US 2011/0213079 A1Published application

Method for Producing Monoamino-Functionalised Dialkylphosphinite Acids Esters and Salts and Use Thereof

AssigneeClariant Finance (BVI) Limited

InventorsMichael Hill, Werner Krause, Martin Sicken

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Abstract

The invention relates to method for producing mono amino-functionalised dialkylphosphonic acids esters and salts, characterised 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, the salt or ester thereof (II), b) the alkylphosphonous acid, the salt or ester thereof (II) produced above is reacted with an allylamine of formula (V) in the presence of a catalyst B to give mono amino-functionalised dialkylphosphinic acid derivatives (III) where, R1, R2, R3, R4, R5, R6, R7, R8, R9 independently=amongst others, H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X═H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 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 Y=a mineral acid, a carboxylic acid, a Lewis acid or organic acid, where n=a whole or fractional number from 0 to 4, catalyst A is a transition metal and/or transition metal compound and/or catalyst system comprising a transition metal and/or a transition metal compound and at least one ligand and catalyst B is compounds forming peroxides and/or peroxide compounds and/or azo compounds.

A method for producing monoamino-functionalized dialkylphosphinic acids, esters or salts, comprising the steps of:

a) reacting a phosphinic acid source (I)
with one or more olefins (IV)
in the presence of a catalyst A to form an alkylphosphonous acid, salt or ester (II)
b) reacting the alkylphosphonous acid, salt or ester (II) with an at least one allyl-amine (V)
in the presence of a catalyst B to form a monoamino-functionalized dialkylphosphinic acid derivative (III)
where R1, R2, R3, R4, R5, R6, R7, R8, R9 are identical or different and are each independently H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, CN, CHO, OC(O)CH2CN, CH(OH)C2H5, CH2CH(OH)CH3, 9-anthracene, 2-pyrrolidone, (CH2)mOH, (CH2)mNH2, (CH2)mNCS, (CH2)mNC(S)NH2, (CH2)mSH, (CH2)mS-2-thiazoline, (CH2)mSiMe3, C(O)R10, (CH2)mC(O)R10, CH═CHR10 or CH═CH—C(O)R10 and where R10 is C1-C8-alkyl or C6-C18-aryl and m is an integer from 0 to 10 and X is C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, (CH2)kOH, CH2—CHOH—CH2OH, (CH2)kO(CH2)kH, (CH2)k—CH(OH)—(CH2)kH, (CH2—CH2O)kH, (CH2—C[CH3]HO)kH, (CH2—C[CH3]HO)k(CH2—CH2O)kH, (CH2—CH2O)k(CH2—C[CH3]HO)H, (CH2—CH2O)k-alkyl, (CH2—C[CH3]HO)k-alkyl, (CH2—C[CH3]HO)k(CH2—CH2O)k-alkyl, (CH2—CH2O)k(CH2—CH3]HO)O-alkyl, (CH2)k—CH═CH(CH2)kH, (CH2)kNH2 or (CH2)kN[(CH2)kH]2, where k is an integer from 0 to 10, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H, a protonated nitrogen base and is a mineral acid, carboxylic acid, Lewis acid or organic acid or a combination thereof, where n is a whole or fractional number from 0 to 4 and the catalyst A is selected from the group of transition metals, transition metal compounds, catalyst systems composed of a transition metal, transition metal compound and at least one ligand and a combination thereof, and the catalyst B is selected from the group consisting of peroxide-forming compounds, peroxo compounds, azo compounds and a combination thereof.

3 more elements

Facts

Application

13/127,105Filed 6 Oct 2009

Priority

DE 10 2008 056 339.07 Nov 2008

Published

1 Sep 2011

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C09K 21/12
Organic materials: containing phosphorus
C07F 9/301
Phosphinic acids [R2P]; Thiophosphinic acids ; [R2P ]: acyclic saturated acids which can have further substituents on alkyl
C07F 9/3211
The acid moiety containing a substituent or a structure which is considered as characteristic: esters of acyclic saturated acids which can have…
C08K 5/5313
Bound to oxygen and to carbon only: phosphinic compounds, e.g. R2=POR'

Abstract

Claims15