Aldehyde Or Ketone Reactant Patents (Class 568/388)
  • Publication number: 20040249219
    Abstract: The invention is directed to an efficient and economical method of making teprenone. Teprenone is synthesized by converting geranylgeraniol to teprenone by a novel route. The method of synthesis can begin with geranylgeraniol obtained from a biological source such as fermentation of a microorganism capable of producing geranylgeranyl or enzymatic synthesis in a cell free system to produce predominantly the 5E isomer of teprenone. The chemical synthesis proceeds with retention of configuration such that the teprenone produced has the isomeric configuration of the geranylgeraniol starting material.
    Type: Application
    Filed: July 3, 2001
    Publication date: December 9, 2004
    Inventor: Gabriel G. Saucy
  • Publication number: 20040249218
    Abstract: Process for preparing 6-methylheptan-2-one, which comprises
    Type: Application
    Filed: March 24, 2004
    Publication date: December 9, 2004
    Inventors: Klaus-Diether Wiese, Guido Protzmann
  • Publication number: 20040204610
    Abstract: A zeolite-immobilised Lewis acid e.g. copper catalyst for performing carbonyl-ene and iminoene reactions is described. The catalyst can readily be separated from the reaction mixture and re-used in further reactions with minimal reduction in activity.
    Type: Application
    Filed: May 26, 2004
    Publication date: October 14, 2004
    Inventors: Frederick Ernest Hancock, Graham John Hutchings, Neil Aubrey Caplan
  • Patent number: 6780812
    Abstract: A novel chiral lead catalyst comprising a lead compound of the following formula: Pb(ORf)2 (wherein Rf represents a fluorine-containing alkylsulfonyl group) and a chiral crown ether compound having the structure of the following formula: which is applicable in a variety of reactions, and enables simple reaction operations with high yield and high optical selectivity, is provided. Also provided is a method of asymmetric synthesis using the same.
    Type: Grant
    Filed: December 11, 2001
    Date of Patent: August 24, 2004
    Assignee: Japan Science and Technology Corporation
    Inventor: Shu Kobayashi
  • Publication number: 20040082818
    Abstract: The invention relates to a process for the preparation, in a single step, of enones by an aldol condensation of a ketone, such as a gem-dimethyl cyclohexylethanone or gemdimethyl cyclohexenylethanone derivative, with an aldehyde in the presence of a novel catalytic system and a co-ingredient, such as a carboxylic acid anhydride or an anhydrous salt, and without the pre-formation of an enolate. The catalytic system is a metal complex, such as a [(Cl)n(alkoxy)4−nTi] or [(Cl)n(alkoxy)4−nZr] complex where n is 1 to 3.
    Type: Application
    Filed: October 17, 2003
    Publication date: April 29, 2004
    Inventor: Denis Jacoby
  • Patent number: 6706928
    Abstract: Production of unsaturated ketones by the aldol condensation of ketones such as acetone or methyl ethyl ketone by contacting the ketone in the vapor phase with a particulate catalyst comprising at least one basic alkali metal compound supported on an inert substrate at a temperature above 175° C. The produce ketones may be hydrogenated to form saturated ketones or alcohols.
    Type: Grant
    Filed: November 18, 2002
    Date of Patent: March 16, 2004
    Assignee: Johnson Matthey PLC
    Inventor: Gordon J Kelly
  • Publication number: 20040039234
    Abstract: A method for the synthesis of an &agr;,&bgr;-unsaturated ketone useful for making substituted 1,4-dihydropyridines is described by reacting an aldehyde with pyrrolidine and then adding a ketone followed by trifluoroacetic acid at low temperature. The synthesis is used in a process for making substituted 1,4-dihydropyridines wherein a vinylogous amide is prepared by reacting a 1,3-cyclohexanedione with a phenylethylamine. The &agr;,&bgr;-unsaturated ketone can be reacted with a vinylogous amide to form a 1,5-diketone which can be converted to a substituted 1,4-dihydropyridine.
    Type: Application
    Filed: September 5, 2003
    Publication date: February 26, 2004
    Inventors: Ian Patel, Philip Hopes
  • Publication number: 20040034254
    Abstract: The invention relates to a process for producing 1,1,1-trifluoroacetone, which is useful as an intermediate of pharmaceuticals and agricultural chemicals, or as a reagent for introducing fluorine-containing groups.
    Type: Application
    Filed: May 30, 2003
    Publication date: February 19, 2004
    Applicant: Central Glass Company, Limited
    Inventors: Masanori Tsukamoto, Fumiyoshi Yoshikawa, Masataka Fujimoto, Naoto Takada, Yoshikazu Sugimori, Junji Negishi
  • 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
  • Publication number: 20040006171
    Abstract: Metal salts of organic acids complexed with &bgr;-diketone compounds are multifunctional complexes useful in the formulation of stabilizers for halogenated resins. These complexes may be used jointly with other low toxicity intermediates, such as zinc or magnesium intermediates, to form effective stabilizers that are non-toxic and exhibit better performance than other known stabilizers, including those containing toxic heavy metals such as cadmium or lead. The complex is prepared utilizing a Claisen condensation reaction and precipitation with water and heptane.
    Type: Application
    Filed: July 3, 2002
    Publication date: January 8, 2004
    Inventors: Edward Krainer, Michael H. Fisch, Ulrich Stewen, Radu Bacaloglu, Ilze Bacaloglu
  • Patent number: 6667410
    Abstract: The present invention provides a novel process for the conversion of &agr;,&bgr;-unsaturated ketones. This invention is an improvement over existing processes in that it operates at neutral reaction conditions that prevent the formation of side reactions and that it is a single step, which proceeds with complete selectivity and gives a yield that is approximately 30% higher than the currently used processes. An example of this process is the conversion of 16-dehydroprogesterone into 17 &agr;-hydroxyprogesterone.
    Type: Grant
    Filed: September 14, 2001
    Date of Patent: December 23, 2003
    Assignee: Board of Regents, The University of Texas System
    Inventors: Philip D. Magnus, Andrew H. Payne
  • Patent number: 6639112
    Abstract: The invention concerns a method for preparing ketones of formula (I) wherein A and B are as defined in claim 1, consisting of reacting at a temperature ranging between 250 and 500° C. a compound of formula (II): A—X with a compound of formula (III): B—Y, wherein A, B, X and Y are as defined in claim 1, in a coolant solvent having a boiling point higher than 250 ° C.
    Type: Grant
    Filed: April 12, 2002
    Date of Patent: October 28, 2003
    Assignee: Rhodia Chimie
    Inventor: Michel Alas
  • Publication number: 20030144556
    Abstract: Production of unsaturated ketones by the aldol condensation of ketones such as acetone or methyl ethyl ketone by contacting the ketone in the vapour phase with a particulate catalyst comprising at least one basic alkali metal compound supported on an inert substrate at a temperature above 175° C. The produce ketones may be hydrogenated to form saturated ketones or alcohols.
    Type: Application
    Filed: November 18, 2002
    Publication date: July 31, 2003
    Applicant: Imperial Chemical Industries PLC.
    Inventor: Gordon J. Kelly
  • Publication number: 20030139629
    Abstract: A method for preparing ketones in greater yield and selectivity compared to previous catalyzed reactions by acid-catalyzed condensation reaction using a metal-doped polysulfonated ion exchange resin catalyst is disclosed. For example, use of polysulfonated ion exchange resins having at least 5.0 milliequivalents sulfonic acid groups/gram catalyst and loaded with metal, such as palladium, provides enhanced yields of methyl isobutyl ketone from the condensation reaction of acetone compared to use of conventional monosulfonated ion exchange resin catalysts.
    Type: Application
    Filed: December 3, 2002
    Publication date: July 24, 2003
    Inventors: Mark Thornton Vandersall, Rudolf Alfred Weinand
  • Publication number: 20030114713
    Abstract: A process for producing 1,1,1-trifluoroacetone includes the step of conducting in a gas phase a hydrogenolysis of a tetrafluoroacetone, which is represented by the general formula [1], by a hydrogen gas in the presence of a catalyst containing a transition metal, 1
    Type: Application
    Filed: November 20, 2002
    Publication date: June 19, 2003
    Applicant: Central Glass Company, Limited
    Inventors: Masanori Tsukamoto, Takashi Sakaya, Takayuki Nishimiya, Junji Negishi
  • Publication number: 20030065227
    Abstract: A process for producing methyl isobutyl ketone includes introducing acetone into a catalytic distillation. Some of the acetone is converted to mesityl alcohol (‘MSO’), water and, optionally, diacetone alcohol (‘DAA’) and/or other by-products. A product stream comprising MSO, water, and, optionally, DAA, other by-products and/or unreacted acetone is withdrawn from the catalytic distillation zone. When the product stream includes DAA, other by-products and/or unreacted acetone, it is treated in a treatment zone to remove at least some of the DAA, other by-products and/or the unreacted acetone therefrom. The product stream and hydrogen are fed into a reaction zone in which MSO present in the product stream and hydrogen react to form methyl isobutyl ketone (‘MIBK’). A MIBK rich product stream is withdrawn from this reaction zone.
    Type: Application
    Filed: November 7, 2002
    Publication date: April 3, 2003
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Nelis Saayman, Grant James Lund, Sybrandus Kindermans
  • Publication number: 20030050512
    Abstract: The present invention is related to a method for forming aldol condensation products, comprising reacting at least one aldehyde starting material in the presence of an ionic liquid medium and a basic catalyst at a temperature range of from about −20° C. to about 300° C. and at a pressure range of from about 1 atm to about 1000 atm for a sufficient time to form the aldol condensation products. The invention is also directed to a method for forming aldol condensation products, comprising reacting at least one aldehyde starting material in the presence of a basic ionic liquid medium at the same parameters specified above. The advantage of the instant invention is the increased selectivity and productivity of the resulting aldol condensation products formed in ionic liquid media, along with the ability to recycle the ionic liquid for use in producing additional aldol condensation products.
    Type: Application
    Filed: June 26, 2001
    Publication date: March 13, 2003
    Inventors: Christian Peter Mehnert, Nicholas Charles Dispenziere, Richard Henry Schlosberg
  • Patent number: 6525227
    Abstract: A reaction method by a novel Lewis acid catalyst stable in water for organic synthesis by using a metal compound stable in water and functioning as a Lewis acid catalyst and using water as apart or all of a solvent, the metal ion of the metal compound having a hydrolysis constant (pKh) of: 4.3≦pKh≦10.1 and a water exchange rate constant (WERC) of 3.2×106M−1sec−1 or more.
    Type: Grant
    Filed: April 4, 2001
    Date of Patent: February 25, 2003
    Assignee: Japan Science and Technology Corporation
    Inventor: Shu Kobayashi
  • Publication number: 20020115891
    Abstract: A process for producing methyl isobutyl ketone includes introducing acetone into a catalytic distillation. Some of the acetone is converted to mesityl alcohol (‘MSO’), water and, optionally, diacetone alcohol (‘DAA’) and/or other by-products. A product stream comprising MSO, water, and, optionally, DAA, other by-products and/or unreacted acetone is withdrawn from the catalytic distillation zone. When the product stream includes DAA, other by-products and/or unreacted acetone, it is treated in a treatment zone to remove at least some of the DAA, other by-products and/or the unreacted acetone therefrom. The product stream and hydrogen are fed into a reaction zone in which MSO present in the product stream and hydrogen react to form methyl isobutyl ketone (‘MIBK’). A MIBK rich product stream is withdrawn from this reaction zone.
    Type: Application
    Filed: September 11, 2001
    Publication date: August 22, 2002
    Inventors: Nelis Saayman, Grand James Lund, Sybrandus Kindermans
  • Patent number: 6437190
    Abstract: A process for preparing aldols by catalytic reaction of aldehydes and/or ketones comprises conducting said reaction in the channels of a microstructured reaction system.
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: August 20, 2002
    Assignee: Siemens Axiva GmbH & Co. KG
    Inventors: Inga Leipprand, Thorsten Lahrs
  • Patent number: 6433230
    Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising: reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: August 13, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
  • Patent number: 6417406
    Abstract: The present invention provides a process for producing 6-methyl heptanone and corresponding methyl ketones, in particular phytone and tetrahydrogeranyl acetone, by aldolization of aldehydes with acetone in the presence of an aldolization catalyst and a heterogeneous hydrogenation catalyst containing a polyhydric alcohol.
    Type: Grant
    Filed: September 10, 2001
    Date of Patent: July 9, 2002
    Assignee: Degussa AG
    Inventors: Steffen Krill, Klaus Huthmacher
  • Patent number: 6410795
    Abstract: A method for the preparation of 1,3-diketones is disclosed wherein the method comprises the steps of: (A) mixing an alkali metal base with a hindered alcohol in an aromatic hydrocarbon solvent; (B) boiling the mixture and azeotropically distilling water formed by the reaction between the base and the alcohol, whereby a solution of a hindered alkali metal alkoxide is formed in situ in the solvent; (C) mixing an ester with the solution of the hindered alkali metal alkoxide in the aromatic hydrocarbon solvent; and then (D) adding a ketone to the mixture.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: June 25, 2002
    Assignee: Crompton Corporation
    Inventors: Michael H. Fisch, Edward Krainer, Radu Bacaloglu
  • Patent number: 6403346
    Abstract: Enzymatic processes can produce intermediates for manufacturing retiferol derivatives that are useful for treating or preventing hyperproliferative skin diseases and for reversing conditions associated with photodamage. These processes can use as a starting material trihydroxycyclohexane, which can be chemically modified by a process that includes an enzymatic step, typically involving lipases of EC-class 3.1.1.3 or 3.1.1.34.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: June 11, 2002
    Assignee: Basilea Pharmaceutica AG
    Inventors: Hans Hilpert, Beat Wirz
  • Publication number: 20020002309
    Abstract: A process for preparing a compound of the formula: 1
    Type: Application
    Filed: March 28, 2000
    Publication date: January 3, 2002
    Inventors: DIDIER BERNARD, MICHEL CASADO, VIRGINIE PEVERE, ALAIN TRUCHON
  • Patent number: 6329554
    Abstract: Process for the continuous preparation of unsaturated ketones of the formula I where the dashed line can be an additional C—C bond, R1 is an alkyl, and R2 is an aliphatic hydrocarbon having from 1 to 37 carbons, a cycloalkyl or a cycloalkylalkyl, by reacting an unsaturated alcohol of the formula II  with an alkyl acetoacetate of the formula III where R3 is an alkyl having from 1 to 5 carbons, in the presence or organic aluminum compounds as catalyst.
    Type: Grant
    Filed: September 7, 1999
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Carsten Oost, Manfred Stroezel, Heinz Etzrodt, Dietmar Weller, Bernhard Bockstiegel, Klaus Reimer, Gerd Kaibel, Hagen Jaedicke
  • 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: 6300524
    Abstract: The present invention relates to an improved process for preparing higher unsaturated ketones by reacting the corresponding &agr;,&bgr;-unsaturated alcohols with alkyl acetoacetates in a Carroll reaction , in a reactor system with fitted fractionation column, wherein A the &agr;,&bgr;-unsaturated alcohol is introduced into the reaction vessel together with the organic aluminum compound in the absence of effective amounts of a solvent, and the alkyl acetoacetate is metered into this mixture, B a reaction temperature which is as constant as possible at between 175° C. and 220° C., preferably between 180° C. and 200° C., is adjusted and C during the reaction the content of alkyl acetoacetate in the reaction mixture is adjusted to a value which is as constant as possible at between 1 and 3% by weight.
    Type: Grant
    Filed: November 15, 1999
    Date of Patent: October 9, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Carsten Oost, Manfred Stroezel, Heinz Etzrodt, Dietmar Weller, Udo Rheude, Gerd Kaibel, Thomas Krug, Luise Spiske, Hagen Jaedicke
  • Patent number: 6271171
    Abstract: The present invention relates to a process for obtaining a solid catalyst of general formula (I): [(Mg2+)1−x(Al3+)x(OH−)2]x+[(OH−)x]x−(H2O)n  (I) with 0.20≦x≦0.33 and n<1.
    Type: Grant
    Filed: June 4, 1999
    Date of Patent: August 7, 2001
    Assignee: Elf Atochem S.A.
    Inventors: Rémy Teissier, Maurice Fournier
  • Patent number: 6143935
    Abstract: The condensation reaction of a ketone with either an ester or a carbonate to form, respectively, a 1,3-diketone or a .beta.-ketoester often affords poor results under the standard condensation reaction conditions. High yields and high purities of the desired product can be obtained by performing the reaction using an alkoxide base in DMSO as the sole solvent.
    Type: Grant
    Filed: June 2, 1998
    Date of Patent: November 7, 2000
    Assignee: Eastman Chemical Company
    Inventors: Neil W. Boaz, M. Todd Coleman
  • Patent number: 6121497
    Abstract: A process for the recovery of methyl ethyl ketone (MEK) from an aqueous mixture of MEK and ethanol comprising extracting the MEK from the mixture using an extractive solvent selected from the group consisting of isopentane, the o-, m-, m-isomers of xylene, and mixed xylenes. Preferably the extractive solvent is separated from the MFK in the extract by fractional distillation and recycled to the extraction step.
    Type: Grant
    Filed: October 16, 1998
    Date of Patent: September 19, 2000
    Assignee: Celanese International Corporation
    Inventor: Carl David Murphy
  • Patent number: 6069261
    Abstract: A process carried out in a reaction column for the chemical reaction of substances the reaction of which is affected by an unfavorable equilibrium position of the main reaction or a preceding equilibrium, wherein during the reaction one or more substances to be separated are continuously removed from the reaction mixture by one or more auxiliaries.
    Type: Grant
    Filed: May 4, 1998
    Date of Patent: May 30, 2000
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Ulrich Hoffmann, Ulrich Kunz
  • 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: 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: 6046366
    Abstract: The invention relates to the use of compounds of formula:[M(II).sub.1-x M*(III).sub.x (OH).sub.2+x ].mH.sub.2 O (I)in which M(II) represents a divalent cation chosen from the group consisting of nickel, zinc, cobalt, magnesium or the mixture of two or more of the abovementioned metals; M(III) represents a trivalent cation, such as aluminum, gallium, iron or chromium, with the exception of the compound of formula (I) in which M(II) is magnesium and M(III) is aluminum, x is between 0.20 and 0.33 and m.ltoreq.1; in the preparation of .beta.-hydroxycarbonyl and/or .alpha.,.beta.-unsaturated carbonyl compounds.
    Type: Grant
    Filed: December 7, 1998
    Date of Patent: April 4, 2000
    Assignee: Elf Atochem S.A.
    Inventors: Remy Teissier, Didier Tichit
  • 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: 5936131
    Abstract: The present invention relates to a process for obtaining .beta.-hydroxy carbonyl compounds and/or .alpha.,.beta.-unsaturated carbonyl compounds, characterized in that at least one aldehyde or one ketone is brought into contact with a solid catalyst of general formula (I):?(Mg.sup.2+).sub.1-x (Al.sup.3+).sub.x (OH.sup.-).sub.2 !.sup.x+ ?(OH.sup.-).sub.x !.sup.x- (H.sub.2 O).sub.n (I)with 0.20.ltoreq.x.ltoreq.0.33 and n<1.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: August 10, 1999
    Assignee: ELF Atochem S,A
    Inventors: Remy Teissier, Maurice Fournier
  • Patent number: 5936129
    Abstract: A process for making a sterically-hindered beta-diketone involving: (a) providing a solution comprising: (i) an ester; (ii) a base; and (iii) a solvent; (b) adding a ketone selected from the group consisting of an aromatic ketone and a hindered aliphatic ketone, to the solution, to form a condensation reaction mixture, whereby either the ester or the ketone is hindered; (c) reacting the solution with the ketone to form a sterically-hindered beta-diketone; and (d) recovering the sterically-hindered beta-diketone from the condensation reaction mixture.
    Type: Grant
    Filed: January 22, 1998
    Date of Patent: August 10, 1999
    Assignee: Henkel Corporation
    Inventors: Kevin V. Martin, Phillip L. Mattison, Michael J. Virnig
  • Patent number: 5925796
    Abstract: A method for the catalytic manufacture of MIBK and DIBK from DMK and/or IPA (optionally in the presence of water) while obtaining improved control over the ratio of DIBK to MIBK in the product stream, comprising reacting, in the presence of an aldol condensation catalyst, a reactant mixture comprising DMK and/or IPA and an effective amount of an additional reactant selected from the group consisting of mesityl oxide (MSO) and methyl isobutyl carbinol (MIBC) and mixtures thereof. Reaction temperature may also be changed to affect the product ratio obtained. The preferred catalyst is copper-based. An overall excess of hydrogen is desired, and this may be achieved by introducing or recycling hydrogen, and/or by balancing exothermic and endothermic reactions. By this invention, the product ratio of DIBK to MIBK is altered such that, as DMK and/or IPA conversion is increased, a lesser amount of DIBK than normal is produced, resulting in improved ability to control the product ratio of these materials.
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: July 20, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Mark Robert Bassett, Brian Terry Keen
  • Patent number: 5888923
    Abstract: The present invention relates to a modified Raney nickel catalyst which can serves as hydrogenation catalyst for hydroxy aldehydes, such as 4-hydroxy-butanal, and 2-methyl-3-hydroxypropanal and hydroxy cyclic ethers such as 2-hydroxy-tetrahydrofuran. Further, a process for preparing diols by using the modified Raney nickel catalyst is provided.
    Type: Grant
    Filed: April 15, 1996
    Date of Patent: March 30, 1999
    Assignee: Dairen Chemical Corporation
    Inventors: Shien Chang Chen, C. C. Chu, F. S. Lin, J. Y. Chou, C. C. Huang
  • Patent number: 5886233
    Abstract: Described are cyclohexanone derivatives of the formula (I), a method of preparing them and intermediates used in their preparation.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: March 23, 1999
    Assignee: Schering Aktiengesellschaft
    Inventors: Andreas Steinmeyer, Gunter Neef, Gunnar Muller, Hans-Joachim Knolker
  • Patent number: 5886231
    Abstract: A process for preparing a compound of formula (I): ##STR1## by rearrangement of a compound of formula (II): ##STR2## in a non-polar solvent in the presence of a cyanide source, an alkali or alkaline earth metal carbonate, a phase transfer catalyst and 1-6 moles of water with respect to the compound of formula (II).
    Type: Grant
    Filed: June 24, 1997
    Date of Patent: March 23, 1999
    Assignee: Zeneca Limited
    Inventors: Stephen Martin Brown, Howard Rawlinson
  • 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: 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: 5849957
    Abstract: The present invention relates to a process for obtaining isophorone from acetone, characterized in that the operation is carried out (i) in liquid phase in the presence of a magnesium aluminum double oxide of formula Mg.sub.1-x Al.sub.x O.sub.1+x or (ii) either in gaseous or liquid phase in the presence of a catalyst of general formula (I):?(Mg.sup.2+).sub.1-x (Al.sup.3+).sub.x (OH.sup.-).sub.2 !.sup.x+ ?(OH.sup.-).sub.x !.sup.x- (H.sub.2 O).sub.n (I)with 0.20.ltoreq.x.ltoreq.0.33 and n<1.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: December 15, 1998
    Assignee: Elf Atochem S.A.
    Inventors: Remy Teissier, Jacques Kervennal
  • Patent number: 5808165
    Abstract: The present invention is directed to compositions containing novel beta-diketones of formula (I) and formula (II),R.sub.1 COCH.sub.2 COR.sub.2 (I)R.sub.2 COCH.sub.2 COR.sub.2 (II)which may be used to stabilize various polymers, such as polyvinyl chlorides (PVCs). The present invention is also directed to a method for preparing .beta.-diketones by a Claisen condensation reaction, which is represented as follows:R.sub.4 COCHR.sub.5 H+R.sub.6 C(O)OR.sub.7 +RO.sup.- .fwdarw.?R.sub.4 COCR.sub.5 COR.sub.6 !-+R.sub.7 OH+ROH.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: September 15, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Serge Chassaing, Michel Gay, Gilles Mur
  • Patent number: 5703248
    Abstract: The present invention concerns a novel process for the selective trihalogenation of ketones employing organic halogen salts.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: December 30, 1997
    Inventors: Jeffrey S. Rommel, James T. Traxler, Richard R. Boettcher
  • Patent number: 5672764
    Abstract: The aldolization is characterized by the use of a solid basic catalyst which has the following general formula?(Mg.sup.2+).sub.1-x (Al.sup.3+).sub.x (OH.sup.-).sub.2 !.sup.+x ?(OH.sup.-).sub.x (H.sub.2 O).sub.n !.sup.-x (II)wherein 0.20.ltoreq.x.ltoreq.0.33 and n has a value of less than 1. This catalyst has a defined crystal structure similar to that of hydrotalcite or, alternatively, of meixnerite. Also disclosed are processes for the preparation of the catalyst.
    Type: Grant
    Filed: January 5, 1996
    Date of Patent: September 30, 1997
    Assignee: Elf Atochem S.A.
    Inventors: Remy Teissier, Didier Tichit, Fran.cedilla.ois Figueras, Jacques Kervennal
  • Patent number: 5663452
    Abstract: The invention relates to a new, technically simple but efficient process, with a good yield, for the preparation of 2-ethyl-1,3-hexane diol from n-butyraldehyde by aldol condensation in the presence of an alkali metal hydroxide or alkali earth metal hydroxide catalyst. To promote the reaction and to improve its controllability, a neutral phase-transfer catalyst is additionally used in the process according to the invention. 2-Ethyl-1,3-hexane diol is used in insecticides and, for example, in the preparation of polyesters.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: September 2, 1997
    Assignee: Neste OY
    Inventors: Kari Kulmala, Kjell Ankner, Lea Rintala, Leila Lahtinen, Kalevi Heinola
  • Patent number: 5648550
    Abstract: A novel process for the manufacture of .beta.-keto alcohols from aldehydes comprising reacting a conjugated polyene aldehyde under basic conditions with a cyclocarbonate or derivative thereof. Certain carotenoid products of this process are novel compounds and are also an object of the present invention. The products, which for the most part belong to the carotenoid field, find corresponding use, for example, as colorants or pigments for foodstuffs, egg yolk, integuments and/or subcutaneous fat of poultry and flesh and/or integuments of fish and crustaceans.
    Type: Grant
    Filed: December 6, 1995
    Date of Patent: July 15, 1997
    Assignee: Roche Vitamins Inc.
    Inventors: Andreas Brungger, Hansjorg Grundler, Werner Simon