Isomerization Patents (Class 568/384)
  • Patent number: 9573872
    Abstract: The present invention relates to a process of manufacturing compound having stereogenic centers from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centers. The process involves an asymmetric hydrogenation and an isomerization step. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: February 21, 2017
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jonathan Alan Medlock, René Tobias Stemmler, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries
  • Patent number: 8802898
    Abstract: Isomerization of ?-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding ?,?-dienones of formula II by treatment with a basic ion exchange resin.
    Type: Grant
    Filed: April 18, 2011
    Date of Patent: August 12, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Reinhard Karge, Thomas Netscher, Yann Pressel
  • Publication number: 20130197272
    Abstract: Isomerization of ?-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding ?,?-dienones of formula II by treatment with a basic ion exchange resin.
    Type: Application
    Filed: April 18, 2011
    Publication date: August 1, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Reinhard Karge, Thomas Netscher, Yann Pressel
  • Patent number: 7176177
    Abstract: 4,8-dimethyl-3,7-nonadien-2-one has aromatizing properties and increases the extendibility and intensity of the aroma when used in an aroma composition.
    Type: Grant
    Filed: December 4, 2000
    Date of Patent: February 13, 2007
    Assignee: Symrise GmbH & Co. KG
    Inventors: Stefan Lambrecht, Günter Kindel, Erich Dilk, Matthias Güntert
  • Patent number: 6933413
    Abstract: The present invention provides a process for the preparation of hexafluoroacetone characterized by bringing hexafluoro-1,2-epoxypropane into contact with at least one catalyst selected from the group consisting of titanium oxide catalysts and fluorinated titanium oxide catalysts to isomerize hexafluoro-1,2-epoxypropane; and a process for the preparation of hexafluoroacetone hydrate characterized by absorbing the hexafluoroacetone prepared by the above process into water to produce crude hexafluoroacetone hydrate, neutralizing the crude hexafluoroacetone hydrate with an alkali, and distilling the resulting mixture. According to the invention, high-purity hexafluoroacetone can be obtained by isomerization of hexafluoro-1,2-epoxypropane with little formation of by-products, and substantially acid-free high-purity hexafluoroacetone hydrate can also be obtained.
    Type: Grant
    Filed: July 2, 2002
    Date of Patent: August 23, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
  • Publication number: 20030149309
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Application
    Filed: February 26, 2003
    Publication date: August 7, 2003
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6310258
    Abstract: The invention provides a process for preparing 1,3-diketones by rearrangement of the isomeric enol ester in a tube reactor comprising a heated portion and an unheated insulated portion which can optionally be provided with cooling means. The unheated portion of the reactor has a higher volume to surface ratio than the heated portion of the reactor. The reaction can be carried out adiabatically in the unheated portion of the reactor. The process and apparatus provide higher yields and selectivity to the 1,3-diketones.
    Type: Grant
    Filed: July 31, 2000
    Date of Patent: October 30, 2001
    Assignee: Wacker Chemie GmbH
    Inventors: Dominik Dempf, Thomas List, Wolfgang Deinhammer, Georges Heyen
  • Patent number: 6300523
    Abstract: This invention is intended to provide a method for producing pinacoline by means of pinacol rearrangement in supercritical water, which affords an extremely high reaction rate without the addition of high concentrations of acid, and this invention is directed to a method for increasing the reaction rate during organic synthesis by utilizing the supply of protons from water under noncatalytic conditions in supercritical water, a method of pinacol rearrangement comprising the production of pinacoline by pinacol rearrangement under noncatalytic conditions without the addition of an acid catalyst in supercritical water, and a method of synthesis comprising the production of cyclic compounds from pinacol under noncatalytic conditions without the addition of an acid catalyst around the critical point (375 to 380° C., 22.5 to 25 MPa) in supercritical water.
    Type: Grant
    Filed: October 27, 1999
    Date of Patent: October 9, 2001
    Assignee: Agency of Industrial Science and Technology
    Inventors: Yutaka Ikushima, Osamu Sato
  • Patent number: 5576462
    Abstract: A process for the preparation of .alpha.-hydroxyketones of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 denote hydrogen or C.sub.1 -C.sub.8 alkyl orR.sub.1 and R.sup.3 together form a C.sub.2 -C.sub.10 alkylene chain optionally mono- to tri-substituted by methyl and/or ethyl andR.sup.5 denotes hydrogen, methyl or ethyl,from 2,3-epoxyalcohols of the general formula II ##STR2## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 have the above meanings, at temperatures of from -10.degree. to 120.degree. C. and pressures of from 0.01 to 20 bar in the presence of a catalyst, wherein the catalyst used is a hydridocobalt compound, and the preparation of 2,3-epoxyalcohols II from 3-hydroperoxy alkenes III and their preparation from alkenes IV using oxygen or gas mixtures containing oxygen.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: November 19, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Rieber, Joaquim H. Teles
  • Patent number: 5457238
    Abstract: This invention concerns a process for the preparation of fluoroketones by the isomerization of corresponding epoxides, in the presence of an aluminum chlorofluoride catalyst. Fluorinated ketones are useful intermediates for the synthesis of various fluorinated compounds.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: October 10, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Viacheslav A. Petrov, Bruce E. Smart
  • Patent number: 5102581
    Abstract: Process for the preparation of: ##STR1## by oxidative decarboxylation of an allyl .beta.-ketoester: ##STR2## in an organic solvent, in the presence of a palladium-based catalyst. The organic solvent selected from an amide, a nitrile, or a dinitrile.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: April 7, 1992
    Assignee: Rhone-Poulenc Sante
    Inventors: Claude Mercier, Gerard Mignani
  • Patent number: 5032323
    Abstract: Epoxides are isomerized to ketones by contacting the epoxides with a catalyst effective amount of a substantially fully hydrogenated palladium catalyst at a temperature of from about 200.degree. C. to about 300.degree. C. while contacting the epoxides with hydrogen at a partial pressure of equal to or less than one atmosphere.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: July 16, 1991
    Assignee: Henkel Research Corporation
    Inventor: Michael J. Virnig
  • Patent number: 4980511
    Abstract: Aldehydes and ketones are prepared from epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each alkyl, alkenyl, aryl, alkoxy or aralkyl and R.sup.3 has the same meanings or is hydrogen, by a catalytic rearrangement reaction in the presence of various catalysts, in particular zeolites of the pentasil type.
    Type: Grant
    Filed: September 25, 1987
    Date of Patent: December 25, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Helmut Lermer
  • Patent number: 4950797
    Abstract: A process for the preparation of carbonyl compounds by catalyzed isomerization of allyl alcohols in a tertiary phosphine or phosphite ester in the presence of a rhodium compound at a temperature of from 80.degree. C. to 180.degree. C., a carrier gas being passed through the reaction mixture and the carbonyl compound being separated from the emergent gas mixture by cooling.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
  • Patent number: 4925985
    Abstract: A process for the production of 4,6-dimethyl-7-hydroxynonan-3-one of specific stereochemistry is disclosed. The process results in an active (+)-serricornin.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: May 15, 1990
    Assignee: Philip Morris Incorporated
    Inventors: David L. Williams, William B. Edwards, III, Richard H. Cox, Daryl L. Faustini, Surnease Drew
  • Patent number: 4845301
    Abstract: A process for the preparation of .alpha.-hydroxyketones ##STR1## having a high purity in a good yield from a compound ##STR2## by rearrangement reaction in aqueous alkaline solution, where R.sub.1 and R.sub.3 each represent an alkyl, alkenyl or aryl group, R.sub.2 represents a hydrogen atom or an alkyl, alkenyl or aryl group, and X represents hydroxyl group or a halogen atom.
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: July 4, 1989
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kazuo Sato, Noritsugu Yamasaki, Ichirou Takase
  • Patent number: 4749814
    Abstract: Ethylenic carbonyl compounds of formula ##STR1## are made by the isomerization of acetylenic alcohols of formula ##STR2## in the presence of a catalyst consisting of a titanium derivative, a copper or silver derivative, and, if required, an acid, which may be in the form of an ester or anhydride, or an inorganic ester.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 7, 1988
    Assignee: Rhone-Poulenc Sante
    Inventor: Pierre Chabardes
  • Patent number: 4734529
    Abstract: The method for the isomerization of oxiranes of the general formula: ##STR1## wherein R.sub.1 and R.sub.3 are hydrogen; R.sub.2 is alkyl or alkylene groups of 3 to 26 carbon atoms or the phenyl group which may also be substituted, and R.sub.4 is hydrogen or alkyl from 1 to 26 carbon atoms and in which the carbon atoms of the epoxy ring can also form components of a cyclic system, wherein as a catalyst there is used alkali iodide and a polyethyleneglycol with an average mol mass of 400 to 10,000 with a boiling point, preferably above the boiling point of the carbonyl compounds that are formed.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: March 29, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Marion Berg, Andreas Grund, Guenter Prescher
  • Patent number: 4721820
    Abstract: A process for isomerizing allylic ethers is disclosed. In this process a compound having the structural formulaCH.sub.2 .dbd.CH--CH(OR)--R.sup.1where R is hydrocarbyl; and R.sup.1 is an organo group is contacted with a hydroxy-containing compound and a catalytically effective amount of a catalyst selected from the group consisting of cupric chloride, cupric bromide, a mixture of cupric chloride and palladium chloride, a mixture of cupric chloride and palladium bromide, a mixture of cupric bromide and palladium chloride and a mixture of cupric bromide and palladium bromide whereby a compound having the structural formulaRO--CH.sub.2 --CH.dbd.CH--R.sup.1where R and R.sup.1 have the meanings given above is formed.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: January 26, 1988
    Assignee: National Distillers and Chemical Corporation
    Inventor: Ronnie M. Hanes
  • Patent number: 4695673
    Abstract: An acylated 1,3-dicarbonyl compound is produced by rearrangement of the corresponding enol ester in the presence of a cyanide source. In one embodiment the cyanide source is employed with a molar excess of a moderate base, with respect to the enol ester. In another embodiment, the cyanide source is a stoichiometric amount, with respect to the enol ester, of potassium or lithium cyanide and a catalytic amount of a crown ether is used.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: September 22, 1987
    Assignee: Stauffer Chemical Company
    Inventors: James B. Heather, Pamela D. Milano
  • Patent number: 4694107
    Abstract: Ketones are prepared by isomerization of aldehydes at elevated temperatures over zeolites.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: September 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Rolf Fischer
  • Patent number: 4609764
    Abstract: Stereoisomers having no cigarette beetle's sex pheromone activity contained in synthesized 4,6-dimethyl-7-hydroxy-nonan-3-one which is an equilibrium mixture of eight stereoisomers may be converted into stereoisomer having said sex pheromone activity by repeating column chromatographic fractionation, epimerization with an acidic or a basic catalyzer and/or racemization with a basic catalyzer in relation to said 3-one compound.
    Type: Grant
    Filed: December 26, 1984
    Date of Patent: September 2, 1986
    Assignees: The Japan Tobacco & Salt Public Corporation, Fuji Flavor Company, Limited
    Inventors: Mori Masataka, Chuman Tatsuji, Kato Kunio, Ono Mikio
  • Patent number: 4537995
    Abstract: A process of isomerizing branched aldehydes to ketones is provided which comprises contacting at isomerization conditions a branched aldehyde with a zeolite catalyst of the formula: ##EQU1## wherein M is selected from the group consisting of a mixture of alkali metal cations, especially sodium, and tetraalkylammonium cations, the alkyl groups of which preferably contain 2 to 5 carbon atoms, and x is at least 5. The contacting is conducted at a temperature of from about 200.degree. C. to about 600.degree. C. and at a pressure of from about 20 psig to about 100 psig. The branched aldehyde is contacted in the presence of water in a molar ratio of water-to-aldehyde of up to about 20 to 1.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: August 27, 1985
    Assignee: Celanese Corporation
    Inventors: H. Clay Linstid, III, Gerald S. Koermer
  • Patent number: 4508923
    Abstract: There is disclosed an improved process for oxidizing a hydrocarbon to produce a reaction mixture containing the corresponding organic hydroperoxide of said hydrocarbon and decomposing said hydroperoxide to provide a mixture containing reaction products of said decomposition reaction, including alcohol and/or ketone products, comprising effecting said oxidation and/or decomposition in the presence of a catalytic quantity of a catalyst system comprised of ruthenium and chromium.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: April 2, 1985
    Assignee: Atlantic Richfield Company
    Inventors: Paul D. Taylor, Michael T. Mocella
  • Patent number: 4476147
    Abstract: A process for augmenting or enhancing the aroma or taste of alliaceous flavors, particularly garlic flavors, by augmenting or enhancing the garlic and green aroma and taste nuances of alliaceous-flavored foodstuffs comprising the step of adding to a alliaceous-flavored foodstuff an aroma or taste augmenting quantity of a mixture of cis and trans isomers of a compound having the structure: ##STR1## wherein the wavy lines indicate both cis and trans juxtaposition of the hydrogen and methallyl moieties about the carbon-carbon double bond.
    Type: Grant
    Filed: October 17, 1983
    Date of Patent: October 9, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, James M. Sanders, James N. Siano
  • Patent number: 4460801
    Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.
    Type: Grant
    Filed: June 28, 1983
    Date of Patent: July 17, 1984
    Assignee: Rhone-Poulenc Industries
    Inventor: Didier Morel
  • Patent number: 4451672
    Abstract: Methyl ethyl ketone is produced in quantitative yields by isomerizing 1,2-butylene oxide or isomeric mixtures of n-butylene oxides in the presence of a tertiary butyl alcohol solution of dicobalt octacarbonyl.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: May 29, 1984
    Assignee: Atlantic Richfield Company
    Inventor: Roger A. Grey
  • Patent number: 4424399
    Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.
    Type: Grant
    Filed: September 9, 1980
    Date of Patent: January 3, 1984
    Assignee: Rhone-Poulenc Industries
    Inventor: Didier Morel
  • Patent number: 4421934
    Abstract: Process for the preparation of .delta.-ethylenic carbonyl compounds of the formula (I) by the oxy-Cope rearrangement of a diethylenic alcohol of the formula (II), in the presence of a mercuric salt: in formulae (I) and (II), R.sub.1, R.sub.2, R.sub.4, R.sub.5 and R.sub.6, which are identical or different, represent a hydrogen atom or an acyclic hydrocarbon radical and R.sub.3 represents an acyclic hydrocarbon radical, it being understood that R.sub.1 and R.sub.3 can together form a trimethylene radical, or alternatively that R.sub.3 and R.sub.4 can together form an alkylene radical containing 3 to 20 carbon atoms.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: December 20, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Norbert Bluthe, Jacques Gore, Max Malacria
  • Patent number: 4329506
    Abstract: Aldehydes, such as isobutyraldehyde, are isomerized to ketones, such as methyl ethyl ketone, by contact at isomerization conditions, typically vapor-phase conditions, with a catalyst of the formula M.sub.0.15-15 M'.sub.0.05-12 O.sub.x where M is at least one of Mo and Cu and M' is a promoter, such as a Group IIB or VIII element.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: May 11, 1982
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Andrew S. Krupa
  • Patent number: 4302608
    Abstract: A continuous process for the isomerization of hexafluoropropylene oxide to hexafluoroacetone comprises passing hexafluoropropylene oxide in contact with liquid antimony pentafluoride adsorbed on a solid support under conditions which substantially prevent loss of antimony pentafluoride from the reactor in which the isomerization is carried out and removing the hexafluoroacetone product at about the same rate as that at which it is formed. Hexafluoroacetone is an important industrial monomer, which can be copolymerized, for example, with ethylene and tetrafluoroethylene to a product that finds use in coating electrical wires.
    Type: Grant
    Filed: August 20, 1980
    Date of Patent: November 24, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Edward N. Squire
  • Patent number: 4246200
    Abstract: This invention relates to compounds having the formula ##STR1## in which R.sub.F is a perfluoro radical C.sub.n F.sub.2n+1 with n=1-20, and R is a C.sub.1-20 alkyl radical, a C.sub.4-15 cycloalkyl radical, a C.sub.5-20 cycloalkyl-alkyl radical, or a C.sub.6-20 aromatic radical.Said compounds constitute valuable intermediates for the synthesis of surface-active agents.
    Type: Grant
    Filed: May 29, 1979
    Date of Patent: January 20, 1981
    Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)
    Inventors: Claude Wakselman, Marc Tordeux
  • Patent number: 4238416
    Abstract: A method for isomerization of fluorinated epoxy compounds by contacting with a catalyst to produce the corresponding fluorinated carbonyl compounds, which is characterized in that the catalyst is a fluorinated alumina or a fluorinated silica alumina.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: December 9, 1980
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Takashi Tohzuka, Yohnosuke Ohsaka
  • Patent number: 4222963
    Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## and; .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.
    Type: Grant
    Filed: February 28, 1979
    Date of Patent: September 16, 1980
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara