Single-stage method for producing α-hydroxy ethers by oxidizing C=C unsaturated compounds with hydroperoxides
AssigneeWE-DEA Aktiengesellschaft für Mineraloel und Chemie
InventorsMark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
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Abstract
A single-stage method for producing α-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.
Claims17
A single-stage process for the production of α-hydroxy ethers according to formulae (I) and (II)
- by oxidation of olefinic substrates with organic hydroperoxides and opening of the resultant oxirane ring by mono- or polyhydric alcohols, wherein molybdenum compounds in combination with boron trifluoride or alumina or 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane are used as a catalyst system, and wherein
- R1, R2, R4, and R6, independently of one another, are saturated, unbranched or branched hydrocarbon radicals having 1 to 22 carbon atoms, or are completely or partially fluorinated hydrocarbon radicals having 1 to 22 carbon atoms,
- R3 represents a mono- or polyhydric, linear or branched radical of an alcohol having 1 to 22 carbon atoms which may be fluorinated wholly or in part,
- R5 is a spacer consisting of an unbranched or branched chain with 2 to 100 carbon atoms which contains 0 to 20 oxygen atoms, 0 to 20 nitrogen atoms, 0 to 4 sulfur atoms, and 0 to 3 phosphorus atoms and which has 0 to 20 hydroxyl, carbonyl, carboxyl, amino and/or acylamino groups, and
- X and Y, independently of one another, are substituents according to formula XVI
- —(C2H4O)α(C3H6O)βH (XVI)
- where
- α=0 to 50
- β=0 to 60
- and
- α+β=1 to 100
- and wherein the alkoxide units are incorporated randomly or blockwise and the sequence is optional,
- or are substituents according to formula XVII
- —(C2H4O)γ(C3H6O)δ-FR (XVII)
- where each
- γ=0 to 20
- δ=0 to 20
- and
- γ+δ=0 to 40
- and FR represents a functional radical
- —CH2—COOM, —SO3M, —P(O)(OM)2,
- —C3H6—SO3M, or
- —O—C(O)—C2H3(SO3M)—CO2M′,
- wherein M, M′ are equal to alkali, ammonium, alkanol ammonium, or ½ alkaline earth metal, and the alkoxide units, too, are incorporated randomly or blockwise and the sequence is optional.
A process as claimed in any one of the preceding claims, characterized in that
- the process is performed in the absence of water.
A process as claimed in any one of 1, 2 or 3, characterized in that unsaturated fatty acids or fatty acid esters or di- and trimers of butene or tri- and tetramers of propene are employed.
A single-stage process for the production of α-hydroxy ethers according to formulae (I) and (II)
- by oxidation of olefinic substrates with organic hydroperoxides and opening of the resultant oxirane ring by mono- or polyhydric alcohols, wherein a molybdenum compound selected from the group consisting of MoO2(acac)2 and Mo(CO)6 in combination with a compound selected from the group consisting of boron trifluoride, alumina, 1,8-diazabicyclo-(5.4.0)-undec-7-ene, 1,4-diazabicyclo-(2.2.2.)-octane and mixtures thereof are used as a catalyst system, and wherein
- R1, R2, R4, and R6, independently of one another, are saturated, unbranched or branched hydrocarbon radicals having 1 to 22 carbon atoms, or are completely or partially fluorinated hydrocarbon radicals having 1 to 22 carbon atoms,
- R3 represents a mono- or polyhydric, linear or branched radical of an alcohol having 1 to 22 carbon atoms which may be fluorinated wholly or in part,
- R5 is a spacer consisting of an unbranched or branched chain with 2 to 100 carbon atoms which contains 0 to 20 oxygen atoms, 0 to 20 nitrogen atoms, 0 to 4 sulfur atoms, and 0 to 3 phosphorus atoms and which has 0 to 20 hydroxyl, carbonyl, carboxyl, amino and/or acylamino groups, and
- X and Y, independently of one another, are substituents according to formula XVI
- —(C2H4O)α(C3H6O)βH (XVI)
- where
- α=0 to 50
- β=0 to 60
- and
- α+β=1 to 100
- and wherein the alkoxide units are incorporated randomly or blockwise and the sequence is optional,
- or are substituents according to formula XVII
- —(C2H4O)γ(C3H6O)δ-FR (XVII)
- where each
- γ=0 to 20
- δ=0 to 20
- and
- β+δ=0 to 40
- and FR represents a functional radical
- —CH2—COOM, —SO3M, —P(O) (OM)2,
- —C3H6—SO3M, or
- —O—C(O)—C2H3(SO3M)—CO2M′,
- wherein M, M′ are equal to alkali, ammonium, alkanol ammonium or ½ alkaline earth metal, and the alkoxide units, too, are incorporated randomly or blockwise and the sequence is optional.
Dependencies are inferred from the claim text.