Liquid Phase Epoxidation Patents (Class 549/524)
  • Patent number: 6770766
    Abstract: 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: Grant
    Filed: July 24, 2002
    Date of Patent: August 3, 2004
    Assignee: Bayer Chemicals AG
    Inventors: Thomas Geller, Christa Maria Krüger, Hans-Christian Militzer
  • Publication number: 20040138481
    Abstract: 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: Application
    Filed: January 10, 2003
    Publication date: July 15, 2004
    Inventors: Thomas K. Highsmith, Harold E. Johnston
  • Patent number: 6743748
    Abstract: 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: Grant
    Filed: March 7, 2003
    Date of Patent: June 1, 2004
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Noritaka Mizuno, Yasutaka Sumida, Koji Yonehara, Masahiro Wada, Minoru Urata
  • Patent number: 6700004
    Abstract: 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: Grant
    Filed: July 24, 2002
    Date of Patent: March 2, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Geller, Christa Maria Krüger, Hans-Christian Militzer
  • Patent number: 6686483
    Abstract: 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: Grant
    Filed: January 7, 2002
    Date of Patent: February 3, 2004
    Assignee: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Patent number: 6653419
    Abstract: 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: Grant
    Filed: October 3, 2001
    Date of Patent: November 25, 2003
    Assignee: E. .I du Pont de Nemours and Company
    Inventors: Viacheslav Alexandrovich Petrov, Andrew Edward Fiering, Jerald Feldman
  • Patent number: 6608219
    Abstract: 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: Grant
    Filed: June 13, 2002
    Date of Patent: August 19, 2003
    Assignees: Degussa AG, Uhde GmbH
    Inventors: Thomas Haas, Willi Hofen, Georg Thiele, Stefan Pilz, Wolfgang Woell
  • Patent number: 6605733
    Abstract: 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: Grant
    Filed: December 28, 2001
    Date of Patent: August 12, 2003
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Hideki Omori, Hiroko Ahara, Kazuhiko Haba, Yoshiaki Takaya, Shin Irie
  • Publication number: 20030087401
    Abstract: 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: Application
    Filed: July 24, 2002
    Publication date: May 8, 2003
    Inventors: Thomas Geller, Christa Maria Kruger, Hans-Christian Militzer
  • Patent number: 6559283
    Abstract: Poly-&bgr;-amino acids and their use in catalytic organic reactions, especially in epoxidation procedures, are provided.
    Type: Grant
    Filed: June 14, 2001
    Date of Patent: May 6, 2003
    Assignee: Degussa AG
    Inventors: Karlheinz Drauz, Olaf Burkhardt, Stan M. Roberts, John Skidmore, Paul Coffey
  • Publication number: 20030064486
    Abstract: 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: Application
    Filed: July 24, 2002
    Publication date: April 3, 2003
    Inventors: Thomas Geller, Christa Maria Kruger, Hans-Christian Militzer
  • Patent number: 6534661
    Abstract: 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: Grant
    Filed: November 30, 2001
    Date of Patent: March 18, 2003
    Assignee: Hydrocarbon Technologies, Inc.
    Inventors: Bing Zhou, Michael Rueter
  • Patent number: 6525208
    Abstract: 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: Grant
    Filed: April 3, 2002
    Date of Patent: February 25, 2003
    Assignee: Albemarle Corporation
    Inventors: Chi Hung Cheng, Gerald M. Sulzer
  • Publication number: 20020133031
    Abstract: 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: Application
    Filed: January 7, 2002
    Publication date: September 19, 2002
    Applicant: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Patent number: 6429322
    Abstract: 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: Grant
    Filed: September 22, 2000
    Date of Patent: August 6, 2002
    Assignee: Solvay SA
    Inventors: Jean-Pierre Catinat, Michel Strebelle
  • Patent number: 6423853
    Abstract: 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: Grant
    Filed: September 24, 2001
    Date of Patent: July 23, 2002
    Assignee: E. I. du Pont de Nemours & Comp.
    Inventors: Edward F. Moran, Jr., Chester Arthur Thayer, II
  • Patent number: 6414168
    Abstract: 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: Grant
    Filed: December 28, 1999
    Date of Patent: July 2, 2002
    Assignee: CasChem, Inc.
    Inventors: James V. Crivello, Srinivasan Chakrapani
  • Patent number: 6403815
    Abstract: 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: Grant
    Filed: November 29, 2001
    Date of Patent: June 11, 2002
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Roger A. Grey
  • Patent number: 6348608
    Abstract: A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.
    Type: Grant
    Filed: April 6, 1999
    Date of Patent: February 19, 2002
    Inventor: Yian Shi
  • Patent number: 6307073
    Abstract: 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: Grant
    Filed: July 25, 2000
    Date of Patent: October 23, 2001
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: C. Andrew Jones
  • Patent number: 6288248
    Abstract: 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: Grant
    Filed: November 25, 1998
    Date of Patent: September 11, 2001
    Assignee: Solvay (Société Anonyme)
    Inventors: Michel Strebelle, Patrick Gilbeau, Jean-Pierre Catinat
  • Patent number: 6225482
    Abstract: 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: Grant
    Filed: November 30, 1999
    Date of Patent: May 1, 2001
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Karlheinz Drauz, Stan M. Roberts, John Skidmore
  • Patent number: 6160137
    Abstract: 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: Grant
    Filed: November 5, 1998
    Date of Patent: December 12, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junpei Tsuji, Masaru Ishino, Kenshi Uchida
  • Patent number: 6087513
    Abstract: 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: Grant
    Filed: May 21, 1999
    Date of Patent: July 11, 2000
    Assignee: The Dow Chemical Company
    Inventors: Zeng K. Liao, Clinton J. Boriack
  • Patent number: 6087514
    Abstract: 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: Grant
    Filed: October 20, 1998
    Date of Patent: July 11, 2000
    Assignee: Engelhard Corporation
    Inventors: Appadurai Thangaraj, Steven M. Kuznicki, Gerald S. Koermer
  • Patent number: 6087299
    Abstract: 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: Grant
    Filed: January 26, 1999
    Date of Patent: July 11, 2000
    Assignee: EC Erdolchemie GmbH
    Inventors: Joachim Grub, Werner Volprecht, Matthias Baum, Alfred Reimer
  • Patent number: 6066750
    Abstract: 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: Grant
    Filed: December 30, 1998
    Date of Patent: May 23, 2000
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Te Chang
  • Patent number: 6063944
    Abstract: 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: Grant
    Filed: May 4, 1998
    Date of Patent: May 16, 2000
    Assignee: Elf Aquitaine
    Inventors: Francesco Di Renzo, Sylvie Gomez, Francois Fajula, Remy Teissier
  • Patent number: 6051725
    Abstract: 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: Grant
    Filed: December 28, 1998
    Date of Patent: April 18, 2000
    Assignee: Caschem, Inc.
    Inventors: James V. Crivello, Srinivasan Chakrapani
  • Patent number: 6008386
    Abstract: 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: Grant
    Filed: July 22, 1997
    Date of Patent: December 28, 1999
    Assignee: Board of Regents University of Nebraska-Lincoln
    Inventors: David B. Berkowitz, Michelle L. Pedersen
  • Patent number: 5916430
    Abstract: 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: Grant
    Filed: September 7, 1993
    Date of Patent: June 29, 1999
    Assignee: BASF Aktiengesellschaft
    Inventor: Dieter Haermeling
  • Patent number: 5792878
    Abstract: 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: Grant
    Filed: June 28, 1996
    Date of Patent: August 11, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Matthias Beller, Ahmed Tafesh, Richard Walter Fischer, Bernd Scharbert
  • Patent number: 5705660
    Abstract: 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: Grant
    Filed: August 22, 1994
    Date of Patent: January 6, 1998
    Assignee: Board of Regents, University of Nebraska-Lincoln
    Inventors: David B. Berkowitz, Michelle L. Pedersen
  • Patent number: 5663393
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: September 2, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
  • Patent number: 5637739
    Abstract: 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: Grant
    Filed: October 15, 1992
    Date of Patent: June 10, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Eric N. Jacobsen, Wei Zhang, Li Deng
  • Patent number: 5621118
    Abstract: 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: Grant
    Filed: April 14, 1994
    Date of Patent: April 15, 1997
    Assignee: Solvay Interox Limited
    Inventors: Craig W. Jones, William R. Sanderson, John P. Sankey
  • Patent number: 5578744
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: November 26, 1996
    Assignees: Eniricerche S.p.A., Snamprogetti S.p.A.
    Inventors: Angela Carati, Enrico Davini, Mario G. Clerici, Giuseppe Bellussi
  • Patent number: 5428180
    Abstract: 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: Grant
    Filed: December 10, 1993
    Date of Patent: June 27, 1995
    Assignee: The Research Foundation of State University of New York
    Inventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
  • Patent number: 5329024
    Abstract: 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: Grant
    Filed: March 30, 1993
    Date of Patent: July 12, 1994
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Sharon H. Jureller, Judith L. Kerschner, Robert Humphreys
  • Patent number: 5268489
    Abstract: 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: Grant
    Filed: February 5, 1993
    Date of Patent: December 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
  • Patent number: 5227501
    Abstract: 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: Grant
    Filed: May 12, 1992
    Date of Patent: July 13, 1993
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shinichi Sato, Yasuo Tarumi, Takashi Matsuda, Hiromasa Yamaguchi
  • Patent number: 5126464
    Abstract: 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: Grant
    Filed: October 29, 1990
    Date of Patent: June 30, 1992
    Assignee: The Research Foundation of State University of New York
    Inventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
  • Patent number: 5084583
    Abstract: The synthesis of epoxides from fluorine containing olefins using elemental fluorine in mixtures of water and acetonitrile is disclosed.
    Type: Grant
    Filed: January 9, 1991
    Date of Patent: January 28, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Shlomo M. Rozen, Bruce E. Smart
  • Patent number: 5077394
    Abstract: 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: Grant
    Filed: December 21, 1989
    Date of Patent: December 31, 1991
    Assignee: Sandoz Ltd.
    Inventors: David H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
  • Patent number: 4985230
    Abstract: 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: Grant
    Filed: August 26, 1988
    Date of Patent: January 15, 1991
    Assignee: Haldor Topsoe A/S
    Inventors: Niels T. Baden, Ernst J. Jensen, Jorgen G. Larsen
  • Patent number: 4965379
    Abstract: 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: Grant
    Filed: July 6, 1987
    Date of Patent: October 23, 1990
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Masanori Ikeda, Morikazu Miura, Atsushi Aoshima
  • Patent number: 4892941
    Abstract: 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: Grant
    Filed: April 15, 1988
    Date of Patent: January 9, 1990
    Inventors: David H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
  • Patent number: 4864041
    Abstract: 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: Grant
    Filed: February 4, 1987
    Date of Patent: September 5, 1989
    Assignee: Emory University
    Inventor: Craig L. Hill
  • Patent number: 4845253
    Abstract: 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: Grant
    Filed: November 23, 1987
    Date of Patent: July 4, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert G. Bowman
  • Patent number: 4841017
    Abstract: 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: Grant
    Filed: March 11, 1988
    Date of Patent: June 20, 1989
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Murai, Katsuhisa Sakai