Process for preparation of 2-(dialkoxymethyl)-carboxylic acid esters
AssigneeHoechst Aktiengesellschaft
InventorHeinz Strutz
Life of this patent
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Abstract
Process for the preparation of 2-(dialkoxymethyl)carboxylic acid esters of the formula I ##STR1## by oxidizing .beta.-acetalization of acrylic acid esters with alcohols R.sup.1 OH, wherein R.sup.1 has the meaning mentioned, in the presence of oxygen as the oxidant and of a catalyst system based on one or more metals of the platinum group and/or compounds thereof and of a copper compound, comprises carrying out the reaction at a temperature of up to 80.degree. C. and in which the catalyst system contains 1 to 4 equivalents of anions, based on the sum of the metal atoms and metal cations, of which at most 3 equivalents are halide ions, the halogen having a molecular weight of at least 35.
Claims19
A process for the preparation of 2-(dialkoxymethyl)carboxylic acid esters of the formula I ##STR2## wherein R.sup.1 is a non-aromatic hydrocarbon radical or a heterocyclic non-aromatic radical, which apart from oxygen, nitrogen and/or sulfur atoms in the ring only contains carbon and hydrogen atoms, and each of which has 1 to 20 carbon atoms, it being possible for the radical R.sup.1 to carry 1 to 5 substituents and the substituents being identical or different and being halogen, an aryl, carbalkoxy, dialkylamino, diarylamino or cyano group or an alkoxy groups, the alkyl being substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl, or is an aryloxy group, the aryl being substituted or unsubstituted C.sub.6 - to C.sub.14 -aryl, a substituted or unsubstituted benzyl or phenethyl radical or an R.sup.4 O--(R.sup.5 O).sub.x --R.sup.5 group, where R.sup.4 is substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl or C.sub.6 - to C.sub.14 -aryl, R.sup.5 is a branched or unbranched hydrocarbon radical having 1 to 4 carbon atoms or phenylene and x=1 to 6,
- R.sub.2 is hydrogen or alkyl having 1 to 5 carbon atoms and
- R.sup.3 is unsubstituted or substituted C.sub.6 - to C.sub.14 -aryl or a radical mentioned under R.sup.1, which comprises the step of:
- conducting an oxidizing .beta.-acetalization reaction of acrylic acid esters with alcohols R.sup.1 OH, wherein R.sup.1 has the meaning mentioned, in the presence of:
- an oxidant selected from the group consisting of pure oxygen or atmospheric oxygen
- a catalyst system containing one or more metals of the platinum group and/or compounds thereof and of a copper compound, said catalyst system containing 1 to 4 equivalents of anions, based on the sum of the metal atoms and the metal cations, of which at most 3 equivalents are halide ions, the halogen having a molecular weight of at least 35;
- at a temperature of up to 80.degree. C.
A process for the preparation of 2-(dialkoxymethyl)carboxylic acid esters of the formula I ##STR3## wherein R.sup.1 is a non-aromatic hydrocarbon radical or a heterocyclic non-aromatic radical, which apart from oxygen, nitrogen and/or sulfur atoms in the ring only contains carbon and hydrogen atoms, and each of which has 1 to 20 carbon atoms, it being possible for the radical R.sup.1 to carry 1 to 5 substituents and the substituents being identical or different and being halogen, an aryl, carbalkoxy, dialkylamino, diarylamino or cyano group or an alkoxy group, the alkyl being substituted or unsubstituted C.sub.1 - to C.sub.12 alkyl, or is an aryloxy group, the aryl being substituted or unsubstituted C.sub.6 - to C.sub.14 -aryl, a substituted or unsubstituted benzyl or phenethyl radical or an R.sup.4 O--(R.sup.5 O).sub.x --R.sup.5 group, where R.sup.4 is substituted or unsubstituted C.sub.1 - to C.sub.12 -alkyl or C.sub.6 - to C.sub.14 -aryl, R.sup.5 is a branched or unbranched hydrocarbon radical having 1 to 4 carbon atoms or phenylene and x=1 to 6,
- R.sup.2 is hydrogen or alkyl having 1 to 5 carbon atoms and
- R.sup.3 is unsubstituted or substituted C.sub.6 - to C.sub.14 -aryl or a radical mentioned under R.sup.1,
- by oxidizing .beta.-acetalization of acrylic acid esters with alcohols R.sup.1 OH, wherein R.sup.1 has the meaning mentioned, in the presence of an oxidant consisting of oxygen and of a catalyst system containing one or more metals of the platinum group and/or compounds thereof and of a copper compound, comprises carrying out the reaction at a temperature of up to 70.degree. C. and in which the catalyst system contains 1 to 4 equivalents of anions, based on the sum of the metal atoms and metal cations, of which at most 3 equivalents are halide ions, the halogen having molecular weight of at least 35.
Dependencies are inferred from the claim text.