Epoxides produced by the oxidation of olefins with air or oxygen

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)

• M.sub.x O.sub.y (L).sub.z ( 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.

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)

• M.sub.x O.sub.y (L).sub.z ( 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.

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

• M.sub.x O.sub.y (L).sub.z ( 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), ##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.