Clariant Finance (bvi) Limited

Clariant International Ltd

Michael Hill

Werner Krause

Martin Sicken

Harald Bauer

Sebastian Hoerold

Sebastian Hörold

Mathias Dietz

The invention relates to a method for producing monofunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester thereof, whereupon said alkylphosphonous acid, the salt or ester (II) thereof is reacted with compounds containing C&#x2550;C, C&#x2550;O, or C&#x2550;N double bonds to obtain compounds of type (III), wherein R, R, R, R, R, Rare identical or different from each other and independently represent, inter alia, H, C-C-alkyl, C-C-aryl, C-C-aralkyl, X represents, inter alia, H, C-C-alkyl, C-C-aryl, and/or Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H, and wherein A represents OH, NH, NHR, NR, or O&#x2014;CO&#x2014;R, and W represents a mineral acid, carboxylic acid, Lewis acid, or organic acid, wherein n is a whole or a fractional number from 0 to 4, and catalyst A represents transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand. The use of said dialkylphosphonic acids, esters, and salts is also disclosed.

Method for the production of monofunctionalized dialkylphosphinic acids, esters and salts, and use thereof

A process for preparing ethylenedialkylphosphinic acids, ethylenedialkylphosphinic esters and ethylenedialkylphosphinic salts, wherein a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, its salt or ester (II), b) the resultant alkylphosphonous acid, its salt or ester (II) is reacted with an acetylenic compound (V) in the presence of a catalyst B, to give the ethylenedialkylphosphinic acid derivative (III), and the catalyst A comprises transition metals, transition-metal compounds and/or catalyst systems which are composed of a transition metal and/or a transition-metal compound and at least one ligand, and the catalyst B comprises peroxide-forming compounds, peroxo compounds and/or azo compounds.

Process for preparing ethylenedialkylphosphinic acids, esters and salts by means of acetylene and use thereof

The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkyl phosphonic acid, salt, salt or ester (II) thereof is reacted with compounds of formula (V) and/or (VI') to yield mono-functionalized dialkylphosphinic acid derivatives (VI) and/or (VI&#x2032;) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivatives (VI) and/or (VI&#x2032;) are reacted to yield a mono-carboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst C, wherein R, R, R, R, R, R, Rare the same or different and stand independently of each other, among other things, for HC-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl, and X and Y are the same or different and stand independently of each other for H, C-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalysts A and C are formed by transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand, and catalyst B is formed by compounds forming peroxides and/or peroxo compounds and/or azo compounds and/or alkali metals and/or alkaline earth metals, alkali hydrides, alkaline earth hydrides and/or alkali alcoholates and alkaline earth alcoholates.

Method for producing dialkylphosphinic acids and esters and salts thereof by means of allyl alcohols-acroleins and use thereof

A process for preparing mono-carboxy-functionalized dialkylphosphinic acids, dialkylphosphinic esters and dialkylphosphinic salts by means of alkylene oxides, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to form an alkylphosphonous acid, its salt or ester (II), b) the resultant alkylphosphonous acid, its salt or ester (II) is reacted with alkylene oxides of the formula (V) in the presence of a catalyst B, to give a mono-functionalized dialkylphosphinic acid derivative (VI), and c) the resultant mono-functionalized dialkylphosphinic acid derivative (VI) is reacted in the presence of a catalyst C to give the mono-carboxy-functionalized dialkylphosphinic acid derivative (III), and the catalysts A and C are transition metals and/or transition-metal compounds and/or catalyst systems which are composed of a transition metal and/or a transition-metal compound and at least one ligand, and the catalyst B is a Lewis acid.

Process for preparing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts by means of alkylene oxides and use thereof

The invention relates to a novel flameproof agent stabiliser combination for thermoplastic and duroplastic polymers, containing, as component A 25-97.7 wt % of a dialkylphosphinic acid salt of formula (I) and/or a diphosphinic acid salt of formula (II) and/or polymers thereof, wherein R, Rare the same or different and represent C-C-alkyl, linear or branched and/or aryl; Rrepresents C-C-alkylene, linear or branched, C-C-arylene, C-C-alkylarylene or C-C-arylalkylene; M represents Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K and/or a protonated nitrogen base; m represents 1-4; n represents 1-4; x represents 1-4, as component B 2-45 wt. % of a monoalkylphosphinic acid salt of general formula (Ill), wherein Rrepresents C-C-alkyl, linear or branched; M represents Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K and/or a protonated nitrogen base; representing, as component C 0.3-30 wt. % of a synergist containing nitrogen or a phosphorous/nitrogen flameproof agent and as component D 0-10 wt. % of a zinc salt or a basic or amphoteric oxide, hydroxide, carbonate, silicate, borate, stannate, mixed oxide-hydroxides, oxide-hydroxide-carbonate, hydroxide-silicates or hydroxide-borates or mixtures of said substances, as components E 0-3 wt. % phosphonite or a phosphonite/phosphite mixture and as component F 0-3 wt.% of an ester or salt of long-chained carboxylic acids, the total of the components always amounting to 100 wt. %.

Flameproof agent stabiliser combination for thermoplastic and duroplastic polymers

A method for producing mono-hydroxy-functionalized dialkylphosphinic acids, esters and salts. The method is includes: a) reacting a phosphinic acid source (I) with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, the salt or the ester (II) thereof, b) reacting the alkylphosphonous acid so obtained, the salt or the ester (II) thereof with a vinyl ester of a carboxylic acid of formula (V) in the presence of a catalyst B to give a mono-functionalized dialkylphosphinic acid derivative (VI) and c) reacting the mono-functionalized dialkylphosphinic acid derivative (VI) so obtained in the presence of a catalyst C to give a mono-hydroxy-functionalized dialkylphosphinic acid derivative (III), the catalyst A is a transition metal, a transition metal compound or a catalyst system including a transition metal, or a transition metal compound and at least one ligand, and the catalyst B is a peroxide-forming compound and/or a peroxo compound or an azo compound, and the catalyst C is an acid or a base.

Method for producing mono-hydroxy-functionalized dialkylphosphinic acids, esters and salts using a vinyl ester of a carobxylic acid and the use thereof

The invention relates to a method for producing mono-aminofunctionalized dialkylphosphinic acids and esters and salts thereof by means of acrylnitriles, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with an acrylnitrile of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted to yield a mono-aminofunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst C or a reduction agent, wherein R, R, R, R, R, R, Rare the same or different and stand independently of each other, among other things, for H, C-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl and X stands for H, C-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and Y stands for a mineral acid, a carboxylic acid, a Lewis acid or an organic acid, n=an integer or fractional number of 0 to 4 and the catalysts A and C are formed by transition metals, transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand, and catalyst B is formed by compounds forming peroxides, peroxo compounds, azo compounds, alkali metals, alkaline earth metals, alkali hydrides, alkaline earth hydrides and/or alkali alcoholates and alkaline earth alcoholates.

Method for producing mono-aminofunctionalized dialkylphosphinic acids and esters and salts thereof by means of acrylnitriles and use thereof

The invention relates to a method for producing monocarboxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, and b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an oxidizing agent or with an oxidizing agent and water or with oxygen and water in the presence of a catalyst B to obtain the alkylphosphonic acid derivative (III), wherein R, R, R, Rare identical or different from each other and independently represent, inter alia, H, C-C-alkyl, C-C-aryl, C-C-aralkyl, C-C-alkylaryl, X and Y are identical or different from each other and independently represent H, C-C-alkyl, C-C-aryl, C-C-aralkyl, C-C-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, and catalysts A and B are transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand.

Method for the production of alkylphosphonic acids, esters, and salts by oxidizing alkylphosphonous acids, and use thereof

A method for producing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts using a vinyl ether. The method is characterized by the following steps: a) reacting a phosphinic acid source (I) with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, the salt or the ester (II) thereof, b) reacting the alkylphosphonous acid so obtained, the salt or the ester (II) thereof with a vinyl ether of formula (V) in the presence of a catalyst B to give a mono-functionalized dialkylphosphinic acid derivative (VI) and c) reacting this derivative (VI) with an oxidant or in the presence of a catalyst C to give a mono-carboxy-functionalized dialkylphosphinic acid derivative (III), wherein the catalysts A and C are transition metals and/or transition metal compounds, and the catalyst B is a peroxide-forming compound and/or a peroxo compound and/or an azo compound.

Method for producing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts using a vinyl ether and the use thereof

A method for producing monohydroxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with alkylene oxides of formula (V) in the presence of a catalyst B to obtain a monofunctionalized dialkylphosphinic acid derivative (III), catalyst A represents transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand, and catalyst B is a Lewis acid.

Method for the production of monohydroxy-functionalized dialkylphosphinic acids, esters, and salts using ethylene oxide, and use thereof

The invention relates to a method for producing mixtures of alkylphosphonous acid and dialkylphosphinic acid salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (II) in the presence of a catalyst A to obtain a mixture of alkylphosphonous acid (III) and dialkylphosphinic acid (IV) or salts or esters thereof, and b) the thus obtained mixture of alkylphosphonous acid (III) and dialkylphosphinic acid (IV) or the salts or esters thereof is reacted with metal compounds of Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na, K and/or a protonated nitrogen base to obtain the corresponding mixtures of alkylphosphonous acid salt (V) and dialkylphosphinic acid salt (VI) of said metals and/or a nitrogen compound, (V) (VI), wherein Y represents Mg, Ca, AI, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na; K and/or a nitrogen compound and n represents &#xbc;, &#x2153;, &#xbd;, 1.

Method for producing mixtures of alkylphosphonous acid salts and dialkylphosphinic acid salts

The invention relates to a process for preparing mono-allyl-functionalized dialkylphosphinic acids, esters and salts with allylic compounds, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, or salt or ester thereof (II), b) the alkylphosphonous acid, or salt or ester thereof (II) thus formed is reacted with allylic compounds of the formula (V) in the presence of a catalyst B and of a base to give a mono-allyl-functionalized dialkylphosphinic acid derivative (III), where R, R, R, R, R, R, R, R, Rare the same or different and are each independently, inter alia, H, C-C-alkyl, C-C-aryl, C-C-aralkyl, C-C-alkylaryl, and X is H, C-C-alkyl, C-C-aryl, C-C-aralkyl, C-C-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base, and the catalysts A and B are transition metals and/or transition metal compounds and/or catalyst systems which are composed of a transition metal and/or a transition metal compound and at least one ligand.

Process for preparing mono-allyl-functionalized dialkylphosphinic acids, salts and esters thereof with allylic compounds, and the use thereof

The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (H) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with compounds of formula (V) to yield mono-functionalized dialkylphosphinic acid derivatives (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivatives (VI) are reacted to yield a mono-carboxyfunctionalized diakylphosphinic acid derivative (III) in the presence of a catalyst C, wherein R, R, R, R, R, R, Rare the same or different and stand independently of each other, among other things, for H, C-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl and X and Y are the same or different and stand independently of each for H, C-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalyst A is formed by transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand, and catalyst B is formed by compounds forming peroxides and/or peroxo compounds and/or azo compounds and/or alkali metals and/or alkaline earth metals, alkali hydrides, alkaline earth hydrides and/or alkali alcoholates and alkaline earth alcoholates, and catalyst C is an acid or a base.

Method for producing dialkylphosphinic acids and esters and salts thereof by means of acrylnitriles and use thereof

The invention relates to a method for producing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts using a vinyl ester of a carboxylic acid. The method is characterized by the following steps: a) reacting a phosphinic acid source (I) with olefins (IV) in the presence of a catalyst A to give an alkylphosphinic acid, the salt or the ester (II) thereof, b) reacting the alkylphosphinic acid so obtained, the salt or the ester (II) thereof with a vinyl ester of a carboxylic acid of formula (V) in the presence of a catalyst B to give a mono-functionalized dialkylphosphinic acid derivative (VI) and c) reacting the mono-functionalized dialkylphosphinic acid derivative (VI) so obtained in the presence of a catalyst C to give a mono-functionalized dialkylphosphinic acid derivative (VII) and d) reacting the mono-functionalized dialkylphosphinic acid derivative (VII); with an oxidant or in the presence of a catalyst D to give a mono-carboxy-functionalized dialkylphosphinic acid derivative (III).

Method for producing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts using a vinyl ester of a carboxylic acid and the use thereof

The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the alkylphosphonic acid thus obtained, salt or ester (II) thereof is reacted with an &#x3b1;,&#x3b2;-unsaturated carboxylic acid derivative (V) to yield a mono-carboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, wherein R, R, R, R, R, R, Rare the same or different and stand independently of each other, among other things, for H, C-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl, and X and Y are the same or different and stand independently of each other for H, C-Calkyl, C-Caryl, C-Caralkyl, C-Calkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalyst A is formed by transition metals and/or transition metal compounds and/or catalyst systems composed of a transition metal and/or a transition metal compound and at least one ligand, and catalyst B is formed by compounds forming peroxides and/or peroxo compounds and/or azo compounds and/or alkali metals and/or alkaline earth metals, alkali hydrides, alkaline earth hydrides and/or alkali alcoholates and alkaline earth alcoholates.

Growing community of inventors

Cologne, Germany

Michael Hill