Produits Chimiques Ugine Kuhlmann

Atochem

P C U K Produits Chimiques Ugine Kuhlmann

Other

Elf Atochem S.a.

Pierre Tellier

Jean-Pierre Schirmann

Francis Weiss

Henri Mathais

Serge Y Delavarenne

Bertrand Collier

Michel Devic

Bernard Dubreux

Gerard Krempf

Jean-Pierre Pleuvry

Lucien E Bourson

Serge-Yvon Delavarenne

Azines, e.g., ketazines, are continuously produced by (i) establishing a loop having an azine reaction medium circulating therein, such loop including an azine reaction zone, means for separating azine final product from the circulating reaction medium, means for heating the reaction medium and for purging water therefrom, and means for recycling heated and purged reaction medium to the azine reaction zone, (ii) introducing hydrogen peroxide, ammonia and a carbonyl compound into the circulating reaction medium in the azine reaction zone, (iii) withdrawing azine final product thus formed from the circulating reaction medium. downstream of the azine reaction zone, (iii) thereafter purging water from the circulating reaction medium to maintain the volume thereof essentially constant, (iv) heating the circulating reaction medium to a temperature of at least 130&deg; C., (v) recycling thus heated reaction medium to the azine reaction zone, and (vi), at any point along the loop, introducing a reagent into the circulating reaction medium as to essentially maintain the equilibrium of the azine-forming reaction; the final product azines are conveniently hydrolyzed into hydrazine hydrate.

Continuous production of azines/hydrazine hydrate

Solutions of hydrazine hydrate are vaporized, without any concomitant decomposition thereof, by heating such solutions, in the liquid phase, under conditions as to effect the decompression or volatilization thereof; this process is particularly applicable for the vaporization of that hydrazine hydrate solution contained in the reboiler of a column wherein the hydrolysis of an azine R.sub.1 R.sub.2 C.dbd.N-N.dbd.CR.sub.1 R.sub.2 is carried out, with recovery of hydrazine hydrate at the base of the column and of a ketone, R.sub.1 R.sub.2 C.dbd.O, at the column head.

Vaporization of solutions of hydrazine hydrate

The acyl cyanides (nitriles) are prepared by reacting an acid halide with an alkali metal cyanide, in the presence of an alkylene oxide compound and a catalytically effective amount of water.

Synthesis of acyl cyanides in a hydrous reaction medium

The acyl cyanides (nitriles), notably benzoyl cyanide, are prepared by reacting an acid halide with an alkali metal cyanide, in an anhydrous solvent medium, in the presence of an alkylene oxide compound and a polar compound other than water, e.g., glycerol, ethylene glycol, formamide or a sugar derivative.

Synthesis of acyl cyanides in an anhydrous reaction medium

Azines, well suited for hydrolysis into hydrazine, are prepared in high yields by reacting ammonia, aqueous hydrogen peroxide and a carbonyl compound reactant in the presence of a catalytically effective amount of a catalyst medium therefor, i.e., an aqueous solution of ammonium acetate and acetamide or of acetamide and acetic acid, but in the absence of CO.sub.2.

Azine synthesis in the absence of CO.sub.2

Azines are synthesized from aqueous hydrogen peroxide, ammonia and a carbonyl compound, e.g., acetone, methyl ethyl ketone or methyl isobutyl ketone, in the presence of a catalytically effective amount of immixture of an amide of a weak acid and an ammonium salt corresponding to such weak acid. A more general high output such process comprises (a) interreacting aqueous hydrogen peroxide, ammonia and a carbonyl compound in the presence of a catalytically effective amount of immixture comprising an amide of a weak acid, (b) separating the azine thus produced from the medium of reaction, (c) reconstituting the amount of the amide in the medium of reaction to the initial amount thereof present at the onset of step (a), and (d) recycling such reconstituted medium of reaction to step (a).

Catalytic synthesis of azines from H.sub.2 O.sub.2 /NH.sub.3 /carbonyl

Process for cooking lignocellulosic materials by heating the said materials in a cooking solution containing caustic soda with or without an alkali metal sulphide, in which the solution used contains about 0.01% to 10%, preferably 0.05% to 2%, by weight of 1,2,3,4-tetrahydro-9,10-anthracenediol based on the weight of the dry lignocellulosic material.

Process for cooking lignocellulosic materials intended for the

A process for the preparation of 1,2,3,4-tetrahydro-9,10-anthracene-diol, in which catalytic hydrogenation of 1,4,4a,9a-tetrahydro-anthraquinone is carried out in the liquid phase to give 1,2,3,4,4a,9a-hexahydro-9,10-anthracene-dione followed by isomerization of the latter in the presence of an acid to give 1,2,3,4-tetrahydro-9,10-anthracene-diol.

Process for the preparation of 1,2,3,4-tetrahydro-9,10-anthracene-diol

Process for the preparation of the mononitro derivatives substituted in positions 5 or 6 of 1,2,3,4-tetrahydro-anthraquinone, which comprises nitrating 1,2,3,4,4a,9a-hexahydro-9,10-anthracene-dione by means of nitric acid or a mixture of nitric acid and sulfuric acid.

Process for the preparation of the 5- and 6-nitro derivatives of

5-amino-1,2,3,4-tetrahydroanthraquinone, as a new industrial product, is disclosed together with its preparation by reduction from 5-nitro-1,2,3,4-tetrahydroanthraquinone.

5-Amino-1,2,3,4-tetrahydroanthraquinone and its preparation

A process is disclosed for the preparation of mononitro derivatives of 1,2,3,4-tetrahydro-anthraquinone from 1,4,4a,9a-tetrahydro-anthraquinone, in which a thermal pretreatment of the 1,4,4a,9a-tetrahydro-anthraquinone is carried out in the presence of a hydrogenation catalyst in an inert atmosphere and in the absence of oxidizing or reducing agents, the anthraquinone by-produced as well as the catalyst are separated and the mixture of 1,2,3,4-tetrahydro-9,10-anthracenediol and 1,2,3,4-tetrahydro-anthraquinone obtained is subjected to a nitration reaction.

Process for the preparation of mononitro-1,2,3,4-tetrahydroanthraquinones

A new industrial product, namely 1,2,3,4,4a,9a-hexahydro-9,10-anthracene-dione, is disclosed together with a process for its preparation and its use in conventional alkali metal hydroxide cook or Kraft cook processes for the delignification of lignocellulose materials.

1,2,3,4,4a,9a-Hexahydro-9,10-anthracene-dione, its preparation and its

This invention relates to a method for preparing oxaziridines which comprises reacting hydrogen peroxide with an azomethinic derivative or with a mixture of a carbonyl compound and a primary amine in the presence of catalytic amounts of selenium or of oxygenated compounds of selenium.

Process for the preparation of oxaziridine

A process which comprises reacting 1,4,4a,5,8,8a,9a,10a-octahydro-anthraquinone with nitrobenzene in the presence of a catalytic amount of a basic compound soluble in the reaction medium and of an inhibitor of free radical reactions to produce anthraquinone.

Process for the preparation of anthraquinone

This invention relates to a method for preparing an azine of the formula ##EQU1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent a hydrogen atom or a straight alkyl radical of from 1 to 12 carbon atoms, a branched alkyl or cycloalkyl radical of 3 to 12 carbon atoms, or a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene, naphthalene, or pyridine aromatic ring or R.sub.1 and R.sub.2 together form a straight or branched alkylene radical of 3 to 11 carbon atoms, one of which may be replaced by an oxygen atom, all of the above being unsubstituted or substituted with chlorine, bromine, or fluorine atoms, or ethylene, nitro, hydroxy, alkoxy, carboxylic or percarboxylic acid, amide, nitrile, or carboxylic ester groups, or a mixture of an azine of formula (I) and a hydrazone of the formula ##EQU2## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.3 and R.sub.4, which may be the same or different, represent a straight alkyl radical of from 1 to 12 carbon atoms, a branched alkyl or cycloalkyl radical of 3 to 12 carbon atoms, or a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene, naphthalene, or pyridine aromatic ring or R.sub.1 and R.sub.2 together form a straight or branched alkylene radical of 3 to 11 carbon atoms, one of which may be replaced by an oxygen atom, all of the above being unsubstituted or substituted by chlorine, bromine, fluorine, or iodine atoms, or hydroxy, ether oxide, carboxylic acid, carboxylic ester, nitrile, nitro, or sulphonic acid or amide groups or one of the two radicals R.sub.3 and R.sub.4 can represent a hydrogen atom, which comprises reacting hydrogen peroxide with ammonia or with a mixture of ammonia and primary or secondary amine of the formula ##EQU3## wherein R.sub.3 and R.sub.4 are as defined above, in the presence of a carbonyl compound of the formula ##EQU4## wherein R.sub.1 and R.sub.2 are as defined above, and a catalyst containing selenium.

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Oullins, France

Pierre Tellier