Preparing Utilizing Plural Diverse Reactions In Separate Zones Patents (Class 570/241)
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Patent number: 10329226Abstract: The present invention provides processes for the production of chlorinated methanes via the direct chlorination of methane. The processes include a dehydrochlorination and/or chlorination step that converts up to 100% of the higher chlorinated alkanes in a process stream from the methane chlorination reaction into more highly chlorinated alkanes. These more highly chlorinated alkanes can be easily removed from the process stream. The use of a cost effective feedstream of crude methane is thus rendered possible, without additional capital expenditure for the sophisticated separation equipment required to separate ethane and other hydrocarbon components from the methane feed.Type: GrantFiled: September 22, 2016Date of Patent: June 25, 2019Assignee: Blue Cube IP LLCInventors: John D. Myers, Matthew L. Grandbois
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Publication number: 20150038750Abstract: There are provided methods and systems for an electrochemical cell including an anode and a cathode where the anode is contacted with a metal ion that converts the metal ion from a lower oxidation state to a higher oxidation state. The metal ion in the higher oxidation state is reacted with an unsaturated hydrocarbon and/or a saturated hydrocarbon to form products. Separation and/or purification of the products as well as of the metal ions in the lower oxidation state and the higher oxidation state, is provided herein.Type: ApplicationFiled: July 30, 2014Publication date: February 5, 2015Inventors: Michael Joseph Weiss, Ryan J Gilliam, Kyle Self, Gal Mariansky, Margarete K Leclerc, Riyaz Mohammed Shipchandler, Jacob Nagar
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Publication number: 20130046121Abstract: Process and systems for converting lower molecular weight alkanes to higher molecular weight hydrocarbons that include recovery of residual halogenated hydrocarbons (e.g., CH3Br) from higher molecular weight hydrocarbon products.Type: ApplicationFiled: August 18, 2011Publication date: February 21, 2013Applicant: MARATHON GTF TECHNOLOGY, LTD.Inventors: Sabah A. Kurukchi, Yijun Liu, Anand Moodley
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Publication number: 20120065412Abstract: The present invention relates to a process for producing hydrocarbons from methane, which comprises, in a first stage (i), reacting methane to form ethylene and, in a later stage (ii), reacting the product mixture obtained in stage (i) which comprises ethylene and methane to give higher-value hydrocarbons. In addition, the present invention relates to a plant for producing hydrocarbons from methane in which, in a single plant strand, a plurality of plant units are arranged successively in series comprising: a first reactor A for carrying out a conversion from methane to ethylene a second reactor B for carrying out a conversion from ethylene to higher-value hydrocarbons.Type: ApplicationFiled: May 10, 2010Publication date: March 15, 2012Applicant: BASF SEInventors: Radwan Abdallah, Torsten Mäurer, Gerhard Theis
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Publication number: 20090216055Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride ethylene, and chlorine.Type: ApplicationFiled: December 17, 2008Publication date: August 27, 2009Inventors: Richard L. Wilson, Rodney D. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
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Patent number: 7335806Abstract: Describes an integrated process for preparing 1,2-dichloroethylenes. In the described process organic feed material, e.g., C2-C4 aliphatic hydrocarbons and/or chlorinated derivatives of such aliphatic hydrocarbons, is introduced into a first reaction zone 10, e.g., a chlorination zone such as an oxychlorination zone, or a thermal cracking zone; first product effluent from the first reaction zone is forwarded to a second reaction zone 9; trichloroethane is introduced into the second reaction zone and into heat exchange contact with the first product effluent from the first reaction zone, which has a heat content sufficient to cause thermal dehydrochlorination of trichloroethane in the second reaction zone; and second product effluent is removed from the second reaction zone. 1,2-dichloroethylene is recovered by conventional distillation recovery methods from the second product effluent.Type: GrantFiled: February 14, 2006Date of Patent: February 26, 2008Assignee: PPG Industries Ohio, Inc.Inventor: Johnathan W. Scroggins
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Patent number: 6673539Abstract: A method of increasing the fluorous nature of a compound includes the step of reacting the compound with at least one second compound having the formula: wherein Rf is a fluorous group and m is 0, 1 or 2.Type: GrantFiled: May 31, 2000Date of Patent: January 6, 2004Assignee: University of PittsburghInventors: Peter Wipf, Jon Reeves, Stephan Roever
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Patent number: 6156896Abstract: The present invention provides several methods of synthesis and separation in which organic/fluorous phase separation techniques are used to effect separations. The present invention also provides novel compositions of matter comprising fluorous Si, Sn and Ge compounds.Type: GrantFiled: May 15, 1998Date of Patent: December 5, 2000Assignee: University of PittsburghInventors: Dennis P. Curran, Sabine Hadida Ruah, Masahide Hoshino, Armido Studer, Peter Wipf, Patrick Jeger, Sun-Young Kim, Rafael Ferritto
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Patent number: 5981815Abstract: The invention relates to a process for the preparation of .alpha.,.omega.-bromochloroalkanes. A cyclic ether is hydrobrominated and then the phase obtained is reacted, without any prior purification or separation, with thionyl chloride.Type: GrantFiled: May 5, 1998Date of Patent: November 9, 1999Assignee: ELF Atochem, S.A.Inventors: Gilles Drivon, Christophe Ruppin
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Patent number: 5973216Abstract: A method for producing bromomethylcyclopropane is provided, comprising reacting an organic sulfonyl halide with cyclopropylmethanol in the presence of a tertiary amine in a non-protic solvent, to generate cyclopropylmethyl organic sulfonate, and reacting the resulting cyclopropylmethyl organic sulfonate with an alkali metal bromide and/or a quaternary ammonium bromide in a non-protic polar solvent.Type: GrantFiled: February 13, 1998Date of Patent: October 26, 1999Assignee: Kuraray Co., Ltd.Inventors: Toshimichi Mitani, Tatsuhiko Hayashibara, Manzo Shiono
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Patent number: 5777121Abstract: The present invention provides a method for carrying out a chemical reaction comprising the steps of forming an organic/fluorous solubilizing liquid phase comprising a solvent system. The solvent system is selected or adapted to substantially solubilize a fluorous reaction component or components (that is, a fluorous reagent, a fluorous catalyst and/or a fluorous reactant). The "fluorous reaction component" is functionalized to comprise at least one fluorous moiety having the formula -(R).sub.d (Rf).sub.e. (Rf).sub.e is at least one fluorous group and e is a whole number. (R).sub.d is an organic (for example, hydrocarbon) spacer group, which may be present or absent, and d is an integer equal to at least zero. The solvent system is also adapted to substantially solubilize an organic reaction component or components. After the reaction occurs in the organic/fluorous solubilizing liquid phase, a phase separation into at least a fluorous phase and an organic phase is effected.Type: GrantFiled: June 28, 1996Date of Patent: July 7, 1998Assignee: University of PittsburghInventors: Dennis P. Curran, Sabine Hadida, Masahide Hoshino, Armido Studer
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Patent number: 5723704Abstract: Process for the preparation of alkyl chlorides, characterized in that:a) in a first stage a primary mono- or polyhydric alcohol, which has a C.sub.4 -C.sub.30 carbon chain which is saturated, substituted or otherwise by one or more chlorine atoms and branched or otherwise and which may comprise one or more C.sub.5 -C.sub.7 cycloalkyl groups, is reacted with gaseous hydrochloric acid in the absence of catalyst and at a temperature of between 80.degree. C. and 170.degree. C., until the degree of conversion of the alcohol functional groups is equal to or between 60 and 95 mol %, andb) in a second stage phosgene and a catalyst are introduced into the reaction mixture, the catalyst being chosen from the group consisting of hexaalkylguanidinium halides and their hydrohalides, quaternary ammonium halides, quaternary phosphonium halites, pyridine and pyridines substituted by one or more C.sub.1 -C.sub.6 alkyl groups, at a temperature of between 80.degree. C. and 160.degree.C.Type: GrantFiled: January 3, 1997Date of Patent: March 3, 1998Assignee: Societe Nationale des Poudres et ExplosifsInventors: Herve Demail, Jean-Claude Schweickert, Pierre Le Gars
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Patent number: 5099084Abstract: A process is provided for the chlorination of methane using hydrogen chloride as a source of chlorine. The process includes reaction steps operated in tandem in separate zones first comprising the reaction of perchloroethylene with hydrogen chloride and oxygen in the presence of an oxychlorination catalyst to give hexachloroethane and water, and second comprising the vapor phase reaction of hexachloroethane with methane feedstock to produce chlorinated methane, perchloroethylene and hydrogen chloride.Type: GrantFiled: January 13, 1989Date of Patent: March 24, 1992Inventor: John E. Stauffer
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Patent number: 5097083Abstract: A process is provided for the chlorination of ethane using hydrogen chloride, chlorine or mixtures as the chlorinating agent. The process includes reaction steps operated in tandem in separate zones first comprising the reaction of perchloroethylene with hydrogen chloride and oxygen in the presence of an oxychlorination catalyst to give hexachloroethane and water, and second comprising the vapor phase reaction of hexachloroethane with ethane feedstock to produce chlorinated ethanes, chlorinated ethylenes, and hydrogen chloride.Type: GrantFiled: January 13, 1989Date of Patent: March 17, 1992Inventor: John E. Stauffer
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Patent number: 4990696Abstract: Perchloroethylene is oxychlorinated to provide hexachloroethane which is reacted with methane to produce methyl chloride which is hydrolyzed to form methyl alcohol product and hydrogen chloride which is recycled to the oxychlorination step.Type: GrantFiled: May 29, 1990Date of Patent: February 5, 1991Inventor: John E. Stauffer
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Patent number: 4849562Abstract: The oxychlorination process for producing ethylene dichloride is carried out by reacting ethylene with hydrogen chloride and oxygen in an oxychlorination reactor. Thereby, ethyl chloride and perhaps vinyl chloride are produced as by-products. The effluent from the reactor is at least fractionated into an ethylene dichloride-rich fraction (I) and an ethyl chloride-rich fraction (II) so that fraction (I) contains less than 50 percent of the total weight of ethyl chloride produced in step (a) and the sum of the weight of ethylene dichloride and vinyl chloride in fraction (II) is less than 30 percent of the weight of ethyl chloride in fraction (II). The ethyl chloride-rich fraction (II) is subjected to a cracking reaction in the presence or absence of an inert diluent wherein ethyl chloride is converted into ethylene and hydrogen chloride in the presence of a catalyst.Type: GrantFiled: August 26, 1988Date of Patent: July 18, 1989Assignee: The Dow Chemical CompanyInventors: Christoph Buhs, Eberhard Dreher, Garnet E. McConchie
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Patent number: 4788358Abstract: A process for the manufacture of 1,2-dichloroethane from ethylene by reaction with hydrogen chloride and inert gases containing oxygen, and also by reaction with chlorine, is described. The two chlorination reactions are carried out successively at 180.degree. to 360.degree. C. and under a pressure of 0.09 to 1.1 MPa in a common reaction space containing fluidized catalyst particles. A stoichiometric excess of ethylene is employed for the first chlorination reaction. The heat formed in the reaction space is removed by indirect cooling. The process is simple in terms of apparatus and permits a better re-use of the total heat of reaction of the chlorination of ethylene.Type: GrantFiled: August 5, 1985Date of Patent: November 29, 1988Assignee: Bayer AktiengesellschaftInventors: Josef Riedl, Wenzel Kuhn, Peter Widmann
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Patent number: 4760207Abstract: In a process for producing 1,2-dichloroethane or ethylene dichloride ("EDC") in a high temperature direct chlorination ("HTDC") reactor in which ethylene is reacted with wet chlorine having a water content more than 100 ppm but no more than 1% by wt of the chlorine, the water leaves the reactor with the EDC product draw-off, either in the vapor overhead (if the HTDC is a boiling reactor), or, as a liquid sidestream (if the HTDC is a non-boiling reactor). In a subsequent step, the EDC draw-off is distilled in a product distillation column in which the water leaves in the overhead which is condensed to remove condensables in a first stage, and vent a non-condensable vent streams. The vent stream is corrosive due to the presence of minor amounts of chlorine, HCl and water, along with oxygen which is injected into the HTDC to improve selectivity of the reaction. The vent gases from the first stage are further cooled to a temperature in the range from about -30.degree. C. to about 0.degree. C.Type: GrantFiled: September 18, 1986Date of Patent: July 26, 1988Assignee: B.F. Goodrich CompanyInventor: Joseph A. Cowfer
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Patent number: 4754088Abstract: In a process for preparation of 1,2-dichloroethane by chlorination of ethylene-containing reaction vent gases from the oxychlorination of ethylene in the presence of a catalyst carrier impregnated with metal compounds wherein the waste from the oxychlorination stage are chlorinated, the improvement comprising preheating the ethylene-containing waste gases to at least 50.degree. C. and then chlorinating the ethylene at 100.degree. to 300.degree. C. at a pressure of 1 to 7 bar with a space velocity of 100 to 5000 h.sup.-1 related to standard conditions in the presence of at least one metal compound selected from the group consisting of chlorides and oxides of manganese, nickel and cobalt supported on a catalyst carrier with reduced formation of oxychlorinated by-products.Type: GrantFiled: February 11, 1987Date of Patent: June 28, 1988Assignee: Wacker-Chemie GmbHInventors: Ludwig Schmidhammer, Peter Hirschmann, Herbert Patsch, Rudolf Strasser
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Patent number: 4746760Abstract: Process for functionalizing saturated hydrocarbons comprising:(a) reacting said saturated hydrocarbons of the formula:R.sub.1 Hwherein H represents a hydrogen atom; and R.sub.1 represents a saturated hydrocarbon radical, with a metal complex of the formula:CpRh[P(R.sub.2).sub.3 ]H.sub.2whereinCp represents a cyclopentadienyl or alkylcyclopentadienyl radical;Rh represents a rhodium atom;P represents a phosphorus atom;R.sub.2 represents a hydrocarbon radical;H represents a hydrogen atom,in the presence of ultraviolet radiation to form a hydridoalkyl complex of the formula:CpRh[P(R.sub.2).sub.3 ](R.sub.1)H(b) reacting said hydridoalkyl complex with an organic halogenating agent such as a tetrahalomethane or a haloform of the formulas:CX'X''X'''X'''' or CHX'X''X'''wherein X', X'', X'", X"" represent halogens selected from bromine, iodine or chlorine atom, at a temperature in the range of about -60.degree. to -17.degree. C. to form the corresponding haloalkyl complex of step (a) having the formula:CpRhPMe.sub.Type: GrantFiled: February 21, 1985Date of Patent: May 24, 1988Assignee: Chevron Research CompanyInventors: Robert G. Bergman, Andrew H. Janowicz, Roy A. Periana
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Patent number: 4668833Abstract: A process for hydrogenating acetylene in hydrogen chloride gas using the catalytic palladium supported on silicon carbide carrier whose iron content is specified to be not more than 1,000 ppm. The catalyst has the advantages of enhancing the conversion of acetylene into ethylene, improving the selectivity of ethylene, and retaining catalytic activity over a long time at a large space velocity. This process can be effectively applied to the hydrogenation of acetylene in hydrogen chloride gas separated from the thermally decomposed products of 1,2-dichloroethane which occurs in the production of vinyl chloride; namely, the hydrogen chloride gas that contains thus hydrogenated acetylene (ethylene) can be recycled in such an effective way that 1,2-dichloroethane can be produced economically.Type: GrantFiled: April 24, 1986Date of Patent: May 26, 1987Assignee: Kanegafuchi Chemical Industry Co., Ltd.Inventors: Hiroshi Ohshima, Osamu Kakimoto
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Patent number: 4590317Abstract: A process is disclosed for the economical operation of a commercial ethylene dichloride (EDC) cracking furnace which typically is prone to coking of the tubes through which the EDC is flowed. The EDC cracking furnace is found to be critically sensitive to the presence of trace amounts, 30 ppm or more of FeCl.sub.3 and/or 20 ppm or more of free chlorine, which cause coking of the tubes of the furnace. The coking of the tubes is minimized by maintaining less than 30 ppm by weight of FeCl.sub.3 or less than 20 ppm of free chlorine in the EDC feed to the EDC furnace. In the particular instance where EDC is produced at least in part in a high temperature direct chlorination ("boiling") reactor constructed from mild steel, this goal requires that the chlorine content of the effluent from the boiling reactor be controlled so as not to exceed 20 ppm. But this is to be done without using more than a 2% by weight excess of ethylene over the stoichiometric amount required to produce the EDC in the boiling reactor.Type: GrantFiled: August 6, 1984Date of Patent: May 20, 1986Assignee: The B. F. Goodrich CompanyInventor: John P. Lenczyk
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Patent number: 4547599Abstract: A trace amount of free chlorine, present along with comparable amounts of ethylene, oxygen and water vapor in the ethylene dichloride (EDC) effluent from a direct chlorination reactor, may be effectively scavenged by exposing the effluent to ultraviolet ("u-v") light having a wavelength less than about 4000.ANG. which is absorbed by the chlorine, but to which both ethylene and EDC are essentially transparent. In this process, contaminant chlorine in substantially pure (99..sup.+ %) EDC is catalytically activated and reacts with EDC to form an unwanted byproduct, namely 1,1,2-trichloroethane ("triane"). The process is effective in either the gaseous phase or the liquid phase.Type: GrantFiled: April 27, 1984Date of Patent: October 15, 1985Assignee: The B. F. Goodrich CompanyInventors: Wolfgang Schneider, John P. Lenczyk
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Patent number: 4518813Abstract: (2R,6R)-1-Chloro-2,6,10-trimethyl-undecane I, (R)-(+)-.beta.-chloro-isobutyric acid II, (S)-(+)-1-bromo-3-chloro-2-methylpropane IV and (2R)-(+)-1-chloro-2,6-dimethyl-heptane V are novel optically active units for the synthesis of the side chain of (R,R,R)-.alpha.-tocopherol. In the process according to the invention, the optically active C.sub.Type: GrantFiled: September 30, 1982Date of Patent: May 21, 1985Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Friedrich Vogel, Joachim Paust
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Patent number: 4511745Abstract: Process for functionalizing saturated hydrocarbons selectively in the terminal position comprising:(a) reacting said saturated hydrocarbons of the formula:RHwhere:H represents a hydrogen atom, andR represents a saturated hydrocarbon radical,with a metal complex of the formula:CpRhPMe.sub.3 H.sub.2where:Cp represents a pentamethylated cyclopentadienyl radical,Rh represents a rhodium atom,P represents a phosphorous atom,Me represents a methyl group,H represents a hydrogen atom,in the presence of ultraviolet radiation at a temperature maintained at about -60.degree. to -17.degree. C. to form a hydridoalkyl complex of the formula:CpRhPMe.sub.3 RH(b) reacting said hydridoalkyl complex with a haloform of the formula:CHX.sub.3where:X represents a bromine, iodine or chlorine atom,at a temperature in the range of about -60.degree. to -17.degree. C. to form the corresponding haloalkyl complex of step (a) having the formula:CpRhPMe.sub.3 RX; and,(c) reacting said haloalkyl complex formed in (b) with halogen (X.sub.Type: GrantFiled: June 12, 1984Date of Patent: April 16, 1985Assignee: The United States of America as represented by the United States Department of EnergyInventors: Robert G. Bergman, Andrew H. Janowicz, Roy A. Periana-Pillai
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Patent number: 4409198Abstract: Copper(II) chloride is prepared from copper(II) oxychloride in a nonpolar solvent, preferably during oxychlorination. As the source of hydrogen chloride, the hydrochlorides of certain tertiary amines having 12-40 carbon atoms in total are utilized. The amine contains at most one N-methyl group and its dissociation constant K.sub.a of the equilibrium reactionNR.sub.3 H.sup..sym. +H.sub.2 O.revreaction.NR.sub.3 +H.sub.3 O.sup..sym.is 10.sup.-3.5 to 10.sup.-8.5. Preferred tertiary amines are a trialkylamine of 15-36 carbon atoms; an N-alkylazacycloalkane of the formula ##STR1## wherein R is alkyl of 6-15 carbon atoms, 5.ltoreq.n.ltoreq.8, ALK represents one or more alkyl substituents, and the N-alkylazacycloalkane contains at least 15 carbon atoms; or an N,N-dialkylaniline wherein each alkyl group independently contains 6-12 carbon atoms and the benzene ring is optionally substituted by one or more alkyl groups of 1-3 carbon atoms each.Type: GrantFiled: August 4, 1982Date of Patent: October 11, 1983Assignee: Chemische Werke Huls, AGInventors: Alfred Coenen, Manfred Schroeder, Guenter Prominski
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Patent number: 4319062Abstract: An improved process for production of allyl chloride which comprises (1) thermally chlorinating propylene above 300.degree. C., but below that at which substantial carbon formation is effected, (2) separating the allyl chloride from its by-products, (3) subjecting the unsaturated compounds in said by-products to a low temperature chlorination, (4) separating the 1,2-dichloropropane from the products of said low temperature chlorination, and (5) passing said 1,2-dichloropropane to a cracking furnace. The effluent from the cracking furnace can be recycled to the allyl chloride finishing system by adding it to the high temperature propylene chlorination reactor effluent. Reaction temperatures are optimized to eliminate problems caused by carbon formation in the high temperature chlorination reactor, while overall yields of allyl chloride are increased and effluents which are ecologically and economically undesirable are reduced.Type: GrantFiled: April 17, 1978Date of Patent: March 9, 1982Assignee: The Dow Chemical CompanyInventors: Theodore S. Boozalis, John B. Ivy, Gordon G. Willis
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Patent number: 4271080Abstract: Tetrahydrofuran is prepared by reacting a 1,4-dihalobutane with water in the vapor phase in the presence of a catalytically effective amount of at least one solid acidic elemental oxide and/or solid acidic mixed elemental oxide, or acidic ion exchange resin which is stable under reaction conditions.Type: GrantFiled: June 16, 1980Date of Patent: June 2, 1981Assignee: National Distillers and Chemical Corp.Inventor: Jawad H. Murib
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Patent number: 4268697Abstract: A process for preparing primary substituted n-alkane compounds, comprising contacting the olefin product of an olefin metathesis reaction having an alpha-olefin as the reactant with a bis-cyclopentadienyl zirconium hydrohalide and, after contacting the product of the olefin-zirconium hydrohalide reaction with an electrophilic reagent, recovering said primary substituted n-alkane compound.Type: GrantFiled: June 21, 1979Date of Patent: May 19, 1981Assignee: The Procter & Gamble CompanyInventor: Thomas W. Gibson