Hoechst Aktiengesellschaft

Hartfrid Vollmer

Franz-Josef Dany

Joachim Wortmann

Klaus Hestermann

Georg Elsner

Gero Heymer

Peter Munch

Bernd Lippsmeier

Ernst-Gunther Schlosser

Ernst Reutel

The invention relates to a process for making an isomeric mixture of secondary phosphines with the summation formula C.sub.20 H.sub.27 P. To this end, hydrogen phosphide is reacted with dicyclopentadiene in the presence of an agent yielding free radicals. More specifically, hydrogen phosphide and dicyclopentadiene are used in a molar ratio of 1 to at least 2 and the reaction is effected under a pressure of 5 to 90 bars. The mixture is used in the production of flotation aids and as an ingredient of catalytically active transition metal complexes.

Production of an isomeric mixture of secondary phosphines

The invention relates to a process for making tertiary phosphines of the general formula R.sub.3 P, in which R stands for a linear alkyl radical having 2 to 4 carbon atoms. To this end, hydrogen phosphide is reacted with linear monoolefins having 2 to 4 carbon atoms. More particularly, the tertiary phosphine which is desired to be made is dissolved in an inert solvent and PH.sub.3 and monoolefin are reacted in the solution.

Production of tertiary phosphines

Production of alkylphosphines

Production of novel phosphobetaines of general formula I ##STR1## in which R.sup.1 and R.sup.2 each stand for organic groups having from 1 to 18 carbon atoms, and R.sup.1 or R.sup.2 may be identical with the substituent R, the substituent R being a radical of the general formula II ##STR2## in which R.sup.3 and R.sup.4 each stand for organic groups having from 1 to 18 carbon atoms, and/or hydrogen atoms, and R.sup.5 stands for a linear or branched alkyl group having from 1 to 4 carbon atoms, which may optionally have a halogen or hydroxylic group substituent attached thereto.

Phosphorbetaines and process for making them

Production of tertiary phosphine oxides which contain nitrile groups and correspond to the following general formula I: ##STR1## in which R.sup.1 and R.sub.2 each stand for a straight or branched, identical or different alkyl, cycloalkyl, aryl, alkylaryl or aralkyl group having 1 to 18 carbon atoms, and in which R.sup.1 or R.sub.2 may be identical with R, which stands for a radical of the following general formula II: ##STR2## in which R.sup.3 and R.sup.4 each stand for a straight or branched, identical or different alkyl, cycloalkyl, aryl, alkylaryl or aralkyl group having 1 to 18 carbon atoms, and/or hydrogen atoms. The tertiary phosphine oxides are made by reacting a phosphine of the following general formula III: ##STR3## in which R.sup.5 has the same meaning as R.sup.3 and R.sup.6 has the same meaning as R.sup.4 but is no hydrogen, with an .alpha.,.beta.-unsaturated nitrile of the following general formula IV: ##STR4## in which R.sup.3 and R.sup.4 have the meanings given above. The reaction is effected in a single stage in the presence of water or a water-solvent mixture and the above formula I compounds are separated from the reaction product.

Production of tertiary phosphine oxides

Production of agents reducing the flammability of polyurethane moulding compositions. The agents are more particularly comprised of compounds of the following general formula (I) ##STR1## in which R stands for an alkylene radical having from 2 to 6 carbon atoms, which may be halogen-substituted, if desired, a --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 -- radical, a phenylene radical or an alkyl- or halogenoalkyl-substituted diphenylene methane radical, R.sub.1 and R.sub.2, respectively, stand for a hydrogen atom, an alkyl radical or a halogen-substituted alkyl radical having from 1 to 4 carbon atoms, x + y stand for a number between 0.1 and 3, and n stands for 1 or 2.

Diphosphates

Flame-retardant PVC-plasticizers of the general formula (I) ##STR1## in which R stands for an alkylene radical or a halogen-substituted alkylene radical having from 2 to 6 carbon atoms, a --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 -- radical, a phenylene or an alkyl or halogenoalkyl-substituted diphenylenemethane radical and R.sub.1 stands for a branched or unbranched alkyl radical having from 6 to 18 carbon atoms.

Flame-retardant plasticizers for polyvinyl chloride

Halogen-containing phosphoric acid polyesters of the general formula (I) ##STR1## IN WHICH R stands for an alkylene radical or a halogen-substituted alkylene radical having from 2 to 6 carbon atoms, a --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 -- radical, a phenylene or an alkyl or halogenoalkyl-substituted diphenylenemethane radical, and R.sub.1 stands for a branched or unbranched alkyl radical having from 6 to 18 carbon atoms.

Halogen-containing phosphoric acid polyesters

Production of phosphorus-containing sulfamide derivatives of the general formula: ##STR1## In the above formula, R.sub.1 stands for an alkyl radical or a halogen-substituted, alkyl radical having from 1 to 6 carbon atoms or stands for an aryl radical, and R.sub.2, R.sub.3 and R.sub.4, being identical or different, each stand for a hydrogen atom, a hydroxyalkyl group or a radical of the formula: ##STR2##

Process for making phosphorus sulfamides

Production of polyols containing halogen and phosphorus. The polyols are more particularly comprised of compounds the following general formula (I) ##EQU1## in which R stands for an alkylene radical having from 2 to 6 carbon atoms, which may be halogen-substituted, if desired, a --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 -- radical, a phenylene radical or an alkyl- or halogenoalkyl-substituted diphenylene methane radical, R.sub.1 and R.sub.2, respectively stand for a hydrogen atom, an alkyl radical or a halogen-substituted alkyl radical having from 1 to 4 carbon atoms, x + y stand for a number between 0.1 and 3, and n stands for 1 or 2. The polyols find use as flameproofing agents in plastics, particularly in polyurethane foams.

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Erftstadt Liblar, Germany

Hartfrid Vollmer