Polymerization And Depolymerization Patents (Class 585/832)
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Patent number: 8809613Abstract: The present invention relates to a method for preparing linear alpha-olefins (LAO) by oligomerization of ethylene in the presence of a solvent and homogeneous catalyst, comprising the steps of: (i) feeding ethylene, solvent and catalyst into an oligomerization reactor, (ii) oligomerizing the ethylene in the reactor, (iii) removing a reactor outlet stream comprising solvent, linear alpha-olefins, optionally unreacted ethylene and catalyst from the reactor via a reactor outlet piping system, (iv) dosing at least one additive selected from the group consisting of alcohols, poly-ethylene glycols, polyethylene glycol monoethers, polyethylene glycol diethers, polyamines, amines, amino alcohols and surfactants, (v) transferring the reactor outlet stream containing the additive to a catalyst deactivation and removal section, and (vi) deactivating the catalyst with caustic and removing the deactivated catalyst from the reactor outlet stream, wherein the residence time of the additive in the reactor outlet stream priType: GrantFiled: May 28, 2010Date of Patent: August 19, 2014Assignees: Saudi Basic Industries Corporation, Linde AGInventors: Peter M. Fritz, Heinz Bölt, Andreas Meiswinkel, Carsten Taube, Florian Winkler, Volker Göke, Wolfgang Müller, Anina Wöhl, Richard Schneider, Uwe Rosenthal, Helmut Fritz, Bernd H. Müller, Normen Peulecke, Stephan Peitz, Bhaskar Reddy Aluri, Mohammed Al-Hazmi, Shahid Majeed Azam, Fuad Mosa, Abdullah Al-Dugathier
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Publication number: 20100095591Abstract: A system includes a fuel converter comprising a catalyst composition, and the catalyst composition can convert fuel into a hydrocarbon reductant stream; a separation system that separates the hydrocarbon reductant stream into a first reductant sub-stream that comprises short chain hydrocarbon molecules, and a second reductant sub-stream that comprises long chain hydrocarbon molecules; a selective catalytic reduction catalyst reactor in fluid communication with the fuel converter, and the catalyst reactor has an inner surface that defines a first zone and a second zone, and the first zone is configured to receive the second reductant sub-stream, and the second zone is configured to receive the first reductant sub-stream; and an exhaust stream that flows into the first zone contacts the second reductant sub-stream before flowing into the second zone and contacting the first reductant sub-stream.Type: ApplicationFiled: October 20, 2008Publication date: April 22, 2010Applicant: GENERAL ELECTRIC COMPANYInventors: Dan Hancu, Ashish Balkrishna Mhadeshwar, Daniel George Norton, Frederic Vitse, Benjamin Hale Winkler
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Patent number: 7388122Abstract: The present invention relates to dewaxing aids comprising the mixture of two or more polyalkyl(meth)acrylates having an exothermic heat initiation temperature within the specific range when chilled at 30° C./minute rate, to be added together with the wax-containing hydrocarbon oil to the dewaxing solvent. The dewaxing aid according to the present invention can be used in the solvent dewaxing method containing the stage in which the chilling rate during the chilling is 30° C./minute or higher, is effective for heavy type wax-containing hydrocarbon oils, and is chlorine-free.Type: GrantFiled: October 25, 2002Date of Patent: June 17, 2008Assignee: Toho Chemical Industry Co., LtdInventors: Naoki Haga, Akiyuki Hiraide
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Patent number: 7202391Abstract: According to the present invention, there is provided a process for inhibiting the polymerization of an aromatic vinyl compound which is capable of efficiently inhibiting the polymerization of an aromatic vinyl compound not only in an initial stage but also over a long term in the stage of producing, purifying, storing or transporting the aromatic vinyl compound, and which is excellent in handling. The present invention relates to a process for inhibiting the polymerization of an aromatic vinyl compound which requires the step of adding a 2-nitrophenol compound in combination with a sulfonic acid compound to the aromatic vinyl monomer during the stage of producing, purifying, storing or transporting the aromatic vinyl compound.Type: GrantFiled: April 18, 2002Date of Patent: April 10, 2007Assignee: Hakuto Co., Ltd.Inventors: Seiji Tanizaki, Junichi Nakajima
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Patent number: 7166658Abstract: A method of reducing vulcanized rubber is provided. The method comprises the steps of heating the rubber, wherein the rubber includes synthetic rubber, in the presence of a solvent, wherein the solvent includes water to a temperature below a critical temperature of the solvent, providing a pressure that is at least equal to a saturated vapour pressure of the solvent at the temperature and maintaining the temperature and the pressure for a time sufficient to devulcanize the rubber and produce a reaction product that is primarily a solid phase and includes rubber hydrocarbon.Type: GrantFiled: September 18, 2003Date of Patent: January 23, 2007Assignees: Sorbecon Consultants Inc., OPW Enterprises Inc.Inventors: Brian H. Harrison, Hurdon Hooper
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Patent number: 6960279Abstract: Disclosed is the observation that 7-aryl-quinone methides and 4-tert-butylcatechol, when used in combination in a vinyl aromatic monomer to inhibit polymerization,do not inhibit polymerization to the same extend as each would if used separately. Stated another way, a phenomenon has been observed that when these two compounds are used together, they can, to a large extent, render each other unable to inhibit polymerization in a vinyl aromatic monomer. Also disclosed are methods of preventing adverse results of this interaction when undesired and a method of using this interaction to prepare a reactive vinyl aromatic monomer having a concentration of 4-tert-butylcatechol that would otherwise inhibit polymerization. The invention is disclosed to be useful with the production and storage of any vinyl aromatic monomer and is disclosed to be particularly useful with the production and storage of styrene monomer.Type: GrantFiled: May 6, 2002Date of Patent: November 1, 2005Assignee: Fina Technology, Inc.Inventor: James T. Merrill
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Patent number: 6660181Abstract: A method is disclosed for inhibiting the premature polymerization of ethylenically unsaturated monomers comprising adding to said monomers a polymerization inhibiting amount of a mixture comprising A) a first inhibitor comprising 4-amino-2,2,6,6-tetramethylpiperidinyloxy, wherein said amino group is a primary, secondary, or tertiary amino group; and B) at least one other inhibitor having the structural formula: wherein: R1 and R4 are independently selected from the group consisting of hydrogen, alkyl, and heteroatom-substituted alkyl; R2 and R3 are independently selected from the group consisting of alkyl and heteroatom-substituted alkyl; X1 and X2 (1) are independently selected alkyl groups of 1 to 15 carbon atoms or (2) taken together, form a ring structure with the nitrogen.Type: GrantFiled: July 12, 2002Date of Patent: December 9, 2003Assignee: Crompton CorporationInventors: Brigitte Benage, Angela M. Edwards, Vilen Kosover, Gan Wang, Anthony Gentile, Jesus R. Fabian, Gerald J. Abruscato
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Publication number: 20030100807Abstract: The invention includes a process for converting biomass into C7-C10 alkylbenzenes useful as blending components for petroleum or petroleum derived fuels. The process includes a base catalyzed depolymerization of lignin within the biomass, followed by hydroprocessing of the depolymerized lignin to C7-C10 alkylbenzenes. The C7-C10 alkylbenzenes are useful for enhancing the octane level of petroleum or petroleum-derived fuels, such as gasoline. In addition, the C7-C10 alkylbenzenes are useful as intermediates in the production of numerous organic chemicals.Type: ApplicationFiled: October 5, 2001Publication date: May 29, 2003Inventors: Joseph S. Shabtai, Wlodzimierz W. Zmierczak, Esteban Chornet, David Johnson
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Patent number: 6518453Abstract: In a process for stabilizing chemical compounds having at least one ethylenically unsaturated bond to undesired free radical polymerization, a nitroxyl radical and a chemical compound containing phosphorus in chemically bonded form are added to the unsaturated compound present as pure substance or as a component of a mixture.Type: GrantFiled: July 3, 2001Date of Patent: February 11, 2003Assignee: BASF AktiengesellschaftInventors: Heinz Friedrich Sutoris, Gerhard Wagenblast, Volker Schliephake, Jürgen Schröder, Klaus Joachim Müller-Engel, Harald Keller, Thomas Jaworek
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Patent number: 6504068Abstract: A method of converting a plastic waste into oil by decomposing the plastic waste by a reaction using water in a supercritical or near supercritical region as a reaction medium. In this method, the reaction is conducted by using a tubular continuous reactor. The present invention further provides an apparatus therefor. Moreover, the present invention provides a method of converting a plastic waste into oil by conducting the reaction after hydrogen chloride is removed by performing the pyrolysis of the plastic waste in the case that the plastic waste contain chlorine. The present invention further provides an apparatus for performing this method.Type: GrantFiled: June 6, 1997Date of Patent: January 7, 2003Assignee: Mitsubishi Jukogyo Kabushiki KaishaInventors: Wataru Matsubara, Hiroshi Makihara, Kazuto Kobayashi, Masaki Iijima
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Publication number: 20020082463Abstract: The present invention describes a pressure swing adsorption (PSA) apparatus and process for the production of purified hydrogen from a feed gas stream containing heavy hydrocarbons (i.e., hydrocarbons having at least six carbons). The apparatus comprises at least one bed containing at least three layers. The layered adsorption zone contains a feed end with a low surface area adsorbent (20 to 400 m2/g) which comprises 2 to 20% of the total bed length followed by a layer of an intermediate surface area adsorbent (425 to 800 m2/g) which comprises 25 to 40 % of the total bed length and a final layer of high surface area adsorbent (825 to 2000 m2/g) which comprises 40 to 78% of the total bed length.Type: ApplicationFiled: December 22, 2000Publication date: June 27, 2002Inventors: Timothy Christopher Golden, Edward Landis Weist
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Patent number: 6403850Abstract: Disclosed herein is a method for inhibiting the premature polymerization of ethylenically unsaturated monomers comprising adding to said monomers an effective amount of: A) at least one stable hindered nitroxyl compound having the structural formula: wherein R1 and R4 are independently selected from the group consisting of hydrogen, alkyl, and heteroatom-substituted alkyl and R2 and R3 are independently selected from the group consisting of alkyl and heteroatom-substituted alkyl; and X1 and X2 (1) are independently selected from the group consisting of halogen, cyano, COOR7, —S—COR7, —OCOR7, (wherein R7 is alkyl of 1 to 15 carbon atoms, or (2) taken together, form a ring structure with the nitrogen; and B) at least one phenylenediamine, and, optionally, C) at least one nitroaromatic compound.Type: GrantFiled: July 17, 2000Date of Patent: June 11, 2002Assignee: Uniroyal Chemical Company, Inc.Inventors: Brigitte Benage, Andrew J. Eisenstein
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Patent number: 6395942Abstract: Compounds that inhibit polymerization of vinyl aromatic compounds need to operate at temperatures of about 90° C. to about 150° C. A process for increasing the thermal stability of inhibitors such as N,N′-di-2-butyl-N,N′-dinitroso-1,4-diaminobenzene is disclosed. The process comprises adding to the inhibitor a stabilizer such as N,N′-di-2-butyl-1,4-diaminobenzene. The mixture of inhibitor and stabilizer is also used to inhibit polymerization of vinyl aromatic compounds.Type: GrantFiled: August 10, 1999Date of Patent: May 28, 2002Assignee: UOP LLCInventors: Paul R. Kurek, Robert R. Frame
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Patent number: 6395943Abstract: A process is disclosed for inhibiting the polymerization of vinyl aromatic compounds, such as styrene, during its distillation. The process involves adding a mixture of at least two inhibitors to the vinyl aromatic compound. One such combination is N,N′-di-2-butyl-N,N′,4-dinitroso-1,4-diaminobenzene and dinitrocresol. A stabilizer such as N,N′-di-2-butyl-1,4-diaminobenzene can also be added.Type: GrantFiled: August 10, 1999Date of Patent: May 28, 2002Assignee: UOP LLCInventors: Paul R. Kurek, Robert R. Frame
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Patent number: 6262172Abstract: A method for preparing a carbonized resin DNA immunoadsorbent, which uses styrene, acrylonitrile, divinylbenzene, toluene, liquid paraffin, benzoyl peroxide and water solution of polyvinyl alcohol as raw materials, produces a DNA immunoadsorbent with 0.3-0.5 mg DNA per milliliter of resin using two-staged procedures for preparation of first carbonized resin, and secondly carbonized resin DNA immunoadsorbent. The resultant immunoadsorbent is high in adsorbent capacity, low in production cost, and can be synthesized without pyrogens. It therefore satisfies the demands of medical application for the treatment of systemic lupus erythematosus by immunoadsorption.Type: GrantFiled: February 7, 2000Date of Patent: July 17, 2001Assignee: Nankai UniversityInventors: Yaoting Yu, Changzhi Chen, Deling Kong
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Patent number: 6200460Abstract: Substance mixtures comprising (A) vinyl-containing compounds, (B) an active amount of a mixture inhibiting the premature polymerization of the vinyl-containing compounds, comprising (i) at least one N-oxyl compound of a secondary amine which carries no hydrogen atoms on the &agr;-C atoms, and (ii) at least one iron compound, (C) if appropriate nitro compounds, and (D) if appropriate costabilizers, a process for inhibiting the premature polymerization of vinyl-containing compounds (A) and the use of mixture (B), if appropriate as a mixture with nitro compounds (C) and/or costabilizers (D), for inhibiting the premature polymerization of free radical polymerizable compounds and for stabilizing organic materials against the damaging action of free radicals.Type: GrantFiled: December 16, 1998Date of Patent: March 13, 2001Assignee: BASF AktiengesellschaftInventors: Heinz Friedrich Sutoris, Hermann Uhr, Konrad Mitulla, Jürgen Schröder, Roland Merger, Knut Kessel
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Patent number: 6024894Abstract: Synergistic composition and method of use are disclosed. The compositions comprise a quinone methide derivative and a hydroxylamine compound. These compositions demonstrate synergism at inhibiting the polymerization of a vinyl aromatic monomer. Preferably the quinone methide derivative is 2,6-di-tert-butyl-4-benzylidene-cyclo-2,5-dienone and the hydroxylamine compound is N,N-bis(hydroxypropyl)hydroxylamine.Type: GrantFiled: March 25, 1998Date of Patent: February 15, 2000Assignee: BetzDearborn Inc.Inventor: Graciela B. Arhancet
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Patent number: 5998490Abstract: A process and resulting product is provided in which a solid particulate, such as vulcanized crumb rubber, has the surface functional groups oxidized by ozonation using a nonpolar solvent. The ozonation process renders the treated crumb rubber more suitable for use in new rubber formulations. As a result, larger loading levels of the treated crumb rubber can be used in new rubber mixtures.Type: GrantFiled: May 8, 1997Date of Patent: December 7, 1999Assignee: Westinghouse Savannah River CompanyInventor: Steven M. Serkiz
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Patent number: 5973217Abstract: According to the process described, old or waste plastics are depolymerized into a pumpable phase and a volatile phase to allow recovery of chemical raw materials and liquid fuel components. The volatile phase is separated into a gaseous phase and a condensate. In order to simplify the process in comparison with the state of the art, the depolymerised product remaining after the volatile phase is separated is also heated together with the condensate or condensate fractions in the presence of hydrogen under pressure and is subjected to hydrotreating, after non-boiling components are removed, to produce syncrude.Type: GrantFiled: January 9, 1998Date of Patent: October 26, 1999Assignee: Veba Oel AGInventors: Horst Hastrich, Christian Hecka, Rolf Holighaus, Klaus Niemann, Claus Strecker
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Patent number: 5942649Abstract: Method for thermally decomposing addition polymers, such as polyolefins, into monomers and monomer fragments. Thermal decomposition occurs by the rapid heating of the addition polymer such that the polymer ceiling temperature is reached in a time period substantially equal to the thermal relaxation time of the polymer itself. Laser ablation, wherein the polymer is heated by very rapid nanosecond or microsecond pulses of ultraviolet or infrared laser beams, and flash pyrolysis are particularly useful techniques for accomplishing such rapid heating.Type: GrantFiled: December 18, 1997Date of Patent: August 24, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Graciela Beatriz Blanchet-Fincher, Curtis Robinson Fincher, Jr.
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Patent number: 5907071Abstract: The polymerization of vinyl aromatic monomers such as styrene is inhibited by the addition of a composition of a stable hindered nitroxyl radical and an oxime compound.Type: GrantFiled: April 21, 1998Date of Patent: May 25, 1999Assignee: BetzDearborn Inc.Inventor: Graciela B. Arhancet
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Patent number: 5877366Abstract: A process and a system for cracking dicyclopentadiene are disclosed pursuant to the process preheated dicyclopentadiene is introduced into a heated transfer fluid sufficiently below the transfer fluid surface to accomplish substantially complete conversion of said dicyclopentadiene to monomeric cyclopentadiene vapor.Type: GrantFiled: March 25, 1992Date of Patent: March 2, 1999Assignee: Boulder Scientific CompanyInventor: John M. Birmingham
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Patent number: 5841011Abstract: Light-weight oil having a high octane number is produced from waste plastics containing phthalic polyester and/or polyvinyl chloride at a high yield without producing a phthalic sublimate or a carbonaceous residue by pyrolyzing the waste plastics in an atmosphere of steam or a steam/inert gas mixture. The resulting pyrolyzed oil and pyrolyzed gas may be catalytically cracked in an atmosphere of steam or a steam/inert gas mixture. Dechlorination may be performed before pyrolysis is carried out. Pyrolysis is preferably carried out in the presence of at least one of iron hydroxide, hydrous iron oxide and iron oxide.Type: GrantFiled: February 6, 1997Date of Patent: November 24, 1998Assignees: Kenji Hashimoto, NGK Insulators, LtdInventors: Kenji Hashimoto, Takao Masuda, Shuichi Yoshida, Yuichi Ikeda
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Patent number: 5744672Abstract: A method for inhibiting the polymerization of vinyl aromatics such as styrene with a mixture of 3,5-di-tert-butyl-4-hydroxy-N,N-dimethylbenzyl amine and carboxylic acids or anhydrides thereof, in the presence of air or oxygen. The weight ratio of said 3,5-Di-tert-butylhydroxy-N,N-dimethylbenzyl amine, carboxylic acid (or carboxylic acid anhydride) and the air is 1:1 to 0.05:0.05 to 15, respectively.Type: GrantFiled: January 23, 1996Date of Patent: April 28, 1998Inventors: Vladimir Anatolievich Kourbatov, Nataljya Pavlovna Boreyko, Valerii Pavlovich Zouev, Alexandr Grigorievich Liakumovich
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Patent number: 5728917Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.Type: GrantFiled: October 30, 1995Date of Patent: March 17, 1998Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, SonBinh T. Nguyen
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Patent number: 5672794Abstract: Monomeric styrene is recovered from plastics waste containing styrene polymers by thermal depolymerization by a process in which the waste is transported in liquid or solid form into a fluidized bed of a solid heat transfer agent and is cracked or depolymerized in an average residence time of less than 60 seconds and styrene is obtained from the gaseous crack products. Preferably, magnesium aluminum silicate is used as a heat transfer agent and C.sub.1 -C.sub.6 -hydrocarbons formed as byproducts in the depolymerization are used as operating gas for maintaining the fluidized bed and are circulated.Type: GrantFiled: August 29, 1996Date of Patent: September 30, 1997Assignee: BASF AktiengesellschaftInventor: Andreas Northemann
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Patent number: 5545782Abstract: Nitroxyl inhibitors in combination with some oxygen reduce the premature polymerization of vinyl aromatic monomers during the manufacturing processes for such monomers. Even small quantities of air used in combination with the nitroxyl inhibitors result in vastly prolonged inhibition times for said monomers.Type: GrantFiled: May 17, 1995Date of Patent: August 13, 1996Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn
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Patent number: 5545786Abstract: Nitroxyl inhibitors in combination with some oxygen reduce the premature polymerization of vinyl aromatic monomers during the manufacturing processes for such monomers. Even small quantities of air used in combination with the nitroxyl inhibitors result in vastly prolonged inhibition times for said monomers.Type: GrantFiled: February 3, 1995Date of Patent: August 13, 1996Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn
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Patent number: 5516952Abstract: A process for breaking down rubber polymer materials by selective oxidative decoupling of carbon-carbon, carbon-sulfur and sulfur-sulfur bonds at supercritical or near supercritical conditions for water and wherein supercritical water or water near supercritical conditions is used as a solvent and reforming agent, is used to produce relatively high yields of lower molecular weight hydrocarbons and oxygenated hydrocarbons which are suitable for use as a fuel or which can be separated or further refined to produce various commodity chemicals, specialty chemicals or both. The invention provides an environmentally friendly process for recycling rubber waste materials such as waste tires to generate valuable fuels or chemical feedstocks in a closed oxidation process which is free of hazardous stack emissions.Type: GrantFiled: December 13, 1994Date of Patent: May 14, 1996Assignee: The University of AkronInventors: Sunggyu Lee, Fouad O. Azzam, Brian S. Kocher
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Patent number: 5443716Abstract: A process is provided for converting a hydrocarbon feedstock comprising at least 2 volume percent of a low molecular weight oligomer to hydrocarbon product useful in the manufacture of fuels comprising contacting the hydrocarbon feedstock with a catalytic cracking catalyst at catalytic cracking conditions for converting at least a portion of the low molecular weight oligomer to hydrocarbon suitable for blending into fuels.Type: GrantFiled: September 28, 1994Date of Patent: August 22, 1995Assignee: Amoco CorporationInventors: Ken B. Anderson, Jeffrey T. Miller
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Patent number: 5321177Abstract: 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: GrantFiled: April 16, 1992Date of Patent: June 14, 1994Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Takao Nakamura, Masaru Kawakita, Katsumi Minomiya
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Patent number: 5292992Abstract: Conjugated diene impurities are removed from linear alpha-olefin products by contacting the linear alpha-olefin product with an acid treated montmorillonite clay which is effective to reduce the conjugated diene content of the linear alpha-olefin product, preferably to less than about 100 ppm, without substantial isomerization of the linear alpha-olefins to internal olefins.Type: GrantFiled: March 30, 1993Date of Patent: March 8, 1994Assignee: Ethyl CorporationInventors: Stephen E. Belmont, Patrick G. Simms, Keith G. Anderson
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Patent number: 4835335Abstract: A two-stage catalytic conversion process for converting an olefins-containing feed is disclosed which comprises contacting the feed in a first stage under substantially non-oligomerizing conditions with a catalyst comprising at least one metal (X) selected from the group consisting of metals from Groups 1a, 1b, 2a, 2b, 4b, 5b, 6b and 8 of the Periodic Table of the Elements and contacting the effluent from the first stage in the second stage under olefin oligomerization conditions at a temperature which is at least 50.degree. C. above the operating temperature of the first stage with a catalyst comprising at least one metal (Z) selected from the group consisting of metals from Groups 1b, 2a, 2b, 4b, 5b, 6b, and 8 on a mordenite-type of crystalline trivalent metal (Q) silicate.Type: GrantFiled: March 2, 1988Date of Patent: May 30, 1989Assignee: Shell Oil CompanyInventors: Johannes P. van den Berg, Pierre Grandvallet, Andras G. T. G. Kortbeek
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Patent number: 4795842Abstract: The invention relates to the conversion of methane to higher hydrocarbons by contact with a solid oxidative synthesizing agent, the specific improvement being the addition to the reaction system of one or more components of the oxidative synthesizing agent which are lost during the reaction.Type: GrantFiled: August 4, 1987Date of Patent: January 3, 1989Assignee: Atlantic Richfield CompanyInventors: Anne M. Gaffney, C. Andrew Jones, John A. Sofranko
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Patent number: 4645576Abstract: This invention provides a process for isolating and recovering butene-1 of high purity at high yield. Firstly, a butane-butene fraction containing 0.1 to 7 wt % of isobutylene, 10 to 50 wt % of butene-1 and 5 to 20 wt % of isobutane is rectified to reduce the content of isobutane to not more than 0.1 wt %. Then, the rectified butane-butene fraction is passed through a reactor packed with an extrusion molded silica-alumina catalyst to polymerize isobutylene at a reaction velocity as high as 50 times or more of that of butene-1, thus forming oligomers of isobutylene. Finally, the hydrocarbon mixture from the reactor is rectified to remove the oligomers of isobutylene and the other C.sub.4 -hydrocarbons.Type: GrantFiled: May 10, 1984Date of Patent: February 24, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Tetsuya Takezono, Takaaki Amari, Hirosuke Imai
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Patent number: 4522688Abstract: The process gives highly pure cyclopentadiene and methylcyclopentadiene from a cracked gasoline fraction. The merit of the process is that cyclopentadiene and methylcyclopentadiene are recovered by adding a simple distillation system to a conventional cracked gasoline treating plant without altering the plant and operating conditions thereof. An internal reflux stream is withdrawn from the stripping section of a BTX column of a conventional cracked gasoline treating plant, and is sent to a depolymerization-distillation column operated at a bottom temperature of 160.degree.-230.degree. C. The overhead stream of the column is sent to a cyclopentadiene column operated at a bottom temperature of 160.degree.-230.degree. C. Cyclopentadiene is recovered from the overhead of the column, and the bottom stream is sent to methylcyclopentadiene column operated at a bottom temperature of 170.degree.-210.degree. C. Methylcyclopentadiene is recovered from the overhead of the column.Type: GrantFiled: October 26, 1983Date of Patent: June 11, 1985Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Akira Yokogawa, Asao Takahashi, Isao Maruyama, Takao Hosaka
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Patent number: 4520225Abstract: The invention relates to a process for the pretreatment of a light olefin fraction, or of a mixture of such fractions, for the purpose of selectively removing the isobutene and butadiene present.In accordance with the invention, the olefin fraction is contacted with boron trifluoride in the gas phase, under such conditions and for such a length of time that the isobutene and the butadiene will polymerize selectively, and the boron trifluoride and the isobutene and butadiene polymers obtained are then conventionally separated from the effluent.Type: GrantFiled: November 14, 1983Date of Patent: May 28, 1985Assignee: Compagnie Francaise de RaffinageInventors: Claude Marty, Philippe Engelhard
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Patent number: 4513166Abstract: 1-Butene and isobutene are effectively separated without isomerization of 1-butene by contacting an isobutene-containing hydrocarbon mixture with a solid acid catalyst having a solid acid quantity of 0.05 to 0.25 mmol/g of solid acid catalyst, represented by the adsorption quantity of pyridine, thus low-polymerizing selectively isobutene and then separating the low polymers of isobutene from 1-butene.Type: GrantFiled: April 6, 1984Date of Patent: April 23, 1985Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Satoshi Sakurada, Takao Hashimoto, Nobuaki Tagaya, Tsugio Maeshima, Kayako Ueda, Masahiro Kokubo
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Patent number: 4482775Abstract: A method for isomerizing isobutene or n-butene to produce a mixture of isobutene and normal butene, and polymerizing at least a portion thereof to produce isobutene/n-butene codimer, which comprieses feeding at least 80 weight % of either the isobutene or n-butene to a catalytic distillation reactor containing a fixed bed acidic cation exchange resin catalyst packing which provides both the catalyst sites and distillation sites for the reaction products, isomerizing a portion of the isobutene or n-butene to produce a mixture of isobutene and n-butene and reacting at least a portion of the isobutene and n-butene to form codimer of isobutene and n-butene, whereby an overhead fraction containing any unreacted isobutene and n-butene and a bottoms fraction containing codimer is produced. The result of the reaction is substantially the same regardless whether the feed is isobutene or n-butene. Other aspects of the invention, include combinations of procedures to produce high purity isobutene and n-butene.Type: GrantFiled: September 22, 1982Date of Patent: November 13, 1984Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4479023Abstract: A process for the oligomerization of olefin fractions where boron trifluoride in the gas phase is contacted with such a fraction, in the absence of a catalyst carrier, under such conditions and for such a length of time that the isobutene and/or butadiene present will polymerize; the boron trifluoride and the isobutene and/or butadiene polymers obtained are then conventionally separated from said fraction; and the olefins of the fraction so purified are oligomerized in the presence of a boron trifluoride catalyst comprising a catalyst carrier.Type: GrantFiled: December 8, 1983Date of Patent: October 23, 1984Assignee: Compagnie Francaise de RaffinageInventors: Claude Marty, Philippe Engelhard
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Patent number: 4471153Abstract: The presence of cyclopentadiene in unsaturated C.sub.5 -hydrocarbons is often very undesirable. This is because cyclopentadiene is a poison to many of the catalysts used to polymerize C.sub.5 -hydrocarbon monomers. This invention reveals a process for reducing the concentration of cyclopentadiene in impure unsaturated C.sub.5 -hydrocarbons containing cyclopentadiene, comprising adding to said impure unsaturated C.sub.5 -hydrocarbon (a) at least one member selected from the group consisting of trialkylaluminum compounds, dialkylaluminum hydride compounds, dialkylmagnesium compounds, and dialkylzinc compounds; and (b) an organonickel compound.Type: GrantFiled: September 6, 1983Date of Patent: September 11, 1984Assignee: The Goodyear Tire & Rubber CompanyInventor: Morford C. Throckmorton
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Patent number: 4454367Abstract: 1-Butane and isobutene are effectively separated without isomerization of 1-butene by contacting an isobutene-containing hydrocarbon mixture with a solid acid catalyst having a solid acid quantity of 0.05 to 0.25 mmol/g of solid acid catalyst, represented by the adsorption quantity of pyridine, thus low-polymerizing selectively isobutene and then separating the low polymers of isobutene from 1-butene.Type: GrantFiled: March 15, 1983Date of Patent: June 12, 1984Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Satoshi Sakurada, Takao Hashimoto, Nobuaki Tagaya, Tsugio Maeshima, Kayako Ueda, Masahiro Kokubo
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Patent number: 4450310Abstract: A methane conversion process is provided for the production of olefins and hydrogen comprising contacting methane in the absence of oxygen and in the absence of water at a reaction temperature of at least 500.degree. C. with a catalyst comprising the mixed oxides of a first metal selected from lithium, sodium, potassium, rubidium, cesium and mixtures thereof, a second metal selected from beryllium, magnesium, calcium, strontium, barium, and mixtures thereof, and optionally a promoter metal selected from copper, rhenium, tungsten, zirconium, rhodium, and mixtures thereof.Type: GrantFiled: March 4, 1983Date of Patent: May 22, 1984Assignee: The Standard Oil CompanyInventors: Joseph R. Fox, Benedict S. Curatolo, Frederick A. Pesa
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Patent number: 4375576Abstract: In the liquid phase reaction of isobutene in the presence of resin cation exchange resins with itself in a C.sub.4 hydrocarbon stream to form dimers, the formation of higher polymers, oligomers, and co-dimer by-products is suppressed by the presence of 0.0001 to 1 mole per mole of isobutene of methyl tertiary butyl ether.Type: GrantFiled: July 27, 1981Date of Patent: March 1, 1983Assignee: Chemical Research & Licensing Co.Inventor: Lawrence A. Smith, Jr.
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Patent number: 4323698Abstract: This specification discloses an insoluble resin-metal compound complex, the method for its preparation, and its use in carrying out a catalyzed reaction. The complex is a weak base anion exchange resin which has been contacted with a solution of a coordination compound having at least two ligands connected to at least one central metal atom to bond chemically the resin to the metal atom by replacement of at least one of the ligands of the coordination compound by a functional group of the weak base anion exchange resin. The complex can be used as a catalyst for hydrogenation, carbon monoxide insertion, polymerization, isomerization, vinyl ester exchange, and ethylene oxidation reactions, among others.Type: GrantFiled: January 21, 1980Date of Patent: April 6, 1982Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4313016Abstract: The isobutene in C.sub.4 hydrocarbon streams containing from 0.5 to 5% isobutene and n-butenes is reduced preferably to a level of 0.2 mole % or less by passing the feed stream at LHSV 2.5 to 12 in liquid phase through a fixed-bed cation exchange resin catalyst in a tubular reactor with a water heat exchange medium maintained at a temperature of 50.degree. to 80.degree. C., whereby the isobutene is oligomerized and easily separated from the remaining C.sub.4 's by fractionation.Type: GrantFiled: October 23, 1980Date of Patent: January 26, 1982Assignee: Petro-Tex Chemical CorporationInventor: Harold E. Manning
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Patent number: 4242530Abstract: A method for the separation of isobutene from a mixture comprising n-butene and isobutene comprising feeding a C.sub.4 stream containing n-butene and isobutene to a distillation column reactor into a feed zone contacting the stream with fixed bed acidic cation exchange resin to form diisobutene which passes to the bottom of the column, said n-butene being removed overhead. The reaction and distillation occur concurrently.Type: GrantFiled: July 27, 1978Date of Patent: December 30, 1980Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4225738Abstract: This invention provides a three-step process for converting n-butene into high purity 1,3-butadiene, via a vinylcyclohexene intermediate.In the first step of the process, n-butene and molecular oxygen are contacted with a Group VIII metal oxide catalyst. If nitrobenzene is employed as the oxidizing agent in place of molecular oxygen then aniline is produced as a secondary product of the process.Type: GrantFiled: April 23, 1979Date of Patent: September 30, 1980Assignee: El Paso Products CompanyInventor: John L. Cihonski
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Patent number: 4218569Abstract: Mixed hydrocarbons of predominantly four carbon atoms each are subjected to etherification with methanol, to make ether from the tertiary olefin in the mixture; the unreacted hydrocarbons, after separation from the ether by distillation, are contaminated with methanol which is removed by absorption or extraction with a glycol before the hydrocarbons are subjected to further processing in which the methanol is detrimental.Type: GrantFiled: March 14, 1978Date of Patent: August 19, 1980Assignee: Gulf Canada LimitedInventors: John D. Chase, Buenaventura B. Galvez, Bruce W. Kennedy