Hoechst Aktiengesellschaft

Hoechst Aktiengesell

Erwin Weiss

Hans-Jerg Kleiner

Herbert Siegel

Harald Berger

Manfred Finke

Walter Rupp

A compound of the formula I, ##STR1## in which X is F, Cl or Br,

Process for the preparation of bifunctional tertiary aromatic phosphine

Tertiary aromatic phosphine oxides of the formula ##STR1## in which X=F, Cl or Br, are prepared by Friedel-Crafts reaction of (a) phenylthiophosphonic dichloride with fluoro-, chloro-or bromobenzene, or

Tertiary phosphine oxides are prepared by oxidation of tertiary phosphine sulfides using H.sub.2 O.sub.2 in a solvent comprising about 2-20% by weight of optionally halogenated lower aliphatic carboxylic acids and the remainder of mono- or polyhydric aliphatic or cycloaliphatic alcohols--if appropriate in mixtures with other inert solvents which are miscible with the carboxylic acid/alcohol mixture. Preferred solvents comprise acetic acid/methanol and acetic acid/ethanol mixtures. The reaction products are final products and intermediates products in various specialized fields such as, for example, the plant protection sector and the polymers sector.

Process for the preparation of tertiary phosphine oxides

The invention relates to a process for the preparation of vinylphosphonic dichloride through elimination of hydrogen chloride from 2-chloroethanephosphonic dichloride in the presence of catalysts. The catalysts used are tertiary phosphines, quaternary ammonium or phosphonium salts or alkali metal or alkaline-earth metal halides. When triphenyl phosphine is used as the catalyst, the reaction is carried out under reduced pressure at a temperature of 130.degree. to 166.degree. C. and the vinylphosphonic dichloride produced is simultaneously removed by distillation under reduced pressure. When the other catalysts are used, the process can be carried out at atmospheric pressure or reduced pressure and at temperatures of about 130.degree. to 220.degree. C. and the vinylphosphonic dichloride produced can be removed by distillation simultaneously with or subsequent to the reaction.

Process for the preparation of vinylphosphonic dichloride

The invention relates to a process for the preparation of vinylphosphonic dichloride, in which a 2-chloroethanephosphonate of the formula ##STR1## or a mixture of the two esters, is reacted with thionyl chloride at a temperature of 60.degree. to 160.degree. C. in the presence of a catalyst which contains tertiary phosphines, quaternary ammonium or phosphonium salts or alkali metal or alkaline-earth metal halides. During this reaction, any thionyl chloride which may be present is removed by distillation subsequent to this reaction, the mixture remaining is heated to 140.degree. to 200.degree. C., and the vinylphosphonic dichloride produced during this is removed by distillation.

The invention relates to a process for the preparation of 2-chloroethanephosphonic dichloride through reaction of a 2-chloroethanephosphonate of the formula ##STR1## or a mixture of the two esters, with thionyl chloride at a temperature of 60.degree. to 160.degree. C. In this reaction, tertiary phosphines, quaternary ammonium or phosphonium salts or alkali metal or alkaline-earth metal halides are employed as catalysts. The thionyl chloride is introduced into the initially introduced ester.

Process for the preparation of 2-chloroethanephosphonic dichloride

Tertiary phosphine oxides are prepared by the oxidation of tertiary phosphine sulfides with H.sub.2 O.sub.2 in a solvent composed of at least about 20% by weight, preferably at least about 50% by weight, of optionally halogenated, lower aliphatic carboxylic acids and/or their anhydrides; it is particularly preferred if the solvent is composed only of acetic acid. The reaction products are end products and intermediates in a variety of areas such as, for example, the sectors of plant protection and polymers.

Tertiary aromatic phosphine sulfides of the formula ##STR1## wherein X=F, Cl or Br, are prepared by means of a Friedel-Crafts reaction of

2-(Meth)acrylamido-2-methylpropanephosphonic acid is prepared by reaction of 2-methylprop-1-ene-1-phosphonic acid or 2-methylpro-2-ene-1-phosphonic acid with (meth)acrylonitrile in the presence of an equimolar amount of a strong acid. The compounds are suitable as such or in the form of their salts as comonomer for the manufacture of copolymers, which are used inter alia as dyeing auxiliaries and as scale inhibitors.

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Hofheim am Taunus, Germany

Erwin Weiss