Rhone-poulenc Chimie

Rhodia Chimie

Rhodia Polyamide Intermediates

Pascal Metivier

Jean-Manuel Mas

Christian Maliverney

Laurent Bernard

Philippe Marion

Jean-Roger Desmurs

Philippe Denis

Jean-Pierre Simonato

Isabelle Jouve

Emmanuel Dos Santos

Harivelo Rajoharisson

Genevieve Padilla

Harivelo Rajoharison

Antoinette Gacon-Camoz

The present invention relates to a process for the preparation of &#x3b2;- or &#x3b3;-unsaturated or saturated carboxylic acids. It relates more particularly to the hydroxycarbonylation of an organic compound comprising a conjugated unsaturation, such as butadiene, by the action of carbon monoxide and water in the presence of a palladium-based catalyst. The carboxylic acids thus obtained are preferably pentenoic acids. According to the invention, the reaction medium after the end of the hydroxycarbonylation stage is treated with hydrogen to reduce the palladium present in the 2+ oxidation state to palladium in the zero oxidation state and the precipitated palladium is recovered.

Method for preparing carboxylic acids by palladium carbonylation

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

Dinitro aromatic compounds are improvedly prepared by reacting an aromatic compound with a nitric acid nitrating agent and thence separating the nitrating acid from the process stream thus formed, the process stream containing said at least one dinitro aromatic compound and also having a fraction of the nitrating acid dissolved therein, the subject process also comprising (a) distilling/stripping nitric acid from said process stream, (b) recovering nitric acid from the top of the distillation/stripping vessel and recycling same to the nitration reaction and (c) washing the process stream which contains the at least one dinitro aromatic compound, but having the nitric acid removed therefrom.

Recovering/recycling nitric acid from dinitration process streams comprising HNO3/dinitro compounds

The present invention concerns a process for the preparation of a 4-hydroxybenzaldehyde and its derivatives. More particularly, the invention concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, respectively known as vanillin and ethylvanillin. The process for the preparation of a 4-hydroxybenzaldehyde and its derivatives is characterized in that it consists of selectively oxidising, to a carboxy group, the group in the 2 position with respect to the hydroxyl group, present in the phenolic compounds in a mixture comprising at least a phenolic compound (A) carrying formyl and/or hydroxymethyl groups in the 2 and 4 position, a phenolic compound (B) carrying a formyl or hydroxymethyl group in the 4 position, a phenolic compound (C) carrying a formyl or hydroxymethyl group in the 2 position, resulting in a mixture comprising a 3-carboxy-4-hydroxybenzaldehyde, a 4-hydroxybenzaldehyde and a 2-hydroxybenzoic acid, which then undergoes a decarboxylation operation to produce the 4-hydroxybenzaldehyde and a phenol which can optionally be recycled.

Method for preparing a 4-hydroxybenzaldehyde and derivatives

Picric acid, namely, 2,4,6-trinitrophenol, is readily and effectively prepared by nitrating o-nitrophenol and/or p-nitrophenol into at least one dinitrophenol in a nitric acid medium of reaction, characteristically essentially consisting of nitric acid or immixture thereof with a strong co-acid, the at least one dinitrophenol remaining soluble in the medium of reaction, and therein completing nitration of the at least one dinitrophenol and precipitating picric acid therefrom.

Preparation of picric acid

Environmentally-polluting nitrocresol values are removed from admixtures of nitroaromatic compounds comprised thereof, notably the media of nitration of aromatic compounds by reacting same with aqueous HNO.sub.3 /H.sub.2 SO.sub.4, by first intimately contacting such nitroaromatic compound admixtures with an oxidizing agent comprising hydrogen peroxide, javelle water, or mixture thereof, and thereafter with a neutralizing agent; the nitroaromatic aromatic compounds thus purified are conveniently catalytically hydrogenated into aromatic amines.

Purification of mixtures of nitroaromatic compounds by removing

The present invention relates to a process for the preparation of carboxylic acids from unsaturated fatty acids and/or their derivatives. The process of the invention is characterized in that it comprises the following stages:

Process for the preparation of mono- and dicarboxylic acids from

Process for the preparation of 3-carboxy-4-hydroxybenzaldehides and

Process for the preparation of a substituted 4-hydroxybenzaldehyde

Optically active .alpha.-(hydroxyphenoxy)-alkanecarboxylic acids or derivatives thereof, for example D-2-(4-hydroxyphenoxy)propionic acid or lower alkyl ester thereof, are prepared by (a) saponifying an alkyl ester of an optically active .alpha.-halogeno-alkanecarboxylic acid, in an alcoholic solvent medium, by reacting same with an aqueous solution of an alkali metal hydroxide, thereby providing a solution of an alkali metal salt of an optically active .alpha.-halogeno-alkanecarboxylic acid, (b) next reacting the step (a) solution thus provided with a dihydroxybenzene or salt thereof, in the presence of an alkali metal hydroxide and in an alcoholic solvent medium, and thence (c) recovering the optically active .alpha.-(hydroxyphenoxy)-alkanecarboxylic acid or derivative thereof from the medium of reaction.

Preparation of optically active .alpha.-(hydroxyphenoxy)alkanecarboxylic

A process of preparing optically active alpha-chlorocarboxylic esters having the formula: ##STR1## from an optically active alpha-hydroxy carboxylic ester having the formula: ##STR2## in which process, an alpha-hydroxy carboxylate of formula II is brought into contact with phosgene and a compound chosen from amides, lactams and ureas, wherein R.sub.1 is an optionally substituted hydrocarbyl residue and R is preferably a methyl group.

Process of preparing optically active alpha-chlorocarboxylic esters

p-Nitrophenolic compounds, e.g., p-nitrophenol itself, are selectively prepared by (a) reacting a phenolic compound with a nitrosating agent in the presence of sulfuric acid, the concentration of which H.sub.2 SO.sub.4 being at least 60%, (b) oxidizing the p-nitrosophenolic compound thus formed with nitric acid, the concentration of sulfuric acid in the medium of reaction, upon completion of oxidation, being no greater than 80%, and (c) separating the p-nitrophenolic compound which thus precipitates.

Preparation of p-nitrophenolic compounds

A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.

Process for the preparation of brominated compounds, especially from

A process for the preparation of optically active esters of 2-chloropropionic acid of the formula: ##STR1## from an optically active lactate of the formula: ##STR2## with inversion of configuration. COOR.sub.1 in formula I and formula II is a hydrolyzable group. The lactate of formula II is brought into contact with SOCl.sub.2, followed by decomposition of the chlorosulfite formed, the process being one in which at least the decomposition stage is carried out in the presence of an ether.

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Lyons, France

Pascal Metivier