Preparation of phosphonic and/or phosphinic acids
AssigneeHoechst Aktiengesellschaft
InventorHans-Jerg Kleiner
Life of this patent
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Abstract
Preparation of phosphonic and/or phosphinic acids by hydrolytic cleavage of phosphonic and/or phosphinic acid alkyl esters in the presence of the phosphonic and/or phosphinic acid by carrying out the hydrolysis at a temperature of from 170.degree. to 300.degree. C with the use of at least a stoichiometric amount of water, and by distilling off the alkanol formed, optionally together with water.
Claims13
A process for the preparation of alkyl alcohols and phosphonic and/or phosphinic acids of the formula (I) ##STR6## where R.sup.1 is an alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical having from 2 to 20 carbon atoms, an aralkyl radical having from 7 to 12 carbon atoms or an aryl radical having from 6 to 10 carbon atoms, these radicals optionally being mono- to trisubstituted by C1, Br, alkyl or alkoxy groups each having from 1 to 4 carbon atoms;
- or R.sup.1 is a radical of the formula (Ia) ##STR7## where Z is an alkylene radical having from 2 to 6 carbon atoms, a phenylene, biphenylene, naphthylene radical or a radical of the formula (Ib) ##STR8## wherein n.sub.1 and n.sub.2 are identical or different integers of from 1 to 4, and R.sup.2 in the formulae (I) and (Ia) is either as defined for R.sup.2, except the radical of formula (Ia), R.sup.1 and R.sup.2 being either identical or different, or OH;
- by hydrolytic cleavage of phosphonic and/or phosphinic acid alkyl esters of the formula (II) ##STR9## where R.sup.3 is as defined above for R.sup.1 except the radical of formula (Ia), or a radical of the formula (IIa) ##STR10## where Z is as defined in formula (Ia), and R.sup.4 in formulae (II) and (IIa) is either as defined for R.sup.3 except the radical of formula (IIa), R.sup.3 and R.sup.4 being either identical or different, or OR.sup.5 or CH, R.sup.5 being a straight-chain or branched alkyl group having from 2 to 8 carbon atoms, optionally being substituted by chlorine or bromine;
- in the presence of the phosphonic and/or phosphinic acid of formula (I), which comprises carrying out the hydrolysis at atmospheric pressure and at a temperature of from 170.degree. to 300.degree. C, with the use of at least a stoichiometric amount of water, and by distilling off the alcohol formed, optionally with water.
A process for the preparation of a straight chain or branch alkyl alcohol having 2 to 8 carbon atoms and a phosphonic acid of the formula III ##STR11## wherein R.sub.1 is a member selected from the group consisting of ethyl, propyl, hexyl, octyl, hexadecane, chloromethyl, benzyl and p-bromobenzene, or phosphinic acids of the formula V ##STR12## wherein R.sub.2 is methyl and R.sub.3 is a member selected from the group consisting of ethyl, vinyl, octyl, phenyl and benzyl by a hydrolytic cleavage reaction of a phosphonic acid alkyl ester of the formula IV ##STR13## wherein R.sub.1 is as defined above and each of R.sub.5 is a member selected from the group consisting of ethyl, propyl, n-butyl, iso-butyl, 2-ethylhexyl, octyl, or one of said --OR.sub.5 is a --OH or by a hydrolytic cleavage reaction of a phosphinic acid alkyl ester of the formula ##STR14## wherein R.sub.2 and R.sub.3 are as defined above and R.sub.4 is a member selected from the group consisting of ethyl, isobutyl and 2-ethyl hexyl;
- wherein the hydrolytic cleavage reaction is carried out in the presence of 2 to 30 weight % of the respective phosphonic or phosphinic acid of formula III or V, based on weight of the corresponding phosphonic or phosphinic acid ester of formula IV or VI, respectively, to form the corresponding phosphonic acid and an alcohol or phosphinic acid and an alcohol, said reaction being carried out with at least a stoichiometric amount of water being present during the reaction or being gradually added during the reaction, and said reaction being carried out at atmospheric pressure and at a temperature of 170.degree. to 300.degree. C, distilling off the alcohol during the reaction, or distilling the alcohol and water during the reaction.
A process for the preparation of a straight chain or branched chain alkyl alcohol having 2 to 8 carbon atoms and a phosphonic acid of the formula III ##STR15## wherein R.sub.1 is a member selected from the group consisting of ethyl, propyl, hexyl, octyl, hexadecane, chloromethyl, benzyl and p-bromobenzene, by a hydrolytic cleavage reaction of a phosphonic acid alkyl ester of the formula IV ##STR16## wherein R.sub.1 is as defined above and each of R.sub.5 is a member selected from the group consisting of ethyl, propyl, n-butyl, iso-butyl, 2-ethylhexyl, octyl, or one of said -OR.sub.5 is a -OH, wherein the hydrolytic cleavage reaction is carried out in the presence of 2 to 30 weight percent of the phosphonic acid of formula III, based on weight of the corresponding phosphonic acid ester of formula IV, to form the corresponding phosphonic acid and an alkyl alcohol, said process consisting essentially of carrying out the reaction at atmospheric pressure and a temperature of about 170.degree. to 300.degree. C, while gradually adding during the reaction at least a stoichiometric amount of water sufficient to form said alkyl alcohol and distilling off the alkyl alcohol formed during the reaction.
A process for the preparation of a straight chain or branched chain alkyl alcohol having 2 to 8 carbon atoms and a phosphinic acid of the formula V ##STR17## wherein R.sub.2 is methyl and R.sub.3 is a member selected from the group consisting of ethyl, vinyl, octyl, phenyl and benzyl, by a hydrolytic cleavage reaction o a phosphinic acid alkyl ester of the formula IV ##STR18## wherein R.sub.2 and R.sub.3 are as defined above and R.sub.4 is a member selected from the group consisting of ethyl, isobutyl and 2-ethyl hexyl;
- wherein the hydrolytic cleavage reaction is carried out in the presence of 2 to 30 weight percent of the phosphinic acid of formula V, based on weight of the corresponding phosphinic acid ester of formula VI, to form the corresponding phosphinic acid and an alkyl alcohol, said process consisting essentially of carrying out the reaction at atmospheric pressure and at a temperature of about 170.degree. to 300.degree. C, while gradually adding during the reaction at least a stoichiometric amount of water sufficient to form said alkyl alcohol and distilling off the alkyl alcohol formed during the reaction.
Dependencies are inferred from the claim text.