公开(公告)号：EP0946482B1

公开(公告)日：2002-07-24

申请号：EP97947095.2

申请日：1997-11-19

Applicant: RHODIA CHIMIE

Inventor： METIVIER, Pascal

IPC: C07C45/67 ,  C07C45/38 ,  C07C51/255 ,  C07C41/30 ,  C07C37/20 ,  C07C47/575 ,  C07C47/58

CPC classification number: C07C45/676 ,  C07C39/11 ,  C07C41/30 ,  C07C45/38 ,  C07C51/235 ,  C07C47/58 ,  C07C47/575 ,  C07C65/21 ,  C07C43/23

Abstract: The invention concerns a method for preparing a 4-hydroxybenzaldehyde and derivatives. More particularly it concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy-4-hydroxybenzaldehyde called 'vanillin' and 'ethylvanillin' respectively. The method for preparing a 4-hydroxybenzaldehyde and derivatives is characterised in that it consists in selectively oxidising the group in position 2 relative to the hydroxyl group, in carboxylic group, present in the phenolic compounds of a mixture containing at least: a phenolic compound (A) bearing formyl and/or hydroxymethyl groups in position 2 and 4; a phenolic compound (B) bearing a formyl or hydroxymethyl group in position 4; a phenolic compound (C) bearing a formyl or hydroxymethyl group in position 2; thus leading to a mixture containing a 3-carboxy-4-hydroxybenzaldehyde, a 4-hydroxybenzaldehyde, a 2-hydroxybenzoic acid, which is then subjected to a decarboxylation for obtaining the 4-hydroxybenzaldehyde and a phenol which can be optionally recycled.

公开(公告)号：EP0946482A1

公开(公告)日：1999-10-06

申请号：EP97947095.0

申请日：1997-11-19

Applicant: RHODIA CHIMIE

Inventor： METIVIER, Pascal

IPC: B01J23 ,  C07C37 ,  C07C39 ,  C07C41 ,  C07C43 ,  C07C45 ,  C07C47 ,  C07C51 ,  C07C65

CPC classification number: C07C45/676 ,  C07C39/11 ,  C07C41/30 ,  C07C45/38 ,  C07C51/235 ,  C07C47/58 ,  C07C47/575 ,  C07C65/21 ,  C07C43/23

Abstract: The invention concerns a method for preparing a 4-hydroxybenzaldehyde and derivatives. More particularly it concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy-4-hydroxybenzaldehyde called 'vanillin' and 'ethylvanillin' respectively. The method for preparing a 4-hydroxybenzaldehyde and derivatives is characterised in that it consists in selectively oxidising the group in position 2 relative to the hydroxyl group, in carboxylic group, present in the phenolic compounds of a mixture containing at least: a phenolic compound (A) bearing formyl and/or hydroxymethyl groups in position 2 and 4; a phenolic compound (B) bearing a formyl or hydroxymethyl group in position 4; a phenolic compound (C) bearing a formyl or hydroxymethyl group in position 2; thus leading to a mixture containing a 3-carboxy-4-hydroxybenzaldehyde, a 4-hydroxybenzaldehyde, a 2-hydroxybenzoic acid, which is then subjected to a decarboxylation for obtaining the 4-hydroxybenzaldehyde and a phenol which can be optionally recycled.

公开(公告)号：EP0934244B1

公开(公告)日：2004-12-15

申请号：EP97909401.8

申请日：1997-10-13

Applicant: RHODIA CHIMIE

Inventor： METIVIER, Pascal ,  MALIVERNEY, Christian ,  DENIS, Philippe

IPC: C07C65/05 ,  C07C51/255 ,  C07C47/565 ,  C07C45/38

CPC classification number: C07C45/38 ,  C07C51/255 ,  C07C47/565 ,  C07C65/05

Abstract: The invention concerns a method for the selective preparation of a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde and derivatives, from a mixture of two phenolic compounds, one bearing a formyl or hydroxymethyl group in position 2 and the other bearing a formyl or hydroxymethyl group in position 4. The invention also concerns the preparation of a 4-hydroxybenzaldehyde from said mixture. It concerns more particularly the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde respectively called 'vanillin' and ethyl vanillin'. The method for preparing a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde and their derivatives is characterised in that it consists in subjecting a mixture of phonemic compounds, one (A) bearing a formal or hydroxymethyl group in position 2, and the other (B) bearing a formyl or hydroxymethyl group in position 4, to selective oxidizing of the formyl or hydroxymethyl group in position 2 of compound (A) in carboxylic group, and optionally a hydroxymethyl group of compound (B) in position 4 in formyl group, thus resulting in a mixture of a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde.

公开(公告)号：EP0773919B1

公开(公告)日：2000-09-20

申请号：EP96917543.9

申请日：1996-05-24

Applicant: RHODIA CHIMIE

Inventor： METIVIER, Pascal

IPC: C07C65/30 ,  C07C51/255

CPC classification number: C07C45/676 ,  C07C45/38 ,  C07C51/255 ,  C07C47/575 ,  C07C47/58 ,  C07C65/30

Abstract: The object of the invention is a method for preparing 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof from phenol compounds bearing formyl and/or hydroxymethyl groups in positions 2 and 4. Another object of the invention is the production of 4-hydroxybenzaldehydes from 3-carboxy-4-hydroxybenzaldehydes, and particularly the production of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, known as 'vanillin' and 'ethyl vanillin' respectively. The method for preparing 3-carboxy-4-hydroxybenzaldehyde is characterised in that the group in position 2 of the phenol compound bearing formyl and/or hydroxymethyl groups in positions 2 and 4 is selectively oxidised to a carboxylic group, and optionally a hydroxymethyl group in position 4 to a formyl group. By thereafter decarboxylating the 3-carboxy-4-hydroxybenzaldehyde, a 4-hydroxybenzaldehyde is obtained.

公开(公告)号：EP0922025A1

公开(公告)日：1999-06-16

申请号：EP97933724.0

申请日：1997-07-11

Applicant: RHODIA CHIMIE

Inventor： METIVIER, Pascal

IPC: B01J31 ,  C07B43 ,  C07B61 ,  C07C201 ,  C07C205 ,  C07C207 ,  C07C227 ,  C07C229

CPC classification number: C07B43/02 ,  C07C201/00 ,  C07C201/06 ,  C07C205/60 ,  C07C207/04

Abstract: The invention concerns a method of nitrosation of a phenolic compound substituted by an electro-attracting group.The invention also concerns a method of nitration of a phenoic compound substituted by an electro-attracting group. The nitrosation method is characterised in that it consists in effecting the nitrosatio n of the said compound in presence of sulphuric acid; the concentration of the sulphuric acid being at least 60 % by weight, then optionally in effecting the separation of the resulting nitrosated compound. The invention also concerns the oxidation of the resulting p-nitrosated phenolic compound for obtaining the corresponding nitrated compound.

公开(公告)号：EP0934244A1

公开(公告)日：1999-08-11

申请号：EP97909401.0

申请日：1997-10-13

Applicant: RHODIA CHIMIE

Inventor： METIVIER, Pascal ,  MALIVERNEY, Christian ,  DENIS, Philippe

IPC: B01J23 ,  C07B61 ,  C07C45 ,  C07C47 ,  C07C51 ,  C07C65

CPC classification number: C07C45/38 ,  C07C51/255 ,  C07C47/565 ,  C07C65/05

Abstract: The invention concerns a method for the selective preparation of a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde and derivatives, from a mixture of two phenolic compounds, one bearing a formyl or hydroxymethyl group in position 2 and the other bearing a formyl or hydroxymethyl group in position 4. The invention also concerns the preparation of a 4-hydroxybenzaldehyde from said mixture. It concerns more particularly the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde respectively called 'vanillin' and ethyl vanillin'. The method for preparing a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde and their derivatives is characterised in that it consists in subjecting a mixture of phonemic compounds, one (A) bearing a formal or hydroxymethyl group in position 2, and the other (B) bearing a formyl or hydroxymethyl group in position 4, to selective oxidizing of the formyl or hydroxymethyl group in position 2 of compound (A) in carboxylic group, and optionally a hydroxymethyl group of compound (B) in position 4 in formyl group, thus resulting in a mixture of a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde.

公开(公告)号：EP0779883B1

公开(公告)日：2000-08-16

申请号：EP96904139.1

申请日：1996-02-14

Applicant: RHODIA CHIMIE

Inventor： METIVIER, Pascal ,  JOUVE, Isabelle ,  MALIVERNEY, Christian

IPC: C07C45/67 ,  C07C47/575 ,  C07C47/58 ,  C07C65/21 ,  C07C51/15 ,  C07C51/367 ,  C07C51/373

CPC classification number: C07C51/15 ,  C07C45/676 ,  C07C51/367 ,  C07C47/58 ,  C07C47/575 ,  C07C65/21

Abstract: A method for preparing a 4-hydroxybenzaldehyde having at least one substituent in the ortho position of the OH group, is disclosed. In particular, the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde is disclosed. The method for preparing a 4-hydroxybenzaldehyde which is at least 3-substituted by an alkoxy group comprises a step wherein a phenol compound which is at least 2-substituted by an alkoxy group and has positions 4 and 6 free is carboxylated in position 6 then hydroxymethylated in position 4, followed by a step of oxidising the hydroxymethyl group to a formyl group, and finally a decarboxylation step.