Rhone-Poulenc Chimie

Rhodia Chimie

Christian Maliverney

Michel Gubelmann

Pascal Metivier

Philippe Denis

Isabelle Jouve

Helene Pernot

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 &ldquo;vanillin&rdquo; and ethylvanillin&rdquo;. 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.

Process for the selective preparation of a 2-hydroxybenzoic acid and a 4-hydroxybenzaldehyde and derivatives thereof

The present invention relates to a novel process for the preparation of isovanillin. The process for the preparation of isovanillin according to the invention is characterized in that it consists in dealkylation being carried out using a strong acid, selectively in the 3-position, on a 3-alkoxy-4-methoxybenzaldehyde wherein said alkoxy group has at least two carbon atoms.

Process for the preparation of isovanillin

Process for the preparation of a substituted 4-hydroxybenzaldehyde

Branched saturated dinitrile byproducts, e.g. 2-methylglutaronitrile, 2-ethylsuccinonitrile and mixtures thereof, are converted into useful ethylenic nitriles by dehydrocyanating same, in vapor phase, in the presence of an at least partially acidified cation exchange substrate, notably a molecular sieve, clay, acid oxide or lamellar phosphate.

Dehydrocyanation of aliphatic dinitriles

Optionally substituted p-aminophenol compounds, easily converted into the N-acylated derivatives thereof, are prepared by hydrogenating the corresponding nitrobenzene, in solution in a saturated aliphatic monocarboxylic acid, notably acetic acid, in the presence of an effective amount of a protonic acid.

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Lyons, France

Christian Maliverney