Carbon To Carbon Unsaturation In The Reactant Patents (Class 568/398)
  • Patent number: 8304581
    Abstract: The present invention relates to a method of enantioselective addition to enones, including: reacting R3(CH2)pCH?CR5C(?O)Y(CH2)qR4 with R6ZnR7 in the presence of a compound represented by the following formula (I) and a transition metal catalyst, in which Y, p, q, R1, R2, R3, R4, R5, R6 and R7 are defined the same as the specification. Accordingly, the present invention can perform asymmetric conjugate addition in high yields and enantioselectivity.
    Type: Grant
    Filed: July 19, 2010
    Date of Patent: November 6, 2012
    Assignee: National Tsing Hua University
    Inventors: Biing-Jiun Uang, Chih-Hao Tseng
  • Patent number: 8003827
    Abstract: A method for producing phenol and acetone in a multi-stage process at an elevated temperature from a cumene hydroperoxide mixture comprising cumene, comprises the steps of: a) distilling an amount of cumene from the cumene hydroperoxide mixture until the cumene mass % is 0 to 7 mass % relative to the total mass of the cumene hydroperoxide mixture, b) reacting the cumene hydroperoxide mixture with an acid catalyst form to a second mixture comprising phenol, acetone and dicumyl peroxide in a first stage, and c) decomposing the second mixture in a second stage to produce phenol and acetone, wherein an amount of phenol approximately equal to the amount of distilled from the cumene hydroperoxide mixture is added to the cumene hydroperoxide mixture before the reacting step b). The amount of hydroxyacetone is reduced, thereby, improving the quality of commercial-grade phenol and the products made from the phenol.
    Type: Grant
    Filed: April 15, 2009
    Date of Patent: August 23, 2011
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Mark E. Nelson, Arkady Samuilovich Dykman, Andrey Vladimirovich Zinenkov, Victor Vladimirovich Pinson, Ilja Nikolayevich Grebenshchikov
  • Patent number: 7932418
    Abstract: The present invention relates to a preparation of ?-? ene carboxylic or ketone derivatives, which may also have particular requirement on the configuration of the carbon-carbon double bond. The method requires a thermal treatment of ?-? unsaturated malonate or acetylacetonate derivatives in the presents of at least one carboxylic acid and at least one alkaline, alkaline-earth or lanthanide halide or carboxylates.
    Type: Grant
    Filed: February 1, 2007
    Date of Patent: April 26, 2011
    Assignee: Firmenich SA
    Inventors: Hubert Mimoun, Serge Bonnaudet
  • Patent number: 7462745
    Abstract: Process for preparing 1-octa-2,7-dienyl derivatives by reacting a 1,3-butadiene-containing hydrocarbon mixture, in particular a C4 fraction from a cracker, with nucleophiles, in which acetylenically unsaturated compounds are removed from the starting hydrocarbon mixture by selective hydrogenation and a telomerization is subsequently carried out.
    Type: Grant
    Filed: August 23, 2005
    Date of Patent: December 9, 2008
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Franz Nierlich, Cornelia Borgmann, Dirk Roettger, Stephan Houbrechts, Dietrich Maschmeyer
  • Patent number: 7399879
    Abstract: A process for the preparation of a monoalkylidene substituted 1,4-dions derivatives of formula (Ia) or (Ib) or a mixture of (Ia) and (Ib): wherein: R1, R2 and R3, equal to or different from each other, are hydrogen atoms or C1–C20 hydrocarbon groups: T1 and T2, equal to or different from each other, are OR4, R4, NR42, SR4 or PR42; or T1 and T2 can be fused in an oxygen atom or a NR4 group; said process comprises the step of reacting a compound of formula (II) with a compound of formula (IIIa) or (IIIb) in the presence of at least one equivalent with respect to the compound of formula (IIIa) or (IIIb) of a carbonate of metal M or of a compound of formula MTj such as K2CO3 or KHCO3
    Type: Grant
    Filed: July 25, 2003
    Date of Patent: July 15, 2008
    Assignee: Basell Poliolefine Italia S.p.A.
    Inventors: Yuri V. Gulevich, Giampiero Morini
  • Patent number: 7345205
    Abstract: A process is described for preparing tetrahydrogeranylacetone in which pseudoionone, geranylacetone and/or dihydrogeranylacetone in a liquid phase, in which particles of a catalyst which is capable of preferentially hydrogenating carbon-carbon double bonds over carbon-oxygen double bonds are suspended, is conducted through a device which inhibits the transport of the catalyst particles in the presence of a hydrogen-containing gas.
    Type: Grant
    Filed: July 14, 2003
    Date of Patent: March 18, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Georg Goebbel, Gerd Kaibel, Christian Miller, Walter Dobler, Thomas Dirnsteiner, Thilo Hahn, Klaus Breuer, Werner Aquila
  • Patent number: 7291755
    Abstract: The present invention relates to a method for producing an alcohol and/or a ketone from a corresponding alkene(s) in a gas phase in the presence of water vapor by the use of an oxide catalyst. According to the present invention, there is provided a method for producing an alcohol and/or a ketone by bringing a starting material containing an alkene(s), as a gas phase into contact with an oxide catalyst in the presence of water vapor to carry out the reaction, wherein the oxide catalyst satisfies the following requirements: (a) it comprises an oxide(s) of molybdenum and/or tin, and (b) the amount of carbonaceous substances accumulated on the oxide catalyst is controlled to be within a range of 0.1 to 10% by mass, during the reaction.
    Type: Grant
    Filed: December 25, 2003
    Date of Patent: November 6, 2007
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Takashi Tsunoda, Kenji Akagishi, Atusi Watanabe
  • Patent number: 7285685
    Abstract: Process for preparing alpha, beta-unsaturated acyclic or cyclic carbonyl compounds by dehydrogenation of the corresponding saturated carbonyl compounds in the gas phase over a heterogeneous dehydrogenation catalyst comprising platinum and/or palladium and tin on an oxidic support.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: October 23, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Christian Walsdorff, Beatrice Rössler, Götz-Peter Schindler, Joaquim H. Teles, Klaus Harth
  • Patent number: 7235698
    Abstract: Compounds containing a substituted or unsubstituted allyl group directly bound to a chiral carbon atom are prepared enantioselectively. Starting reactants are either chiral or achiral, and may or may not contain an attached allyloxycarbonyl group as a substituent. Chiral ligands are employed, along with transition metal catalysts. The methods of the invention are effective in providing enantioconvergent allylation of chiral molecules.
    Type: Grant
    Filed: August 29, 2005
    Date of Patent: June 26, 2007
    Assignee: California Institute of Technology
    Inventors: Douglas C. Behenna, Brian M. Stoltz, Justin T. Mohr, Andrew M. Harned
  • Patent number: 6987203
    Abstract: A process for the preparation of a novel intermediate compound useful in the preparation of phytone and vitamin E.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: January 17, 2006
    Assignee: Adisseo France S.A.S.
    Inventor: Jean-Erick Ancel
  • Patent number: 6818796
    Abstract: A subject of the present invention is a process for preparation of fluorinated ketones corresponding to general formula (I) R1—CO—R2 in which R1 and R2 are as defined in claim 1, characterized in that it consists of reacting two carboxylic acids of Formula (II), R1—COOH and Formula (III), R2—COOH, in the gaseous phase and in the presence of a catalyst comprising at least one oxide of an element chosen from the rare earths, thorium, titanium and aluminum.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: November 16, 2004
    Assignee: Rhodia Chimie
    Inventor: Roland Jacquot
  • Patent number: 6787671
    Abstract: An osmium-assisted process for the oxidative cleavage of oxidizable organic compounds such as unsaturated organic compounds, including alkenes and olefins into aldehydes, carboxylic acids, esters, or ketones. The process uses a metal catalyst comprising osmium and a peroxy compound selected from the group consisting of peroxymonosulfuric acid and salts thereof to oxidatively cleave the oxidizable organic compound. In particular, the process enables aldehydes, carboxylic acids, esters, or ketones to be selectively produced from the corresponding mono-, 1,1-di-, 1,2-di-, tri-, or tetra-substituted olefins in a reaction that produces the result of ozonolysis but with fewer problems. The present invention further provides a process for oxidizing an aldehyde alone or with the osmium in an interactive solvent to produce an ester or carboxylic acid.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: September 7, 2004
    Assignee: Board of Trustees of Michigan State University
    Inventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
  • Patent number: 6689918
    Abstract: A method for producing &agr;-dicarbonyl compounds of formula (I): wherein R1 and R2, independently of each other, mean C1-6-alkyl. In the method, an &agr;,&bgr;-unsaturated ketone of formula (II): wherein R1 and R2 have the meaning above and R3 and R4, independently of each other, mean hydrogen, C1-6-alkyl or di-C1-6-alkylamino, is reacted with ozone in the absence of a catalyst and the resultant ozonide is treated reductively.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: February 10, 2004
    Assignee: Lonza AG
    Inventors: Uta Glufke, Paul Hanselmann
  • Patent number: 6310259
    Abstract: The present application refers to a process for preparing 6,10- and 6,9-dimethyl-5,10-undecadienyl-2-ones by telomerizing isoprene with alkyl acetoacetates in the presence of a catalyst system containing a transition metal compound catalyst and a phosphorus- or arsenic-containing compound cocatalyst, wherein the process is performed in the presence of a protic additive of the general formula in which: R1, R2, R3 represent an alkyl group with 1 to 9 carbon atoms, branched or unbranched, a cycloalkyl group with 6 to 8 carbon atoms, an aryl group, in particular phenyl, or an arylalkyl group, X(−) represents an inorganic or organic anion, y is 1 or 2, and the &bgr;-ketoester so obtained is saponified and decarboxylated in a manner known per se.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: October 30, 2001
    Assignee: Degussa AG
    Inventors: Wilhelm Keim, Armin Kraus, Rainer Hahn, Klaus Huthmacher
  • Patent number: 6307106
    Abstract: An improved process for preparing lower unsaturated ketones by reacting the corresponding &agr;,&bgr;-unsaturated alcohols with alkyl acetoacetates in a Carroll reaction in the presence of from 0.1 to 5 mol %, based on the alkyl acetoacetate to be reacted, of an organic aluminum compound as catalyst with elimination and continuous removal by distillation of the alkanol eliminated during the reaction from the alkyl acetoacetate in a reactor system with a fitted fractionation column, wherein A an &agr;,&bgr;-unsaturated alcohol which boils below 140° C. is introduced, in the absence of effective amounts of a solvent, together with the organic aluminum compound into the reaction vessel, B a reaction temperature which is as constant as possible between 170° C. and 250° C.
    Type: Grant
    Filed: November 15, 1999
    Date of Patent: October 23, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Carsten Oost, Manfred Stroezel, Heinz Etzrodt, Dietmar Weller, Gerd Kaibel, Hagen Jaedicke
  • Patent number: 6051741
    Abstract: A process for preparing .gamma.,.delta.-unsaturated ketones of the general formula I ##STR1## by reacting an allyl alcohol of the general formula II ##STR2## in which R.sup.1 is H or a hydrocarbon radical having 1 to 20 carbon atoms, with diketene or an alkyl acetoacetate of the general formula III ##STR3## in which R.sup.2 is alkyl having 1 to 4 carbon atoms in an unmodified or modified Carroll reaction in the presence of an aluminum catalyst, wherein aluminum compounds which are stable liquids at room temperature, or a mixture of such aluminum compounds, which comprise at least one radical formed from an alkyl acetoacetate and 1 or 2 alkoxy radicals, or else comprise exclusively radicals formed from alkyl acetoacetates, which are esterified with sec-butanol or isobutanol, or else are esterified with at least two different alcohols, are used as aluminum catalyst.
    Type: Grant
    Filed: October 8, 1998
    Date of Patent: April 18, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Etzrodt, Dietmar Weller, Carsten Oost, Hagen Jaedicke, Manfred Stroezel, Bernhard Bockstiegel, Lothar Laupichler, Klaus Reimer
  • Patent number: 6031139
    Abstract: The use of polar organic solvent as the solvent in the direct fluorination, to make an .alpha.-fluoroketone, of an enol ester or enol trialkylsilyl ether of a compound containing a tautomerisable ketone group, the solvent being relatively inert to fluorine and one in which the enol ester or enol trialkylsilyl ether is relatively stable to hydrolysis. Preferably the solvent is anhydrous, e.g. anhydrous acetonitrile. Alternatively commercial formic acid containing 3% water may be used with a said enol ester.
    Type: Grant
    Filed: February 5, 1998
    Date of Patent: February 29, 2000
    Assignee: F2 Chemicals Limited
    Inventors: John Hutchinson, Richard Dickinson Chambers
  • Patent number: 6018060
    Abstract: A process and apparatus for manufacture of organic products, particularly chemical intermediates, by oxidation of organic feedstocks. A membrane unit containing a membrane selectively permeable to the organic over argon is used to recover the feedstock from the argon purge stream.
    Type: Grant
    Filed: October 5, 1998
    Date of Patent: January 25, 2000
    Assignee: Membrane Technology and Research, Inc.
    Inventors: Richard W. Baker, Douglas Gottschlich
  • Patent number: 5874635
    Abstract: A process for preparing .gamma.,.delta.-unsaturated ketones bya) reacting vinylcarbinols or propargyl alcohols with alkyl acetoacetates or diketene andb) thermally rearranging the resulting acetoacetates in the presence or absence of an aluminum catalyst to .gamma.,.delta.-unsaturated ketones (Carroll reaction),wherein step a) and/or step b) is carried out in a cyclic carbonate of the formula I or a .gamma.-lactone of the formula II ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are H, or lower alkyl and R.sup.4 is H, lower alkyl, phenyl or methoxymethyl, as solvent.
    Type: Grant
    Filed: November 5, 1997
    Date of Patent: February 23, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Etzrodt, Manfred Stroezel, Dietmar Weller, Hagen Jaedicke
  • Patent number: 5852200
    Abstract: Cross-coupling or addition reactions of organic compounds, including acid halides, allylic halides, and .alpha.,.beta.-unsaturated carbonyl containing compounds, with organozinc compounds may be readily and safely carried out in the presence of cuprous iodide. The use of this catalyst in the coupling reaction provides for the preparation of commercially useful products in the pharmaceutical, agrochemical and other industries.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: December 22, 1998
    Assignee: Rieke Metals, Inc.
    Inventor: Reuben D. Rieke
  • Patent number: 5744071
    Abstract: The present invention provides processes for making alkynyl ketones and precursors thereof, using less expensive reagents and/or hydrocarbon solvents and/or higher temperatures.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: April 28, 1998
    Assignee: FMC Corporation
    Inventors: Philip Franklin Sims, Anne Pautard-Cooper
  • Patent number: 5118862
    Abstract: Disclosed is a process for producing an .alpha.,.beta.-unsaturated carbonyl compound represented by the formula [II]: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents a hydrogen atom or a hydrocarbon residue and may be linear or may form a ring in optional combination thereof and total carbon atom number of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 12 or less, which comprises contacting oxygen with an alkenyl compound represented by the formula [I]: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above and X represents a trihydrocarbylsilyl group or an acyl group in the presence of a platinum group metal-supporting catalyst.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: June 2, 1992
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Toshihide Baba, Mitsuo Masai
  • Patent number: 5118863
    Abstract: A process for producing an .alpha.,.beta.-unsaturated carbonyl compound represented by formula (II): ##STR1## which includes subjecting an alkenyl ester represented by formula (I): ##STR2## and an allyl type carbonic ester to catalytic reaction in the presence of a platinum group metal compound catalyst without the necessity of an organotin alkoxide. The subsequent addition of a phosphorus-containing compound, followed by heating, results in the decomposition and removal of unreacted allyl type carbonic ester and reaction by-product.
    Type: Grant
    Filed: September 5, 1991
    Date of Patent: June 2, 1992
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Kiyoshi Watanabe, Rikitaro Matsuoka
  • Patent number: 5021178
    Abstract: Oligomers produced from lower alkenes by acidic zeolite catalyzed oligomerization can be converted to useful lubricant additives or lubricants by acylation of olefinic bonds in the oligomers, whereby oligomers containing alpha, beta unsaturated ketone structures are produced. The products so produced from C.sub.20 + olefins exhibit favorable lubricant qualities of viscosity index and low pour points. The discovery is particularly applicable to the acylation of oligomers produced from lower alkenes such as propylene by oligomerization using a ZSM-5 catalyst which has been surface deactivated.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: June 4, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Catherine S. H. Chen, Paul G. Rodewald
  • Patent number: 4900871
    Abstract: Hydrocarbons, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidized with air or O.sub.2 to form such products as alcohols, ketones, and the like selectively high yields when there is employed as the catalyst a coordination complex containing an iron center and a halogenated ligand having the structure ##STR1## where Fe is iron; " .circle. " is a ligand; X is a halogen substituent of the ligand; and A is an anion.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: February 13, 1990
    Assignee: Sun Refining and Marketing Company
    Inventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
  • Patent number: 4450288
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with an alkyl pyridinium salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Timm E. Paxson
  • Patent number: 4450286
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with a quaternary ammonium and/or phosphonium substituted ferrocenyl salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Timm E. Paxson
  • Patent number: 4450287
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with a quaternary ammonium salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Timm E. Paxson
  • Patent number: 4450289
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with a quaternary phosphonium salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Paxson, Timm E.
  • Patent number: 4385187
    Abstract: Perfluoroketovinyl ether of the formula (as in claim 1) wherein n is an integer 1 to 4, copolymers of such ether and a fluorinated monomer, such as tetrafluoroethylene; ion-exchange resins of such copolymers; and ion-exchange membranes of such resins.
    Type: Grant
    Filed: June 30, 1981
    Date of Patent: May 24, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ronald E. Uschold
  • Patent number: 4374276
    Abstract: Described are acylated derivatives of triisobutylene defined according to the generic structures: ##STR1## wherein, in each of the molecules one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represents a carbon-carbon single bond; and wherein, in each of the molecules R.sub.3 represents methyl or ethyl; uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g.
    Type: Grant
    Filed: August 27, 1981
    Date of Patent: February 15, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Theodore J. Tyszkiewicz
  • Patent number: 4346237
    Abstract: Described are branched ketones defined according to the generic structure: ##STR1## wherein R.sub.4 ' represents C.sub.1 -C.sub.4 lower alkyl; wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds. Also described are organoleptic uses of these branched ketones in augmenting or enhancing the aroma or taste of consumable materials such as perfume compositions, colognes, perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents; cosmetic powders; hair preparations; fabric softener compositions and dryer-added fabric softener articles), foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos and smoking tobacco articles as well as processes for preparing such branched ketones by reacting dimers of isoamylene with acyl halides or acyl anhydrides or mixed acyl anhydrides.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: August 24, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Richard M. Boden
  • Patent number: 4310705
    Abstract: An improved process for the preparation of higher unsaturated ketones, such as geranylacetone and farnesylacetone, by reacting a .beta.,.gamma.-unsaturated alcohol and an alkyl acetoacetate at an elevated temperature in the presence of an organic aluminum compound, with elimination, and removal, of the alcohol derived from the alkyl acetoacetate in a reactor system carrying a fractionating column. The improvement in the purity, yield, and especially space-time yield of the product is achieved by starting from an alcohol having a higher boiling point than that of the alkyl acetoacetate used, carrying out the reaction in the presence of a small amount of an inert liquid which has a boiling point between that of the alkyl acetoacetate and the alcohol to be eliminated therefrom, and ensuring that the temperature at the bottom of the fractionating column is only slightly higher than the boiling point of the added liquid, under the prevailing pressure.
    Type: Grant
    Filed: June 26, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Axel Nissen, Gerd Kaibel, Otto Woerz, Lothar Arnold, Manfred Braun, Walter Rebafka
  • Patent number: 4245122
    Abstract: A process is described for the preparation of allyl acetone (5-hexen-2-one) according to the reaction: ##STR1## wherein R is methyl or ethyl; X is chloro or bromo; M is sodium or potassium; and Q is sodium or potassium, the reaction being carried out (i) using a phase transfer agent and (ii) in a two phase system.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: January 13, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, Denis E. Hruza, Sr., John B. Hall
  • 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