Process for preparing mandelic aromatic compounds and aromatic aldehyde compounds

Patent metadata

Field	Value
Publication number	US-2016297735-A1
Application number	US-201415036871-A
Country	US
Kind code	A1
Filing date	Nov 14, 2014
Priority date	Nov 15, 2013
Publication date	Oct 13, 2016
Grant date	—

Abstract

A process for preparing an aromatic compound or compounds where at least one mandelic group —CHOH—COOH is described, comprising a reaction for condensation of at least one aromatic compound with glyoxylic acid or derivatives thereof, wherein said condensation reaction is carried out substantially in the absence of any acid or any base added to the reaction medium. The condensation reaction is followed by an oxidation reaction in order to obtain aromatic aldehyde.

First claim

1 . A process for the preparation of one or more mandelic aromatic compounds comprising reacting at least one aromatic compound with glyoxylic acid or its derivatives under condensation conditions substantially in the absence of any added acid or added base.

2 . The process of claim 1 , wherein the at least one aromatic compound is selected from the group consisting of substituted benzenes, phenol, substituted phenols, heterocyclic aromatic compounds, and polycyclic aromatic compounds.

3 . The process of claim 2 , wherein the substituted phenols are according to formula (I):

wherein:
R represents one or more identical or different substituents,
x, the number of substituents on a ring, is an integer between 1 and 4,
when x is greater than 1, two R groups placed on two vicinal carbon atoms can form, together and with the carbon atoms which carry them, a saturated, unsaturated, or aromatic ring having from 5 to 7 atoms and optionally comprising one or more heteroatoms.

4 . The process of claim 3 , wherein the position para with respect to the hydroxyl group of the substituted phenol according to formula (I) is unsubstituted.

5 . The process of claim 3 , wherein the substituted phenols are selected from the group consisting of o-cresol, m-cresol, 3-ethylphenol, 2-(tert-butyl)phenol, guaiacol, and guaethol.

6 . The process of claim 1 , wherein the glyoxylic acid is in the monohydrate form.

7 . The process of claim 1 , wherein the step of reacting is carried out in the presence of at least one catalyst.

8 . The process of claim 7 , wherein the catalyst is selected from transition metal complexes comprising oxygen-comprising ligands.

9 . The process of claim 7 , wherein the catalyst is selected from the group consisting of: iron(II) acetate, iron(III) acetate, copper(II) acetate, iron(II) acetylacetonate, iron(III) acetylacetonate, copper(II) acetylacetonate, and copper(III) acetylacetonate.

10 . The process of claim 7 , wherein the catalyst comprises a complex composed of a transition metal and at least one glyoxylate ligand.

11 . The process claim 1 , wherein the step of reacting is carried out in the presence of a solvent selected from the group consisting of water, aromatic hydrocarbons, alcohols, and a water-alcohol mixtures.

12 . The process of claim 1 , wherein the step of reacting is carried out in the absence of a solvent.

13 . The process of claim 1 , wherein the at least one aromatic compound and glyoxylic acid or its derivatives are in a molar ratio of about 1.

14 . The process of claim 1 , wherein the process consists of reacting the glyoxylic acid with guaiacol, with guaethol, or with guaiacol and guaethol.

15 . A process for the preparation of one or more mandelic aromatic aldehydes comprising reacting at least one aromatic compound with glyoxylic acid or a derivative thereof according to the process of claim 1 to prepare one or more mandelic aromatic compounds, and oxidizing the one or more mandelic aromatic compounds.

16 . The process of claim 15 , wherein the step of oxidizing is carried out without addition of alkaline agent.

17 . The process of claim 15 , wherein the step of oxidizing is carried out in the presence of water as solvent.

18 . The process claim 15 , wherein the step of oxidizing is carried out in the presence of a catalyst selected from the group consisting of chromium, cobalt, copper, vanadium, manganese, iron, nickel and osmium derivatives.

19 . The process of claim 15 , the one or more aromatic aldehydes comprise vanillin, ethylvanillin, or vanillin and ethylvanillin.

20 . A process for the preparation of one or more aromatic aldehydes by oxidizing one or more mandelic aromatic compounds, in the presence of at least one oxidizing agent and of at least one catalyst and substantially in the absence of any added acid or added base.

21 . The process of claim 20 , wherein the one or more mandelic aromatic compounds are obtained by reacting at least one aromatic compound with glyoxylic acid or its derivatives, under condensation conditions in the presence of added acid or base or substantially in the absence of any added acid or added base added.

22 . A process for the preparation of one or more mandelic aromatic compounds, comprising reacting at least one aromatic compound with glyoxylic acid or its derivatives under condensation conditions in the absence of solvent and wherein the glyoxylic acid is glyoxylic acid monohydrate.

23 . A process for the preparation of one or more mandelic aromatic compounds, comprising reacting at least one aromatic compound with glyoxylic acid or its derivatives under condensation conditions in the presence of at least one catalyst chosen from transition metal complexes comprising oxygen-comprising ligands.

24 . A process, comprising reacting an organic compound and a carbonyl compound under condensation conditions in the presence of a catalyst selected from the group consisting of transition metal complexes comprising oxygen-comprising ligands, compounds based on rare earth metals, zeolites, clays, lanthanum phosphate, metal oxides, and metal hydroxides substantially in the absence of any added acid or added base without bringing about the coproduction of a simple molecule.

Assignees

• Rhodia Operations

Inventors

• Garel Laurent
• Sarrazin Flavie
• Back Olivier
• Olivon Kevin
• Pucheault Mathieu

Classifications

• C07C51/367 Primary

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

• C07C47/58

  Vanillin · CPC title

• C07C47/575

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C45/39

  being a secondary hydroxyl group · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title