Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-10-18
2000-10-03
Trinh, Ba K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549531, 556 10, 556 52, 556460, C07D30112, C07D30119, C07F 702, C07F 721, C07F 728
Patent
active
061275573
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The invention relates to a method for synthesizing silasesquioxane metal complexes, to new silasesquioxane metal complexes and to their use.
The synthesis of silasesquioxane metal complexes by the reaction of trisilanol, which is substituted by cyclohexyl groups, with a metal compound, is known (Polyhedron, 1995, vol. 14, No. 22, pages 3239-3253).
The synthesis of a trisilanol, containing cyclohexyl groups, is very time consuming. This trisilanol is, however, readily soluble, so that the reaction to the desired metal complexes is readily possible.
A trisilanol, which is substituted by cyclopentyl groups, can be synthesized in a much shorter time. However, the trisilanol is not very soluble, so that the synthesis of the corresponding metal complexes has not previously been described.
The previously known methods for the synthesis of the metal complexes are very time consuming and require large amounts of solvents, which must be worked up once again.
The use of titanium containing metal complexes as catalysts for the synthesis of epoxide compounds by the oxidation of unsaturated hydrocarbons is also known. For example, the WO 97/24344 discloses a method for the oxidation of olefinically unsaturated hydrocarbons, for which titanium silasesquioxane catalysts are used. However, this method is limited to organic hydroperoxides as oxidizing agents and can be carried out only in anhydrous organic solvents. The titanium atoms in the titanium silasesquixoane catalysts used are tetrahedrally coordinated four fold.
SUMMARY OF THE INVENTION
It is an object of the invention to provide a method for the synthesis of silasesquioxane metal complexes, with which the silasesquioxane metal complexes, which previously were accessible only with difficulty if at all, can be made available.
It is a further object of the invention to make the silasesquioxane metal complexes available as catalysts, which are also stable and catalytically active in aqueous media, for the oxidation of unsaturated hydrocarbons or alcohols, since in this way environmentally-friendly oxidizing agents, such as oxygen or hydrogen peroxide, can be used, for example, for the epoxidation of alkene compounds.
The object of the invention is achieved due to the fact that the reaction of the metal compounds with a silasesquioxane with a defined denticulation takes place in a suspension.
Pursuant to the invention, halides, especially chlorides, C.sub.1 to C.sub.20 alkyl or aryl compounds, which do not contain a beta hydrogen atom, such as methyl, benzyl, neopentyl, xylyl, mesityl, neophil and/or adamantyl compounds, silyl, fluorenyl, indenyl and/or cyclopentadienyl compounds, it being possible for the individual ligands to be substituted by C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkylsilyl, alkoxy, aryl or arylsilyl groups, oxides, imides, amides, alkoxides (such as --OR, in which R is hydrogen, C.sub.1 to C.sub.20 alkyl, especially methyl, ethyl, isopropyl, t-butyl, aryl, especially benzyl, phenyl, toluyl, naphthyl, xylyl) or mixed compounds of these, such as oxohalides, aryl or alkyl halides, halogen amides or alkylalkoxides of the metals of the 4.sup.th to the 7.sup.th subgroups of the Periodic Table of the Elements and at least one silasesquioxane of the general formula I (B).sub.q (O).sub.r)) cyclohexyl, cycloheptyl, norbornyl, adamantyl to C.sub.4 alkyl, especially methyl, aryl, particularly phenyl or SiMe.sub.2 (CH.sub.2).sub.s CH.dbd.CH.sub.2, SiMe.sub.2 (CH.sub.2).sub.s CH.sub.2 CH.sub.2 A, SiMe.sub.2 (CH.sub.2).sub.s CHACH.sub.3, wherein A represents OH, COOH, NH.sub.2, SO.sub.3 --, COO-- and s represents 1 to 20, hydrocarbon, optionally in the presence of a basic compound, with stirring at -80.degree. C. to +110.degree. C. and the reaction product is removed at room temperature.
Metals, within the sense of the invention, are understood to include, in particular, titanium, zirconium, hafnium, chromium, tungsten, molybdenum, vanadium, niobium, tantalum and rhenium; titanium, vanadium or zirconium being preferred.
As m
REFERENCES:
Buys et al, Journal of Molecular Catalysis, 86, pp. 309-315, 1994.
Feher et al, Polyhedron, 14(22), pp. 3239-3253, 1995.
Winkhofer et al, Angew. Chem. Ind. Eng., Engl. Commun., 33(13), pp. 1352-1354, 1994.
Abbenhuis Hendrikus Cornesis Louis
Van Santen Rutger Anthony
Vorstenbosch Martinus Lambertus Wilhelmus
Solvay Deutschland GmbH
Trinh Ba K.
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