公开(公告)号：FR2691458A1

公开(公告)日：1993-11-26

申请号：FR9206391

申请日：1992-05-20

Applicant: RHONE POULENC CHIMIE ,  RHONE POULENC CHIMIE

Inventor： GUBELMANN MICHEL ,  GUBELMANN MICHEL ,  PERNOT HELENE ,  MALIVERNEY CHRISTIAN ,  MALIVERNEY CHRISTIAN ,  PERNOT HELENE

IPC: C07C253/30 ,  C07C255/07

Abstract: La présente invention concerne un procédé de déshydrocyanation de dinitriles aliphatiques en phase vapeur. Elle consiste plus précisément en un procédé de déshydrocyanation de dinitriles saturés, ramifiés, caractérisé en ce que des vapeurs d'un ou plusieurs desdits dinitriles saturés ramifiés sont mises en contact avec un échangeur de cation partiellement ou complètement acidifié. Les dinitriles saturés ramifiés qui sont soumis à la déshydrocyanation selon le présent procédé sont plus particulièrement le 2-méthyl-glutaronitrile, le 2-éthyl-succinonitrile, leurs mélanges entre eux ou les mélanges industriels les contenant.

公开(公告)号：DE69609806T2

公开(公告)日：2001-03-15

申请号：DE69609806

申请日：1996-02-14

Applicant: RHONE POULENC CHIMIE

Inventor： METIVIER PASCAL ,  JOUVE ISABELLE ,  MALIVERNEY CHRISTIAN

IPC: B01J27/053 ,  C07B61/00 ,  C07C45/65 ,  C07C45/67 ,  C07C47/575 ,  C07C47/58 ,  C07C51/15 ,  C07C51/353 ,  C07C51/367 ,  C07C51/373 ,  C07C65/21

Abstract: PCT No. PCT/FR96/00241 Sec. 371 Date Oct. 16, 1996 Sec. 102(e) Date Oct. 16, 1996 PCT Filed Feb. 14, 1996 PCT Pub. No. WO96/26175 PCT Pub. Date Aug. 29, 1996The subject of the present invention is a process for the preparation of a 4-hydroxybenzaldehyde carrying at least one substituent in the position ortho to the OH group. It more particularly relates to the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy-4-hydroxybenzaldehyde. The process for the preparation of a substituted 4-hydroxybenzaldlehyde, substituted at least in the 3 position by an alkoxy group, is characterized in that it comprises subjecting a substituted phenol compound, substituted at least in the 2 position by an alkoxy group and in which the 4 and 6 positions are free, to a first stage of carboxylation in the 6 position, then to a stage of hydroxymethylation in the 4 position, followed by a stage of oxidation of the hydroxymethyl group to a formyl group, and finally to a last decarboxylation stage.\!

公开(公告)号：ZA979177B

公开(公告)日：1998-05-21

申请号：ZA979177

申请日：1997-10-14

Applicant: RHONE POULENC CHIMIE

Inventor： DENIS PHILIPPE ,  MALIVERNEY CHRISTIAN ,  METIVIER PASCAL

IPC: C07B61/00 ,  B01J23/644 ,  C07C45/38 ,  C07C47/565 ,  C07C47/575 ,  C07C47/58 ,  C07C51/255 ,  C07C65/05 ,  C07C

Abstract: The present invention concerns a process for the preparation of a 2-hydroxybenzoic acid and of a 4-hydroxybenzaldehyde and derivatives thereof from a mixture of two phenolic compounds, one carrying a formyl or hydroxymethyl group in the 2 position, and the other carrying a formyl or hydroxymethyl group in the 4 position. The invention also concerns the preparation of a 4-hydroxybenzaldehyde from said mixture. The invention more particularly concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy4-hydroxybenzaldehyde, respectively known as "vanillin" and ethylvanillin". The process for the preparation of a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde and derivatives thereof is characterised in that the formyl or hydroxymethyl group in the 2 position of compound (A) in a mixture of phenolic compounds, one (A) carrying a formyl or hydroxymethyl group in the 2 position, and the other (B) carrying a formyl or hydroxymethyl group in the 4 position, is selectively oxidised to a carboxy group and optionally a hydroxymethyl group of compound (B) in the 4 position is selectively oxidised to a formyl group, thus producing a mixture of a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde.

公开(公告)号：FR2725982A1

公开(公告)日：1996-04-26

申请号：FR9412661

申请日：1994-10-24

Applicant: RHONE POULENC CHIMIE

Inventor： MALIVERNEY CHRISTIAN

IPC: C07C45/64 ,  C07C45/67 ,  C07C45/71 ,  C07C47/575 ,  C07C45/61

Abstract: Prepn. of isovanillin comprises selective dealkylation in position 3 of a 3-alkoxy-4-methoxybenzaldehyde with a strong acid, the alkoxy gps. contg. at least 2C. The strong acid has a pKa of ≤ 3 and is pref. a halogenic acid, an opt. halogenated oxyacid or an opt. halogenated sulphonic acids. The alkylating agent is a halomethyl, pref. CH3Cl or dimethylsulphate. The 3-alkoxy-4-methoxy-benzaldehyde is prepd. by O-methylation of the corresp. 4-hydroxy cpd. at 80-95 degrees C and at a pH of 9, by addn. of an aq. alkali metal base, partic. sodium hydroxide, carbonate or hydrogencarbonate. The 4-hydroxy deriv. is pref. treated with a basic soln., the temp. is then adjusted, the alkylating agent and an optional base are added and the organic phase is recovered and separated. Both reaction steps are carried out under inert gas, pref. a noble gas or N2. In the dealkylation step, . 95-99 wt.% H2SO4 or 30-50 wt.% HCl or HBr is used, and in an acid to 3-alkoxy-4-methoxybenzaldehyde molar ratio of 4-10.

公开(公告)号：NO954227D0

公开(公告)日：1995-10-23

申请号：NO954227

申请日：1995-10-23

Applicant: RHONE POULENC CHIMIE

Inventor： MALIVERNEY CHRISTIAN

IPC: C07C45/64 ,  C07C45/67 ,  C07C45/71 ,  C07C47/575 ,  C07C

Abstract: Prepn. of isovanillin comprises selective dealkylation in position 3 of a 3-alkoxy-4-methoxybenzaldehyde with a strong acid, the alkoxy gps. contg. at least 2C. The strong acid has a pKa of ≤ 3 and is pref. a halogenic acid, an opt. halogenated oxyacid or an opt. halogenated sulphonic acids. The alkylating agent is a halomethyl, pref. CH3Cl or dimethylsulphate. The 3-alkoxy-4-methoxy-benzaldehyde is prepd. by O-methylation of the corresp. 4-hydroxy cpd. at 80-95 degrees C and at a pH of 9, by addn. of an aq. alkali metal base, partic. sodium hydroxide, carbonate or hydrogencarbonate. The 4-hydroxy deriv. is pref. treated with a basic soln., the temp. is then adjusted, the alkylating agent and an optional base are added and the organic phase is recovered and separated. Both reaction steps are carried out under inert gas, pref. a noble gas or N2. In the dealkylation step, . 95-99 wt.% H2SO4 or 30-50 wt.% HCl or HBr is used, and in an acid to 3-alkoxy-4-methoxybenzaldehyde molar ratio of 4-10.

公开(公告)号：NO308991B1

公开(公告)日：2000-11-27

申请号：NO954227

申请日：1995-10-23

Applicant: RHONE POULENC CHIMIE

Inventor： MALIVERNEY CHRISTIAN

IPC: C07C45/64 ,  C07C45/67 ,  C07C45/71 ,  C07C47/575

Abstract: Prepn. of isovanillin comprises selective dealkylation in position 3 of a 3-alkoxy-4-methoxybenzaldehyde with a strong acid, the alkoxy gps. contg. at least 2C. The strong acid has a pKa of ≤ 3 and is pref. a halogenic acid, an opt. halogenated oxyacid or an opt. halogenated sulphonic acids. The alkylating agent is a halomethyl, pref. CH3Cl or dimethylsulphate. The 3-alkoxy-4-methoxy-benzaldehyde is prepd. by O-methylation of the corresp. 4-hydroxy cpd. at 80-95 degrees C and at a pH of 9, by addn. of an aq. alkali metal base, partic. sodium hydroxide, carbonate or hydrogencarbonate. The 4-hydroxy deriv. is pref. treated with a basic soln., the temp. is then adjusted, the alkylating agent and an optional base are added and the organic phase is recovered and separated. Both reaction steps are carried out under inert gas, pref. a noble gas or N2. In the dealkylation step, . 95-99 wt.% H2SO4 or 30-50 wt.% HCl or HBr is used, and in an acid to 3-alkoxy-4-methoxybenzaldehyde molar ratio of 4-10.

公开(公告)号：FR2742335A1

公开(公告)日：1997-06-20

申请号：FR9514762

申请日：1995-12-13

Applicant: RHONE POULENC CHIMIE

Inventor： STORET ISABELLE ,  MALIVERNEY CHRISTIAN

IPC: C11B9/00 ,  C11D3/50 ,  A61K7/46

Abstract: A method for preparing fragrance compositions, the uses thereof and the resulting products, are disclosed. Specifically, the method is useful for preparing fragrance compositions and fragrant substances and products for use in perfumes, and comprises adding an effective amount of 3-n-propoxy-4-hydroxybenzaldehyde and/or 3-isopropoxy-4-hydroxybenzaldehyde to the usual components of such compositions, substances and finished products.

公开(公告)号：FR2730730B1

公开(公告)日：1997-04-04

申请号：FR9501926

申请日：1995-02-20

Applicant: RHONE POULENC CHIMIE

Inventor： METIVIER PASCAL ,  MALIVERNEY CHRISTIAN ,  JOUVE ISABELLE

IPC: B01J27/053 ,  C07B61/00 ,  C07C45/65 ,  C07C45/67 ,  C07C47/575 ,  C07C47/58 ,  C07C51/15 ,  C07C51/353 ,  C07C51/367 ,  C07C51/373 ,  C07C65/21

Abstract: PCT No. PCT/FR96/00241 Sec. 371 Date Oct. 16, 1996 Sec. 102(e) Date Oct. 16, 1996 PCT Filed Feb. 14, 1996 PCT Pub. No. WO96/26175 PCT Pub. Date Aug. 29, 1996The subject of the present invention is a process for the preparation of a 4-hydroxybenzaldehyde carrying at least one substituent in the position ortho to the OH group. It more particularly relates to the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy-4-hydroxybenzaldehyde. The process for the preparation of a substituted 4-hydroxybenzaldlehyde, substituted at least in the 3 position by an alkoxy group, is characterized in that it comprises subjecting a substituted phenol compound, substituted at least in the 2 position by an alkoxy group and in which the 4 and 6 positions are free, to a first stage of carboxylation in the 6 position, then to a stage of hydroxymethylation in the 4 position, followed by a stage of oxidation of the hydroxymethyl group to a formyl group, and finally to a last decarboxylation stage.\!

公开(公告)号：FR2725982B1

公开(公告)日：1996-12-20

申请号：FR9412661

申请日：1994-10-24

Applicant: RHONE POULENC CHIMIE

Inventor： MALIVERNEY CHRISTIAN

IPC: C07C45/64 ,  C07C45/67 ,  C07C45/71 ,  C07C47/575 ,  C07C45/61

Abstract: Prepn. of isovanillin comprises selective dealkylation in position 3 of a 3-alkoxy-4-methoxybenzaldehyde with a strong acid, the alkoxy gps. contg. at least 2C. The strong acid has a pKa of ≤ 3 and is pref. a halogenic acid, an opt. halogenated oxyacid or an opt. halogenated sulphonic acids. The alkylating agent is a halomethyl, pref. CH3Cl or dimethylsulphate. The 3-alkoxy-4-methoxy-benzaldehyde is prepd. by O-methylation of the corresp. 4-hydroxy cpd. at 80-95 degrees C and at a pH of 9, by addn. of an aq. alkali metal base, partic. sodium hydroxide, carbonate or hydrogencarbonate. The 4-hydroxy deriv. is pref. treated with a basic soln., the temp. is then adjusted, the alkylating agent and an optional base are added and the organic phase is recovered and separated. Both reaction steps are carried out under inert gas, pref. a noble gas or N2. In the dealkylation step, . 95-99 wt.% H2SO4 or 30-50 wt.% HCl or HBr is used, and in an acid to 3-alkoxy-4-methoxybenzaldehyde molar ratio of 4-10.

公开(公告)号：ES2092793T3

公开(公告)日：1996-12-01

申请号：ES93420184

申请日：1993-05-07

Applicant: RHONE POULENC CHIMIE

Inventor： GUBELMANN MICHEL ,  MALIVERNEY CHRISTIAN ,  PERNOT HELENE

IPC: C07C253/30 ,  C07C255/07

Abstract: The present invention relates to a process for the dehydrocyanation of aliphatic dinitriles in the vapour phase. More precisely, it consists of a process for the dehydrocyanation of branched, saturated dinitriles, characterised in that vapours of one or more of the said branched, saturated dinitriles are brought into contact with a partially or completely acidified cation exchanger. The branched, saturated dinitriles which are subjected to the dehydrocyanation according to the present process are more particularly 2-methylglutaronitrile, 2-ethylsuccinonitrile, their mixtures with each other or industrial mixtures containing them.