To Produce Alicyclic Patents (Class 585/317)
  • Patent number: 11203726
    Abstract: A diamondoid fuel comprising a cage structure including 10, 14, 18, or 22 carbons. The diamondoid fuel also includes one of one to four cyclopropyl groups bonded to the cage structure or two to four functional groups bonded to the cage structure where the functional groups are an alkyl group, an allyl group, a cyclopropyl group, or combinations thereof. Additionally, at least one functional group is an allyl group and at least one functional group is a cyclopropyl group.
    Type: Grant
    Filed: March 31, 2020
    Date of Patent: December 21, 2021
    Assignee: The United States of America, as represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Matthew C. Davis
  • Patent number: 11118124
    Abstract: A diamondoid fuel comprising a cage structure including 10, 14, 18, or 22 carbons. The diamondoid fuel also includes one of one to four cyclopropyl groups bonded to the cage structure or two to four functional groups bonded to the cage structure where the functional groups are an alkyl group, an allyl group, a cyclopropyl group, or combinations thereof. Additionally, at least one functional group is an allyl group and at least one functional group is a cyclopropyl group.
    Type: Grant
    Filed: October 7, 2019
    Date of Patent: September 14, 2021
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Matthew C. Davis
  • Patent number: 10865107
    Abstract: The invention provides a process for preparing liquid fuels and chemicals, which process comprises feeding carbon monoxide and hydrogen to a hydrogenation reactor, wherein the molar ratio CO:H2 is in the range of 1:0.5 to 1:0.9, catalytically hydrogenating said carbon monoxide in said hydrogenation reactor, condensing the effluent of said hydrogenation reactor to recover one or more organic liquid(s) and an aqueous solution, feeding a non-condensable component of said effluent into an oligomerization reactor; condensing an effluent discharged from the oligomerization reactor to obtain an additional organic liquid and an additional gaseous stream, separating said additional organic liquid, and either combusting said additional gaseous stream to produce heat and electricity, or processing same to obtain recyclable gaseous streams utilizable in said process.
    Type: Grant
    Filed: September 10, 2017
    Date of Patent: December 15, 2020
    Assignee: B.G. NEGEV TECHNOLOGIES & APPLICATIONS LTD., AT BEN-GURION UNIVERSITY
    Inventors: Mordechay Herskowitz, Tomy Hos
  • Patent number: 10604711
    Abstract: A method for making an alkyl cyclobutane fuel, which includes obtaining a solution of at least one alpha olefin. A catalyst is added to the solution, thereby generating a mixture of dimers. The mixture is hydrogenated, thereby converting the dimers to hydrogenated dimers. The mixture is purified to produce an alkyl cyclobutane fuel.
    Type: Grant
    Filed: August 9, 2018
    Date of Patent: March 31, 2020
    Assignee: The United States of America, as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, David Morris
  • Patent number: 10259758
    Abstract: The present invention relates to an integrated process to convert crude oil into petrochemical products comprising crude oil distillation, aromatic ring opening, and olefins synthesis, which process comprises subjecting a hydrocarbon feed to aromatic ring opening to produce LPG and subjecting the LPG produced in the integrated process to olefins synthesis. Furthermore, the present invention relates to a process installation to convert crude oil into petrochemical products comprising a crude distillation unit comprising an inlet for crude oil and at least one outlet for kerosene and/or gasoil; an aromatic ring opening unit comprising an inlet for a hydrocarbon feed to aromatic ring opening and an outlet for LPG; and a unit for the olefins synthesis comprising an inlet for LPG produced by the integrated petrochemical process installation and an outlet for olefins.
    Type: Grant
    Filed: October 5, 2018
    Date of Patent: April 16, 2019
    Assignees: SAUDI BASIC INDUSTRIES CORPORATION, SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Andrew Mark Ward, Ravichander Narayanaswamy, Vijayanand Rajagopalan, Arno Johannes Maria Oprins, Egidius Jacoba Maria Schaerlaeckens, Raul Velasco Pelaez
  • Patent number: 9873646
    Abstract: The present invention relates to a process for preparing cyclohexane from methylcyclopentane (MCP) and benzene. In the context of the present invention, MCP and benzene are constituents of a hydrocarbon mixture (HM1) additionally comprising dimethylpentanes (DMP), possibly cyclohexane and possibly at least one compound (low boiler) selected from acyclic C5-C6-alkanes and cyclopentane. First of all, benzene is converted in a hydrogenation step to cyclohexane (that present in the hydrocarbon mixture (HM2)), while MCP is isomerized in the presence of a catalyst, preferably of an acidic ionic liquid, to cyclohexane. After the hydrogenation but prior to the isomerization the dimethylpentanes (DMP) are removed, with initial removal of the cyclohexane present in the hydrocarbon mixture (HM2) together with DMP. This cyclohexane already present prior to the isomerization can be separated again from DMP in a downstream rectification step and isolated and/or recycled into the process for cyclohexane preparation.
    Type: Grant
    Filed: April 20, 2015
    Date of Patent: January 23, 2018
    Assignee: BASF SE
    Inventors: Michael Hübner, Lukas Schulz, Pawel Czajka, Oliver Christian Gobin, Nicole Holub, Daniel Pfeiffer, Andreas Weickgenannt, Marta Porta Garcia
  • Patent number: 9839797
    Abstract: A process is provided for the production of linear saturated alkanes from one or more primary alcohols, wherein the carbon chain of the one or more primary alcohols has one carbon atom more than the alkane, including conducting reductive dehydroxymethylation of one or more primary fatty alcohols containing 8 to 24 carbon atoms, at a temperature ranging from 100 to 300° C. and pressures from 1 to 250 bar in the presence of hydrogen and a catalyst, and removing water formed during the reaction.
    Type: Grant
    Filed: December 5, 2006
    Date of Patent: December 12, 2017
    Assignee: Cognis IP Management GmbH
    Inventors: Jürgen Falkowski, Markus Dierker, Michael Neuβ, Karl Heinz Schmid, Stephan Würkert, Lars Zander
  • Patent number: 9650314
    Abstract: A method for producing high density fuels from isoprene which can be produced via biosynthetic routes using biomass sugars as feedstock. This allows for the production of isoprene and isoprene-derived fuels from abundant waste materials with the potential to significantly reduce DoD carbon emissions. Embodiments of the invention describe a method for conversion of isoprene to full performance jet and diesel fuels. Isoprene can be selectively oligomerized to generate a distribution of branched chain hydrocarbons. Combination of an oligomerization catalyst with a metathesis catalyst allows for the synthesis of high density cyclic fuels with performance advantages (increased density and volumetric net heat of combustion) over conventional petroleum-based fuels.
    Type: Grant
    Filed: May 19, 2016
    Date of Patent: May 16, 2017
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventor: Benjamin G. Harvey
  • 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
  • Publication number: 20140171706
    Abstract: Methods and apparatuses for forming low-aromatic high-octane product streams and methods for processing hydrocarbons are provided. In an embodiment, a method for forming a low-aromatic high-octane product stream includes deisohexanizing or deisoheptanizing a hydrocarbon stream and forming a cycloalkane-rich stream. Further, the method includes isomerizing the cycloalkane-rich stream at equilibrium conditions favoring formation of cyclopentanes over cyclohexanes.
    Type: Application
    Filed: December 14, 2012
    Publication date: June 19, 2014
    Applicant: UOP LLC
    Inventor: Bryan K. Glover
  • Publication number: 20140163268
    Abstract: A process for converting triacylglycerides-containing oils into crude oil precursors and/or distillate hydrocarbon fuels is disclosed. The process may include reacting a triacylglycerides-containing oil-carbon dioxide mixture at a temperature in the range from about 250° C. to about 525° C. and a pressure greater than about 75 bar to convert at least a portion of the triacylglycerides to a hydrocarbon or mixture of hydrocarbons comprising one or more of isoolefins, isoparaffins, cycloolefins, cycloparaffins, and aromatics.
    Type: Application
    Filed: December 11, 2012
    Publication date: June 12, 2014
    Applicant: LUMMUS TECHNOLOGY INC.
    Inventor: Marvin I. Greene
  • 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: 20140018587
    Abstract: This invention relates to fuel compositions for use in combustion engines, such as for motor vehicle and aircraft usage. The fuel composition contains at least 99.5% of aromatic hydrocarbons and paraffinic hydrocarbons. The composition also preferably contains no lead, no multi-ring compound (only single ring compounds are present), less than about 15 ppm sulfur, and/or less than about 5 ppm nitrogen species. The resulting fuel is a drop-in fuel that provides clean burning with little to no engine deposit, high lubricity, high stability, and low corrosion.
    Type: Application
    Filed: July 12, 2013
    Publication date: January 16, 2014
    Applicant: Primus Green Energy Inc.
    Inventors: Howard L. FANG, Meifang QIN, Moshe BEN-REUVEN
  • Patent number: 8507396
    Abstract: A process for regenerating a used acidic catalyst which has been deactivated by conjunct polymers by removing the conjunct polymers so as to increase the activity of the catalyst is disclosed. Methods for removing the conjunct polymers include addition of a basic reagent and alkylation. The methods are applicable to all acidic catalysts and are described with reference to certain ionic liquid catalysts.
    Type: Grant
    Filed: April 20, 2010
    Date of Patent: August 13, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Thomas V. Harris
  • Publication number: 20130165720
    Abstract: A new family of coherently grown composites of TUN and IMF zeotypes have been synthesized. These zeolites are represented by the empirical formula. NanMmk+TtAl1-xExSiyOz where “n” is the mole ratio of Na to (Al+E), M represents a metal or metals from zinc, Group 1, Group 2, Group 3 and or the lanthanide series of the periodic table, “m” is the mole ratio of M to (Al+E), “k” is the average charge of the metal or metals M, T is the organic structure directing agent or agents, and E is a framework element such as gallium. These zeolites are similar to TNU-9 and IM-5 but are characterized by unique compositions and synthesis procedures and have catalytic properties for carrying out various hydrocarbon conversion processes and separation properties for carrying out various separations.
    Type: Application
    Filed: December 14, 2012
    Publication date: June 27, 2013
    Applicant: UOP LLC
    Inventor: UOP LLC
  • Publication number: 20130096356
    Abstract: Methods and apparatuses for the isomerization and deisohexanizing of a feed are provided. In a method for the isomerization of a feed in an isomerization zone to form an isomerized stream and the deisohexanizing of the isomerized stream in a deisohexanizer zone, heat is exchanged between the isomerization zone and the deisohexanizer zone to raise the temperature of the feed and to reduce the temperature of the deisohexanizer sidecut stream.
    Type: Application
    Filed: October 14, 2011
    Publication date: April 18, 2013
    Applicant: UOP LLC
    Inventors: Laxmikant V. Bharuka, Heidi C. Fraser, David James Shecterle
  • 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: 20130036660
    Abstract: The present invention provides methods, reactor systems, and catalysts for converting in a continuous process biomass to fuels and chemicals. The invention includes methods of converting the water insoluble components of biomass, such as hemicellulose, cellulose and lignin, to volatile C2+O1-2 oxygenates, such as alcohols, ketones, cyclic ethers, esters, carboxylic acids, aldehydes, and mixtures thereof. In certain applications, the volatile C2+O1-2 oxygenates can be collected and used as a final chemical product, or used in downstream processes to produce liquid fuels, chemicals and other products.
    Type: Application
    Filed: May 23, 2012
    Publication date: February 14, 2013
    Applicant: Virent, Inc.
    Inventors: Elizabeth Woods, Ming Qiao, Paul Myren, Randy D. Cortright, John Kania
  • Publication number: 20130018213
    Abstract: Embodiments of methods for making renewable diesel by deoxygenating (decarboxylating/decarbonylating/dehydrating) fatty acids to produce hydrocarbons are disclosed. Fatty acids are exposed to a catalyst selected from a) Pt and MO3 on ZrO2 (M is W, Mo, or a combination thereof), or b) Pt/Ge or Pt/Sn on carbon, and the catalyst decarboxylates at least 10% of the fatty acids. In particular embodiments, the catalyst consists essentially of 0.7 wt % Pt and 12 wt % WO3, relative to a mass of catalyst, or the catalyst consists essentially of a) 5 wt % Pt and b) 0.5 wt % Ge or 0.5 wt % Sn, relative to a mass of catalyst. Deoxygenation is performed without added hydrogen and at less than 100 psi. Disclosed embodiments of the catalysts deoxygenate at least 10% of fatty acids in a fatty acid feed, and remain capable of deoxygenating fatty acids for at least 200 minutes to more than 350 hours.
    Type: Application
    Filed: September 14, 2012
    Publication date: January 17, 2013
    Inventors: Richard T. Hallen, Karl O. Albrecht, Heather M. Brown, James F. White
  • Publication number: 20120283493
    Abstract: An integrated method for production of fuels, fuel additives, or chemicals in a biorefinery by the conversion of cellulosic materials is disclosed herein. The method is based on converting a source of C6 sugar into a mixture of hydrotreated compounds. Embodiments of the method can be highly integrated, with reagents for particular steps being provided by other steps of the process.
    Type: Application
    Filed: March 7, 2012
    Publication date: November 8, 2012
    Inventors: Edwin S. Olson, Carsten Heide
  • Patent number: 8299310
    Abstract: Processes for conversion of lignin to products such as phenolic compounds and biofuels prepared from such phenolic compounds are disclosed and described. A process for conversion of a lignin material to bio-fuels can include subjecting the lignin material to a base catalyzed depolymerization reaction to produce a partially depolymerized lignin. The partially depolymerized lignin can then be subjected to a stabilization/partial hydrodeoxygenation reaction to form a partially hydrodeoxygenated product. Following partial hydrodeoxygenation, the partially hydrodeoxygenated product can be reacted in a hydroprocessing step to form a bio-fuel. Each of these reaction steps can be performed in single or multiple steps, depending on the design of the process. The production of an intermediate partially hydrodeoxygenation product and subsequent reaction thereof can significantly reduce or eliminate reactor plugging and catalyst coking.
    Type: Grant
    Filed: May 6, 2011
    Date of Patent: October 30, 2012
    Assignee: University of Utah Research Foundation
    Inventors: Wlodzimierz W. Zmierczak, Jan D. Miller
  • Patent number: 8188326
    Abstract: A method for producing adamantane by performing an isomerization reaction in two stages using endo-tetrahydrodicyclopentadiene and/or exo-tetrahydrodicyclopentadiene as a starting material, wherein in a first-stage isomerization reaction from endo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane) to exo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane), an HF catalyst alone or two catalysts of an HF catalyst and a BF3 catalyst are used in the absence of a solvent; and in a second-stage isomerization reaction from exo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane) to adamantane (tricyclo[3.3.1.13,7]decane), an HF catalyst and a BF3 catalyst are used in the absence of a solvent.
    Type: Grant
    Filed: May 7, 2009
    Date of Patent: May 29, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takeshi Kawai, Mitsuharu Kitamura
  • Publication number: 20120116137
    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- andtetra-methylbenzenes to high octane branched paraffins. The four-stage catalyst used for hydrotreating is resistant to CO poisoning. The reactions i produce water as a side product that is carried through to a high pressure separator after the fourth stage.
    Type: Application
    Filed: November 9, 2010
    Publication date: May 10, 2012
    Applicant: PRIMUS GREEN ENERGY INC.
    Inventors: Howard L. Fang, Moshe BEN-REUVEN, Richard E. BOYLE, Robert M. KOROS
  • 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: 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
  • Patent number: 7964761
    Abstract: Processes for conversion of lignin to liquid products such as bio-fuels and fuel additives are disclosed and described. A process for conversion of a lignin material to bio-fuels can include subjecting the lignin material to a base catalyzed depolymerization reaction to produce a partially depolymerized lignin. The partially depolymerized lignin can then be subjected to a stabilization/partial hydrodeoxygenation reaction to form a partially hydrodeoxygenated product. Following partial hydrodeoxygenation, the partially hydrodeoxygenated product can be reacted in a hydroprocessing step to form a bio-fuel. Each of these reaction steps can be performed in single or multiple steps, depending on the design of the process. The production of an intermediate partially hydrodeoxygenation product and subsequent reaction thereof can significantly reduce or eliminate reactor plugging and catalyst coking.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: June 21, 2011
    Assignee: University of Utah Research Foundation
    Inventors: Wlodzimierz W. Zmierczak, Jan D. Miller
  • Publication number: 20110112346
    Abstract: A method for producing adamantane by performing an isomerization reaction in two stages using endo-tetrahydrodicyclopentadiene and/or exo-tetrahydrodicyclopentadiene as a starting material, wherein in a first-stage isomerization reaction from endo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane) to exo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane), an HF catalyst alone or two catalysts of an HF catalyst and a BF3 catalyst are used in the absence of a solvent; and in a second-stage isomerization reaction from exo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane) to adamantane (tricyclo[3.3.1.13,7]decane), an HF catalyst and a BF3 catalyst are used in the absence of a solvent.
    Type: Application
    Filed: May 7, 2009
    Publication date: May 12, 2011
    Inventors: Takeshi Kawai, Mitsuharu Kitamura
  • Publication number: 20110105811
    Abstract: A process to produce an alkylate distillate blending component in one embodiment comprising: providing at least one olefinic C5+ product which was produced by conversion of synthesis gas in a Fischer Tropsch process; and alkylating the olefinic C5+ product in the presence of an acidic ionic liquid alkylation catalyst with hydrocarbons selected from the group consisting of isoparaffins, cycloparaffins, and their mixtures to form an alkylate distillate blending component is described.
    Type: Application
    Filed: October 30, 2009
    Publication date: May 5, 2011
    Inventors: Dennis J. O'Rear, Sven Ivar Hommeltoft, Steve S. Mathur, Jerome F. Mayor, Hye-Kyung Timken
  • Publication number: 20110105814
    Abstract: The invention relates to a process for producing a new type of high-quality hydrocarbon base oil of biological origin. The process of the invention comprises ketonisation, hydrodeoxygenation, and isomerization steps. Fatty acids and/or fatty acid esters based on a biological raw material are preferably used as the feedstock.
    Type: Application
    Filed: November 24, 2010
    Publication date: May 5, 2011
    Applicant: Neste Oil Oyj
    Inventors: Eija KOIVUSALMI, Johan-Fredrik Selin, Juha Moilanen
  • Patent number: 7803265
    Abstract: A process is disclosed for converting distillate to gasoline-range hydrocarbons using a two-stage catalyst system including a first catalyst containing platinum, palladium, or platinum and palladium, and an acidic support, and a second catalyst containing iridium and an inorganic oxide support, and optionally nickel.
    Type: Grant
    Filed: February 4, 2009
    Date of Patent: September 28, 2010
    Assignee: ConocoPhillips Company
    Inventors: Tushar V. Choudhary, Paul F. Meier, Edward L. Sughrue, II, Walter E. Alvarez
  • Publication number: 20100191008
    Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.
    Type: Application
    Filed: January 29, 2009
    Publication date: July 29, 2010
    Applicant: ENERGY & ENVIRONMENTAL RESEARCH CENTER FOUNDATION
    Inventor: Edwin S. Olson
  • Patent number: 7744742
    Abstract: The process as described herein produces a moderately aromatic isoparaffinic base oil from a distillate range product. This process comprises: (a) providing a distillate range paraffin feed comprising paraffins and cycloparaffins; (b) mildly reforming the distillate range paraffin feed to convert at least a portion of the cycloparaffins to alkylaromatics and provide a mildly reformed distillate range stream; (c) treating a stream comprising the mildly reformed distillate range stream in a molecular redistribution reactor to provide a distributed stream; (d) dewaxing at least a portion of the distributed stream to provide a dewaxed stream; (e) combining at least a portion of the dewaxed stream with the stream to be processed in the molecular redistribution reactor to provide the distributed stream; and (f) isolating a moderately aromatic isoparaffinic base oil from the dewaxed stream.
    Type: Grant
    Filed: November 28, 2007
    Date of Patent: June 29, 2010
    Assignee: Chevron U.S.A. Inc.
    Inventor: Dennis J. O'Rear
  • Patent number: 7732650
    Abstract: A processing scheme and system for enhanced light olefin production, particularly for increased relative yield of propylene, involves oxygenate conversion to olefins and subsequent oxygenate conversion effluent stream treatment including cross-metathesis of 1-butene with 2-butene, metathesis of 2-butene with ethylene, conversion or removal of at least a portion of the isobutene, and/or isomerization of at least a portion of 1-butene to 2-butene to produce additional propylene. The processing scheme and system may further involve a reaction with distillation column for the metathesis of butenes with ethylene to produce propylene and/or a reaction with distillation column for the conversion of isobutenes with an oxygenate-containing material to produce a tertiary ether or alcohol.
    Type: Grant
    Filed: August 6, 2009
    Date of Patent: June 8, 2010
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Bryan K. Glover
  • Patent number: 7586018
    Abstract: A processing scheme and system for enhanced light olefin production, particularly for increased relative yield of propylene, involves oxygenate conversion to olefins and subsequent oxygenate conversion effluent stream treatment including dimerization of ethylene to butene and metathesis of butenes and/or hexenes with ethylene. The processing scheme and system may further involve isomerization of at least a portion of 1-butene to 2-butene to produce additional propylene.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: September 8, 2009
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Bryan K. Glover
  • 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: 7388119
    Abstract: The present invention relates to a process for the hydrogenation of substituted or unsubstituted, monocyclic or polycyclicaromatics to form the corresponding cycloaliphatics, in particular of benzene to cyclohexane, by bringing the aromatic into contact with a hydrogen-containing gas in the presence of a catalyst, where hydrogen in which residual gases are present is used.
    Type: Grant
    Filed: July 18, 2002
    Date of Patent: June 17, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Arnd Böttcher, Ekkehard Schwab, Ralf Kästner, Jochem Henkelmann, Gerd Kaibel, Heinrich Laib
  • Patent number: 7311815
    Abstract: A method of preparing high linear paraffin or high end-chain monomethyl content products is accomplished by converting synthesis gas in a Fischer-Tropsch reaction to hydrocarbon products. These may be hydrotreated to provide an n-paraffin content of greater than 50% by weight, with substantially all branched paraffins being monomethyl end-chain branched paraffins. At least one non-linear paraffin isomer, which may be a monomethyl paraffin isomer, may be separated from the hydrocarbon products through distillation to provide an n-paraffin product having an n-paraffin content percentage by weight of the n-paraffin product that is greater than the initial n-paraffin content.
    Type: Grant
    Filed: April 30, 2003
    Date of Patent: December 25, 2007
    Assignee: Syntroleum Corporation
    Inventor: Armen N. Abazajian
  • Patent number: 6841713
    Abstract: The invention relates to economical and efficient methods for producing 2-methylene-3-methylbicyclo[2,2,1]heptane, 2,3-dimethylbicyclo[2.2.1]hept-2-ene and the like that are useful for materials of producing base oil of traction drive fluid for traction drive lubricating oil. The methods comprise reacting one or more C3-4 acyclic olefins with cyclopentadiene and isomerizing the resulting bicyclo[2.2.1]heptene derivatives in the presence of an isomerization catalyst to give one or more bicyclo[2.2.1]heptane derivatives.
    Type: Grant
    Filed: February 6, 2001
    Date of Patent: January 11, 2005
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Toshiyuki Tsubouchi, Yukio Yoshida, Motohisa Ido, Masahiro Katayama
  • Publication number: 20040260132
    Abstract: The invention relates to a process for preparing 4-vinylcyclohexene, which comprises the steps
    Type: Application
    Filed: July 20, 2004
    Publication date: December 23, 2004
    Inventors: Christian Walsdorff, Gotz-Peter Schindler, Klaus Harth, Hartmut Hibst
  • 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: 6528693
    Abstract: 1-chloropropylethyne is prepared by dehydrochlorination with a base of 1-chloro-1-cyclopropylethene, which is itself prepared by treating 1-cyclopropylethanone with dichlorotriarylphosphorane or dichlorotrialkylphosphorane in the presence of a base.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: March 4, 2003
    Assignee: Great Lakes (UK) Limited
    Inventors: Robert Gandy, Peter John Cremins, Allan Williams Timms
  • Patent number: 6392109
    Abstract: An integrated process for producing alkylbenzenes, sulfonated alkylbenzenes and/or alkylcyclohexanes from syngas is disclosed. The process involves subjecting syngas to Fischer-Tropsch conditions. Fractions rich in C6-8 and C18-26 hydrocarbons are isolated from the resulting product stream. The C6-8 fraction is subjected to catalytic reforming conditions to form aromatics. The C18-26 fraction may include sufficient olefins for use in an alkylation reaction with the aromatics. Optionally, the fraction may be subjected to dehydrogenation conditions to provide additional olefins. The resulting olefins are reacted with the aromatics in an alkylation reaction to yield alkylbenzenes. Unconverted olefins, paraffins, and aromatics can be obtained from the product stream via fractional distillation and recycled to form additional products. The alkylbenzenes can be hydrogenated to yield alkylcyclohexanes, which are useful as synlubes or as components in lube oil compositions.
    Type: Grant
    Filed: February 29, 2000
    Date of Patent: May 21, 2002
    Assignee: Chevron U.S.A. Inc.
    Inventors: Dennis J. O'Rear, William L. Schinski
  • 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
  • Publication number: 20010044564
    Abstract: A method for producing a cyclopentane product which comprises the following steps: (a) cracking dicyclopentadiene to form a cyclopentadiene-rich stream and a higher boiling liquids stream; (b) separating the cyclopentadiene-rich stream from the higher boiling liquids stream; (c) diluting the cyclopentadiene-rich stream with recycled saturates such that the cyclopentadiene content is limited to between about 5-50%; (d) conducting a first hydrogenation of the cyclopentadiene-rich stream in the presence of hydrogen and a first catalyst, and at a temperature (i.e., preferably between about 26 to 94° C., more preferably in the range between about 37 to 66° C.
    Type: Application
    Filed: July 19, 2001
    Publication date: November 22, 2001
    Inventors: James R. Lattner, C. Harry McMullen, Leonel E. Sanchez, Steven E. Silverberg, Tronze-I Dennis Wu
  • Patent number: 6180835
    Abstract: A cyclopropylacetylene derivative of the formula (V): is prepared by reacting a propynol derivative of the formula (I): with a propane derivative of the formula (VI): in the presence of a base in an amount of 2 or more equivalents relative to the propynol derivative to give a cyclopropane derivative of the formula (III): deprotecting the protecting group for the hydroxyl group of the cyclopropane derivative to give a cyclopropylpropynol derivative of the formula (IV): and subjecting the cyclopropylpropynol derivative to retro-ethynylation. In the above formulas R1, R2, R3, R4 and R5 represent hydrogen; or an alkyl, alkenyl, aryl or aralkyl group, each of which may have a substituent, R6 and R7 is hydrogen; or an alkyl, alkenyl, aryl or aralkyl group, each of which may have a substituent, or R6 and R7 taken together form a ring, R8 is a protecting group for the hydroxyl group and X and Y are each a leaving group.
    Type: Grant
    Filed: February 5, 1999
    Date of Patent: January 30, 2001
    Assignee: Kuraray Co., Ltd.
    Inventors: Goro Asanuma, Kazuya Takaki, Shigeo Ohzono, Manzo Shiono
  • 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: 6025512
    Abstract: This invention relates to a method to produce pentfulvenes comprising combining a partially substituted cyclopentadiene with a carbonyl containing compound and lithium or an alkyl lithium, wherein the partially substituted cyclopentadiene is represented by the formula: ##STR1## wherein the R.sup.1 to R.sup.5 groups are independently hydrogen or a C.sub.1 to C.sub.100 group, provided at least one R group is hydrogen but not more than three R groups are hydrogen.
    Type: Grant
    Filed: January 6, 1999
    Date of Patent: February 15, 2000
    Assignee: Univation Technologies, LLC
    Inventors: Donna Jean Crowther, Jorge L. Zamora
  • Patent number: 5998683
    Abstract: A method for producing a cyclopentane product which comprises the following steps: (a) cracking dicyclopentadiene to form a cyclopentadiene-rich stream and a higher boiling liquids stream; (b) separating the cyclopentadiene-rich stream from the higher boiling liquids stream; (c) diluting the cyclopentadiene-rich stream with recycled saturates such that the cyclopentadiene content is limited to between about 5-50%; (d) conducting a first hydrogenation of the cyclopentadiene-rich stream in the presence of hydrogen and a first catalyst, and at a temperature (i.e., preferably between about 26 to 94.degree. C., more preferably in the range between about 37 to 66.degree. C.
    Type: Grant
    Filed: July 24, 1997
    Date of Patent: December 7, 1999
    Assignee: Exxon Chemicals Patents Inc.
    Inventors: James R. Lattner, C. Harry McMullen, Leonel E. Sanchez, Steven E. Silverberg, Tronze-I Dennis Wu
  • Patent number: 5959167
    Abstract: A process for converting lignin into high-quality reformulated hydrocarbon gasoline compositions in high yields is disclosed. The process is a two-stage, catalytic reaction process that produces a reformulated hydrocarbon gasoline product with a controlled amount of aromatics. In the first stage, a lignin material is subjected to a base-catalyzed depolymerization reaction in the presence of a supercritical alcohol as a reaction medium, to thereby produce a depolymerized lignin product. In the second stage, the depolymerized lignin product is subjected to a sequential two-step hydroprocessing reaction to produce a reformulated hydrocarbon gasoline product. In the first hydroprocessing step, the depolymerized lignin is contacted with a hydrodeoxygenation catalyst to produce a hydrodeoxygenated intermediate product.
    Type: Grant
    Filed: August 19, 1998
    Date of Patent: September 28, 1999
    Assignee: The University of Utah Research Foundation
    Inventors: Joseph S. Shabtai, Wlodzimierz W. Zmierczak, Esteban Chornet