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Claims for Patent: 5,969,166

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Claims for Patent: 5,969,166

Title: Epoxides produced by the oxidation of olefins with air or oxygen
Abstract:Catalysts for the selective epoxidization of olefins with atmospheric oxygen, processes for their preparation and processes for the preparation of epoxides by oxidation of olefins with air or oxygen. Compounds of the formula (1) as catalysts for the selective epoxidization of alkenes in which the indices x, y and z have the following meaning: x is a whole number from 1 to 3, y is a whole number from 1 to 2x+1, y being selected so that the sum of x+z gives a metal oxidation number of +5 (vanadium) or +6 (molybdenum, ruthenium); z is a whole number in the range from 2 to 2x; M is molybdenum, ruthenium or vanadium and L is an N, 0 or S donor ligand. Heterogeneous catalysts for the selective oxidation of olefins in the presence of oxygen, comprising an inorganic or organic support material and compounds of the formula (1), and a process for the selective epoxidization of alkenes of the formula ##STR1## with atmospheric oxygen in the presence of a catalyst of the formula (1) are also described.
Inventor(s): Scharbert; Bernd (Frankfurt, DE), Lobmaier; Gerhard (Gersthofen, DE), Herrmann; Wolfgang Anton (Freising, DE)
Assignee: Hoechst Aktiengesellschaft (Frankfurt, DE)
Application Number:08/860,261
Patent Claims: 1. A compound of the formula (1) as a catalyst for selective epoxidization of alkenes

in which

the indices x, y and z have the following meaning:

x is a whole number from 1 to 3, y is a whole number from 1 to 2x+1, y being selected so that the sum of x+z gives a metal oxidation number of +6; z is a whole number in the range from 2 to 2x;

M is ruthenium or molybdenum

L is an N, O or S donor ligand,

with the proviso that, in particular in the case where M is Mo, L is a compound which is derived from a compound of the formula (2), (3) or (4), ##STR18## in which X is N O or S and X' is N or C and

R.sup.1 and R.sup.2 independently of one another are a branched or unbranched, optionally halogenated C.sub.1 -C.sub.12 -alkyl radical or an optionally substituted C.sub.6 -C.sub.14 -aryl or heteroaryl radical, or the two together are a group C.dbd.O or C.dbd.S, or R.sup.1 or R.sup.2 is a hydrogen radical, and the selectivity in the epoxidization reaction is more than 45% if a molybdenum compound is used and is .gtoreq.30% if a ruthenium compound is used.

2. A heterogeneous catalyst for the selective oxidation of olefins in the presence of oxygen, comprising an inorganic or organic support material and a compound of the formula (1)

in which

the indices x, y and z have the following meaning:

x is a whole number from 1 to 3, y is a whole number from 1 to 2x+1, y being selected so that the sum of x+z gives a metal oxidation number of +6; z is a whole number in the range from 2 to 2x;

M is ruthenium or molybdenum

L is an N, O or S donor ligand,

with the proviso that, in particular in the case where M is Mo, L is a compound which is derived from a compound of the formula (2), (3) or (4), ##STR19## in which X is N, O or S and X' is N or C and

R.sup.1 and R.sup.2 independently of one another are a branched or unbranched, optionally halogenated C.sub.6 -C.sub.12 -alkyl radical or an optionally substituted C.sub.6 -C.sub.14 -aryl or heteroaryl radical, or the two together are a group C.dbd.O or C.dbd.S, or R.sup.1 or R.sup.2 is a hydrogen radical, and the selectivity in the oxidization of olefins is more than 45% if a molybdenum compound is used.

3. A compound as claimed in claim 1, wherein the complex of the formula (1 ) is readily soluble in organic solvents.

4. A catalyst as claimed in claim 2, wherein the inorganic or organic support material used is a material selected from the group consisting of: aluminum oxides, silicon dioxide, alumosilicates, titanium dioxide, zirconium dioxide, thorium dioxide, lanthanum oxide, magnesium oxide, calcium oxide, barium oxide, tin oxide, cerium dioxide, zinc oxide, boron oxide, boron nitride, boron carbide, boron phosphate, zirconium phosphate, silicon nitride or silicon carbide or polypyridines or polyacrylates.

5. A process for the selective epoxidization of alkenes of the formula ##STR20## with only atmospheric oxygen as the oxidizing agent in the presence of a catalyst of the formula (1)

in which the symbols R.sup.1, R.sup.2, R.sup.3, R.sup.4, M, L, x, y and z have the following meaning:

R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.12 -alkoxy or C.sub.6 -C.sub.10 -aryl, or R.sup.1 and R.sup.2 together form a ring having 5 to 30 carbon atoms;

the indices x, y and z having the following meaning:

x is a whole number from 1 to 3, y is a whole number from 1 to 2x+1, y being selected so that the sum of x+z gives a metal oxidation level of +6; the index z is a whole number in the range from 2 to 2x;

M is ruthenium or molybdenum and

L is a donor ligand,

with the proviso that, in particular if M is Mo, L is a compound which is derived from a compound of the formula (2), (3) or (4), ##STR21## in which X is N, O or S and X' is N or C and

R.sup.1 and R.sup.2 independently of one another are a branched or unbranched, optionally halogenated C.sub.1 -C.sub.12 -alkyl radical or an optionally substituted C.sub.6 -C.sub.14 -aryl or heteroaryl radical, or the two together are a group C.dbd.O or C.dbd.S, or R.sup.1 or R.sup.2 is a hydrogen radical, and the selectivity in the reaction is .gtoreq.40% if a molybdenum compound is used, or the selectivity in the reaction is .gtoreq.30% if a ruthenium compound is used.

6. The process as claimed in claim 5, wherein a compound which is derived from 1,1-(C.sub.1 -C.sub.6)-alkyl-1-(2-pyridyl)methanol, 1-(2-pyridyl)-cyclohexan-1-ol, 1-phenyl-1-(2-pyridyl)methanol, 1,1-(C.sub.1 -C.sub.6)-alkyl-1(2thiophenyl)methanol, 1, 1-(C.sub.1 -C.sub.6)-perfluoroalkyl-1-(2-thiophenyl)methanol, 1,1-(C.sub.1 -C.sub.6)-alkyl-1-(2-pyrrolyl)methanol, 1,1-(C.sub.1 -C.sub.6) -alkyl-1-(2-imidazole)methanol, 1,1-(C.sub.1 -C.sub.6)-perfluoroalkyl-1-(2imidazole)methanol is employed as the donor ligand.

7. The process as claimed in claim 5, wherein an aliphatic, optionally branched C.sub.2 -C.sub.30 -olefin or alicyclic C.sub.5 -C.sub.12 -olefin is epoxidized.

8. The process as claimed in claim 5, wherein the oxygen used as the oxidizing agent is used in the pure form or is diluted with an inert gas.

9. The process as claimed in claim 5, wherein the reaction temperature is in the range from 30 to 300.degree. C. during the oxidation of C.sub.6 -C.sub.12 -alkenes and in the range from 120 to 230.degree. C. during the oxidation Of C.sub.2 -C.sub.5 -alkenes and the pressure is selected such that the reaction proceeds in the liquid phase.

10. The process as claimed in claim 5, wherein the oxidation is carried out without a solvent, in the pure olefin.

11. The process as claimed in claim 5, wherein the oxidation is carried out in a solvent selected from the group consisting of halogenated aromatics, halogenated or non-halogenated hydrocarbons, C.sub.1 -C.sub.12 alcohols or in water.

12. A compound of the formula (1) which readily soluble in organic solvents as a catalyst for selective epoxidization of alkenes

in which

the indices x, y and z have the following meaning:

x is a whole number from 1 to 3, y is a whole number from 1 to 2x+1, y being selected so that the sum of x+z gives a metal oxidation number of +6; z is a whole number in the range from 2 to 2x;

M is ruthenium or molybdenum

L is an N, O or S donor ligand,

with the proviso that, in particular in the case where M is Mo, L is a compound which is derived from a compound of the formula (2), (3) or (4), ##STR22## in which X is N, O or S and X' is N or C and

R.sup.1 and R.sup.2 independently of one another are a branched or unbranched, optionally halogenated C.sub.1 -C.sub.12 -alkyl radical or an optionally substituted C.sub.6 -C.sub.14 -aryl or heteroaryl radical, or the two together are a group C.dbd.O or C.dbd.S, or R.sup.1 or R.sup.2 is a hydrogen radical, and the selectivity in the epoxidization reaction is more than 45% if a molybdenum compound is used, and is .gtoreq.30% if a ruthenium compound is used.
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