Preparing By Hydroxylation At Point Of Ethylenic Unsaturation Patents (Class 568/860)
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Patent number: 10526300Abstract: Processes for reducing the amount of a gaseous iodide-containing impurity present in a recycle gas stream used in the production of ethylene oxide, in particular alkyl iodide and vinyl iodide impurities, are provided. Processes for producing ethylene oxide, ethylene carbonate and/or ethylene glycol, and associated reaction systems are similarly provided.Type: GrantFiled: December 13, 2016Date of Patent: January 7, 2020Assignee: SHELL OIL COMPANYInventors: Wayne Errol Evans, Jesse Raymond Black, Michael Francis Lemanski
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Publication number: 20150119542Abstract: An electrochemical conversion method for converting at least a portion of a first mixture comprising hydrocarbon to C2+ unsaturates by repeatedly applying an electric potential difference, V(?1), to a first electrode of an electrochemical cell during a first time interval ?1; and reducing the electric potential difference, V(?1), to a second electric potential difference, V(?2), for a second time interval ?2, wherein ?2??1. The method is beneficial, among other things, for reducing coke formation in the electrochemical production of C2+ unsaturates in an electrochemical cell. Accordingly, a method of reducing coke formation in the electrochemical conversion of such mixtures and a method for electrochemically converting carbon to C2+ unsaturates as well as an apparatus for such methods are also provided.Type: ApplicationFiled: October 17, 2014Publication date: April 30, 2015Inventors: Walter Weissman, Sumathy Raman, Mark A. Greaney
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Publication number: 20150087866Abstract: The present invention relates to the process of production of olefins by means of the dehydration of light alcohols using ionic liquids as an acidic medium. Furthermore, the present invention relates to the use of such olefins, for example, for the production of polymers and ethylene glycol.Type: ApplicationFiled: August 30, 2012Publication date: March 26, 2015Applicants: UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL-UFRGS, BRASKEM S.A.Inventor: Michèle Oberson De Souza
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Publication number: 20140296570Abstract: The invention relates to a process for converting hydrocarbons into products containing aldehydes and/or alcohols. The invention also relates to producing olefins from the aldehyde and alcohol, to polymerizing the olefins, and to equipment useful for these processes.Type: ApplicationFiled: December 20, 2011Publication date: October 2, 2014Applicant: Exxonmobile Chemical Patents Inc.Inventors: Paul F. Keusenkothen, Frank Hershkowitz
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Patent number: 8742180Abstract: Embodiments of the present disclosure include methods of effecting process control in a reaction system for the production of 1,4-butanediol, the method including determining at least one property of a sample from the reaction system using Raman spectroscopy, and adjusting at least one parameter of the reaction system in response to the at least one determined property. Embodiments may also include methods of producing 1,4-butanediol, the method including reacting allyl alcohol with carbon monoxide and hydrogen in the presence of a solvent and a catalyst to produce a reactor fluid, sampling the reaction, determining at least one property of the sample using Raman spectroscopy, and adjusting the reaction in response to the at least one determined property.Type: GrantFiled: November 13, 2012Date of Patent: June 3, 2014Assignee: Lyondell Chemical Technology, L.P.Inventors: Daniel F. White, Brian A. Salisbury, Jenny M. Oran Osment
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Publication number: 20140135537Abstract: Embodiments of the present disclosure include methods of effecting process control in a reaction system for the production of 1,4-butanediol, the method including determining at least one property of a sample from the reaction system using Raman spectroscopy, and adjusting at least one parameter of the reaction system in response to the at least one determined property. Embodiments may also include methods of producing 1,4-butanediol, the method including reacting allyl alcohol with carbon monoxide and hydrogen in the presence of a solvent and a catalyst to produce a reactor fluid, sampling the reaction, determining at least one property of the sample using Raman spectroscopy, and adjusting the reaction in response to the at least one determined property.Type: ApplicationFiled: November 13, 2012Publication date: May 15, 2014Applicant: Lyondell Chemical Technology, L.P.Inventors: Daniel F. White, Brian A. Salisbury, Jenny M. Oran Osment
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Publication number: 20140128620Abstract: The invention provides a process for the preparation of an alkylene glycol from an alkene. A gas composition from an alkylene oxide reactor is supplied to an alkylene oxide absorber comprising a column of vertically stacked trays or comprising a packed column. Lean absorbent comprising at least 20 wt % water is supplied to the alkylene oxide absorber and is contacted with the gas composition in the presence of one or more catalysts that promote carboxylation and hydrolysis. At least 50% of the alkylene oxide entering the alkylene oxide absorber is converted in the alkylene oxide absorber. Fat absorbent is withdrawn from the absorber, is optionally supplied to finishing reactors and/or a flash vessel or light ends stripper, and is subsequently subjected to dehydration and purification to provide a purified alkylene glycol product stream.Type: ApplicationFiled: January 13, 2014Publication date: May 8, 2014Applicant: SHELL OIL COMPANYInventors: Eugene Marie Godfried Andre VAN KRUCHTEN, Dominicus Maria REKERS, Mathias Jozef Paul SLAPAK
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Publication number: 20140058138Abstract: Methods and systems are provided for converting methane in a feed stream to butanediol. The method includes processing acetylene as an intermediate stream to form a hydrocarbon stream including butanediol. A hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of carbon monoxide to prevent undesired reactions in downstream processing units.Type: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
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Publication number: 20130317238Abstract: The present disclosure generally relates to processes, apparatuses and custom catalysts designed to depolymerize a polymer. In one embodiment, the present invention relates to a de-polymerizing apparatus, catalysts and reaction schemes to obtain useful monomers including fuel products by “in situ” reactions using coupled electromagnetic induction.Type: ApplicationFiled: December 8, 2011Publication date: November 28, 2013Inventors: Pravansu S. Mohanty, Swaminathan Ramesh
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Patent number: 8502000Abstract: Methods and systems for the hydroxylation of olefenic alcohols are described herein. The methods and systems incorporate the novel use of a high shear device to promote mixing and solubility of peroxides with the olefenic alcohol. The high shear device may allow for lower reaction temperatures and pressures and may also reduce hydroxylation time with existing catalysts.Type: GrantFiled: June 23, 2008Date of Patent: August 6, 2013Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8357825Abstract: A process for preparing a 1,2-diol, a 1,2-diol ether or an alkanolamine comprising converting an olefin oxide, wherein the olefin oxide has been obtained by a process for the epoxidation of an olefin, said process comprising using a catalyst comprising a carrier and silver deposited thereon, wherein the carrier comprises at least 85 weight percent ?-alumina and has a surface area of at least 1.3 m2/g, a median pore diameter of more than 0.8 ?m, and a pore size distribution wherein at least 80% of the total pore is contained in pores with diameters in the range of from 0.1 to 10 ?m, and at least 80% of the pore volume contained in the pores with diameters in the range of from 0.1 to 10 ?m is contained in pores with diameters in the range of from 0.3 to 10 ?m.Type: GrantFiled: November 18, 2011Date of Patent: January 22, 2013Assignee: Shell Oil CompanyInventors: William Herman Gerdes, John Robert Lockemeyer, Donald James Remus, Thomas Szymanski, Randall Clayton Yeates
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Patent number: 8357813Abstract: The invention provides a process for the epoxidation of an olefin, which process comprises reacting a feed comprising an olefin and oxygen in the presence of a catalyst comprising a carrier and silver deposited on the carrier, which carrier comprises at least 85 weight percent ?-alumina and has a surface area of at least 1.3 m2/g, a median pore diameter of more than 0.8 ?m, and a pore size distribution wherein at least 80% of the total pore volume is contained in pores with diameters in the range of from 0.1 to 10 ?m and at least 80% of the pore volume contained in the pores with diameters in the range of from 0.1 to 10 ?m is contained in pores with diameters in the range of from 0.3 to 10 ?m.Type: GrantFiled: November 18, 2011Date of Patent: January 22, 2013Assignee: Shell Oil CompanyInventors: William Herman Gerdes, John Robert Lockemeyer, Donald James Remus, Thomas Szymanski, Randall Clayton Yeates
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Publication number: 20120302800Abstract: Method of producing glycerol that includes mixing a peroxide stream with an olefenic alcohol stream to form a feed stream; processing the feed stream in a high shear device to produce a high shear dispersion of peroxide and olefinic alcohol, wherein the high shear device is configured with a rotor and a stator separated by a shear gap; and contacting the high shear dispersion with a catalyst in a reactor to produce glycerol.Type: ApplicationFiled: August 13, 2012Publication date: November 29, 2012Applicant: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8309771Abstract: A two-stage, gas phase process for manufacturing alkylene glycol (e.g., ethylene glycol) from an alkene (e.g., ethylene), oxygen and water, the process comprising the steps of: (A) Contacting under gas phase, oxidation conditions gaseous alkene and oxygen over a heterogeneous oxidation catalyst to produce a gaseous oxidation product comprising alkylene oxide, water and unreacted alkene; (B) Contacting under gas phase, hydrolysis conditions the gaseous oxidation product of (A) with added water over a heterogeneous hydrolysis catalyst to produce a gaseous alkylene glycol and unreacted alkene; and (C) Recycling the unreacted alkene of (B) to (A). The hydrolysis catalyst is selected from the group consisting of hydrotalcites, metal-loaded zeolites, phosphates, and metal-loaded ion-exchanged molecular sieves.Type: GrantFiled: July 31, 2009Date of Patent: November 13, 2012Assignee: Dow Technology Investments LLCInventors: Joseph C. Noronha, Elbert J. Campbell, Brian T. Keen, Dick A. Nagaki, Hwaili Soo, David A. Spears, John F. Szul
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Patent number: 7989664Abstract: Disclosed are methods for generating propylene glycol, ethylene glycol and other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols from biomass using hydrogen produced from the biomass. The methods involve reacting a portion of an aqueous stream of a biomass feedstock solution over a catalyst under aqueous phase reforming conditions to produce hydrogen, and then reacting the hydrogen and the aqueous feedstock solution over a catalyst to produce propylene glycol, ethylene glycal and the other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols. The disclosed methods can be run at lower temperatures and pressures, and allows for the production of oxygenated hydrocarbons without the need for hydrogen from an external source.Type: GrantFiled: July 12, 2010Date of Patent: August 2, 2011Assignee: Virent Energy Systems, Inc.Inventor: Randy D. Cortright
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Publication number: 20110054224Abstract: The invention provides a process for the preparation of an alkylene glycol from an alkene wherein conversion of alkylene oxide to alkylene glycol occurs in an alkylene oxide absorber and optionally in further reactors, and alkylene glycol is extracted from fat absorbent by contacting the fat absorbent with a lean solvent, thereby producing fat solvent, recovering alkylene glycol from the fat solvent and recycling the lean solvent.Type: ApplicationFiled: April 8, 2009Publication date: March 3, 2011Applicant: SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.Inventor: Dominicus Maria Rekers
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Publication number: 20100216958Abstract: Isobutene, isoprene, and butadiene are obtained from mixtures of C4 and/or C5 olefins by dehydrogenation. The C4 and/or C5 olefins can be obtained by dehydration of C4 and C5 alcohols, for example, renewable C4 and C5 alcohols prepared from biomass by thermochemical or fermentation processes. Isoprene or butadiene can be polymerized to form polymers such as polyisoprene, polybutadiene, synthetic rubbers such as butyl rubber, etc. in addition, butadiene can be converted to monomers such as methyl methacrylate, adipic acid, adiponitrile, 1,4-butadiene, etc. which can then be polymerized to form nylons, polyesters, polymethylmethacrylate etc.Type: ApplicationFiled: February 24, 2010Publication date: August 26, 2010Inventors: Matthew W. Peters, Joshua D. Taylor, Leo E. Manzer, David E. Henton
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Publication number: 20100094065Abstract: A process for recovering monoethylene glycol from a catalyst bleed stream is disclosed. The process comprises combining the catalyst bleed stream with a heavies stream comprising at least 40 wt % diethylene glycol, to provide a combined stream and distilling the combined stream to provide a first stream comprising monoethylene glycol and a second stream comprising diethylene glycol.Type: ApplicationFiled: October 9, 2009Publication date: April 15, 2010Inventor: Mathias Jozef Paul SLAPAK
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Publication number: 20100036176Abstract: A two-stage, gas phase process for manufacturing alkylene glycol (e.g., ethylene glycol) from an alkene (e.g., ethylene), oxygen and water, the process comprising the steps of: (A) Contacting under gas phase, oxidation conditions gaseous alkene and oxygen over a heterogeneous oxidation catalyst to produce a gaseous oxidation product comprising alkylene oxide, water and unreacted alkene; (B) Contacting under gas phase, hydrolysis conditions the gaseous oxidation product of (A) with added water over a heterogeneous hydrolysis catalyst to produce a gaseous alkylene glycol and unreacted alkene; and (C) Recycling the unreacted alkene of (B) to (A). The hydrolysis catalyst is selected from the group consisting of hydrotalcites, metal-loaded zeolites, phosphates, and metal-loaded ion-exchanged molecular sieves.Type: ApplicationFiled: July 31, 2009Publication date: February 11, 2010Inventors: Joseph C. Noronha, Elbert J. Campbell, Brian T. Keen, Dick A. Nagaki, Hwaili Soo, David A. Spears, John F. Szul
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Publication number: 20090299104Abstract: A catalyst for partial oxidation of olefin, which comprises silver or silver oxide and an alkali metal or a compound thereof supported on an ?-alumina carrier containing silicon or a compound thereof, wherein the silicon or the compound thereof exists at a position substantially identical to that of a particle of the alkali metal or the compound thereof, a preparation method thereof, and a process for preparing olefin oxide which comprises subjecting olefin to vapor-phase oxidation with a molecular oxygen-containing gas in the presence of the catalyst.Type: ApplicationFiled: May 1, 2007Publication date: December 3, 2009Inventors: Masahide Shima, Masafumi Sugio, Tatsuya Kawabata
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Publication number: 20090253944Abstract: The invention provides a process for preparing ethylene oxide and/or propylene oxide by contacting ethylene and/or propylene with an oxidizing agent, wherein (i) the reaction takes place in a microreaction system (p-reactor) and (ii) the oxidizing agent used is a peroxo compound.Type: ApplicationFiled: March 23, 2007Publication date: October 8, 2009Applicant: Cognis IP Management GmbHInventors: Bernhard Gutsche, Bernd Fabry, Stefan Franzen
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Publication number: 20090143627Abstract: The invention provides a process for the preparation of an alkylene glycol from an alkene. A gas composition from an alkylene oxide reactor is supplied to an alkylene oxide absorber comprising a column of vertically stacked trays or comprising a packed column. Lean absorbent comprising at least 20 wt % water is supplied to the alkylene oxide absorber and is contacted with the gas composition in the presence of one or more catalysts that promote carboxylation and hydrolysis. At least 50% of the alkylene oxide entering the alkylene oxide absorber is converted in the alkylene oxide absorber. Fat absorbent is withdrawn from the absorber, is optionally supplied to finishing reactors and/or a flash vessel or light ends stripper, and is subsequently subjected to dehydration and purification to provide a purified alkylene glycol product stream.Type: ApplicationFiled: August 14, 2008Publication date: June 4, 2009Inventors: Eugene Marie Godfried Andre Van Kruchten, Dominicus Maria Rekers, Mathias Jozef Paul Slapak
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Publication number: 20080300431Abstract: A catalytic process for preparing a monoalkylene glycol from a corresponding alkylene oxide utilizing an ion exchange resin and a reactor in which an upflow process is used is provided. In particular, the process includes reacting water and an alkylene oxide in at least one reactor under conditions to form an alkylene glycol, wherein the at least one reactor includes an ion exchange resin and the reactor is operating in an upflow direction.Type: ApplicationFiled: May 30, 2007Publication date: December 4, 2008Applicant: SD LIZENZVERWERTUNGSGESELLSCHAFT MBH & CO. KGInventors: William Crudge, Jaap Willem van Hal, Xiankuan Zhang
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Supported ruthenium nanoparticle catalyst for cis -dihydroxylation and oxidative cleavage of alkenes
Patent number: 7393985Abstract: The present invention relates to the use of nanosized metal particles (e.g., ruthenium) grafted on inert solid support for oxidation of alkenes. The supported metal catalyst can effect cis-dihydroxylation and oxidative cleavage of alkenes to give the respective cis-diols and carbonyl products.Type: GrantFiled: April 19, 2005Date of Patent: July 1, 2008Assignee: The University of Hong KongInventors: Chi-Ming Che, Wing-Yiu Yu, Chi-Ming Ho -
Patent number: 7335799Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.Type: GrantFiled: December 23, 2003Date of Patent: February 26, 2008Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 6852874Abstract: A process for catalyzing asymmetric dihydroxylations of olefins employs an Os(VI) complex as a catalytic intermediate in the formation of chiral vicinal diol products. The process requires a chiral bidentate ligand that favors diol formation in the “second cycle” of asymmetric dihydroxylation.Type: GrantFiled: August 28, 2001Date of Patent: February 8, 2005Assignee: The Scripps Research InstituteInventors: K. Barry Sharpless, Malin Andersson, Robert Epple, Valery Fokin
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Patent number: 6780810Abstract: The present invention relates to a multifunctional reusable catalyst and to a process for the preparation thereof on a single matrix of the support to perform multicomponent reaction in a single pot. The multifunctional catalysts of the invention are useful for the synthesis of chiral vicinal diols by tandem and/or simultaneous reactions involving Heck coupling, N-oxidation and AD reaction of olefins in presence of cinchona alkaloid compounds both as an native one and immobilized one in the said matrix support. This invention also relates to a process for preparing vicinal diols by asymmetric dihydroxylation of olefins in presence of cinchona alkaloid compounds employing reusable multifunctional catalysts as heterogeneous catalysts in place of soluble osmium catalysts.Type: GrantFiled: March 13, 2002Date of Patent: August 24, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Sateesh Madhi, Mannepalli Lakshmi Kantam
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Patent number: 6740785Abstract: Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.Type: GrantFiled: July 26, 2002Date of Patent: May 25, 2004Assignee: The University of KansasInventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
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Publication number: 20040097764Abstract: A process for producing 1,3-propanediol, comprising:Type: ApplicationFiled: September 2, 2003Publication date: May 20, 2004Inventors: Takashi Tsunoda, Kouji Nomura
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Patent number: 6646168Abstract: The present invention provides a supported osmate useful as a reusable catalyst in the preparation of vicinal diols. The present invention also relates to a process for the preparation of supported osmates of the formula (S—NR3)2OsO4.nH2O wherein S is a support, R is an alkyl group, n is the number of water molecules and use thereof in the preparation of vicinal diols by asymmetric dihydroxylation (AD) of olefins in presence of cinchona alkaloid compounds.Type: GrantFiled: March 13, 2002Date of Patent: November 11, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Mannepalli Lakshmi Kantam, Kondapuram Vijaya Raghavan
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Publication number: 20030153794Abstract: The present invention discloses a process for the preparation of a novel heterogeneous osmate catalyst of the general formula (S—NR3)2OsO4.nH2O wherein S is a support, R is an alkyl group, n is the number of water molecules by reacting potassium osmate with supported quaternary ammonium species in an aqueous solvent.Type: ApplicationFiled: February 14, 2003Publication date: August 14, 2003Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH.Inventors: Boyapati M. Choudary, Naidu S. Chowdari, Mannepalli L. Kantam, Kondapuram V. Raghavan
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Publication number: 20030105367Abstract: The present invention provides a supported osmate useful as a reusable catalyst in the preparation of vicinal diols. The present invention also relates to a process for the preparation of supported osmates of the formula (S—NR3)2OsO4.nH2O wherein S is a support, R is an alkyl group, n is the number of water molecules and use thereof in the preparation of vicinal diols by asymmetric dihydroxylation (AD) of olefins in presence of cinchona alkaloid compounds.Type: ApplicationFiled: March 13, 2002Publication date: June 5, 2003Inventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Mannepalli Lakshmi Kantam, Kondapuram Vijaya Raghavan
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Patent number: 6472570Abstract: This invention relates to process for asymmetric dihydroxylation of olefins using osmium catalysts to obtain monofunctional, bifunctional, and/or polyfunctional chiral 1,2-diols of the formula (I) R1R2C(OH)—C(OH)R3R4 (I) where R1 to R4 are defined herein, by reacting an olefin of the formula (II) R1R2C═CR3R4 (II) where R1 to R4 are defined as for formula (I), with molecular oxygen in the presence of an osmium compound and a chiral amine ligand in water or a water-containing solvent mixture at a pH of from 8.5 to 13.Type: GrantFiled: October 19, 2001Date of Patent: October 29, 2002Assignee: Bayer AktiengesellschaftInventors: Matthias Beller, Christian Döbler, Gerald Mehltretter, Uta Sundermeier
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Patent number: 6387033Abstract: LDH-osmate of the formula [MII(1−x)MIIIx(OH)2][OsO42−]x/2.zH2O wherein MII is a divalent cation selected from the group consisting of Mg2+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+ and Ca2+ and MIII is a trivalent ion selected from the group consisting of Al3+, Cr3+, Mn3+, Fe3+ and Co3+, and x is the mole fraction having integral value ranging from 0.2 to 0.33, and z is the number of water molecules and ranges from 1 to 4, useful as, a catalyst, and a process for the preparation thereof and use thereof to manufacture vicinal diols.Type: GrantFiled: November 22, 2000Date of Patent: May 14, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Mannepalli Lakshmi Kantam, Kondapuram Vijaya Raghavan, Chinta Venkat Reddy Reddy
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Patent number: 6194615Abstract: The present invention relates to the composition, process of preparation, and use of novel derivatives prepared from 1,5-bis-(4′-carbomethoxyphenyl)-1,4-pentadien-3-one. These novel compositions can act as crosslinkers with polyfunctional monomeric, oligomeric, and/or polymeric anhydrides, esters, carboxylic acids, isocyantes, epoxies, carbonates, acetoacetates, and alkoxylated melamines.Type: GrantFiled: June 17, 1999Date of Patent: February 27, 2001Assignee: Eastman Chemical CompanyInventors: Philip Conrad Heidt, Matthew Lynn Elliott
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Patent number: 6100412Abstract: A process for the production of an epoxide and/or its corresponding vicinal diol by a reaction of an olefinic compound with hydrogen peroxide, wherein the reaction is performed in the presence of a carbon dioxide phase at a temperature and a pressure above the critical point of carbon dioxide.Type: GrantFiled: September 10, 1999Date of Patent: August 8, 2000Assignee: Degussa-Huls AGInventors: Georg Thiele, Shane A. Nolan, James S. Brown, Jie Lu, Brandon C. Eason, Charles A. Eckert, Charles L. Liotta
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Patent number: 5959163Abstract: Disclosed is a process for the preparation of 2-butene-1,4-diol comprising contacting a mixture of water and 1,2-epoxy-3-butene with a catalyst comprising a metal halide, zeolite and a non-protic solvent.Type: GrantFiled: September 4, 1997Date of Patent: September 28, 1999Assignee: The Dow Chemical CompanyInventors: Thomas J. Remans, Pierre A. Jacobs, Johan Martens, Dominicus A. G. van Oeffelen, Mathias H. G. Steijns
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Patent number: 5892066Abstract: Propylene is oxidized with molecular oxygen in the liquid phase to form products including propylene oxide, propylene glycol, propylene glycol esters, allyl alcohol, acrolein and acetal, the acrolein is hydrogenated to allyl alcohol, the acetol is hydrogenated to propylene glycol, the propylene glycol esters are hydrolyzed to propylene glycol, and propylene oxide, propylene glycol and allyl alcohol are recovered as products.Type: GrantFiled: December 12, 1997Date of Patent: April 6, 1999Assignee: ARCO Chemical Technology, L.P.Inventor: Roger A. Grey
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Patent number: 5688975Abstract: Molecular sieve compositions have been synthesized which are resistant to the loss of framework atoms. Specifically, the molecular sieves of the invention have the empirical formulamA: (M.sub.w Al.sub.x Si.sub.y)O.sub.2where A is at least one rare earth metal, M is chromium or titanium and "m", "w", "x" and "y" are the mole fractions of A, M, Al and Si respectively. Applicants have discovered that the rare earth metals prevent loss of chromium and titanium from the framework and degradation of the molecular sieve. Along with the composition, a process for preparing the composition and processes using the composition are disclosed and claimed.Type: GrantFiled: April 10, 1996Date of Patent: November 18, 1997Assignee: UOPInventors: Vinayan Nair, Deng-Yang Jan, Robert Lyle Patton, Ben A. Wilson, Donald F. Best
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Patent number: 5530167Abstract: Disclosed is an improved process for the preparation of 1,4-butenediol by the hydrolysis of 3,4-epoxy-1-butene (EpB) wherein a mixture of EpB and water is contacted with a catalyst comprising a catalyst support material an copper in a positive valence state.Type: GrantFiled: August 21, 1995Date of Patent: June 25, 1996Assignee: Eastman Chemical CompanyInventor: Gerald C. Tustin
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Patent number: 5516929Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.Type: GrantFiled: February 12, 1993Date of Patent: May 14, 1996Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
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Patent number: 5344946Abstract: The present invention provides a process for the preparation of vicinal diols and/or epoxides by the oxidation of olefinically-unsaturated compounds with the use of an inorganic heptavalent rhenium compound as catalyst and of hydrogen peroxide as oxidation agent, wherein the reaction is carried out in a solvent selected from the group consisting of organic phosphoric acid esters and ethers with a boiling point above 50.degree. C. under atmospheric conditions.Type: GrantFiled: May 20, 1993Date of Patent: September 6, 1994Assignee: Solvay Interox GmbHInventors: Siegfried Warwel, Mark R. Klaas, Michael Sojka
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Patent number: 5268493Abstract: An .alpha.-olefin oxide is produced with an enhanced reaction selectivity by a method in which an .alpha.-olefin having 6 to 30 carbon atoms is epoxidized in an aqueous solution containing hydrogen peroxide, acetic acid, an acid catalyst, for example, sulfuric acid, and a side reaction-inhibiting agent consisting of a water-soluble neutral salt, for example, sodium sulfate, in an amount of 2 to 30% based on the total weight of the aqueous solution, by an in-situ method, while maintaining the pH of the aqueous solution at a level of 0 to 1, and the resultant reaction product is collected.Type: GrantFiled: December 3, 1992Date of Patent: December 7, 1993Assignee: Nippon Peroxide Co., Ltd.Inventors: Ryuichi Kayama, Hiroshi Igarashi, Toshio Suzuki
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Patent number: 5260461Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, an aqueous solution, a base, a ferricyanide salt and an osmium-containing compound are combined. The chiral ligand is an alkaloid or alkaloid derivative linked to an organic substituent of at least 300 daltons molecular weight through a planar aromatic spacer group. The organic substituent can be another alkaloid or alkaloid derivative. With the described chiral ligands, asymmetric dihydroxylation of olefins with high yields and enantiomeric excesses are achieved.Type: GrantFiled: October 10, 1991Date of Patent: November 9, 1993Assignee: Massachusetts Institute of TechnologyInventors: Jens Hartung, K. Barry Sharpless
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Patent number: 5227543Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant, an osmium-containing compound and an organic soluble anion are combined. The presence of the organic soluble anion allows the asymmetric dihydroxylation reaction to occur rapidly and the amount of olefin that is diydroxylated is high with concomitantly less chiral ligand and osmium-containing catalyst than previously achieved.Type: GrantFiled: October 10, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Wihelm K. Amberg
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Patent number: 5210336Abstract: A process is provided for the conversion of an olefin to the corresponding glycol wherein a mixture of olefin, oxygen, carbon dioxide and water is reacted in a solvent at supercritical conditions with respect to the reaction mixture.Type: GrantFiled: January 24, 1992Date of Patent: May 11, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Anne M. Gaffney, John A. Sofranko
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Patent number: 5166372Abstract: Olefins are epoxidized by hydrogen peroxide in the presence of an organorhenium oxide catalyst and an alkyl aryl secondary alcohol solvent. High yields of epoxides with minimal non-selective loss of either hydrogen peroxide or olefin are realized. The epoxidation may comprise one step of an integrated process wherein an oxidant mixture is generated by molecular oxygen oxidation of the alkyl aryl secondary alcohol and used directly in the epoxidation without further purification or extraction.Type: GrantFiled: February 7, 1992Date of Patent: November 24, 1992Assignee: Arco Chemical Technology, L.P.Inventors: Guy L. Crocco, Wilfred F. Shum, John G. Zajacek, Haven S. Kesling, Jr.
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Patent number: 5159123Abstract: Disclosed is an improvement in a process for polymerizing 1,3-butadiene selectively to form relatively low molecular weight hydroxyl-terminated polybutadiene oligomers in the presence of an aqueous solution of hydrogen peroxide which comprises the use of a solvent selected from the group consisting of alkylene glycol monoalkyl ether acetates and aliphatic glycol ether carboxylates to produce butadiene oligomers having a high degree of OH functionality and suppression of formation of solid or gel-type insoluble rubber by-products.Type: GrantFiled: May 2, 1991Date of Patent: October 27, 1992Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Edward T. Marquis
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Patent number: 5126494Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallo-chloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.Type: GrantFiled: April 23, 1990Date of Patent: June 30, 1992Assignee: Massachusetts Institute of TechnologyInventors: Declan Gilheany, Byeong M. Kim, Hoi-Lun Kwong, K. Barry Sharpless, Tomoyuki Shibata
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Patent number: 5105028Abstract: Process for preparing one or more hetero-atoms containing hydrocarbons by contacting one or more hydrocarbons with a plasma-generated system derived from a source containing hydrogen atoms(s) and at least one hetero-atom in which process the plasma-generated system in contacted with the hydrocarbon(s) in liquid for and/or in gaseous form under conditions which allow absorption of heat released during the process of preparing said hetero-atom(s) containing hydrocarbons.Type: GrantFiled: November 29, 1990Date of Patent: April 14, 1992Assignee: Shell Oil CompanyInventors: Jacques J. J. Dufour, Laurent Pelsez, Bruno Peltier