Using Co-, Fe-, Or Ni-containing Catalyst Patents (Class 585/369)
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Patent number: 10364200Abstract: 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 contacting a feedstock comprising acyclic hydrocarbons with a catalyst material in at least one reaction zone to convert at least a portion of the acyclic hydrocarbons to a first effluent comprising alkenes, cyclic hydrocarbons and/or aromatics. A co-feed comprising H2, C1-C4 alkanes and/or C1-C4 alkenes may also be provided to the at least one reaction zone.Type: GrantFiled: February 9, 2018Date of Patent: July 30, 2019Assignee: ExxonMobil Chemical Patents Inc.Inventors: Neeraj Sangar, Larry L. Iaccino, Christopher L. Becker
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Patent number: 9764997Abstract: A method for making hydrogenated cyclooctatetraene dimers including cyclo-dimerizing butadiene to form 1,5-cyclooctadiene in the presence of at least one first catalyst, dehydrogenating 1,5-cyclooctadiene to 1,3,5,7-cyclooctatetraene, dimerizing 1,3,5,7-cyclooctatetraene to a C16 multicyclic hydrocarbon cyclooctatetraene dimer, and hydrogenating multicyclic hydrocarbon cyclooctatetraene dimer to form hydrogenated cyclooctatetraene dimers.Type: GrantFiled: April 14, 2016Date of Patent: September 19, 2017Assignee: The United States of America as Represented by the Secretary of the NavyInventor: Benjamin G Harvey
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Patent number: 8378159Abstract: A method of producing a hydrocarbon fuel from a hydrocarbon-containing gas is disclosed and described. A hydrocarbon-containing gas is produced (10) containing from about 25% to about 50% carbon dioxide and can be reformed (12) with a steam gas to form a mixture of hydrogen, carbon monoxide and carbon dioxide. The reforming can be a composite dry-wet reforming or a tri-reforming step. The mixture of hydrogen, carbon monoxide and carbon dioxide can be at least partially converted (14) to a methanol product. The methanol product can be converted to the hydrocarbon fuel (18), optionally via DME synthesis (16). The method allows for effective fuel production with low catalyst fouling rates and for operation in an unmanned, self-contained unit at the source of the hydrocarbon-producing gas.Type: GrantFiled: December 17, 2009Date of Patent: February 19, 2013Assignee: Oberon Fuels, Inc.Inventors: Andrew Corradini, Jarod McCormick
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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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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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Publication number: 20070265184Abstract: 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: ApplicationFiled: March 20, 2007Publication date: November 15, 2007Applicant: DEGUSSA AGInventors: Jurgen Herwig, Wilhelm Brugging, Martin Roos, Norbert Wilczok
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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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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: 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: 5545789Abstract: The invention relates to a process for the dimerization of a conjugated diene using an iron triad metal nitrosyl halide, in combination with a reducing agent, as catalyst. The process is characterized in that the dimerization is carried out in the presence of nitrogen monoxide (NO). The invention is of interest in particular for the dimerization of butadiene to 4-vinyl cyclohexene.Type: GrantFiled: May 5, 1995Date of Patent: August 13, 1996Assignee: DSM N.V.Inventors: Henricus A. M. Duisters, Johan G.D. Haenen
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Patent number: 5096870Abstract: Catalysts suitable for the dimerization of a diolefin, e.g. butadiene to 4-vinylcyclohexene, are prepared by reacting (1) iron chloride and sodium nitrite or alternatively (2) iron nitrosyl chloride with (3) carbon monoxide in an organic solvent in the presence of iron. The catalyst solution is preferably filtered prior to use. While the reaction employing iron chloride and sodium nitrile is preferred, the catalyst produced by either method contains a minimum of reducing agent and by-products. It can be isolated and stored in the absence of diolefin monomer and carbon monoxide while retaining its stability and activity.Type: GrantFiled: September 5, 1990Date of Patent: March 17, 1992Assignee: The Dow Chemical CompanyInventor: Duane E. Heaton
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Patent number: 5057469Abstract: Iron nitrosyl carbonyl catalyst is prepared by dissolving impure iron nitrosyl carbonyl in a solvent solution, then adding sufficient miscible non-solvent to the solution to result in separation of the mixture into an upper layer and a lower layer containing iron nitrosyl carbonyl. Preferably, the solvent is used in preparation of the iron nitrosyl carbonyl, and the solution is, therefore, the product of the preparation. The miscible non-solvent is added to the product solution to effect separation of layers for isolation of purified iron nitrosyl carbonyl product.Type: GrantFiled: September 5, 1990Date of Patent: October 15, 1991Assignee: The Dow Chemical CompanyInventor: Duane E. Heaton
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Patent number: 5043504Abstract: In a process of cyclodimerizing a conjugated diene to form a cycloalkene using a soluble iron complex as catalyst, the improvement comprises using as an inhibitor of diene polymerization, at least one hindered phenol.Type: GrantFiled: September 5, 1990Date of Patent: August 27, 1991Assignee: The Dow Chemical CompanyInventor: Stephen A. Bedell
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Patent number: 4954125Abstract: A catalyst consisting essentially of (A) a cobalt compound and (B) an organic phosphorus compound represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen atoms, alkyl groups or aryl groups, and three X's, which may be the same or different, are electron-donating groups. This catalyst is effectively used in a process for producing a conjugated diene polymer by polymerizing a conjugated diene in a hydrocarbon or halogenated hydrocarbon solvent in the presence of the above catalyst together with (C) an organoaluminum compound and (D) 0.25-1.5 mols, per mol of the organoaluminum compound (C), of water.Type: GrantFiled: June 20, 1988Date of Patent: September 4, 1990Assignee: Japan Synthetic Rubber Company, Ltd.Inventors: Hisao Ono, Ryuji Sato, Takumi Miyachi
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Patent number: 4827067Abstract: The invention relates to azaphospholene of the type ##STR1## wherein R.sub.1 and R.sub.2 may be alkyl, aryl and aralkyl groups, processes for preparing same and the use thereof.Type: GrantFiled: September 19, 1988Date of Patent: May 2, 1989Assignee: Studiengesellschaft Kohle mbHInventors: Gunther Wilke, Jaroslaw Monkiewicz, Herbert Kuhn
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Patent number: 4323698Abstract: This specification discloses an insoluble resin-metal compound complex, the method for its preparation, and its use in carrying out a catalyzed reaction. The complex is a weak base anion exchange resin which has been contacted with a solution of a coordination compound having at least two ligands connected to at least one central metal atom to bond chemically the resin to the metal atom by replacement of at least one of the ligands of the coordination compound by a functional group of the weak base anion exchange resin. The complex can be used as a catalyst for hydrogenation, carbon monoxide insertion, polymerization, isomerization, vinyl ester exchange, and ethylene oxidation reactions, among others.Type: GrantFiled: January 21, 1980Date of Patent: April 6, 1982Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 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: 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: 4213901Abstract: Compounds of the formula ##STR1## and a process for their preparation by reacting azabutadienes with dienes, especially 1,3-butadiene, in the presence of catalysts are described. In the formula I, R.sub.1 and R.sub.3 independently of one another are hydrogen or alkyl having 1-8 C atoms and R.sub.2 and R.sub.4 independently of one another are alkyl having 1-8 C atoms, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together with the bonding C atom form a cycloaliphatic ring having 4-8 C atoms, and R.sub.5 and R.sub.6 independently of one another are hydrogen or alkyl having 1-4 C atoms. The compounds of the formula I are valuable intermediates for the preparation of active compounds for combating plant pests.Type: GrantFiled: July 10, 1978Date of Patent: July 22, 1980Assignee: Ciba-Geigy CorporationInventor: Dieter Reinehr
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Patent number: 4187386Abstract: 1,5-Hexadiene is cyclized to cyclohexene by contacting 1,5-hexadiene with a mixture of a first catalyst selected from the group consisting of chromium oxides, chromium chlorides, chromium bromides, molybdenum oxides, molybdenum chlorides, molybdenum bromides, tungsten oxides, tungsten chlorides, tungsten bromides, iron oxides, cobalt oxides, nickel oxides, elemental sulfur, SiO.sub.2, Al.sub.2 O.sub.3, vanadium metal, vanadium oxides, VOF.sub.3, and mixtures thereof, and a second catalyst selected from a tin (IV) halide and mixtures thereof.Type: GrantFiled: December 29, 1978Date of Patent: February 5, 1980Assignee: Allied Chemical CorporationInventors: George D. Lockyer, Jr., Dennis E. Burd, Richard F. Sweeney, Bernard Sukornick, Harry E. Ulmer
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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