Polycyclic Product Patents (Class 585/360)
  • Patent number: 8969641
    Abstract: Tetrahydrotricyclopentadienes are isomerized to a low pour point, high energy missile fuel. Aluminum trichloride is the catalyst and an inert chlorinated hydrocarbon solvent is present. The mole ratio of AlCl3 to the diene is in the range between from about 0.005 to about 1.0. The isomerization temperature is in the range from between about ?20° C. to about 25° C.
    Type: Grant
    Filed: September 3, 1976
    Date of Patent: March 3, 2015
    Inventors: Richard E. Ware, Edward J. Janoski, Abraham Schneider
  • Patent number: 8735521
    Abstract: A cycloolefin-based copolymer and a hydrogenation process are disclosed, wherein the cycloolefin-based copolymer is prepared by using: a monomer which can be easily and economically obtained by hydrogenating dicyclopentadiene that occupies much of C5 fractions from naphtha cracking; or a monomer which can be obtained by chemically bonding three molecules of cyclopentadiene via Diels-Alder reactions and then hydrogenating the cyclopentadiene. The copolymer can be used in various fields as an amorphous transparent resin.
    Type: Grant
    Filed: February 11, 2009
    Date of Patent: May 27, 2014
    Assignee: Kolon Industries, Inc.
    Inventors: Ik Kyung Sung, Woon Sung Hwang, Jung Hoon Seo, Bun Yeoul Lee, Sung Jae Na, Seung Taek Yu
  • 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: 8642815
    Abstract: The present invention is directed to novel methods for production of 5-epi-?-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethylspiro[4.5]deca-1,6-dien-8-one, which are useful for their fragrant qualities. Provided are methods for production of premnaspirodiene from a terpene substrate, methods for production of 5-epi-?-vetivone from premnaspirodiene as starting material, and methods for production of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one from premnaspirodiene as starting material.
    Type: Grant
    Filed: December 13, 2012
    Date of Patent: February 4, 2014
    Assignee: Allylix, Inc.
    Inventors: Bryan N. Julien, David M. Wallace
  • Patent number: 8524930
    Abstract: This invention relates to a metathesis catalyst comprising a Group 8 metal complex represented by the formula: wherein: M is a Group 8 metal; each X is independently an anionic ligand; R1 and R2 are independently selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; R3 and R4 are independently selected from the group consisting of hydrogen, C1 to C12 hydrocarbyl groups, substituted C1 to C12 hydrocarbyl groups, and halides; and L is a neutral donor ligand. This invention also relates to processes for performing a metathesis reaction, in particular ring opening cross metathesis reactions and ring opening metathesis polymerization reactions, using the Group 8 metal complexes.
    Type: Grant
    Filed: May 31, 2011
    Date of Patent: September 3, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Matthew W. Holtcamp, Matthew S. Bedoya
  • Patent number: 8362309
    Abstract: The present invention is directed to novel methods for production of 5-epi-?-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethylspiro[4.5]deca-1,6-dien-8-one, which are useful for their fragrant qualities. Provided are methods for production of premnaspirodiene from a terpene substrate, methods for production of 5-epi-?-vetivone from premnaspirodiene as starting material, and methods for production of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one from premnaspirodiene as starting material.
    Type: Grant
    Filed: January 30, 2012
    Date of Patent: January 29, 2013
    Assignee: Allylix, Inc.
    Inventors: Bryan N. Julien, David M. Wallace
  • Publication number: 20120309998
    Abstract: This invention relates to a metathesis catalyst comprising a Group 8 metal complex represented by the formula: wherein: M is a Group 8 metal; each X is independently an anionic ligand; R1 and R2 are independently selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; R3 and R4 are independently selected from the group consisting of hydrogen, C1 to C12 hydrocarbyl groups, substituted C1 to C12 hydrocarbyl groups, and halides; and L is a neutral donor ligand. This invention also relates to processes for performing a metathesis reaction, in particular ring opening cross metathesis reactions and ring opening metathesis polymerization reactions, using the Group 8 metal complexes.
    Type: Application
    Filed: May 31, 2011
    Publication date: December 6, 2012
    Inventors: Matthew W. HOLTCAMP, Matthew S. BEDOYA
  • Patent number: 8269054
    Abstract: The present invention relates to an improved process for producing tetra-hydro alkyl substituted indanes which are used in the synthesis of fragrance ingredients for perfumery applications.
    Type: Grant
    Filed: November 19, 2009
    Date of Patent: September 18, 2012
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Sunitha Rao Tadepalli, Geatesh Karunakaran Tampy
  • 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: 8188326
    Abstract: A method for producing adamantane by performing an isomerization reaction in two stages using endo-tetrahydrodicyclopentadiene and/or exo-tetrahydrodicyclopentadiene as a starting material, wherein in a first-stage isomerization reaction from endo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane) to exo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane), an HF catalyst alone or two catalysts of an HF catalyst and a BF3 catalyst are used in the absence of a solvent; and in a second-stage isomerization reaction from exo-tetrahydrodicyclopentadiene (tricyclo[5.2.1.02,6]decane) to adamantane (tricyclo[3.3.1.13,7]decane), an HF catalyst and a BF3 catalyst are used in the absence of a solvent.
    Type: Grant
    Filed: May 7, 2009
    Date of Patent: May 29, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takeshi Kawai, Mitsuharu Kitamura
  • Publication number: 20110178349
    Abstract: A method of treating a hydrocarbon stream comprising cyclopentadiene (CPD) and one or more diolefins, the method comprising: providing a hydrocarbon stream comprising an initial CPD concentration, an initial target diolefin concentration, and an initial secondary diolefin concentration; subjecting the hydrocarbon stream to preseparation conditions effective to separate (a) a crude target diolefin feedstock having a decreased concentration of CPD and an increased target diolefin concentration, and (b) a CPD dimerization feedstock having a decreased target diolefin concentration and an increased CPD concentration that is 1.5 or more times the initial CPD concentration; subjecting the CPD dimerization feedstock to CPD dimerization conditions effective to produce a raw DCPD stream comprising 20 wt. % or more DCPD; and, separating a high purity DCPD product stream comprising 90 wt. % or more DCPD from the raw DCPD stream.
    Type: Application
    Filed: December 15, 2010
    Publication date: July 21, 2011
    Inventors: Robert Kenneth ANZICK, Robert Lawrence BLACKBOURN, SivaKumar NAYARAJAN
  • Publication number: 20110118519
    Abstract: The present invention relates to an improved process for producing tetra-hydro alkyl substituted indanes which are used in the synthesis of fragrance ingredients for perfumery applications.
    Type: Application
    Filed: November 19, 2009
    Publication date: May 19, 2011
    Inventors: Sunitha Rao Tadepalli, Geatesh Karunakaran Tampy
  • Publication number: 20110077440
    Abstract: The present invention relates to an improved process for producing alkyl substituted indanes which are used in the synthesis of fragrance ingredients for perfumery applications.
    Type: Application
    Filed: September 28, 2009
    Publication date: March 31, 2011
    Inventors: Adeniyi Lawal, Obiefuna C. Okafor, Sunitha Rao Tadepalli, Geatesh Karunakaran Tampy
  • Patent number: 7863488
    Abstract: A method comprising reducing an acenequinone to form an acenepolyhydrodiol by exposing the acenequinone to a reducing environment comprising an alkoxyaluminate.
    Type: Grant
    Filed: February 8, 2010
    Date of Patent: January 4, 2011
    Assignees: Alcatel-Lucent USA Inc., Columbia University
    Inventor: Xiaoliu Chi
  • Publication number: 20100317895
    Abstract: In a process for producing cyclohexylbenzene, hydrogen and a liquid feed comprising benzene are introduced into a reaction zone and are contacted in the reaction zone under hydroalkylation conditions to produce cyclohexylbenzene. An effluent stream comprising cyclohexylbenzene and unreacted benzene is removed from the reaction zone and is divided into at least first and second portions, wherein the mass ratio of the effluent stream first portion to the effluent stream second portion is at least 2:1. The effluent stream first portion is then cooled and the cooled effluent stream first portion is recycled to the reaction zone.
    Type: Application
    Filed: January 13, 2009
    Publication date: December 16, 2010
    Inventors: John S. Buchanan, Jane C. Cheng, Tan-Jen Chen, James R. Lattner
  • Publication number: 20100286460
    Abstract: A method for synthesizing exo-tetrahydrodicyclopentadiene (exo-THDCPD) and adamantane is provided, including isomerization of an endo-tetrahydrodicyclopentadiene (endo-THDCPD) as a reaction feed with an acidic ionic liquid of aluminum trichloride in a pseudo-fixed bed ionic liquid reactor. Reactants float as a droplet from bottom to top of the pseudo-fixed bed reactor, and finally are discharged from a side tube. A mole fraction of aluminum trichloride in the acidic ionic liquid of aluminum trichloride is from 0.5 to 0.9, a feeding rate of the reaction feed is 0.1-10 g/min, and a temperature for the isomerization is between 25-120° C.
    Type: Application
    Filed: May 11, 2009
    Publication date: November 11, 2010
    Applicant: CPC Corporation, Taiwan
    Inventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
  • Publication number: 20100249475
    Abstract: A process for isomerization of tetrahydrodicyclopentadiene using a supported acidic ionic liquid as catalyst is provided. In the presence of the supported acidic ionic liquid, endo-tetrahydrodicyclopentadiene is isomerized to exo-tetrahydrodicyclo-pentadiene, wherein the supported acidic ionic liquid includes a porous support and an acidic ionic liquid, and the acidic ionic liquid includes an aluminum halide, and a quaternary ammonium halide or a quaternary phosphonium halide. The porous support is impregnated with the acidic ionic liquid. Furthermore, under different reaction conditions, the exo-tetrahydrodicyclopentadiene product can be isomerized to adamantane in the presence of such a supported acidic ionic liquid.
    Type: Application
    Filed: March 24, 2009
    Publication date: September 30, 2010
    Inventors: Ming-Yu Huang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
  • Patent number: 7803265
    Abstract: A process is disclosed for converting distillate to gasoline-range hydrocarbons using a two-stage catalyst system including a first catalyst containing platinum, palladium, or platinum and palladium, and an acidic support, and a second catalyst containing iridium and an inorganic oxide support, and optionally nickel.
    Type: Grant
    Filed: February 4, 2009
    Date of Patent: September 28, 2010
    Assignee: ConocoPhillips Company
    Inventors: Tushar V. Choudhary, Paul F. Meier, Edward L. Sughrue, II, Walter E. Alvarez
  • Publication number: 20100129306
    Abstract: The present invention is directed to novel methods for production of 5-epi-?-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one, which are useful for their fragrant qualities. In one embodiment the present invention describes a method for production of 5-epi-?-vetivone by the use of premnaspirodiene as starting material. In another embodiment the present invention describes a method for production of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one by the use of premnaspirodiene as starting material. In yet another embodiment the present invention describes a novel method for production of premnaspirodiene from a terpene substrate. Use of the fragrant components or any composition containing the component can be advantageously employed in the perfumery industry.
    Type: Application
    Filed: October 14, 2009
    Publication date: May 27, 2010
    Inventors: Bryan N. Julien, David M. Wallace
  • Publication number: 20100121062
    Abstract: A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1—B-T ??(I); where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.
    Type: Application
    Filed: September 25, 2009
    Publication date: May 13, 2010
    Applicant: The Board of Trustees of the University of Illinois
    Inventors: Martin D. Burke, David M. Knapp, Eric P. Gillis
  • Patent number: 7696396
    Abstract: Carotenoids are extracted and/or enriched from a mixture containing such compounds. The extraction/enrichment process involves the use of liquefied or supercritical solvents to extract lipids and carotenoids from carotenoid-containing substrates. The extraction process can also be performed in two steps in which lipids and carotenoids are first removed from a carotenoid-containing substrate with a liquefied or supercritical solvent, and subsequently a liquefied or supercritical gas is used to separate the lipids from the carotenoids. The two step process can be reversed to first extract lipids with the liquefied or supercritical gas, and subsequently use the solvent to extract the carotenoids. The process is also applicable to yield an organic solvent-free product from a carotenoid-containing source that was first extracted using an organic solvent.
    Type: Grant
    Filed: January 9, 2008
    Date of Patent: April 13, 2010
    Assignee: Phasex Corporation
    Inventors: Hans Schonemann, Anthony Gudinas, Kara Williams, Paula Wetmore, Val Krukonis
  • Patent number: 7683229
    Abstract: The present invention relates to novel truxene and isotruxene derivatives, in particular spirotruxene and spiroisotruxene derivatives, and to the use thereof in organic electronic devices, in particular organic electroluminescent devices.
    Type: Grant
    Filed: July 15, 2005
    Date of Patent: March 23, 2010
    Assignee: Merck Patent GmbH
    Inventors: Philipp Stoessel, Esther Breuning, Liliana Bagala′ Rampazzo, Giulia Fioravanti, Leonardo Mattiello
  • Patent number: 7638662
    Abstract: Compounds of the formula (I): wherein each of R1-R12 is independently hydrogen or a linear C1-20 alkyl group each of A1 and A2 is a 1, 2 or 3 ring carbon atom wherein A1 is substituted by R9 and R10 and A2 is substituted by R11 and R12; and wherein at least one of R1-R12 is a linear alkyl group having from 1 to 20 carbon atoms are emollients for use in cosmetics, lubricants and pharmaceutical preparations.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: December 29, 2009
    Assignee: COGNIS IP Management
    Inventors: Achim Ansmann, Sabine Both, Daniela Prinz, Nicole Schoeffler, Alfred Westfechtel
  • Patent number: 7019183
    Abstract: It is made possible to efficiently produce adamantane and analogues thereof, namely a hydrocarbon having an adamantane structure by a process which comprises isomerizing a tricyclic saturated hydrocarbon having ten or more carbon atoms in the presence of a solid-acid catalyst containing one or two or more metals selected from among the metals belonging to group VIII in the Periodic Table (group 8 to 12 in the new Periodic Table), wherein one or two or more monocyclic saturated hydrocarbons are added to the tricyclic saturated hydrocarbon having ten or more carbon atoms.
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: March 28, 2006
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Akio Kojima, Kouichi Kodoi
  • Publication number: 20030114724
    Abstract: The present invention relates to a novel biopolymer consisting of a three-dimensional cross-linked mixture of (a) a cross-linking agent, activated with an activating agent, dissolved in a aqueous solution, and (b) a recombinant protein, namely polyubiquitin. The novel biopolymer is based on the cross-linking of ubiquitin (monomeric and/or polymeric) with a cross-linking agent, preferably bifunctionalized polyethylene oxides or a polyethylene glycol of various molecular masses (MW 2000 to 35 000 kDa), dissolved in aqueous solution in adequate proportions. The novel biopolymer offers a wide range of formulations since the number of ubiquitin units and cross-linking agent can vary both in length and ratio. The novel hydrogel is also biodegradable by a specific protease and is resistant to a wide range of other proteases.
    Type: Application
    Filed: November 20, 2002
    Publication date: June 19, 2003
    Inventor: Marc Boss
  • 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
  • Publication number: 20030023122
    Abstract: It is made possible to efficiently produce adamantane and analogues thereof, namely a hydrocarbon having an adamantane structure by a process which comprises isomerizing a tricyclic saturated hydrocarbon having ten or more carbon atoms in the presence of a solid-acid catalyst containing one or two or more metals selected from among the metals belonging to group VIII in the Periodic Table (group 8 to 12 in the new Periodic Table), wherein one or two or more monocyclic saturated hydrocarbons are added to the tricyclic saturated hydrocarbon having ten or more carbon atoms.
    Type: Application
    Filed: August 7, 2002
    Publication date: January 30, 2003
    Inventors: Akio Kojima, Kouichi Kodoi
  • 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
  • Patent number: 6479719
    Abstract: This process for the manufacture of norbornene from dicyclopentadiene (DCPD) and ethylene is characterized in that the DCPD is subjected to partial monomerization to CPD by preheating: at a temperature of 140° C. to 240° C.; and under a pressure of 20 to 300 bar abs., before reacting it with the ethylene; with an ethylene/DCPD molar ratio of 1 to 20; at a temperature of 200° C. to 320° C.; under a pressure of 20 to 300 bar abs.; and with a residence time of 1 to 10 minutes, under stable reaction conditions between the DCPD, the CPD and the ethylene.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: November 12, 2002
    Assignee: Atofina
    Inventors: Roland Kotwica, André Marbach
  • 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: 6417405
    Abstract: Substituted or unsubstituted cyclopentadienyl are prepared by reducing 4-ketocyclopentene to an alcohol, replacing the hydroxyl functionality with a leaving group and deprotonating the resulting product under base induced elimination conditions.
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: July 9, 2002
    Assignee: The Dow Chemical Company
    Inventor: Ravi B. Shankar
  • Patent number: 6414206
    Abstract: The present invention relates to a process for preparing bisindenylalkanes of formula I: wherein R1, R2, R3, and R4 independently represent H or a C1-C6 hydrocarbon group or R1 and R2 or R1 and R3 or R3 and R4 together with the carbon atoms to which they are attached form a saturated or unsaturated 5- or 6-membered ring, said ring being optionally substituted with a C1-C4 hydrocarbon group, and R5 represents a C1-C6 hydrocarbon group, comprising reacting, at a temperature which does not exceed about 5° C., a metallated indene of formula II with a disubstituted hydrocarbon of formula III: wherein R1, R2, R3, R4, and R5 have the same meaning as defined above, M represents a metal ion, and X independently represents a suitable leaving group, in a suitable reaction medium wherein the molar ratio of II to III is 2.05 or higher. The process is particularly suitable for preparing bisindenylethane, i.e., R1-R4 represent H and R5 represents an ethylene group.
    Type: Grant
    Filed: February 22, 2001
    Date of Patent: July 2, 2002
    Assignee: Akzo Nobel NV
    Inventors: Richard Herman Woudenberg, Faysal Kalmoua
  • Patent number: 6380450
    Abstract: Tetrahydroindene is dehydrogenated in a vapor phase in the presence of a metallic catalyst, e.g., a nickel-molybdenum catalyst, to produce indene, which is industrially useful in high yield while inhibiting the catalyst from suffering a decrease in activity. In particular, a higher yield can be attained by a method in which tetrahydroindene is dehydrogenated to first convert it into indane, which is further dehydrogenated to obtain indene.
    Type: Grant
    Filed: April 15, 2000
    Date of Patent: April 30, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventor: Yasuo Matsumura
  • 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
  • Patent number: 6242413
    Abstract: The invention relates to bicyclic aldehydes and ketones of formula (I): wherein n is 1 or 2; R1 and R4 are independently H or CH3; and R2 and R3 are independently H, CH3 or CH2CH3 The invention also provides odorant compositions containing at least one compound of formula (I). A process for the manufacture of R1-methyl substituted compounds of formula (I) having a bridgehead-positioned double bond, as well as intermediates thereof is also provided.
    Type: Grant
    Filed: June 2, 1999
    Date of Patent: June 5, 2001
    Assignee: Givaudan Roure (International) S.A.
    Inventors: Georg Frater, Philip Kraft
  • Patent number: 6162937
    Abstract: A process for preparing bis-cyclopentadienyl compounds bridged by a methylene group is reported, said process comprising reacting formaldehyde with a cyclopentadienyl compound in the presence of a base and of a solvent having a dielectric constant (.epsilon.), measured at 25.degree. C., higher than 7. The bridged compounds, obtainable in high yields with this simple single-step process, can be used to prepare ansa-metallocenes, active as catalyst components in the polymerization of olefins.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: December 19, 2000
    Assignee: Montell Technology Company B.V.
    Inventors: Vu Anh Dang, Lin-Chen Yu, Luigi Resconi
  • Patent number: 5888741
    Abstract: It has been discovered that the degree of hormonal activity of candidate ligands correlates better with degree of fit into DNA than with the strength of receptor binding, and that the receptors in the steroid/thyroid hormone/vitamin A and D family alter the physiochemical properties of DNA and in concert with other transcription factors facilitate insertion of the ligand into DNA. As a result, the magnitude of the response is a function of the structure of the ligand as it related to insertion and fit into the DNA and the specificity of the response is a function of the stereochemistry of the receptor through binding to both the ligand and to the DNA. Based on these discoveries, a method is described herein for identifying drugs having increased activity as compared with the natural ligand for receptors such as the estrogenic receptors.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: March 30, 1999
    Inventor: Lawrence B. Hendry
  • Patent number: 5866706
    Abstract: Utilization of thermodynamic ratios to produce pure rac and pure meso isomers or a mixture thereof.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: February 2, 1999
    Assignee: Boulder Scientific Co.
    Inventor: Daniel Anthony Gately
  • 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: 5763717
    Abstract: A description is given of the preparation of hydroxybiphenyl by dehydrogenation of completely or partially hydrogenated precursors using a supported Rh catalyst which additionally contains chromium, manganese and alkali metal and can contain a sulphur compound. The Rh catalyst which can be used according to the invention is prepared from halide-free starting materials. The Rh catalyst is distinguished by a low dependence of the initial selectivity, with the selectivity in the run-in state and the running-in time on the conditions of the reductive pretreatment and requires only short running-in times to reach the optimum state.
    Type: Grant
    Filed: September 7, 1995
    Date of Patent: June 9, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Christine Mendoza-Frohn, Jurgen Scharschmidt, Ulrich Notheis, Rudolf Jurgen Klee, Gerhard Darsow
  • Patent number: 5723708
    Abstract: A method for producing cyclopentadienes which comprises the step of cyclodehydration of an unsaturated carbonyl compound having a specific chemical structure in a vapor phase in the presence of a specific solid acid catalyst. The cyclopentadienes of the invention can be produced in a high yield from inexpensive starting materials through a simplified reaction process and are useful as intermediate compounds for organic synthesis.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: March 3, 1998
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Matsumura, Kazuharu Suyama, Yoshihisa Inomata
  • 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: 5670683
    Abstract: Cyclopentadineyl compounds of the formula II ##STR1## and formula III ##STR2## their preparation and their use as intermediates in the preparation of metallocene complexes of the formula I.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: September 23, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Langhauser, Jurgen Kerth, Gunther Schweier, Hans-Herbert Brintzinger, Stefan Mansel
  • Patent number: 5608131
    Abstract: A process for the preparation of the compound of the formula ##STR1## comprising dimerizing norbornadiene in the presence of N-methylpiperidine and a combined catalyst of (1,5-cyclooctadiene)(1,3,5-cyclooctatriene)-ruthenium and N,N-dimethylacrylamide.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: March 4, 1997
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Yoshihisa Watanabe, Takeaki Mitsudo, Shi-Wei Zhang
  • 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: 5578741
    Abstract: In accordance with the present invention there is provided a cyclopentadienyl-type ligand represented by the formula ZA, wherein Z is a cyclopentadienyl-type group, wherein A is --YPR.sub.2, --YNR.sub.2, or --NR.sub.2, wherein Y is an alkylene group containing 1 to 24 carbon atoms, wherein each R is individually selected from alkyl groups containing 1 to 20 carbon atoms. Another aspect of the invention is to provide a metallocene represented by the formula ZAMX.sub.3, wherein Z and A are as described above, M is a Group IVB or VB transition metal, and X is a halide. Other aspects of the present invention include catalyst systems comprising the metallocenes and an organoaluminoxane, processes for preparing the above defined ligands, metallocenes and catalyst systems, and polymerization processes employing the catalyst systems.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: November 26, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch