Alicyclic Compound Synthesis Patents (Class 585/350)
  • Patent number: 5597455
    Abstract: 3-Carene and limonene cannot be separated from each other by rectification because of the closeness of their boiling points. They are readily separated by extractive distillation. Effective agents are: diethylene glycol phenyl ether, nonyl phenol, tripropylene glycol methyl ether, ethyl salicylate, 4-ethylphenol and 2-phenoxyethanol.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: January 28, 1997
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5585509
    Abstract: Metallocene complexes of the general formula I ##STR1## where the substituents Y, M, x, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are as described in the disclosure, and ligand systems of the general formula II ##STR2## as intermediates.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: December 17, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Langhauser, David Fischer, J urgen Kerth, G unther Schweier, Hans-Herbert Brintzinger, Elke Barsties, Werner Roell
  • Patent number: 5582693
    Abstract: 3-Carene and limonene cannot be separated from each other by rectification because of the closeness of their boiling points. They are readily separated by azeotropic distillation. Effective agents are: cyclopentanol, 2-nitropropane, ethyl formate amyl acetate dimethyl carbonate, tetrahydrofuran, acetic acid and 2-amino-amethyl-1-propanol.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: December 10, 1996
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5545785
    Abstract: The invention relates to a process for preparing biscyclopentadienyl compounds of the general formula(CpR.sub.a).sub.2 --Qby reaction of CpR.sub.a, in a first step, in accordance with the general equation2CpR.sub.a +(R.sup.3 R.sup.4).sub.c Mg.fwdarw.(CpR.sub.a).sub.2 Mg+cR.sup.3 H+cR.sup.4 Hand further reaction in accordance with the general equation(CpR.sub.a).sub.2 Mg+XQX.sup.1 .fwdarw.(CpR.sub.a).sub.2 Q+MgXX.sup.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: August 13, 1996
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5498734
    Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5449847
    Abstract: 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: Grant
    Filed: April 18, 1994
    Date of Patent: September 12, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Scott Han, John D. Lutner, Jose G. Santiesteban
  • Patent number: 5446222
    Abstract: The invention provides a two-step process for converting cyclopentadiene dimer to a high density fuel mixture comprising the steps of:(a) reacting said cyclopentadiene dimer in the presence of a solid catalyst comprising a porous crystalline material having a Constraint Index of from about 0.1 to about 12 under oligomerization/isomerization conditions to convert at least a portion of said cyclopentadiene dimer to a normally liquid intermediate product containing cyclopentadiene trimer, cyclopentadiene tetramer, and the isomerized and oligomerized products derived from the reaction of at least three cyclopentadiene monomer units;(b) hydrogenating said normally liquid intermediate product of step (a) in the presence of a hydrogenation catalyst to form a normally liquid high energy density fuel.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: August 29, 1995
    Assignee: Mobil Oil Corporation
    Inventors: James R. Boulton, Ross A. Kremer
  • Patent number: 5444147
    Abstract: 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: Grant
    Filed: May 13, 1994
    Date of Patent: August 22, 1995
    Inventors: Allan S. Hay, Chunping Gao
  • Patent number: 5422027
    Abstract: 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: Grant
    Filed: November 1, 1993
    Date of Patent: June 6, 1995
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 5414173
    Abstract: 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: Grant
    Filed: December 22, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Juan M. Garces, Guo-shuh J. Lee, David R. Wilson
  • Patent number: 5391264
    Abstract: alpha-Phellandrene is difficult to separate from d-limonene by conventional distillation or rectification because of the proximity of their boiling points. alpha-Phellandrene can be readily separated from d-limonene by azeotropic distillation. Effective agents are n-butyl acetate and sulfolane.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: February 21, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5380405
    Abstract: alpha-Phellandrene is difficult to separate from 3-carene by conventional distillation or rectification because of the proximity of their boiling points. alpha-phellandrene can be readily separated from 3-carene by azeotropic distillation. Effective agents are methyl formate, nitroethane and acetal.
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: January 10, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5349100
    Abstract: There are provided enantiomerically enhanced chiral substituted cyclopentadienyl ligands, and compounds thereof, and a process for their making comprising contacting an optionally substituted fulvene having a prochiral carbon 6 with a lithium salt of an amine, amino acid or amide to effectuate enantioselective hydride addition to the carbon 6 of the fulvene so as to create a chiral center. There are further provided enantiomerically enhanced chiral organometallic complexes having one or more chiral substituted cyclopentadienyl groups.
    Type: Grant
    Filed: January 2, 1991
    Date of Patent: September 20, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Eric A. Mintz
  • Patent number: 5283384
    Abstract: 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: Grant
    Filed: March 2, 1992
    Date of Patent: February 1, 1994
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 5208357
    Abstract: There are provided enantiomerically enhanced chiral substituted cyclopentadienyl ligands and compounds thereof, and a process for their making comprising contacting a substituted fulvene or derivative thereof with an enantiomerically enhanced or pure nucleophile having at least one chiral center. There are further provided enantiomerically enhanced chiral organometallic complexes having one or more chiral substituted cyclopentadienyl groups.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: May 4, 1993
    Assignee: Exxon Chemical Patents, Inc.
    Inventor: Eric A. Mintz
  • Patent number: 4879425
    Abstract: A composition comprises a physical mixture of (i) and oxide of molybdenum and/or tungsten supported by a silica-containing material and (ii) a pillared interlayered clay. This composition is used as catalyst in the conversion of C.sub.2 -C.sub.4 monoolefins to C.sub.5 -C.sub.12 hydrocarbons.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: November 7, 1989
    Assignee: Phillips Petroleum Company
    Inventors: Simon G. Kukes, Robert L. Banks, Jesse R. Harris
  • Patent number: 4877908
    Abstract: Chiral phosphorus-containing ligands comprising at least one amine radical and at least one dihydrocarbylphosphinoxy radical of the formula W=OP (R).sub.2, in which R is a hydrocarbon radical selected from the group consisting of alkyl, aryl, and cycloalkyl radicals, wherein the ligand is selected from the group consisting of:those of the formula ##STR1## those of the formula ##STR2## those of the formula ##STR3## those of the formula ##STR4## in which formulae: R.sub.1 and R.sub.2 are selected from the group consisting of a hydrogen atom and hydrocarbon radicals;R.sub.3 and R.sub.4, which must be different from one another, are selected from the group consisting of a hydrogen atom and hydrocarbon radicals that may or may not carry at least one functional group selected from the group consisting of the alcohol, thiol, thioether, amine, imine, acid, ester, amide, and ether functional groups; andR.sub.5 and R.sub.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: October 31, 1989
    Assignee: Norsolor
    Inventors: Michele Petit, Andre Mortreux, Francis Petit, Gerard Buono
  • Patent number: 4804794
    Abstract: The present invention relats to novel copolymers of alpha-olefins comprised of intramolecularly heterogeneous and intermolecularly homogeneous copolymer chains.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: February 14, 1989
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Gary Ver Strate, Ricardo Bloch, Mark J. Struglinski, John E. Johnston, Roger K. West
  • Patent number: 4709061
    Abstract: Mixtures of new dimethyl-tricyclo[5.2.1.0.sup.2,6 ]decane derivatives, notably the primary isomers of the common formula A, whereinR.sup.1 and R.sup.2 mean either methyl group or hydrogen, one of the substituents being a methyl group and the other hydrogen,R.sup.3 and R.sup.4 mean either methyl group or hydrogen, one of the substituents being a methyl group and the other hydrogen, andX indicates the .pi.-system of a C-C double bond or an epoxide system, can advantageously be used as new acent- and flavor materials.The compounds of the common formula A, were prepared by hydrogenation of dimeric methylcyclopentadiene selectively in the norbornane part and when desired by epoxidation of the remaining double bond.
    Type: Grant
    Filed: September 19, 1986
    Date of Patent: November 24, 1987
    Assignee: DRAGOCO Gerberding & Co. GmbH
    Inventors: Ernst-Joachim Brunke, Hartmut Struwe
  • Patent number: 4655484
    Abstract: A hexanes stream, including normal hexane, isohexanes, methylcyclopentane and cyclohexane is isomerized by first fractionating the hexanes stream in a first fractionation step to produce a normal hexaneisohexanes rich overhead stream and a methylcyclopentane-cyclohexane rich bottoms stream, the bottom stream of the first fractionation step is isomerized to maximize the conversion of methylcyclopentane to cyclohexane, the overhead stream from the first fractionation step is fractionated in a second fractionation step to produce an isohexane rich overhead stream and a normal hexane rich bottoms stream, the effluent from the isomerization step is fractionated in at least one stage of a third fractionation step to produce a cyclohexane rich bottoms fraction and a methylcyclopentane-isohexane rich overhead stream and at least a part of the overhead stream from the third fractionation step is recycled to at least one of the isomerization steps and the first fractionation step.
    Type: Grant
    Filed: December 16, 1982
    Date of Patent: April 7, 1987
    Assignee: Phillips Petroleum Company
    Inventor: William C. Rahlwes
  • Patent number: 4654452
    Abstract: A hexanes stream, conventionally produced in petroleum refining, comprising normal hexane, isohexanes, methylcyclopentane, and cyclohexane is isomerized to produce primarily cyclohexane and to recover normal hexane by first fractionating the hexanes stream in a first fractionation step in a manner and under conditions to produce a normal hexane-isohexane rich overhead stream and a methylcyclopentane-cyclohexane rich bottoms stream, the bottoms stream is isomerized in the presence of an isomerization catalyst and under conditions sufficient to maximize the conversion of methylcyclopentane to cyclohexane, the overhead from the first fractionation step and the effluent from the isomerization step is then fractionated in at least one stage of a second fractionation step in a manner and under conditions to produce separate streams, comprising isohexanes, normal hexane, cyclohexane, and unreacted methylcyclopentane and the methylcyclopentane is recycled to the isomerization step and/or the first fractionation step.
    Type: Grant
    Filed: December 16, 1982
    Date of Patent: March 31, 1987
    Assignee: Phillips Petroleum Company
    Inventors: William C. Rahlwes, Ralph G. Carrasco, Jr.
  • Patent number: 4564718
    Abstract: A method of preparing a functionally terminated polymer comprising polymerizing a terpene or an oxygen derivative thereof having a double bond or conjugated double bond available for polymerization with an initiator having a grouping which provides, or is a precursor of, the functional termination for the polymer.
    Type: Grant
    Filed: August 14, 1984
    Date of Patent: January 14, 1986
    Assignee: The University of Manchester Institute of Science and Technology
    Inventors: Richard H. Still, John L. Cawse, John L. Stanford
  • Patent number: 4459419
    Abstract: Zeolite-ruthenium catalysts in which the ruthenium is in the form of a cation are very effective in catalyzing the hydrogenation of a broad range of organic compounds.
    Type: Grant
    Filed: September 2, 1982
    Date of Patent: July 10, 1984
    Assignee: Ethyl Corporation
    Inventor: Paul D. Seemuth
  • Patent number: 4384981
    Abstract: The instant invention relates to a novel hydrogenation catalyst comprising a composite of a Group VIII metal or Group VIII metal compound and a compound selected from the group consisting of compounds represented by the general formulaM(O.sub.3 ZO.sub.x R).sub.nwherein M comprises a tetravalent metal, Z comprises a pentavalent atom, R is selected from the group consisting of hydrogen, organo radicals and mixtures thereof provided that at least a portion of said radicals comprise a moiety selected from the group consisting of pyridyl, allyl, anthranilic acid radicals and mixtures thereof; x is 0 or 1, and n is 2, provided that n is 1 when R is terminated with a tri- or tetra-oxy pentavalent atom. This catalyst is useful in hydrogenation processes which comprise contacting said catalyst with an unsaturated compound, said unsaturated compound comprising at least one unsaturated bond, e.g., a carbon-carbon bond, a carbon-nitrogen bond, a carbon-oxygen bond, or a nitrogen-oxygen bond, etc.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: May 24, 1983
    Assignee: Occidental Research Corporation
    Inventors: Martin B. Dines, Peter M. DiGiacomo, Kenneth P. Callahan
  • Patent number: 4356337
    Abstract: Benzene or an alkylbenzene is reacted with hydrogen and an alkali metal such as potassium in the presence of a polyamine to produce cyclohexene or alkylcyclohexene and alkali metal hydride. The polyamine contains only C, N and H and has at least three nitrogens. Each nitrogen is linked to three carbons and each carbon bridge is at least two methylenes long. Representative polyamines are hexamethyl hexacyclen, hexamethyl triethylene tetraamine, tris(2-dimethylamino ethyl)amine and octamethyl pentaethylene hexamine. Cyclohexene is produced at high ratios with respect to cyclohexane.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: October 26, 1982
    Assignee: Allied Corporation
    Inventors: Guido P. Pez, Irving L. Mador
  • Patent number: 4320239
    Abstract: 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: Grant
    Filed: February 13, 1981
    Date of Patent: March 16, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: Wolfgang Schneider
  • Patent number: 4310714
    Abstract: Ruthenium has been found to be a stereoselective catalyst for the hydrogenation of .alpha.-pinene to obtain cis-pinane.
    Type: Grant
    Filed: December 10, 1980
    Date of Patent: January 12, 1982
    Assignee: Union Camp Corporation
    Inventor: Mark S. Pavlin
  • Patent number: 4273944
    Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 16, 1981
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
  • Patent number: 4227028
    Abstract: A process for regioselective isomerization of organic compounds having a carbon-carbon double bond at a tertiary carbon atom by sulfur dioxide induced allylic rearrangement of a hydrogen atom and/or replacement of a proton in the allylic position by a deuteron. The organic compound is contacted with sulfur dioxide at temperatures between about 0.degree. and 70.degree. C. for a time sufficient to effect such isomerization to a more stable isomer; and if deuteration is to take place D.sub.2 O is provided in the solution.
    Type: Grant
    Filed: March 1, 1979
    Date of Patent: October 7, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4204080
    Abstract: Non-conjugated para-menthadienes having one site of unsaturation at the 4(8)- or 8-position are hydrogenated to selectively form 3-menthene in the presence of a homogeneous ruthenium catalyst complex.
    Type: Grant
    Filed: January 22, 1979
    Date of Patent: May 20, 1980
    Assignee: SCM Corporation
    Inventors: James O. Bledsoe, Jr., Carlos G. Cardenas