US 2011/0251312 A1 · Process for Preparing Ethylenedialkylphosphinic Acids, Esters and Salts by Means of Acetylene and Use Thereof

Abstract

The invention relates to a process for preparing ethylenedialkylphosphinic acids, ethylenedialkylphosphinic esters and ethylenedialkylphosphinic salts, 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, 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), where R1, R2, R3, R4, R5, R6, R11, R12, R13 and R14 are identical or different and independently of one another inter alia are H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl and X is 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 the catalyst A comprises 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 comprises peroxide-forming compounds and/or peroxo compounds and/or azo compounds.

Claims22

Dependent claims

A process for preparing ethylenedialkylphosphinic acids, esters or salts comprising the steps of

a) reacting a phosphinic acid source (I)
with olefins IV
in the presence of a catalyst A to give an alkylphosphonous acid (II), or salt or ester thereof,
b) reacting the alkylphosphonous acid (II), or salt or ester with at least one acetylenic compound (V)
in the presence of a at least one catalyst B to give the ethylenedialkylphosphinic acid derivative (III)
where R1, R2, R3, R4, R5, R6, R11, R12, R13, R14 are the same or different and are 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)R7, (CH2)mC(O)R7, CH═CH—R7, CH═CH—C(O)R7, and wherein R7 is C1-C8-alkyl or C6-C18-aryl, m is an integer from 0 to 10, X is H, 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—C[CH3]HO)O-alkyl, (CH2)k—CH═CH(CH2)kH, (CH2)kNH2, (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, or a protonated nitrogen base, the catalyst A is a transition metal, transition metal compound catalyst systems composed of a transition metal, a transition metal compound and at least one ligand, and the catalyst B is peroxide-forming compound, peroxo compound, azo compound or a combination thereof.

3 more elements

Dependencies are inferred from the claim text.

Process for Preparing Ethylenedialkylphosphinic Acids, Esters and Salts by Means of Acetylene and Use Thereof

Life of this patent

Process for Preparing Ethylenedialkylphosphinic Acids, Esters and Salts by Means of Acetylene and Use Thereof

Life of this patent

Abstract

Claims22