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US5155247.Pdf ||||||||||||||| USOO555247A United States Patent (19) 11 Patent Number: 5,155,247 Herrmann et al. 45 Date of Patent: Oct. 13, 1992 54 USE OF ORGANORHENIUM COMPOUNDS Unsaturated Substances', The Journal of the American FOR THE OXIDATION OF MULTIPLE Society, vol. 59, 1937, pp. 2345-2347. C-C-BONDS, OXIDATION PROCESSES Milas, N. A., and Sussman, S., "The Hydroxylation of BASED THERON AND NOVEL the Double Bond' The Journal of the American Soci ORGANORHENUM COMPOUNDS ety vol. 58, 1936, pp. 1302–1304. 75 inventors: Wolfgang A. Herrmann, Giggenhausen; Dieter M. Primary Examiner-Patrick P. Garvin Fritz-Meyer-Weg, Munich; Werner Assistant Examiner-E. D. Irzinski Wagner, Munich; Josef G. Kuchler, Attorney, Agent, or Firm-Connolly and Hutz Munich; Georg Weichselbaumer, 57 ABSTRACT Hoenwart; Richard Fischer, Gross karolinenfeld, all of Fed. Rep. of Compounds of the formula Germany 73) Assignee: Hoechst Aktiengesellschaft, (RRe)O1R12-L. (III) Frankfurt am Main, Fed. Rep. of in which Germany R is a hydrocarbon group which is bonded to the rhenium via a carbon atom to which at least one 21) Appl. No.: 470,086 hydrogen atom is still attached, 22 Filed: Jan. 25, 1990 R2 is aliphatic hydrocarbon radical which may contain 30 Foreign Application Priority Data silicon bridge atoms, or is an unsubstituted or substi tuted phenyl radical, Jan. 27, 1989 (DE) Fed. Rep. of Germany ....... 3902357 L is a ligand which is bonded to the rhenium metal via 51) Int. Cl. .............................................. CO7F 13/00 one to three oxygen and/or nitrogen atoms, and the 52 U.S. Cl. ............... ... 556/46; 502/167 index k is or 2, the index 1 is an integer from 1 to three 58 Field of Search .......................................... 556/46 times k, the index m is zero or an integer from 1 to twice k, and the index n is an integer from 1 to three 56) References Cited times k, and in which the indices k, l, m and n are selected such that their combination satisfies the 5-, 6 U.S. PATENT DOCUMENTS or 7-valence of rhenium. 3,316,279 4/1967 Fenton ............................. 260/348.5. The invention also provides compounds of the formula 3,58,285 6/1970 Fenton et al. ... 260/348.5 4,090,978 5/1978 Welsh et al. ...................... 502/59 (polymer)a(CH3ReO3)s (VI) FOREIGN PATENT DOCUMENTS 89122437 6/1989 European Pat. Off. in which the rhenium compound CH3ReO3 is bonded to the polymer via amine or amide nitrogen in the poly OTHER PUBLICATIONS mer. It further provides for the use of compounds of the S. Pummel and D. Schnurpfeil, Technetium compounds formula RaRebOc (I) in which a is 1 to 6, b is 1 to 4 and as Catalysts in Hydroperoxide Decomposition and Epoxi c is 1 to 14 and the total of a, b and c is such that the dation Processes, Oxidation Communication, vol. 6, Nos. 1-4 pp. 319-329. 5-valence to 7-valence of rhenium is satisfied, with the Schmidt, M. and Schmidbauer, H.; Trimethylsilylperr proviso that c is not greater than three times b, and in henat Chem. Ber. 92 (1959) pp. 2667-2669. which R represents an optionally fluorinated hydrocar Schmidbaur, M. and Koth, D; Chem. Zeitung 100 bon, or of compounds of the formula (RIRe)- (1976) pp. 290-291. ROR12m-Lin (III) or (polymer)f(CH3ReO3) (VI), as Herrmann, Wolfgang; Methylrhenium Oxides: Synthesis catalysts for the oxidation of multiple C-C bonds and from R2O, and Catalytic Activity in Olefin Methanesis, also provides processes of this type. Angewandle Chemie. 100 (1988) pp. 420-422. Milas, N. A. and Sussman, S., "The Hydroxylation of 8 Claims, No Drawings 5,155,247 1. 2 tive or unselective in the oxidation of olefins. Only two USE OF ORGANORHENIUM COMPOUNDS FOR very similar reports appear in the literature concerning THE OXIDATION OF MULTIPLE C-C-BONDS, the use of rhenium compounds, in particular rhenium OXDATION PROCESSES BASED THERON AND oxides, rhenium halides and perrhenates, as catalysts for NOVEL ORGANORHENIUM COMPOUNDS oxidation with oxygen at -50 to +125° C. (U.S. Pat. No. 3,316,279) and with hydrogen peroxide at . DESCRIPTION 100-150° C. (U.S. Pat. No. 3,518,285). In both cases, The use of organorhenium compounds for the oxida mixtures of epoxides and ketones were obtained. The tion of multiple C-C-bonds, oxidation processes based oxidation with oxygen according to U.S. Pat. No. thereon and novel organorhenium compounds O 3,316,279 can also employ "oxidation modifiers", The invention relates to the use of certain organor namely nitrogenous compounds, in particular organic henium compounds for the oxidation of multiple C-C cyanides, pyridines and quinolines which are intended bonds, oxidation processes based thereon, in particular to halt the reaction to a certain extent at the epoxide for the preparation of epoxides and optionally diols by stage and to suppress rearrangements; if they are left oxidation of olefinic compounds and for the preparation 5 out, consequent reactions occur such as the formation of diketones or ol,(3-olefinically unsaturated monoke of condensation products (by dimerization of the epox tones by oxidation of alkynes, in each case with hydro gen peroxide using organorhenium compounds, and to ides to form substituted dioxanes or polymerization to novel organorhenium compounds. form polyethers) and the formation of a-hydroxycarbo It is known that metal oxides act selectively as oxidiz 20 nyl compounds by further oxidation of the epoxides. ing agents for unsaturated organic compounds of differ Moreover, the process according to U.S. Pat. No. ent categories. For instance, the binary oxides MO6 of 3,316,279 is intended to be carried out at pressures from the metals (M) vanadium (V2O5), molybdenum (MoC3) 1 to about 250 atmospheres, i.e. operation at elevated and osmium (OsO4) in particular are used in practice, pressure is virtually obligatory, as can also be seen from for example as catalysts for converting olefins into ep 25 the examples. However, reactions under elevated pres oxides. In these reactions, 1,2-diol derivatives can also sure require increased expenditure on plant. be produced, and in the case of OsO4, the cis-glycols Applicant's own attempts to use the abovementioned can be produced stereospecifically. These metal oxides rhenium oxides, for example Re2O7 and ReO3, as cata are often not used as stoichiometric reagents but in the lysts for olefin oxidation were likewise unsuccessful. presence of hydrogen peroxide, tert-butyl hydroperox 30 Similarly, Na(ReO4), NH4(ReO4) and N(n- ide, m-chloroperbenzoic acid and so on in only catalytic C4H9)4ReO4} proved ineffective, as did organometal amounts. Although the reaction mechanisms are not lic mixed compounds such as the monomeric derivative known in detail, the action of catalyst systems of this (trimethylstannoxy)rheniumtrioxide of the formula type (for example metal oxide/H2O2) is ascribed to (CH3)3SnOReO3 described by W. A. Herrmann et hydroperoxo-metal completes as the actually effective 35 al.(W. A. Hermann, J. G. Kuchler, J. K. Felixberger, E. catalyst species (structural unit M-O-OH). Herdtweck and W. Wagner, Angew. Chem. 100 (1988) The catalyst system OsO4/H2O2 has particular im 420-422) and the compounds (CH3)3SiOReO3 (M. portance for the selective oxidation of olefins to form Schmidt and H. Schmidbaur, Chem. Ber. 92 (1959) cis-1,2-diols. In this case, catalytic amounts of osmium 2,667-2,669) and (C6H5)3SiO)ReO3 (H. Schmidbaur tetroxide are sufficient. A particularly well known rea and D. Koth, Chem. Zeitung 100 (1976) 290-291). gent is Milas' reagent: H2O2/tert-butanol/OsO4 (N. A. It is known from the paper by W. A. Herrmann et al., Milas and S. Sussaman, J. Am. Chem. Soc. 58 (1936) loc. cit., that of the true organometallic compounds of 1,302-04 and N. A. Milas and S. Sussaman J. Am. rhenium, methylrhenium trioxide CH3ReO3 in the pres Chem. Soc. 59 (1937) 2,345-47). ence of AlCl3 and tetramethyltin brings about the me However, in this connection, the abovementioned 45 metal oxides also have disadvantages, in particular high tathesis of open-chain olefins and also the catalytic ring cost (osmium), high toxicity (osmium), lack of selectiv opening polymerization of cycloolefins to form po ity for the formation of epoxides and cis-1,2-diols from lyalkenamers. The same paper discloses that methylr the olefinic precursors (chronium, molybdenum, tung henium oxide is methylated by treatment with dimethyl sten) and the short life of the catalyst under the given 50 zinc to form a sublimable, lemon-yellow methylrhenium reaction conditions (in particular, OsO4/H2O2/tert oxide of the formula (CH3)4Re2O4, i.e. a compound butanol). containing 6-valent rhenium. This compound too, in the The object is therefore to provide a simple-to-handle, presence of tetramethyltin and aluminum chloride, cata storable, non-toxic and effective catalyst system which lyzes the metathetic ring-opening polymerization of ideally is easily accessible and which achieves the de 55 cyclopentene. sired selectivity in the oxidation of olefins and certain Finally, the above paper discloses that (CH3)4Re2O4 alkynes. 1,2-Diols and epoxides are of great interest for is converted by further methylation with dimethylzinc further industrial processing and so are 1,2-diketones to (CH3)6.Re2O3, i.e. likewise to a compound containing and af3-olefinically unsaturated monoketones. 6-valent rhenium. According to said paper, this com The obvious idea of using, instead of the oxidation pound is capable of catalyzing the ring-opening poly catalysts known from the literature, oxides of the ele merization of cyclopentene even in the presence only of ment rhenium which is adjacent to osmium and molyb AlCl3, i.e.
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