Preparing From Ether Patents (Class 568/907)
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Patent number: 11465949Abstract: Systems and methods for the production of a high purity isoamylene product. The isoamylene in a mixed hydrocarbon stream may initially be converted to TAME via etherification, and a subsequent decomposition of the TAME may result in a high purity isoamylene stream with very low impurities that is suitable for a variety of petrochemical applications, such as for use in the production of fragrances, pesticides, peroxides, polymer antioxidants, UV stabilizers and hydrocarbon resins.Type: GrantFiled: November 2, 2021Date of Patent: October 11, 2022Assignee: LUMMUS TECHNOLOGY LLCInventors: Rosette Barias, Liang Chen, Michael Jon Scott
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Patent number: 9249074Abstract: The present invention relates to a new and improved synthesis of tetrahydromyrcenol (IUPAC name: 2,6-dimethyl-2-octanol).Type: GrantFiled: November 28, 2013Date of Patent: February 2, 2016Assignee: DSM IP ASSETS B.V.Inventors: Raphael Beumer, Werner Bonrath, Jonathan Alan Medlock
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Patent number: 9242920Abstract: An integrated process for the production of acetic acid by carbonylating dimethyl ether with synthesis gas to form methyl acetate and unreacted synthesis gas, utilizing the unreacted synthesis gas to produce methanol, dehydrating and hydrolyzing a mixture of methyl acetate and methanol to produce acetic acid and dimethyl ether and recovering acetic acid therefrom.Type: GrantFiled: December 19, 2013Date of Patent: January 26, 2016Assignee: BP CHEMICALS LIMITEDInventor: Timothy Crispin Bristow
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Patent number: 9115046Abstract: A process for producing ethanol from synthesis gas by reacting the hydrogen and carbon monoxide of the synthesis gas to provide methanol, which then is subjected to dehydration to produce at least one ether, such as dimethyl ether. The ether, such as dimethyl ether, then is subjected to carbonylation with unreacted carbon monoxide from the synthesis gas to provide at least one acetate, such as methyl acetate. The acetate then is subjected to hydrogenolysis to produce ethanol.Type: GrantFiled: December 11, 2012Date of Patent: August 25, 2015Assignee: Enerkem, Inc.Inventors: David Lynch, Esteban Chornet, Charles Bureau, Stephane Marie-Rose
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Publication number: 20150080590Abstract: The invention relates to a process for the production of ethylene oxide, comprising the steps of: producing ethylene resulting in a stream comprising ethylene and ethane; separating the stream comprising ethylene and ethane into a stream comprising ethylene and ethane in which stream the amount of ethylene is greater than the amount of ethane and a stream comprising ethane and ethylene in which stream the amount of ethane is greater than the amount of ethylene; producing ethylene oxide by subjecting ethylene and ethane from the stream comprising ethylene and ethane, in which stream the amount of ethylene is greater than the amount of ethane, to oxidation conditions resulting in a stream comprising ethylene oxide, unconverted ethylene and ethane; and recovering ethylene oxide from the stream comprising ethylene oxide, unconverted ethylene and ethaneType: ApplicationFiled: March 25, 2013Publication date: March 19, 2015Inventors: Jovan Jovanovic, Timothy Michael Nisbet, Timothe Johannes Olthof, Michiel Johannes Franciscus Maria Verhaak
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Publication number: 20140275642Abstract: A method for preparing oxygenated hydrocarbons includes steps of: reacting a first heated hydrocarbon-containing gas stream with an oxygen-containing gas stream in a reactor for form a first product blend, recovering the energy generated in the reactor in order to preheat incoming hydrocarbon feed to the reactor and/or to drive endothermic reactions that generate synthesis gas, separating and condensing one or more liquid oxygenated hydrocarbons from the product stream, separating a reject stream from a recycle stream, mixing remaining gaseous hydrocarbon product from the recycle stream with the first hydrocarbon-containing gas stream after one reaction cycle, converting the first reject stream to a synthesis gas mixture, and converting the synthesis gas mixture to light alkanes to be blended with one or with oxygenates in an output stream to optionally form higher molecular weight oxygenates.Type: ApplicationFiled: March 15, 2013Publication date: September 18, 2014Applicant: GAS TECHNOLOGIES LLCInventors: Ian Lawrence Gaffney, Evan Michael Visser, Walter Breidenstein
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Publication number: 20140088316Abstract: A supported silver catalyst and use thereof in a process for producing an alkylene oxide, such as ethylene oxide, by the direct oxidation of an alkylene with oxygen or an oxygen-containing gas, wherein the catalyst provides improved stability and improved resilience to reactor upsets and timely recovery to substantially pre-upset levels of catalyst activity and/or efficiency. In some embodiments, the catalyst also exhibits improved activity. A catalyst capable of producing ethylene oxide at a selectivity of at least 87 percent while achieving a work rate of at least 184 kg/h/m3 at a temperature of no greater than 235° C. when operated in a process where the inlet feed to a reactor containing the catalyst comprises ethylene, oxygen, and carbon dioxide, wherein the concentration of carbon dioxide in the inlet feed is greater than or equal to 2 mole percent.Type: ApplicationFiled: September 21, 2012Publication date: March 27, 2014Inventors: Manuel A. W. Natal, Madan M. Bhasin, Hwaili Soo, Albert C. Liu
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Publication number: 20140087940Abstract: The present invention relates to mixed oxide compositions, to the use thereof as a catalyst for cleavage of alkyl tert-alkyl ethers or tertiary alcohols, and to a process for cleaving alkyl tert-alkyl ethers or tertiary alcohols to isoolefins and alcohol or water.Type: ApplicationFiled: March 7, 2012Publication date: March 27, 2014Applicant: Evonik Degussa GmbHInventors: Markus Winterberg, Christian Böing, Dietrich Maschmeyer, Asli Nau, Horst-Werner Zanthoff, Thomas Quandt, Christian Schulze Isfort
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Publication number: 20130178671Abstract: A process for producing ethanol from synthesis gas by reacting the hydrogen and carbon monoxide of the synthesis gas to provide methanol, which then is subjected to dehydration to produce at least one ether, such as dimethyl ether. The ether, such as dimethyl ether, then is subjected to carbonylation with unreacted carbon monoxide from the synthesis gas to provide at least one acetate, such as methyl acetate. The acetate then is subjected to hydrogenolysis to produce ethanol.Type: ApplicationFiled: December 11, 2012Publication date: July 11, 2013Inventors: David LYNCH, Esteban CHORNET, Charles BUREAU, Stephane MARIE-ROSE
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Publication number: 20130096352Abstract: The invention relates to a process for converting an alkyl tert-alkyl ether into an alkanol and an iso-alkane wherein the alkyl tert-alkyl ether is contacted with a hydrocracking catalyst in the presence of hydrogen under hydrocracking process conditions.Type: ApplicationFiled: October 16, 2012Publication date: April 18, 2013Applicant: SHELL OIL COMPANYInventor: SHELL OIL COMPANY
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Publication number: 20130078696Abstract: Carbon-containing materials, such as biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) or coal are processed to produce useful products, such as fuels. For example, systems are described that can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy materials, to produce ethanol.Type: ApplicationFiled: November 9, 2012Publication date: March 28, 2013Applicant: XYLCEO INC.Inventor: XYLCEO INC.
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Patent number: 8378156Abstract: Process for homologation of alcohol(s), by 1 introducing alcohol(s) into an etherification unit to produce alkyl ether(s), 2, introducing at least a part of the alkyl ether(s) from step 1, together with CO and optionally H2, into a carbonylation unit, in the presence of an acidic homogeneous or heterogeneous carbonylation catalyst, to produce alkyl ester(s), and 3, introducing at least a part of the alkyl ester(s) from step 2, together with H2, into a hydrogenation unit, to produce homologated alcohol(s). Optionally, at least a part of the homologated alcohol(s) from step 3 is recycled into the etherification unit of step 1. Alcohol(s) from the hydrogenation unit of step 3 are recovered.Type: GrantFiled: December 12, 2008Date of Patent: February 19, 2013Assignee: BP P.L.C.Inventors: Berian John Daniel, Benjamin Patrick Gracey, John Glenn Sunley
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Publication number: 20120058526Abstract: A method including: (a) selectively reacting a first sugar in a mixture which includes at least one second sugar to form a product mixture comprising a product of said first sugar; (b) separating said product of said first sugar from said product mixture; and (c) separating at least one of said at least one second sugar from said product mixture.Type: ApplicationFiled: September 2, 2011Publication date: March 8, 2012Applicant: HCL CleanTech LtdInventors: Robert Jansen, Aharon Eyal
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Publication number: 20110243821Abstract: The invention provides a process for reducing carbon dioxide comprising the step of exposing the carbon dioxide to a silane in the presence of an N-heterocyclic carbene (NHC) or a carboxylate thereof or both, to produce a methylsilyl ether.Type: ApplicationFiled: September 3, 2009Publication date: October 6, 2011Applicant: Agency for Science, Technology and ResearchInventors: Yugen Zhang, Jackie Y Ying, Siti Nurhanna Binti Riduan
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Publication number: 20110201850Abstract: Methods and systems for preparing alkylene glycols are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of alkylene oxides with water. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time.Type: ApplicationFiled: February 15, 2011Publication date: August 18, 2011Applicant: H R D CORPORATIONInventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
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Publication number: 20110124927Abstract: The present invention provides processes for selectively producing ethanol from syngas. In some variations, the process comprises converting biomass-derived syngas to dimethyl ether, carbonylating the dimethyl ether to methyl acetate, hydrogenating the methyl acetate to methanol and ethanol, and recovering the ethanol product. The methanol is preferably recycled by converting to hydrogen and carbon monoxide for introduction back into the process at distinct points. In certain variations of this invention, fresh syngas feed is introduced downstream of the first unit operation in the sequence. High yields of ethanol from biomass can be achieved according to the disclosed processes.Type: ApplicationFiled: November 22, 2010Publication date: May 26, 2011Applicant: Range Fuels, Inc.Inventors: Ronald C. STITES, Shakeel Tirmizi, Jerrod Hohman, Stephen Deutch
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Patent number: 7847135Abstract: The invention is a process to produce allyl alcohol from propylene oxide. The process comprises isomerizing propylene oxide in the presence of a lithium phosphate catalyst which contains boron and from 2000 to 4000 ppm sodium. The propylene oxide conversion is 37 percent or lower.Type: GrantFiled: October 30, 2009Date of Patent: December 7, 2010Assignee: Lyondell Chemical Technology, L.P.Inventor: Daniel F. White
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Publication number: 20100056816Abstract: This invention relates to shaped porous bodies of alpha-alumina platelets which are useful as catalyst carriers, filters, membrane reactors, and preformed bodies for composites. This invention also relates to processes of making such shaped bodies and processes for modifying the surface composition of alpha-alumina.Type: ApplicationFiled: July 20, 2007Publication date: March 4, 2010Inventors: Sten A. Wallin, Juliana G. Serafin, Madan M. Bhasin, Steven R. Lakso
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Patent number: 7538235Abstract: A process for preparing an epoxidation catalyst comprising silver and a high-selectivity dopant on a support, which process comprises depositing a base having a pKb of at most 3.5 when measured in water at 25° C., on the support prior to depositing silver on the support, and depositing silver and a high-selectivity dopant on the support; the epoxidation catalyst; and a process for preparing an olefin oxide by reacting an olefin with oxygen in the presence of the epoxidation catalyst.Type: GrantFiled: March 31, 2005Date of Patent: May 26, 2009Assignee: Shell Oil CompanyInventor: John Robert Lockemeyer
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Publication number: 20090131726Abstract: The invention relates to a method of making Group 3 and Group 4 mixed metal oxide catalyst suitable for the decomposition of ethers to alkenes and alkanols. In an embodiment, it relates to a method of making a cerium-zirconium mixed metal oxide catalyst. In an embodiment, the catalyst made by the process of the invention is used for the production of isopropanol (IPA) from isopropyl ether (IPE).Type: ApplicationFiled: November 17, 2008Publication date: May 21, 2009Inventors: James Clarke Vartuli, Doron Levin, Stephen John McCarthy
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Patent number: 7468465Abstract: The invention relates to a method of making Group 3 and Group 4 mixed metal oxide catalyst suitable for the decomposition of ethers to alkenes and alkanols. In an embodiment, it relates to a method of making a cerium-zirconium mixed metal oxide catalyst. In an embodiment, the catalyst made by the process of the invention is used for the production of isopropanol (IPA) from isopropyl ether (IPE).Type: GrantFiled: May 31, 2005Date of Patent: December 23, 2008Assignee: ExxonMobil Chemical Patents Inc.Inventors: James Clarke Vartuli, Doron Levin, Stephen John McCarthy
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Patent number: 7396964Abstract: The present invention relates to a process for preparing enantiomerically enriched 2-butanol and to its use.Type: GrantFiled: September 2, 2004Date of Patent: July 8, 2008Assignee: LANXESS Deutschland GmbHInventors: Björn Schlummer, Martin Stürmann
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Patent number: 7173158Abstract: The invention relates to a composition of matter comprising at least one metal from Group 3, at least one metal from Group 4, sulfur and oxygen, particularly useful as a catalyst for ether decomposition to alkanols and alkenes.Type: GrantFiled: May 31, 2005Date of Patent: February 6, 2007Assignee: ExxonMobil Chemical Patents Inc.Inventors: James Clarke Vartuli, Doron Levin, Stephen John McCarthy
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Patent number: 7161047Abstract: A process for preparing a secondary alcohol which is characterized in adding a primary or a secondary amine in the reaction system in case that the secondary alcohol is prepared by hydrogenating in the presence of a noble metal, an epoxy derivative represented by the following formula, wherein R1 and R2 are the same or different, an organic group not containing aldehyde group or ketone group therein or hydrogen atom, provided that both R1 and R2 are not simultaneously hydrogen atom.Type: GrantFiled: March 29, 2005Date of Patent: January 9, 2007Assignee: Daiso Co., Ltd.Inventors: Yasushi Miki, Daisuke Fukumoto, Masafumi Mikami
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Patent number: 7012039Abstract: An oxide catalyst composition for use in producing methacrolein or a mixture of methacrolein and methacrylic acid, wherein the oxide catalyst composition is represented by the formula (Mo+W)l2BiaAbBcFedXeSbfOg, wherein: A is at least one member selected from the group consisting of Y and the elements of the lanthanoid series exclusive of Pm; B is at least one member selected from the group consisting of K, Rb and Cs; X is Co solely, or a mixture of Co and at least one member selected from the group consisting of Mg and Ni; and a, b, c, d, e, f and g are, respectively, the atomic ratios of Bi, A, B, Fe, X, Sb and O, relative to twelve atoms of the total of Mo and W, wherein the atomic ratios (a to f) of the elements and the relationship between the amounts of the elements are chosen so as to satisfy specific requirements.Type: GrantFiled: December 20, 2002Date of Patent: March 14, 2006Assignee: Asahi Kasei Chemicals CorporationInventors: Toru Watanabe, Osamu Nagano
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Patent number: 6906229Abstract: The invention relates to the production of isopropyl alcohol from di-isopropyl ether by catalytic distillation. The process solves, in particular, problems associated with the Sulfuric Acid Process.Type: GrantFiled: February 29, 2000Date of Patent: June 14, 2005Assignee: ExxonMobil Chemical Patents, Inc.Inventor: Paul E. Burton
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Patent number: 6790999Abstract: Disclosed is a process for the continuous, semi-continuous or batch production of 3-buten-1-ol from 3,4-epoxy-1-butene wherein 3,4-epoxy-1-butene and formic acid are fed to a reaction zone having a catalyst solution comprising a palladium(0) compound, a tertiary phosphine, a trialkylamine and an organic solvent. Preferably in the operation of this invention, 3-buten-1-ol product and reaction side products serve as the organic solvent for the process. The preferred mode of operation is continuous addition of reactants to the reaction mixture with simultaneous, continuous distillation of a reaction product comprising 3-buten-1-ol.Type: GrantFiled: February 28, 2003Date of Patent: September 14, 2004Assignee: Eastman Chemical CompanyInventor: Stephen Neal Falling
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Process for the cleavage of alkyl tert-alkyl ethers into isoolefins and alkanols over acid catalysts
Patent number: 6552236Abstract: Alkyl tert-alkyl ethers are cleaved into the corresponding isoolefins and alkanols by a process comprising acid-catalyzed reactive distilling an alkyl tert-alkyl ether fed into the reaction zone of a reactive distillation apparatus as an azeotrope of the alkyl tert-alkyl ether and the corresponding alkanol, wherein the reactive distillation apparatus is configured from bottom to top as a bottom zone, at least one distillation zone and a reaction zone. The process is suitable for the cleavage of primary, secondary and tertiary alkyl tert-alkyl ethers, in particular MTBE.Type: GrantFiled: April 25, 2001Date of Patent: April 22, 2003Assignee: OXENO Olefinchemie GmbHInventors: Michael Sakuth, Axel Tuchlenski, Dieter Reusch, Andreas Beckman -
Patent number: 6518465Abstract: A process for hydrolyzing an alkyl ester to produce a carboxylic acid product and an ether product, the process includes the steps of introducing into a reaction zone of a reactive distillation column a feed containing the alkyl ester wherein the reaction zone is at a temperature and pressure to preferentially produce an ether from the ester; and recovering the ether and the carboxylic acid.Type: GrantFiled: October 13, 2001Date of Patent: February 11, 2003Assignee: Eastman Chemical CompanyInventors: Craig Alan Hoyme, Edwin Franklin Holcombe, III
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Publication number: 20030009063Abstract: A process for producing isobutylene and methanol, comprising decomposing methyl-tert-butylether into isobutylene and methanol, and separating into isobutylene and methanol, thereby individually recovering isobutylene and methanol, the process comprising the following steps:Type: ApplicationFiled: June 18, 2002Publication date: January 9, 2003Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Masanobu Yamase, Yoshiaki Suzuki, Takayuki Moritou
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Patent number: 6479708Abstract: A process is provided for catalyzing an organic reaction to form a reaction product by placing reactants and a catalyst for the organic reaction, the catalyst of a metal complex and at least one ligand soluble within one of the phases of said aqueous biphasic system, within an aqueous biphasic system including a water phase, a dense phase fluid, and a surfactant adapted for forming an emulsion or microemulsion within the aqueous biphasic system, the reactants soluble within one of the phases of the aqueous biphasic system and convertible in the presence of the catalyst to a product having low solubility in the phase in which the catalyst is soluble; and, maintaining the aqueous biphasic system under pressures, at temperatures, and for a period of time sufficient for the organic reaction to occur and form the reaction product and to maintain sufficient density on the dense phase fluid, the reaction product characterized as having low solubility in the phase in which the catalyst is soluble.Type: GrantFiled: November 18, 1999Date of Patent: November 12, 2002Assignee: The Regents of the University of CaliforniaInventors: Gunilla B. Jacobson, William Tumas, Keith P. Johnston
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Process for the cleavage of alkyl tert-alkyl ethers into isoolefins and alkanols over acid catalysts
Publication number: 20020010379Abstract: Alkyl tert-alkyl ethers are cleaved into the corresponding isoolefins and alkanols by a process comprising acid-catalyzed reactive distilling an alkyl tert-alkyl ether fed into the reaction zone of a reactive distillation apparatus as an azeotrope of the alkyl tert-alkyl ether and the corresponding alkanol, wherein the reactive distillation apparatus is configured from bottom to top as a bottom zone, at least one distillation zone and a reaction zone.Type: ApplicationFiled: April 25, 2001Publication date: January 24, 2002Applicant: OXENO Olefinchemie GmbHInventors: Michael Sakuth, Axel Tuchlenski, Dieter Reusch, Andreas Beckmann -
Patent number: 6184424Abstract: A process for the hydrogenation of reaction mixtures from the hydroformylation of C5 to C24 olefins using hydrogen on fixed catalysts at elevated temperature, in which the aldehydes, alcohols, formates and low-boilers are evaporated from the reaction mixture and passed in the vapor state over a support-free Cu/Cr catalyst.Type: GrantFiled: September 15, 1999Date of Patent: February 6, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Wilfried Bueschken, Dietmar Gubisch
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Patent number: 6103943Abstract: Disclosed is a process for the synthesis of 3-buten-1-ol by contacting 3,4-epoxy-1-butene and formic acid with a homogeneous catalyst solution comprising a palladium(0) compound, a tertiary phosphine and a trialkylamine dissolved in tetrahydrofuran.Type: GrantFiled: January 20, 1998Date of Patent: August 15, 2000Assignee: Eastman Chemical CompanyInventor: Charles Allan McCombs
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Patent number: 5569789Abstract: A multistaged fixed catalyst bed process for the production of diisopropyl ether and isopropanol is disclosed comprising a fixed bed of serially connected stages containing zeolite Beta catalyst. A feedstream of propylene and water equivalents selected from the group consisting of water, isopropanol and diisopropyl ether is introduced into each stage at a rate sufficient to provide a mole ratio of water equivalents to propylene equivalents that increases in increments by stage from at least 0.1 in a first stage to at most 1.2 in a final stage. The feedstream is introduced at a temperature between 50.degree. and 450.degree. C., pressure between 700 and 24000 kPa, and weight hourly space velocity between 0.10 and 30, based on catalyst, whereby a single non-aqueous liquid phase is maintained in the fixed bed. An effluent product stream is recovered comprising diisopropyl ether, isopropanol and water from the final stage. Isopropanol is recycled to the first stage when the preferred product is diisopropyl ether.Type: GrantFiled: August 2, 1995Date of Patent: October 29, 1996Assignee: Mobil Oil CorporationInventors: Weldon K. Bell, Stephen H. Brown, Jeffrey C. Trewella
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Patent number: 5406007Abstract: Disclosed is a process for the conversion of conjugated epoxyalkenes to unsaturated alcohols wherein a conjugated epoxyalkene is catalytically hydrogenated in the presence of a sulfur-modified or sulfided nickel catalyst whereby the epoxide ring is hydrogenolyzed without concomitant hydrogenation of the olefinic unsaturation thereby producing allylic and/or homoallylic alcohols.Type: GrantFiled: July 15, 1994Date of Patent: April 11, 1995Assignee: Eastman Chemical CompanyInventor: Stephen N. Falling
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Patent number: 5403964Abstract: The present invention relates to enhanced process for converting certain ethers, such as sec-butyl ether and isopropyl ether to their corresponding reaction products in the presence of water. This may be accomplished by adding a rate enhancing surfactant, such as an anionic or cationic surfactant to a mixture of the ether and water, preferably least about 10.sup.-5 molar surfactant. Under those conditions the reaction shows an increase in reaction rate over the rate of the process wherein surfactant is not used.Type: GrantFiled: January 27, 1994Date of Patent: April 4, 1995Assignee: Exxon Research & Engineering Co.Inventors: Ramzi Y. Saleh, Joel R. Livingston, Jr., Michael Siskin, Glen B. Brons
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Patent number: 5401888Abstract: The present invention provides a method for preparing allylic alcohols by the palladium-catalyzed cross-coupling of vinylic epoxides and aryl halides, vinylic halides or vinylic triflates.Type: GrantFiled: February 9, 1993Date of Patent: March 28, 1995Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 5399788Abstract: In process for the production of diisopropyl ether, a propylene-containing stream is contacted with isopropyl alcohol in a first stage in the presence of a catalyst under conditions to produce an effluent stream comprising diisopropyl ether. At least a portion of this effluent stream is recycled to a second stage where the diisopropyl ether is reacted with water to produce isopropyl alcohol. The isopropyl alcohol is then recycled to the first stage. The benefit of producing isopropyl alcohol by the hydration of diisopropyl ether is that it is an easier reaction than, for example, the hydration of propylene. As a result, the process of the present invention can operate under less severe conditions, i.e., less cost.Type: GrantFiled: December 22, 1993Date of Patent: March 21, 1995Assignee: UOPInventor: Terry L. Marker
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Patent number: 5391773Abstract: Disclosed is a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycycloalkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and .gamma.,.delta.-epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.Type: GrantFiled: June 17, 1994Date of Patent: February 21, 1995Assignee: Eastman Chemical CompanyInventor: Thomas A. Puckette
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Patent number: 5210337Abstract: Rhenium has been found to be formaldehyde resistant catalyst and is thus useful in the catalytic hydrogenation of carbonyls, acetals and esters to alcohols when the reaction medium contains formaldehyde as a reactant or impurity. Also, rhenium is a useful catalyst in the hydrogenolysis of acylic acetals to alcohols.Type: GrantFiled: March 28, 1990Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventor: Jerry A. Broussard
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Patent number: 5116916Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.Type: GrantFiled: January 29, 1988Date of Patent: May 26, 1992Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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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
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Patent number: 5043486Abstract: The present invention provides for a simplified process for converting ethers into their corresponding alcohols comprising forming an aqueous mixture of the ether and at least about 50% by weight water and heating the mixture under autogeneous pressure at a temperature of from about 250.degree. to 450.degree. C., more preferably from about 250.degree. C. up to the critical temperature of water which is about 374.degree. C. Heating is continued for a period of time sufficient to convert at least about 20% by weight of the ether, usually from about 5 up to about 120 minutes, depending on temperature and the amount of water present, and the identity of the starting ether feedstock.The process may be characterized as an aquathermolysis reaction wherein the reaction proceeds in water primarily through ionic routes rather than through free radical routes.Type: GrantFiled: August 23, 1990Date of Patent: August 27, 1991Assignee: Exxon Research and Engineering CompanyInventors: Michael Siskin, Glen B. Brons, Ramzi Y. Saleh, Stephen N. Vaughn
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Patent number: 4958033Abstract: A process for preparing an alcohol of the formula: ##STR1## by reacting a carbonyl compound of the formula: ##STR2## or an oxirane of the formula: ##STR3## magnesium and a propargyl halide of the formula: ##STR4## followed by hydrolysis, characterized in that the carbonyl compound (II) or the oxirane compound (III) and the propargyl halide (IV) are reacted simultaneously with magnesium in an inert solvent in the presence of zinc or a halide thereof.Type: GrantFiled: September 26, 1986Date of Patent: September 18, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
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Patent number: 4904820Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as 1,4-conjugate addition. The complex is formed by reacting a first cuprate cmoplex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes prepared by this process are particularly useful for the efficient preparation of pharmacologically active prostaglandins.Type: GrantFiled: July 14, 1988Date of Patent: February 27, 1990Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling
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Patent number: 4714788Abstract: In a process for separating C.sup.4 to C.sup.7 tertiary mono-olefins(s) present in a C.sup.4 to C.sup.7 hydrocarbon mixture containing diolefins which comprises selectively reacting said tertiary mono-olefin mixture with a primary alcohol in the presence of an acid catalyst to convert it to tertiary ether(s), separating the tertiary ether(s) from the unreacted hydrocarbon mixture and containing said tertiary ether(s) in the presence of a catalyst to decompose it to tertiary olefin(s) and a primary alcohol, the improvement which comprises hydrogenating the tertiary ether(s) after it has been separated from the unreacted hydrocarbon mixture and prior to decomposition to saturate the unsaturated ether(s) formed from the diolefins present in the hydrocarbon mixture.Type: GrantFiled: July 14, 1986Date of Patent: December 22, 1987Assignee: Exxon Chemical Patents Inc.Inventors: Robert C. Michaelson, Jeffrey S. Plotkin
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Patent number: 4661643Abstract: This invention relates to a process for selectively cleaving a polyalkylene glycol, e.g., diethylene glycol, containing at least one ether group therein at a carbon-to-oxygen covalent bond and independently at a carbon-to-carbon covalent bond by heating the polyalkylene glycol with molecular hydrogen in the presence of a hydrogenation catalyst containing ruthenium to produce at least one of monoethylene glycol monomethyl ether, monoethylene glycol and ethanol. The production rate of each of said monoethylene glycol monomethyl ether, monoethylene glycol and ethanol is at least about 10 moles/kilogram ruthenium/hour.Type: GrantFiled: May 21, 1985Date of Patent: April 28, 1987Assignee: Union Carbide CorporationInventor: William J. Bartley
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Patent number: 4649225Abstract: This invention relates to a process for selectively cleaving a polyalkylene glycol, e.g., diethylene glycol, containing at least one ether group therein at a carbon-to-oxygen covalent bond and independently at a carbon-to-carbon covalent bond by heating the polyalkylene glycol with molecular hydrogen in the presence of a hydrogenation catalyst containing iridium to produce at least one of monoethylene glycol monoethyl ether, monoethylene glycol monomethyl ether, monoethylene glycol and ethanol. Monoethylene glycol monoethyl ether can be produced in significant amounts by employing the process of this invention.Type: GrantFiled: May 21, 1985Date of Patent: March 10, 1987Assignee: Union Carbide CorporationInventor: William J. Bartley
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Patent number: 4625050Abstract: A process for the conversion of dialkyl ethers to homologous carboxylic acid esters and alcohols which comprises reacting a dialkyl ether having from two to about twenty carbon atoms with hydrogen and carbon monoxide in the presence of a heterogeneous sulfided catalyst comprising nickel, optionally in admixture with a co-catalyst selected from the elements of Group VI-B of the Periodic Table.Type: GrantFiled: June 23, 1983Date of Patent: November 25, 1986Assignee: Chevron Research CompanyInventor: Steven P. Current