Preparation of phosphonic and/or phosphinic acids
AssigneeHoechst Aktiengesellschaft
InventorsWalter Dursch, Hans-Jerg Kleiner, Horst-Dieter Thamm
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 160.degree. to 250.degree. C with the use of at least a stoichiometric amount of water, and by distilling off the alkanol formed, optionally together with water.
Claims14
A process for the preparation of methyl alcohol 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 Cl, 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## where 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.1, 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 OCH.sub.3 or OH;
- 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 160 to 250.degree. C, with the use of at least a stoichiometric amount of water, and by distilling off the methyl alcohol formed, optionally together with water.
A process for the preparation of methyl alcohol 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, p-bromobenzene and eicosyl,
- 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, benzyl and eicosyl;
- by a hydrolytic cleavage reaction of a phosphonic acid ester of the formula IV ##STR13## wherein R.sub.1 is as defined above and one of said --OCH.sub.3 can be --OH,
- or by a hydrolytic cleavage reaction of a phosphinic acid ester of the formula ##STR14## wherein R.sub.2 and R.sub.3 are as defined above;
- wherein the hydrolytic cleavage 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 methyl alcohol or phosphinic acid and methyl 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 160 to 250.degree. C, distilling off the methyl alcohol during the reaction, or distilling the methyl alcohol and water during the reaction.
A process for the preparation of methyl alcoholand 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, p-bromobenzene and eicosyl;
- by a hydrolytic cleavage reaction of a phosphonic acid ester of the formula IV ##STR16## wherein R.sub.1 is as defined above and one of said --OCH.sub.3 can be --OH;
- wherein the hydrolytic cleavage is carried out in the presence of 2 to 30 weight % 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 methyl alcohol, said process consisting essentially of carrying out the reaction at atmospheric pressure and a temperature of about 160.degree. to 250.degree. C, while gradually adding during the reaction at least a stoichiometric amount of water sufficient to form said methyl alcohol and distilling off the methyl alcohol formed during the reaction.
A process for the preparation of methy alcohol 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, benzyl and eicosyl;
- by a hydrolytic cleavage reaction of a phosphinic acid ester of the formula ##STR18## wherein R.sub.2 and R.sub.3 are as defined above:
- wherein the hydrolytic cleavage is carried out in the presence of 2 to 30 weight % of the phosphinic acid of the formula V, based on weight of the corresponding phosphinic acid ester of formula VI, to form the corresponding phosphinic acid and methyl alcohol, said process consisting essentially of carrying out the reaction at atmospheric pressure and at a temperature of about 160 to 250.degree. C, while gradually adding during the reaction at least a stoichiometric amount of water sufficient to form said methyl alcohol and distilling off the methyl alcohol formed.
Dependencies are inferred from the claim text.