Four-membered Alicyclic Ring Containing Patents (Class 568/839)
  • Patent number: 4987236
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom, R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: January 22, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4968848
    Abstract: A process for the preparation of perfluoroalkyl compounds which comprises reacting a perfluoroalkyl-trimethylsilane of the general formula (CH.sub.3).sub.3 Si-C.sub.n F.sub.2n+1 (I), wherein the group C.sub.n F.sub.2n+1 represents a perfluoroalkyl group having from 1 to 6 carbon atoms, with a carbonyl compound of the general formula F.sup.1 --CO--R.sup.2 (II), wherein R.sup.1 represents a hydrocarbon group or hydrogen and R.sup.2 represents a hydrocarbon group, a perfluoroalkyl group or a perfluoroaryl group, but wherein R.sup.1 and R.sup.2 together may also be part of an alicyclic ring system, in the presence of a salt-like fluoride--which is at least partially soluble in the reaction medium--as a catalyst to yield a silylether of the formula ##STR1## and isolating this compound or hydrolyzing it to yield an alcohol of the formula IV ##STR2## The invention also relates to pentafluoroethyl trimethylsilane (CH.sub.3).sub.3 Si--CF.sub.2 CF.sub.3 and a process for the preparation of this compound.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: November 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Alfred Kruse, Gunter Siegemund, Axel Schumann
  • Patent number: 4958033
    Abstract: A process for preparing an alcohol of the formula: ##STR1## by reacting a carbonyl compound of the formula: ##STR2## or an oxirane of the formula: ##STR3## magnesium and a propargyl halide of the formula: ##STR4## followed by hydrolysis, characterized in that the carbonyl compound (II) or the oxirane compound (III) and the propargyl halide (IV) are reacted simultaneously with magnesium in an inert solvent in the presence of zinc or a halide thereof.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: September 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
  • Patent number: 4933511
    Abstract: An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II ##STR1## wherein: X.sup.1, X.sup.2 and X.sup.3 independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C.sub.1 to C.sub.6 alkyl, C.sub.1 and C.sub.6 haloalkyl, and haloaryl; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R.sup.3 and R.sup.4 is as hereinbefore defined and R.sup.1 and R.sup.2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene or formula IV in the presence of an optically-active organometallic catalyst. ##STR2## Furthermore, the compound of formula II can be isomerized to the allylic alcohol of formula I with retention of optical purity.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: June 12, 1990
    Assignee: ICI Australia Limited
    Inventors: Matthew Gredley, Colin Wilshire
  • Patent number: 4902812
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom. R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: February 20, 1990
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4864037
    Abstract: Disclosed are new 1,3-dioxenones having the formulae ##STR1## in an optically pure state, a process for preparing same and the use thereof.
    Type: Grant
    Filed: July 21, 1987
    Date of Patent: September 5, 1989
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Kurt Schaffner, Martin Demuth
  • Patent number: 4855460
    Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Tordeux, Claude Wakselman, Catherine Francese
  • Patent number: 4822925
    Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: April 18, 1989
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, John H. Robson
  • Patent number: 4806694
    Abstract: Fluorine-containing polyols obtained by the free radical addition of a fluoro-olefin having the general formula: ##STR1## wherein Y represents F and Z represents Cl or F(CF.sub.2)n--wherein n is an integer from 0 to 10 or Y and Z together form a --(CF.sub.2)m-- chain wherein m represents an integer from 2 to 4 to a polyol wherein each hydroxyl group is directly attached to a group of the formula:--(CH.sub.2).sub.p O-- (2)wherein p is an integer of at least 4.
    Type: Grant
    Filed: September 10, 1987
    Date of Patent: February 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Richard L. Powell, Brian Young
  • Patent number: 4551566
    Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in the presence of a vanadate salt wherein the pH of the liquid phase is between about 5 and 12.
    Type: Grant
    Filed: September 8, 1983
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventors: John H. Robson, George E. Keller, II
  • Patent number: 4507512
    Abstract: An improved process for producing an alcohol by hydrating an olefin wherein the improvement comprises hydrating an olefin in the presence of a hydrogen-type catalyst having a silica/alumina molar ratio of 20 to 500 and a solvent using either:A. hydrogen-type mordenite or hydrogen-type zeolite Y, and a sulfone; orB. hydrogen-type crystalline aluminosilicate in which the entrance of the main void is formed by a 10-membered or 12-membered oxygen ring, and a C.sub.2 to C.sub.5 oxy acid or the lactones, lactides, methyl or ethyl esters thereof.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: March 26, 1985
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Yoshiharu Okumura, Setsuo Kamiyama, Hiroshi Furukawa, Katsumi Kaneko
  • Patent number: 4499313
    Abstract: An improved process for producing an alcohol by hydrating an olefin, wherein the improvement comprises hydrating an olefin in the presence of hydrogen-type mordenite or hydrogen-type zeolite Y as a catalyst each having a silica/alumina molar ratio of 20 to 500.
    Type: Grant
    Filed: April 30, 1984
    Date of Patent: February 12, 1985
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Yoshiharu Okumura, Setsuo Kamiyama, Toshihiro Hosokawa, Katsumi Kaneko
  • Patent number: 4486613
    Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an oxidant selected from organic hydroperoxides, H.sub.2 O.sub.2, and oxygen and a catalyst composition comprising at least one osmium carbonyl catalyst, such as Os.sub.3 (CO).sub.12, and optionally at least one cocatalyst such as NaI, is disclosed.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: December 4, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
  • Patent number: 4438287
    Abstract: Alcohols may be prepared in a combination process by subjecting an aliphatic paraffinic hydrocarbon feed stream to a dehydrogenation reaction and thereafter subjecting the reaction product mix comprising a mixture of aliphatic paraffinic hydrocarbons and aliphatic olefinic hydrocarbons, without separating the olefins in the product mix from the paraffins, to a hydroformylation reaction. The hydroformylation reaction is effected by treating said product mix with carbon monoxide and hydrogen in the presence of a catalyst comprising a rhodium-containing compound and a promoter comprising a trialkyl-substituted monoamine, all three of said alkyl moieties being substituted to the nitrogen of said amine to selectively prepare the desired alcohols.
    Type: Grant
    Filed: August 25, 1982
    Date of Patent: March 20, 1984
    Assignee: UOP Inc.
    Inventor: Tamotsu Imai
  • Patent number: 4385185
    Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: May 24, 1983
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Walter Hafner
  • Patent number: 4338290
    Abstract: Glycols are readily and conveniently prepared by hydrolysis of halohydrins and/or dihaloalkanes in the presence of a catalytically effective amount of a strong acid.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: July 6, 1982
    Assignee: National Distillers & Chemical Corp.
    Inventors: Jawad H. Murib, John M. Inskeep
  • Patent number: 4327230
    Abstract: A process for the continuous production of an alkali metal alcoholate of a higher alcohol which comprises continuously introducing a higher alcohol into a reaction vessel, continuously introducing an alkali metal alcoholate of a lower alcohol into said reaction vessel and continuously and simultaneously distilling over and removing from said reaction vessel lower alcohol which forms.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: April 27, 1982
    Assignee: Dynamit Nobel AG
    Inventors: Otto Ackermann, Hans Leuck, Gunther Meyer, Gerhard Schmeling
  • Patent number: 4273947
    Abstract: A process is described for the heterogeneous hydrogenation of fluorine-containing alkyl, cycloalkyl, and benzene carboxylic acids to the corresponding primary alcohols. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture thereof. In the liquid phase, the hydrogenation can be carried out batchwise under mild conditions of temperature and pressure, preferably at about 50.degree.-150.degree. C. and about 5-15 atmospheres, in an atmosphere containing hydrogen gas. A preferred embodiment is the hydrogenation of trifluoroacetic acid in the liquid phase to 2,2,2-trifluoroethanol, said alcohol being useful as an intermediate in the synthesis of the anesthetic, isoflurane, CF.sub.3 CHClOCHF.sub.2.
    Type: Grant
    Filed: January 31, 1979
    Date of Patent: June 16, 1981
    Assignee: Allied Chemical Corporation
    Inventor: Miroslav Novotny
  • Patent number: 4271091
    Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.
    Type: Grant
    Filed: June 17, 1978
    Date of Patent: June 2, 1981
    Assignee: Standard Oil Company
    Inventors: Robert K. Grasselli, Dev D. Suresh
  • Patent number: 4220795
    Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: September 2, 1980
    Assignee: Miles Laboratories, Inc.
    Inventors: Harold C. Kluender, Henry C. Arndt
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4197245
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: April 8, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4191696
    Abstract: A new liquid phase oxidation process in which a metal nitro complex transfers an oxygen atom from the nitro ligand to a substrate; especially such process conducted cyclically or catalytically using molecular oxygen as the oxygen source. Metal nitrosyl complex is formed as a coproduct together with an oxidation product of the substrate. In a catalytic process, molecular oxygen maintains a concentration of nitro ligand in the reaction mixture. In a cyclic process, nitrosyl ligand of the metal nitrosyl coproduct is reoxidized by molecular oxygen in presence of a monodentate base such as pyridine to nitro ligand; and the nitro complex, thus regenerated, can be used again to oxidize the substrate, In particular the metal is a Group VIII metal, especially cobalt and the nitro complex is pyridine cobalt nitro saloph. To accelerate oxidation of the substrate at given temperature, a cocatalyst is included in the reaction mixture, e.g.
    Type: Grant
    Filed: July 24, 1978
    Date of Patent: March 4, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Benjamin S. Tovrog, Steven E. Diamond, Frank Mares
  • Patent number: 4172839
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 30, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4170597
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 9, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4113968
    Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.
    Type: Grant
    Filed: September 26, 1975
    Date of Patent: September 12, 1978
    Assignee: Kuraray Co., Ltd.
    Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi
  • Patent number: 4087468
    Abstract: Grignard reagents of halo-substituted conjugated dienes are prepared by reaction of 1- or 2-halo-substituted conjugated diene with magnesium metal employing a metal halide/saturated aliphatic halide catalyst system. The Grignard reagent can be employed in the preparation of hydroxy-substituted conjugated dienes and hydroxy-substituted allenes. Adjustment of the molar ratio of the metal halide to the halo-substituted conjugated diene permits favoring of hydroxy-substituted conjugated dienes or hydroxy-substituted allenes in the diene products.
    Type: Grant
    Filed: December 12, 1975
    Date of Patent: May 2, 1978
    Assignee: Phillips Petroleum Company
    Inventor: Paul W. Solomon