Aldehyde Or Ketone Reactant Patents (Class 568/388)
  • Patent number: 10329228
    Abstract: A process for the production of saturated or unsaturated aliphatic alcohols and/or hydrocarbons includes condensing acetone and/or alcohol(s) to form one or more carbonyl compounds, and hydrogenating and/or hydrodeoxygenating at least one of the one or more carbonyl compounds to form the saturated or unsaturated alcohol(s) and/or hydrocarbons. In some embodiments, the condensation of acetone and/or alcohol(s) may be carried out in the presence of a solid acid catalyst and a transition metal catalyst. The saturated or unsaturated aliphatic alcohols and/or hydrocarbons may include one or more saturated linear C9 alcohols, C9 alkanes and/or one or more mono-unsaturated C9 alkenes.
    Type: Grant
    Filed: April 24, 2017
    Date of Patent: June 25, 2019
    Assignee: Triad National Security, LLC
    Inventors: Andrew Sutton, Cameron Moore, Rhodri Jenkins, Troy A. Semelsberger
  • Patent number: 10065901
    Abstract: The present invention discloses a method for preparing optically active carbonyl compound, comprising the following steps: under the catalysis of chiral amine salt and transition metal catalysts, with hydrogen and catalytic amount of dihydropyridine compound as hydrogen source, use ?, ?-unsaturated aldehydes or ?, ?-unsaturated troponoid compounds to conduct asymmetric catalytic reaction to obtain the optically active carbonyl compound. This method comes in moderate reaction condition, simple operation, and catalytic amount of dihydropyridine compounds usage, the target product is easy to be separated and purified from the reaction system, and the metal catalyst can be recycled, it is economical.
    Type: Grant
    Filed: November 29, 2016
    Date of Patent: September 4, 2018
    Assignees: ZHEJIANG NHU COMPANY LTD., SHANDONG NHU PHARMACEUTICAL CO., LTD., ZHEJIANG UNIVERSITY
    Inventors: Yougui Zhou, Ming Yu, Jintao Yuan, Lei Zhao, Xiandong Zhu, Guangxiong Yu, Weiwei Su, Weikang Shao, Xingxing Shi, Yin Zhang, Ming Feng, Zhirong Chen, Haoran Li, Yuhong Zhang
  • Patent number: 9663436
    Abstract: The invention discloses a method for the preparation of 4-alkoxy-1,1,1-trifluorobut-3-en-2-ones from 1,1,1-trifluoroacetone.
    Type: Grant
    Filed: June 24, 2015
    Date of Patent: May 30, 2017
    Assignee: Lonza Ltd
    Inventors: Florencio Zaragoza Doerwald, Christoph Taeschler
  • Patent number: 9205408
    Abstract: In one embodiment, the invention is to a catalyst composition comprising lime and cement. Preferably, the catalyst composition comprises the lime and the cement in a weight ratio of at least 3.5:1 respectively.
    Type: Grant
    Filed: August 13, 2014
    Date of Patent: December 8, 2015
    Assignee: Celanese International Corporation
    Inventors: Gustavo Angel Robelo Grajales, Ricardo Alderete Delgadillo
  • Patent number: 9120734
    Abstract: Embodiments of the present invention describe systems and methods for production of methyl isobutyl ketone (MIBK) from acetone and hydrogen in a two-step process. In a first step, acetone is converted to a product stream containing mesityl oxide (MO) at a temperature in the range of about 0-120° C. and a pressure in the range of about 1-3 atm. The composition of the product stream from the first reaction step is adjusted so that the resulting stream can undergo a favorable liquid-liquid separation in a decanter, and an MO rich product stream can be recovered. The composition of the feed to the decanter is controlled by choosing the number of reactor stages for the first reaction step and their operating temperatures, and/or by recycling some MIBK to the decanter feed. The method does not require a substantially complete conversion of acetone in the first reaction step, nor does it require a removal of DAA from the product of the first reaction step by separation.
    Type: Grant
    Filed: May 28, 2014
    Date of Patent: September 1, 2015
    Assignee: ClearWaterBay Technology, Inc.
    Inventors: Vaibhav V. Kelkar, Drow Lionel O'Young, Christianto Wibowo, Madhura Kelkar, Hok Chung Chan
  • Publication number: 20130204037
    Abstract: A catalytic process is taught for non-oxidative alkylation of organic compounds, comprising alcohols, alkanes, glycols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, thiols or phosphines, by alkyl groups produced from alcohols or glycols, forming products comprising ethers and other higher molecular weight alkylated compounds. The process is conducted at a reflux temperature below 200° C. in the presence of an acid, alkali or neutral salt dehydrating agent comprising sulfuric acid, phosphoric acid or their salts, lime or anhydrous calcium sulfate in the absence of zero valent metals and air. Specifically, this catalytic process converts ethanol to ethyl butyl ethers, ethyl hexyl ethers and dibutyl ethers or oxygenated gasoline as well as amines comprising n-butyl amine plus butanol to dibutyl amine and butyl hexyl amines at ambient pressure.
    Type: Application
    Filed: February 7, 2012
    Publication date: August 8, 2013
    Applicant: Carter Technologies
    Inventor: Melvin Keith Carter
  • Patent number: 8455696
    Abstract: Production of a ketone or aldehyde prepared by condensation is optimized by dehydration and hydrogenation of a starting acetone/ketone or aldehyde in a reaction zone and wherein water is partially eliminated from such reaction product by at least one membrane pervaporation module, the pervaporation module being fed tangentially and situated laterally to the reaction zone and operating in a loop, and wherein a fraction of reaction product exiting the reaction zone is thus partially dehydrated and recycling such dehydrated concentrate to the reaction zone.
    Type: Grant
    Filed: April 22, 2009
    Date of Patent: June 4, 2013
    Assignee: Rhodia Poliamida E Especialidades LTDA
    Inventors: Roberto Nasser, Dalva Janine Rita, Joël Schwartz
  • Patent number: 8362302
    Abstract: Isopropyl alcohol is a very useful chemical that is widely used in the industry as a solvent. Economical and easy process to make ispopropyl alcohol using novel composite catalyst is described in the instant application. Production of isopropyl alcohol (IPA) from dimehtyl ketone (DMK) and hydrogen (H2) in gas-phase using a ruthenium nano-particle-supported on activated charcoal/nano-zinc oxide composite catalyst is described. Gas phase production of isopropyl alcohol using DMK and hydrogen is also described using optimal time on stream, temperature, catalyst ratio and DMK/H2 ratio. Ruthenium nano-zinc oxide composite catalyst is formulated using different ratios of ruthenium activated charcoal and n-ZnO is described. CAT-IV is shown to be the best performer for the efficient production of isopropyl alcohol.
    Type: Grant
    Filed: April 16, 2012
    Date of Patent: January 29, 2013
    Assignee: King Abdulaziz City for Science and Technology (KACST)
    Inventors: Abdulaziz A Bagabas, Mohamed Mokhtar Mohamed Mostafa, Abdulrahman A Al-Rabiah, Vagif Malik Akhmedov
  • Publication number: 20120220796
    Abstract: A catalytic process for dehydration of an aliphatic C2-C6 alcohol to its corresponding olefin is disclosed. The process continuously flows through a reaction zone a liquid phase containing an aliphatic C2-C6 alcohol to contact a non-volatile acid catalyst at a reaction temperature and pressure to at least partially convert the aliphatic C2-C6 alcohol in the liquid phase to its corresponding olefin. The reaction pressure is greater than atmospheric pressure and the reaction temperature is above the boiling point of the olefin at reaction pressure, but below the critical temperature of the alcohol, and the olefin product is substantially in the gaseous phase. After the contacting step, the olefin containing gaseous phase is separated from the liquid phase. The invention also relates to catalytic processes such as a hydrolysis of an olefin to an alcohol, an esterification, a transesterification, a polymerization, an aldol condensation or an ester hydrolysis.
    Type: Application
    Filed: July 29, 2010
    Publication date: August 30, 2012
    Inventors: Michael Lefenfeld, Robert Hoch
  • Patent number: 8242314
    Abstract: This invention relates to a method of producing purified methyl isobutyl ketone (MIBK) comprising subjecting a feed stream containing MIBK and impurities to a first distillation procedure from which acetone is recovered and a bottom product containing MIBK and impurities is withdrawn. This bottom product is fed to a second distillation column, where a vapor overhead product is withdrawn, condensed and fed to an overhead liquid-liquid separator. Part of an organic phase from the overhead liquid-liquid separator is fed to the second distillation column and part is fed to a third distillation column. A vapor overhead product is withdrawn from the third column which is condensed in the same said condenser. The condensed product is fed to the same said overhead liquid-liquid separator, and purified MIBK is withdrawn from the third distillation column. This invention also relates to an apparatus used in such a method.
    Type: Grant
    Filed: November 27, 2006
    Date of Patent: August 14, 2012
    Assignee: Sasol Technology (PTY) Limited
    Inventors: Tristan Erich Hahn, Johannes Jochemus Gildenhuys, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
  • Patent number: 8222460
    Abstract: MIBC and/or a mixture of IBHK and TMN is produced from MIBK by a process comprising the step of contacting MIBK with hydrogen under condensation/hydrogenation/dehydration reactive conditions and in the presence of a catalytic amount of a Cu-based condensation/hydrogenation/dehydration catalyst. The relative amounts of MIBC and the mixture of IBHK and TMN are controlled by the reaction temperature, a lower temperature, e.g., 130 C., favoring MIBC alone, and a higher temperature, e.g., 200 C., favoring a mixture of MIBC and IBHK plus TMN.
    Type: Grant
    Filed: July 17, 2008
    Date of Patent: July 17, 2012
    Assignee: Dow Global Technologies LLC
    Inventor: Jeffrey Scott Sawrey
  • Publication number: 20120172453
    Abstract: This invention relates to the 5-cis and 5-trans isomers of geranylgeranyl acetone, preferably such synthetic isomers, and pharmaceutical compositions containing such isomers. Other aspects of this invention relate to the use of geranylgeranyl acetone and its isomers in methods for inhibiting neural death, increasing neural activity, and increasing axon growth and cell viability. Geranylgeranyl acetone is a known anti-ulcer drug used commercially and in clinical situations. GGA has also been shown to exert cytoprotective effects on a variety of organs, such as the eye, brain, and heart.
    Type: Application
    Filed: August 31, 2011
    Publication date: July 5, 2012
    Inventors: Ben A. Barres, Naoki Nakayama, Hiroaki Serizawa, Ankush B. Argade
  • Patent number: 8110708
    Abstract: Ruthenium/activated charcoal (Ru/AC) treated with synthesized nano-ZnO (n-ZnO) is used for the first time as a novel composite catalyst in one-step self-condensation of acetone (DMK) to methyl isobutyl ketone in the gas phase. The DMK self-condensation was performed under atmospheric pressure, in a tubular glass fixed-bed microreactor, under DMK and H2 continuous flow at temperature in the range of 523 to 648 K. Addition of n-ZnO to Ru/AC resulted in a pronounced increase in the degree of dispersion of Ru and in the acidic/basic sites concentration ratio. For the one-step synthesis of MIBK at 623 K, the composite catalyst with 2.5 wt % Ru loading was an active and selective bi-functional composite catalyst with balanced acid/base and hydrogenation properties. At 523 K, isopropyl alcohol, product of DMK-direct hydrogenation, was produced in high selectivity for instantly investigated composite catalyst.
    Type: Grant
    Filed: April 27, 2011
    Date of Patent: February 7, 2012
    Assignee: King Abdulaziz City for Science and Technology (KACST)
    Inventors: Abdulaziz A Bagabas, Mohamed Mokhtar Mohamed Mostafa, Abdulrahman A Al-Rabiah, Vagif Melik Akhmedov
  • Patent number: 8101805
    Abstract: A low-pressure one-step gas-phase process for the production and recovery of methyl isobutyl ketone (MIBK) is disclosed. One-step gas-phase synthesis of MIBK from acetone and hydrogen over nano-Pd/nano-ZnCr2O4 catalyst at atmospheric pressure is used as an example. The said process is designed to recover the additional heat associated with the reactor effluent via heating acetone feed and recycle (mixed acetone) before entering the reactor. A compressor is introduced to the gas-phase process to increase slightly the reactor effluent pressure before this effluent is cooled and fed to a flash drum. The compressed reactor effluent is used to preheat hydrogen feed and recycle (mixed hydrogen) before entering the reactor. The separation scheme of low-pressure one-step gas-phase process comprises of several distillation columns used for MIBK separation and purification.
    Type: Grant
    Filed: June 7, 2011
    Date of Patent: January 24, 2012
    Assignee: King Abdulaziz City for Science and Technology (KACST)
    Inventors: Abdulrahman A Al-Rabiah, Abdulaziz A Bagabas, Akhmedov Vagif Malik
  • Publication number: 20110288240
    Abstract: A phosphazene-supported catalyst in which a support is bonded to a group represented by the general formula (1): wherein n, Zn?, a, b, c, d, R, R1 and D are all defined. The phosphazene-supported catalyst is highly effective to catalyze various organic reactions, and further has no reduction of activity even after recovery and reuse of the catalyst, thus it being economically advantageous. In addition, the polymerization of cyclic monomers, substitution of substituents, carbon-carbon bond forming reactions and the like can be conducted with extremely high efficiency.
    Type: Application
    Filed: August 4, 2011
    Publication date: November 24, 2011
    Applicant: Mitsui Chemicals, Inc.
    Inventors: Naritoshi YOSHIMURA, Shinji Kiyono, Kazumi Mizutani, Isao Hara, Takaomi Hayashi, Tadahito Nobori, Yoshihiro Yamamoto, Miyuki Konno, Yoshihisa Inoue, Akira Matsuura, Tuneyuki Ohkubo
  • Patent number: 7973198
    Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand, the optically active catalyst which has at least one carbon monoxide ligand and is to be used in each case being prepared by pretreating a catalyst precursor with a gas mixture comprising carbon monoxide and hydrogen and the asymmetric hydrogenation being performed in the presence of carbon monoxide supplied additionally to the reaction mixture.
    Type: Grant
    Filed: April 17, 2008
    Date of Patent: July 5, 2011
    Assignee: BASF SE
    Inventors: Joachim Schmidt-Leithoff, Christoph Jäkel, Rocco Paciello
  • Patent number: 7951976
    Abstract: Several metal-supported catalyst compositions based on nano-crystalline zinc oxide were synthesized and characterized by X-ray powder diffraction (XRD), Carbon dioxide temperature programmed desorption (CO2 TPD), and nitrogen adsorption at ?196° C. The Pd-supported nano-ZnO mixed with different oxides such as Cr2O3, CrO3, MgO, and ?-Al2O3 showed high catalytic activity in acetone condensation in gas-phase process under hydrogen flow. This reaction involves the base-acid coupling of acetone to form mesityl oxide, followed by its hydrogenation to methyl isobutyl ketone (MIBK). The novel catalyst 1% wt. n-Pd/n-ZnCr2O4 was utilized during gas-phase reaction during production of MIBK. MIBK selectivity was 70-72% at 66-77% acetone conversion at 300-350° C. Diisobutyl ketone (DIBK) was the main by-product, with a total MIBK+DIBK selectivity up to 88%. The prepared catalysts showed stable activity and may be used repeatedly and for a longer period of time.
    Type: Grant
    Filed: August 15, 2010
    Date of Patent: May 31, 2011
    Assignee: King Abdulaziz City for Science and Technology (KACST)
    Inventors: Abdulaziz Ahmed Bagabas, Vagif Melik Akhmedov, Abdulrahman Al-Rabiah, Mohamed Mokhtar Mohamed Mostafa
  • Publication number: 20110124922
    Abstract: This invention relates to the composition of metal alloy-doped heterogeneous catalysts and their method of use. In particular the present invention relates to the composition and use of cost-effective metal alloy-doped ion exchange resin catalysts which provide for comparable yield and selectivity compared to the catalysts previously used.
    Type: Application
    Filed: November 24, 2010
    Publication date: May 26, 2011
    Inventors: Jose Antonio Trejo, Eric J. Langenmayr
  • Patent number: 7935849
    Abstract: Saturated aliphatic ketones, e.g. hexahydropseudoionone, may be prepared by hydrogenating an olefinically unsaturated ketone, e.g. pseudoionone in a continuous fixed-bed mode in the absence of a solvent in the presence of a catalyst comprising a noble metal deposited on a carrier.
    Type: Grant
    Filed: September 14, 2005
    Date of Patent: May 3, 2011
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Thomas Kircher, Rolf Kuenzi, Johannes Tschumi
  • Publication number: 20110039888
    Abstract: The present invention relates, generally, to asymmetric ?-functionalization and to asymmetric ?,?-bisfunctionalization of ketones and aldehydes and, in particular, to chiral auxiliaries suitable for use in effecting such functionalizations and to methods of using same.
    Type: Application
    Filed: April 21, 2009
    Publication date: February 17, 2011
    Inventors: Don M. Coltart, Daniel Lim
  • Publication number: 20110040128
    Abstract: Production of a ketone or aldehyde prepared by condensation is optimized by dehydration and hydrogenation of a starting acetone/ketone or aldehyde in a reaction zone and wherein water is partially eliminated from such reaction product by at least one membrane pervaporation module, the pervaporation module being fed tangentially and situated laterally to the reaction zone and operating in a loop, and wherein a fraction of reaction product exiting the reaction zone is thus partially dehydrated and recycling such dehydrated concentrate to the reaction zone.
    Type: Application
    Filed: April 22, 2009
    Publication date: February 17, 2011
    Inventors: Roberto Nasser, Dalva Janine Rita, Joël Schwartz
  • Patent number: 7855311
    Abstract: Aldehyde and ketone reactants are converted to hydroxyaldehydes, polyhydroxyaldehydes, hydroxyketones and/or polyhydroxyketones in liquid phase by an aldol condensation process where a selected product carbon chain length is produced using specific concentrations of soluble inorganic base at sub-ambient temperature.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: December 21, 2010
    Inventor: Melvin K. Carter
  • Publication number: 20100317898
    Abstract: Present invention presents catalytic systems for aldol condensation reactions. The efficiency of the catalytic systems of the present invention is comparable to those of the classical strong acid or strong base catalysts.
    Type: Application
    Filed: September 29, 2008
    Publication date: December 16, 2010
    Inventors: Barbara Noziere, Armando Cordova
  • Publication number: 20100313937
    Abstract: A method for synthesizing a phosphonic acid functionalized mesoporous metal oxide material (e.g., silica, titania, alumina, preferably silica material) is provided. Further, a method of using the phosphonic acid functionalized mesoporous silica material as a solid acid catalyst in a pinicole-pinacolone rearrangement reaction, and a method of using a phosphonic acid functionalized mesoporous silica material as a solid acid catalyst in a transesterification reaction is provided. A method for preparing a mesoporous titania film for use in a dye sensitized solar cell is also provided.
    Type: Application
    Filed: June 10, 2010
    Publication date: December 16, 2010
    Applicant: SYRACUSE UNIVERSITY
    Inventors: Tewodros Asefa, Richard E. Mishler, II, Eric A. Schiff
  • Publication number: 20100317897
    Abstract: MIBC and/or a mixture of IBHK and TMN is produced from MIBK by a process comprising the step of contacting MIBK with hydrogen under condensation/hydrogenation/dehydration reactive conditions and in the presence of a catalytic amount of a Cu-based condensation/hydrogenation/dehydration catalyst. The relative amounts of MIBC and the mixture of IBHK and TMN are controlled by the reaction temperature, a lower temperature, e.g., 130 C, favoring MIBC alone, and a higher temperature, e.g., 200 C, favoring a mixture of MIBC and IBHK plus TMN.
    Type: Application
    Filed: July 17, 2008
    Publication date: December 16, 2010
    Inventor: Jeffrey Scott Sawrey
  • Patent number: 7850841
    Abstract: The invention relates to a process for producing high-quality hydrocarbon base oil particularly of biological origin. The process of the invention comprises aldol condensation, hydrodeoxygenation, and isomerization steps. Aldehydes and/or ketones, preferably of biological origin are used as the feedstock.
    Type: Grant
    Filed: December 12, 2006
    Date of Patent: December 14, 2010
    Assignee: Neste Oil Oyj
    Inventors: Eija Koivusalmi, Ilkka Kilpeläinen, Pirkko Karhunen, Jorma Matikainen
  • Publication number: 20100261237
    Abstract: The invention describes a process for preparing acetone starting from acetyl-coenzyme A comprising process steps A. enzymatic conversion of acetyl-CoA into acetoacetyl-CoA B. enzymatic conversion of acetoacetyl-CoA into acetoacetate and CoA and C. decarboxylation of acetoacetate to acetone and CO2, which is characterized in that the coenzyme A is not transferred in process step B to an acceptor molecule. In addition, process step B is surprisingly catalysed by enzymes of the classes of acyl-CoA thioesterase, acyl-CoA synthetase or acyl-CoA thiokinase. A completely novel metabolic pathway is concerned, because the enzymatic hydrolysis of acetoacetyl-CoA without simultaneous transfer of CoA to a receptor molecule has never previously been described for any microbial enzyme.
    Type: Application
    Filed: October 1, 2008
    Publication date: October 14, 2010
    Applicant: EVONIK DEGUSSA Gmbh
    Inventors: Stefan Verseck, Steffen Schaffer, Werner Freitag, Friedrich-Georg Schmidt, Matthias Orschel, Gerda Grund, Wilfried Schmidt, Hubert Johannes Bahl, Ralf-Joerg Fischer, Antje May, Peter Duerre, Simone Lederle
  • Publication number: 20100222612
    Abstract: This invention relates to a method of producing purified methyl isobutyl ketone (MIBK) comprising subjecting a feed stream containing MIBK and impurities to a first distillation procedure from which acetone is recovered and a bottom product containing MIBK and impurities is withdrawn. This bottom product is fed to a second distillation column, where a vapour overhead product is withdrawn, condensed and fed to an overhead liquid-liquid separator. Part of an organic phase from the overhead liquid-liquid separator is fed to the second distillation column and part is fed to a third distillation column. A vapour overhead product is withdrawn from the third column which is condensed in the same said condensor. The condensed product is fed to the same said overhead liquid-liquid separator, and purified MIBK is withdrawn from the third distillation column. This invention also relates to an apparatus used in such a method.
    Type: Application
    Filed: November 27, 2006
    Publication date: September 2, 2010
    Inventors: Tristan Erich Hahn, Jochemus Gildenhuys Johannes, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
  • Patent number: 7767863
    Abstract: An improved method for the manufacture of MIBK and DIBK from DMK and/or IPA, by reacting, in the presence of an aldol condensation catalyst, a gaseous mixture comprising hydrogen and DMK and/or IPA. The improvement is the use of a reaction pressure greater than 207 kPa (30 psig) to increase the ratio of MIBK to DIBK. In addition a method for the manufacture of MIBK and DIBK by reacting, in the presence of an aldol condensation catalyst, a gaseous mixture consisting essentially of DMK and/or IPA and optionally water.
    Type: Grant
    Filed: September 26, 2006
    Date of Patent: August 3, 2010
    Inventors: Jeffrey S. Sawrey, Richard W. Wegman
  • Patent number: 7671239
    Abstract: This invention relates to a method of producing purified methyl isobutyl ketone (MIBK) comprising subjecting a feed stream containing MIBK and impurities to a first distillation procedure from which acetone is recovered. The bottom product of the first distillation procedure is fed to a liquid-liquid separator and an organic phase from the said liquid-liquid separator is fed to the top region of a second distillation column to produce an overhead product. The said overhead product is condensed and fed to the said liquid-liquid separator. A bottom product containing MIBK is withdrawn from the second distillation column. This bottom product is fed to a third distillation column, high boiling impurities are withdrawn as a bottom product, and purified MIBK is also withdrawn. The invention also relates to an apparatus used in such a method.
    Type: Grant
    Filed: November 27, 2006
    Date of Patent: March 2, 2010
    Assignee: Sasol Technology (Pty) Limited
    Inventors: Tristan Erich Hahn, Johannes Jochemus Gildenhuys, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
  • Patent number: 7652172
    Abstract: This invention provides a practical synthesis route for 4,5-dihydroxypentane-2,3-dione (DPD), an unstable small molecule which is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis route includes new intermediates and allows preparation of isotopically-labeled DPD and ent-DPD. The method provides sufficient quantities of DPD for study of spontaneous binding of borate to DPD, the signal for the marine bacteria V. harveyi.
    Type: Grant
    Filed: September 20, 2005
    Date of Patent: January 26, 2010
    Assignee: The Trustees of Princeton University
    Inventors: Martin F. Semmelhack, Shawn R. Campagna, Bonnie L. Bassler, Michael J. Federle
  • Publication number: 20090306434
    Abstract: An improved method for the manufacture of MIBK and DIBK from DMK and/or IPA, by reacting, in the presence of an aldol condensation catalyst, a gaseous mixture comprising hydrogen and DMK and/or IPA. The improvement is the use of a reaction pressure greater than 207 kPa (30 psig) to increase the ratio of MIBK to DIBK. In addition a method for the manufacture of MIBK and DIBK by reacting, in the presence of an aldol condensation catalyst, a gaseous mixture consisting essentially of DMK and/or IPA and optionally water.
    Type: Application
    Filed: September 26, 2006
    Publication date: December 10, 2009
    Inventors: Jeffrey S. Sawrey, Richard W. Wegman
  • Publication number: 20090253940
    Abstract: This invention relates to a method of producing purified methyl isobutyl ketone (MIBK) comprising subjecting a feed stream containing MIBK and impurities to a first distillation procedure from which acetone is recovered. The bottom product of the first distillation procedure is fed to a liquid-liquid separator and an organic phase from the said liquid-liquid separator is fed to the top region of a second distillation column to produce an overhead product. The said overhead product is condensed and fed to the said liquid-liquid separator. A bottom product containing MIBK is withdrawn from the second distillation column. This bottom product is fed to a third distillation column, high boiling impurities are withdrawn as a bottom product, and purified MIBK is also withdrawn. The invention also relates to an apparatus used in such a method.
    Type: Application
    Filed: November 27, 2006
    Publication date: October 8, 2009
    Inventors: Tristan Erich Hahn, Johannes Jochemus Gildenhuys, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
  • Publication number: 20090112026
    Abstract: Aldehyde and ketone reactants have been converted to hydroxyaldehydes, polyhydroxyaldehydes, hydroxyketones and/or polyhydroxyketones in aqueous liquid phase by an aldol condensation process where product carbon chain length was limited using specific dilute concentrations of soluble inorganic base. Reactions were reproducibly conducted at ambient pressure in a temperature range of ?25° C. to 50° C. and completed in ten minutes or less following reactant addition.
    Type: Application
    Filed: October 29, 2007
    Publication date: April 30, 2009
    Applicant: Carter Technologies
    Inventor: Melvin Keith Carter
  • Patent number: 7504542
    Abstract: The present invention relates to the preparation of ?-hydroxy ketones of the general formula I. In particular, the invention relates to novel imidazolinium carboxylate adducts and to a novel process for using catalytic amounts of imidazolium and imidazolinium carboxylate adducts in the acyloin reaction of aldehydes to prepare hydroxy ketones of the general formula I, where R and R? are the same or different and are each H or a straight-chain or branched and optionally substituted C1-C12-alkyl radical, and R??H3CSCH2CH2, t-butyl, n-butyl, sec-butyl, n-propyl, i-propyl, an optionally heteroatom-substituted C6-C18-aryl, heteroaryl, C6-C18-arylalkyl, especially phenylmethyl, where phenyl may again be heteroatom-substituted, or heteroalkyl.
    Type: Grant
    Filed: August 10, 2007
    Date of Patent: March 17, 2009
    Assignee: Evonik Degussa GmbH
    Inventors: Ralf Jackstell, Irina Jovel, Matthias Beller, Martin Hateley, Christoph Weckbecker, Klaus Huthmacher
  • Patent number: 7495132
    Abstract: The present invention relates to a catalytically active composition comprising as active component Pd and Bi and at least one element selected from the group (a) consisting of Rh, Au, Sb, V, Cr, W, Mn, Fe, Co, Ni, Na, Cs and Ba, or Pd, Rh and Bi and optionally an element selected from the group (a?) consisting of Au, Sb, V, Cr, W, Mn, Fe, Co, Ni, Pt, Cu, Ag, Na, Cs, Mg, Ca and Ba. The present invention further provides a process for dehydrogenating hydrocarbons, preferably oxo-functionalized hydrocarbons such as cyclopentanone, cyclohexanone and isovaleraldehyde, using the catalytically active composition.
    Type: Grant
    Filed: January 28, 2005
    Date of Patent: February 24, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Christian Walsdorff, Thorsten Johann, Beatrice Roessler, Hartmut Hibst, Joaquim Henrique Teles, Sebastian Storck, Jens Klein
  • Patent number: 7456322
    Abstract: A process for preparing 1,3-dibromoacetone, 1-3-dichloroacetone and epichlorohydrin which comprises: (a) re-acting acetone with 2 moles of bromine to make a mixture of brominated acetone derivatives and byproduct hydrogen bromide; (b) equilibrating the mixture of brominated acetone derivatives and hydrogen bromide to produce 1,3-dibromoacetone as the major product; (c) crystallizing the 1,3-dibromoacetone; and (d) isolating the 1,3-dibromoacetone. The process may further include the steps of (e) reacting the 1,3-dibromoacetone with a chloride source to produce 1,3-dichloroacetone; (f) hydrogenating the isolated 1,3-dichloroacetone to produce 1,3-dichlorohydrin; and (g) cyclizing the 1,3-dichlorohydrin with a base to produce epichlorohydrin.
    Type: Grant
    Filed: May 17, 2005
    Date of Patent: November 25, 2008
    Assignee: Dow Global Technologies Inc.
    Inventor: Clark S. Davis
  • 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: 7345206
    Abstract: The present invention relates to the field of organic synthesis and more particularly to a new process for the dimerisation of alkyl glyoxals, said process being promoted by an alkaline salt of the hydroxymethanesulfinic acid and is performed at a pH comprised between 3.5 and 9.5.
    Type: Grant
    Filed: March 28, 2007
    Date of Patent: March 18, 2008
    Assignee: Firmenich SA
    Inventors: Ferdinand Naef, René Decorzant
  • Patent number: 7345205
    Abstract: A process is described for preparing tetrahydrogeranylacetone in which pseudoionone, geranylacetone and/or dihydrogeranylacetone in a liquid phase, in which particles of a catalyst which is capable of preferentially hydrogenating carbon-carbon double bonds over carbon-oxygen double bonds are suspended, is conducted through a device which inhibits the transport of the catalyst particles in the presence of a hydrogen-containing gas.
    Type: Grant
    Filed: July 14, 2003
    Date of Patent: March 18, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Georg Goebbel, Gerd Kaibel, Christian Miller, Walter Dobler, Thomas Dirnsteiner, Thilo Hahn, Klaus Breuer, Werner Aquila
  • Patent number: 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: 7285685
    Abstract: Process for preparing alpha, beta-unsaturated acyclic or cyclic carbonyl compounds by dehydrogenation of the corresponding saturated carbonyl compounds in the gas phase over a heterogeneous dehydrogenation catalyst comprising platinum and/or palladium and tin on an oxidic support.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: October 23, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Christian Walsdorff, Beatrice Rössler, Götz-Peter Schindler, Joaquim H. Teles, Klaus Harth
  • Patent number: 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: 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: 7005551
    Abstract: A process is provided for the production of acetaldehyde from formaldehyde and methyl chloride. In the process formaldehyde is reacted in the vapor phase with methyl chloride to produce acetaldehyde and hydrogen chloride. The byproduct hydrogen chloride may be recovered from the process to produce additional methyl chloride from methyl alcohol.
    Type: Grant
    Filed: March 8, 2005
    Date of Patent: February 28, 2006
    Inventor: John Stauffer
  • Patent number: 6977314
    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: Grant
    Filed: December 3, 2002
    Date of Patent: December 20, 2005
    Assignee: Rohm and Haas Company
    Inventors: Mark Thornton Vandersall, Rudolf Alfred Weinand
  • Patent number: 6933414
    Abstract: A process is provided for the production of acetone from formaldehyde and methyl chloride. In the process formaldehyde is reacted in the vapor phase with methyl chloride to produce acetone and hydrogen chloride. Acetaldehyde may be formed as an intermediate in the reaction. The byproduct hydrogen chloride may be recovered from the process to produce additional methyl chloride from methyl alcohol.
    Type: Grant
    Filed: June 21, 2004
    Date of Patent: August 23, 2005
    Inventor: John E. Stauffer
  • 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
  • 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