Having Unsaturated Ring Patents (Class 585/318)
  • Patent number: 9771308
    Abstract: Olefins and diolefins, such as 1,3-butiadiene, may be produced by a method utilizing a series of bromination and dehydrobromination reactions. Bromine may be reacted with n-butane to form dibromobutane. The dibromobutanes may be dehydrobrominating to form 1,3-butadiene. The method may include reacting butene with bromine to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with hydrogen bromide in the presence of oxygen to form bromobutenes, and dehydrobrominating the bromobutenes to form 1,3-butadiene. The method may include reacting butene with bromine to form dibromobutanes, and dehydrobrominating the dibromobutanes to form 1,3-butadiene.
    Type: Grant
    Filed: June 9, 2015
    Date of Patent: September 26, 2017
    Assignee: REACTION 35, LLC
    Inventors: Peter K. Stoimenov, Jeffrey H. Sherman
  • Patent number: 9045385
    Abstract: A process is disclosed that includes brominating a C2, C3, C4, C5 or C6 alkane with elemental bromine to form a bromo-alkane. The bromo-alkane is reacted to form a C2, C3, C4, C5 or C6 alkene and HBr. The HBr is oxidized to form elemental bromine.
    Type: Grant
    Filed: December 12, 2014
    Date of Patent: June 2, 2015
    Assignee: REACTION 35, LLC
    Inventors: Vivek Julka, Sagar Gadewar, Peter K. Stoimenov, Philip Grosso, Jeffrey H. Sherman, Aihua Zhang, Eric W. McFarland
  • Publication number: 20150141715
    Abstract: A process for making a bio-naphtha and optionally bio-propane from a complex mixture of natural occurring fats & oils, wherein said complex mixture is subjected to a refining treatment for removing the major part of non-triglyceride and non-fatty acid components, thereby obtaining refined fats & oils; said refined fats & oils are transformed into linear or substantially linear paraffin's as the bio-naphtha by an hydrodeoxygenation or from said refined fats & oils are obtained fatty acids that are transformed into linear or substantially linear paraffin's as the bio-naphtha by hydrodeoxygenation or decarboxylation of the free fatty acids or from said refined fats & oils are obtained fatty acids soaps that are transformed into linear or substantially linear paraffin's as the bio-naphtha by decarboxylation of the soaps.
    Type: Application
    Filed: January 28, 2015
    Publication date: May 21, 2015
    Inventors: Walter Vermeiren, Nicolas Van Gyseghem
  • Publication number: 20150099901
    Abstract: Provided is a method for efficiently producing high-purity hydrogenated biphenol based on a simple method that can be industrially utilized using easily-available biphenol as a starting material. The method for producing hydrogenated biphenol according to the present invention is a method for producing hydrogenated biphenol by hydrogenating biphenol represented by the following formula (1): to obtain hydrogenated biphenol represented by the following formula (2): the method comprising: a reaction step of hydrogenating the biphenol represented by formula (1); and a purification step of washing or crystallizing a reaction product obtained from the reaction step using an aromatic hydrocarbon.
    Type: Application
    Filed: March 28, 2013
    Publication date: April 9, 2015
    Applicant: DAICEL CORPORATION
    Inventors: Mitsuru Ohno, Tomohiro Hashizume
  • Patent number: 8802905
    Abstract: A unique, integrated non-obvious pathway to convert biomass to biofuels using integration of chemical processes is described herein. The present invention is simple, direct, and provides for the shortest or minimum path between biomass and transportation fuels with alcohols as intermediates, while avoiding hydrogen use during processing. Furthermore, the present invention allows the manufacture of “drop-in” substitutable fuels to be used as-is without modifications instead of conventional petroleum based fuels. The processing described herein is done under mild conditions, under relatively low pressures and temperatures, and under non-corrosive conditions obviating use of special equipment or materials.
    Type: Grant
    Filed: June 18, 2010
    Date of Patent: August 12, 2014
    Assignees: The Texas A&M University System, Byogy Renewables, Inc.
    Inventors: Mahmoud M. El-Halwagi, Kenneth R. Hall, Harold Dennis Spriggs
  • Patent number: 8802907
    Abstract: A processes for producing a dehydrogenation reaction product stream comprising the step of contacting a hydrocarbon stream comprising cyclohexane and methyl cyclopentane with a dehydrogenation catalyst comprising at least one metal or compound thereof and at least one molecular sieve and under conditions effective to convert at least a portion of the cyclohexane to benzene and to convert at least a portion of the methyl cyclopentane to at least one paraffin. The hydrocarbon stream is produced by hydroalkylating benzene and hydrogen to form a hydroalkylation reaction product stream which is separated to yield the hydrocarbon stream.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: August 12, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Edward A. Lemon, Jr., Tan-Jen Chen, Terry E. Helton
  • Publication number: 20140179966
    Abstract: Provided is a method for producing a high-carbon number saturated hydrocarbon compound by subjecting a mixed biomass solution containing benzyl phenyl ether (C6H5CH2OC6H5) to a two-step reaction process using a difunctional catalyst having an acid catalyst combined with a metal catalyst. The method allows development of a fuel substituting for and supplementing petroleum through decomposition and conversion of a biomass containing lignin or the like, thereby providing a non-petroleum based biofuel.
    Type: Application
    Filed: April 17, 2013
    Publication date: June 26, 2014
    Applicant: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY
    Inventors: Jeong-Myeong HA, Jae Wook CHOI, Dong Jin SUH, Young Hyun YOON, Ji Sun YOON, Gi Seok YANG
  • Patent number: 8686206
    Abstract: Synthetic fuels are produced from synthesis gas in a four-stage reactor system with a single recycle loop providing the requisite thermal capacity to moderate the high heat release of the reactions and to provide the reactants and reaction environments for the efficient operation of the process. The first stage converts a portion of the synthesis gas to methanol, the second stage converts the methanol to dimethylether, the third stage converts the methanol and dimethylether to fuel and the fourth stage converts the high melting point component, durene, and other low volatility aromatic components such as tri- and tetra-methylbenzenes to high octane branched paraffins.
    Type: Grant
    Filed: November 9, 2010
    Date of Patent: April 1, 2014
    Assignee: Primus Green Energy Inc.
    Inventors: Howard L. Fang, Moshe Ben-Reuven, Richard E. Boyle, Robert M. Koros
  • Publication number: 20140051872
    Abstract: The present invention provides catalysts, methods, and reactor systems for converting oxygenated hydrocarbons to oxygenated compounds. The invention includes methods for producing cyclic ethers, monooxygenates, dioxygenates, ketones, aldehydes, carboxylic acids, and alcohols from oxygenated hydrocarbons, such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like, using catalysts containing palladium, molybdenum, tin, and tungsten. The oxygenated compounds produced are useful in the production of liquid fuels, chemicals, and other products.
    Type: Application
    Filed: August 15, 2012
    Publication date: February 20, 2014
    Applicant: Virent, Inc.
    Inventors: Brian Blank, Randy Cortright, Taylor Beck, Elizabeth Woods, Mike Jehring
  • Publication number: 20140018588
    Abstract: The present invention relates to a process for isomerizing at least one hydrocarbon in the presence of an acidic ionic liquid and at least one hydrogen halide (HX) in an apparatus (V1), wherein the hydrogen halide (HX) is removed in an apparatus (V2) in gaseous form from the isomerization product and is at least partly recycled into apparatus (V1).
    Type: Application
    Filed: July 9, 2013
    Publication date: January 16, 2014
    Inventors: Katharina Spuhl, Markus Schmitt, Jochen Bürkle, Joni Joni, Steffen Tschrischwitz, Daniel Pfeiffer, Steffen Bitterlich, Lukas Schulz, Michael Hübner
  • Publication number: 20130324688
    Abstract: The preparation of cyclohexadienes from one or more plant oils is disclosed. The cyclohexadiene can be used to form polymers or derivatized to form other monomers that can be used to form polymeric materials.
    Type: Application
    Filed: April 9, 2013
    Publication date: December 5, 2013
    Inventor: Robert T. MATHERS
  • Publication number: 20130237732
    Abstract: A method of making para-xylene or toluene is carried out by: (a) reacting a C5 or C6 linear monoene (itself, or formed from a C5 or C6 linear alkane) with a hydrogen acceptor in the presence of a hydrogen transfer catalyst to produce a C5 or C6 diene; (b) reacting the C5-C6 diene with ethylene to produce a cyclohexene having 1 or 2 methyl groups substituted thereon; and then (c) either (i) dehydrogenating the cyclohexene in the presence of a hydrogen acceptor with a hydrogen transfer catalyst to produce a compound selected from the group consisting of para-xylene and toluene, or (ii) dehydrogenating the cyclohexene in the absence of a hydrogen acceptor with a dehydrogenation catalyst, to produce para-xylene or toluene.
    Type: Application
    Filed: May 2, 2013
    Publication date: September 12, 2013
    Applicant: The University of North Carolina at Chapel Hill
    Inventors: Maurice Brookhart, Michael Findlater, Damien Guironnet, Thomas Warren Lyons
  • Publication number: 20130172635
    Abstract: A polyoctenamer is described which at room temperature is liquid, colourless and clear, and which is produced by ring-opening, metathesis polymerization of cyclooctene.
    Type: Application
    Filed: May 26, 2011
    Publication date: July 4, 2013
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Peter Hannen, Norbert Wilczok, Manfred Thiery, Martin Roos
  • Patent number: 8409303
    Abstract: In the processes for treating municipal sewage and storm water containing biosolids to discharge standards, biosolids, even after dewatering, contain typically about 80% water bound in the dead cells of the biosolids, which gives biosolids a negative heating value. It can be incinerated only at the expense of purchased fuel. Biosolids are heated to a temperature at which their cell structure is destroyed and, preferably, at which carbon dioxide is split off to lower the oxygen content of the biosolids. The resulting char is not hydrophilic, and it can be efficiently dewatered and/or dried and is a viable renewable fuel. This renewable fuel can be supplemented by also charging conventional biomass (yard and crop waste, etc.) in the same or in parallel facilities. Similarly, non-renewable hydrophilic fuels can be so processed in conjunction with the processing of biosolids to further augment the energy supply.
    Type: Grant
    Filed: February 11, 2011
    Date of Patent: April 2, 2013
    Assignee: SGC Advisors, LLC
    Inventors: Norman L. Dickinson, Kevin M. Bolin, Edward Overstreet, Brian Dooley
  • Publication number: 20130066124
    Abstract: The present invention relates to a simple and economic method of extracting a crystalline Carotenoid compound, such as Beta-carotene, Lycopene, with a purity of at least 99%. The present invention further describes a process to prepare such a highly pure crystalline Carotenoid compound from microbial biomass, using an Anti-purity compound removal process followed by a mono-solvent extraction method. Further the process describes value addition of the co-products recovered during the extraction process thus resulting in a highly economical industrial method for the production of such high purity crystalline Carotenoids compound.
    Type: Application
    Filed: May 16, 2011
    Publication date: March 14, 2013
    Inventors: Suresh Joseph, Arnaud Anandane
  • Patent number: 8168842
    Abstract: Process for the alkylation of a cycloalkene, which process comprises alkylating a cycloalkene with an oxygenate under alkylating conditions in the presence of a zeolite; to yield an alkylated cycloalkene. Composition obtainable by such a process and use of such a composition as a gasoline blending component.
    Type: Grant
    Filed: May 16, 2007
    Date of Patent: May 1, 2012
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Aden Murphy, Michiel Johannes Franciscus Maria Verhaak, Jeroen Van Westrenen
  • Publication number: 20120095272
    Abstract: A unique, integrated non-obvious pathway to convert biomass to biofuels using integration of chemical processes is described herein. The present invention is simple, direct, and provides for the shortest or minimum path between biomass and transportation fuels with alcohols as intermediates, while avoiding hydrogen use during processing. Furthermore, the present invention allows the manufacture of “drop-in” substitutable fuels to be used as-is without modifications instead of conventional petroleum based fuels. The processing described herein is done under mild conditions, under relatively low pressures and temperatures, and under non-corrosive conditions obviating use of special equipment or materials.
    Type: Application
    Filed: June 18, 2010
    Publication date: April 19, 2012
    Applicant: THE TEXAS A&M UNIVERSITY SYSTEM
    Inventors: Mahmoud M. El-Halwagi, Kenneth R. Hall, Harold Dennis Spriggs
  • Publication number: 20110245543
    Abstract: Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to hydrocarbons, ketones and alcohols useful as liquid fuels, such as gasoline, jet fuel or diesel fuel, and industrial chemicals. The process involves the conversion of mono-oxygenated hydrocarbons, such as alcohols, ketones, aldehydes, furans, carboxylic acids, diols, triols, and/or other polyols, to C4+ hydrocarbons, alcohols and/or ketones, by condensation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.
    Type: Application
    Filed: June 17, 2011
    Publication date: October 6, 2011
    Applicant: Virent Energy Systems, Inc.
    Inventors: Randy D. Cortright, Paul G. Blommel
  • Publication number: 20110178349
    Abstract: A method of treating a hydrocarbon stream comprising cyclopentadiene (CPD) and one or more diolefins, the method comprising: providing a hydrocarbon stream comprising an initial CPD concentration, an initial target diolefin concentration, and an initial secondary diolefin concentration; subjecting the hydrocarbon stream to preseparation conditions effective to separate (a) a crude target diolefin feedstock having a decreased concentration of CPD and an increased target diolefin concentration, and (b) a CPD dimerization feedstock having a decreased target diolefin concentration and an increased CPD concentration that is 1.5 or more times the initial CPD concentration; subjecting the CPD dimerization feedstock to CPD dimerization conditions effective to produce a raw DCPD stream comprising 20 wt. % or more DCPD; and, separating a high purity DCPD product stream comprising 90 wt. % or more DCPD from the raw DCPD stream.
    Type: Application
    Filed: December 15, 2010
    Publication date: July 21, 2011
    Inventors: Robert Kenneth ANZICK, Robert Lawrence BLACKBOURN, SivaKumar NAYARAJAN
  • 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
  • Patent number: 7579511
    Abstract: Provided is a process for making cyclohexylbenzene.
    Type: Grant
    Filed: October 10, 2008
    Date of Patent: August 25, 2009
    Assignee: Exxonmobil Research and Engineering Company
    Inventors: Jihad Mohammed Dakka, Lorenzo Cophard DeCaul, Teng Xu
  • Patent number: 7411101
    Abstract: A process for producing a monoalkylation aromatic product, such as ethylbenzene and cumene, utilizing an alkylation reactor zone and a transalkylation zone in series or a combined alkylation and transkylation reactor zone.
    Type: Grant
    Filed: February 6, 2002
    Date of Patent: August 12, 2008
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Shiou-Shan Chen, Henry Hwang
  • Patent number: 7161050
    Abstract: A reactant selected from the group consisting of alkanes, alkenes, alkynes, dienes, and aromatics is reacted with a halide selected from the group including chlorine, bromine, and iodine to form a first reaction product. The first reaction product is reacted with a solid oxidizer to form a product selected from the group including olefins, alcohols, ethers, and aldehydes, and spent oxidizer. The spent oxidizer is oxidized to form the original solid oxidizer and the second reactant which are recycled.
    Type: Grant
    Filed: August 19, 2003
    Date of Patent: January 9, 2007
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Jeffrey H. Sherman, Eric W. McFarland, Michael J. Weiss, Ivan Marc Lorkovic, Leroy E. Laverman, Shouli Sun, Dieter J. Schaefer, Galen Stucky, Peter Ford
  • Patent number: 7148390
    Abstract: Alcohols, ethers, aldehydes, and olefins are manufactured from alkanes by mixing an alkane and a halogen selected from the group including chlorine, bromine, and iodine in a reactor to form alkyl halide and hydrogen halide. The alkyl halide only or the alkyl halide and the hydrogen halide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal halide. The metal halide is oxidized to form original metal oxide and halogen, both of which are recycled.
    Type: Grant
    Filed: February 27, 2003
    Date of Patent: December 12, 2006
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Jeffrey H. Sherman
  • Patent number: 6790342
    Abstract: Processes are provided to produce a dilute ethylene stream and a dilute propylene stream from a cracked gas stream. One process comprises separating the cracked gas stream to produce a C3− stream and a C3+ stream; hydrogenating the C2− stream in a hydrogenation zone to remove a portion of the acetylene to produce the dilute ethylene stream and routing the C3+ stream to storage or other process unit. Another process comprises separating a cracked gas stream in a depropanizer zone to form a C3− stream and a C4+ stream; separating the C3− stream in a deethanizer zone to form a C2− and a C3 stream; hydrogenating a portion of the acetylene in the C2− stream in a hydrogenation zone to produce a dilute ethylene stream; and routing the C3 stream to storage or other process unit.
    Type: Grant
    Filed: February 27, 2002
    Date of Patent: September 14, 2004
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Rodney L. Porter, Anne M. Balinsky, Eric P. Weber
  • Patent number: 6783659
    Abstract: A process is provided to produce a dilute ethylene stream and a dilute propylene stream to be used as feedstocks for producing olefin-based derivatives. Specifically, the dilute ethylene stream is used as a feedstock to produce ethylbenzene, and the dilute propylene stream is used as a feedstock to produce cumene, acrylic acid, propylene oxide and other propylene based derivatives.
    Type: Grant
    Filed: November 16, 2001
    Date of Patent: August 31, 2004
    Assignee: Chevron Phillips Chemical Company, L.P.
    Inventors: Rodney L. Porter, Anne M. Balinsky, Eric P. Weber
  • Publication number: 20030171630
    Abstract: A unified process for reactive distillation under pressure for the alkylation of light aromatic hydrocarbons such as benzene and cumene with straight chain C6-C18 olefins using a solid acid alkylation catalyst supported in the reflux zone of the distillation column. The process is continuous, using a reactive distillation configuration such that at least a portion of the olefin is injected below the benzene rectification zone at the top of the column. The aromatic hydrocarbon is injected continuously at a low rate above the rectification zone at the base of the column and above the reboiler. The alkylation reaction takes place primarily in the liquid phase on the solid acid catalyst and is characterized in that the molar ratio of aromatic hydrocarbon to olefin in the liquid phase may be adjusted.
    Type: Application
    Filed: March 5, 2002
    Publication date: September 11, 2003
    Inventors: J. Barry Winder, Donald L. Wharry, John R. Schell, Mary J. Brown, Joy L. Murray, Richard C. Howe, Wayne L. Sorensen, Daniel P. Szura
  • Patent number: 6579419
    Abstract: For the purification of the norbornene obtained by the reaction of dicyclopentadiene or cyclopentadiene and ethylene, the crude reaction mixture containing light impurities having boiling temperatures lower than that of norbornene; medium-heavy impurities having the boiling temperatures between that of norbornene and that of ethylnorbornene; and heavy impurities containing ethylnorbornene and compounds boiling higher than ethylnorbornene, boiling temperatures greater than that ethylnorbornene, a first distillation of the crude reaction mixture is carried out in a tailing column (C1), removing a portion of the heavy impurities and a portion of the medium-heavy impurities; then a second distillation of the crude mixture, thus tailed, is carried out in a topping column (C2), removing the light impurities; and a third distillation of the mixture, thus topped, is subsequently carried out in a tailing column (C3), removing the remainder of the heavy and medium-heavy impurities.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: June 17, 2003
    Assignee: Elf Atochem, S.A.
    Inventors: Roland Kotwica, André Marbach
  • Patent number: 6479719
    Abstract: This process for the manufacture of norbornene from dicyclopentadiene (DCPD) and ethylene is characterized in that the DCPD is subjected to partial monomerization to CPD by preheating: at a temperature of 140° C. to 240° C.; and under a pressure of 20 to 300 bar abs., before reacting it with the ethylene; with an ethylene/DCPD molar ratio of 1 to 20; at a temperature of 200° C. to 320° C.; under a pressure of 20 to 300 bar abs.; and with a residence time of 1 to 10 minutes, under stable reaction conditions between the DCPD, the CPD and the ethylene.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: November 12, 2002
    Assignee: Atofina
    Inventors: Roland Kotwica, André Marbach
  • Patent number: 6444867
    Abstract: Linear alpha olefins are typically produced by starting with a trialkylaluminum compound, such as triethylaluminum, and then subjecting the trialkylaluminum compound to alkyl chain growth conditions in the presence of ethylene and elevated temperature and pressure, frequently in the presence of a chain growth catalyst. Under such alkyl chain growth conditions, the alkyl groups attached to the aluminum may be extended by two carbon atoms per reaction with ethylene. The process is permitted to continue until the alkyl groups have reached the desired length at which point they are displaced from the trialkylaluminum compund as alpha olefins, usually in the presence of an excess of ethylene and a displacement catalyst. This invention discloses a new chain growth catalyst system comprising, in combination, non-bridged metallocenes and aluminum complexes having amidinate ligands and inert anions.
    Type: Grant
    Filed: May 17, 2001
    Date of Patent: September 3, 2002
    Assignee: BP Corporation North America Inc.
    Inventors: Edward G. Samsel, Franke N. Brooks
  • Patent number: 6388151
    Abstract: A method for synthesizing tetramethylcyclopentadiene from 2,3-dibromobutane is described. A 2-bromo-2-butene Grignard is reacted with an ethyl formate to produce a 3,5-dimethyl-2,5-heptadiene-4-ol magnesium bromide which is then quenched with acetic acid to produce 3,5-dimethyl-2,5-hepadiene-4-ol.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: May 14, 2002
    Assignee: Boulder Scientific Company
    Inventors: Jeffrey M. Sullivan, Richard D. Crawford
  • Patent number: 6258989
    Abstract: A hydrocarbon feedstock containing C5 olefins, C5 diolefins, CPD, DCPD, and aromatics is processed by the steps of heating a hydrocarbon feedstock containing CPD, DCPD, C5 diolefins, benzene, toluene, and xylene in a heating zone, to dimerize CPD to DCPD, thereby forming a first effluent; separating the first effluent into a C6+ stream and a C5 diolefin stream; separating the C6+ stream into a C6-C9 stream and a C10+ stream; separating the C10+ stream into a fuel oil stream and a DCPD stream; and hydrotreating the C6-C9 stream to thereby form a BTX stream.
    Type: Grant
    Filed: September 30, 1999
    Date of Patent: July 10, 2001
    Assignee: Phillips Petroleum Company
    Inventors: Steven A. Owen, Marvin M. Johnson, Tin-Tack Peter Cheung, Mark E. Lashier
  • Patent number: 6100435
    Abstract: A process is disclosed for converting dicyclopentadiene to cyclopentane and/or cyclopentene, wherein dicyclopentadiene is fed to a catalytic distillation column, the dicyclopentadiene is cracked to cyclopentadiene in the catalytic distillation column, the cyclopentadiene is hydrogenated to cyclopentane in the catalytic distillation column, and the cyclopentane is recovered from the catalytic distillation column. The dicyclopentadiene is fed into and cracked to cyclopentadiene at the bottom of the catalytic distillation column. Hydrogen is then fed to the catalytic distillation column below the catalytic zone, where cyclopentadiene is hydrogenated as it is produced, thus suppressing polymerization of the cyclopentadiene. The resulting cyclopentane and/or cyclopentene vapor phase stream is condensed, thereby producing a liquid stream of cyclopentane and/or cyclopentene and a vapor stream of hydrogen and other off-gas by-products.
    Type: Grant
    Filed: November 13, 1998
    Date of Patent: August 8, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Steven E. Silverberg, Leonel E. Sanchez, James R. Lattner
  • Patent number: 5670681
    Abstract: The present invention relates to a process for preparing a carbon-bridged biscyclopentadiene compound by reacting one or two cyclopentadiene compounds LH with a carbonyl compound in the presence of at least one base and at least one phase transfer catalyst.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: September 23, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Frank Kuber, Michael Riedel
  • Patent number: 5489724
    Abstract: Aliphatic feeds are converted to olefins and/or aromatics in a multi pressure reactor system. A high pressure first stage reactor generates much or all of the hydrogen needed to reduce catalyst coking in lower pressure downstream reactors. High pressure operation protects catalyst stability in the first reactor, while produced hydrogen helps protect downstream catalyst. Low pressure downstream operation improves yields.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: February 6, 1996
    Assignee: Mobil Oil Corporation
    Inventor: Mohsen N. Harandi
  • Patent number: 5401891
    Abstract: A process for purifying crude dicyclopentadiene which comprises the steps of: cracking the crude dicyclopentadiene to form a monomeric-containing effluent which comprises at least one monomer selected from the group consisting of: C.sub.4 acyclic dienes, C.sub.5 acyclic dienes, cyclopentadiene and methylcyclopentadiene; separating the monomeric-containing effluent into a cyclopentadiene-enriched stream and a cyclopentadiene-poor stream; dimerizing the cyclopentadiene-enriched stream to form a dimerizer effluent; contacting a membrane separator under pervaporation conditions with the dimerizer effluent wherein the C.sub.4 acyclic dienes, C.sub.5 acyclic dienes and cyclopentadiene permeate through the membrane separator and wherein a dicyclopentadiene product having a purity of at least about 98% is retained as retentate.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: March 28, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Michael J. Keenan, David W. Sharp, Robert C. Schucker
  • Patent number: 5321177
    Abstract: Recently, as a process for manufacturing cyclopentadiene resin-shaped articles, an attention has been given to reaction injection molding (RIM). To conduct RIM, it is necessary to use high purity dicyclopentadiene (DCPD) as the raw material. Vapor-phase thermal cracking of DCPD is usually used as a step of process for manufacturing high purity DCPD. Hithertofore, when conducting thermal cracking of DCPD, coke formation within cracking tubes is the most serious and troublesome problem. A vapor-phase thermal cracking process for resolving the problem by a very simple procedure is described herein. Further, a process for manufacturing high purity DCPD suitable as a raw material for use in RIM utilizing the vapor-phase thermal cracking process just mentioned above is also described.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: June 14, 1994
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Takao Nakamura, Masaru Kawakita, Katsumi Minomiya
  • Patent number: 5284986
    Abstract: This invention is a process of converting n-pentane to cyclopentene. In accordance with a preferred embodiment n-pentane feed is converted in a dual temperature stage-dual catalyst process without interstage processing of the first-stage product mixture.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: February 8, 1994
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 4985203
    Abstract: Aliphatic oxygenates are converted to high octane gasoline by an integrated reactor system wherein three reaction zones are utilized. In a first reaction zone the oxygenates are directly converted to gasoline and an isobutane by-product. In a second reaction zone oxygenates are dehydrated to an intermediate product comprising C.sub.3 -C.sub.4 olefins, which are then further reacted with the isobutane by-product in a third reaction zone to yield a gasoline alkylate. Ethylene-containing vapors may be separated from the second reaction zone and recycled to the first reaction zone for further processing.
    Type: Grant
    Filed: February 5, 1987
    Date of Patent: January 15, 1991
    Assignee: Mobil Oil Corporation
    Inventor: Samuel A. Tabak
  • Patent number: 4895996
    Abstract: Alkenes are prepared by the hydroboration of enamines followed by an elimination reaction to form the alkene. This process has wide applicability and is useful for the stereospecific synthesis of [Z] isomers. It is preferred to use 9-borabicyclo[3.3.1 nonane as the hydroborating agent and to use methanol to catalyze the elimination reaction.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: January 23, 1990
    Assignees: Purdue Research Foundation, The Dow Chemical Company
    Inventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
  • Patent number: 4886924
    Abstract: A process for the stereospecific synthesis of [E] alkenes from enamines comprising the steps of hydroborating the enamine; esterifying the organoborane so formed and oxidizing the boronic ester in the presence of hydrogen peroxide and in the absence of added base under conditions sufficient to form the [E] alkene in high yield.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: December 12, 1989
    Assignee: The Dow Chemical Company
    Inventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
  • Patent number: 4827045
    Abstract: An improved process for reacting crude aqueous methanol feedstock with iso-olefinic hydrocarbons to produce C.sub.5.sup.+ methyl tertiary-alkly ethers, which comprises: contacting the aqueous methanol feedstock with a liquid hydrocarbon extractant rich in C.sub.4.sup.+ iso-alkene under liquid extraction conditons; recovering an organic extract phase comprising the hydrocarbon extractant and a major amount of methanol introduced in the feedstock; reacting the extracted methanol and C.sub.4.sup.+ isoalkene in contact with an acid etherification catalyst under catalytic reaction conditions to produce ether product; recovering an aqueous methanol raffinate phase containing the major amount of water introduced with the feedstock and a minor amount of feedstock methanol; and converting methanol from the aqueous raffinate phase to produce hydrocarbons.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: May 2, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4393258
    Abstract: A 1-cyclohexyl-2-cyclohexylphenylethane derivative of the following general formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a linear alkyl group having 1 to 7 carbon atoms.
    Type: Grant
    Filed: June 10, 1982
    Date of Patent: July 12, 1983
    Assignee: Dainippon Mk & Chemicals Inc.
    Inventors: Hisato Sato, Haruyoshi Takatsu, Yutaka Fujita, Masayuki Tazume, Kiyohumi Takeuchi, Hiroyuki Ohnishi
  • Patent number: 4367360
    Abstract: A method is disclosed for extracting sym-octahydroanthracene (s-OHA) from a product isomer mixture formed by the aluminum chloride catalyzed isomerization of sym-octahydrophenanthrene (s-OHP). Isolation of the s-OHA product isomer is accomplished by contacting the reaction product mixture with a specified liquid hydrocarbon solvent into which the s-OHA product isomer and unconverted s-OHP isomer dissolve and separate from a residue. The undissolved residue comprises a complex made up of aluminum chloride catalyst and small amounts of the s-OHA and s-OHP isomers. This catalyst complex may be recycled into a fresh starting mixture of s-OHP isomer for catalysis of a subsequent s-OHP isomerization reaction.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: January 4, 1983
    Assignee: Koppers Company, Inc.
    Inventor: William T. Gormley