Polycyclic Product Patents (Class 585/360)
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Patent number: 5581004Abstract: 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: GrantFiled: October 17, 1994Date of Patent: December 3, 1996Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5578741Abstract: 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: GrantFiled: May 19, 1995Date of Patent: November 26, 1996Assignee: Phillips Petroleum CompanyInventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
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Patent number: 5498734Abstract: 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: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5449847Abstract: There is provided a process for preparing tercyclohexane by reacting benzene with hydrogen. The process involves the use of a catalyst comprising an acidic solid and a hydrogenation component. The acidic solid may comprise a Group IVB metal oxide, such as zirconia, modified with an oxyanion of a Group VIB metal, such as tungsten. The hydrogenation component may comprise platinum.Type: GrantFiled: April 18, 1994Date of Patent: September 12, 1995Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Scott Han, John D. Lutner, Jose G. Santiesteban
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Patent number: 5446225Abstract: An alkylative cycloaddition method is provided that is particularly useful for the synthesis of many of the Vitamin D analogues with differing side chains. Thus, a preferred synthesis is of Vitamin D analogues having a side chain R.sub.1 where a first precursor having the structure ##STR1## with X being a halide or a pseudo halide, and a second precursor are provided, the second precursor being a 1,7 enyne. These precursors are reacted in the presence of a palladium catalyst to form compounds having the structure ##STR2## where R.sub.2 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group, and R.sub.3 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group.Type: GrantFiled: December 23, 1993Date of Patent: August 29, 1995Assignee: Board of Trustees of the Leland Stanford Junior Univ.Inventors: Barry M. Trost, Jacques Dumas
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Patent number: 5446222Abstract: 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: GrantFiled: June 17, 1994Date of Patent: August 29, 1995Assignee: Mobil Oil CorporationInventors: James R. Boulton, Ross A. Kremer
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Patent number: 5444147Abstract: Hydroxy-substituted-bis-phenyl cyclopropanes of formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are selected from H or OH, at least one of R.sub.1 and R.sub.2 being o, m or p-OH, are useful as monomers to provide cross-linkable polymers useful in fiber reinforced plastics, thermosetting molding compounds, elastomers, advanced composites and other applications; the compounds (I) may be produced by the base catalyzed decomposition of a pyrazoline of formula (II): ##STR2## wherein R.sub.1 and R.sub.2 are as defined hereinbefore.Type: GrantFiled: May 13, 1994Date of Patent: August 22, 1995Inventors: Allan S. Hay, Chunping Gao
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Patent number: 5420320Abstract: In accordance with the present invention there is provided a process for preparing a cyclopentadienyl-type ligand, the process comprises (1) reacting an alkali metal salt of a cyclopentadienyl-type compound and an aminofulvene compound to form a monoanion, (2) reacting the monoanion and a reducing agent to form a dianion, and (3) reacting the dianion and water to produce the cyclopentadienyl-type ligand. Another aspect of the present invention includes a process for preparing a metallocene compound comprising reacting the dianion of step (2) and a transition metal-containing compound to form the metallocene compound. Another aspect of the present invention includes a process for preparing a metallocene compound comprising reacting the ligand of step (3) and an alkali metal compound to form a dianion and then reacting the dianion with a transition metal-containing compound to form the metallocene compound.Type: GrantFiled: June 8, 1994Date of Patent: May 30, 1995Assignee: Phillips Petroleum CompanyInventors: Roland Zenk, Helmut G. Alt, M. Bruce Welch, Syriac J. Palackal
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Patent number: 5414173Abstract: A process of preparing cyclopentadiene or substituted cyclopentadienes, such as tetramethylcyclopentadiene. The process involves contacting under reaction conditions cyclopentenol or a substituted cyclopentenol with a catalyst selected from (1) crystalline and amorphous aluminum phosphates, (2) aluminophosphate molecular sieves, and (3) silicoaluminophosphate molecular sieves. The process produces cyclopentadienes in high isolated yields.Type: GrantFiled: December 22, 1993Date of Patent: May 9, 1995Assignee: The Dow Chemical CompanyInventors: Juan M. Garces, Guo-shuh J. Lee, David R. Wilson
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Patent number: 5406013Abstract: Processes are disclosed for preparing compounds of the formula Z--R--Z where each Z can be selected from cyclopentadienyl type radicals such as substituted or unsubstituted cyclopentadienyl, indenyl, fluorenyl or tetrahydroindenyl or where one Z is Cl, Br, or I by reacting specific Z precursors with a dihaloalkylene compound. Also new cyclopentadienyl-type compounds are disclosed.Type: GrantFiled: January 11, 1993Date of Patent: April 11, 1995Assignee: Phillips Petroleum CompanyInventors: Konstantinos Patsidis, Syriac J. Palackal, Helmut G. Alt
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Patent number: 5393911Abstract: New fluorenyl silane compounds and method for their production are disclosed. The fluorenyl compounds have the formula ##STR1## wherein Z is a substituted or unsubstituted fluorenyl radical and Z' is a substituted or unsubstituted cyclopentadienyl-type radical or a halogen.Type: GrantFiled: November 30, 1992Date of Patent: February 28, 1995Assignee: Phillips Petroleum CompanyInventors: Konstantinos Patsidis, Syriac J. Palackal, Helmut G. Alt
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Patent number: 5338758Abstract: Four bicyclic terpenes isolated from a culture broth of Phoma sp SCF0592, ATCC 74077, pharmaceutical compositions containing them and their use as PAF antagonists to treat allergic and inflammatory diseases are disclosed.Type: GrantFiled: September 30, 1992Date of Patent: August 16, 1994Assignee: Schering CorporationInventors: Min Chu, Mahesh Patel, Ann C. Horan, Vincent P. Gullo
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Patent number: 5324876Abstract: 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: GrantFiled: August 19, 1993Date of Patent: June 28, 1994Assignee: Wayne State UniversityInventor: James H. Rigby
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Patent number: 5310931Abstract: 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: GrantFiled: January 10, 1992Date of Patent: May 10, 1994Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Toshihiro Sagane, Hideaki Yamaguchi, Shuji Minami, Akira Mizuno, Hiroo Wamura
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Patent number: 5292977Abstract: An alkylative cycloaddition method is provided that is particularly useful for the synthesis of many of the Vitamin D analogues with differing side chains. Thus, a preferred synthesis is of Vitamin D analogues having a side chain R.sub.1 where a substantially geometrically pure first precursor having the structure ##STR1## and a second precursor are provided, the second precursor being a 1,7 enyne. These precursors are reacted in the presence of a palladium catalyst to form compounds having the structure ##STR2## where R.sub.2 hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group, and R.sub.3 is hydrogen, hydroxyl, lower alkoxy, fluorine, or a protecting group.Type: GrantFiled: April 20, 1993Date of Patent: March 8, 1994Assignee: Board of Trustees of Leland Stanford Junior UniversityInventors: Barry M. Trost, Jacques Dumas
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Patent number: 5233110Abstract: A process for the preparation of cyclooctene which comprises irradiating 1,5-cyclooctadiene with light in the presence of a photodehydrogenation catalyst, acetone and an alcohol to partially hydrogenate the 1,5-cyclooctadiene.Type: GrantFiled: February 28, 1992Date of Patent: August 3, 1993Assignee: Agency of Industrial Science & TechnologyInventors: Taka-aki Hanaoka, Yoshihiro Sugi, Takehiko Matsuzaki, Kazuhiko Takeuchi, Hironori Arakawa
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Patent number: 5231205Abstract: 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: GrantFiled: September 23, 1991Date of Patent: July 27, 1993Assignee: Board of Regents of the University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5220085Abstract: A method of preparing high density fuels by the addition-rearrangement of pentacyclo[7. 5. 1. O.sup.2,8 . O.sup.3,7 . O.sup.10,14 ]pentadecane. The process comprises the steps of:(a) reacting pentacyclo[7. 5. 1. O.sup.2,8 . O.sup.3,7 . O.sup.10,14 ]pentadecane with an adequate amount of super acid and solvent under inert gas condition to obtain a solution and maintaining at a reaction temperature of 0.degree. C. to 200.degree. C. and a pressure of about 1.0 atmosphere to about 100 atmospheres for a period of from about 10 minutes to about 100 hours to obtain a solution;(b) stirring the solution for a suitable time to complete the addition-rearrangement reaction;(c) separating the reaction mixture in water to obtain an aqueous layer and an organic layer.(d) washing the organic layer with an alkali solution to eliminate any residual acid; and(e) purifying the organic layer by distillation to obtain the desired product.Type: GrantFiled: June 11, 1992Date of Patent: June 15, 1993Assignee: Chung Shan Institute of Science and TechnologyInventors: Sheng-San Cheng, Kou-Fu Liou, Ding-Ping Yen, Chun-Chen Liao
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Patent number: 5191132Abstract: Processes are disclosed for preparing compounds of the formula Z--R--Z where each Z can be selected from cyclopentadienyl type radicals such as substituted or unsubstituted cyclopentadienyl, indenyl, fluorenyl or tetrahydroindenyl or where one Z is Cl, Br, or I by reacting specific Z precursors with a dihaloalkylene compound. Also new cyclopentadienyl-type compounds are disclosed.Type: GrantFiled: May 9, 1991Date of Patent: March 2, 1993Assignee: Phillips Petroleum CompanyInventors: Konstantinos Patsidis, Syriac J. Palackal, Helmut G. Alt
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Patent number: 5157182Abstract: A dehydrocyclization process is described for producing polynuclear organic compounds by contacting a starting organic material having at least one ring moiety comprising at least two adjacent ring carbon atoms each bonded to an independently selected monovalent radical comprising at most about eight carbon atoms provided at least one of the monovalent hydrocarbon radicals comprises more than one carbon atom with a crystalline copper aluminum borate catalyst. The preferred catalyst comprises at least one member selected from the group consisting of (a) crystalline copper aluminum borate and (b) zero valent copper on a support comprising at least one member selected from the group consisting of Al.sub.4 B.sub.2 O.sub.9 and the crystalline copper aluminum borate, the zero valent copper on the support being formed by the reduction of the crystalline copper aluminum borate.Type: GrantFiled: June 19, 1991Date of Patent: October 20, 1992Assignee: Amoco CorporationInventors: Patrick E. McMahon, Larry C. Satek
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Patent number: 5143992Abstract: 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: GrantFiled: July 12, 1991Date of Patent: September 1, 1992Assignee: Shell Oil CompanyInventor: Donald R. Kelsey
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Patent number: 5043503Abstract: Alkylated polycycloparaffinic compounds useful as lubricating stocks are prepared by alkylating a polycycloparaffinic compound with an alkylating agent under alkylation reaction conditions in the presence of a zeolite catalyst. Useful zeolites include zeolite Beta as well as zeolites having a Constraint Index of from about 1 to about 10, such as ZSM-5 and MCM-22. In a preferred embodiment, the polycycloparaffin comprises adamantane and the alkylating agent is a C.sub.14 alpha-olefin.Type: GrantFiled: August 14, 1990Date of Patent: August 27, 1991Assignee: Mobil Oil CorporationInventors: Kenneth J. Del Rossi, Stuart S. Shih
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Patent number: 4967033Abstract: The polyunsaturated compounds of formula ##STR1## having two conjugated double bonds in the endo- and exo- positions of the pentagonal cycle indicated by the dotted lines, and wherein symbols R.sup.1 and R.sup.2, when taken separately, represent respectively a. a linear or brached C.sub.1 to C.sub.4 alkyl radical and b. an hydrogen atom or a methyl radical, or, when taken together with the carbon atoms to which they are bonded form a polymethylenic cycle such as indicated by the dotted line, containing from 5 to 12 carbon atoms, and symbol R.sup.3 stands for an hydrogen atom or a methyl radical, n being an integer equal to 0 or 1, which are useful intermediate products for the preparation of odoriferous macrocyclic ketones, are prepared according to a process comprising a vapor phase cyclization of an enone of formula ##STR2## wherein the dotted line and the symbols n, R.sup.1, R.sup.2 and R.sup.Type: GrantFiled: January 31, 1990Date of Patent: October 30, 1990Assignee: Firmenich S.A.Inventor: Cyril Mahaim
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Patent number: 4943302Abstract: A fuel composition with a high energy content, for direct-ignition internal combustion engines contains a gasoline from petroleum and an amount of up to 90% by volume, as referred to the same fuel composition, of hydrocarbon "cubane" or of its alkyl-derivatives, to be defined by means of the formula: ##STR1## wherein R' and R" represent, independently from each other, a hydrogen atom or an alkyl radical containing from 1 to 3 carbon atoms.Type: GrantFiled: October 11, 1989Date of Patent: July 24, 1990Assignees: Enichem Synthesis S.p.A., AGIP Petroli S.p.A.Inventors: Philip Eaton, Nereo Nodari, Carlo Neri, Luigi Cassar, Fabio Monti, Fausto Alberici
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Patent number: 4918158Abstract: 1,3-Diethynyladamantane and a method of forming same by brominating adamantane to yield 1,3-dibromoadamantane, subjecting vinyl bromide to Friedel-Crafts alkylation with the 1,3-dibromoadamantane to form 1,3-bis(2,2-dibromoethyl)adamantane and subjecting the 1,3-bis(2,2-dibromoethyl)adamantane to dehydrohalogenation to yield the 1,3-diethynyladamantane. 1,3-Diethynyladamantane can be polymerized to produce strong, thermally stable resins suitable for advanced aerospace structural applications, as matrices for carbon-carbon systems and as electrical insulators. It can also be copolymerized with 1-ethynyladamantane to yield similarly useful resins.Type: GrantFiled: July 21, 1986Date of Patent: April 17, 1990Assignee: Fluorochem Inc.Inventors: Kurt Baum, Thomas G. Archibald
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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: 4891460Abstract: The present invention provides a process for producing alkylidenenorbornenes by reacting C.sub.4 -C.sub.6 acyclic conjugated dienes with cyclopentadiene, dicyclopentadiene, or a methyl- or dimethyl-substituted derivative thereof in the presence of a catalyst derivative composed of:(A) a titanium-containing compound, and(B) at least one metallic reducing agent containing the group IA, IIA or IIIA metals in the periodic table.Type: GrantFiled: March 4, 1985Date of Patent: January 2, 1990Assignee: San-Petrochemicals Co., Ltd.Inventor: Yasutaka Ishii
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Patent number: 4873349Abstract: 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: GrantFiled: November 5, 1987Date of Patent: October 10, 1989Assignee: Universite Du Maine (Le Mans)Inventors: Jean-Pierre Robin, Yannick Landais
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Patent number: 4843185Abstract: A process for enhancing the polymerization activity of mixtures of one or more cycloolefin monomers is provided by treatment with heat. This process can be easily incorporated into ring-opening, bulk polymerization methods and methods which form high molecular weight monomers. Enhancing the polymerization activity of crude mixtures of cycloolefin monomers by this process permits polymers having higher glass transition temperatures and higher heat distortion temperatures to be produced with greater economy.Type: GrantFiled: April 8, 1988Date of Patent: June 27, 1989Assignee: The B. F. Goodrich CompanyInventors: James T. Ware, Robert J. Minchak
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Patent number: 4814532Abstract: A process for producing an alkylcyclopentadiene derivative comprising the vapor-phase reaction of a cyclopentadiene derivative and an aliphatic lower alcohol in the presence of a basic crystalline aluminosilicate catalyst containing an alkali metal.Type: GrantFiled: May 22, 1987Date of Patent: March 21, 1989Assignees: Chemical Company, Ltd. Asahi, Zenichi YoshidaInventors: Zenichi Yoshida, Susumu Kato, Yashuhiro Amemiya
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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: 4755317Abstract: The working fluid for traction drive use has a particularly high traction coefficient at high temperatures and the principal ingredient thereof is a decahydronaphthalene compound substituted, on either one or both of the decahydronaphthalene rings, with two or three substituent groups which may be cyclohexyl groups, cyclohexyl alkyl groups, e.g. cyclohexyl methyl, cyclohexyl ethyl, 1-methyl-1-cyclohexyl ethyl and 1-methyl-1-(methylcyclohexyl) ethyl groups, or a combination thereof. The working fluid can be a mixture of a base oil of various types and the above mentioned decahydronaphthalene compound in an amount of 5 to 250 parts by weight per 100 parts by weight of the base oil.Type: GrantFiled: March 18, 1987Date of Patent: July 5, 1988Assignee: Idemitsu Kosan Company LimitedInventors: Tomiyasu Minokami, Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4744885Abstract: Novel class of crystalline microporous ferroaluminophosphate compositions containing as lattice constituents in addition to AlO.sub.2 and PO.sub.2 structural units, ferric and/or ferrous iron in tetrahedral coordination with oxygen atoms. These compositions are prepared hydrothermally using organic templating agents and are suitably employed as catalysts or adsorbents.Type: GrantFiled: August 19, 1985Date of Patent: May 17, 1988Assignee: Union Carbide CorporationInventors: Celeste A. Messina, Brent M. Lok, Edith M. Flanigen
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Patent number: 4691036Abstract: Nickel compounds which can be produced by reacting a nickel(O) compound or a nickel compound, which can be converted in situ into a nickel(O) compound, with an adduct or a mixture of maleic acid anhydride and a tertiary phosphine, optionally with a compound of the formula (I) ##STR1## wherein X represents O, NR.sup.4 or ##STR2## and n represents zero or one,and optionally with an organoaluminium compound, are suitable for the homo-and copolymerization of 1-olefins and for the polymerization of acetylene.Type: GrantFiled: February 18, 1986Date of Patent: September 1, 1987Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz A. O. Starzewski, Josef Witte, Herbert Bartl
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Patent number: 4684754Abstract: The working fluid for traction drive comprises (A) a compound having, in a molecule, two decahydronaphthalene rings bonded either directly to each other or to the same or different carbon atoms in an alkane molecule or a compound having, in a molecule, one decahydronaphthalene ring and one cyclohexane ring bonded either directly to each other or to the same carbon atom in an alkane molecule and (B) a compound having two cyclohexane rings bonded either to the terminal carbon atoms of a C.sub.2-3 alkane molecule or to the carbon atoms of cyclopentane. The working fluid has a high traction coefficient with stability over a wide range of temperature, especially, in low temperatures.Type: GrantFiled: November 14, 1986Date of Patent: August 4, 1987Assignee: Idemitsu Kosan Company LimitedInventors: Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4668835Abstract: The alkylation of para-substituted isopropyl benzenes with dipentenes employing an aluminum halide catalyst system produces novel tetracyclic compounds.Type: GrantFiled: October 4, 1985Date of Patent: May 26, 1987Assignee: Phillips Petroleum Co.Inventor: Raymond L. Cobb
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Patent number: 4609481Abstract: A traction drive fluid composition comprising the principal component of at least one component represented by the general formula (I): ##STR1## wherein R.sup.1 to R.sup.5 are each a hydrogen or an alkyl group containing from 1 to 4 carbon atoms, and 1, m and n are each 1 to 3, said compound (I) comprising a mixture of 70% or less of the cis-form and 30% or more of the trans-form.Type: GrantFiled: May 21, 1985Date of Patent: September 2, 1986Assignee: Idemitsu Kosan Company LimitedInventors: Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4604493Abstract: The invention provides a novel compound 1-cyclohexyl-1,4-dimethyl decahydronaphthalene which is useful as fluids for traction drive. The compound can be synthesized by the hydrogenation of 1,4-dimethyl-4-phenyl-1,2,3,4-tetrahydronaphthalene and analytical results for the identification of the compound are given.Type: GrantFiled: October 8, 1985Date of Patent: August 5, 1986Assignee: Idemitsu Kosan Company LimitedInventors: Nobuaki Shimizu, Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4604492Abstract: The invention provides a novel class of compounds dicyclohexylcyclopentanes or, in particular, 1,3-dicyclohexyl-1-methyl cyclopentane which is synthesized by the hydrogenation of 1-methyl-1,3-diphenyl cyclopentane which in turn is obtained by the dimerization reaction of .alpha.-methylstyrene in the presence of metallic sodium as the catalyst. The compound is useful as a fluid for traction drive.Type: GrantFiled: October 8, 1985Date of Patent: August 5, 1986Assignee: Idemitsu Kosan Company LimitedInventors: Nobuaki Shimizu, Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4570011Abstract: The invention is a process for the preparation of an aromatic hydrocarbon with a cyclobutene ring fused to the aromatic hydrocarbon which comprises, dissolving an ortho alkyl halomethyl aromatic hydrocarbon in an inert solvent and pyrolyzing the solution of ortho alkyl halomethyl aromatic hydrocarbon in the inert solvent under conditions such that the ortho alkyl and halomethyl substituents form a cyclobutene ring thereby forming an aromatic hydrocarbon having a fused cyclobutene ring.Type: GrantFiled: May 21, 1984Date of Patent: February 11, 1986Assignee: The Dow Chemical CompanyInventor: Ying-Hung So
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Patent number: 4556503Abstract: A traction drive fluid is described, containing as the base stock a compound represented by the general formula (I): ##STR1## wherein all the symbols are as defined in the appended claims. This traction drive fluid has a high traction coefficient, has a good thermal stability, is of low viscosity, is of low volatility and further is reduced in temperature dependency of viscosity. Thus it is suitable for use in continuously variable transmission of cars or industrial machines.Type: GrantFiled: September 4, 1984Date of Patent: December 3, 1985Assignee: Idemitsu Kosan Company LimitedInventors: Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4525290Abstract: A process for improving traction coefficient of traction drive fluid at high temperatures by using a compound represented by the general formulae (I), (II) or (III) as a base stock of traction drive fluid, ##STR1## (All the symbols are as defined in the appended claims). This process is helpful for reducing the change of traction coefficients over a wide range of from low temperature to high temperature.Type: GrantFiled: June 29, 1984Date of Patent: June 25, 1985Assignee: Idemitsu Kosan Company LimitedInventors: Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4521324Abstract: A fluid for traction drive is described, containing a liquid material as a base stock wherein the liquid material is prepared by bringing naphthalene or tetralin into contact with a Friedel-Crafts catalyst and then hydrogenating the resulting compounds. This traction drive fluid exhibits a superior traction coefficient from low temperature to elevated temperature and further has a low viscosity. Thus the fluid contributes to the production of small-sized drive mechanisms and can be widely used in various machines.Type: GrantFiled: October 7, 1983Date of Patent: June 4, 1985Assignee: Idemitsu Kosan Company LimitedInventors: Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4436943Abstract: 2,2-Dicyclohexenylpropane is prepared by heating 4,4'-dioxydicyclohexylpropane in the presence of a strong acid, under pressures from 1 to 50 mbar and at 120.degree. to 220.degree. C., distilling off the 2,2-dicyclohexenylpropane produced with the water formed and separating the water out of the top product from the distillation.Type: GrantFiled: March 21, 1983Date of Patent: March 13, 1984Assignee: Bayer AktiengesellschaftInventors: Gebhard Rauleder, Helmut Waldmann
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Patent number: 4431853Abstract: A 1,2-di[trans(equatorial-equatorial)cyclohexyl]-ethane derivative of the following general formula ##STR1## wherein R and R', independently from each other, represent a linear alkyl group having 1 to 10 carbon atoms.Type: GrantFiled: January 6, 1982Date of Patent: February 14, 1984Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Hisato Sato, Haruyoshi Takatsu, Kiyofumi Takeuchi, Yutaka Fujita, Masayuki Tazume, Hiroyuki Ohnishi
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Patent number: 4431855Abstract: In an olefin disproportionation reaction, the formation of undesirable polymer is inhibited by the inclusion of a small amount of carbon monoxide in the feed.Type: GrantFiled: August 30, 1982Date of Patent: February 14, 1984Assignee: Phillips Petroleum CompanyInventors: Robert E. Reusser, Donald G. Kuper
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Patent number: 4398978Abstract: A method for preparation of high density, high energy, low viscosity liquid ydrocarbon fuel by catalytic treatment of tetrahydrodimethyldicyclopentadiene (RJ-4) synthetic fuel. Endo-isomers within the fuel stock are isomerized to exo-isomers by treatment of the fuel stock with catalysts such as aluminum chloride, nickel, or pulverized, acid treated firebrick resulting in a fuel having a lower viscosity than the original RJ-4.Type: GrantFiled: April 26, 1982Date of Patent: August 16, 1983Assignee: The United States of America as represented by the Secretary of the NavyInventors: George W. Burdette, Abraham I. Schneider
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Patent number: 4393258Abstract: A 1-cyclohexyl-2-cyclohexylphenylethane derivative of the following general formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a linear alkyl group having 1 to 7 carbon atoms.Type: GrantFiled: June 10, 1982Date of Patent: July 12, 1983Assignee: Dainippon Mk & Chemicals Inc.Inventors: Hisato Sato, Haruyoshi Takatsu, Yutaka Fujita, Masayuki Tazume, Kiyohumi Takeuchi, Hiroyuki Ohnishi
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Patent number: 4376223Abstract: A method is disclosed for promoting isomerization of sym-octahydrophenanthrene (s-OHP) to sym-octahydroanthracene (s-OHA) in the presence of a catalyst provided by aluminum chloride or aluminum bromide, or a mixture of these two compounds. The rate of isomerization is increased by having the reaction run in the presence of an aryl phenone such as benzophenone.Type: GrantFiled: April 26, 1982Date of Patent: March 8, 1983Assignee: Koppers Company, Inc.Inventor: William T. Gormley
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Patent number: 4376224Abstract: A method is disclosed for promoting isomerization of sym-octahydrophenanthrene (s-OHP) to sym-octahydroanthracene (s-OHA) in the presence of a catalyst provided by aluminum chloride or aluminum bromide, or a mixture of these two compounds. The rate of isomerization is increased by having the reaction run in the presence of an acyl peroxide such as benzoyl peroxide or lauroyl peroxide.Type: GrantFiled: April 26, 1982Date of Patent: March 8, 1983Assignee: Koppers Company, Inc.Inventor: William T. Gormley