Carbon To Carbon Unsaturation In The Reactant Patents (Class 568/398)
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Patent number: 8304581Abstract: 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: GrantFiled: July 19, 2010Date of Patent: November 6, 2012Assignee: National Tsing Hua UniversityInventors: Biing-Jiun Uang, Chih-Hao Tseng
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Patent number: 8003827Abstract: 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: GrantFiled: April 15, 2009Date of Patent: August 23, 2011Assignee: Sabic Innovative Plastics IP B.V.Inventors: Mark E. Nelson, Arkady Samuilovich Dykman, Andrey Vladimirovich Zinenkov, Victor Vladimirovich Pinson, Ilja Nikolayevich Grebenshchikov
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Patent number: 7932418Abstract: 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: GrantFiled: February 1, 2007Date of Patent: April 26, 2011Assignee: Firmenich SAInventors: Hubert Mimoun, Serge Bonnaudet
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Patent number: 7462745Abstract: 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: GrantFiled: August 23, 2005Date of Patent: December 9, 2008Assignee: OXENO Olefinchemie GmbHInventors: Franz Nierlich, Cornelia Borgmann, Dirk Roettger, Stephan Houbrechts, Dietrich Maschmeyer
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Patent number: 7399879Abstract: 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 KHCO3Type: GrantFiled: July 25, 2003Date of Patent: July 15, 2008Assignee: Basell Poliolefine Italia S.p.A.Inventors: Yuri V. Gulevich, Giampiero Morini
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Patent number: 7345205Abstract: 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: GrantFiled: July 14, 2003Date of Patent: March 18, 2008Assignee: BASF AktiengesellschaftInventors: Hans-Georg Goebbel, Gerd Kaibel, Christian Miller, Walter Dobler, Thomas Dirnsteiner, Thilo Hahn, Klaus Breuer, Werner Aquila
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Patent number: 7291755Abstract: 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: GrantFiled: December 25, 2003Date of Patent: November 6, 2007Assignee: Asahi Kasei Chemicals CorporationInventors: Takashi Tsunoda, Kenji Akagishi, Atusi Watanabe
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Patent number: 7285685Abstract: 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: GrantFiled: July 22, 2004Date of Patent: October 23, 2007Assignee: BASF AktiengesellschaftInventors: Christian Walsdorff, Beatrice Rössler, Götz-Peter Schindler, Joaquim H. Teles, Klaus Harth
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Patent number: 7235698Abstract: 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: GrantFiled: August 29, 2005Date of Patent: June 26, 2007Assignee: California Institute of TechnologyInventors: Douglas C. Behenna, Brian M. Stoltz, Justin T. Mohr, Andrew M. Harned
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Patent number: 6987203Abstract: A process for the preparation of a novel intermediate compound useful in the preparation of phytone and vitamin E.Type: GrantFiled: January 13, 2003Date of Patent: January 17, 2006Assignee: Adisseo France S.A.S.Inventor: Jean-Erick Ancel
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Patent number: 6818796Abstract: 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: GrantFiled: September 26, 2003Date of Patent: November 16, 2004Assignee: Rhodia ChimieInventor: Roland Jacquot
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Patent number: 6787671Abstract: 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: GrantFiled: January 13, 2003Date of Patent: September 7, 2004Assignee: Board of Trustees of Michigan State UniversityInventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
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Patent number: 6689918Abstract: 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: GrantFiled: November 19, 2002Date of Patent: February 10, 2004Assignee: Lonza AGInventors: Uta Glufke, Paul Hanselmann
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Patent number: 6310259Abstract: 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: GrantFiled: March 23, 2000Date of Patent: October 30, 2001Assignee: Degussa AGInventors: Wilhelm Keim, Armin Kraus, Rainer Hahn, Klaus Huthmacher
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Patent number: 6307106Abstract: 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: GrantFiled: November 15, 1999Date of Patent: October 23, 2001Assignee: BASF AktiengesellschaftInventors: Carsten Oost, Manfred Stroezel, Heinz Etzrodt, Dietmar Weller, Gerd Kaibel, Hagen Jaedicke
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Patent number: 6051741Abstract: 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: GrantFiled: October 8, 1998Date of Patent: April 18, 2000Assignee: BASF AktiengesellschaftInventors: Heinz Etzrodt, Dietmar Weller, Carsten Oost, Hagen Jaedicke, Manfred Stroezel, Bernhard Bockstiegel, Lothar Laupichler, Klaus Reimer
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Patent number: 6031139Abstract: 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: GrantFiled: February 5, 1998Date of Patent: February 29, 2000Assignee: F2 Chemicals LimitedInventors: John Hutchinson, Richard Dickinson Chambers
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Patent number: 6018060Abstract: 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: GrantFiled: October 5, 1998Date of Patent: January 25, 2000Assignee: Membrane Technology and Research, Inc.Inventors: Richard W. Baker, Douglas Gottschlich
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Patent number: 5874635Abstract: 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: GrantFiled: November 5, 1997Date of Patent: February 23, 1999Assignee: BASF AktiengesellschaftInventors: Heinz Etzrodt, Manfred Stroezel, Dietmar Weller, Hagen Jaedicke
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Patent number: 5852200Abstract: 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: GrantFiled: August 22, 1996Date of Patent: December 22, 1998Assignee: Rieke Metals, Inc.Inventor: Reuben D. Rieke
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Patent number: 5744071Abstract: 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: GrantFiled: November 19, 1996Date of Patent: April 28, 1998Assignee: FMC CorporationInventors: Philip Franklin Sims, Anne Pautard-Cooper
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Patent number: 5118862Abstract: 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: GrantFiled: August 27, 1990Date of Patent: June 2, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Toshihide Baba, Mitsuo Masai
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Patent number: 5118863Abstract: 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: GrantFiled: September 5, 1991Date of Patent: June 2, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Kiyoshi Watanabe, Rikitaro Matsuoka
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Patent number: 5021178Abstract: 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: GrantFiled: February 7, 1990Date of Patent: June 4, 1991Assignee: Mobil Oil CorporationInventors: Catherine S. H. Chen, Paul G. Rodewald
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Patent number: 4900871Abstract: 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: GrantFiled: June 26, 1987Date of Patent: February 13, 1990Assignee: Sun Refining and Marketing CompanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4450289Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Paxson, Timm E.
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Patent number: 4450286Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Timm E. Paxson
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Patent number: 4450288Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Timm E. Paxson
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Patent number: 4450287Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Timm E. Paxson
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Patent number: 4385187Abstract: 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: GrantFiled: June 30, 1981Date of Patent: May 24, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald E. Uschold
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Patent number: 4374276Abstract: 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: GrantFiled: August 27, 1981Date of Patent: February 15, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Theodore J. Tyszkiewicz
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Patent number: 4346237Abstract: 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: GrantFiled: May 8, 1981Date of Patent: August 24, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4310705Abstract: 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: GrantFiled: June 26, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventors: Axel Nissen, Gerd Kaibel, Otto Woerz, Lothar Arnold, Manfred Braun, Walter Rebafka
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Patent number: 4245122Abstract: 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: GrantFiled: December 5, 1979Date of Patent: January 13, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, Denis E. Hruza, Sr., John B. Hall
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner