By Alkyl Transfer, E.g., Disproportionation, Etc. Patents (Class 585/643)
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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: 7094898Abstract: A new class of compounds is disclosed that in preferred embodiments relate to Ru-based catalysts suitable for use in olefin metathesis reactions. Such compounds demonstrate high rates of catalytic turnover in comparison with other Ru catalysts known in the art. Moreover, the catalysts are highly stable, and readily suited to attachment to a solid support via the anionic ligands. The invention also pertains to methods of producing the catalysts, and their use in catalyzing olefin metathesis reactions.Type: GrantFiled: May 28, 2004Date of Patent: August 22, 2006Assignee: University of OttawaInventors: Deryn Elizabeth Fogg, Jay Christopher Conrad
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Patent number: 7041864Abstract: Ring opening cross metathesis of secondary non-cyclic hydrocarbons with cyclic unsaturated hydrocarbons having 8 carbon atoms or more to produce corresponding unsaturated product hydrocarbons having more than 8 carbon atoms.Type: GrantFiled: December 11, 2002Date of Patent: May 9, 2006Assignee: Shell Oil CompanyInventors: Howard Lam-ho Fong, Michael Wayne Potter, David Stephen Brown
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Patent number: 7041861Abstract: A process in which neohexene is produced by starting with butene in a distillation column reactor to produce a product containing ethylene, diisobutene, heavier oligomers. After separating these components, the separated diisobutene is further reacted with ethylene produced from the first step to produce neohexene.Type: GrantFiled: May 7, 2003Date of Patent: May 9, 2006Assignee: Catalytic Distillation TechnologiesInventor: Gary G. Podrebarac
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Patent number: 6977318Abstract: A method for forming propylene wherein ethylene is employed as a primary feed material in a combination of steps comprising dehydration, skeletal isomerization, and metathesis to form a versatile product mix that can contain one or more of propylene, gasoline, MTBE, and propylene oxide.Type: GrantFiled: May 4, 2004Date of Patent: December 20, 2005Assignee: Equistar Chemicals, LPInventor: Robert S. Bridges
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Patent number: 6967256Abstract: One aspect of the present invention relates to methods of preparing enedialkylidyne complexes, enediynes, and alkyne metathesis catalysts, as well as methods of catalyzing alkyne metathesis reactions. The present invention also relates to methods of activating enedialkylidyne complexes for metathesis. The present invention also relates to enedialkylidyne complexes.Type: GrantFiled: September 19, 2003Date of Patent: November 22, 2005Assignee: Massachusetts Institute of TechnologyInventors: Christopher C. Cummins, James M. Blackwell
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Patent number: 6906234Abstract: A continuous method and a heat pump device for enrichment of low-concentrated reaction mixtures resulting from the production of cycloalkanedienes by means of catalytic metathesis of cyclic aliphatic alkenes and cyclooligomers in organic reaction media with reduced energy consumption. Using the heat pump principle, liquid reaction mixtures with a content of at least 0.1 w/w % are enriched in an organic reaction medium to 30 to 50 w/w %. The organic reaction medium at temperature T1 is evaporated in an evaporator, the vapor is withdrawn and compressed to temperature T2 in a compressor, at a pressure difference of 0.25 to 1 bar. Compressed vapor of the reaction medium transfers heat energy obtained from electric energy in the heat exchanger of the evaporator to the organic reaction medium at temperature T1, and the temperature difference (T2?T1) does not exceed 12 K.Type: GrantFiled: July 30, 1999Date of Patent: June 14, 2005Assignee: Symrise GmbH & Co. KGInventors: Jürgen Braband, Peter Müller, Rüdiger Bernhardt, Andreas Otto
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Patent number: 6884917Abstract: A method for forming high purity 1-butene wherein a feed composed of pentenes and hexenes is subjected to metathesis with ethylene to form a mixture containing propylene, 1-butene, 2-butenes, pentenes, and hexenes, and high purity 1-butene is separately recovered from the mixture by simple distillation.Type: GrantFiled: May 18, 2004Date of Patent: April 26, 2005Assignee: Equistar Chemicals, LPInventor: Steven T. Coleman
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Patent number: 6881323Abstract: The present invention relates to new crystalline zeolite SSZ-54 prepared using a templating agent comprising N-isopropyl ethylenediamine, or a mixture of 1-N-isopropyl diethylenetriamine and isobutylamine, and processes employing SSZ-54 in a catalyst.Type: GrantFiled: June 28, 2002Date of Patent: April 19, 2005Assignee: Chevron U.S.A. Inc.Inventor: Stacey Zones
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Patent number: 6872862Abstract: A method for making propylene from alpha olefins, internal linear olefins and isoolefins wherein the alpha olefins are subjected to a combination of hydrogenation and double bond isomerization to form additional internal linear olefins, the internal linear olefins are separated from the isoolefins and disproportionated with ethylene to form a propylene product, while the thus separated isoolefins are subjected to skeletal isomerization to form yet additional internal linear olefins to be converted into yet additional propylene product.Type: GrantFiled: June 25, 2003Date of Patent: March 29, 2005Assignee: Equistar Chemicals, LPInventors: Robert S. Bridges, Donald H. Powers, Steven T. Coleman
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Patent number: 6852900Abstract: The present invention relates to a process for the metathesis reaction of unsaturated organic compounds.Type: GrantFiled: March 1, 2001Date of Patent: February 8, 2005Assignee: Merck Patent GmbHInventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
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Patent number: 6844479Abstract: A process for the alkylation of paraffins with olefins includes contacting the paraffin with the olefin under alkylation conditions with a zeolite having an AAI number of at least about 1.0. In a preferred process isobutane is alkylated with cis-2-butene to produce a high octane (RON) gasoline product containing trimethylpentane isomers.Type: GrantFiled: April 24, 2003Date of Patent: January 18, 2005Assignee: ABB Lummus Global Inc.Inventors: Chuen Y. Yeh, Xingtao Gao, Philip J. Angevine
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Publication number: 20040254414Abstract: A process for producing propylene is provided which includes directing an ethylene stream from an ethylene reaction zone to a propylene reaction zone; directing a butene stream to the propylene reaction zone; reacting the ethylene stream with the butene stream in the propylene reaction zone to produce a propylene reaction stream; and subjecting the propylene reaction stream to a recovery operation to recover propylene. A processes is also provided for producing an alkylaromatic by directing an ethylene stream from a propylene reaction zone to an alkylaromatic reaction zone; directing an aromatic stream to the alkylaromatic reaction zone; reacting the ethylene stream with the aromatic stream in the alkylaromatic reaction zone to produce an alkylaromatic reaction stream; and subjecting the alkylaromatic reaction stream to a recovery operation to recover alkylaromatics. A process for producing propylene and an alkylaromatic is also provided.Type: ApplicationFiled: June 11, 2003Publication date: December 16, 2004Inventors: James M. Hildreth, Kerman Nariman Dukandar, Ronald M. Venner
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Publication number: 20040220441Abstract: Process for preparing a compound having a nonaromatic C—C double or triple bond (compound A) from another compound or a mixture of other compounds having a nonaromatic C—C double or triple bond (compound B), which comprises bringing the compound (B) into contact with a heterogeneous catalyst comprising carbides or oxycarbides of a transition element at from 50 to 500° C.Type: ApplicationFiled: March 30, 2004Publication date: November 4, 2004Applicant: BASF AkiengesellschaftInventors: Markus Schubert, Till Gerlach, Michael Hesse, Juergen Stephan, Volker Bohm, Andreas Brodhagen, Frank Poplow
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Patent number: 6777582Abstract: A C3 to C6 hydrogen cut from a cracking unit is processed for the conversion of olefins to propylene and hexene via autometathesis. The autometathesis of a mixed normal butenes feed in the presence of a metathesis catalyst operates without any ethylene in the feed mix to the metathesis reactor. Some fraction of the 2-butene feed may be isomerized to 1-butene and the 1-butene formed plus the 1-butene in the feed react rapidly with the 2-butene to form propylene and 2-pentene. The feed to the reactor also includes the recycle of the 2-pentene formed in the reactor with unreacted butenes to simultaneously form additional propylene and hexene. In one embodiment, some or all of the 3-hexene formed in the reaction is isomerized to 1-hexene. In another embodiment, some portion of the 3-hexene produced in the main metathesis reaction is reacted with ethylene to produce 1-butene without the need for superfractionation.Type: GrantFiled: March 7, 2002Date of Patent: August 17, 2004Assignee: ABB Lummus Global Inc.Inventors: Robert J. Gartside, Marvin I. Greene, Quincy J. Jones
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Publication number: 20040138512Abstract: The invention relates to a method for the production of propene from a mixture (M1) essentially consisting of the following: ethylene (component E); hexenes (components H); optionally olefinic hydrocarbons (components K1a) different from ethylene and hexenes and optionally other inert hydrocarbons (components K1b). According to said method, the mixture (M1) is brought into contact with a metathesis catalyst at a temperature of 20 to 350° C., with the proviso that, as regards mixture (M1): the molar proportion of the sum consisting of 2-hexene and 3-hexene in components H is at least 4:1 to 99:1; the molar ratio between component E and the sum of components H and K1a is 1:1 to 100:1; the ratio between 2-hexenes and 3-hexenes is at least 2:1 as long as the 3-hexenes contained in the mixture are not simultaneously subjected to isomerization by means of which the proportion of 2-hexenes is correspondingly increased.Type: ApplicationFiled: October 9, 2003Publication date: July 15, 2004Inventors: Michael Roper, Jurgen Stephan, Gotz-Peter Schindler
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Publication number: 20040116763Abstract: Ring opening cross metathesis of secondary non-cyclic hydrocarbons with cyclic unsaturated hydrocarbons having 8 carbon atoms or more to produce corresponding unsaturated product hydrocarbons having more than 8 carbon atoms.Type: ApplicationFiled: December 11, 2002Publication date: June 17, 2004Inventors: Howard Lam-ho Fong, Michael Wayne Potter, David Stephen Brown
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Patent number: 6727396Abstract: Ethylene and hexene-1 are produced from butene-1 by metathesis of butene-1 and isomerization of the hexene-3 produced therein to hexene-1. The initial starting material is a mixed butene stream wherein butene-1 is isomerized to butene-2 with isobutylene being separated therefrom, followed by isomerization of butene-2 to butene-1, with the butene-1 being the feed to the metathesis.Type: GrantFiled: January 23, 2002Date of Patent: April 27, 2004Assignee: ABB Lummus Global, Inc.Inventor: Robert J. Gartside
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Publication number: 20040054241Abstract: A process for the targeted preparation of linear &agr;-olefins having from 6 to 20 carbon comprises:Type: ApplicationFiled: July 24, 2003Publication date: March 18, 2004Inventors: Heiko Maas, Dag Wiebelhaus, Jurgen Stephan, Rocco Paciello
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Publication number: 20040035751Abstract: The present invention relates to new mesoporous inorganic solids in the form of primary and/or secondary inorganic particles of D10≧1 &mgr;m and D50≧3 &mgr;m, preferably from D10≧2 &mgr;m and D50≧10 &mgr;m the size of which can go up to 10 mm, wherein the microporous volume (pores of size less than or equal to 2 &mgr;m) represents at most 10% of the total porous volume up to 300 nm.Type: ApplicationFiled: May 14, 2003Publication date: February 26, 2004Applicant: CECA, S.A.Inventor: Dominique Plee
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Patent number: 6660813Abstract: An in-situ method for performing organic metathesis polymer chemistry in the solid state includes the step of providing an organic monomer and a catalyst, the catalyst for driving a metathesis polymerization reaction of the monomer. The organic monomer can be provided as a liquid monomer. The reaction produces reaction products including a polymeric end product and at least one volatile reaction product. At least a portion of the volatile reaction product is removed during the reaction to favor formation of the reaction product. Significantly, the reaction is performed at a temperature being below an average melting point of the polymeric end product such that at least a portion of the reaction is performed in the solid phase.Type: GrantFiled: August 1, 2002Date of Patent: December 9, 2003Assignee: University of FloridaInventors: Kenneth B. Wagener, Stephen E. Lehman, Jr., Garrett W. Oakley, Jason A. Smith
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Publication number: 20030204124Abstract: The metathesis process is used: (A) for the production of propylene from the metathesis of 2-butene and ethylene wherein the propylene product is removed concurrently by fractional distillation by which the removal of the propylene product disturbs the equilibrium concentration and allows for higher conversions; (B) for the production of detergent range olefins from the metathesis of C15 and heavier olefins with C9 and lighter olefins wherein the detergent range olefin product is removed concurrently by fractional distillation in which the removal of the detergent range olefin product disturbs the equilibrium concentration and allows for higher conversions with less side reactions; (C) for the production of 2-methyl-2-butene and propylene from the metathesis of 2-butene and isobutylene wherein the propylene product and 2-methyl-2-butene product is removed concurrently by fractional distillation in which the removal of the product disturbs the equilibrium concentration and allows for higher conversions; and (DType: ApplicationFiled: May 7, 2003Publication date: October 30, 2003Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventor: Gary G. Podrebarac
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Publication number: 20030204123Abstract: The metathesis process is used: (A) for the production of propylene from the metathesis of 2-butene and ethylene wherein the propylene product is removed concurrently by fractional distillation by which the removal of the propylene product disturbs the equilibrium concentration and allows for higher conversions; (B) for the production of detergent range olefins from the metathesis of C15 and heavier olefins with C9 and lighter olefins wherein the detergent range olefin product is removed concurrently by fractional distillation in which the removal of the detergent range olefin product disturbs the equilibrium concentration and allows for higher conversions with less side reactions; (C) for the production of 2-methyl-2-butene and propylene from the metathesis of 2-butene and isobutylene wherein the propylene product and 2-methyl-2-butene product is removed concurrently by fractional distillation in which the removal of the product disturbs the equilibrium concentration and allows for higher conversions; and (DType: ApplicationFiled: May 7, 2003Publication date: October 30, 2003Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventor: Gary G. Podrebarac
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Patent number: 6639116Abstract: Novel condensation reactions used to produce 1,3-cyclohexadiene. Such a compound is an important precursor in the manufacture of high performance plastics, as one example, are provided. In the past, the production methods for such 1,3-cyclohexadiene required very complex reactions involving numerous process steps. Such a method has proven costly, difficult to properly monitor and control, and less than reliable to provide even low amounts of such a precursor compound. The inventive production methods thus permit a reduction in complexity and cost, and, with a single reaction step, facilitate quality measurements as to the product purity itself.Type: GrantFiled: March 15, 2002Date of Patent: October 28, 2003Assignee: Millken & CompanyInventors: John G. Lever, Kenneth Wagner, John C. Sworen
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Publication number: 20030176754Abstract: A C3 to C6 hydrogen cut from a cracking unit is processed for the conversion of olefins to propylene and hexene via autometathesis. The autometathesis of a mixed normal butenes feed in the presence of a metathesis catalyst operates without any ethylene in the feed mix to the metathesis reactor. Some fraction of the 2-butene feed may be isomerized to 1-butene and the 1-butene formed plus the 1-butene in the feed react rapidly with the 2-butene to form propylene and 2-pentene. The feed to the reactor also includes the recycle of the 2-pentene formed in the reactor with unreacted butenes to simultaneously form additional propylene and hexene. In one embodiment, some or all of the 3-hexene formed in the reaction is isomerized to 1-hexene. In another embodiment, some portion of the 3-hexene produced in the main metathesis reaction is reacted with ethylene to produce 1-butene without the need for superfractionation.Type: ApplicationFiled: March 7, 2002Publication date: September 18, 2003Inventors: Robert J. Gartside, Marvin I. Greene, Quincy J. Jones
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Publication number: 20030163011Abstract: The present invention relates to a process for the metathesis reaction of unsaturated organic compounds.Type: ApplicationFiled: January 14, 2003Publication date: August 28, 2003Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
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Patent number: 6590048Abstract: The present invention describes the use of cationic vinylidene, allenylidene and higher cumulenylidene complexes of ruthenium or osmium as catalysts or catalyst precursors for olefin metathesis reactions of all types, as well as to new cationic allenylidene complexes of ruthenium and osmium which can be used as metathesis catalysts with preferred embodiment. These catalysts or catalyst precursors are easy to prepare from well accessible, stable and essentially non toxic starting materials, can be isolated and stored, they exhibit a high catalytic activity, a good compatibility with functional groups, solvents, water and additives, and they need not to be activated by any additive.Type: GrantFiled: January 2, 2001Date of Patent: July 8, 2003Assignee: Studiengesellschaft Kohle mbHInventors: Alois Fürstner, Pierre Dixneuf, Christian Bruneau, Michel Picquet
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Patent number: 6583329Abstract: The metathesis process is carried out in a reaction distillation column for: (A) for the production of propylene from the metathesis of 2-butene and ethylene; (B) for the production of detergent range olefins from the metathesis of C15 and heavier olefins with C9 and lighter olefins; (C) for the production of 2-methyl-2-butene and propylene from the metathesis of 2-butene and isobutylene and (D) for the production of tetramethylethylene from the metathesis of isobutylene with itself and/or the reaction of diisobutylene with the ethylene produced to produce neohexene.Type: GrantFiled: March 4, 1998Date of Patent: June 24, 2003Assignee: Catalytic Distillation TechnologiesInventor: Gary G. Podrebarac
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Patent number: 6580009Abstract: The process for preparing propene and hexene from a raffinate II feed stream comprising olefinic C4-hydrocarbons comprises a) a metathesis reaction in which butenes present in the feed stream are reacted with ethene in the presence of a metathesis catalyst comprising at least one compound of a metal of transition groups VIb, VIIb or VIII of the Periodic Table of the Elements to give a mixture comprising ethene, propene, butenes, 2-pentene, 3-hexene and butanes, using, based on the butenes, from 0.05 to 0.Type: GrantFiled: March 12, 2001Date of Patent: June 17, 2003Assignee: BASF AktiengesellschaftInventors: Peter Schwab, Ralf Schulz, Sylvia Huber
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Patent number: 6562230Abstract: A process for preparing hydrocarbons in the lube base oil range, lube base oils and lube oil compositions from a fraction with an average molecular weight above a target molecular weight and a fraction with an average molecular weight below a target molecular weight via molecular averaging is described. The fractions can be obtained, for example, from Fischer-Tropsch reactions, and/or obtained from the distillation of crude oil. Molecular averaging converts the fractions to a product with a desired molecular weight, for use in preparing a lube oil composition. The product can optionally be isomerized to lower the pour point, and also can be blended with suitable additives for use as a lube oil composition.Type: GrantFiled: December 22, 1999Date of Patent: May 13, 2003Inventors: Dennis O'Rear, Russell R. Krug
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Patent number: 6538168Abstract: A process for preparing C5/C6-olefins from an olefinic starting stream comprising C4-hydrocarbons comprises a) carrying out a metathesis reaction in the presence of a metathesis catalyst so as to convert the 1-butene, 2-butene and isobutene present in the starting stream into a mixture of C2-C6-olefins and butanes, b) firstly fractioning the resulting product stream by distillation to give a low boiler fraction A comprising C2-C4-olefins and butanes or C2-C3-olefins, which is discharged, and a high boiler fraction comprising C4-C8-olefins and butanes, c) fractioning the high boiler fraction from b) by distillation to give a low boiler fraction B comprising butenes and butanes, an intermediate boiler fraction C comprising pentene and methylbutene and a high boiler fraction D comprising hexane and methylpentene, d) where all or part of the fraction B and/or C are recirculated to the process step a) and the fraction D is discharged as product.Type: GrantFiled: July 6, 2000Date of Patent: March 25, 2003Assignee: BASF AktiengesellschaftInventors: Peter Schwab, Michael Schulz, Ralf Schulz, Sylvia Huber
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Publication number: 20030055305Abstract: There is provided a substantially binder-free catalytic molecular sieve which has been modified by being ex situ selectivated with a silicon compound. The ex situ selectivation involves exposing the molecular sieve to at least two silicon impregnation sequences, each sequence comprising an impregnation with a silicon compound followed by calcination. The catalyst may be used in a hydrocarbon conversion process, such as toluene disproportionation.Type: ApplicationFiled: August 26, 2002Publication date: March 20, 2003Inventors: Jeffrey S. Beck, Jane C. Cheng, Sharon B. McCullen, David H. Olson, David L. Stern
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Patent number: 6518469Abstract: A process for improved yields of heavier olefins from a substantially narrow range of lighter hydrocarbon feed stock containing olefins in a reaction distillation column comprising feeding a narrow range of hydrocarbon feed stock containing olefin into a reaction distillation column at a point between its bottom and top, contacting the olefins at the point of feed with a disproportionation catalyst in alternating arrangement with an isomerization catalyst or a mixture thereof and keeping the reaction mixture in a state of vapor-liquid equilibrium for concentrating the lighter reaction products in the vapor phase and the heavier reaction products in the liquid phase by maintaining a controlled pressure and temperature profile in the reactive distillation column and for reactively creating the desired heavier molecular weight olefins over the catalysts and collecting it as bottoms product and removing the lighter molecular weight olefins overhead from the top of the reactive distillation column.Type: GrantFiled: January 29, 2002Date of Patent: February 11, 2003Inventor: Armen Nazar Abazajian
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Publication number: 20020198426Abstract: A catalytic method is provided for a ring-opening cross-metathesis reaction between a cycloolefinic substrate and a second olefinic reactant, wherein the catalyst used is a transition metal alkylidene complex substituted with an N-heterocyclic carbene ligand. The substrates are selected so that the rate of the cross-metathesis reaction of the second olefinic reactant, kCM, is greater than or equal to the rate of the ring-opening metathesis reaction, kRO. In this way, the predominant ROCM product is a monomer, dimer, and/or oligomer, but not a polymer. The invention additionally provides for selective production of an end-differentiated olefinic product, using trisubstituted cycloolefins as substrates and/or a subsequent cross-metathesis reaction following an initial ROCM step. The cycloolefinic substrates include low-strain olefins such as cyclohexene as well as higher strain olefins such as cyclooctene.Type: ApplicationFiled: April 1, 2002Publication date: December 26, 2002Inventors: John P. Morgan, Christie Morrill, Robert H. Grubbs, Tae-Lim Choi
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Publication number: 20020183578Abstract: For the selective production of propylene from an olefinic C4 fraction, a process is implemented that successively comprises:Type: ApplicationFiled: May 2, 2001Publication date: December 5, 2002Applicant: Institut Francais du PetroleInventors: Dominique Commereuc, Christine Travers
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Production of high-purity isobutene and propylene from hydrocarbon fractions with forur carbon atoms
Publication number: 20020169346Abstract: A process for production, from an olefinic C4 fraction, on the one hand, of high-purity isobutene and, on the other hand, of propylene by metathesis is described.Type: ApplicationFiled: December 26, 2000Publication date: November 14, 2002Applicant: Institut Francais du Petrole of Rueil MalmaisonInventors: Dominique Commereuc, Blaise Didillon, Helene Olivier-Bourbigou, Lucien Saussine -
Publication number: 20020147374Abstract: A process for improved yields of heavier olefins from a substantially narrow range of lighter hydrocarbon feed stock containing olefins in a reaction distillation column comprising feeding a narrow range of hydrocarbon feed stock containing olefin into a reaction distillation column at a point between its bottom and top, contacting the olefins at the point of feed with a disproportionation catalyst in alternating arrangement with an isomerization catalyst or a mixture thereof and keeping the reaction mixture in a state of vapor-liquid equilibrium for concentrating the lighter reaction products in the vapor phase and the heavier reaction products in the liquid phase by maintaining a controlled pressure and temperature profile in the reactive distillation column and for reactively creating the desired heavier molecular weight olefins over the catalysts and collecting it as bottoms product and removing the lighter molecular weight olefins overhead from the top of the reactive distillation column.Type: ApplicationFiled: January 29, 2002Publication date: October 10, 2002Inventor: Armen Nazar Abazajian
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Publication number: 20020120173Abstract: Catalytic process for metathesis of olefins in the presence of a catalyst and a stabilizing agent that is injected into the reaction medium. Application in particular to rebalancing between one another the light olefins that are obtained from steam cracking or catalytic cracking (FCC), such as ethylene, propylene, butenes or pentenes.Type: ApplicationFiled: January 28, 2000Publication date: August 29, 2002Inventors: Dominique Commereuc, Paul Mikitenko
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Patent number: 6441263Abstract: A process for preparing an ethylene-rich composition from a C3-5 paraffinic feedstock is described. The C3-5 paraffinic feedstock is subjected to molecular redistribution via dehydrogenation to form olefins, metathesis of the olefins, and rehydrogenation of the olefins to form paraffins. The product stream includes ethane, which is isolated and sent to an ethane or ethane/propane cracker (or, alternatively, a flexi-cracker, although this is less cost effective) to yield an ethylene-rich composition. The product stream also includes C3-5 paraffins, which can be recycled, and C6+paraffins, which can be used, for example, as solvents. Alternatively, they can be isomerized to form gasoline additives, or can be converted to aromatic compounds by subjecting them to reforming conditions, for example using the AROMAX™ process or platforming or rheniforming conditions.Type: GrantFiled: July 7, 2000Date of Patent: August 27, 2002Assignee: ChevronTexaco CorporationInventors: Dennis J. O'Rear, Rodney Porter, Cong-Yan Chen
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Patent number: 6437209Abstract: Catalytic process for metathesis of olefins in the presence of a catalyst and a stabilizing agent that is injected into the reaction medium. Application in particular to rebalancing between one another the light olefins that are obtained from steam cracking or catalytic cracking (FCC), such as ethylene, propylene, butenes or pentenes.Type: GrantFiled: January 28, 2000Date of Patent: August 20, 2002Assignee: Institut Francais du PetroleInventors: Dominique Commereuc, Paul Mikitenko
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Patent number: 6420619Abstract: The C3 to C6 cut from a cracking process containing propylene, butane, 1-butene, 2-butene and acetylenic and diene components including butadiene are preferentially converted to propylene. The cut is simultaneously fractionated and catalytically hydrogenated to hydrogenate the acetylenic and diene components. The fractionation and subsequent separation recovers a C4 component comprising a mixture of isobutene, 1-butene and 2-butene. This C4 component is then further simultaneously fractionated and catalytically hydrogenated and hydroisomerized to hydrogenate remaining butadiene, remove isobutene overhead and convert 1-butene to 2-butene leaving a bottoms of 2-butene. The 2-butene is then injected with ethylene and catalytically metathesized to form propylene.Type: GrantFiled: January 25, 2001Date of Patent: July 16, 2002Inventors: Robert J. Gartside, Gary R. Gildert
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Patent number: 6392110Abstract: Polyacetylene compounds and process for the preparation thereof from a chiral dihydroxy amide are described. The compounds preferably have diacyl groups attached to the amide. The compounds are useful for making films which are electrically conductive, near infrared absorbing, polarizing, and have the optical characteristic and other properties of polyacetylenes.Type: GrantFiled: August 23, 2000Date of Patent: May 21, 2002Assignee: Board of Trustees of Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang
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Patent number: 6369286Abstract: A process for preparing distillate fuel compositions from a C2-6 olefinic fraction and a C20+ fraction via molecular averaging is described. The fractions can be obtained, for example, from Fischer-Tropsch reactions, and/or obtained from the distillation or other processing of crude oil. Molecular averaging converts the fractions to a product that includes a significant fraction in the C5-20 range that can be used for preparing a distillate fuel composition. The product is preferably isomerized to increase the octane value and lower the pour, cloud and smoke point. The product can also be hydrotreated and/or blended with suitable additives for use as a distillate fuel composition.Type: GrantFiled: March 2, 2000Date of Patent: April 9, 2002Assignee: Chevron U.S.A. Inc.Inventor: Dennis J. O'Rear
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Patent number: 6358482Abstract: A facility for converting an olefinic C4 cut to isobutene and propylene comprising, in succession: 1) a zone 1 for selective hydrogenation of olefins in the olefinic C4 cut with simultaneous isomerisation of butene-1 to butene-2, said zone comprising at least one device for introducing the olefinic C4 cut to be converted, at least one device for removing an effluent, and at least one device for introducing hydrogen, said zone also comprising at least one catalyst bed; 2) a separation zone, comprising at least one device for introducing the effluent from zone 1 directly connected to said at least one device for removing an effluent, at least one device for removing a first fraction comprising isobutene and butene-1, and at least one device for removing a second fraction comprising butene-2 and n-butane, wherein the second fraction comprises at most 1% by weight of isobutene and at most 1% by weight of butene-1; 3) a metathesis zone for metathesis of butene-2 with ethylene to produce propylene, wherein the mType: GrantFiled: March 7, 2000Date of Patent: March 19, 2002Assignee: Institut Francais du PetroleInventors: Jean Alain Chodorge, Dominique Commereuc, Jean Cosyns
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Patent number: 6346652Abstract: A composition and method for the catalytic conversion of a racemic mixture of dienes to a cyclic olefin by a ring-closing metathesis (RCM) reaction are disclosed. The composition, a transition metal complex with an M═C reaction site, contains a bidentate dialkoxide of at least 80% optical purity. Because the M═C reaction site is of a sufficient shape specificity, conferred in part by the dialkoxide of sufficient rigidity and a M═N—R1 site, reacting the composition with a mixture of two enantiomeric dienes results in an olefin metathesis product that has at least a 50% enantiomeric excess of one enantiomer in the mixture. A method is also provided for reacting a composition with a racemic diene mixture to generate a metathesis product that has an enantiomeric excess of at least 50%. Methods are also provided for catalytic enantioselective desymmetrization.Type: GrantFiled: July 13, 1998Date of Patent: February 12, 2002Assignee: Massachusetts Institute of TechnologyInventors: Richard R. Schrock, Amir H. Hoveyda
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Publication number: 20020002317Abstract: The process for preparing propene and hexene from a raffinate II feed stream comprising olefinic C4-hydrocarbons comprisesType: ApplicationFiled: March 12, 2001Publication date: January 3, 2002Inventors: Peter Schwab, Ralf Schulz, Sylvia Huber
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Patent number: 6313365Abstract: The invention has an object of safely and simply preparing a large amount of a ruthenium metathesis catalyst, which is used as a catalyst for a carbon-carbon bond formation using, particularly, a metathesis reaction. The metathesis catalyst has the following complex composition (A) or (B).Type: GrantFiled: September 20, 2000Date of Patent: November 6, 2001Assignee: Takasago International CorporationInventors: Yoji Hori, Yukiharu Iwaya, Tsutomu Hashimoto, Toshimitsu Hagiwara
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Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
Patent number: 6284852Abstract: Activation of ruthenium based catalyst compounds with acid to improve reaction rates and yields of olefin metathesis reactions, including ROMP, RCM, ADMET and cross-metathesis reactions is disclosed. The ruthenium catalyst compounds are ruthenium carbene complexes of the general formula AxLyXzRu═CHR′ where x=0, 1 or 2, y=0, 1 or 2, and z=1 or 2 and where R′ is hydrogen or a substituted or unsubstituted alkyl or aryl, L is any neutral electron donor, X is any anionic ligand, and A is a ligand having a covalent structure connecting a neutral electron donor and an anionic ligand. The use of acid with these catalysts allows for reactions with a wide range of olefins in a variety of solvents, including acid-initiated RIM processes and living ROMP reactions of water-soluble monomers in water.Type: GrantFiled: October 29, 1998Date of Patent: September 4, 2001Assignee: California Institute of TechnologyInventors: David M. Lynn, Eric L. Dias, Robert H. Grubbs, Bernard Mohr -
Patent number: 6284939Abstract: This invention pertains to a continuous catalytic process, for example, for the metathesis of olefins that uses a catalyst circulating in a moving bed in at least one reaction zone operating in the liquid phase and in a regenerator, with a lift to transfer the deactivated catalyst emerging from the reaction zone to the regenerator, whereby said process is characterized by the fact that the transfer is accomplished by a gas that does not react with the catalyst and with the stripping off of at least a portion of the organic matter that is adsorbed on the deactivated catalyst.Type: GrantFiled: July 30, 1999Date of Patent: September 4, 2001Assignee: Institut Francais du PetroleInventors: Frédéric Hoffmann, Philippe Mege, Dominique Commereuc
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Patent number: 6281402Abstract: The present invention relates to a process for continuous metathesis or disproportionation of olefins, comprising at least 2 phases, a reaction phase a) carried out in a zone comprising at least one reactor containing at least one fixed bed of catalyst and a regeneration phase b) carried out in a zone comprising at least one reactor containing at least one fixed bed of catalyst, characterized in that at least one reactor passes from one phase to the other in alternation. In FIG. 1, the feed containing olefins traverses reactor R1 in riser mode. The feed to be treated containing olefins is introduced into reactor R1 via line 1a. In this reactor, the olefins contained in the feed undergo metathesis or disproportionation, then the effluent leaves the circuit via line 11. Simultaneously, reactor R2 is placed in catalyst regeneration phase, the different regeneration gases are introduced into reactor R2 via line 2b and leave this reactor via line 2c.Type: GrantFiled: December 10, 1998Date of Patent: August 28, 2001Assignee: Institut Francais du PetroleInventors: Vincent Coupard, François Hugues, Dominique Commereuc, Béatrice Fischer, Pierre Boucot, Alain Forestiere