process of claim 13 , further comprising recycling said saline hydroxide solution into said step c), into said step b), and/or into said condensation reaction.

Assignees

• Rhodia Operations

Inventors

• Garel Laurent
• Normand Stephanie
• Foucher Stephanie
• Horbez Dominique
• Assam Morad

Classifications

• C07C51/41

  Preparation of salts of carboxylic acids ({C07C51/093 - C07C51/34 take precedence} preparation of soap C11D) · CPC title

• C07C51/47 Primary

  by solid-liquid treatment; by chemisorption · CPC title

• B01D15/08

  Selective adsorption, e.g. chromatography · CPC title

• C07C51/367

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C07C45/61

  by reactions not involving the formation of >C = O groups · CPC title