Oxy Containing Reactant Patents (Class 568/391)
  • Patent number: 9199903
    Abstract: The invention relates to a method for catalytically condensing organic compounds containing at least one oxo and/or hydroxyl function into CH acidic compounds and/or coupling said organic compounds to the CH acidic compounds in the presence of a catalyst which comprises an active carbon substrate provided with a metal. The method is suitable in particular for generating higher alcohols, aldehydes, ketones, and/or alkanes as well as mixtures thereof.
    Type: Grant
    Filed: December 13, 2012
    Date of Patent: December 1, 2015
    Assignees: FRAUNHOFER GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG E.V., SASOL GmbH
    Inventors: Axel Kraft, Andreas Menne, Klaas Breitkreuz, Thoralf Gross, Holger Ziehe
  • Publication number: 20140343325
    Abstract: The invention relates to a method for catalytically condensing organic compounds containing at least one oxo and/or hydroxyl function into CH acidic compounds and/or coupling said organic compounds to the CH acidic compounds in the presence of a catalyst which comprises an active carbon substrate provided with a metal. The method is suitable in particular for generating higher alcohols, aldehydes, ketones, and/or alkanes as well as mixtures thereof.
    Type: Application
    Filed: December 13, 2012
    Publication date: November 20, 2014
    Applicant: Fraunhofer Gesellschaft Zur Förderung der angewandtan Forschung e.V.
    Inventors: Axel Kraft, Andreas Menne, Klaas Breitkreuz, Thoralf Gross, Holger Ziehe
  • Patent number: 8748669
    Abstract: Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1˜10:1˜10:1˜10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.
    Type: Grant
    Filed: July 30, 2010
    Date of Patent: June 10, 2014
    Assignees: East China Normal University, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
    Inventors: Shengming Ma, Jinxian Liu, Jinqiang Kuang, Yu Liu, Yuli Wang, Qiong Yu, Weiming Yuan, Suhua Li, Bo Chen, Jiajia Cheng, Baoqiang Wan, Juntao Ye, Shichao Yu
  • Patent number: 8735633
    Abstract: A method comprising reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), without using fermentation or direct oxidation of the glycerol is provided. DHA is useful in various products, including as a sunless tanning agent.
    Type: Grant
    Filed: July 14, 2011
    Date of Patent: May 27, 2014
    Assignee: Board of Trustees of Michigan State University
    Inventors: Dennis Miller, Xi Hong, Carl Lira, Omar McGiveron
  • Patent number: 8729311
    Abstract: The present invention relates to a process for the formation of acetone from acetic acid. The process is conducted at an elevated temperature of above 225° C. by contacting a feed stream containing acetic acid, and an optional carrier gas, with a catalyst. The catalyst comprises a support that is favorable for the production of acetone. The support may comprise titania, zirconia, ceria, silica, iron oxide, and carbon, but preferably is titania, zirconia, and ceria.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: May 20, 2014
    Assignee: Celanese International Corporaton
    Inventors: Zhenhua Zhou, Radmila Jevtic, Victor J. Johnston, Heiko Weiner
  • Patent number: 8541626
    Abstract: Ketones may be produced in high yields from glycerides of short chain fatty acids by reaction with a carboxylic acid. The reaction is conducted in the presence of a catalyst and under conditions effective for ketonization of decanoate with the carboxylic acid to produce free ketones. Reaction of a glyceride comprising at least one ester of decanoic acid with a carboxylic acid selected from acetic acid and/or propionic acid produces 2-undecanone and/or 3-dodecanone, respectively. Catalysts of the formula FemCenAlpOx, wherein m is between about 0.2 to about 0.6, n is about 0.2, p is between about 0.6 to about 0.2, and x is greater than 0, produce significantly higher yields of the ketones than other known metal oxides.
    Type: Grant
    Filed: January 24, 2012
    Date of Patent: September 24, 2013
    Assignee: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Michael A. Jackson, Steven C. Cermak
  • Patent number: 8513467
    Abstract: Described is a method of making 2,4-diones via acid catalyzed or thermally induced ring-opening of a 4-hydroxy-6-substituted-2-pyrone to yield a 2,4-dione.
    Type: Grant
    Filed: May 1, 2012
    Date of Patent: August 20, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Mei Chia
  • Patent number: 8217203
    Abstract: A process for the preparation of E-farnesyl acetone characterized by reaction of nerolidol with isopropenylmethyl ether in the presence of an acidic catalyst at elevated temperature and isolation by fractionated distillation.
    Type: Grant
    Filed: July 22, 2008
    Date of Patent: July 10, 2012
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Rolf Kuenzi
  • Publication number: 20120116127
    Abstract: Process for preparing an alkenone, which comprises the following steps: (a) providing a halogenated precursor of the alkenone; and (b) eliminating the hydrogen halide from said precursor to form the alkenone by a thermolysis treatment selected from the group consisting of flash thermolysis, vacuum thermolysis, and thermolysis under stripping with inert gas.
    Type: Application
    Filed: July 5, 2010
    Publication date: May 10, 2012
    Applicant: SOLVAY SA
    Inventors: Max Braun, Stefan Palsherm, Uta Claassen, Alain Lambert
  • Publication number: 20120014889
    Abstract: A method comprising reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), without using fermentation or direct oxidation of the glycerol is provided. DHA is useful in various products, including as a sunless tanning agent.
    Type: Application
    Filed: July 14, 2011
    Publication date: January 19, 2012
    Inventors: Dennis Miller, Xi Hong, Carl Lira, Omar McGiveron
  • Patent number: 7880038
    Abstract: A metal catalyst obtained by contacting (A) at least one metal or metal compound selected from i) tungsten compounds composed of tungsten and an element of group IIIb, IVb, Vb, or VIb, ii) molybdenum compounds composed of molybdenum and an element of group IIIb, IVb, Vb, or VIb, and iii) tungsten metal and molybdenum metal; (B) at least one compound selected from tertiary amine compounds, tertiary amine oxide compounds, nitrogen-containing aromatic compounds and nitrogen-containing aromatic N-oxide compounds; (C) hydrogen peroxide; and (D) a phosphate compound, is provided.
    Type: Grant
    Filed: April 14, 2004
    Date of Patent: February 1, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaji Hirota, Koji Hagiya
  • Patent number: 7393982
    Abstract: Disclosed is a process for preparing a ?-diketone compound such as 2,6-dimethyl-3,5-heptanedione, which comprises reacting an ester compound such as an alkyl isobutyrate with a ketone compound such as 3-methylbutanone in the presence of an alkali metal alkoxide as a catalyst. The process comprises a step 1 in which an ester compound CR1R2R3COOQ is reacted with a ketone compound CR4R5R6COCH2R7 using an alkali metal alkoxide catalyst to give a ?-diketone compound CR1R2R2R3COCHR4R5R6. (In the formulae, R7 is hydrogen or an alkyl group of 1 to 4 carbon atoms while others are each independently hydrogen or an alkyl group of 1 to 3 carbon atoms, and at least one of R1 to R6 is hydrogen.
    Type: Grant
    Filed: May 20, 2004
    Date of Patent: July 1, 2008
    Assignee: Show A Denko K.K.
    Inventors: Makoto Saito, Takashi Ueda, Takashi Tani, Keiichi Nakamura
  • Patent number: 7351850
    Abstract: A process by which an ?-oxocarbonyl compound useful as an intermediate for pharmaceuticals/agricultural chemicals can be industrially advantageously and efficiently produced in a high yield. The process, which is for producing an ?-oxocarbonyl compound represented by the general formula (I) wherein R1 and R2 are as defined in the description, comprises oxidizing an ?-hydroxycarbonyl compound represented by the general formula (II) with oxygen or air in the presence of a carboxylic acid and at least one vanadium compound selected from divanadium pentaoxide, divanadium trioxide, divanadium tetraoxide, ammonium metavanadate, sodium metavanadate, potassium metavanadate, triethoxyoxovanadium, tripropoxyoxovanadium, triisopropoxyoxovanadium, vanadium oxobis(acetylacetonate) and vanadium tris(acetylacetonate).
    Type: Grant
    Filed: May 18, 2005
    Date of Patent: April 1, 2008
    Assignee: Kuraray Co., Ltd.
    Inventors: Fumihiko Okabe, Hideki Matsuda, Takashi Yamaguchi
  • Patent number: 7351867
    Abstract: The present invention relates to a process of oxidation of alcohols selectively to aldehydes or ketones with molecular oxygen using a TEMPO based catalyst, Fe-bipyridyl or Fe-phenantroline co-catalyst and N-bromosuccinimide promoter in acetic acid solvent. The oxidation takes places at high rates and high aldehyde selectivity at temperatures in the range 45-50° C. and oxygen or air pressures of 0-15 psi. The alcohol conversion of 95-100% and aldehyde selectivity higher than 95% are achieved over 3-4 hours reaction time. Aldehydes such as 3,3-dimethyl-1-butanal can be produced efficiently using the present invention.
    Type: Grant
    Filed: February 24, 2005
    Date of Patent: April 1, 2008
    Assignee: The NutraSweet Company
    Inventors: Setrak K. Tanielyan, Robert L. Augustine, Indra Prakash, Kenneth E. Furlong, Handley E. Jackson
  • Patent number: 7326798
    Abstract: The invention relates to a new synthetic process for the production of key intermediates useful in the synthesis of epothilones or epothilone derivatives, to certain compounds used to produce these key intermediates and to a process to produce said compounds.
    Type: Grant
    Filed: April 21, 2005
    Date of Patent: February 5, 2008
    Assignee: Schering AG
    Inventors: Johannes Platzek, Orlin Petrov, Marc Willuhn, Klaus Dieter Graske, Werner Skuballa
  • Patent number: 7323603
    Abstract: A method for aldol reaction in water, which comprises: reacting an aldehyde with a silyl enol ether in an aqueous medium in the presence of a boronic acid represented by the following general formula (1): R1R2BOH??(1) (wherein R1 and R2 are the same or different hydrocarbon groups that may contain a substituent), a surfactant, and a Brønsted acid is provided. This method for aldol reaction in water uses a catalytic amount of the boron source to give products in high yield and selectivity.
    Type: Grant
    Filed: March 8, 2002
    Date of Patent: January 29, 2008
    Assignee: Japan Science and Technology Corporation
    Inventors: Shu Kobayashi, Kei Manabe
  • Patent number: 7084306
    Abstract: Disclosed is a process for preparing 2,2,6,6-tetramethyl-3,5-heptanedione, comprising reacting a pivalic acid alkyl ester with pinacolone in the presence of an alkali metal alkoxide catalyst using a pivalic acid alkyl ester as a solvent but using no other solvent or reacting them in an amide type or urea type solvent in the presence of an alkali metal alkoxide catalyst. Also disclosed is a process for preparing a 2,2,6,6-tetramethyl-3,5-heptanesione metal complex using the 2,2,6,6-tetramethyl-3,5-heptanedione obtained by the above process. The process for preparing 2,2,6,6-tetramethyl-3,5-heptanedione is an industrially advantageous process in which an alkali metal alkoxide that is easy to handle can be used as a catalyst for preparing 2,2,6,6-tetramethyl-3,5-heptanedione from a pivalic acid alkyl ester and pinacolone.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: August 1, 2006
    Assignee: Showa Denko K.K.
    Inventors: Makoto Saito, Takashi Ueda, Takashi Tani
  • Patent number: 7060859
    Abstract: The invention concerns the use of a solid basic catalyst comprising a hydrotalcite structure wherein part at least of the compensating anions are fluoride anions F? for producing Knoevenagel of Michael condensation reactions. The invention also concerns novel solid basic catalysts comprising a hydrotalcite structure characterized by a Mg/Al molar ratio ranging between 2.5 and 3.8 wherein at least part of the compensating anions are fluoride anions F?, and methods for preparing said novel catalysts.
    Type: Grant
    Filed: June 6, 2005
    Date of Patent: June 13, 2006
    Assignee: Council of Scientific and Industrial Research
    Inventors: Francois Figueras, Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Vattipally Neeraja, Kottapalli Koteswara Rao
  • Patent number: 7030280
    Abstract: The present invention provides a process for producing an optically active ?-trifluoromethyl-?-hydroxycarbonyl compound represented by formula (3): comprising a step of reacting a fluoral equivalent represented by formula (1): with a carbonyl compound represented by formula (2): in the presence of an optically active amino acid or a derivative thereof.
    Type: Grant
    Filed: August 24, 2004
    Date of Patent: April 18, 2006
    Assignee: Central Glass Company, Limited
    Inventors: Kazumasa Funabiki, Hitoshi Yamamoto, Masashi Nagamori, Masaki Matsui
  • Patent number: 7015358
    Abstract: A process for the production of aliphatic or alicyclic monoketones or alicyclic diketones of the formula R1—C(?O)—R2 in which R1 is a linear or branched C1-10-alkyl group and R2 is a linear or branched C1-10-alkyl group or a phenyl group, or R1 or R2 together are —(CH2)m—[C(?O)]n—(CH2)p—, wherein m and p independently are integers from 1 to 4 and n is 0 or 1, thus forming an alicyclic ring together with the carbonyl group of R1—C(?O)—R2 by oxidizing a secondary alcohol of formula R1?—CHOH—R2? in which R1? and R2? either have the same meaning as R1 and R2 above or, if R1 and R2 together are —(CH2)m—[C(?O)]n—(CH2)p—, are together —(CH2)m—(CHOH)n—(CH2)p— wherein m, n and p are as defined above, with a peroxy compound in the presence of a carboxylic acid and a manganese(IV) complex of 1,4,7-trimethyl-1,4,7-triazacyclononane.
    Type: Grant
    Filed: April 23, 2002
    Date of Patent: March 21, 2006
    Assignee: Lonza AG
    Inventors: Georg Süss-Fink, Georgiy B Shul′Pin, Lidia S. Shul′Pina
  • 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: 6969776
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: November 29, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6933413
    Abstract: The present invention provides a process for the preparation of hexafluoroacetone characterized by bringing hexafluoro-1,2-epoxypropane into contact with at least one catalyst selected from the group consisting of titanium oxide catalysts and fluorinated titanium oxide catalysts to isomerize hexafluoro-1,2-epoxypropane; and a process for the preparation of hexafluoroacetone hydrate characterized by absorbing the hexafluoroacetone prepared by the above process into water to produce crude hexafluoroacetone hydrate, neutralizing the crude hexafluoroacetone hydrate with an alkali, and distilling the resulting mixture. According to the invention, high-purity hexafluoroacetone can be obtained by isomerization of hexafluoro-1,2-epoxypropane with little formation of by-products, and substantially acid-free high-purity hexafluoroacetone hydrate can also be obtained.
    Type: Grant
    Filed: July 2, 2002
    Date of Patent: August 23, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
  • Patent number: 6872854
    Abstract: Metal salts of organic acids complexed with ?-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: Grant
    Filed: July 3, 2002
    Date of Patent: March 29, 2005
    Assignee: Crompton Corporation
    Inventors: Edward Krainer, Michael H. Fisch, Ulrich Stewen, Radu Bacaloglu, Ilze Bacaloglu
  • Patent number: 6803488
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: October 12, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6720456
    Abstract: The present invention relates to a novel process for the preparation of 2,3-pentanedione starting with hydroxyacetone and paraldehyde.
    Type: Grant
    Filed: November 7, 2002
    Date of Patent: April 13, 2004
    Assignee: Symrise GmbH & Co. KG
    Inventors: Stefan Lambrecht, Oliver Franke, Klaus Zahlmann
  • 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
  • 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: 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: 20020198411
    Abstract: Allyl alcohols are converted into corresponding aldehydes or ketones in a high yield under a mild condition by using an inexpensive aluminum alkoxide as an Oppenauer oxidation catalyst and a hydride acceptor. Thus, there is provided an industrially useful method for converting allyl alcohols to corresponding aldehydes or ketones.
    Type: Application
    Filed: May 21, 2002
    Publication date: December 26, 2002
    Applicant: NIKKEN CHEMICALS CO., LTD.
    Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
  • Publication number: 20020169342
    Abstract: A process for the preparation of &bgr;,&ggr;,&dgr;-unsaturated ketones and/or &agr;,&bgr;,&ggr;,&dgr;-unsaturated ketones by the reaction of an unsaturated alcohol with an enol ether or mixture of enol ethers, with formation of ketals as a by-product, at temperatures of from 50° C. to 200° C., in the presence of an acid catalyst, whereby one or all of the reagents is/are heated to the reaction temperature of from 50° C. to 200° C. before the acid catalyst is added.
    Type: Application
    Filed: April 26, 2002
    Publication date: November 14, 2002
    Applicant: DEGUSSA AG
    Inventors: Nongyuan Shi, Bernd Drapal, Steffen Krill, Markus Julino, Klaus Huthmacher
  • Publication number: 20020161263
    Abstract: A process for the preparation of ketones corresponding to the general Formula I 1
    Type: Application
    Filed: April 26, 2002
    Publication date: October 31, 2002
    Applicant: DEGUSSA AG
    Inventors: Nongyuan Shi, Steffen Krill, Klaus Huthmacher, Bernd Drapal
  • 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: 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: 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: 6303823
    Abstract: A process for preparing ketones by so-called “crossed aldol condensation” of a ketone with an aldehyde in the presence of a catalyst system consisting of approximately equimolar amounts of a secondary amine and of a carboxylic acid containing at least 2 C atoms, to form an &agr;,&bgr;-unsaturated ketone, and, where appropriate, subsequent catalytic hydrogenation. The process is used in particular for preparing 6-methyl-3-hepten-2-one by reacting acetone with isovaleraldehyde, and for preparing its hydrogenation product, 6-methylheptan-2-one, which is an important precursor for numerous active substances, in particular for preparing lipid-soluble vitamins such as vitamin E.
    Type: Grant
    Filed: December 5, 2000
    Date of Patent: October 16, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Kramer, Christian Knoll, Johann-Peter Melder, Wolfgang Siegel, Gerd Kaibel
  • Patent number: 6300522
    Abstract: A process is provided for the preparation of compounds of Formula (1): wherein X1 and X2 are each independently H, Cl or F, provided that at least one of X1 and X2 is Cl or F; one of R1 and R2 is H and the other is OH; and R5 is an unsubstituted alkyl, preferably a C1-6 alkyl, group.
    Type: Grant
    Filed: November 29, 2000
    Date of Patent: October 9, 2001
    Assignee: Avecia Limited
    Inventors: John Crosby, Kevin Douglas Bailey, Michael John Monteith
  • 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
  • Publication number: 20010003784
    Abstract: A process for preparing ketones by so-called “crossed aldol condensation” of a ketone with an aldehyde in the presence of a catalyst system consisting of approximately equimolar amounts of a secondary amine and of a carboxylic acid containing at least 2 C atoms, to form an &agr;,&bgr;-unsaturated ketone, and, where appropriate, subsequent catalytic hydrogenation.
    Type: Application
    Filed: December 5, 2000
    Publication date: June 14, 2001
    Inventors: Andreas Kramer, Christian Knoll, Johann-Peter Melder, Wolfgang Siegel, Gerd Kaibel
  • 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: 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: 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: 5618982
    Abstract: Ketones having at least one hydrogen atom or ester group in the .alpha.-position with respect to a ketonic carbonyl group thereof, for example cyclopentanone, 2-methylcyclopentanone and other substituted cyclopentanones, are effectively C- or .alpha.-alkylated, especially on an industrial scale, by reacting same with an alkylating agent in the presence of a catalytically effective amount of a condensed or uncondensed orthophosphate anion.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: April 8, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Laurent Gilbert, Michel Spagnol
  • 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: 5354915
    Abstract: This invention provides an improved process for converting .alpha.,.beta.-olefinically unsaturated aldehydic or ketonic compounds into the corresponding allylic alcohol using an alcohol as a hydrogen donor. This process is conducted in the presence of a supported tetragonal zirconium oxide catalyst or supported HfO.sub.2, V.sub.2 O.sub.5, NbO.sub.5, TiO.sub.2 and Ta.sub.2 O.sub.5 catalysts.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: October 11, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Walter T. Reichle
  • Patent number: 5276200
    Abstract: The present invention provides a method of preparing sodium formyl acetone using acetone, methyl formate and sodium methoxide as raw materials. A mixture consisting of an acetone and a methyl formate is supplied to a methanol solution of sodium methoxide, or an acetone and a methyl formate are separately supplied simultaneously to the methanol solution of sodium methoxide. The resultant mixture is sufficiently stirred over a predetermined period of time so as to carry out the reaction to form sodium formyl acetone. Also provided is a method of preparing 4,4-dimethoxy-2-butanone. In this method, the reaction mixture obtained in the reaction to form sodium formyl acetone is directly charged into a reaction vessel simultaneously with sulfuric acid to neutralize and acetalize sodium formyl acetone contained in the reaction mixture so as to obtain 4,4-dimethoxy-2-butanone.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: January 4, 1994
    Assignee: Ube Industries, Ltd.
    Inventors: Keigo Nishihira, Shuji Tanaka, Masahiro Kondo
  • Patent number: 5231232
    Abstract: Methods of forming unsaturated C-18 ketones which can be used in the synthesis of Vitamins E and K.sub.1 are disclosed. One procedure involves coupling a C-9 primary allylic halide to a carbonyl-group-containing C-9 terminal alkyne. A second, two-step procedure employs a C-4 bis allylic halide (molar excess) and a carbonyl-group-containing C-9 terminal alkyne to form a C-13 primary allylic halide. The C-13 primary allylic halide can then be converted to the desired C-18 ketone by reaction with 2-methyl-3-butyn-2-ol. Novel C-18 ketones (e.g., 14-hydroxy-6,14-dimethyl-10-methylene-5-pentadecen-7,12-diyn-2-one), C-13 allylic halides (e.g., 10-chloromethyl-6-methyl-5,10-undecadien-7-yn-2-one) and C-9 allylic halides (e.g., 6-chloromethyl-2-methyl-6-hepten-3-yn-2-ol) are formed in the process.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: July 27, 1993
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • 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: 5159117
    Abstract: A process for preparing .alpha.,.alpha.-dialkoxy ketones of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.30 -cycloalkylakyl, C.sub.9 -C.sub.30 -alkylcycloalkyl, unsubstituted or C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy-, halogen-, C.sub.1 -C.sub.4 -haloalkyl-, C.sub.1 -C.sub.4 -haloalkoxy-, phenyl-, phenoxy-, halophenyl-, halophenoxy- and/or cyano-substituted aryl, C.sub.7 -C.sub.20 -aralkyl or heterocyclyl,R.sup.2 is also ##STR2## R.sup.3 and R.sup.4 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -arylalkyl, or together are an unsubstituted or C.sub.1-C.sub.4 -alkyl- substituted C.sub.2 -C.sub.7 -alkylene chain andR.sup.5 is R.sup.1 or together with R.sup.1 is an unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.2 -C.sub.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: October 27, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Wegner, Stefan Karbach, Hubert Smuda, Eckhard Hickmann, Reiner Kober, Rainer Seele, Thomas Zierke