Alkadiene Patents (Class 585/366)
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Patent number: 11261140Abstract: This invention relates to processes and systems for converting acyclic hydrocarbons to alkenes, cyclic hydrocarbons and/or aromatics, for example converting acyclic C5 hydrocarbons to cyclopentadiene in a reactor system. The process includes heating an electrically-conductive reaction zone by applying an electrical current to the first electrically-conductive reaction zone; and contacting a feedstock comprising acyclic hydrocarbons with a catalyst material in the electrically-conductive reaction zone under reaction conditions to convert at least a portion of the acyclic hydrocarbons to an effluent comprising alkenes, cyclic hydrocarbons, and/or aromatics.Type: GrantFiled: June 5, 2018Date of Patent: March 1, 2022Assignee: ExxonMobil Chemical Patents Inc.Inventors: Neeraj Sangar, Larry L. Iaccino, Christopher L. Becker
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Patent number: 9290423Abstract: A renewable fuel may be obtained from a bio-oil containing C3-C5 oxygenates. In a first step, the bio-oil is subjected to a condensation reaction in which the oxygenates undergo a carbon-carbon bond forming reaction to produce a stream containing C6+ oxygenates. In a second step, the stream is hydrotreated to produce C6+ hydrocarbons.Type: GrantFiled: November 19, 2012Date of Patent: March 22, 2016Assignee: KiOR, LLCInventors: Jeffrey C Trewella, Edward J Smith, Vicente Sanchez, Brent Moore, Stephen J. McGovern
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Patent number: 9200209Abstract: A renewable fuel may be obtained from a bio-oil containing C3-C5 oxygenates. In a first step, the bio-oil is subjected to a condensation reaction in which the oxygenates undergo a carbon-carbon bond forming reaction to produce a stream containing C6+ oxygenates. In a second step, the stream is hydrotreated to produce C6+ hydrocarbons.Type: GrantFiled: March 15, 2013Date of Patent: December 1, 2015Assignee: KiOR, Inc.Inventors: Lorenz J. Bauer, Leslie May, Jeffrey C. Trewella, Maria Magdalena Ramirez Corredores, Christopher Paradise, Nicholas Kent
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Patent number: 9169174Abstract: A method for suppressing isomerization of an olefin metathesis product produced in a metathesis reaction includes adding an isomerization suppression agent that includes nitric acid to a mixture that includes the olefin metathesis product and residual metathesis catalyst from the metathesis reaction under conditions that are sufficient to passivate at least a portion of the residual metathesis catalyst. Methods of refining a natural oil are described.Type: GrantFiled: December 22, 2011Date of Patent: October 27, 2015Assignee: Elevance Renewable Sciences, Inc.Inventors: Bruce E. Firth, Sharon E. Kirk
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Patent number: 8993819Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: GrantFiled: July 10, 2012Date of Patent: March 31, 2015Assignee: BASF SEInventors: Joaquim Henrique Teles, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Patent number: 8859779Abstract: Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbene ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.Type: GrantFiled: January 25, 2013Date of Patent: October 14, 2014Assignee: Materia, Inc.Inventors: Steven P. Nolan, Jinkun Huang
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Publication number: 20130018205Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: ApplicationFiled: July 10, 2012Publication date: January 17, 2013Applicant: BASF SEInventors: Joaquim Henrique TELES, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Patent number: 8168841Abstract: Preparation of cyclododecatriene in a continuous or discontinuous process by trimerization of butadiene in the presence of a catalyst system and a solvent, the crude cyclododecatriene obtained being able to be isolated by means of distillation. The cyclooctadiene formed as by-product can likewise be isolated from the crude product.Type: GrantFiled: March 20, 2007Date of Patent: May 1, 2012Assignee: EVONIK DEGUSSA GmbHInventors: Jürgen Herwig, Wilhelm Brügging, Martin Roos, Norbert Wilczok
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Patent number: 8039566Abstract: This invention relates to olefin metathesis catalysts general formula (I): having a thiazol-2-ylidene ligand of general formula (II): The catalysts have been found to be particularly good initiators of (a) ring-closing metathesis reactions used to prepare tetra-substituted cyclic olefins, and (b) cross-metathesis reactions used to prepare tri-substituted and di-substituted olefins.Type: GrantFiled: November 20, 2007Date of Patent: October 18, 2011Assignee: California Institute of TechnologyInventors: Georgios C. Vougioukalakis, Robert H. Grubbs
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Patent number: 7902389Abstract: Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbine ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.Type: GrantFiled: November 19, 2009Date of Patent: March 8, 2011Inventors: Steven P. Nolan, Jinkun Huang
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Publication number: 20100160642Abstract: Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbine ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.Type: ApplicationFiled: November 19, 2009Publication date: June 24, 2010Applicant: University of New Orleans Research & Technology Foundation, Inc.Inventors: Steven P. Nolan, Jinkun Huang
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Patent number: 7622590Abstract: Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbene ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.Type: GrantFiled: September 9, 1999Date of Patent: November 24, 2009Assignee: University of New Orleans FoundationInventors: Steven P. Nolan, Jinkun Huang
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Publication number: 20090099059Abstract: The present invention relates to the preparation of trimethylcyclododecatriene in a continuous or batchwise process by trimerizing isoprene in the presence of a catalyst system and of a solvent. It is possible to isolate the resulting crude trimethylcyclododecatriene by means of distillation. The dimethylcyclooctadiene formed as a by-product may likewise be isolated from the crude product.Type: ApplicationFiled: September 13, 2005Publication date: April 16, 2009Applicant: DEGUSSA GmbHInventors: Dirk Kuppert, Juergen Herwig, Norbert Wilczok, Anita Voelkel, Manfred Thiery
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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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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: 20030176749Abstract: 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: ApplicationFiled: March 15, 2002Publication date: September 18, 2003Inventors: John G. Lever, Kenneth Wagner, John C. Sworen
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Publication number: 20030023123Abstract: Reaction mixtures and methods using catalysts and reaction conditions to produce significantly improved yields (and thereby higher purity) of olefin metathesis products, with greatly reduced amounts of impurities. These techniques include in one instance reduction in temperature of reaction, and in another, the use of chemical compounds that act as reaction inhibitors of unwanted reactions to minimize or prevent formation of unwanted impurities.Type: ApplicationFiled: May 24, 2002Publication date: January 30, 2003Inventors: Basil P. Paulson, Richard L. Pederson
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Patent number: 6403851Abstract: Cyclododecatrienes may be prepared in a continuous process by reacting 1,3-butadiene in the presence of a catalyst system and cyclooctadiene and/or cyclododecatriene. The resulting crude cyclododecatriene product may be separated from this mixture by distillation, and 50 to 100% of the catalyst system may be recycled back into the process.Type: GrantFiled: July 13, 2000Date of Patent: June 11, 2002Assignee: Degussa AGInventors: Norbert Wilczok, Thomas Schiffer, Peter Wiedenbusch
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Patent number: 6093865Abstract: The present invention relates to a method for using a single distillation column to recover the reactants and products from the reaction of a cyclic diolefin and an olefin to produce an alkenyl bridged ring compound.Type: GrantFiled: June 16, 1998Date of Patent: July 25, 2000Assignee: Exxon Chemical Patent Inc.Inventors: James R. Lattner, Leonel E. Sanchez, Christopher L. Becker, Bruce C. Devoy
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Patent number: 5939504Abstract: Compositions and methods for catalyzing and controlling the rate of olefin metathesis reactions including Ring Opening Metathesis Polymerization (ROMP) reactions. The molding of polymer articles using ROMP polymers. The composition includes a Ruthenium or Osmium carbene complex catalyst and a gel modification additive. The Ruthenium or Osmium carbene complex catalyst having the formula ##STR1## where M may be Os or Ru; R and R.sup.1 may be the same or different and may be hydrogen or a substituent group including C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl and C.sub.1 -C.sub.20 alkylsulfinyl; X and X.sup.1 may be the same or different and may be any anionic ligand; and L and L.sup.1 may be the same or different and may be neutral electron donor.Type: GrantFiled: December 2, 1996Date of Patent: August 17, 1999Assignee: Advanced Polymer TechnologiesInventors: Charles S. Woodson, Jr., Robert H. Grubbs
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Patent number: 5625101Abstract: 1,3-butadiene is cyclodimerized to 4-vinylcyclohexene in the presence of at least one copper(I) sulfonate as the catalyst.Type: GrantFiled: June 30, 1995Date of Patent: April 29, 1997Assignee: Phillips Petroleum CompanyInventors: Tin-Tack P. Cheung, Marvin M. Johnson
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Patent number: 5569804Abstract: The present invention relates to a method for using a single distillation column to recover the reactants and products from the reaction of a cyclic diolefin and an olefin to produce an alkenyl bridged ring compound.Type: GrantFiled: December 30, 1993Date of Patent: October 29, 1996Assignee: Exxon Chemical Patents Inc (ECPI)Inventors: James R. Lattner, Leonel E. Sanchez
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Patent number: 5565069Abstract: A process for producing 5-vinyl-2-norbornene which comprises the steps of subjecting a liquid raw material in which tetrahydroindene/dicyclopentadiene ratio (by weight) falls within the range of from 5/100 to 80/100 to a thermal decomposition in liquid phase in the presence of an aromatic hydrocarbon solvent having a boiling point of from 250.degree. C. to 300.degree. C. at a reaction temperature of not lower than 200.degree. C. and lower than 240.degree. C.Type: GrantFiled: May 26, 1995Date of Patent: October 15, 1996Assignee: Sumitomo Chemical Company LimitedInventors: Nobuo Oi, Kazuo Kimura, Kenichi Nariyama
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Patent number: 5516953Abstract: A process for the preparation of optically active cycloolefins based upon reaction of optically active dienes in the presence of catalyst compositions comprising molybdenum and tungsten complexes.Type: GrantFiled: March 8, 1994Date of Patent: May 14, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Jerald Feldman, William A. Nugent, Jr.
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Patent number: 5488020Abstract: A composition comprising a copper(I) impregnated aluminosilicate zeolite wherein the zeolite is selected from faujasites, L and .OMEGA., and wherein the zeolite has a silica to bulk alumina molar ratio between about 12 and about 50 and a silica to framework alumina molar ratio of at least about 15. The catalyst preparation involves in the following order: drying the selected zeolite, impregnating the dried zeolite with a copper(II) salt, calcining the copper(II)-impregnated zeolite, and reducing the copper(II) to copper(I). The composition is useful as a catalyst for the cyclodimerization of 1,3-butadiene to 4-vinylcyclohexene.Type: GrantFiled: February 23, 1994Date of Patent: January 30, 1996Assignee: The Dow Chemical CompanyInventors: Ronald W. Diesen, Kenneth A. Burdett, Ravi S. Dixit, Stanley S. T. King
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Patent number: 5446225Abstract: An alkylative cycloaddition method is provided that is particularly useful for the synthesis of many of the Vitamin D analogues with differing side chains. Thus, a preferred synthesis is of Vitamin D analogues having a side chain R.sub.1 where a first precursor having the structure ##STR1## with X being a halide or a pseudo halide, and a second precursor are provided, the second precursor being a 1,7 enyne. These precursors are reacted in the presence of a palladium catalyst to form compounds having the structure ##STR2## where R.sub.2 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group, and R.sub.3 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group.Type: GrantFiled: December 23, 1993Date of Patent: August 29, 1995Assignee: Board of Trustees of the Leland Stanford Junior Univ.Inventors: Barry M. Trost, Jacques Dumas
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Patent number: 5329057Abstract: A process for the cyclodimerization of 1,3-butadienes to 4-vinylcyclohexenes. The process involves contacting butadiene with a copper (I)-aluminosilicate zeolite prepared by (a) an impregnation method, or (b) heating a solid mixture of a copper salt and the zeolite, or (c) contacting vapors of a copper salt with the zeolite. The catalysts exhibit long life and good activity in the claimed process. The impregnated Cu(I)-catalyst is claimed.Type: GrantFiled: September 30, 1992Date of Patent: July 12, 1994Assignee: The Dow Chemical CompanyInventors: Ronald W. Diesen, Kenneth A. Burdett, Ravi S. Dixit, Stanley S. T. King
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Patent number: 5292977Abstract: An alkylative cycloaddition method is provided that is particularly useful for the synthesis of many of the Vitamin D analogues with differing side chains. Thus, a preferred synthesis is of Vitamin D analogues having a side chain R.sub.1 where a substantially geometrically pure first precursor having the structure ##STR1## and a second precursor are provided, the second precursor being a 1,7 enyne. These precursors are reacted in the presence of a palladium catalyst to form compounds having the structure ##STR2## where R.sub.2 hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group, and R.sub.3 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group.Type: GrantFiled: April 20, 1993Date of Patent: March 8, 1994Assignee: Board of Trustees of Leland Stanford Junior UniversityInventors: Barry M. Trost, Jacques Dumas
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Patent number: 5196621Abstract: A process for the cyclodimerization of 1,3-butadienes to 4-vinylcyclohexenes comprising contacting a butadiene in the presence of a promoting amount of a hydroxylic solvent with a catalyst containing copper(I) ions supported on a carrier. A second process for the cyclodimerization of 1,3-butadienes to 4-vinylcyclohexenes comprising contacting a butadiene with a catalytic amount of a copper(I)-impregnated aluminosilicate zeolite characterized by a bulk SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio in the range from about 5 to about 50 and a framework SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of at least about 15. A catalyst composition comprising a copper(I)-impregnated zeolite of specified bulk and framework silica to alumina molar ratios and specified water content. The catalyst exhibits high activity and long lifetime in the aforementioned dimerization processes and is easily regenerated.Type: GrantFiled: April 19, 1991Date of Patent: March 23, 1993Assignee: The Dow Chemical CompanyInventors: Ronald W. Diesen, Kenneth A. Burdett, Ravi S. Dixit, Stanley S. T. King, Michael M. Olken
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Patent number: 4777309Abstract: A continuous process for producing 5-vinyl-2-norbornene, useful as the raw material of 5-ethylidene-2-norbornene used as a termonomer for EPDM, from a mixture of cyclopentadiene and butadiene or from a mixture of cyclopentadiene and dicyclopentadiene and butadiene by the Diels-Alder reaction which process comprises adding from 10 to 10,000 ppm of N,N-diethylhydroxylamine or 4-oxo-2,2,6,6-tetramethylpiperidine-1-oxyl relative to the total weight of cyclopentadiene and butadiene or of a mixture of cyclopentadiene and dicyclopentadiene and butadiene, continuously introducing the resulting mixture into a pressure reaction vessel, allowing them to react in the absence of any gas phase portion within the said pressure reaction vessel, and continuously withdrawing the reaction product.Type: GrantFiled: September 29, 1987Date of Patent: October 11, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuo Kimura, Masahiro Usui, Fujio Masuko
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Patent number: 4665247Abstract: The present invention provides a process which is adapted for cyclodimerization of 1,3-butadiene to 4-vinylcyclohexene-1 under Diels-Alder conditions in the presence of a copper-containing ZSM-12.Type: GrantFiled: November 15, 1985Date of Patent: May 12, 1987Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 4554375Abstract: A method for preparing 2,7-octadienyl formate by reacting 1,3-butadiene with formic acid in the presence of a platinum(II) catalyst is described. The platinum(II) catalyst is preferably platinum acetylacetonate. A reaction temperature between 50.degree. and 150.degree. C. is preferred, and carbon dioxide and a solvent may also be employed. Tetrahydrofuran and acetone are the preferred aprotic solvents.Type: GrantFiled: March 15, 1984Date of Patent: November 19, 1985Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, David C. Alexander
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Patent number: 4413154Abstract: The present invention provides a process which is adapted for cyclodimerization of 1,3-butadiene to 4-vinylcyclohexene under Diels-Alder conditions in the presence of a large-pore carbon molecular sieve.Type: GrantFiled: September 27, 1982Date of Patent: November 1, 1983Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 4396787Abstract: Formation of undesirable popcorn polymer on the walls of a reaction vessel during thermal dimerization of butadiene is prevented by coating the walls with a falling film of aqueous sodium nitrite solution.Type: GrantFiled: November 23, 1981Date of Patent: August 2, 1983Assignee: Deutsche Texaco AktiengesellschaftInventors: Karl-Heinz Gluzek, Olaf Petersen, Wilhelm Neier, Gunter Strehlke, Karl-Heinz Heinemann
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Patent number: 4384153Abstract: The present invention provides a process which is adapted for cyclodimerization of 1,3-butadiene to 4-vinylcyclohexene-1 under Diels-Alder conditions in the presence of a low acidity form of a large-pore zeolite such as ZSM-20, beta or Y.Type: GrantFiled: March 18, 1982Date of Patent: May 17, 1983Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 4270016Abstract: A method of preparing trans-, trans-, trans-1,5,9-cyclododecatriene which comprises cyclotrimerization of butadiene at a temperature within the range of from 50.degree. to 150.degree. C. in the presence of a catalytic system consisting of a compound of bivalent nickel, an organo-aluminium compound of the formula (1) or (2):R.sub.3 Al (1)andR.sub.2 Al--X (R').sub.n (2)wherein R, and R' are each C.sub.2 H.sub.5 --, ##STR1## X is --O-- when n=1 and --N-- when n=2; and an activator, viz. a compound of formula (3) or (4):R.sub.3 Si--OR' (3)wherein R is an alkyl; R' is an alkyl, C.sub.6 H.sub.5 --, C.sub.6 H.sub.11,N(CRR'--CRR"--O).sub.3 B (4)wherein R and R" are each CH.sub.3 --, C.sub.2 H.sub.5 --, C.sub.6 H.sub.10, C.sub.8 H.sub.11 --, H--; R is H--.The method according to the present invention makes it possible to increase the yield of the desired product up to 95% by weight.Type: GrantFiled: June 1, 1979Date of Patent: May 26, 1981Inventors: Genrikh A. Tolstikov, Usein M. Dzhemilev, Grigory I. Rutman, Jury I. Michurov, Boris I. Pantukh, Stanislav S. Shavanov, Sagid R. Rafikov, Sofia A. Egoricheva, Valery P. Juriev, Alexandr G. Liakumovich, Valerian M. Sobolev, Boris S. Korotkevich, Jury A. Shmuk, Elena Y. Mandelshtamm
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Patent number: 4225738Abstract: This invention provides a three-step process for converting n-butene into high purity 1,3-butadiene, via a vinylcyclohexene intermediate.In the first step of the process, n-butene and molecular oxygen are contacted with a Group VIII metal oxide catalyst. If nitrobenzene is employed as the oxidizing agent in place of molecular oxygen then aniline is produced as a secondary product of the process.Type: GrantFiled: April 23, 1979Date of Patent: September 30, 1980Assignee: El Paso Products CompanyInventor: John L. Cihonski
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Patent number: 4219688Abstract: In a process for producing vinylnorbornene and/or tetrahydroindene by the Diels-Alder reaction between butadiene and cyclopentadiene, the improvement that the intended product is obtained with high selectivity and high conversion can be achieved by carrying out said reaction in a solvent which has a molecular refraction R.sub.D of 30 or more and a boiling point of 150.degree. C. or higher and which is thermally stable and inert to the reactants as well as to the reaction products.Type: GrantFiled: September 6, 1978Date of Patent: August 26, 1980Assignee: Japan Synthetic Rubber Co., Ltd.Inventor: Masaya Ogawa
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Patent number: 4214108Abstract: The process for making cyclododecatriene(1,5,9)-enes by catalytically trimerizing butadiene using a catalyst from a titanium halide and an alkylaluminum halide in the presence of hydrocarbons or halogenated hydrocarbons is improved by carrying out the reaction in the presence of dibenzyenes having the general formula ##STR1## where R.sub.1 through R.sub.6 represent hydrogen atoms, halogen atoms, alkyl groups, aralkyl groups, cycloalkyl groups, or aryl groups, the dibenzylbenzenes being used in at least equimolar amounts with respect to the titanium compound.Type: GrantFiled: June 4, 1979Date of Patent: July 22, 1980Assignee: Chemische Werke Huls AktiengesellschaftInventor: Wolfgang Zaar
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Patent number: 4166076Abstract: 1,5-Dimethyl-1,5-cyclooctadiene and 1,4-dimethyl-4-vinyl-1-cyclohexene are prepared by contacting isoprene with a catalyst obtained by mixing a nickel compound, a reducing agent capable of reducing the nickel to zerovalent nickel, and a trihydrocarbyl phosphite, arsenite or antimonite wherein at least one of the three hydrocarbyl groups is a substituted hydrocarbyl group CF.sub.3 --(CF.sub.2).sub.n C(H)(R)--, in which n.gtoreq.0 and R is an optionally substituted hydrocarbyl group. Only very small amounts of the undesired 1,6-dimethyl-1,5-cyclooctadiene are formed.Type: GrantFiled: January 16, 1978Date of Patent: August 28, 1979Assignee: Shell Oil CompanyInventors: Cornelis F. Roobeek, Petrus W. N. M. VAN Leeuwen