Method for the production of monohydroxy-functionalized dialkylphosphinic acids, esters, and salts using ethylene oxide, and use thereof
View Patent ↗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.
1. A method for producing monohydroxy-functionalized dialkylphosphinic acids, esters or salts thereof comprising the steps of:
a) reacting a phosphinic acid source (I)
with 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 at least one alkylene oxide (V), wherein the at least one alkylene oxide is ethylene oxide, 1,2-propylene oxide or 2,3-epoxy-1propanol
in the presence of a catalyst B and at least one base to form monofunctionalized dialkylphosphinic acid derivative (III)
where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are identical or different and are independently H, CH 2 OH, methyl or ethylene, wherein X is Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Na, K, H, a protonated nitrogen base or a combination thereof and the catalyst A is selected from the group consisting of a transition metal, transition metal compound and catalyst systems composed of a transition metal, transition metal compound or a combination thereof and at least one ligand, and the catalyst B is a Lewis acid and wherein the bases used in process step b) are metals, metal hydrides, organometal compounds or metal alkoxides.
2. The method according to claim 1 wherein the monohydroxy-functionalized dialkylphosphinic acid, its salt or ester (III) obtained after step b) is reacted in a step c) with a metal compound, a protonated nitrogen base or a combination thereof, wherein the metal compound contains the metal Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na or K to form the monohydroxy-functionalized dialkylphosphinic acid salts (III) of the metal compound, of the nitrogen base or a combination thereof.
3. The method according to claim 1 wherein the alkylphosphonous acid, salt or ester (II) obtained after step a), or the monohydroxy-functionalized dialkylphosphinic acid, salt or ester (III) obtained after step b), is esterified with an alkylene oxide or an or branched, saturated or unsaturated, monohydric or polyhydric organic alcohol having a carbon chain length of C 1 -C 18 , or a combination thereof, and the resulting alkylphosphonous ester (II) or monohydroxy-functionalized dialkylphosphinic ester (III) are subjected to the further reaction step b).
4. The method according to claim 1 , wherein X is H, C Mg, Al Zn, Ti, Fe, Ce, or a combination thereof.
5. The method according to claim 1 , wherein the transition metal or the transition metal in the transition metal compound is selected from the first, seventh or eighth transition groups.
6. The method according to claim 1 , wherein the transition metal or the metal of the transition metal compound is rhodium, nickel, palladium, platinum or ruthenium.
7. The process as claimed in claim 1 , wherein the base of the process is selected from lithium, lithium hydride, lithium aluminohydride, methyllithium, butyllithium, t-butyllithium, lithium diisopropylamide, sodium, sodium hydride, sodium methoxide, sodium ethoxide, sodium butoxide, potassium methoxide, potassium ethoxide or potassium butoxide.