Heavy Metal Containing Catalyst Utilized Patents (Class 549/533)
  • 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: 6124505
    Abstract: The invention provides a catalyst for partial oxidation of hydrocarbon in the presence of a reducing compound, the catalyst comprising ultra-fine gold particles immobilized on a titanium-containing oxide, and a process for preparing an oxygen-containing organic compound, the process comprising the step of oxidizing hydrocarbon with oxygen in the presence of the above catalyst and a reducing compound.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: September 26, 2000
    Assignees: Agency of Industrial Science and Technology, Nippon Shokubai Co., Ltd.
    Inventors: Masatake Haruta, Yuri Angelov Kalvachev, Susumu Tsubota, Toshio Hayashi, Masahiro Wada
  • Patent number: 6063943
    Abstract: The present invention relates to a heterogeneous polyimide-supported transition metal complex catalyst for epoxidation of olefin, which is prepared by impregnating a heat- and acid-resistant polyimide resin with a homogeneous metal catalyst of molybdenum, vanadium, tungsten or titanium, and a process for preparing epoxy compounds using the same. The heterogeneous polyimide-supported transition metal complex catalyst of the invention provides superior catalytic activity, selectivity and stability in the epoxidation of higher olefin. Further, the catalyst of the invention has strong resistance against heat and acid. Besides, the catalyst of the invention may provide the following advantages which are critical in industrial use: it permits relatively high yield of epoxy compounds; and, it can be easily separated from the reaction product, which eases recycling of the catalyst.
    Type: Grant
    Filed: December 11, 1998
    Date of Patent: May 16, 2000
    Assignee: Korea Advanced Institute of Science and Technology
    Inventors: Son Ki Ihm, Chang Gun Oh, Jou Hyeon Ahn, Jong Chan Kim, David C. Sherrington
  • Patent number: 6031116
    Abstract: A process and catalyst for the direct oxidation of an olefin having three or more carbon atoms, such as propylene, by oxygen to the corresponding olefin oxide, such as propylene oxide. The process involves contacting the olefin with oxygen under reaction conditions in the presence of hydrogen and in the presence of a catalyst. The catalyst comprises gold on a titanosilicate, preferably a microporous or mesoporous titanosilicate, such as, TS-1, TS-2, Ti-beta, Ti-ZSM-48, or Ti-MCM-41. Selectivity to the olefin oxide is high at good conversions of the olefin. The catalyst is readily regenerated, and the time between catalyst regenerations is long.
    Type: Grant
    Filed: December 11, 1998
    Date of Patent: February 29, 2000
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, Joseph L. Womack, Howard W. Clark, Joseph J. Maj, George E. Hartwell
  • Patent number: 6008389
    Abstract: An oxidation catalyst based on titanium silicalites or vanadium silicalites having a zeolite structure and containing from 0.01 to 30% by weight of one or more noble metals selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium, platinum, rhenium, gold and silver has been molded by a compacting shaping process.This oxidation catalyst is used for the preparation of epoxides, in particular propylene oxide, from olefins, hydrogen and oxygen.
    Type: Grant
    Filed: December 14, 1998
    Date of Patent: December 28, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Georg Heinrich Grosch, Ulrich Muller, Michael Schulz, Norbert Rieber, Harald Wurz
  • Patent number: 6002026
    Abstract: The present invention relates to novel oxidative processes for substrates such as olefins, alkanes, aromatics and alcohols using metallic porphyrin or salen catalytic complexes which have been specifically designed to maximize catalytic activity, thereby enhancing efficiency, selectively and speed of oxidation of these substrates. The choice of the substituents in the metallic complexes may be varied, but must be chosen to prevent specific ligand set arrangements known to be stable and therefore less catalytically efficient. Coordination complexes, particularly porphyrins and salens having nitrosyl axial ligands and electron-withdrawing peripheral substituents are preferred. Ruthenium coordination metals are the preferred metal center, with the highly reactive catalytic species found to be Ru.sup.III.
    Type: Grant
    Filed: December 5, 1996
    Date of Patent: December 14, 1999
    Assignee: The Trustees of Princeton University
    Inventors: John T. Groves, Tommaso Carofiglio, Marcella Bonchio, Anthony Sauve
  • Patent number: 5973171
    Abstract: An integrated process is provided for the production of propylene oxide from propane wherein propane is dehydrogenated to propylene and hydrogen and the resulting propylene, propane, and hydrogen mixture together with added oxygen is reacted over a palladium on titanium silicilite catalyst to form propylene oxide, the molar ratio of oxygen to hydrogen in the reaction feed being at least about 2/1.
    Type: Grant
    Filed: October 7, 1998
    Date of Patent: October 26, 1999
    Assignee: ARCO Chemical Technology, LP
    Inventors: Robert N. Cochran, John C. Jubin, Jr., Mark A. Liepa, Robert Nedwick, Rangasamy Pitchai, W. Wayne Wentzheimer
  • Patent number: 5965754
    Abstract: A process and catalyst for the direct oxidation of an olefin having three or more carbon atoms, such as propylene, by oxygen to an olefin oxide, such as propylene oxide. The process involves contacting the olefin with oxygen under reaction conditions in the presence of hydrogen and a catalyst. The catalyst comprises gold on a support of titanium dispersed on silica. The titanium phase is disorganized and substantially free of crystalline titanium dioxide, as determined by analytical methods, such as, high resolution transmission electron microscopy and Raman spectroscopy. Selectivity to olefin oxide is high at good conversions of the olefin. The time between catalyst regenerations is long, and the catalyst is readily regenerated.
    Type: Grant
    Filed: December 11, 1998
    Date of Patent: October 12, 1999
    Assignee: The Dow Chemical Company
    Inventors: Howard W. Clark, Robert G. Bowman, Joseph J. Maj, Simon R. Bare, George E. Hartwell
  • Patent number: 5859265
    Abstract: In an oxidation catalyst based on a titanium or vanadium silicalite having a zeolite structure and containing from 0.01 to 20% by weight of one or more platinum metals selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum, the platinum metals are each present in at least two different bond energy states and preferably have no metal-metal bonds.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: January 12, 1999
    Assignee: Basf Aktiengesellschaft
    Inventors: Ulrich Muller, Peter Lingelbach, Peter Bassler, Wolfgang Harder, Karsten Eller, Veronika Kohl, Jurgen Dembowski, Norbert Rieber, Martin Fischer
  • Patent number: 5856533
    Abstract: Heterogeneous vapor phase oxidation and other reactions are carried out at the surface of a solid catalyst, with both gaseous reactants and the solid catalyst being dispersed in a recirculating liquid solvent. Reaction and product absorption are combined into a single processing step, with enhanced catalyst performance, and product selectivity and product yields, enhanced mass and heat transfer characteristics and reduced risk of forming explosive mixtures in the course of a particular reaction.
    Type: Grant
    Filed: December 28, 1995
    Date of Patent: January 5, 1999
    Assignee: Praxair Technology, Inc.
    Inventors: Joshua Brien Sweeney, Roger William Day, Deepak Lumba
  • 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: 5756779
    Abstract: Disclosed are improved processes for the recovery of 3,4-epoxy-1-butene (epoxybutene) from an epoxidation effluent comprising epoxybutane, butadiene, oxygen and an inert diluent obtained by the selective epoxidation of butadiene with an oxygen-containing gas in the presence of a catalyst and an inert gas. Epoxybutene is separated from the effluent by means of an absorption process using an extractant comprising liquid butadiene and, optionally, a hydrocarbon diluent. The formation of butenediols, by the reaction of epoxybutene and water, in the recovery process is inhibited by the addition of a base, preferably an alkali metal base, to the recovery system.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: May 26, 1998
    Assignee: Eastman Chemical Company
    Inventor: Jerome Leonard Stavinoha, Jr.
  • Patent number: 5744620
    Abstract: A catalyzed process whereby a cyclic olefin is oxidized to produce an epoxide is disclosed. The inventive process which uses air, or molecular oxygen as the sole oxidizing agent, and which is catalyzed by a specifically structured metallosalen complex is characterized in its high selectivity and high turnover efficiency.
    Type: Grant
    Filed: July 10, 1997
    Date of Patent: April 28, 1998
    Assignee: Bayer Corporation
    Inventors: Yu-Ling Hsiao, Harry B. Gray, Jay A. Labinger
  • Patent number: 5670674
    Abstract: Oxirane compounds are produced by molecular oxygen oxidation of an olefin in the presence of a platinum (II) dihalide catalyst.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: September 23, 1997
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Roger A. Grey
  • 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: 5623090
    Abstract: An alcohol or a ketone or a mixture thereof is produced from a saturated hydrocarbon or an epoxide is produced from an unsaturated hydrocarbon by passing a mixture comprising of molecular hydrogen, the saturated or unsaturated hydrocarbon and oxygen through a bed of a catalyst comprising a titanium dioxide carrier and ultrafine gold particles deposited on the carrier, thereby effecting the oxidation of the hydrocarbon with oxygen.
    Type: Grant
    Filed: October 25, 1995
    Date of Patent: April 22, 1997
    Assignee: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Masatake Haruta, Susumu Tsubota, Toshio Hayashi
  • Patent number: 5620938
    Abstract: The invention relates to a catalyst for the epoxidation of alkenes using alkylhydroperoxide, the catalyst comprising an ion of one or more of the metals molybdenum, wolfram, titanium or vanadium on an inorganic carrier, characterised in that the metal ion is bound to the carrier via a polydentate organic ligand.The invention also relates to a process for the preparation of an alkene oxide by an alkene having 3 or more carbon atoms with an alkylhydroperoxide, using the catalyst described above.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: April 15, 1997
    Assignee: DSM N.V.
    Inventor: Otto E. Sielcken
  • Patent number: 5616750
    Abstract: A compound of formula (I): ##STR1## n which M is a transition metal ion; A is a counter-ion if required;r, s and t are independently 0 to 3 such that r+s+t is in the range of 1 to 3;R.sup.a, R.sup.b, R.sup.c are each independently hydrogen or CH.sub.2 OR' where R' is hydrogen or an organic group;B and E are independently oxygen, CH.sub.2, NR.sup.d in which R.sup.d is alkyl, hydrogen, alkylcarbonyl, or arylcarbonyl or SO.sub.n where n is 0 or an integer 1 or 2, with the proviso that B and E are not simultaneously CH.sub.2 and that when B is oxygen, NR.sup.d or SO.sub.n, then r cannot be 0, and when E is oxygen, NR.sup.d or SO.sub.n, then t cannot be 0;R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are independently hydrogen, alkyl or alkoxy.
    Type: Grant
    Filed: October 6, 1993
    Date of Patent: April 1, 1997
    Assignee: SmithKline Beecham plc
    Inventors: David Bell, David Miller, Robin P. Attrill
  • Patent number: 5599957
    Abstract: An optically active manganese complex of the formula I.sub.a, I.sub.b, I.sub.c and I.sub.d ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen atom, C.sub.1 -.sub.4 alkyl group, phenyl group which may be substituted by a halogen atom, C.sub.1 -.sub.4 alkyl group, C.sub.1 -.sub.4 alkoxyl group, cyano group or nitro group; and any two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 together form a C.sub.4 -.sub.8 ring, X.sup.- represents a counter anion which may form a salt, Y represents hydrogen atom, halogen atom, C.sub.1 -.sub.4 alkyl group, C.sub.1 -.sub.4 alkoxyl group, nitro group or cyano group, R represents hydrogen atom, C.sub.1 -.sub.4 alkyl group, phenyl group which may be substituted by halogen atom, C.sub.1 -.sub.4 alkyl group or C.sub.1 -.sub.4 alkoxyl group, or substituted silyl group and a process for producing epoxy compounds using the complex as a catalyst.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: February 4, 1997
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tsutomu Katsuki, Ryo Irie, Hidehiko Sasaki
  • Patent number: 5466837
    Abstract: An ethylene stream which contains ethane as an impurity or a propylene stream which contains propane as an impurity is subjected to adsorption at a temperature of 50.degree. to 200.degree. C. in a bed of adsorbent which selectively adsorbs ethylene or propylene, thereby adsorbing substantially all of the ethylene or propylene. The purified ethylene or propylene stream is then subjected to partial oxidation in the presence of oxygen and, optionally ammonia to produce various partial oxidation products. The process is operated on a low per pass conversion with recycle of unreacted ethylene or propylene. In the system of the invention the adsorption unit may be upstream or downstream of the partial oxidation reactor.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: November 14, 1995
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Loc H. Dao
  • Patent number: 5466838
    Abstract: A process for producing an epoxide represented by the formula (2) which comprises reacting an olefin represented by the formula (1) with oxygen in the presence of an aldehyde and in the presence or absence of a proton source by using no catalyst or using an iron-containing or copper-containing catalyst.
    Type: Grant
    Filed: July 19, 1994
    Date of Patent: November 14, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
  • Patent number: 5420314
    Abstract: An optically active manganese complex of the formula I or I': ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 independently represent hydrogen atom, C.sub.1 -C.sub.4 alkyl group, phenyl group which may be substituted by a halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxyl group, cyano group or nitro group; and any two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 together form the C.sub.4 -C.sub.8 ring, X.sup.- represents a counter anion which may form a salt, Y represents hydrogen atom, halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxyl group, nitro group or cyano group, R represents hydrogen atom, C.sub.1 -C.sub.4 alkyl group, phenyl group which may be substituted by halogen atom, C.sub.1 -C.sub.4 alkyl group or C.sub.1 -C.sub.4 alkoxyl group, or substituted silyl group and a process for producing epoxy compounds using the complex as a catalyst.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: May 30, 1995
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tsutomu Katsuki, Ryo Irie, Hidehiko Sasaki
  • Patent number: 5367087
    Abstract: A process for producing an epoxide represented by the formula (2) which comprises reacting an olefin represented by the formula (1) with oxygen in the presence of an aldehyde and in the presence or absence of a proton source by using no catalyst or using an iron-containing or copper-containing catalyst.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: November 22, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
  • 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: 5221795
    Abstract: Process for producing olefin oxides by means of the reaction of an olefin with oxygen or air, in the presence of a catalyst constituted by titanium silicalite and a redox system comprising alkyl-anthrahydroquinone and alkyl-anthraquinone, with said reaction being carried out in a solvent mixture consisting of:(a) one or more aromatic or alkyl-aromatic, mono- or polynuclear hydrocarbon(s) selected from among benzene, toluene, xylene, alpha-methyl-naphthalene or halogenated derivatives thereof, such as dichlorobenzene;(b) one or more polar organic compound(s) with boiling point comprised within the range of from 150.degree. to 350.degree. C., and selected from among di-isobutylcarbinol, di-isobutyl-ketone, methyl-cyclohexyl acetate, dimethyl phthalate, dibutyl phthalate, diethylhexyl phthalate and tert-butyl phthalate;(c) a low molecular weight alcohol, preferably methanol.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: June 22, 1993
    Assignee: Eniricerche S.p.A.
    Inventors: Marjo G. Clerici, Patrizia Ingallina
  • Patent number: 5068366
    Abstract: A process for the preparation of isobutylene oxide and isobutyric acid from isobutylene and isobutyraldehyde, respectively, by a co-oxidation process conducted in the presence of oxygen and a cobalt salt catalyst at a temperature of about 20.degree. to about 180.degree. C. is disclosed.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: November 26, 1991
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 4992567
    Abstract: A continuous process for the vapor phase oxidation of an alkane or olefin in molten salt catalyst to produce alkylene oxides in increased yields while reducing or substantially eliminating the formation of aldehyde by-products. The process involves the continuous separation and recirculation of aldehydes, normally formed in the oxidation reaction, back into the vapor phase oxidation reaction for co-oxidation to form carbon-oxygen gases while increasing the olefin selectivity to alkylene oxide.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: February 12, 1991
    Assignee: Olin Corporation
    Inventors: James L. Meyer, Pennington, B. Timothy
  • Patent number: 4959486
    Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an alkane or alkylaromatic compound mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt catalyst.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: September 25, 1990
    Assignee: Olin Corporation
    Inventor: B. Timothy Pennington
  • Patent number: 4943643
    Abstract: A process for the vapor phase oxidation of olefins in molten salt catalyst to produce alkylene oxides in increased molar selectivity and per-pass yields while reducing the molar selectivity of aldehyde by-products. The process involves the use of molten nitrate salt catalyst compositions which comprise lithium nitrate and which are heated and operated at a low temperature within the range of about 180.degree. C. up to about 250.degree. C., more preferably 200.degree. C. to 250.degree. C.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: July 24, 1990
    Assignee: Olin Corporation
    Inventors: B. Timothy Pennington, Michael C. Fullington
  • Patent number: 4943644
    Abstract: A method of oxidizing olefins or alkanes by contacting with oxygen and a catalyst composition of the formula:Ru.sub.3 O[OCO(CF.sub.2).sub.y CF.sub.3 ].sub.6 LWherein: Ru are reuthenium atoms having a formal oxidation state of +2 or +3,L is a neutral or anionic ligand,Y is an integer from 0 to 6, andx is an integer from 1 to 3; and an anion.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: July 24, 1990
    Assignee: The University of Florida
    Inventors: Russell S. Drago, Shannon Davis
  • Patent number: 4885374
    Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an alkane or alkylaromatic compound mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt catalyst.
    Type: Grant
    Filed: August 31, 1988
    Date of Patent: December 5, 1989
    Assignee: Olin Corporation
    Inventor: B. Timothy Pennington
  • Patent number: 4883889
    Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an olefin or mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt and a co-catalyst.
    Type: Grant
    Filed: April 18, 1988
    Date of Patent: November 28, 1989
    Assignee: Olin Corporation
    Inventor: B. Timothy Pennington
  • Patent number: 4882443
    Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting a C7 to C22 olefin or mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt.
    Type: Grant
    Filed: August 31, 1988
    Date of Patent: November 21, 1989
    Assignee: Olin Corporation
    Inventor: B. Timothy Pennington
  • 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: 4822899
    Abstract: Metallic porphyrin complexes are useful as catalysts for the epoxidation of olefins at ambient temperature and pressure using oxygen, which preferably is supplied either as air or pure oxygen, without need for a coreductant.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: April 18, 1989
    Assignee: The University of Michigan
    Inventors: John T. Groves, Robert Quinn
  • Patent number: 4785123
    Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an alkane, an alkylene, or mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: November 15, 1988
    Assignee: Olin Corporation
    Inventor: B. Timothy Pennington
  • Patent number: 4721798
    Abstract: The invention provides a process for epoxidizing an olefinic double bond in an olefinically-unsaturated compound by contact of a liquid phase mixture containing the olefinically-unsaturated compound, an aldehyde having at least two carbon atoms and a suitable solvent with molecular oxygen in the presence of a catalyst which is soluble in the reaction mixture and which comprises a praseodymium compound. The process has particularly advantageous application to oxidation of aldrin to dieldrin.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: January 26, 1988
    Assignee: Shell Oil Company
    Inventor: Albertus J. Mulder
  • Patent number: 4687868
    Abstract: Production of novel molybdenum dioxo dialkyleneglycolate compositions, especially adapted for use as catalysts in the epoxidation of olefinic compounds with an organic hydroperoxide, by reaction of molybdenum trioxide with particular dialkylene glycol compounds at specified elevated temperatures while removing water.
    Type: Grant
    Filed: April 23, 1986
    Date of Patent: August 18, 1987
    Assignee: Atlantic Richfield Company
    Inventors: Wilfred P. Shum, Charles F. Cooper
  • Patent number: 4607113
    Abstract: Production of novel molybdenum dioxo dialkyleneglycolate compositions, especially adapted for use as catalysts in the epoxidation of olefinic compounds with an organic hydroperoxide, by reaction of molybdenum trioxide with particular dialkylene glycol compounds at specified elevated temperatures while removing water.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: August 19, 1986
    Assignee: Atlantic Richfield Company
    Inventors: Wilfred P. Shum, Charles F. Cooper
  • Patent number: 4521609
    Abstract: A process for the production of cycloalkane epoxides from cycloalkenes in the presence of a tungsten or zirconium containing catalyst, oxygen and a carboxylate ion source via air oxidation is described. For example, cobalt tungstate, nickel tungstate, silver tungstate and manganese tungstate are useful catalysts. Active zirconates are cerium zirconate, cadmium zirconate and lead zirconate. The reaction is conducted at a temperature in the range of 50.degree. to 150.degree. C. and a pressure of one atmosphere or greater. Cycloalkane epoxides are useful in the preparation of resins, plasticizers, etc.
    Type: Grant
    Filed: July 1, 1983
    Date of Patent: June 4, 1985
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr., Steven H. Vanderpool, Terry L. Renken
  • Patent number: 4517374
    Abstract: A process for the production of cycloalkane epoxides from cycloalkenes in the presence of an oxide catalyst, oxygen and a carboxylate ion source via air oxidation is described. The oxide catalyst may have as a cation boron, chromium, iron, nickel, copper, zinc or terbium or mixtures thereof. Combination catalysts such as ferric oxide/zinc oxide and nickel oxide/copper oxide/chromium oxide/boric oxide complexes are also found to be useful. The reaction is conducted at a temperature in the range of 50.degree. to 150.degree. C. and a pressure of one atmosphere or greater. Cycloalkane epoxides are useful in the preparation of resins, plasticizers, etc.
    Type: Grant
    Filed: July 1, 1983
    Date of Patent: May 14, 1985
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr., Terry L. Renken
  • Patent number: 4483998
    Abstract: A process for simultaneously producing an epoxide and a carboxylic acid from an olefin and an aldehyde, respectively, by co-oxidation over a catalyst in the presence of oxygen is described. The catalyst is made by precipitating silver oxide in the presence of copper(II) oxide, copper(II) borate or a mixture thereof. These novel heterogeneous catalysts provide higher selectivities to the epoxide than those obtainable with commercial catalysts.
    Type: Grant
    Filed: April 11, 1983
    Date of Patent: November 20, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Edward T. Marquis, Jiang-Jen Lin
  • Patent number: 4474974
    Abstract: A process for the direct oxidation of propylene in the presence of oxygen, a silver catalyst and chlorobenzene as a solvent is described. Halocarbon co-solvents such as trichlorotrifluoroethane are used to enhance selectivity to the desired propylene oxide. The direct oxidation is preferably run at a temperature between about 150.degree. to 250.degree. C.
    Type: Grant
    Filed: April 21, 1983
    Date of Patent: October 2, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Stanley B. Cavitt, Edward T. Marquis
  • Patent number: 4469880
    Abstract: A process for the production of cycloalkane epoxides from cycloalkenes in the presence of a boron-containing catalyst, oxygen and a carboxylate ion source via air oxidation is described. Alkali metal borates, alkali earth metal borates, rare earth borates and transition metal borates are useful catalysts. The boron catalyst may contain many different cations including lithium, sodium, strontium, barium, cerium, zirconium, vanadium, niobium, iron, cobalt, nickel, copper, zinc, and mixtures thereof. The reaction is conducted at a temperature in the range of 50.degree. to 150.degree. C. and a pressure of one atmosphere or greater. Cycloalkane epoxides are useful in the preparation of resins, plasticizers, etc.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: September 4, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr., Terry L. Renken, Steven H. Vanderpool
  • Patent number: 4420625
    Abstract: A process for the production of alkylene oxides from olefins in the presence of transition metal borate catalysts, oxygen and a non-polar, aromatic organic solvent via one-step, direct oxidation is described. The reaction is conducted at a temperature in the range of 80.degree. to 280.degree. C. and a pressure of 1 atmosphere or greater. Alkylene oxides have a variety of uses such as in polyols for urethane foams, the production of alkylene glycols, surfactants and detergents, alkanolamines, fumigants, synthetic lubricants and elastomers.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: December 13, 1983
    Assignee: Texaco, Inc.
    Inventors: John R. Sanderson, Walter H. Brader, Jr., Lewis W. Watts, Jr.
  • Patent number: 4391756
    Abstract: The present invention relates to the oxidation of monoolefins with molecular oxygen to the corresponding olefin oxides, in the liquid phase in the presence of a catalyst comprising an organo-monovalent aurous complex.
    Type: Grant
    Filed: December 13, 1978
    Date of Patent: July 5, 1983
    Assignee: The Standard Oil Company
    Inventors: Philip L. Kuch, Daniel R. Herrington, Janet M. Eggett
  • Patent number: 4390738
    Abstract: Olefine oxides or derivatives thereof such as glycols are produced by reacting an olefinic compound e.g. ethylene, propylene or butadiene with oxygen in the presence of a catalyst containing copper bonded to a peroxo group.
    Type: Grant
    Filed: June 18, 1981
    Date of Patent: June 28, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventors: Dhafir Y. Waddan, Derek Williams
  • Patent number: 4345984
    Abstract: A novel process for the oxidation of olefins to the corresponding alpha-epoxy alcohols which can be incorporated in the total synthesis of members of a novel class of prostaglandin analogues.Olefins are reacted with singlet oxygen in the presence of a group IVB, VB or VIB transition metal catalyst, excluding chromium. The reaction is fast and highly selective to the alpha-epoxy alcohol. When cyclopentene is oxidized in the process of the invention, high yields of cis 2,3-epoxy-cyclopentan-1-ol are obtained. The latter compound is used as a starting material in the synthesis of prostaglandin analogues. The prostanoids of the invention are characterized by an oxa group replacing the methylene group at the 7-position, and the absence of a hydroxyl or other substituent at the 11-position.Members of this class of prostanoids show important cytoprotective properties in animal tests.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: August 24, 1982
    Assignee: The Procter & Gamble Company
    Inventor: Edward D. Mihelich