By Condensation, E.g., Diels-alder Reaction, Etc. Patents (Class 585/361)
  • Publication number: 20140364665
    Abstract: Apparatuses, systems and methods for producing Pips stream for manufacturing catalytic C5 hydrocarbon resins containing all the key reactive monomers that are already present in the C5 fraction of the pyrolysis gasoline, which is otherwise lost with the crude isoprene stream, are disclosed herein. Embodiments of the invention are directed to producing a hydrocarbon resin grade DCPD stream consisting of dimers and codimers of isoprene which are of value in manufacturing thermal hydrocarbon resins, either polymer grade isoprene and gasoline quality raffinate (free or sulfur and acetylenes) or a relatively small crude isoprene stream with maximum utilization of isoprene by moving some of the isoprene to a DCPD stream used to manufacture thermal hydrocarbon resins.
    Type: Application
    Filed: June 5, 2014
    Publication date: December 11, 2014
    Applicant: GTC Technology US LLC
    Inventors: Venkata K. Ramanujam, B. Bryant Slimp, JR., Cole Nelson, Michael McCaulley
  • Patent number: 8704022
    Abstract: Embodiments of the present invention are directed generally to methods for producing high purity exo-alkenylnorbornenes from a mixture of conformational isomers thereof.
    Type: Grant
    Filed: August 6, 2008
    Date of Patent: April 22, 2014
    Assignee: Promerus, LLC
    Inventors: Andrew Bell, Dane Jablonski, Elaine Koronich, Brian Knapp, Dino Amoroso
  • Patent number: 8227651
    Abstract: An effective method for producing high density fuel candidates from pinenes is provided. MMT-K10 is an efficient catalyst for the reaction, although significant amounts of p-cymene and camphene produced as byproducts limit the overall yield to about 80%. Nafion is also an excellent catalyst for pinene dimerization and was capable of producing dimers in up to 90% yield. Pinene dimers synthesized with these heterogenous catalysts have a density and net heat of combustion comparable to JP-10. It is emphasized that this abstract is provided to comply with the rules requiring an abstract that will allow a searcher or other reader to quickly ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope of the claims.
    Type: Grant
    Filed: August 31, 2009
    Date of Patent: July 24, 2012
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Michael E. Wright, Roxanne L. Quintana
  • Patent number: 7696370
    Abstract: The invention provides processes for converting a vegetable oil to a polymer. In particular, the processing steps comprise bodying, epoxidation, hydrolysis, and oligomerization. These processes provide new processing paths for the formation of polyols for use in rigid foam and other applications.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: April 13, 2010
    Assignee: The Curators of the University of Missouri
    Inventors: Galen Suppes, Fu-hung Hsieh, Yuan-Chan Tu, Pimphan Kiatsimkul
  • Patent number: 7691159
    Abstract: A triglyceride-to-fuel conversion process including the steps of (a) preconditioning unsaturated triglycerides by catalytic conjugation, cyclization, and cross-link steps; (b) contacting the modified triglycerides with hot-compressed water containing a catalyst, wherein cracking, hydrolysis, decarboxylation, dehydration, aromatization, or isomerization, or any combination thereof, of the modified triglycerides produce a crude hydrocarbon oil and an aqueous phase containing glycerol and lower molecular weight molecules, and (c) refining the crude hydrocarbon oil to produce various grades of biofuels.
    Type: Grant
    Filed: September 19, 2007
    Date of Patent: April 6, 2010
    Assignee: Applied Research Associates, Inc.
    Inventor: Lixiong Li
  • Publication number: 20090112033
    Abstract: [Problem] To provide a trimethylenenorbornane production process capable of producing trimethylenenorbornane, which serves as a raw material of adamantane, with a high efficiency in a raffinate or a heavy raffinate heavy, through high efficiency production of dicyclopentadiene, which serves as a raw material of trimethylenenorbornane, without additionally using a dicyclopentadiene hydrogenation unit or a cyclopentadiene dimerization column.
    Type: Application
    Filed: May 9, 2007
    Publication date: April 30, 2009
    Applicant: IDEMITUS KOSAN CO., LTD.
    Inventor: Noriaki Hosotani
  • Patent number: 7442290
    Abstract: Mesoporous aluminum oxides with high surface areas have been synthesized using inexpensive, small organic templating agents instead of surfactants. Optionally, some of the aluminum can be framework-substituted by one or more other elements. The material has high thermal stability and possesses a three-dimensionally randomly connected mesopore network with continuously tunable pore sizes. This material can be used as catalysts for dehydration, hydrotreating, hydrogenation, catalytic reforming, steam reforming, amination, Fischer-Tropsch synthesis and Diels-Alder synthesis, etc.
    Type: Grant
    Filed: March 21, 2007
    Date of Patent: October 28, 2008
    Assignee: Lummus Technology Inc.
    Inventors: Zhiping Shan, Jacobus Cornelius Jansen, Chuen Y. Yeh, Philip J. Angevine, Thomas Maschmeyer
  • Patent number: 7064225
    Abstract: The present invention provides a method of making compounds comprising linked cyclopentadienyl and fluorenyl groups, including substituted analogs thereof, which are precursors to ansa-metallocenes comprising bridged cyclopentadienyl and fluorenyl ligands. In one aspect, this invention provides a preparative method for (5-cyclopentadienyl)[5-(2,7-di-tert-butylfluorenyl)]hex-1-ene, and ansa-metallocenes comprising this ligand.
    Type: Grant
    Filed: June 25, 2004
    Date of Patent: June 20, 2006
    Assignee: Chevron Phillips Chemical Company, L.P.
    Inventors: Matthew G. Thorn, Joel L. Martin, Qing Yang, Albert P. Masino
  • Patent number: 7041331
    Abstract: Compositions suitable for use as underfill materials in an integrated circuit assembly are provided. Also provided are methods of preparing integrated circuit assemblies containing certain underfill materials as well as electronic devices containing such integrated circuit assemblies.
    Type: Grant
    Filed: April 2, 2004
    Date of Patent: May 9, 2006
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Angelo A. Lamola, Nathaniel E. Brese
  • Publication number: 20030144562
    Abstract: The present invention describes organic solvent-soluble Diels-Alder adducts of polycyclic aromatic compounds, such as, oligothiophene, perylene, benzo[ghi]perylene, coronene and polyacenes, with variety of dienophiles containing at least one heteroatom and in some cases two heteroatoms bonded to aromatic moiety, such as, thioxomalonates, azodicarboxylates, thialdehyde, acylnitroso and N-sulfinylamides. The Diels-Alder adducts are prepared by a simple, one step cycloaddition reaction of the polycyclic aromatic compounds, such as, pentacene, or other fused aromatic compounds, with heterodienophiles. The Diels-Alder adducts according to the present invention all form soluble adducts with pentacene and can be converted back to pentacene by retro-Diels-Alder reaction at moderate (60-250° C.) temperatures both in bulk, in solution or as thin-films.
    Type: Application
    Filed: November 20, 2002
    Publication date: July 31, 2003
    Applicant: International Business Machines Corporation
    Inventors: Ali Afzali-Ardakani, Tricia L. Breen, Christos D. Dimitrakopoulos
  • Patent number: 6579419
    Abstract: For the purification of the norbornene obtained by the reaction of dicyclopentadiene or cyclopentadiene and ethylene, the crude reaction mixture containing light impurities having boiling temperatures lower than that of norbornene; medium-heavy impurities having the boiling temperatures between that of norbornene and that of ethylnorbornene; and heavy impurities containing ethylnorbornene and compounds boiling higher than ethylnorbornene, boiling temperatures greater than that ethylnorbornene, a first distillation of the crude reaction mixture is carried out in a tailing column (C1), removing a portion of the heavy impurities and a portion of the medium-heavy impurities; then a second distillation of the crude mixture, thus tailed, is carried out in a topping column (C2), removing the light impurities; and a third distillation of the mixture, thus topped, is subsequently carried out in a tailing column (C3), removing the remainder of the heavy and medium-heavy impurities.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: June 17, 2003
    Assignee: Elf Atochem, S.A.
    Inventors: Roland Kotwica, André Marbach
  • Patent number: 6566570
    Abstract: A process for producing an unsaturated cyclic compound, comprising the steps of hydrochlorinating a terpene to produce a hydrochlorinated terpene, and subjecting the hydrochlorinate terpene to elimination of hydrogen chloride to form an unsaturated cyclic compound. The terpene is preferably &agr;-pinene, &bgr;-pinene, camphene or suitable turpentine fraction. The cyclic compounds can be used as monomers and by means of the invention it is thus possible to produce plastics from renewable raw material sources.
    Type: Grant
    Filed: August 4, 2000
    Date of Patent: May 20, 2003
    Assignee: Optatech Corporation
    Inventors: Christer Bergström, Arto Mölsä, Juhana Ruotoistenmäki
  • Patent number: 6559347
    Abstract: Diels-Alder adducts of dienophiles such as epoxybutene with dienes such as cyclopentadiene and cyclohexadiene are produced by carrying out the Diels-Alder reaction thereof at an elevated pressure. Addional dienophiles disclosed include 2,5-dihydrofuran and derivatives thereof; Additional dienes include isoprene and butadiene. Compounds produced from such reactions are also disclosed.
    Type: Grant
    Filed: February 8, 2002
    Date of Patent: May 6, 2003
    Assignee: Wake Forest University Health Sciences
    Inventors: Mark E. Welker, Marion A. Franks
  • Publication number: 20030045762
    Abstract: The invention relates to economical and efficient methods for producing 2-methylene-3-methylbicyclo[2,2,1]heptane, 2,3-dimethylbicyclo[2.2.1]hept-2-ene and the like that are useful for materials of producing base oil of traction drive fluid for traction drive lubricating oil. The methods comprise reacting one or more C3-4 acyclic olefins with cyclopentadiene and isomerizing the resulting bicyclo[2.2.1]heptene derivatives in the presence of an isomerization catalyst to give one or more bicyclo[2.2.1]heptane derivatives.
    Type: Application
    Filed: July 25, 2002
    Publication date: March 6, 2003
    Inventors: Toshiyuki Tsubouchi, Yukio Yoshida, Motohisa Ido, Masahiro Katayama
  • Patent number: 6512152
    Abstract: The present invention is drawn to a tetracyclododecene composition having a regulated cyclopentadiene trimer content, whereby addition polymerization with the aid of a Ziegler catalyst can be carried out while preventing gelation caused by a cross-linking reaction. A tetracyclododecene composition regulated with respect to the content of a specific ingredient having a molecular weight of 188 is disclosed, whereby polymers having high glass transition temperatures can be obtained through various polymerizations. Further, the present invention is drawn to a method for producing tetracyclododecene in the presence of an aliphatic solvent having a boiling point close to that of norbornene, which solvent is effective in inhibiting the recovered norbornene from solidifying.
    Type: Grant
    Filed: February 28, 2000
    Date of Patent: January 28, 2003
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Masaki Hashizume, Tomonobu Uchida, Fuyuki Aida, Takashi Suzuki, Yoshihisa Inomata, Yasuo Matsumura
  • Publication number: 20020156334
    Abstract: A process for simultaneously producing a purified dicyclopentadiene and 5-ethylidene-2-norbornene from a crude dicyclopentadiene and 1,3-butadiene, which comprises the following steps of:
    Type: Application
    Filed: March 25, 2002
    Publication date: October 24, 2002
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Tateo Seo
  • Patent number: 6465703
    Abstract: The present invention relates to a process for the preparation of tetracyclododecenes, which can be a raw material of cycloolefin (co)polymers possessing excellent characters concerning their optical property, high transparency, heat resistance, and oil absorbency, from an inexpensive raw material of crude DCPD in a stable, continuous, and longstanding process. In the continuous preparation of tetracyclododecenes described in the present invention, it is possible to produce the targeted product in high efficiencies in the effective utilization of the raw materials exemplified by the separation and recovery of 2-norbornenes after the reaction. It is also possible to maintain a stable, continuous, and longstanding operation based on the suppression of ill effects deriving from the accumulation of byproducts such as 2-methyl-2-norbornenes, which easily creep into the circulating 2-norbornenes, by removing at least a part of said products from the reaction system.
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: October 15, 2002
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Fuyuki Aida, Takashi Suzuki, Yasuo Matsumura
  • Publication number: 20020119391
    Abstract: Disclosed are polymers containing as polymerized units one or more cyclic olefin monomers having fused cyclic electron withdrawing groups, methods of preparing such polymers, photoresist compositions including such polymers as resin binders and methods of forming relief images using such photoresist compositions.
    Type: Application
    Filed: February 23, 2001
    Publication date: August 29, 2002
    Applicant: Shipley Company, L.L.C.
    Inventors: George G. Barclay, Anthony Zampini
  • Patent number: 6441259
    Abstract: The present invention relates to a process for the preparation of highly purified tetracyclododecenes, which can be a raw material of cycloolefin (co)polymers possessing excellent characters concerning their optical property, high transparency, heat resistance, and oil absorbency, from an inexpensive raw material of crude DCPD in a stable, continuous, and longstanding process. In the continuous preparation of tetracyclododecenes described in the present invention, it is possible to employ crude dicyclopentadiene, that is, dicyclopentadiene having low purity, as a raw material. It is also possible to produce highly purified tetracyclododecenes by maintaining the ratios of one, two, or three compounds selected from the group comprising isoprene, piperylene, and 1-methyl-2-norbornenes shown by the general formula (4) against the sum of dicyclopentadiene and cyclopentadiene within the specified ranges, wherein all these substances are contained in the raw material that are fed into a reactor.
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: August 27, 2002
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Fuyuki Aida, Takashi Suzuki, Yasuo Matsumura
  • Patent number: 6380447
    Abstract: Diels-Alder adducts of dienophiles such as epoxybutene with dienes such as cyclopentadiene and cyclohexadiene are produced by carrying out the Diels-Alder reaction thereof at an elevated pressure. Addional dienophiles disclosed include 2,5-dihydrofuran and derivatives thereof; Additional dienes include isoprene and butadiene. Compounds produced from such reactions are also disclosed.
    Type: Grant
    Filed: June 9, 2000
    Date of Patent: April 30, 2002
    Assignee: Wake Forest University
    Inventors: Mark E. Welker, Marion A. Franks
  • Patent number: 6294706
    Abstract: Disclosed is a method for the preparation of norbornene and substituted norbornene compounds via a Diels-Alder reaction, in which a cyclic diene is reacted with an olefinic compound in order to prepare a norbornene compound. According to the invention a cyclic diene is gradually added to react with an olefinic compound, in order to keep the concentration of the cyclic diene in the reaction mixture as low as possible during the reaction. It is possible to obtain a very pure product, high yield, short reaction time and high concentrations of the exo diastereomer with the method of the invention.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: September 25, 2001
    Assignee: Opatatech Corporation
    Inventors: Christer Bergström, Jukka Koskinen, Erkki Halme, Matti Lindström, Mika Perälä
  • Patent number: 6268518
    Abstract: It is disclosed a new class of bridged metallocene compounds of formula (I): wherein R1 and R2 can be hydrogen, alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl radicals; R3 and R4 form a condensed, 5- to 8-membered, aliphatic, aromatic or heterocyclic ring; M is a transition metal of groups 3, 4, 5, lanthanide or actinide; X is hydrogen, halogen, —R, —OR, —OSO2CF3, —OCOR, —SR, —NR2 or PR2, wherein R is an hydrocarbon substituent; and p is 0-3. Furthermore, a catalyst system for olefin polymerization based on the above bridged metallocene compounds and the ligands for their preparation are disclosed.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: July 31, 2001
    Assignee: Montell Technology Company B.V.
    Inventors: Luigi Resconi, Davide Balboni, Vu Anh Dang, Lin-Chen Yu
  • Publication number: 20010004510
    Abstract: Novel silicon-containing polymer compounds, based on cyclic olefins. These polymer compounds can be used as photoresist materials and because they are transparent to radiation in the spectral range from 193 to 13 nm, which is highly energetic and strongly attenuated, are particularly advantageous as refractory bilayer photoresist materials for semiconductor wafer patterning processes that employ deep ultraviolet (DUV) and extreme ultraviolet (EUV) radiation.
    Type: Application
    Filed: December 19, 2000
    Publication date: June 21, 2001
    Inventor: David R. Wheeler
  • Patent number: 6093865
    Abstract: 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: Grant
    Filed: June 16, 1998
    Date of Patent: July 25, 2000
    Assignee: Exxon Chemical Patent Inc.
    Inventors: James R. Lattner, Leonel E. Sanchez, Christopher L. Becker, Bruce C. Devoy
  • Patent number: 5973085
    Abstract: Compounds of the formula I(A).sub.n --B (I)in which A is the radical of a strained cycloolefin, B is a direct bond or an n-valent bridging group and n is an integer from 2 to 8, with the exception of 1,2-bisnorbornenyl-ethane and norbornenecarboxylic acid norbornenemethyl ester. The compounds of the formula I can be polymerized with one-component catalysts (ring-opening metathesis polymerization).
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: October 26, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Andreas Muhlebach, Andreas Hafner, Paul Adriaan Van Der Schaaf
  • Patent number: 5945553
    Abstract: Process for preparing a methylene-bridged cyclopentadienyl compoundThe present invention relates to a process for preparing a methylene-bridged biscyclopentadienyl compound having the formula I ##STR1## Where L are, independently of one another, identical or different and are each a cyclopentadienyl group, by reactin one or two cyclopentadienyl compounds LH with formaldehyde in monomeric, oligomeric or polymeric form or formaldehyde-generating reagents in the presence of at least one base and at least one phase transfer catalyst.
    Type: Grant
    Filed: September 12, 1997
    Date of Patent: August 31, 1999
    Assignee: Targor GmbH
    Inventors: Frank Kuber, Michael Riedel, Berthold Schiemenz
  • Patent number: 5847247
    Abstract: The specification discloses terpene-based solvent compositions which comprise diterpenes as a major component and a minor amount of monoterpenes. The mixtures exhibit solvent properties similar to monoterpenes but have flash points high enough to be classified as combustible rather than flammable materials.
    Type: Grant
    Filed: March 18, 1996
    Date of Patent: December 8, 1998
    Assignee: Arizona Chemical Company
    Inventors: Alexander J. Conte, Bobby G. Johnson, Raymond H. Jones, Claude F. Phillips, Jr.
  • Patent number: 5723709
    Abstract: Terpene dimer compositions are provided which dry into a hard, tack free film upon exposure to air. The compositions include a terpene dimer having the molecular formula C.sub.20 H.sub.32 and contain at least one double bond. The terpene dimer is derived from a naturally occurring monoterpene, or mixtures thereof, having the molecular formula C.sub.10 H.sub.16. In an another embodiment the compositions, in addition to the terpene dimer, include isomers of the monoterpenes. The compositions are substantially free of higher terpene oligomers having molecular formulas greater than C.sub.20 H.sub.32. Processes for making the terpene dimer compositions are also provided. Advantageous utilization of these compositions is as a diluent, solvent or component in coating, adhesive, alkyd or ink formulations, as an environmentally safe non-toxic material.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: March 3, 1998
    Assignee: Arizona Chemical Company
    Inventors: Claude Frank Phillips, Jr., James William Booth
  • Patent number: 5670681
    Abstract: The present invention relates to a process for preparing a carbon-bridged biscyclopentadiene compound by reacting one or two cyclopentadiene compounds LH with a carbonyl compound in the presence of at least one base and at least one phase transfer catalyst.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: September 23, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Frank Kuber, Michael Riedel
  • Patent number: 5600047
    Abstract: A process for producing an optically active olefin represented by a formula ##STR1## wherein R.sup.1 represents an organic group and X represents a polycyclic carbon ring group, by reacting a corresponding optically active ester derivative represented by a formula ##STR2## wherein R.sup.1 and X are as defined above and R represents a hydrogen atom, an alkoxy group, an alkenyloxy group or a substituted or unsubstituted aralkyloxy group, with formic acid or a salt thereof in the presence of a catalyst comprising a palladium salt and a tertiary phosphine.Said process makes it possible to produce, at a high yield at a high selectivity, an optically active olefin which has a physiological activity and is useful as a medicine or is useful as an intermediate for the synthesis of physiologically active steroids. Further, said process uses no harmful reagent such as mercury or the like. Thus, it is advantageous as an industrial process.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: February 4, 1997
    Assignee: Kuraray Co., Ltd.
    Inventors: Tadakatsu Mandai, Jiro Tsuji, Manzo Shiono
  • Patent number: 5581004
    Abstract: The magnesium complexes of cyclic hydrocarbons and conjugated dienes, such as 1,2-dimethylenecycloalkanes and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.-lactones, including spiro .
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: December 3, 1996
    Assignee: Board of Regents of the University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5569804
    Abstract: 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: Grant
    Filed: December 30, 1993
    Date of Patent: October 29, 1996
    Assignee: Exxon Chemical Patents Inc (ECPI)
    Inventors: James R. Lattner, Leonel E. Sanchez
  • Patent number: 5565069
    Abstract: 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: Grant
    Filed: May 26, 1995
    Date of Patent: October 15, 1996
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Nobuo Oi, Kazuo Kimura, Kenichi Nariyama
  • 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: 5545790
    Abstract: A catalytic process for the dimerization of norbornene and/or norbornadiene using a reduced valence state Group VIB metal oxide as the catalyst, preferably Cr(II) on a porous support such as silica. The product norbornene dimer or norbornadiene dimer is obtained in high yield and high stereospecificity at greater than 90 weight percent of the exo-trans-exo stereoisomer. The norbornene dimer is useful as a high energy density fuel. The norbornadiene dimer can be further functionalized to yield novel chemical intermediates or polymerized or copolymerized with other olefins. The norbornadiene dimer can also be hydrogenated for high energy fuel applications.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: August 13, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Margaret M. Wu, Yusheng Xiong
  • Patent number: 5498734
    Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5446222
    Abstract: The invention provides a two-step process for converting cyclopentadiene dimer to a high density fuel mixture comprising the steps of:(a) reacting said cyclopentadiene dimer in the presence of a solid catalyst comprising a porous crystalline material having a Constraint Index of from about 0.1 to about 12 under oligomerization/isomerization conditions to convert at least a portion of said cyclopentadiene dimer to a normally liquid intermediate product containing cyclopentadiene trimer, cyclopentadiene tetramer, and the isomerized and oligomerized products derived from the reaction of at least three cyclopentadiene monomer units;(b) hydrogenating said normally liquid intermediate product of step (a) in the presence of a hydrogenation catalyst to form a normally liquid high energy density fuel.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: August 29, 1995
    Assignee: Mobil Oil Corporation
    Inventors: James R. Boulton, Ross A. Kremer
  • Patent number: 5329057
    Abstract: 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: Grant
    Filed: September 30, 1992
    Date of Patent: July 12, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ronald W. Diesen, Kenneth A. Burdett, Ravi S. Dixit, Stanley S. T. King
  • Patent number: 5324876
    Abstract: Small catalytic amounts of a transition metal catalyst such as Cr(O) are used in a higher order cycloaddition process in which a triene is reacted with a diene or alkene to efficiently and economically provide a cycloaddition product.
    Type: Grant
    Filed: August 19, 1993
    Date of Patent: June 28, 1994
    Assignee: Wayne State University
    Inventor: James H. Rigby
  • Patent number: 5310931
    Abstract: This invention is to provide a novel process for the isomerization of a cycloolefin having an endo form to a cycloolefin having an exo form. The resulting isomer mixture has a novel composition, and a random copolymer produced from the above compositionally novel isomer mixture and ethylene has an excellent heat resistance and mechanical strength.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: May 10, 1994
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Toshihiro Sagane, Hideaki Yamaguchi, Shuji Minami, Akira Mizuno, Hiroo Wamura
  • Patent number: 5260498
    Abstract: An improved process for the production of 1:1 molar adducts of 4-vinylcyclohexene and cyclopentadiene, primarily 5-(3-cyclohexen-1-yl)-2-norbornene, comprises contacting 4-vinylcyclohexene and dicyclopentadiene at elevated temperature in a suitable reactor, separating the resulting mixture of adducts into light product comprising predominately the 1:1 molar adduct and a heavy product comprising higher adducts and cyclopentadiene oligomers, and recycling the bottoms product to the reactor.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: November 9, 1993
    Assignee: Shell Oil Company
    Inventor: Robert H. Ellison
  • Patent number: 5231205
    Abstract: The magnesium complexes of cyclic hydrocarbons, such as 1,2-dimethylenecycloalkanes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4-diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, or bromoalkylnitriles serve as a convenient method for synthesizing spirocyclic systems. Significantly, spirocarbocycles prepared by thisThe present invention was made with Government support under Contract No. GM35153 awarded by the National Institute of Health. The Government has certain rights in the invention.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: July 27, 1993
    Assignee: Board of Regents of the University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5196621
    Abstract: 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: Grant
    Filed: April 19, 1991
    Date of Patent: March 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: Ronald W. Diesen, Kenneth A. Burdett, Ravi S. Dixit, Stanley S. T. King, Michael M. Olken
  • Patent number: 5143992
    Abstract: An improved thermoset polymer having good mechanical properties and no detectable dicyclopentadiene odor is obtained by the ring-opening polymerization of a novel mixture of adducts comprising divinyl cyclohydrocarbon compound, such as 3,5-divinylcyclopentene and cyclopentadiene, optionally with added cycloolefinic compound, such as dicyclopentadiene, at polymerization conditions in the presence of an olefin metathesis catalyst.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: September 1, 1992
    Assignee: Shell Oil Company
    Inventor: Donald R. Kelsey
  • Patent number: 5095082
    Abstract: A hard, infusible, crosslinked polymeric product free from detectable cyclopentadiene odor is obtained by contacting, under polymerization conditions, a mixture of Diels-Alder adducts of 4-vinylcyclohexene and cyclopentadiene and Diels-Alder oligomers of cyclopentadiene of at least 3 cyclopentadiene units with an olefin methathesis catalyst.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: March 10, 1992
    Assignee: Shell Oil Company
    Inventor: Donald R. Kelsey
  • Patent number: 5068296
    Abstract: A cross-linked copolymer containing repeating units derived from a mixture comprising the following monomers: ##STR1## and occasionally other repeating units derived from other metathesis polymerizable cyclic compounds such as dicyclopentadiene, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: November 26, 1991
    Assignee: Hercules Incorporated
    Inventors: Shigeyoshi Hara, Zen-ichiro Endo, Hiroshi Mera
  • Patent number: 5006616
    Abstract: A cross-linked copolymer containing repeating units derived from a mixture comprising the following monomers: ##STR1## and occasionally other repeating units derived from other metathesis polymerizable cyclic compounds such as dicyclopentadiene, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: April 9, 1991
    Assignee: Hercules Incorporated
    Inventors: Shigeyoshi Hara, Zen-ichiro Endo, Hiroshi Mera
  • Patent number: 4912274
    Abstract: The invention relates to azaphospholenes 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: July 26, 1989
    Date of Patent: March 27, 1990
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Gunther Wilke, Jaroslaw Monkiewicz, Herbert Kuhn
  • Patent number: 4873349
    Abstract: A method for forming bridged biaryl compounds via the intramolecular oxidative biarylic coupling of precursor compounds containing two aromatic rings linked via a hydrocarbon chain is disclosed along with the ruthenium catalyst for its implementation and new compounds resulting therefrom. The biarylic coupling method is characterized in that the biarylic precursors are cyclized in the presence of the catalyst tetrakis(trifluoroacetate) of ruthenium (IV).
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: October 10, 1989
    Assignee: Universite Du Maine (Le Mans)
    Inventors: Jean-Pierre Robin, Yannick Landais
  • Patent number: 4804795
    Abstract: The present invention provided a high-density fuel oil comprising an isomerized product prepared by isomerizing an alicyclic saturated hydrocarbon represented by the following formula in the presence of an acid catalyst: ##STR1## wherein each of m and n is 0 or 1, and each of R.sup.1 to R.sup.3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, but the number of the total carbons of R.sup.1 to R.sup.3 is within the range of 1 to 3.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: February 14, 1989
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Hirosuke Imai