Aldehyde Reacted With Ketone Patents (Class 568/390)
  • Patent number: 11396487
    Abstract: Described is a process of making pseudoionone and hydroxy pseudoionone comprising the steps of (i) preparing a first aqueous mixture comprising first concentrations of acetone, citral and hydroxide, (ii) producing a second aqueous mixture by allowing to react for a reaction time the components of the first aqueous mixture and (iii) producing a third aqueous mixture by adding to the second aqueous mixture a second amount of hydroxide so that an additional amount of pseudoionone is formed in the third aqueous mixture. The invention further suggests an apparatus for making pseudoionone and hydroxy pseudoionone as well as to a respective process and use of said apparatus in making pseudoionone and hydroxy pseudoionone.
    Type: Grant
    Filed: November 13, 2019
    Date of Patent: July 26, 2022
    Assignee: BASF SE
    Inventors: Josias Jakobus Nieuwoudt, Bernhard Brunner, Sven Reining, Timon Stork, Bjoern Kaibel, Alexander Zipp, Oliver Bey
  • Patent number: 9988329
    Abstract: A transfer-hydrogenation process for preparing a carbonyl compound and an alcohol compound comprises the steps of (a) contacting a first carbonyl compound with a first alcohol compound in the presence of a transfer-hydrogenation catalyst in a first reaction zone at conditions effective to form a second carbonyl compound from the first alcohol compound and a second alcohol compound from the first carbonyl compound, and (b) removing the second carbonyl compound from the first reaction zone during step (a). The first carbonyl compound is a saturated aldehyde or ketone, or an ?,?-unsaturated aldehyde or ketone. The first alcohol compound is a primary or secondary alcohol. The second alcohol compound is ?,?-saturated. The transfer-hydrogenation catalyst includes a Group 8 to 11 metal. This process is useful for preparing and higher value alcohols, such as butanol or 2-ethylhexanol, from the corresponding carbonyl compounds by engaging lower alcohol (C2-C4) feedstocks instead of hydrogen (H2).
    Type: Grant
    Filed: February 8, 2017
    Date of Patent: June 5, 2018
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Robert Thomas Hembre, Scott Donald Barnicki, Robert Scott Huss, Xiaopeng Shan, Stephanie Rollins Testerman, Timothy Alan Upshaw, Dewey Wayne Fuller, Jr.
  • Patent number: 9216935
    Abstract: The present invention relates to an improved and sustainable process for producing 3-methyl-3-pentene-2-one which is used in the synthesis of fragrance ingredients for perfumery applications.
    Type: Grant
    Filed: May 21, 2014
    Date of Patent: December 22, 2015
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Sunitha Rao Tadepalli, Geatesh Karunakaran Tampy, James Stevens
  • Publication number: 20150133694
    Abstract: The present invention relates to an improved and sustainable process for producing 3-methyl-3-pentene-2-one which is used in the synthesis of fragrance ingredients for perfumery applications.
    Type: Application
    Filed: May 21, 2014
    Publication date: May 14, 2015
    Applicant: International Flavors & Fragrances Inc.
    Inventors: Sunitha Rao Tadepalli, Geatesh Karunakaran Tampy, James Stevens
  • Patent number: 8921605
    Abstract: Use of pure lanthanum oxide which is obtained by calcination of oxygen-containing lanthanum salts at temperatures of at least 700° C. as heterogeneous catalyst in the aldol condensation of citral and acetone to give pseudoionone, and process for the preparation of pseudoionone by aldol condensation of citral and acetone in the liquid phase using pure lanthanum oxide.
    Type: Grant
    Filed: July 19, 2011
    Date of Patent: December 30, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Wolfgang Hölderich, Verena Ritzerfeld, Bernhard Markus Ernst Russbüldt, Erhard Henning Fleischhauer, Werner Bonrath, Reinhard Karge, Jan Schütz
  • Publication number: 20140275400
    Abstract: The present invention provides methylene beta-diketone monomers, methods for producing the same, and compositions and products formed therefrom. In the method for producing the methylene beta-diketones of the invention, a beta-diketone is reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to further processing, which may be vaporization by contact with an energy transfer means in order to isolate the beta-diketone monomer. The present invention further compositions and products formed from methylene beta-diketone monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).
    Type: Application
    Filed: October 18, 2012
    Publication date: September 18, 2014
    Inventors: Yangbin Chen, Adam G. Malofsky, Jeffrey M. Sullivan, Stanley C. Wojciak, Tanmoy Dey, Bernard M. Malofsky
  • Publication number: 20130310607
    Abstract: Use of pure lanthanum oxide which is obtained by calcination of oxygen-containing lanthanum salts at temperatures of at least 700° C. as heterogeneous catalyst in the aldol condensation of citral and acetone to give pseudoionone, and process for the preparation of pseudoionone by aldol condensation of citral and acetone in the liquid phase using pure lanthanum oxide.
    Type: Application
    Filed: July 19, 2011
    Publication date: November 21, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Wolfgang Hölderich, Verena Ritzerfeld, Bernhard Markus Ernst Russbüldt, Erhard Henning Fleischhauer, Werner Bonrath, Reinhard Karge, Jan Schütz
  • Patent number: 8129570
    Abstract: The present invention relates to a process for the preparation of compounds of a 1,4-dialkyl-2,3-diol-1,4-butanedione by a acidic aldol condensation between an alkyl glyoxal and an ?-hydroxy ketone.
    Type: Grant
    Filed: April 30, 2008
    Date of Patent: March 6, 2012
    Assignee: Firmenich SA
    Inventor: Olivier Andrey
  • Publication number: 20100137620
    Abstract: The present invention relates to a process for the preparation of compounds of a 1,4-dialkyl-2,3-diol-1,4-butanedione by a acidic aldol condensation between an alkyl glyoxal and an ?-hydroxy ketone.
    Type: Application
    Filed: April 30, 2008
    Publication date: June 3, 2010
    Applicant: FIRMENICH SA
    Inventor: Olivier Andrey
  • Patent number: 7411098
    Abstract: The present invention relates to a process for preparing tetrahydrogeranylacetone (tetrahydropseudoionone) by aldol condensation of citral with acetone and subsequent hydrogenation. The invention further relates to the use of thus obtained tetrahydro-geranylacetone for preparing phytol, isophytol, tocopherol and/or tocopherol derivatives. In addition, the invention relates to processes for preparing tocopherols and/or tocopherol derivatives.
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: August 12, 2008
    Assignee: BASF SE
    Inventors: Walter Dobler, Nicolaus Bahr, Alois Kindler, Christian Miller, Axel Salden
  • Patent number: 7321067
    Abstract: The present invention relates to a process for the preparation of compounds of a 1,4-dialkyl-2,3-diol-1,4-butanedione by a catalytic aldol condensation between an alkyl glyoxal and an ?-hydroxy ketone.
    Type: Grant
    Filed: March 28, 2007
    Date of Patent: January 22, 2008
    Assignee: Firmenich SA
    Inventors: Ferdinand Naef, René Decorzant
  • Patent number: 7141698
    Abstract: The invention relates to a continuous process for producing pseudoionones of general formulas (I) and (I?) as well as isomers thereof, whereby: R1 represents CH3 or (a); R2 and R3 represent hydrogen, CH3 or C2H5, and; R4 and R5 represent hydrogen or CH3. These pseudoionones are produced by reacting an aldehyde of formula (II) with an excess of a ketone of general formula (III), whereby R1, R2 and R3 have the aforementioned meanings, in the presence of water and alkali hydroxide at an increased temperature and in a homogeneous solution. The inventive process is characterized in that: a) the intermixing of the homogeneous solution consisting of aldehyde, ketone and aqueous alkali lye occurs at a temperature ranging from 10 to 120° C.
    Type: Grant
    Filed: October 28, 2003
    Date of Patent: November 28, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Dobler, Nicolaus Bahr, Klaus Breuer, Alois Kindler
  • Patent number: 7098366
    Abstract: A supported catalyst is proposed comprising one or more metal oxides as active component on a catalyst support for carrying out an aldol condensation, with the catalyst support being ?-aluminum oxide, the active component comprising one or more oxides of the elements having atomic numbers 39 or from 57 to 71 and the concentration of the active component being in the range from 5 to 12% by weight, based on the weight of the catalyst support.
    Type: Grant
    Filed: December 2, 2002
    Date of Patent: August 29, 2006
    Inventors: Marcus Sigl, Christian Miller, Walter Dobler, Mathias Haake
  • Patent number: 7071361
    Abstract: Continuous single-step processes for producing higher molecular weight ketones are disclosed that involve a liquid-phase crossed condensation of an aldehyde with a ketone in the presence of a hydrogenation catalyst and a small amount of a catalyst comprising a concentrated hydroxide or alkoxide of an alkali-metal (from Group 1 or Group IA of the Periodic Table of the Elements) or alkali-earth metal (from Group 2, or Group IIA of the Periodic Table of the Elements), wherein the amount of water provided to the reaction mixture, or reaction zone, is relatively low, with respect to the total initial weight of the reaction mixture. The reaction may be carried out in the absence of solubilizing agents or phase transfer agents. The product mixture is largely free of by-products resulting from further condensation reactions of the desired ketone product or intermediates, and free of the self-condensation products of the reactant aldehyde, that are afterward difficult to remove from the reaction mixture.
    Type: Grant
    Filed: June 25, 2004
    Date of Patent: July 4, 2006
    Assignee: Fastman Chemical Company
    Inventors: Scott Donald Barnicki, Jennifer Ellen McCusker-Orth, Joseph Franklin Knight, Jerry Lynn Miller
  • Patent number: 6995289
    Abstract: A method for the synthesis of an ?,?-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 ?,?-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: Grant
    Filed: July 31, 2001
    Date of Patent: February 7, 2006
    Assignee: Astrazeneca AB
    Inventors: Ian Patel, Philip Hopes
  • Patent number: 6979751
    Abstract: Processes for producing higher molecular weight ketones are disclosed that include the steps of feeding an aldol catalyst solution, a lower molecular weight aldehyde, and a lower molecular weight ketone, through a reactor provided with a solid hydrogenation catalyst and hydrogen gas; recovering a liquid reactor effluent containing the higher molecular weight ketone as a reaction product; and recycling a portion of the recovered liquid reactor effluent back through the reactor.
    Type: Grant
    Filed: November 14, 2003
    Date of Patent: December 27, 2005
    Assignee: Eastman Chemical Company
    Inventors: Jennifer Ellen McCusker-Orth, Brent Alan Tennant, James Charles Ciula
  • Patent number: 6960694
    Abstract: Processes for producing ?-hydroxy-ketones and ?,?-unsaturated ketones are disclosed which comprise the crossed condensation of an aldehyde with a ketone in the presence of a hydroxide or alkoxide of alkali metal or an alkaline earth metal as catalyst. The products of the process, ?-hydroxy-ketones and ?,?-unsaturated ketones, are useful for the preparation of many commercially important products in the chemical process industries including solvents, drug intermediates, flavors and fragrances, other specialty chemical intermediates.
    Type: Grant
    Filed: July 1, 2003
    Date of Patent: November 1, 2005
    Assignee: Eastman Chemical Company
    Inventors: Scott Donald Barnicki, Jennifer Ellen McCusker-Orth, Jerry Lynn Miller
  • Publication number: 20040133044
    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):
    Type: Application
    Filed: February 23, 2004
    Publication date: July 8, 2004
    Inventors: Shu Kobayashi, Kei Manabe
  • Publication number: 20040122261
    Abstract: Processes for producing higher molecular weight ketones are disclosed that include the steps of feeding an aldol catalyst solution, a lower molecular weight aldehyde, and a lower molecular weight ketone, through a reactor provided with a solid hydrogenation catalyst and hydrogen gas; recovering a liquid reactor effluent containing the higher molecular weight ketone as a reaction product; and recycling a portion of the recovered liquid reactor effluent back through the reactor.
    Type: Application
    Filed: November 14, 2003
    Publication date: June 24, 2004
    Inventors: Jennifer Ellen McCusker-Orth, Brent Alan Tennant, James Charles Ciula
  • Patent number: 6605746
    Abstract: A process for the preparation of methylheptanone and corresponding homologous methyl ketones involves the cross-aldolization of acetone with the corresponding aldehyde. The polar catalyst phase is introduced with acetone and an organic auxiliary solvent phase to form a two phase mixture in the presence of hydrogen. The corresponding aldehyde is then added at temperatures between 40° C. and 200° C. The process can be run in a continuous manner with the polar catalyst phase being recyled after regeneration. The use of the non-polar auxiliary solvent(s) increase yield and selectivity.
    Type: Grant
    Filed: March 14, 2002
    Date of Patent: August 12, 2003
    Assignee: Degussa AG
    Inventors: Steffen Krill, Stephan Kretz, Achim Schneider
  • Patent number: 6603047
    Abstract: A process for conducting multiphase reactions, especially the preparation of &agr;,&bgr;-unsaturated ketones by condensation of aldehydes with ketones.
    Type: Grant
    Filed: February 11, 2002
    Date of Patent: August 5, 2003
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Klaus-Diether Wiese, Wilfried Buschken, Guido Protzmann
  • Patent number: 6583323
    Abstract: Methylheptanone and corresponding homologous methylketones, in particular phytone and tetrahydrogeranyl acetone, are produced by aldol condensation of isovaleraldehyde or prenal or the corresponding aldehydes with acetone in the presence of a catalyst phase, which contains an aldolizing catalyst and a heterogeneous hydrogenating catalyst.
    Type: Grant
    Filed: March 8, 2002
    Date of Patent: June 24, 2003
    Assignee: Degussa AG
    Inventor: Steffen Krill
  • 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
  • Publication number: 20030040645
    Abstract: A process for the preparation of methylheptanone and corresponding homologous methyl ketones involves the cross-aldolization of acetone with the corresponding aldehyde. The polar catalyst phase is introduced with acetone and an organic auxiliary solvent phase to form a two phase mixture in the presence of hydrogen. The corresponding aldehyde is then added at temperatures between 40° C. and 200° C. The process can be run in a continuous manner with the polar catalyst phase being recyled after regeneration. The use of the non-polar auxiliary solvent(s) increase yield and selectivity.
    Type: Application
    Filed: March 14, 2002
    Publication date: February 27, 2003
    Inventors: Steffen Krill, Stephan Kretz, Achim Schneider
  • Publication number: 20020161264
    Abstract: A process for conducting multiphase reactions, especially the preparation of &agr;,&bgr;-unsaturated ketones by condensation of aldehydes with ketones.
    Type: Application
    Filed: February 11, 2002
    Publication date: October 31, 2002
    Applicant: DE GUSSA AG
    Inventors: Klaus-Diether Wiese, Wilfried Buschken, Guido Protzmann
  • Publication number: 20020128517
    Abstract: Methylheptanone and corresponding homologous methylketones, in particular phytone and tetrahydrogeranyl acetone, are produced by aldol condensation of isovaleraldehyde or prenal or the corresponding aldehydes with acetone in the presence of a catalyst phase, which contains an aldolizing catalyst and a heterogeneous hydrogenating catalyst.
    Type: Application
    Filed: March 8, 2002
    Publication date: September 12, 2002
    Applicant: DEGUSA AG
    Inventor: Steffen Krill
  • 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
  • Publication number: 20020058846
    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: Application
    Filed: September 10, 2001
    Publication date: May 16, 2002
    Applicant: Degussa AG
    Inventors: Steffen Krill, Klaus Huthmacher
  • Publication number: 20020026083
    Abstract: A process for protecting aldehydes and ketones in crossed aldol condensations comprising protecting the target ketone by forming a gem-diol with ethylene glycol or aldehyde with ethylene glycol or a mono-hydroxy alcohol to allow the additive ketone or aldehyde to condense with the target thereby minimizing by-products, waste and separation difficulties then decomposing the gem-diol with dilute mineral acid.
    Type: Application
    Filed: July 20, 2001
    Publication date: February 28, 2002
    Inventor: Christian Everett
  • 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: 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
  • 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: 6232506
    Abstract: Provided are a process for producing 6-methyl-3-hepten-2-one by cross aldol condensation carried out while each continuously adding to acetone, isovaleraldehyde and an aqueous alkali containing an alkaline substance; a process for producing a 6-methyl-2-heptanone analogue represented by Formula (1): wherein n is an integer of 0 or 1 or more; which comprises allowing hydrogen, acetone and an aldehyde represented by Formula (2): wherein n is as defined above; X and Y each represents a hydrogen atom or they are coupled together to form a carbon-carbon bond; and Z and W each represents a hydrogen atom or they are coupled together to form a carbon-carbon bond; to react in the presence of an aqueous alkali containing an alkaline substance, and a hydrogenation catalyst; and a process for producing phytone or isophytol using the 6-methyl-3-hepten-2-one or the 6-methyl-2-heptanone analogue.
    Type: Grant
    Filed: June 24, 1999
    Date of Patent: May 15, 2001
    Assignee: Kuraray Co., Lyd.
    Inventors: Yoichi Kido, Noriaki Kumagai, Hideharu Iwasaki, Takashi Onishi, Fuyuo Ueyama
  • Patent number: 6121500
    Abstract: A mixture of water and a glycol, such as ethylene glycol, is employed as the solvent for the reaction between 1,6-dibromo-2-naphthol and an alkali metal sulfite in the preparation of 6-bromo-2-naphthol and its derivatives to effect a substantial reduction in reaction time. The glycol/water mol ratio is ordinarily in the range of 0.1-0.5/1, preferably 0.3/0.5/1.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: September 19, 2000
    Assignee: Albemarle Corporation
    Inventor: Mahmood Sabahi
  • 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: 5955636
    Abstract: Provided are a process for producing 6-methyl-3-hepten-2-one by cross aldol condensation carried out while each continuously adding to acetone, isovaleraldehyde and an aqueous alkali containing an alkaline substance; a process for producing a 6-methyl-2-heptanone analogue represented by Formula (1): ##STR1## wherein n is an integer of 0 or 1 or more; which comprises allowing hydrogen, acetone and an aldehyde represented by Formula (2): ##STR2## wherein n is as defined above; X and Y each represents a hydrogen atom or they are coupled together to form a carbon-carbon bond; and Z and W each represents a hydrogen atom or they are coupled together to form a carbon-carbon bond;to react in the presence of an aqueous alkali containing an alkaline substance, and a hydrogenation catalyst; and a process for producing phyton or isophytol using the 6-methyl -3-hepten-2-one or the 6-methyl-2-heptanone analogue.
    Type: Grant
    Filed: July 2, 1997
    Date of Patent: September 21, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoichi Kido, Noriaki Kumagai, Hideharu Iwasaki, Takashi Onishi, Fuyuo Ueyama
  • 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: 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: 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: 5840992
    Abstract: In order to make it possible to produce 6-methylheptan-2-one, which is useful as a material for synthesizing isophytol or as a material for synthesizing fragrances such as tetrahydrolinalool and dihydrogeraniol, efficiently and in an industrially simple manner, isovaleral and acetone are subjected to aldol condensation in the presence of a basic substance to form a condensate which contains 4-hydroxy-6-methylheptan-2-one, and then the condensate is subjected to hydrogenation reaction under a dehydration condition to obtain the 6-methylheptan-2-one.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: November 24, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoichi Kido, Masahiko Kitayama, Koichi Yoneda, Hideharu Iwasaki, Takashi Onishi
  • Patent number: 5760277
    Abstract: The cycloaliphatic ketones of formula ##STR1## having two conjugated double bonds in positions 1 and 3, or 2 and 4, such as indicated by the dotted lines, and wherein R defines a C.sub.1 to C.sub.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: June 2, 1998
    Assignee: Firmenich SA
    Inventors: Ferdinand Naef, Rene Decorzant
  • 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: 5637774
    Abstract: Disclosed is a very economical way to produce vinyl carbonyls such as ethyl vinyl ketone. Disclosed also is a purification process of separating vinyl carbonyls and coreactants. The catalyst and reaction conditions give useful yields of vinyl carbonyls, the thermodynamically unfavorable product along with coreactants that are more thermodynamically favored. Disclosed also is the separation of reactants that takes place at low distillation temperatures and pressures in the presence of antioxidant.
    Type: Grant
    Filed: September 29, 1995
    Date of Patent: June 10, 1997
    Assignee: Eastman Chemical Company
    Inventor: William A. Beavers
  • Patent number: 5583263
    Abstract: A multistep process for producing amyl ketones is provided. In the process, a methyl ketone is reacted with butyraldehyde to form a C.sub.7 aldol condensation product which is then dehydrated to form an olefinic ketone and hydrogenated to form an amyl ketone. The process is suitable for coproduction along with the production of MIBK and yields products with a high selectivity.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: December 10, 1996
    Assignee: Shell Oil Company
    Inventors: Duraisamy Muthusamy, Chia-Chung Wang, Richard D. Swain, David B. Litzen, William R. Pledger
  • Patent number: 5300654
    Abstract: .beta.-hydroxyketones are prepared by reacting an aldehyde with acetone in the presence of perhydroisoindole or pyrrolidine and water. The resulting .beta.-hydroxyketone is further reacted in the presence of a solvent mixture to produce .alpha.-.beta.-unsaturated ketones.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: April 5, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Masashi Nakajima, Tadashi Kyotani, Mikio Sawaki
  • Patent number: 5072051
    Abstract: Methyl isopropenyl ketone is produced from methyl ethyl ketone and paraformaldehyde under mild reaction conditions utilizing a catalyst comprising a halogen acid salt of a secondary amine and (a) a non-soluble solid oxide of an element selected from Groups IB, IIIA, IVA, IVB, VA, VB, VIB and VIII of the periodic table, or (b) a carboxylic acid. Temperatures of 120-150 and pressures of 700-1400 kpa are preferred; co-products may include ethyl vinyl ketone.
    Type: Grant
    Filed: July 30, 1990
    Date of Patent: December 10, 1991
    Assignee: Aristech Chemical Corporation
    Inventors: Joseph Pugach, Jeffrey S. Salek
  • Patent number: 5026919
    Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: June 25, 1991
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 5004839
    Abstract: Unsaturated ketones are produced from ketones and paraformadehyde under mild reaction conditions utilizing a catalyst comprising a halogen acid salt of a secondary amine and a nonsoluble solid oxide of an element selected from groups IB, IIIA, IVA, IVB, VA, VB, VIB and VIII of the periodic table. Temperatures of 120-150 and pressures of 700-1200 kpa are preferred; by-products may include di-unsaturated ketones such as divinyl ketone. Unsaturated ketones such as methyl vinyl ketone are useful in imparting ultraviolet sensitivity to plastics which enhances degradability.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: April 2, 1991
    Assignee: Aristech Chemical Corporation
    Inventors: Joseph Pugach, Jeffrey S. Salek