Using Co-, Fe-, Or Ni-containing Catalyst Patents (Class 585/369)
  • Patent number: 10364200
    Abstract: 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: Grant
    Filed: February 9, 2018
    Date of Patent: July 30, 2019
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Neeraj Sangar, Larry L. Iaccino, Christopher L. Becker
  • Patent number: 9764997
    Abstract: 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: Grant
    Filed: April 14, 2016
    Date of Patent: September 19, 2017
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventor: Benjamin G Harvey
  • Patent number: 8378159
    Abstract: 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: Grant
    Filed: December 17, 2009
    Date of Patent: February 19, 2013
    Assignee: Oberon Fuels, Inc.
    Inventors: Andrew Corradini, Jarod McCormick
  • Patent number: 8168841
    Abstract: 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: Grant
    Filed: March 20, 2007
    Date of Patent: May 1, 2012
    Assignee: EVONIK DEGUSSA GmbH
    Inventors: Jürgen Herwig, Wilhelm Brügging, Martin Roos, Norbert Wilczok
  • Publication number: 20090099059
    Abstract: 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: Application
    Filed: September 13, 2005
    Publication date: April 16, 2009
    Applicant: DEGUSSA GmbH
    Inventors: Dirk Kuppert, Juergen Herwig, Norbert Wilczok, Anita Voelkel, Manfred Thiery
  • Publication number: 20070265184
    Abstract: 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: Application
    Filed: March 20, 2007
    Publication date: November 15, 2007
    Applicant: DEGUSSA AG
    Inventors: Jurgen Herwig, Wilhelm Brugging, Martin Roos, Norbert Wilczok
  • Publication number: 20030176749
    Abstract: 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: Application
    Filed: March 15, 2002
    Publication date: September 18, 2003
    Inventors: John G. Lever, Kenneth Wagner, John C. Sworen
  • Patent number: 6403851
    Abstract: 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: Grant
    Filed: July 13, 2000
    Date of Patent: June 11, 2002
    Assignee: Degussa AG
    Inventors: Norbert Wilczok, Thomas Schiffer, Peter Wiedenbusch
  • Patent number: 5625101
    Abstract: 1,3-butadiene is cyclodimerized to 4-vinylcyclohexene in the presence of at least one copper(I) sulfonate as the catalyst.
    Type: Grant
    Filed: June 30, 1995
    Date of Patent: April 29, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Tin-Tack P. Cheung, Marvin M. Johnson
  • Patent number: 5545789
    Abstract: 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: Grant
    Filed: May 5, 1995
    Date of Patent: August 13, 1996
    Assignee: DSM N.V.
    Inventors: Henricus A. M. Duisters, Johan G.D. Haenen
  • Patent number: 5096870
    Abstract: 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: Grant
    Filed: September 5, 1990
    Date of Patent: March 17, 1992
    Assignee: The Dow Chemical Company
    Inventor: Duane E. Heaton
  • Patent number: 5057469
    Abstract: 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: Grant
    Filed: September 5, 1990
    Date of Patent: October 15, 1991
    Assignee: The Dow Chemical Company
    Inventor: Duane E. Heaton
  • Patent number: 5043504
    Abstract: 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: Grant
    Filed: September 5, 1990
    Date of Patent: August 27, 1991
    Assignee: The Dow Chemical Company
    Inventor: Stephen A. Bedell
  • Patent number: 4954125
    Abstract: 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: Grant
    Filed: June 20, 1988
    Date of Patent: September 4, 1990
    Assignee: Japan Synthetic Rubber Company, Ltd.
    Inventors: Hisao Ono, Ryuji Sato, Takumi Miyachi
  • Patent number: 4827067
    Abstract: 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: Grant
    Filed: September 19, 1988
    Date of Patent: May 2, 1989
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Gunther Wilke, Jaroslaw Monkiewicz, Herbert Kuhn
  • Patent number: 4323698
    Abstract: 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: Grant
    Filed: January 21, 1980
    Date of Patent: April 6, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Darrell D. Whitehurst
  • Patent number: 4270016
    Abstract: 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: Grant
    Filed: June 1, 1979
    Date of Patent: May 26, 1981
    Inventors: 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
  • Patent number: 4214108
    Abstract: 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: Grant
    Filed: June 4, 1979
    Date of Patent: July 22, 1980
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventor: Wolfgang Zaar
  • Patent number: 4213901
    Abstract: 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: Grant
    Filed: July 10, 1978
    Date of Patent: July 22, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Dieter Reinehr
  • Patent number: 4187386
    Abstract: 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: Grant
    Filed: December 29, 1978
    Date of Patent: February 5, 1980
    Assignee: Allied Chemical Corporation
    Inventors: George D. Lockyer, Jr., Dennis E. Burd, Richard F. Sweeney, Bernard Sukornick, Harry E. Ulmer
  • Patent number: 4166076
    Abstract: 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: Grant
    Filed: January 16, 1978
    Date of Patent: August 28, 1979
    Assignee: Shell Oil Company
    Inventors: Cornelis F. Roobeek, Petrus W. N. M. VAN Leeuwen