Preparing By Hydroxylation At Point Of Ethylenic Unsaturation Patents (Class 568/860)
  • Patent number: 10526300
    Abstract: 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: Grant
    Filed: December 13, 2016
    Date of Patent: January 7, 2020
    Assignee: SHELL OIL COMPANY
    Inventors: Wayne Errol Evans, Jesse Raymond Black, Michael Francis Lemanski
  • Publication number: 20150119542
    Abstract: 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: Application
    Filed: October 17, 2014
    Publication date: April 30, 2015
    Inventors: Walter Weissman, Sumathy Raman, Mark A. Greaney
  • Publication number: 20150087866
    Abstract: 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: Application
    Filed: August 30, 2012
    Publication date: March 26, 2015
    Applicants: UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL-UFRGS, BRASKEM S.A.
    Inventor: Michèle Oberson De Souza
  • Publication number: 20140296570
    Abstract: 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: Application
    Filed: December 20, 2011
    Publication date: October 2, 2014
    Applicant: Exxonmobile Chemical Patents Inc.
    Inventors: Paul F. Keusenkothen, Frank Hershkowitz
  • Patent number: 8742180
    Abstract: 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: Grant
    Filed: November 13, 2012
    Date of Patent: June 3, 2014
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Brian A. Salisbury, Jenny M. Oran Osment
  • Publication number: 20140135537
    Abstract: 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: Application
    Filed: November 13, 2012
    Publication date: May 15, 2014
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Brian A. Salisbury, Jenny M. Oran Osment
  • Publication number: 20140128620
    Abstract: 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: Application
    Filed: January 13, 2014
    Publication date: May 8, 2014
    Applicant: SHELL OIL COMPANY
    Inventors: Eugene Marie Godfried Andre VAN KRUCHTEN, Dominicus Maria REKERS, Mathias Jozef Paul SLAPAK
  • Publication number: 20140058138
    Abstract: 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: Application
    Filed: June 11, 2013
    Publication date: February 27, 2014
    Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
  • Publication number: 20130317238
    Abstract: 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: Application
    Filed: December 8, 2011
    Publication date: November 28, 2013
    Inventors: Pravansu S. Mohanty, Swaminathan Ramesh
  • Patent number: 8502000
    Abstract: 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: Grant
    Filed: June 23, 2008
    Date of Patent: August 6, 2013
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 8357825
    Abstract: 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: Grant
    Filed: November 18, 2011
    Date of Patent: January 22, 2013
    Assignee: Shell Oil Company
    Inventors: William Herman Gerdes, John Robert Lockemeyer, Donald James Remus, Thomas Szymanski, Randall Clayton Yeates
  • Patent number: 8357813
    Abstract: 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: Grant
    Filed: November 18, 2011
    Date of Patent: January 22, 2013
    Assignee: Shell Oil Company
    Inventors: William Herman Gerdes, John Robert Lockemeyer, Donald James Remus, Thomas Szymanski, Randall Clayton Yeates
  • Publication number: 20120302800
    Abstract: 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: Application
    Filed: August 13, 2012
    Publication date: November 29, 2012
    Applicant: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 8309771
    Abstract: 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: Grant
    Filed: July 31, 2009
    Date of Patent: November 13, 2012
    Assignee: Dow Technology Investments LLC
    Inventors: Joseph C. Noronha, Elbert J. Campbell, Brian T. Keen, Dick A. Nagaki, Hwaili Soo, David A. Spears, John F. Szul
  • Patent number: 7989664
    Abstract: 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: Grant
    Filed: July 12, 2010
    Date of Patent: August 2, 2011
    Assignee: Virent Energy Systems, Inc.
    Inventor: Randy D. Cortright
  • Publication number: 20110054224
    Abstract: 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: Application
    Filed: April 8, 2009
    Publication date: March 3, 2011
    Applicant: SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.
    Inventor: Dominicus Maria Rekers
  • Publication number: 20100216958
    Abstract: 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: Application
    Filed: February 24, 2010
    Publication date: August 26, 2010
    Inventors: Matthew W. Peters, Joshua D. Taylor, Leo E. Manzer, David E. Henton
  • Publication number: 20100094065
    Abstract: 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: Application
    Filed: October 9, 2009
    Publication date: April 15, 2010
    Inventor: Mathias Jozef Paul SLAPAK
  • Publication number: 20100036176
    Abstract: 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: Application
    Filed: July 31, 2009
    Publication date: February 11, 2010
    Inventors: Joseph C. Noronha, Elbert J. Campbell, Brian T. Keen, Dick A. Nagaki, Hwaili Soo, David A. Spears, John F. Szul
  • Publication number: 20090299104
    Abstract: 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: Application
    Filed: May 1, 2007
    Publication date: December 3, 2009
    Inventors: Masahide Shima, Masafumi Sugio, Tatsuya Kawabata
  • Publication number: 20090253944
    Abstract: 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: Application
    Filed: March 23, 2007
    Publication date: October 8, 2009
    Applicant: Cognis IP Management GmbH
    Inventors: Bernhard Gutsche, Bernd Fabry, Stefan Franzen
  • Publication number: 20090143627
    Abstract: 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: Application
    Filed: August 14, 2008
    Publication date: June 4, 2009
    Inventors: Eugene Marie Godfried Andre Van Kruchten, Dominicus Maria Rekers, Mathias Jozef Paul Slapak
  • Publication number: 20080300431
    Abstract: 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: Application
    Filed: May 30, 2007
    Publication date: December 4, 2008
    Applicant: SD LIZENZVERWERTUNGSGESELLSCHAFT MBH & CO. KG
    Inventors: William Crudge, Jaap Willem van Hal, Xiankuan Zhang
  • Patent number: 7393985
    Abstract: 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: Grant
    Filed: April 19, 2005
    Date of Patent: July 1, 2008
    Assignee: The University of Hong Kong
    Inventors: Chi-Ming Che, Wing-Yiu Yu, Chi-Ming Ho
  • Patent number: 7335799
    Abstract: 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: Grant
    Filed: December 23, 2003
    Date of Patent: February 26, 2008
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Patent number: 6852874
    Abstract: 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: Grant
    Filed: August 28, 2001
    Date of Patent: February 8, 2005
    Assignee: The Scripps Research Institute
    Inventors: K. Barry Sharpless, Malin Andersson, Robert Epple, Valery Fokin
  • Patent number: 6780810
    Abstract: 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: Grant
    Filed: March 13, 2002
    Date of Patent: August 24, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Sateesh Madhi, Mannepalli Lakshmi Kantam
  • Patent number: 6740785
    Abstract: 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: Grant
    Filed: July 26, 2002
    Date of Patent: May 25, 2004
    Assignee: The University of Kansas
    Inventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
  • Publication number: 20040097764
    Abstract: A process for producing 1,3-propanediol, comprising:
    Type: Application
    Filed: September 2, 2003
    Publication date: May 20, 2004
    Inventors: Takashi Tsunoda, Kouji Nomura
  • Patent number: 6646168
    Abstract: 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: Grant
    Filed: March 13, 2002
    Date of Patent: November 11, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Mannepalli Lakshmi Kantam, Kondapuram Vijaya Raghavan
  • Publication number: 20030153794
    Abstract: 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: Application
    Filed: February 14, 2003
    Publication date: August 14, 2003
    Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH.
    Inventors: Boyapati M. Choudary, Naidu S. Chowdari, Mannepalli L. Kantam, Kondapuram V. Raghavan
  • Publication number: 20030105367
    Abstract: 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: Application
    Filed: March 13, 2002
    Publication date: June 5, 2003
    Inventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Mannepalli Lakshmi Kantam, Kondapuram Vijaya Raghavan
  • Patent number: 6472570
    Abstract: 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: Grant
    Filed: October 19, 2001
    Date of Patent: October 29, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Matthias Beller, Christian Döbler, Gerald Mehltretter, Uta Sundermeier
  • Patent number: 6387033
    Abstract: 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: Grant
    Filed: November 22, 2000
    Date of Patent: May 14, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Naidu Sreenivasa Chowdari, Mannepalli Lakshmi Kantam, Kondapuram Vijaya Raghavan, Chinta Venkat Reddy Reddy
  • Patent number: 6194615
    Abstract: 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: Grant
    Filed: June 17, 1999
    Date of Patent: February 27, 2001
    Assignee: Eastman Chemical Company
    Inventors: Philip Conrad Heidt, Matthew Lynn Elliott
  • Patent number: 6100412
    Abstract: 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: Grant
    Filed: September 10, 1999
    Date of Patent: August 8, 2000
    Assignee: Degussa-Huls AG
    Inventors: Georg Thiele, Shane A. Nolan, James S. Brown, Jie Lu, Brandon C. Eason, Charles A. Eckert, Charles L. Liotta
  • Patent number: 5959163
    Abstract: 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: Grant
    Filed: September 4, 1997
    Date of Patent: September 28, 1999
    Assignee: The Dow Chemical Company
    Inventors: Thomas J. Remans, Pierre A. Jacobs, Johan Martens, Dominicus A. G. van Oeffelen, Mathias H. G. Steijns
  • Patent number: 5892066
    Abstract: 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: Grant
    Filed: December 12, 1997
    Date of Patent: April 6, 1999
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Roger A. Grey
  • Patent number: 5688975
    Abstract: 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: Grant
    Filed: April 10, 1996
    Date of Patent: November 18, 1997
    Assignee: UOP
    Inventors: Vinayan Nair, Deng-Yang Jan, Robert Lyle Patton, Ben A. Wilson, Donald F. Best
  • Patent number: 5530167
    Abstract: 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: Grant
    Filed: August 21, 1995
    Date of Patent: June 25, 1996
    Assignee: Eastman Chemical Company
    Inventor: Gerald C. Tustin
  • Patent number: 5516929
    Abstract: 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: Grant
    Filed: February 12, 1993
    Date of Patent: May 14, 1996
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
  • Patent number: 5344946
    Abstract: 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: Grant
    Filed: May 20, 1993
    Date of Patent: September 6, 1994
    Assignee: Solvay Interox GmbH
    Inventors: Siegfried Warwel, Mark R. Klaas, Michael Sojka
  • Patent number: 5268493
    Abstract: 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: Grant
    Filed: December 3, 1992
    Date of Patent: December 7, 1993
    Assignee: Nippon Peroxide Co., Ltd.
    Inventors: Ryuichi Kayama, Hiroshi Igarashi, Toshio Suzuki
  • Patent number: 5260461
    Abstract: 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: Grant
    Filed: October 10, 1991
    Date of Patent: November 9, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Jens Hartung, K. Barry Sharpless
  • Patent number: 5227543
    Abstract: 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: Grant
    Filed: October 10, 1991
    Date of Patent: July 13, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Wihelm K. Amberg
  • Patent number: 5210336
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: May 11, 1993
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Anne M. Gaffney, John A. Sofranko
  • Patent number: 5166372
    Abstract: 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: Grant
    Filed: February 7, 1992
    Date of Patent: November 24, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Guy L. Crocco, Wilfred F. Shum, John G. Zajacek, Haven S. Kesling, Jr.
  • Patent number: 5159123
    Abstract: 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: Grant
    Filed: May 2, 1991
    Date of Patent: October 27, 1992
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Edward T. Marquis
  • Patent number: 5126494
    Abstract: 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: Grant
    Filed: April 23, 1990
    Date of Patent: June 30, 1992
    Assignee: Massachusetts Institute of Technology
    Inventors: Declan Gilheany, Byeong M. Kim, Hoi-Lun Kwong, K. Barry Sharpless, Tomoyuki Shibata
  • Patent number: 5105028
    Abstract: 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: Grant
    Filed: November 29, 1990
    Date of Patent: April 14, 1992
    Assignee: Shell Oil Company
    Inventors: Jacques J. J. Dufour, Laurent Pelsez, Bruno Peltier