Using Halogen-containing Catalyst Patents (Class 585/669)
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Patent number: 11505516Abstract: Systems and methods for producing propylene using an MTBE synthesis raffinate are disclosed. An MTBE synthesis raffinate stream first passes through a molecular sieve to separate n-butane and isobutane from the rest of C4 hydrocarbons of the MTBE synthesis raffinate. The 1-butene in the rest of C4 hydrocarbons of the MTBE synthesis raffinate is then isomerized to form 2-butene. Therefore, the concentration of 2-butene in the subsequent propylene production process increases due to the separation of n-butane and isobutane and the isomerization of 1-butene, resulting in an improved reaction rate and reaction efficiency for propylene production.Type: GrantFiled: July 17, 2018Date of Patent: November 22, 2022Assignee: SABIC GLOBAL TECHNOLOGIES B.V.Inventors: Guillermo Leal, Mohammed Bismillah Ansari
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Patent number: 8049050Abstract: A method for synthesizing exo-tetrahydrodicyclopentadiene (exo-THDCPD) and adamantane is provided, including isomerization of an endo-tetrahydrodicyclopentadiene (endo-THDCPD) as a reaction feed with an acidic ionic liquid of aluminum trichloride in a pseudo-fixed bed ionic liquid reactor. Reactants float as a droplet from bottom to top of the pseudo-fixed bed reactor, and finally are discharged from a side tube. A mole fraction of aluminum trichloride in the acidic ionic liquid of aluminum trichloride is from 0.5 to 0.9, a feeding rate of the reaction feed is 0.1-10 g/min, and a temperature for the isomerization is between 25-120° C.Type: GrantFiled: May 11, 2009Date of Patent: November 1, 2011Assignee: CPC Corporation, TaiwanInventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
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Patent number: 8017821Abstract: A process for isomerization of tetrahydrodicyclopentadiene using a supported acidic ionic liquid as catalyst is provided. In the presence of the supported acidic ionic liquid, endo-tetrahydrodicyclopentadiene is isomerized to exo-tetrahydrodicyclo-pentadiene, wherein the supported acidic ionic liquid includes a porous support and an acidic ionic liquid, and the acidic ionic liquid includes an aluminum halide, and a quaternary ammonium halide or a quaternary phosphonium halide. The porous support is impregnated with the acidic ionic liquid. Furthermore, under different reaction conditions, the exo-tetrahydrodicyclopentadiene product can be isomerized to adamantane in the presence of such a supported acidic ionic liquid.Type: GrantFiled: March 24, 2009Date of Patent: September 13, 2011Assignee: CPC Corporation, TaiwanInventors: Ming-Yu Huang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
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Patent number: 7956229Abstract: A method for producing an internal olefin by stably isomerizing an ?-olefin by using an inexpensive zeolite catalyst while preventing an oligomerization reaction is provided. The method for producing an internal olefin comprises a step of isomerizing an ?-olefin having from 16 to 18 carbon atoms by passing through a zeolite catalyst bed, wherein the ?-olefin having from 16 to 18 carbon atoms is circulated through and brought into contact with the zeolite catalyst bed before starting the isomerization reaction.Type: GrantFiled: December 28, 2005Date of Patent: June 7, 2011Assignee: Idemitsu Kosan Co., Ltd.Inventors: Tetsuya Saruwatari, Hideki Yamane
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Patent number: 7655827Abstract: A process for selectively making 2-alkenes from a NAO using a mesoporous catalyst that has been surface modified with a Brönsted acid compound. The Brönsted acid compound has a reactive silane connector, an organic linking group, and a Brönsted acid group. The mesoporous catalyst has an average pore diameter in a range of about 12 to about 100 Angstroms and a surface area of between about 400 to about 1400 m2/gram.Type: GrantFiled: May 16, 2006Date of Patent: February 2, 2010Assignee: Chevron Phillips Chemical Company LPInventors: Ta Yen Ching, Jeffery Gee, Ruthann M Hickox
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Patent number: 7488860Abstract: An exo-tetrahydrodicyclopentadiene is produced from endo-tetrahydrodicyclopentadiene through isomerization reaction. An acidic ionic liquid is used in the isomerization. The isomerization of endo-tetrahydrodicyclopentadiene gives a reaction conversion and a selectivity both higher than 99%. Besides, the ionic liquid used is environmental-friendly and recyclable.Type: GrantFiled: September 13, 2006Date of Patent: February 10, 2009Assignee: Chinese Petroleum Corp.Inventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
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Patent number: 7355087Abstract: A catalytic distillation process for isomerizing and separating 1-alkenes from a mixed alkene stream. The process comprises contacting a mixed alkene stream comprising the 1-alkene and homologs thereof with a supported isomerization catalyst under isomerization/distillation conditions effective to convert at least a portion of the homologs to the 1-alkene, the isomerization/distillation conditions also being effective to produce a distillation overhead comprising a sufficient portion of the 1-alkene to drive isomerization of the homologs to the 1-alkene while maintaining the mixed alkene stream at least partially in liquid phase. The isomerization/distillation conditions are effective to recover a quantity of 1-alkene greater than an equilibrium quantity of 1-alkene recovered under isomerization conditions alone.Type: GrantFiled: October 1, 2004Date of Patent: April 8, 2008Assignee: Shell Oil CompanyInventors: Manuel Luis Cano, David Morris Hamilton, Jr., Terry Blane Thomason
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Patent number: 7271308Abstract: The present invention relates to embodiments for a process for the isomerization of at least one alpha olefin to an internal olefin via a multi-step process resulting in a mixture comprising alkene isomers and a low level of oligomers. According to the present invention an alkylaluminum compound is used in combination with the Group VIII transition metal salt for interaction with the latter, and thereby generating catalytically active species for the isomerization of 1-alkenes to internal alkenes, wherein this mixture is subsequently combined with an acid washed clay.Type: GrantFiled: October 19, 2004Date of Patent: September 18, 2007Assignee: Hercules IncorporatedInventor: Jian Jian Zhang
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Patent number: 7256152Abstract: A composition defined: either as comprising at least one Broensted acid, designated HB, dissolved in a liquid medium with an ionic nature of general formula Q+A?, in which Q+ represents an organic cation and A? represents an anion that is different from B, or as resulting from dissolving at least one Broensted acid, designated HB, in a non-aqueous liquid medium with an ionic nature of general formula Q+A?, in which Q+ represents an organic cation and A? represents an anion that is identical to the anion B, can be used as a catalyst and solvent in acid catalysis processes, in particular in the alkylation of aromatic hydrocarbons, the oligomerization of olefins, the dimerization of isobutene, the alkylation of olefins by isoparaffins, the isomerization of n-paraffins into isoparaffins, the isomerization of n-olefins into iso-olefins, the isomerization of the double bond of an olefin and the purification of an olefin mixture that contains branched alpha olefins as impurities.Type: GrantFiled: September 3, 2002Date of Patent: August 14, 2007Assignee: Institut Francais du PetroleInventors: Helene Olivier-Bourbigou, Dominique Commereuc, Olivia Martin, Lionel Magna, Emmanuel Pellier
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Patent number: 7151199Abstract: Hydrocarbon or oxygenate conversion process in which a feedstock is contacted with a non zeolitic molecular sieve which has been treated to remove most, if not all, of the halogen contained in the catalyst. The halogen may be removed by one of several methods. One method includes heating the catalyst in a low moisture environment, followed by contacting the heated catalyst with air and/or steam. Another method includes steam-treating the catalyst at a temperature from 400° C. to 1000° C. The hydrocarbon or oxygenate conversion processes include the conversion of oxygenates to olefins, the conversion of oxygenates and ammonia to alkylamines, the conversion of oxygenates and aromatic compounds to alkylated aromatic compounds, cracking and dewaxing.Type: GrantFiled: June 10, 2002Date of Patent: December 19, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
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Patent number: 6841713Abstract: 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: GrantFiled: February 6, 2001Date of Patent: January 11, 2005Assignee: Idemitsu Kosan Co., Ltd.Inventors: Toshiyuki Tsubouchi, Yukio Yoshida, Motohisa Ido, Masahiro Katayama
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Patent number: 6768038Abstract: A method for making alpha olefins from internal olefins using catalytic distillation techniques and an olefin double bond isomerization catalyst, and separately recovering said alpha olefins.Type: GrantFiled: December 20, 2002Date of Patent: July 27, 2004Assignee: Equistar Chemicals, LPInventor: Donald H. Powers
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Patent number: 6639118Abstract: Process technology for selectively isomerizing vinylidene olefin to tri-substituted olefin is described. The vinylidene olefin, normally in admixture with other types of olefins, especially linear 1-olefins, is treated with anhydrous hydrogen bromide under anhydrous conditions and in the absence of molecular oxygen and free radical initiator. The contacting period, which can be a matter of minutes, is sufficient to selectively isomerize the vinylidene olefin to tri-substituted olefin. If the process is conducted properly, little if any hydrobromination occurs.Type: GrantFiled: October 11, 2002Date of Patent: October 28, 2003Inventors: Bonnie G. McKinnie, J. Todd Aplin, Robert U. Lyons, Clinton R. Parham
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Patent number: 6593505Abstract: A catalyst comprising A) a stationary acid component selected from the group consisting of a perfluorinated ion exchange polymer on an inert support, a silane modified perfluorosulfonic acid, and a sulfated metal oxide; and B) a mobile acid component selected from the group consisting of chlorosulfonic acid, fluorosulfonic acid, a fluorinated monosulfonic acid, a fluorinated sulfonimide, a fluorinated disulfonic acid, and an adjunct acid mixture is disclosed.Type: GrantFiled: January 13, 2003Date of Patent: July 15, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark A. Harmer, Eugene F. Hartstein
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Patent number: 6281400Abstract: The present invention relates to a process for preparing a microcomposite comprising a highly fluorinated ion-exchange polymer containing pendant sulfonate functional groups, said polymer existing as aggregated particles entrapped within and dispersed throughout a network of silica. Due to their high surface area and acid functionality, these microcomposites possess wide utility as improved solid acid catalysts, particularly in the substitution of aromatic compounds, in the decomposition of hydroperoxides, and in the isomerization of olefins.Type: GrantFiled: January 14, 2000Date of Patent: August 28, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 5990368Abstract: Providing an isomerization process which can isomerize allenes to alkynes less expensively and stably is an assignment to be solved by the present invention and given thereto. The present invention is an isomerization process including the step of reacting an allene-lype hydrocarbon compound (R.sub.1 R.sub.2 C.dbd.C.dbd.CR.sub.3 R.sub.4) in the presence of alkaline-earth metal hydride working as an isomerization catalyst, thereby isomerizing the allene-type hydrocarbon compound to an alkyne-type hydrocarbon compound (R.sub.1 C.ident.C--CR.sub.2 R.sub.3 R.sub.4).Type: GrantFiled: July 7, 1998Date of Patent: November 23, 1999Assignee: Kabushiki Kaisha Toyota Chuo KenkyushoInventors: Mitsuru Nakano, Bruce M. Novak
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Patent number: 5969205Abstract: C.sub.4 -C.sub.6 -alkenes having an internal double bond can be produced by hydroisomerization of C.sub.4 -C.sub.6 -alkenes having a terminal double bond in the presence of H.sub.2 on a catalyst having a content of a noble metal of group VIII of the Periodic Table of the Elements (Mendeleev), if C.sub.4 -C.sub.6 -alkenes having a terminal double bond are fed into a hydroisomerization reactor after preheating, as such or in a mixture with other hydrocarbons, and the reaction product is divided into a work-up stream and a recycle stream. The recycle stream is recycled to the inlet of the hydroisomerization reactor and is used there as feed together with the C.sub.4 -C.sub.6 -alkenes having a terminal double bond or with the hydrocarbon stream comprising the C.sub.4 -C.sub.6 -alkenes having a terminal double bond and with the H.sub.2.Type: GrantFiled: August 21, 1998Date of Patent: October 19, 1999Assignee: EC Erdolchemie GmbHInventors: Arnd Stuwe, Jorg-Uwe Michel, Matthias Baum, Franz Kaledat
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Patent number: 5948946Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using a sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity. Isomerization of terminal olefins is possible with such porous microcomposites.Type: GrantFiled: July 23, 1998Date of Patent: September 7, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 5849974Abstract: Described is a process for isomerizing .alpha.-olefin to produce olefinic oil having a viscosity at 100.degree. C. of no more than about 1.6 cSt, a viscosity at 40.degree. C. of no more than about 3.8 cSt, and a pour point of 0.degree. C. or lower, preferably -10.degree. C. or lower. The process comprises contacting the .alpha.-olefin having from about 14 to about 20 carbon atoms with a catalytic quantity of nonmetallic sulfonic or perfluorosulfonic acid resin catalyst under identified isomerization conditions, thereby producing deep internal olefin having the desired combination of physical properties.Type: GrantFiled: January 28, 1997Date of Patent: December 15, 1998Assignee: Amoco CorporationInventors: Michel Clarembeau, Peter Steylaerts
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Patent number: 5780702Abstract: A catalytic composition comprises at least one quaternary ammonium and/or phosphonium salt in which the anion is preferably selected from the group formed by tetrafluoroborate, tetrachloroborate, hexafluorophosphate, hexafluoroantimonate, hexafluoroarsenate, trifluorosulphonate, fluorosulphonate, tetrachloroaluminate, dichlorocuprate, and trichlorozincate, and at least one complex of a transition metal from groups 8, 9 and 10, i.e., iron, ruthenium, cobalt, rhodium, iridium, nickel, palladium and platinum, is for the displacement of the double bond in olefins.Type: GrantFiled: June 17, 1996Date of Patent: July 14, 1998Assignee: Institut Francais du PetroleInventors: Yves Chauvin, Lothar Mussmann, Helene Olivier
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Patent number: 5648583Abstract: Exo-isomers of polyalkylcyclopentadienes are converted to endo-isomers by contacting the exo-isomers with an acid such as aqueous HCl.Type: GrantFiled: April 27, 1995Date of Patent: July 15, 1997Assignee: Albemarle CorporationInventors: John Y. Lee, Meng-Sheng Ao, Stephen E. Belmont, Lawrence H. Shepherd, Jr.
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Patent number: 5191145Abstract: Linear 1-olefins are continuously prepared from internal olevins by (i) continuously feeding internal olefin, isomerization catalyst and tri-lower alkyl aluminum to a reaction zone so as to cause the internal olefin to isomerize to 1-olefins which displace the lower alkyl groups to form a trialkyl aluminum compound in which at least one of the alkyl groups is a linear alkyl derived from the 1-olefin, (ii) continuously removing trialkylaluminum compound from the reaction zone and, thereafter, (iii) reacting the trialkyl aluminum compound with a 1-olefin so as to displace the linear alkyl from the trialkyl aluminum compound, thereby forming a linear 1-olefin product which is substantially free of internal olefins.Type: GrantFiled: August 2, 1991Date of Patent: March 2, 1993Assignee: Ethyl CorporationInventors: Robert H. Allen, John N. Hu, Ronny W. Lin, Andrew D. Overstreet
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Patent number: 5124465Abstract: Linear 1-olefins are prepared from internal olefins by (i) reacting them in the presence of an isomerization catalyst and a tri-lower alkyl aluminum so as to cause the internal olefin to isomerize to 1-olefins which displace the lower alkyl groups to form a trialkyl aluminum compound in which at least one of the alkyl groups is a linear alkyl derived from the 1-olefin, and, thereafter, (ii) reacting the trialkyl aluminum compound with a 1-olefin so as to displace the linear alkyl from the trialkyl aluminum compound, thereby forming a linear 1-olefin product which is substantially free of internal olefins.Type: GrantFiled: March 25, 1991Date of Patent: June 23, 1992Assignee: Ethyl CorporationInventors: Robert H. Allen, Keith G. Anderson, Steven P. Diefenbach, Ronny W. Lin, Larry H. Nemec, Andrew D. Overstreet, Gene C. Robinson
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Patent number: 5073663Abstract: A method for increasing the ratio of 2-methyl-2-butene (2MB2) to 2-methyl-1-butene (2MB1) in isoamylenes involves fractionating a feedstream containing tertiary amyl methyl ether (TAME) and isoamylenes including 2MB2 and 2MB1 in a ratio of about 2:1 to effect a separation between an overhead hydrocarbon fraction of isoamylenes including 2MB2 and 2MB1 in a ratio of about 1:1, a bottoms fraction including TAME, and a sidestream hydrocarbon fraction consisting essentially of isoamylenes including 2MB2 and 2MB1 in a ratio of about 6 to 12:1, recovering the sidestream hydrocarbon fraction, and recycling the overhead hydrocarbon fraction of isoamylenes to form a mixture which is subsequently reacted to form the feedstream. Prior to fractionation, the feedstream is formed by passing isoamylene, and optionally TAME, in a vapor phase over an ether cracking catalyst which isomerizes isoamylene and converts 2MB1 to 2MB2, i.e., the feedstream for fractionating, which contains 2MB2 and 2MB1 in a ratio of 2 to 5:1.Type: GrantFiled: January 31, 1990Date of Patent: December 17, 1991Assignee: Exxon Chemical Patents Inc.Inventors: Gustavo Cerri, Robert C. Michaelson
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Patent number: 5012025Abstract: A catalyst for promoting the molecular restructuring of the components of hydrocarbons to form desired products. The catalyst comprises copper salts, copper acetate being particularly preferred, in combination with anhydrous aluminum chloride. The catalyst can be used with either gaseous hydrocarbon raw materials such as natural gas, refinery gas, biomass decomposition gases, and similar materials, or with solids, meltable solids, or liquid hydrocarbon-containing raw materials including tar sands, oil shale, waxes, asphaltic compositions and the like. In the case of gaseous raw materials, the gases are preferably brought into contact with the copper salt coated on a catalyst support such as refractory alumina, in the presence of anhydrous aluminum chloride, which can be in vaporous form, in a continuous process.Type: GrantFiled: August 23, 1989Date of Patent: April 30, 1991Inventor: Viswanatha Sankaran
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Patent number: 4910355Abstract: Olefin oligomers having a lower pour point are obtained by forming a mixture of C.sub.8-18 olefins containing 50-90 weight percent .alpha.-olefins and 10-50 weight percent internal olefins and oligomerizing this mixture using a Friedel Crafts catalyst (e.g. BF.sub.3) and a promoter (e.g. n-butanol). The mixture of olefins can be formed from .alpha.-olefins (e.g. 1-decene) by subjecting the .alpha.-olefins to isomerization until 10-50 weight percent of the olefins are internal olefins.Type: GrantFiled: November 2, 1988Date of Patent: March 20, 1990Assignee: Ethyl CorporationInventors: Ronald L. Shubkin, Gerhard O. Kuehnhanss
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Patent number: 4778943Abstract: A process for the skeletal isomerization of olefins wherein the olefins are contacted with a catalyst comprising at least one alkaline earth oxide which has been treated with a halogen compound.Type: GrantFiled: October 24, 1985Date of Patent: October 18, 1988Assignee: Atlantic Richfield CompanyInventor: Hsiang-ning Sun
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Patent number: 4513157Abstract: In the isomerization of isolated double bonds to conjugated double bonds in optionally substituted cyclooctadienes, the isomerization catalyst comprises: (a) a transition metal compound of the formula Me(OR.sup.1).sub.4, wherein Me is Ti, Zr, or Hf, and R.sup.1 is C.sub.1-4 alkyl, and (b) an organoaluminum compound of the general formula AlR.sup.2.sub.3-n X.sub.n, wherein R.sup.2 is C.sub.1-4 alkyl, n is 0, 1, 2, or a fraction between 1 and 2, and X is halogen or, if n is 1, also hydrogen; the molar ratio of (a):(b) being in the range from 0.1 to 1:1, the catalyst having prolonged activity and the isomerization being conducted at a temperature of 50.degree.-200.degree. C.Type: GrantFiled: June 22, 1984Date of Patent: April 23, 1985Assignee: Chemische Werke Huels, AGInventors: Peter Hanssle, Wolfgang Zaar
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Patent number: 4405500Abstract: n-Alkenes can be converted catalytically into isoalkenes, when a mixture containing at least one n-alkene and hydrogen is brought into contact at a temperature of 400.degree. to 600.degree. C. and a residence time of 0.2 to 20 seconds with an Al.sub.2 O.sub.3 or SiO.sub.2 catalyst which is specifically activated and is promoted with halogen compounds of elements of the third to fifth main groups and second to eighth sub-groups of the periodic system and/or hydrohalic acids. The specific activation comprises calcining, before the promotion process, an aluminum hydroxide or aluminum oxide hydrate or a silica gel having a content of volatile ammonium salts to give Al.sub.2 O.sub.3 or SiO.sub.2, with expulsion of these volatile ammonium salts. For the conversion of the n-alkenes, the catalyst can be employed in a fixed or a mobilized catalyst bed.Type: GrantFiled: December 2, 1981Date of Patent: September 20, 1983Assignee: EC Erdolchemie GmbHInventors: Hans J. Muller, Helmar Honig, Werner Horlitz
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Patent number: 4367362Abstract: A process for the catalytic skeleton isomerization of n-alkenes to isoalkenes comprises contacting the n-alkene with a fluorinated aluminum oxide as the catalyst at temperatures of 250.degree.-550.degree. C., in the presence of 0.5-150% by weight of water, based on the weight of the alkene employed and replenishing the fluorine discharged from the catalyst in metered amounts, continuously or discontinuously, using, e.g., a volatile fluorine compound. The catalyst, partially deactivated by coking, is regenerated by burning it off with an oxygen-containing gas in the presence of steam.Type: GrantFiled: January 12, 1981Date of Patent: January 4, 1983Assignee: Chemische Werke Huels, AktiengesellschaftInventors: Gerhard Franz, Friedrich Heinrich, Hans-Josef Ratajczak
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Patent number: 4333856Abstract: Isomerizable hydrocarbons are isomerized using a catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed rhenium carbonyl component with a porous carrier material containing a uniform dispersion of catalytically effective amounts of a platinum group component, which is maintained in the elemental metallic state during the incorporation and pyrolysis of the rhenium carbonyl component, of a tin component, and of a halogen component and from about 1 to about 100 weight percent of a Friedel-Crafts metal halide calculated on a Friedel-Crafts metal halide-free basis.Type: GrantFiled: December 3, 1980Date of Patent: June 8, 1982Assignee: UOP Inc.Inventor: George J. Antos
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Patent number: 4227993Abstract: Catalysts particularly useful for hydroreforming and isomerization of hydrocarbons formed of a refractory mineral oxide carrier having a halogen in combined form and the following metals in free or combined state:(a) A metal from the platinum group (0.02 to 2%);(b) tin (0.02 to 2%); and(c) at least one metal selected from the group of scandium, yttrium, thorium, uranium, and the rare earths metals (0.01 to 5%)--said percentages being based upon the total weight of the catalyst, said catalyst preferably having platinum and chlorine. Also the use of said catalyst in the aforementioned hydrotreatments.Type: GrantFiled: March 6, 1979Date of Patent: October 14, 1980Assignee: Compagnie Francaise de RaffinageInventors: Philippe Engelhard, Georges Szabo, Joseph E. Weisang
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Patent number: 4221742Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: December 29, 1977Date of Patent: September 9, 1980Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia U. Din
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Patent number: 4213849Abstract: The improvement of the preferred Pt-Sn on alumina bimetallic catalyst (and similar catalysts) for hydrotreatment of hydrocarbons, comprising the catalyst further containing silicon in combined form.Type: GrantFiled: April 9, 1979Date of Patent: July 22, 1980Assignee: Compagnie Francaise de RaffinageInventors: Philippe Engelhard, Michel Legendre, Guy Paris, Georges Szabo