Liquid Phase Epoxidation Patents (Class 549/524)
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Patent number: 6770766Abstract: The invention relates to a novel process that makes it possible to epoxidize &agr;,&bgr;-unsaturated enones or &agr;,&bgr;-unsaturated sulfones with high conversions and enantiomeric excesses in the presence of a water-soluble base, an oxidant, a diastereomer- and enantiomer-enriched homo-polyamino acid as catalyst, water, an organic solvent that is immiscible or has only limited miscibility with water, and a specific phase-transfer catalyst as cocatalyst.Type: GrantFiled: July 24, 2002Date of Patent: August 3, 2004Assignee: Bayer Chemicals AGInventors: Thomas Geller, Christa Maria Krüger, Hans-Christian Militzer
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Publication number: 20040138481Abstract: A continuous and scalable process for producing glycidyl nitrate, or glyn, from glycerin, nitric acid, and caustic wherein the process includes the reaction of glycerin and nitric acid to form dinitroglycerin and the reaction of dinitroglycerin with caustic, such as sodium hydroxide, to produce glycidyl nitrate. A system for producing the inventive material is also disclosed. The system includes a first reaction vessel, a second reaction vessel, and a separation apparatus.Type: ApplicationFiled: January 10, 2003Publication date: July 15, 2004Inventors: Thomas K. Highsmith, Harold E. Johnston
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Patent number: 6743748Abstract: The present invention provides a catalyst capable of producing an epoxy compound in high yield and improving the utilization efficiency of the oxidizing agent as well as a method of producing an epoxy compound using that catalyst. A catalyst for producing an epoxy compound by oxidizing a compound having at least one ethylenic double bond with an oxidizing agent, comprising a polyatom-containing heteropolyoxometalate anion (A1) having two defective and/or three defective structure sites and containing silicon as the heteroatom, and an element (E1) being at least one element selected from the group consisting of vanadium, tantalum, niobium, antimony, bismuth, chromium, molybdenum, selenium, tellurium, rhenium, cobalt, nickel, ruthenium, rhodium, palladium, osmium, platinum, iridium, silver, gold, zinc, aluminum, gallium, indium, scandium, yttrium, titanium, zirconium, hafnium, germanium, tin and lanthanoids, and being different from the polyatom.Type: GrantFiled: March 7, 2003Date of Patent: June 1, 2004Assignee: Nippon Shokubai Co., Ltd.Inventors: Noritaka Mizuno, Yasutaka Sumida, Koji Yonehara, Masahiro Wada, Minoru Urata
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Patent number: 6700004Abstract: The invention relates to a novel process that makes it possible to epoxidize &agr;,&bgr;-unsaturated enones or &agr;,&bgr;-unsaturated sulfones with high conversions and enantiomeric excesses in the presence of a water-soluble base, an oxidant, water, an organic solvent that is immiscible or has only limited miscibility with water, a preactivated diastereomer- and enantiomer-enriched homo-polyamino acid as catalyst, and a specific phase-transfer catalyst as cocatalyst.Type: GrantFiled: July 24, 2002Date of Patent: March 2, 2004Assignee: Bayer AktiengesellschaftInventors: Thomas Geller, Christa Maria Krüger, Hans-Christian Militzer
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Patent number: 6686483Abstract: The present invention provides a variety of methods that are based on stereoselective epoxidation of an olefin by an epoxidizing agent derived from a reaction between an oxidizing agent and a chiral ketone. For example, present invention provides methods for producing an epoxide from an olefin, for increasing a relative concentration of at least one stereoisomer of an olefin, and for stereoselectively producing an &agr;-acyloxy carbonyl compound. Preferably, the chiral ketone is of the formula: or a derivative thereof which is capable of converting to the chiral ketone of Formula I under the reaction conditions, where a, b, n, X, R1, R2, R3, R4, R5 and R6 are those defined herein.Type: GrantFiled: January 7, 2002Date of Patent: February 3, 2004Assignee: Colorado State University Research FoundationInventor: Yian Shi
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Patent number: 6653419Abstract: A method for producing partially fluorinated epoxides and corresponding polyether homopolymers of these polyfluorinated epoxides is described. Also described is a method for incorporating a fluoroalcohol functional group into a polymer as a pendant group. Certain perfluorinated olefins are also described. These polyfluorinated epoxides and the associated polymers and methods relating to them are useful components in photoresists, particulary in lithographic photoresists for use at low ultraviolet wavelengths (e.g., 157 nm).Type: GrantFiled: October 3, 2001Date of Patent: November 25, 2003Assignee: E. .I du Pont de Nemours and CompanyInventors: Viacheslav Alexandrovich Petrov, Andrew Edward Fiering, Jerald Feldman
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Patent number: 6608219Abstract: A process for the catalytic epoxidation of olefins with hydrogen peroxide in a multiphase reaction mixture comprising a liquid aqueous hydrogen peroxide rich phase containing an organic solvent having a solubility in water of at least 10% by weight at 25° C. and a liquid organic olefin rich phase.Type: GrantFiled: June 13, 2002Date of Patent: August 19, 2003Assignees: Degussa AG, Uhde GmbHInventors: Thomas Haas, Willi Hofen, Georg Thiele, Stefan Pilz, Wolfgang Woell
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Patent number: 6605733Abstract: Provided are a titanium-containing solid catalyst useful for producing an epoxy compound from an olefin compound and a peroxide, and a process for producing an epoxy compound using said catalyst. The titanium-containing solid catalyst is obtainable by calcination of a titanium alkynyl alkoxide supported on a silica gel.Type: GrantFiled: December 28, 2001Date of Patent: August 12, 2003Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Hideki Omori, Hiroko Ahara, Kazuhiko Haba, Yoshiaki Takaya, Shin Irie
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Publication number: 20030087401Abstract: The invention relates to a novel process that makes it possible to epoxidize &agr;,&bgr;-unsaturated enones or &agr;,&bgr;-unsaturated sulfones with high conversions and enantiomeric excesses in the presence of a water-soluble base, an oxidant, a diastereomer- and enantiomer-enriched homo-polyamino acid as catalyst, water, an organic solvent that is immiscible or has only limited miscibility with water, and a specific phase-transfer catalyst as cocatalyst.Type: ApplicationFiled: July 24, 2002Publication date: May 8, 2003Inventors: Thomas Geller, Christa Maria Kruger, Hans-Christian Militzer
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Patent number: 6559283Abstract: Poly-&bgr;-amino acids and their use in catalytic organic reactions, especially in epoxidation procedures, are provided.Type: GrantFiled: June 14, 2001Date of Patent: May 6, 2003Assignee: Degussa AGInventors: Karlheinz Drauz, Olaf Burkhardt, Stan M. Roberts, John Skidmore, Paul Coffey
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Publication number: 20030064486Abstract: The invention relates to a novel process that makes it possible to epoxidize &agr;,&bgr;-unsaturated enones or &agr;,&bgr;-unsaturated sulfones with high conversions and enantiomeric excesses in the presence of a water-soluble base, an oxidant, water, an organic solvent that is immiscible or has only limited miscibility with water, a preactivated diastereomer- and enantiomer-enriched homo-polyamino acid as catalyst, and a specific phase-transfer catalyst as cocatalyst.Type: ApplicationFiled: July 24, 2002Publication date: April 3, 2003Inventors: Thomas Geller, Christa Maria Kruger, Hans-Christian Militzer
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Patent number: 6534661Abstract: The invention discloses a dual-functional catalyst composition and an integrated process for production of olefin epoxides including propylene oxide by catalytic reaction of hydrogen peroxide from hydrogen and oxygen with olefin feeds such as propylene. The epoxides and hydrogen peroxide are preferably produced simultaneously in situ. The dual-functional catalyst comprises noble metal crystallites with dimensions on the nanometer scale (on the order of <1 nm to 10 nm), specially dispersed on titanium silicalite substrate particles. The dual functional catalyst catalyzes both the direct reaction of hydrogen and oxygen to generate hydrogen peroxide intermediate on the noble metal catalyst surface and the reaction of the hydrogen peroxide intermediate with the propylene feed to generate propylene oxide product.Type: GrantFiled: November 30, 2001Date of Patent: March 18, 2003Assignee: Hydrocarbon Technologies, Inc.Inventors: Bing Zhou, Michael Rueter
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Patent number: 6525208Abstract: Mixed together are (i) hydrogen peroxide; (ii) 1-alkene; (iii) quaternary ammonium salt wherein at least one of the substituents contains at least six carbon atoms; (iv) boric acid, or both a 1,2-diol and boric acid; and (v) a preformed catalyst solution formed from hydrogen peroxide, at least one aqueous inorganic acid, and at least one tungstate salt, while water is continuously removed, such that a 1,2-epoxide is formed. A new method for purifying 1,2-epoxyalkanes is also described.Type: GrantFiled: April 3, 2002Date of Patent: February 25, 2003Assignee: Albemarle CorporationInventors: Chi Hung Cheng, Gerald M. Sulzer
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Publication number: 20020133031Abstract: The present invention provides a variety of methods that are based on stereoselective epoxidation of an olefin by an epoxidizing agent derived from a reaction between an oxidizing agent and a chiral ketone. For example, present invention provides methods for producing an epoxide from an olefin, for increasing a relative concentration of at least one stereoisomer of an olefin, and for stereoselectively producing an &agr;-acyloxy carbonyl compound.Type: ApplicationFiled: January 7, 2002Publication date: September 19, 2002Applicant: Colorado State University Research FoundationInventor: Yian Shi
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Patent number: 6429322Abstract: Process for manufacturing an epoxide by reaction between an olefin and a peroxide compound in the presence of a zeolite-based catalyst and in the presence of a solvent, in which the pH of the reaction medium comprising the olefin, the peroxide compound, the catalyst, the epoxide formed and the solvent is from 4.8 to 6.5.Type: GrantFiled: September 22, 2000Date of Patent: August 6, 2002Assignee: Solvay SAInventors: Jean-Pierre Catinat, Michel Strebelle
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Patent number: 6423853Abstract: Continuous processes for converting cycloalkenes into ozonides in which ozone is reacted with a cycloalkene to form an ozonide solution. A portion of the solution is recycled back to the reaction, and additional cycloalkene is provided.Type: GrantFiled: September 24, 2001Date of Patent: July 23, 2002Assignee: E. I. du Pont de Nemours & Comp.Inventors: Edward F. Moran, Jr., Chester Arthur Thayer, II
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Patent number: 6414168Abstract: Unsaturated or polyunsaturated, conjugated or nonconjugated hydrocarbons are reacted with an oxidizing agent including hydroperoxides and monopersulfate compounds in the presence of phase-transfer catalysts. Suitable hydrocarbons include ricinic compounds such as castor oil and dehydrated castor oil. The phase-transfer catalysts include novel tungsten peroxo complexes, such as quaternary ammonium tetrakis (diperoxotungsto) phosphates, and crown ethers. Other additives utilized include pH buffers and alkaline compounds including alkali metal and alkaline earth metal carbonates, and solvents.Type: GrantFiled: December 28, 1999Date of Patent: July 2, 2002Assignee: CasChem, Inc.Inventors: James V. Crivello, Srinivasan Chakrapani
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Patent number: 6403815Abstract: The liquid-phase epoxidation reaction of an olefin with hydrogen and oxygen in the presence of a catalyst mixture comprising titanium zeolite and a supported catalyst surprisingly shows higher activity toward epoxide production when the supported palladium catalyst is pre-treated with bromide, or where the reaction is performed in the presence of an alkali or alkaline earth metal bromide compound.Type: GrantFiled: November 29, 2001Date of Patent: June 11, 2002Assignee: Arco Chemical Technology, L.P.Inventor: Roger A. Grey
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Patent number: 6348608Abstract: A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.Type: GrantFiled: April 6, 1999Date of Patent: February 19, 2002Inventor: Yian Shi
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Patent number: 6307073Abstract: A catalyst mixture containing a titanium zeolite and a supported gold-containing catalyst is highly selective and productive for transforming olefins to epoxides in the liquid-phase reaction of an olefin, hydrogen, and oxygen. This is particularly surprising because neither titanium zeolite nor the supported gold-containing catalyst alone is effective in olefin epoxidation.Type: GrantFiled: July 25, 2000Date of Patent: October 23, 2001Assignee: ARCO Chemical Technology, L.P.Inventor: C. Andrew Jones
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Patent number: 6288248Abstract: Epichlorohydrin-based product containing at least 99.9% by weight of epichlorohydrin and a total amount of chloro impurities of less than or equal to 150 ppm by weight, and process for manufacturing this product by reaction of allyl chloride with a peroxide compound in the presence of water, a catalyst and a diluent in at least one reactor, and separation of the epichlorohydrin formed.Type: GrantFiled: November 25, 1998Date of Patent: September 11, 2001Assignee: Solvay (Société Anonyme)Inventors: Michel Strebelle, Patrick Gilbeau, Jean-Pierre Catinat
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Patent number: 6225482Abstract: A process for the enantioselective epoxidation of C═C double bonds and use of the epoxides. The present invention provides a process for the enantioselective epoxidation of compounds of the formula I by means of a diastereomer and enantiomer enriched homopolyamino acid and an oxidizing agent. The epoxides prepared according to the invention are used as intermediates in organic syntheses.Type: GrantFiled: November 30, 1999Date of Patent: May 1, 2001Assignee: Degussa-Huls AktiengesellschaftInventors: Karlheinz Drauz, Stan M. Roberts, John Skidmore
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Patent number: 6160137Abstract: A method for producing propylene oxide by reacting a hydroperoxide with propylene by a fixed bed flow reaction in the presence of a titanium-containing solid catalyst, wherein said catalyst is diluted with a diluent comprising a solid inorganic compound which is inactive to the reaction and has a heat conductivity at 400 K of about 10 Wm.sup.-1 K.sup.-1 or more.Type: GrantFiled: November 5, 1998Date of Patent: December 12, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Junpei Tsuji, Masaru Ishino, Kenshi Uchida
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Patent number: 6087513Abstract: A process for making an aromatic glycidyl ether epoxy compound by contacting an allyl ether made from the hydroxy moiety of a hydroxy-containing aromatic compound with an inorganic or organic hydroperoxide oxidant in the presence of a transition metal complex catalyst, wherein at least (a) the allyl ether is conformationally restricted or (b) the transition metal complex catalyst contains at least one or more stable ligands attached to the transition metal. The process of the present invention provides for epoxidizing aryl allyl ethers with high epoxidation yield (for example, greater than 70% to 90%) and high hydroperoxide selectivity (for example, greater than 70% to 90%).Type: GrantFiled: May 21, 1999Date of Patent: July 11, 2000Assignee: The Dow Chemical CompanyInventors: Zeng K. Liao, Clinton J. Boriack
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Patent number: 6087514Abstract: Disclosed are novel crystalline molecular sieves having the framework of ETS-10 titanium silicate which contain both octahedral and tetrahedral titanium atoms and are in acid form. The sieves are prepared by adding a complexing agent such as hydrogen peroxide during synthesis or by treating a synthesized titanium silicate molecular sieve with a reagent that replaces tetrahedral silicon with tetrahedral titanium atoms.Type: GrantFiled: October 20, 1998Date of Patent: July 11, 2000Assignee: Engelhard CorporationInventors: Appadurai Thangaraj, Steven M. Kuznicki, Gerald S. Koermer
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Patent number: 6087299Abstract: The present invention relates to silver-containing and optionally promoter-containing supported catalysts and catalyst intermediates, processes for their preparation and their use for preparing alkylene oxides by oxidation of alkenes with oxygen. The catalysts are prepared by treatment of a support with a lactic acid containing silver ions, nitrate ions and optionally promoter metal ions, drying, predecomposition in a virtually oxygen-free atmosphere and subsequent activation by heating in an oxygen-containing atmosphere while precisely controlling the temperature conditions and the feeding-in of oxygen. The catalyst intermediates obtainable by treatment, drying and only predecomposition can be activated in a temporally and physically separate process step to form the actual catalysts. Suitable promoters are alkaline earth metal compounds and/or alkali metal compounds. High activities and high selectivities are achieved when using the catalysts of the invention for preparing alkylene oxides.Type: GrantFiled: January 26, 1999Date of Patent: July 11, 2000Assignee: EC Erdolchemie GmbHInventors: Joachim Grub, Werner Volprecht, Matthias Baum, Alfred Reimer
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Patent number: 6066750Abstract: Propylene is converted to propylene oxide in a highly efficient liquid phase process wherein temperature and pressure are both increased over the course of the epoxidation, which is preferably conducted in a continuous mode of operation. The catalyst used is a heterogeneous catalyst such as titanium silicalite or titania-on-silica. The oxidizing agent is an active oxygen species such as hydrogen peroxide or an organic hydroperoxide. When the desired yield of propylene oxide can no longer be maintained, the catalyst is replaced or regenerated. Regeneration by washing the catalyst with a hot solvent containing a source of ammonium or alkali metal cations is highly effective, especially where the catalyst is a titanium-containing zeolite.Type: GrantFiled: December 30, 1998Date of Patent: May 23, 2000Assignee: Arco Chemical Technology, L.P.Inventor: Te Chang
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Patent number: 6063944Abstract: A method is provided for preparing fully lattice-inserted titanium zeolites by post-synthesis processing of the synthetic zeolite optionally containing titanium with an inorganic acid, wherein the post-synthesis processing comprises processing the zeolite in the presence of at least one titanium source with a solution containing at least one oxidizing inorganic acid having a higher redox potential than an acidic tetravalent titanium solution. The invention is also directed to the use of the zeolites.Type: GrantFiled: May 4, 1998Date of Patent: May 16, 2000Assignee: Elf AquitaineInventors: Francesco Di Renzo, Sylvie Gomez, Francois Fajula, Remy Teissier
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Patent number: 6051725Abstract: Unsaturated or polyunsaturated, conjugated or nonconjugated hydrocarbons are reacted with an oxidizing agent including hydroperoxides and monopersulfate compounds in the presence of phase-transfer catalysts. Suitable hydrocarbons include ricinic compounds such as castor oil and dehydrated castor oil. The phase-transfer catalysts include novel tungsten peroxo complexes, such as quaternary ammonium tetrakis (diperoxotungsto) phosphates, and crown ethers. Other additives opionally utilized include pH buffers, alkaline compounds, and solvents.Type: GrantFiled: December 28, 1998Date of Patent: April 18, 2000Assignee: Caschem, Inc.Inventors: James V. Crivello, Srinivasan Chakrapani
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Patent number: 6008386Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.Type: GrantFiled: July 22, 1997Date of Patent: December 28, 1999Assignee: Board of Regents University of Nebraska-LincolnInventors: David B. Berkowitz, Michelle L. Pedersen
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Patent number: 5916430Abstract: The preparation of epoxides of the general formula I ##STR1## in which the substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 are independently hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, C.sub.1 -C.sub.20 -hydroxyalkyl, a heterocyclic ring, or an aryl or C.sub.7 -C.sub.20 -arylalkyl group optionally substituted by C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, phenyl, phenoxy, halophenyl, halophenoxy, carboxy, C.sub.2 -C.sub.8 -alkoxycarbonyl, or cyano, or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 or R.sup.1 and R.sup.4 or R.sup.3 and R.sup.4 or R.sup.4 and R.sup.5 together form a (CH.sub.2).sub.n group in which n is an integer from 1 to 10 and which may be optionally substituted by C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, and/or halogen, andR.sup.6 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: September 7, 1993Date of Patent: June 29, 1999Assignee: BASF AktiengesellschaftInventor: Dieter Haermeling
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Patent number: 5792878Abstract: A process for preparing chiral epoxides using chiral manganese triazanonane complexes as oxidation catalysts. These catalysts have the general formula?Mn.sub.u (L).sub.v (OR).sub.w (.mu.O).sub.x (.mu.OAc).sub.y !X.sub.Type: GrantFiled: June 28, 1996Date of Patent: August 11, 1998Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Ahmed Tafesh, Richard Walter Fischer, Bernd Scharbert
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Patent number: 5705660Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.Type: GrantFiled: August 22, 1994Date of Patent: January 6, 1998Assignee: Board of Regents, University of Nebraska-LincolnInventors: David B. Berkowitz, Michelle L. Pedersen
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Patent number: 5663393Abstract: Chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed, together with methods of using such catalysts. In accordance with one aspect of the invention, the catalyst is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of, producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.Type: GrantFiled: June 6, 1995Date of Patent: September 2, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
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Patent number: 5637739Abstract: Methods of using chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed. In accordance with one aspect of the invention, the catalyst used is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.Type: GrantFiled: October 15, 1992Date of Patent: June 10, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
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Patent number: 5621118Abstract: A process for oxidizing a substrate susceptible to nucleophilic oxidation by reacting a bicaroate or monopersulfate solution with the substrate is disclosed. In one aspect, the substrate is introduced into the reaction mixture in an inert carrier gas, which can also serve to sweep the product out of the mixture. In a second aspect the oxidation solution is obtained by a two stage neutralization of a Caro's acid solution, the first stage to e.g. 0.5 to 2.0 and the second stage to about 7 to 9. In preferred embodiments, the substrate is introduced into partially neutralized Caro's acid, and the second stage neutralization in the presence of the substrate is most preferably carried out with an alkali salt such as sodium bicarbonate. The process can employ relatively low ratios of substrate: Caro's acid oxidant and homogeneous reaction conditions. The process is particularly useful for preparing dioxiranes from ketones.Type: GrantFiled: April 14, 1994Date of Patent: April 15, 1997Assignee: Solvay Interox LimitedInventors: Craig W. Jones, William R. Sanderson, John P. Sankey
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Patent number: 5578744Abstract: A catalytically active gel is described consisting of a silica matrix with uniform porosity, monomodal pore distribution and high surface area, within which one or metal oxides possessing catalytic activity are dispersed. A process for preparing this catalytic gel is also described.Type: GrantFiled: May 19, 1995Date of Patent: November 26, 1996Assignees: Eniricerche S.p.A., Snamprogetti S.p.A.Inventors: Angela Carati, Enrico Davini, Mario G. Clerici, Giuseppe Bellussi
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Patent number: 5428180Abstract: A method is provided for oxidizing alkenes to epoxides by treating the alkene with a transition metal ion complex which includes a salen or salophen derivative and peroxymonosulfate ion or hypochlorite ion in a two phase system with a phase transfer catalyst, a water phase having a pH from about 6 to about 12.9 and an inorganic solvent phase in which the complex is sufficiently soluble.Type: GrantFiled: December 10, 1993Date of Patent: June 27, 1995Assignee: The Research Foundation of State University of New YorkInventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
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Patent number: 5329024Abstract: A method for epoxidizing olefins is provided wherein an olefin and an oxygenating agent are contacted together in the presence of a manganese complex catalyst having at least one manganese atom coordinated with a nitrogen-containing ligand such that the manganese atom to coordinated nitrogen atom is 1:3 and thereafter isolating the resultant epoxide product. Catalyst compositions are also provided formed from the adsorption of the manganese complex catalyst onto a solvent insoluble support.Type: GrantFiled: March 30, 1993Date of Patent: July 12, 1994Assignee: National Starch and Chemical Investment Holding CorporationInventors: Sharon H. Jureller, Judith L. Kerschner, Robert Humphreys
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Patent number: 5268489Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.Type: GrantFiled: February 5, 1993Date of Patent: December 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
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Patent number: 5227501Abstract: Disclosed is a novel fluorine-containing epoxide compound 6-iodo-undecafluoro-1,2-epoxy hexane which can be prepared by the epoxidation reaction of 6-iodo-undecafluoro-1-hexene with a hypochlorite such as sodium hypochlorite in a two-phase reaction system consisting of an organic phase and an aqueous phase in the presence of a quaternary ammonium compound as the catalyst.Type: GrantFiled: May 12, 1992Date of Patent: July 13, 1993Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Shinichi Sato, Yasuo Tarumi, Takashi Matsuda, Hiromasa Yamaguchi
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Patent number: 5126464Abstract: A 13 or 14 member macrocyclic compound having the following ring nucleus: ##STR1## wherein: n=0 or 1;m=0 or 1;n+m>0;X.sub.1, X.sub.2, Z.sub.1 and Z.sub.2 independently represent H.sub.2 or O;Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 independently represent H, lower alkyl or CH.sub.2 COOH;L.sub.1 and L.sub.2 independently represent side chains of alpha amino acids, except that L.sub.1 and L.sub.2 do not both represent H; andR.sub.1 and R.sub.2 independently represent H or OH forms stable complexes with transition metal ions that may be used as catalysts for oxidizing alkenes to epoxides with oxidizing agents.Type: GrantFiled: October 29, 1990Date of Patent: June 30, 1992Assignee: The Research Foundation of State University of New YorkInventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
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Patent number: 5084583Abstract: The synthesis of epoxides from fluorine containing olefins using elemental fluorine in mixtures of water and acetonitrile is disclosed.Type: GrantFiled: January 9, 1991Date of Patent: January 28, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Shlomo M. Rozen, Bruce E. Smart
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Patent number: 5077394Abstract: Disclosed are tetraphenyl porphyrins which are beta-substituted by fluoro or chloro and/or bear electronegative substituents on the phenyl including one or two water solubilizing substituents. The new porphorins are particularly suitable as catalysts in a variety of oxidative reactions and methods.Type: GrantFiled: December 21, 1989Date of Patent: December 31, 1991Assignee: Sandoz Ltd.Inventors: David H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
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Patent number: 4985230Abstract: A catalytic chemical process is carried out non-adiabatically using as a catalyst a body with two sets of channels throughout the body. One set of channels leads the process fluid towards one of two parallel walls of the catalyst chamber, the other set towards the outer wall, In slits between walls and catalyst heat is exchanged between process fluid and at least one of these walls upon reflecting the process fluid leaving channels of one set and entering channels of the other. The body may be made of alternatingly corrugated and plane sheets using in turn two different orientations for the corrugated sheets. It is preferred that the sheets are arranged orthogonal to the heat transmitting wall(s) and parallel to the overall direction of flow. The method is preferred for endothermic processes, especially steam reforming of hydrocarbon(s).Type: GrantFiled: August 26, 1988Date of Patent: January 15, 1991Assignee: Haldor Topsoe A/SInventors: Niels T. Baden, Ernst J. Jensen, Jorgen G. Larsen
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Patent number: 4965379Abstract: A process for epoxidation of a fluoro-olefin is disclosed. The process comprises epoxidizing a fluoro-olefin represented by the general formula (I): ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3 each represents a substituent selected from (a) --F, (b) a perfluoroalkyl group having 2 to 20 carbon atoms and (c) --CF.sub.2 Y.sup.1, Y.sup.1 may be the same or different and represents a substituent selected from (d) a halogen atom selected from F, Cl, Br and I, (e) --OZ.sup.1 and (f) --Z.sup.1, wherein Z.sup.1 may be the same or different and represents a substituted or unsubstituted hydrocarbon group having not more than 20 carbon atoms, and X.sup.1, X.sup.2, X.sup.3 and Y.sup.1 may be combined with one another to form a cyclic compound, provided that all of X.sup.1, X.sup.2, X.sup.3 and Y.sup.1 do not represent --F; using a hypochlorite dissolved or suspended in an aqueous phase as an oxidizing agent in the presence or absence of an inorganic base.Type: GrantFiled: July 6, 1987Date of Patent: October 23, 1990Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Masanori Ikeda, Morikazu Miura, Atsushi Aoshima
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Patent number: 4892941Abstract: Disclosed are tetraphenyl porphyrins which are beta-substituted by fluoro or chloro and/or bear electronegative substituents on the phenyl including one or two water solubilizing substituents. The new porphorins are particularly suitable as catalysts in a variety of oxidative reactions and methods.Type: GrantFiled: April 15, 1988Date of Patent: January 9, 1990Inventors: David H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
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Patent number: 4864041Abstract: A novel process for the homogenous oxidation of organic substrates is disclosed. This process uses a transition metal-substituted polyoxometalate catalyst, which in the presence of an oxygen donor, catalyses the carbon-hydrogen bond (e.g., alkane) hydroxylation reaction and/or epoxidation reaction of the organic substrate.Type: GrantFiled: February 4, 1987Date of Patent: September 5, 1989Assignee: Emory UniversityInventor: Craig L. Hill
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Patent number: 4845253Abstract: A process of oxidizing an olefin having at least three carbon atoms directly to the corresponding epoxide comprising contacting the olefin with oxygen in the presence of a catalyst comprising a mixed silver-promoter metal (+2 or +3) silicate. In the direct oxidation of propylene the process yields a high selectivity to propylene oxide.Type: GrantFiled: November 23, 1987Date of Patent: July 4, 1989Assignee: The Dow Chemical CompanyInventor: Robert G. Bowman
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Patent number: 4841017Abstract: Disclosed as a polyether compound having ether groups and vinyl double bonds represented by formula (I) ##STR1## and an epoxy resin represented by formula (II) ##STR2## wherein R.sup.1 represents a residue group of an organic compound having l active hydrogen atoms, n1 through nl each represents 0 or an integer of from 1 to 100, the sum of integers represented by n1 through nl is from 1 to 100, and l represents an integer of from 1 to 100, and A represents from 1 to 100, and A represents ##STR3## or a mixture of ##STR4## wherein R.sup.2 represents a residue group of mono epoxy compound, and B represents ##STR5## or a mixture of ##STR6## wherein X represents a ##STR7## group, wherein R.sup.3 represents a hydrogen atom, an alkyl group, an alkyl carbonyl group, or an arylcarbonyl group, provided that the epoxy resin represented by formula (II) contains at least one ##STR8## group: In a further aspect, the invention relates to processes for production thereof.Type: GrantFiled: March 11, 1988Date of Patent: June 20, 1989Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Murai, Katsuhisa Sakai