Dimerizing A Cycloolefin Patents (Class 585/362)
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Patent number: 11932724Abstract: A novel family of cycloalkanes compounds having one or more allylidene functionalities which can be used to create cross-linked thermosets and thermoplastics having thermal stability. An example heptacyclo [6.6.0.02,6.03,13.04,11.05,9.010,14] tetradecane (HCTD) complex with terminal allylidene groups at the 7- and 12-positions (HCTD-7,12-diallylidene) was generated from norbornadiene via an efficient six-step synthesis. Thermal polymerization at temperatures ranging from 160 to 240° C. yielded a robust cross-linked material with thermal stability up to 485° C. in air, a glass transition temperature of 377° C., and a char yield (600° C.) of 56% in air. Applications include heat resistant composites utilized in the aerospace, electronic, automotive and textile industries.Type: GrantFiled: April 1, 2021Date of Patent: March 19, 2024Assignee: The United States of America, as represented by the Secretary of the NavyInventors: Benjamin G. Harvey, Kyle E. Rosenkoetter
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Patent number: 11370728Abstract: A hydrocarbon production method for producing hydrocarbons from a hydrocarbon mixture includes: a first extractive distillation step of performing extractive distillation of an extractive distillation target to obtain a fraction (A) in which isoprene and piperylene are enriched and a fraction (B) in which a linear hydrocarbon and a branched hydrocarbon are enriched; a first distillation step of obtaining a fraction (C) in which isoprene is enriched and a fraction (D) in which piperylene is enriched from the fraction (A); a dehydrogenation step of performing dehydrogenation or oxidative dehydrogenation of either or both of the linear hydrocarbon and the branched hydrocarbon contained in the fraction (B) to obtain a dehydrogenated product; and a recovery step of supplying the dehydrogenated product to an extractive distillation column or a distillation column and obtaining isoprene and/or piperylene from the dehydrogenated product.Type: GrantFiled: February 21, 2018Date of Patent: June 28, 2022Assignee: ZEON CORPORATIONInventor: Hideaki Miki
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Patent number: 10561962Abstract: A dynamic process for purifying dicyclopentadiene from a mixed liquid hydrocarbon stream comprising dicyclopentadiene and one or more of a C5 paraffin, a C5 olefin, co-dimers, cyclopentadiene, benzene, vinyl norbornene, bicyclononadiene, propenyl norbornene, isopropenyl norbornene, methylbicyclononadiene, methyldicyclopentadiene, and various minor organic impurities is introduced, wherein the dicyclopentadiene is separated from the mixed liquid hydrocarbon stream by melt crystallizing sweating and collecting dicyclopentadiene.Type: GrantFiled: December 29, 2016Date of Patent: February 18, 2020Assignee: SABIC GLOBAL TECHNOLOGIES B.V.Inventors: P. S. Sreenivasan, Omkar D. Gadgil, P. S. Mahabala
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Patent number: 10252240Abstract: Producing C5 olefins from steam cracker C5 feeds may include reacting a mixed hydrocarbon stream comprising cyclopentadiene, C5 olefins, and C6+ hydrocarbons in a dimerization reactor where cyclopentadiene is dimerized to dicyclopentadiene. The dimerization reactor effluent may be separated into a fraction comprising the C6+ hydrocarbons and dicyclopentadiene and a second fraction comprising C5 olefins and C5 dienes. The second fraction, a saturated hydrocarbon diluent stream, and hydrogen may be fed to a catalytic distillation reactor system for concurrently separating linear C5 olefins from saturated hydrocarbon diluent, cyclic C5 olefins, and C5 dienes contained in the second fraction and selectively hydrogenating C5 dienes. An overhead distillate including the linear C5 olefins and a bottoms product including cyclic C5 olefins are recovered from the catalytic distillation reactor system.Type: GrantFiled: February 21, 2018Date of Patent: April 9, 2019Assignee: Lummus Technology Inc.Inventors: Yongqiang Xu, Peter Loezos, Willibrord A. Groten, Romain Lemoine
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Patent number: 9783469Abstract: A first method for refining dicyclopentadiene of the present invention is characterized in that the method separates and recovers dicyclopentadiene by distilling the crude dicyclopentadiene that contains dicyclopentadiene and is obtained by removing a C5 fraction and a BTX fraction from the reaction product obtained by dimerization reaction of the cracked gasoline by-produced in an ethylene plant that uses as feed stock a C2 fraction, a C3 fraction and a C4 fraction. A second method for refining dicyclopentadiene of the present invention is characterized in that the dicyclopentadiene-containing fraction refined by distillation is brought into contact with an inert gas or a hydrocarbon gas having 1 to 3 carbon atoms.Type: GrantFiled: December 8, 2015Date of Patent: October 10, 2017Assignees: JX NIPPON OIL & ENERGY CORPORATION, JX NIPPON CHEMICAL TEXAS INC.Inventors: Takaaki Takeshita, Takeshi Omata, Takashi Suzuki, Takashi Morikita, Satoshi Mori
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Publication number: 20150133691Abstract: In a reaction in which a boron trifluoride complex is used as a catalyst, the expensive and harmful boron trifluoride complex is separated from a reaction mixture containing the boron trifluoride complex by separating the boron trifluoride complex present in the reaction mixture by using a saturated hydrocarbon-based solvent.Type: ApplicationFiled: March 1, 2013Publication date: May 14, 2015Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Sumihiro Oda, Masashi Machida, Hiroki Sekiguchi, Yukio Yoshida, Toshiyuki Tsubouchi
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Patent number: 8975463Abstract: A process for making high density fuels from mixed terpene feedstocks and the resulting high density fuel products.Type: GrantFiled: September 6, 2012Date of Patent: March 10, 2015Assignee: The United States of America as Represented by the Secretary of the NavyInventors: Benjamin G. Harvey, Heather A. Meylemans, Roxanne L. Quintana
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Patent number: 8969641Abstract: 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: GrantFiled: September 3, 1976Date of Patent: March 3, 2015Inventors: Richard E. Ware, Edward J. Janoski, Abraham Schneider
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Publication number: 20140213746Abstract: The present invention relates to pre-catalysts for olefin metathesis and composition involving these pre-catalysts.Type: ApplicationFiled: September 3, 2012Publication date: July 31, 2014Applicant: Technische Universität GrazInventors: Christian Slugovc, Julia Wappel
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Patent number: 8704022Abstract: Embodiments of the present invention are directed generally to methods for producing high purity exo-alkenylnorbornenes from a mixture of conformational isomers thereof.Type: GrantFiled: August 6, 2008Date of Patent: April 22, 2014Assignee: Promerus, LLCInventors: Andrew Bell, Dane Jablonski, Elaine Koronich, Brian Knapp, Dino Amoroso
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Patent number: 8227651Abstract: 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: GrantFiled: August 31, 2009Date of Patent: July 24, 2012Assignee: The United States of America as represented by the Secretary of the NavyInventors: Benjamin G. Harvey, Michael E. Wright, Roxanne L. Quintana
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Patent number: 8003836Abstract: A process has been developed for producing diesel boiling range fuel from renewable feedstocks such as plant oils, animal fats and oils, and greases. The process involves treating a renewable feedstock by hydrogenating and deoxygenating to provide a diesel boiling range fuel hydrocarbon product. If desired, the hydrocarbon product can be isomerized to improve cold flow properties. A portion of the hydrocarbon product is recycled to the treatment zone to increase the hydrogen solubility of the reaction mixture.Type: GrantFiled: October 6, 2010Date of Patent: August 23, 2011Assignee: UOP LLCInventors: Terry L. Marker, Peter Kokayeff, Suheil F. Abdo, Tom N. Kalnes
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Patent number: 7999143Abstract: A process has been developed for producing diesel boiling range fuel from renewable feedstocks such as plant and animal fats and oils. The process involves treating a renewable feedstock by hydrogenating and deoxygenating to provide a hydrocarbon fraction useful as a diesel boiling range fuel. Water is added to the deoxygenation reaction to drive carbon monoxide and water to react to form hydrogen and carbon dioxide. The hydrogen is then consumed by the reactions. If desired, the hydrocarbon fraction can be isomerized to improve cold flow properties.Type: GrantFiled: August 18, 2008Date of Patent: August 16, 2011Assignees: UOP LLC, ENI S.p.A.Inventors: Terry L. Marker, Peter Kokayeff, Giovanni Faraci, Franco Baldiraghi
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Patent number: 7915467Abstract: Disclosed is a semiconductor wafer which is characterized in that a resin layer composed of a resin composition containing a cyclic olefin resin (A) having an epoxy group and a photoacid generator (B) is arranged on a surface on which a circuit element is formed, and the residual stress of the resin layer after curing is 1-20 MPa. Also disclosed is a semiconductor device comprising such a semiconductor wafer.Type: GrantFiled: October 20, 2005Date of Patent: March 29, 2011Assignee: Sumitomo Bakelite Company, Ltd.Inventors: Junya Kusunoki, Takashi Hirano
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Patent number: 6790342Abstract: Processes are provided to produce a dilute ethylene stream and a dilute propylene stream from a cracked gas stream. One process comprises separating the cracked gas stream to produce a C3− stream and a C3+ stream; hydrogenating the C2− stream in a hydrogenation zone to remove a portion of the acetylene to produce the dilute ethylene stream and routing the C3+ stream to storage or other process unit. Another process comprises separating a cracked gas stream in a depropanizer zone to form a C3− stream and a C4+ stream; separating the C3− stream in a deethanizer zone to form a C2− and a C3 stream; hydrogenating a portion of the acetylene in the C2− stream in a hydrogenation zone to produce a dilute ethylene stream; and routing the C3 stream to storage or other process unit.Type: GrantFiled: February 27, 2002Date of Patent: September 14, 2004Assignee: Chevron Phillips Chemical Company LPInventors: Rodney L. Porter, Anne M. Balinsky, Eric P. Weber
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Patent number: 6783659Abstract: A process is provided to produce a dilute ethylene stream and a dilute propylene stream to be used as feedstocks for producing olefin-based derivatives. Specifically, the dilute ethylene stream is used as a feedstock to produce ethylbenzene, and the dilute propylene stream is used as a feedstock to produce cumene, acrylic acid, propylene oxide and other propylene based derivatives.Type: GrantFiled: November 16, 2001Date of Patent: August 31, 2004Assignee: Chevron Phillips Chemical Company, L.P.Inventors: Rodney L. Porter, Anne M. Balinsky, Eric P. Weber
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Publication number: 20030100809Abstract: The present invention relates to a process for separating the isoprene, 1,3-pentadiene and dicyclopentadiene from a C5 cuts, comprising dimerization of the cyclopentadiene and selective catalytic hydrogenation. The second extractive rectification step can be omitted, because the alkynes are removed through selective catalytic hydrogenation prior to the extractive rectification. As a result, the solvent-recovering units can be simplified, and thus the process as a whole can be optimized. Correspondingly, the investment and energy consumption, the operation cost, and finally the production cost can be substantially reduced.Type: ApplicationFiled: September 27, 2002Publication date: May 29, 2003Inventors: Baoliang Tian, Puyang Li, Chunpeng Du, Hongfen Xu, Haiqiang Feng, Jingmin Hu, Jidong Gao, Ming Ma
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Patent number: 6512152Abstract: 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: GrantFiled: February 28, 2000Date of Patent: January 28, 2003Assignee: Nippon Petrochemicals Company, LimitedInventors: Masaki Hashizume, Tomonobu Uchida, Fuyuki Aida, Takashi Suzuki, Yoshihisa Inomata, Yasuo Matsumura
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Patent number: 6441259Abstract: 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: GrantFiled: July 5, 2001Date of Patent: August 27, 2002Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Fuyuki Aida, Takashi Suzuki, Yasuo Matsumura
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Patent number: 6258989Abstract: A hydrocarbon feedstock containing C5 olefins, C5 diolefins, CPD, DCPD, and aromatics is processed by the steps of heating a hydrocarbon feedstock containing CPD, DCPD, C5 diolefins, benzene, toluene, and xylene in a heating zone, to dimerize CPD to DCPD, thereby forming a first effluent; separating the first effluent into a C6+ stream and a C5 diolefin stream; separating the C6+ stream into a C6-C9 stream and a C10+ stream; separating the C10+ stream into a fuel oil stream and a DCPD stream; and hydrotreating the C6-C9 stream to thereby form a BTX stream.Type: GrantFiled: September 30, 1999Date of Patent: July 10, 2001Assignee: Phillips Petroleum CompanyInventors: Steven A. Owen, Marvin M. Johnson, Tin-Tack Peter Cheung, Mark E. Lashier
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Patent number: 6093865Abstract: The present invention relates to a method for using a single distillation column to recover the reactants and products from the reaction of a cyclic diolefin and an olefin to produce an alkenyl bridged ring compound.Type: GrantFiled: June 16, 1998Date of Patent: July 25, 2000Assignee: Exxon Chemical Patent Inc.Inventors: James R. Lattner, Leonel E. Sanchez, Christopher L. Becker, Bruce C. Devoy
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Patent number: 5847247Abstract: 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: GrantFiled: March 18, 1996Date of Patent: December 8, 1998Assignee: Arizona Chemical CompanyInventors: Alexander J. Conte, Bobby G. Johnson, Raymond H. Jones, Claude F. Phillips, Jr.
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Patent number: 5723709Abstract: 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: GrantFiled: July 9, 1996Date of Patent: March 3, 1998Assignee: Arizona Chemical CompanyInventors: Claude Frank Phillips, Jr., James William Booth
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Patent number: 5608131Abstract: 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: GrantFiled: January 20, 1995Date of Patent: March 4, 1997Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Yoshihisa Watanabe, Takeaki Mitsudo, Shi-Wei Zhang
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Patent number: 5569804Abstract: The present invention relates to a method for using a single distillation column to recover the reactants and products from the reaction of a cyclic diolefin and an olefin to produce an alkenyl bridged ring compound.Type: GrantFiled: December 30, 1993Date of Patent: October 29, 1996Assignee: Exxon Chemical Patents Inc (ECPI)Inventors: James R. Lattner, Leonel E. Sanchez
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Patent number: 5461181Abstract: A process for the heterogeneous catalytic oligomerization of norbornene comprising the steps of reacting norborene 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 conditions to evolve a product containing norbornene oligomers.Type: GrantFiled: May 5, 1994Date of Patent: October 24, 1995Assignee: Mobil Oil CorporationInventors: Costandi A. Audeh, James R. Boulton, Ross A. Kremer, Yusheng Xiong
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Patent number: 5422027Abstract: A process for improving the traction coefficient between at least two relatively rotatable elements having tractive surfaces in a torque transmitting relationship which comprises introducing between the tractive surfaces of the elements a traction drive fluid comprising, as the active component, a hydrocarbon compound having a bicylo octane skeleton.Type: GrantFiled: November 1, 1993Date of Patent: June 6, 1995Assignee: Idemitsu Kosan Co., Ltd.Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 5321177Abstract: Recently, as a process for manufacturing cyclopentadiene resin-shaped articles, an attention has been given to reaction injection molding (RIM). To conduct RIM, it is necessary to use high purity dicyclopentadiene (DCPD) as the raw material. Vapor-phase thermal cracking of DCPD is usually used as a step of process for manufacturing high purity DCPD. Hithertofore, when conducting thermal cracking of DCPD, coke formation within cracking tubes is the most serious and troublesome problem. A vapor-phase thermal cracking process for resolving the problem by a very simple procedure is described herein. Further, a process for manufacturing high purity DCPD suitable as a raw material for use in RIM utilizing the vapor-phase thermal cracking process just mentioned above is also described.Type: GrantFiled: April 16, 1992Date of Patent: June 14, 1994Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Takao Nakamura, Masaru Kawakita, Katsumi Minomiya
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Patent number: 5283384Abstract: A traction drive fluid composition comprising a hydrocarbon having a bicyclo octane skeleton, such as a bicyclo(3,2,1) octane skeleton, a bicyclo(2,2,2)octane skeleton or a bicyclo(3,3,0)octane skeleton. The traction drive fluid has a low viscosity and has a high traction coefficient over a wide temperature range.Type: GrantFiled: March 2, 1992Date of Patent: February 1, 1994Assignee: Idemitsu Kosan Co., Ltd.Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4922047Abstract: Bicyclic and monocyclic terpenes are oligomerized by contact over a zeolite catalyst to produce high boiling lube oil traction fluid having a high traction coefficient. The traction fluid comprises dimers, trimers and tetramers of the bicyclic and monocyclic terpenes. The lube oil is catalytically hydrogenated to obtain a saturated cycloparaffin hydrocarbon oil traction fluid.Type: GrantFiled: December 22, 1988Date of Patent: May 1, 1990Assignee: Mobil Oil CorporationInventors: Catherine S. H. Chen, Thomas R. Forbus, Jr.
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Patent number: 4906797Abstract: Liquid dicyclopentadiene feedstocks are provided for bulk polymerization by the addition of reactive norbornene function containing cycloolefin monomers to solid, high purity dicyclopentadiene compositions. These liquid dicyclopentadiene feedstocks provide a high degree of conversion to polymer under bulk polymerization conditions.Type: GrantFiled: September 12, 1988Date of Patent: March 6, 1990Assignee: The B.F. Goodrich CompanyInventors: Parley C. Lane, Jr., George M. Benedikt, Linwood P. Tenney, Paul T. Stricharczuk
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Patent number: 4899005Abstract: A process for increasing the molecular weight of cycloolefin monomers is provided by this invention which can be incorporated into ring-opening polymerization methods. This method is particularly suited for bulk polymerization processes but can also be used for solution polymerization processes. By increasing the molecular weight of the cycloolefin monomers, polymers having higher glass transition temperatures are obtained.Type: GrantFiled: November 19, 1987Date of Patent: February 6, 1990Assignee: The B. F. Goodrich CompanyInventors: Parley C. Lane, Linwood P. Tenney, George M. Benedikt, Paul T. Stricharczuk
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Patent number: 4804795Abstract: 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: GrantFiled: February 2, 1988Date of Patent: February 14, 1989Assignee: Nippon Oil Co., Ltd.Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Hirosuke Imai
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Patent number: 4751337Abstract: A method of preparing a mixture composed principally of dicyclopentadiene which is caused to remain liquid at low temperatures by the presence of other cyclopentadiene oligomers.Type: GrantFiled: December 8, 1986Date of Patent: June 14, 1988Assignee: Hercules IncorporatedInventors: Herbert H. Espy, Albert S. Matlack
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Patent number: 4668836Abstract: A process for producing cycloalkadienes in liquid phase by metathesis reaction of cycloalkenes in the presence of a carrier catalyst based on Re.sub.2 O.sub.7 /Al.sub.2 O.sub.3. The cycloalkenes in the form of 0.01 to 0.05 molar solutions are contacted with the carrier catalyst in a fixed bed arrangement with contact times of 10 to 100 seconds.Type: GrantFiled: October 24, 1985Date of Patent: May 26, 1987Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Hans-J/u/ rgen Eberle, Franz-Heinrich Kreuzer, Norbert Zeitler
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Patent number: 4604490Abstract: The present invention is connected with a high-density liquid fuel for rockets and jet engines which mainly comprises a compound represented by the general formula ##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 a sum of R.sup.1 to R.sup.3 is an integer of 1 to 3.Type: GrantFiled: June 19, 1985Date of Patent: August 5, 1986Assignee: Nippon Oil Company Ltd.Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Hirosuke Imai
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Patent number: 4427467Abstract: An improved ramjet fuel consisting of hydrogenated hydrocarbons uses a mium weight percentage of 50% tetrahydromethylcyclopentadiene dimer (TH-dimer) with about 50% by wt. exo-tetrahydrodicyclopentadiene (Exo-THDC). The mixture exceeds U.S. Navy flash point requirements of 60.degree. C. while yielding a lower viscosity than TH-dimer alone. Volumetric heating properties of the mixture make it an excellent ramjet fuel.Type: GrantFiled: April 29, 1982Date of Patent: January 24, 1984Assignee: The United States of America as represented by the Secretary of the NavyInventors: George W. Burdette, Lewis Hall
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Patent number: 4355194Abstract: A method for catalytically isomerizing a mixture of hexacyclic dimers obtained by dimerizing norbornadiene in the presence of a zero valent iron complex whereby the hydrogenated derivatives of the resultant isomerization product exhibits substantially lower freeze point than that associated with the hydrogenated derivatives of said precursor dimer mixture, the latter representing the highest energy liquid hydrocarbon fuel commercially available.Type: GrantFiled: November 6, 1980Date of Patent: October 19, 1982Assignee: Ashland Oil, Inc.Inventors: Richard V. Norton, Dennis H. Fisher, Garry M. Graham, Peter J. Frank
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Patent number: 4320238Abstract: A high density fuel composition having low temperature operational capability for propelling turbo-jet, limited volume missile systems consisting essentially of at least 95 weight percent exo-tetrahydrodicyclopentadiene (JP-10) and a correspondingly minor amount of a C.sub.3 -C.sub.7 saturated hydrocarbon.Type: GrantFiled: August 21, 1980Date of Patent: March 16, 1982Assignee: Ashland Oil, Inc.Inventors: Richard V. Norton, Steven C. Howe
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Patent number: 4320239Abstract: A product mixture of a norbornene and a tetracyclododecene is prepared in any desired mole ratio in the range of 95/5 to 5/95 which comprises heating an olefin, cyclopentadiene, and a norbornene in the respective mole ratio of 1-20/1-5/1-5, at a temperature of 100.degree. to 400.degree. C., 100 to 5000 psi, and 0.1 to 5 hours of residence time.Type: GrantFiled: February 13, 1981Date of Patent: March 16, 1982Assignee: The B. F. Goodrich CompanyInventor: Wolfgang Schneider
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Patent number: 4300008Abstract: Methods employing a catalyst system comprising a hydrogen fluoride solution of tantalum pentafluoride and/or niobium pentafluoride for the preparation of 2,6-dimethyldecalin from a 12 carbon atom-containing dicyclic naphthenic isomer thereof and for the preparation of a mixture of 2,6-dimethyldecalin and a 12 carbon atom-containing dicyclic naphthenic isomer thereof from methylcyclopentane and/or cyclohexane are disclosed.Type: GrantFiled: September 25, 1980Date of Patent: November 10, 1981Assignee: Standard Oil Company (Indiana)Inventor: David A. McCaulay
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Patent number: 4286109Abstract: A high density specialty fuel for propelling limited volume ramjet and turbojet missile systems comprising a blend of at least 70 weight percent of exotetrahydrodicyclopentadiene and a correspondingly minor amount of a combination of a C.sub.5 -C.sub.7 alkane or cycloalkane and a tetrahydro derivative of the trimer and/or co-trimer of cyclopentadiene and methylcyclopentadiene.Type: GrantFiled: July 31, 1980Date of Patent: August 25, 1981Assignee: Ashland Oil, Inc.Inventors: Richard V. Norton, Dennis H. Fisher
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Patent number: 4277636Abstract: Method for effecting the formation of co-trimers of cyclopentadiene and methylcyclopentadiene whereby a mixture of the dimers of said dienes is heated in the presence of an inert solvent. The foregoing method is implemented to provide a high energy fuel by substantially completely hydrogenating the resultant trimerization product.Type: GrantFiled: August 11, 1980Date of Patent: July 7, 1981Assignee: Ashland Oil, Inc.Inventors: Richard V. Norton, Peter J. Frank, Dennis H. Fisher, Steven C. Howe
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Patent number: 4255600Abstract: A process for the selective dimerization of cycloolefins having from 5 to about 12 carbon atoms is provided. The process comprises contacting of the olefin in the liquid phase with ZSM-12 at temperatures of 75.degree. to 400.degree. C.Type: GrantFiled: December 5, 1979Date of Patent: March 10, 1981Assignee: Mobil Oil CorporationInventor: L. Brewster Young
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Patent number: 4246373Abstract: Aluminum cyclopentadienyl compounds can be used to synthesize a variety of organic molecules containing the cyclopentadiene group, e.g., substituted cyclopentadiene compounds, polymer molecules with cyclopentadiene pendant groups, and polymer molecules with cyclopentadiene terminal groups.Type: GrantFiled: February 14, 1980Date of Patent: January 20, 1981Inventors: Joseph P. Kennedy, Kenneth F. Castner
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Patent number: 4225736Abstract: Novel codimer (I) of norbornadiene and 1,3-cyclohexadiene and its hydrogenated derivative (II), having the following structures: ##STR1## and processes for preparing both are disclosed. Product (II) can be used as a high energy fuel. Process for codimer I involves use of three component homogeneous catalytic system of cobaltic or cobaltous acetylacetonate, 1,2-bisdiphenylphosphino ethane and one of three alkyl aluminum chlorides.Type: GrantFiled: April 17, 1979Date of Patent: September 30, 1980Assignee: Sun Oil Company of PennsylvaniaInventor: Harry K. Myers, Jr.
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Patent number: 4225735Abstract: Isomerization of a liquid, saturated endo-endo norbornadiene hexacyclic dimer involves the use of a catalytic amount of acidic alumina or a montmorillonite. The resulting isomeric product is solid, at ambient temperature, and can be used as a missile fuel.Type: GrantFiled: January 29, 1979Date of Patent: September 30, 1980Assignee: Suntech, Inc.Inventors: Lewis W. Hall, Jr., John D. Tice, Harry K. Myers, Jr., Abraham Schneider
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Patent number: 4218570Abstract: Liquid organic reaction products prepared in the presence of homogeneous iron catalyst values are contacted with a strong Lewis acid to effect removal of said values as inorganic precipitates.Type: GrantFiled: February 21, 1979Date of Patent: August 19, 1980Assignee: Ashland Oil, Inc.Inventor: Richard V. Norton
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Patent number: 4208355Abstract: Binor-S is prepared by the catalytic dimerization of norbornadiene (bicyclo[2.2.1]hepta-2,5-diene) using a homogeneous catalyst system of cobaltic acetylacetonate and diethylaluminum chloride and triphenyl phosphine. Ethylaluminum dichloride or aluminum ethylsesquichloride can be used in lieu of the diethylaluminum chloride. The reaction rate is rapid at an ambient temperature. Binor-S can be used as a precursor for hydrocarbons having utility as a high energy fuel.Type: GrantFiled: August 13, 1976Date of Patent: June 17, 1980Assignee: Suntech, Inc.Inventors: Harry K. Myers, Jr., Abraham Schneider
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Patent number: 4207080Abstract: Norbornadiene [bicyclo(2.2.1)heptadiene-2,5] is dimerized to the exo-exo stereoisomer of the hexacyclic dimer of norbornadiene at both an excellent selectivity and conversion using an effective amount of a three component catalytic system of diethylaluminum chloride, ferric or ferrous or cobaltic or cobaltous acetylacetonate and bis(1,2-diphenylphosphino)ethane. The reaction rate is rapid. After hydrogenation the exo-exo hexacyclic dimer can be used as a component of high energy fuel for either jet or rocket propulsion.Type: GrantFiled: December 11, 1975Date of Patent: June 10, 1980Assignee: Suntech, Inc.Inventors: George Suld, Abraham Schneider, Harry K. Myers, Jr.