Acyclic Unsaturated Hydrocarbon Reactant Patents (Class 568/395)
  • Patent number: 9181163
    Abstract: The present invention relates in a first aspect to a process for hydrogenation of ketones having at least a carbon-carbon double bond in the y,8-position to the keto group by hydrogen in the presence of at least one chiral iridium complex of formula (I), where R1 represents a group of formula (II) or (III) or (IV). It has been shown that this process leads to a strong increase in preferential formation of a single isomer. The process is particularly suitable for the hydrogenation of y,8-unsaturated ketones which can be used as flavors and fragrances or for the preparation of vitamin E and its derivatives or of flavors and fragrances.
    Type: Grant
    Filed: June 13, 2012
    Date of Patent: November 10, 2015
    Assignee: DSM IP ASSETS B.V.
    Inventors: Marc-André Mueller, Andreas Pfaltz, Jonathan Medlock
  • Patent number: 8420866
    Abstract: The present invention relates to a process for preparing a ketone, comprising the reaction of a composition (I) at least comprising a 1,1-disubstituted olefin, with a composition comprising dinitrogen monoxide, wherein the reaction is effected in the presence of a solvent which comprises at least one proton-donating functional group.
    Type: Grant
    Filed: December 14, 2009
    Date of Patent: April 16, 2013
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Michael Schelper
  • Publication number: 20120123168
    Abstract: Hydrocarbons may be formed from six carbon sugars. This process involves obtaining a quantity of a hexose sugar. The hexose sugar may be derived from biomass. The hexose sugar is reacted to form an alkali metal levulinate, an alkali metal valerate, an alkali metal 5-hydroxy pentanoate, or an alkali metal 5-alkoxy pentanoate. An anolyte is then prepared for use in a electrolytic cell. The anolyte contains the alkali metal levulinate, the alkali metal valerate, the alkali metal 5-hydroxy pentanoate, or the alkali metal 5-alkoxy pentanoate. The anolyte is then decarboxylated. This decarboxylating operates to decarboxylate the alkali metal levulinate, the alkali metal valerate, the alkali metal 5-hydroxy pentanoate, or the alkali metal 5-alkoxy pentanoate to form radicals, wherein the radicals react to form a hydrocarbon fuel compound.
    Type: Application
    Filed: January 24, 2012
    Publication date: May 17, 2012
    Inventor: Sai Bhavaraju
  • Patent number: 7935849
    Abstract: Saturated aliphatic ketones, e.g. hexahydropseudoionone, may be prepared by hydrogenating an olefinically unsaturated ketone, e.g. pseudoionone in a continuous fixed-bed mode in the absence of a solvent in the presence of a catalyst comprising a noble metal deposited on a carrier.
    Type: Grant
    Filed: September 14, 2005
    Date of Patent: May 3, 2011
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Thomas Kircher, Rolf Kuenzi, Johannes Tschumi
  • Patent number: 7851658
    Abstract: A novel palladium-mediated carbon-carbon bond forming reaction has been discovered using DNA-templated chemistry. The inventive reaction involves the palladium-mediated coupling of a terminal alkyne with an alkene to form an enone. A catalytic amount of palladium may be used in the reaction if an oxidant is present. The reactions is also compatible with a variety of organic solvent as well as aqueous solution. Both intermolecular and intramolecular reactions have been demonstrated. This novel carbon-carbon bond forming reaction is particularly useful in the synthesis of macrocycles. Kits, reagents, catalysts, solvents, oxidants, salts, acids, instructions, and other materials useful in the practice of the inventive reaction are also provided.
    Type: Grant
    Filed: August 17, 2005
    Date of Patent: December 14, 2010
    Assignee: President and Fellows of Harvard College
    Inventors: David R. Liu, Matthew W. Kanan, Mary M. Rozenman
  • Patent number: 7541307
    Abstract: A silicon enolate represented by the following formula (Formula 1) (in the formula, R5 to R7 represent hydrogen atoms, aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, monocyclic or polycyclic aromatic or aromatic-aliphatic hydrocarbon groups or heterocyclic groups, R5 and R7 are different, R6 is not a hydrogen atom, each R8 may be identical or different and represents a methyl group, ethyl group or isopropyl group) and formaldehyde are allowed to react in an aqueous solution or a mixed solvent of water and an organic solvent in the presence of a catalyst obtained by mixing a ligand comprising a chiral bipyridine compound or its antipode and Bi(OTf)3.
    Type: Grant
    Filed: January 27, 2006
    Date of Patent: June 2, 2009
    Assignee: Japan Science and Technology Agency
    Inventors: Shu Kobayashi, Kei Manabe
  • Publication number: 20080242893
    Abstract: The present invention relates to a process for preparing optically active bisphosphinylalkanes from the correspondingly substituted, racemic 1,2-diols. The optically active bisphosphinylalkanes which can be obtained in this way are suitable as ligands for preparing chiral transition metal catalysts.
    Type: Application
    Filed: July 26, 2006
    Publication date: October 2, 2008
    Applicant: BASF Aktiengesellschaft
    Inventors: Christoph Jaekel, Rocco Paciello
  • Patent number: 7067702
    Abstract: A process for preparing vinyl substituted beta-diketones includes reacting a halogen-containing beta-diketone with an olefin in a reaction zone under Heck coupling reaction conditions in the presence of a catalyst, a base, and an organic phosphine to provide a vinyl substituted beta-diketone product.
    Type: Grant
    Filed: May 12, 2005
    Date of Patent: June 27, 2006
    Assignee: The Johns Hopkins University
    Inventors: Glen E. Southard, George M. Murray
  • Patent number: 6723882
    Abstract: Dialkyl ketones are prepared by reductive carbonylation of &agr;-olefins by means of carbon monoxide and hydrogen in the presence of a catalyst system comprising (a) palladium or a palladium compound; (b) a phosphine; (c) a protic acid having a pKa of ≦4.5, measured in aqueous solution at 25° C.; and (d) a solubilizable carboxamide.
    Type: Grant
    Filed: July 18, 2002
    Date of Patent: April 20, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Slany, Martin Schäfer, Michael Röper
  • Patent number: 6703528
    Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: March 9, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
  • Patent number: 6369277
    Abstract: An &agr;,&bgr;-unsaturated carbonyl compound of formula (I) where R1 is saturated C1-40-hydrocarbyl or a substituted or unsubstituted aromatic radical containing moiety, and R2, R3 and R4, independently of one another, are hydrogen or a C1- to C4-alkyl group, is selectively hydrogenated in the liquid phase to a saturated carbonyl compound of formula (II) with hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base, by conducting the hydrogenation in a packed bubble column reactor in which product is recycled and hydrogen gas is recirculated.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: April 9, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Josef Broecker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Guenter Wegner, Manfred Stroezel
  • Patent number: 6353139
    Abstract: A method for preparing ketones has advantages of improving yields and reducing the time of the reactions due to high efficiency of catalysts. Ketones are prepared by reacting an aliphatic or an aromatic aldehyde with a vinyl olefin having an aliphatic or aromatic alkyl moiety in the presence of a transition metal catalyst, 2-aminopyridine catalyst, a primary amine and an acid, as catalysts and additives.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: March 5, 2002
    Inventors: Chul Ho Jun, Dae Yon Lee, Hyuk Lee, Jun Bae Hong
  • Patent number: 6252118
    Abstract: A method for preparation of a new ketone from a preexisting ketone is very advantageous in terms of production cost and yield. A reactant mixture consisting of a ketone containing &bgr;-hydrogen relative to the aldehyde group and a vinyl olefin or internal olefin having an aliphatic or aromatic alkyl moiety is allowed to react at approximately 100-180° C. for at least 6 hours in the presence of a rhodium or iridium transition metal catalyst and a 2-aminopyridine derivative.
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: June 26, 2001
    Inventors: Chul Ho Jun, Hyuk Lee
  • Patent number: 6049010
    Abstract: A method for preparation of a dicarbonyl compound of the following formula ##STR1## by reacting a conjugated alkadiene compound of the formula ##STR2## with a 1,3-dicarbonyl compound of the formula ##STR3## in the presence of an acid catalyst. The products of the method are useful in the preparation of compounds such as vitamins A and E, various carotenoids, Retin A, dehydrolinalool, pseudoionone, citral, and linalool.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: April 11, 2000
    Assignee: Loyola University of Chicago
    Inventors: James H. Babler, Harvey W. Posvic
  • Patent number: 6034279
    Abstract: An improved process is described for preparing .gamma.,.delta.-unsaturated ke-tones, which are in demand as aroma substances and intermediates for vitamins and carotenoids, by reacting tertiary allyl alcohols and alkenyl alkyl ethers in the presence of acid catalysts at elevated temperature, which comprises carrying out the reaction in the presence of a phosphorus derivative of the formula IV ##STR1## where A and B are each a branched or unbranched alkyl or alkoxy having from 1 to 10 carbons, a substituted or unsubstituted aryl, cycloalkyl, aryloxy or cycloaryloxy;A can additionally be --H or --OH orA and B together are a substituted or unsubstituted tetramethylene or pentamethylene or substituted or unsubstituted phenyl-1,2-diol or 1,1'-binaphthyl-2,2'-diol.
    Type: Grant
    Filed: January 29, 1999
    Date of Patent: March 7, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Kashammer, Detlef Ruff
  • Patent number: 6002047
    Abstract: The present invention is concerned with a process for the catalytic hydrogenation of organic compounds on a catalyst of amorphous metal alloys and in a solvent, with the hydrogenation being carried out under near-critical or supercritical conditions of the solvent. The amorphous metal alloys can be produced by the shock cooling of alloy melts having eutectic solidification points. By hydrogenation at hydrogen partial pressures between 5 and 400 bar there is obtained outstanding space-time yields with high long-term stability of the catalytic activity.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: December 14, 1999
    Assignee: Roche Vitamins Inc.
    Inventors: Michael Jansen, Claus Rehren
  • Patent number: 5932684
    Abstract: A process for preparing keto-functional polyethylene waxes having a molecular weight of from 150 to 1000 g/mol by telomerization of ethylene with aldehydes at from 500 to 5000 bar and from 100 to 280.degree. C., wherein ethylene and aldehyde are employed in a molar ration of from 5:1 to 50:1.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: August 3, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Deckers, Eckard Schauss
  • Patent number: 5874636
    Abstract: The present invention relates to a process for the preparation of terpenic ketones, which comprises reacting a 1,3-butadiene derivative with a .beta.-keto ester followed by decarbalkoxylation of the product.
    Type: Grant
    Filed: April 6, 1992
    Date of Patent: February 23, 1999
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Pierre Chabardes, Claude Mercier
  • Patent number: 5723678
    Abstract: Acetylenic compounds of the general formula IR.sup.1 --C.tbd.C--CHR.sup.2 --CH.sub.2 --X Iwhere the substituents have the following meanings:R.sup.1 hydrogen, unsubstituted or substituted alkyl or aryl;R.sup.2 hydrogen or C.sub.1 -C.sub.4 -alkyl;X CN; COOR.sup.3 where R.sup.3 is C.sub.1 -C.sub.6 -alkyl or benzyl; C(O)R.sup.4 where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,are prepared by reacting an alkyne of the formula IIR.sup.1 --C.tbd.C--H IIwith an .alpha.,.beta.-unsaturated compound of the formula IIIR.sup.2 HC.dbd.CH--X IIIin the presence of a homogeneous rhodium-phosphine catalyst, in a process wherein a catalyst with a bidentate or tridentate phosphine compound is used.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Peter Hofmann
  • Patent number: 5527968
    Abstract: A hydroxy-terminated linear carbonate is produced by reacting a cyclic alkylene carbonate such as neopentyl glycol carbonate with a substance having at least one alcoholic hydroxyl group in the presence of a catalyst. Mono- or polyhydric alphatic alcohols, polycaprolactone polyols, hydroxyl group-containing acrylic monomers and polymers, and polyester polyols are modified by the reaction with the cyclic alkylene carbonate to have an enhanced reactivity and resistance to hydrolysis.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: June 18, 1996
    Assignees: Nipon Paint Co., Ltd., Daicel Chemical Industries, Ltd.
    Inventors: Shinji Nakano, Takao Morimoto, Shin-ya Yamada, Takaaki Fujiwa, Hideki Matsui, Takeharu Tabuchi
  • Patent number: 5434289
    Abstract: A process for producing an optically active .beta.-hydroxyketone represented by formula (I): ##STR1## by catalytic asymmetrical aldol reaction is disclosed, comprising reacting a silyl-enol ether represented by formula (II): ##STR2## with a substituted aldehyde represented by formula (III):R.sup.5 CHO (III)in the presence of a binaphthol-titanium complex represented by formula (IV): ##STR3## An optically active .beta.-hydroxyketone is efficiently produced with diastereo-specificity and enantio-specificity.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: July 18, 1995
    Assignee: Takasago International Corporation
    Inventors: Koichi Mikami, Satoru Matsukawa, Masaki Shimizu, Masahiro Terada, Noboru Sayo
  • Patent number: 5414163
    Abstract: A method for preparing tertiary butyl alcohol wherein a feedstock comprising a solvent solution of tertiary butyl hydroperoxide in tertiary butyl alcohol or a mixture of tertiary butyl alcohol with isobutane is charged to a hydroperoxide decomposition reaction zone containing a catalytically effective amount of a hydroperoxide decomposition catalyst consisting essentially of titania or zirconia and is brought into contact with the catalyst in liquid phase under hydroperoxide decomposition reaction conditions to convert the tertiary butyl hydroperoxide to decomposition products, principally tertiary butyl alcohol.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: May 9, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: John R. Sanderson, John F. Knifton, Edward T. Marquis
  • Patent number: 5202460
    Abstract: Terpene derivatives of formula I, their preparation and their use. In formula I, R represents a hydrogen atom or an alkanoyl radical and R' represents a hydrogen atom or an aliphatic hydrocarbon radical.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: April 13, 1993
    Assignee: Rhone Poulenc Sante
    Inventor: Claude Mercier
  • Patent number: 4621165
    Abstract: A process for removing from a mixture of isoprene trimers compounds of the formula ##STR1## by reacting a mixture of cyclic and linear trimers with a compound having an activated carbon atom, of the formula:X--CH.sub.2 --Yin which one of X or Y is an electron-withdrawing group and the other is an electron-withdrawing or electron-donating group, in the presence of a catalyst consisting of a water-soluble phosphine and a rhodium compound, the reaction being carried out in water or in a water-alcohol medium, and separating the cyclic trimers and linear trimers containing the chain ##STR2## from the mixture of products of the formulae: ##STR3## which can be used, in particular, in the synthesis of vitamin E.
    Type: Grant
    Filed: February 23, 1984
    Date of Patent: November 4, 1986
    Assignee: Rhone-Poulenc Sante
    Inventor: Didier Morel
  • Patent number: 4556741
    Abstract: This invention relates to a process for dismuting functionalized olefins using a catalyst which has rhenium heptoxide on phosphated alumina and a metal hydrocarbon compound such as an alkyl tin. The olefins that may be dismuted are those which have a hetero atom such as oxygen, nitrogen or halide in the chain. Specific examples are olefinic compounds which have an ester, ether or a ketone group. The products of the reaction are useful chemical intermediates.
    Type: Grant
    Filed: November 28, 1983
    Date of Patent: December 3, 1985
    Assignee: BP Chemicals Limited
    Inventor: Malcolm J. Lawrenson
  • Patent number: 4460786
    Abstract: The selective addition of a compound having an activated carbon atom onto the carbon atom in the 4-position of a buta-1,3-diene carrying a hydrocarbon substituent on the carbon atom in the 2-position is achieved by reacting the compound having the activated carbon atom with the buta-1,3-diene carrying the hydrocarbon substituent in water or in an aqueous-alcoholic mixture in the presence of a catalyst which consists of at least one water-soluble phosphine and at least one rhodium compound, the catalyst being in solution in the water or aqueous alcoholic mixture. The products obtained are useful as precursors of intermediates for the synthesis of vitamins and perfumes.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: July 17, 1984
    Assignee: Rhone-Poulenc Industries
    Inventor: Didier Morel
  • Patent number: 4357282
    Abstract: Fluorinated carbonyl compounds are prepared by contacting a fluorinated methyl or ethyl ether containing at least one methoxylated carbon atom-containing group selected from: --CF.sub.2 OR.sup.3, .dbd.CFOR.sup.3, ##STR1## wherein R.sup.3 is CH.sub.3 or C.sub.2 H.sub.5, with a catalyst selected from:SbX.sub.5, TaX.sub.5, NbX.sub.5, AsX.sub.5, BiX.sub.5, TiX.sub.4, ZrX.sub.4, HfX.sub.4, FeX.sub.3,mixtures of SbX.sub.3 and SbX.sub.5, ZM'X'.sub.6, and mixtures of ZM'X'.sub.6 and M'X.sub.5 where X, independently, is F, Cl, Br or I, X' is F or Cl; and Z is H, NO, O.sub.2, alkali metal or NY.sub.4 where Y, independently, is H or alkyl of 1 to 6 carbon atoms, and M' is Sb or As at a temperature of -20.degree. to 200.degree. C.
    Type: Grant
    Filed: April 3, 1981
    Date of Patent: November 2, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Daniel G. Anderson, David C. England, Alwin S. Milian, Jr.
  • Patent number: 4322561
    Abstract: For preparing carbonyl compounds containing certain functional groups, a carbonyl compound is reacted with an unsaturated compound in the presence of a trivalent-manganese initiator and an amine. There is a positive coaction between the trivalent-Mn catalyst and the amine. Typically, 2-methyl-3-butene-2-ol is reacted with acetone in the presence of triethylamine and manganese triacetate (bihydrated) to obtain 2-methyl-heptane-2-ol-3-one. Yields and selectivities are more than satisfactory.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: March 30, 1982
    Assignee: Anio S.p.A.
    Inventors: Lucio Faggian, Edoardo Platone
  • Patent number: 4260750
    Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.
    Type: Grant
    Filed: March 13, 1980
    Date of Patent: April 7, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Emile Kuntz