Aldehyde Or Ketone Reactant Patents (Class 568/388)
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Patent number: 11987506Abstract: The present invention relates to a salt recovery solution and to a process for separating a salt from an aqueous solution. The present disclosure also relates to a salt recovery solution and to its use to concentrate a salt or brine solution by recovering water therefrom. The salt recovery solution suitable for recovering a salt from an aqueous solution comprises at least one tertiary amine containing compound; and at least one enolisable carbonyl.Type: GrantFiled: January 4, 2023Date of Patent: May 21, 2024Assignee: Aquafortus Technologies LimitedInventors: Daryl Joseph Briggs, Chaitra Prakash
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Patent number: 10329228Abstract: 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: GrantFiled: April 24, 2017Date of Patent: June 25, 2019Assignee: Triad National Security, LLCInventors: Andrew Sutton, Cameron Moore, Rhodri Jenkins, Troy A. Semelsberger
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Patent number: 10065901Abstract: 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: GrantFiled: November 29, 2016Date of Patent: September 4, 2018Assignees: ZHEJIANG NHU COMPANY LTD., SHANDONG NHU PHARMACEUTICAL CO., LTD., ZHEJIANG UNIVERSITYInventors: 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
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Patent number: 9663436Abstract: 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: GrantFiled: June 24, 2015Date of Patent: May 30, 2017Assignee: Lonza LtdInventors: Florencio Zaragoza Doerwald, Christoph Taeschler
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Patent number: 9205408Abstract: 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: GrantFiled: August 13, 2014Date of Patent: December 8, 2015Assignee: Celanese International CorporationInventors: Gustavo Angel Robelo Grajales, Ricardo Alderete Delgadillo
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Patent number: 9120734Abstract: 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: GrantFiled: May 28, 2014Date of Patent: September 1, 2015Assignee: ClearWaterBay Technology, Inc.Inventors: Vaibhav V. Kelkar, Drow Lionel O'Young, Christianto Wibowo, Madhura Kelkar, Hok Chung Chan
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Publication number: 20130204037Abstract: 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: ApplicationFiled: February 7, 2012Publication date: August 8, 2013Applicant: Carter TechnologiesInventor: Melvin Keith Carter
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Patent number: 8455696Abstract: 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: GrantFiled: April 22, 2009Date of Patent: June 4, 2013Assignee: Rhodia Poliamida E Especialidades LTDAInventors: Roberto Nasser, Dalva Janine Rita, Joël Schwartz
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Patent number: 8362302Abstract: 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: GrantFiled: April 16, 2012Date of Patent: January 29, 2013Assignee: King Abdulaziz City for Science and Technology (KACST)Inventors: Abdulaziz A Bagabas, Mohamed Mokhtar Mohamed Mostafa, Abdulrahman A Al-Rabiah, Vagif Malik Akhmedov
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Publication number: 20120220796Abstract: 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: ApplicationFiled: July 29, 2010Publication date: August 30, 2012Inventors: Michael Lefenfeld, Robert Hoch
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Patent number: 8242314Abstract: 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: GrantFiled: November 27, 2006Date of Patent: August 14, 2012Assignee: Sasol Technology (PTY) LimitedInventors: Tristan Erich Hahn, Johannes Jochemus Gildenhuys, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
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Patent number: 8222460Abstract: 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: GrantFiled: July 17, 2008Date of Patent: July 17, 2012Assignee: Dow Global Technologies LLCInventor: Jeffrey Scott Sawrey
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Publication number: 20120172453Abstract: 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: ApplicationFiled: August 31, 2011Publication date: July 5, 2012Inventors: Ben A. Barres, Naoki Nakayama, Hiroaki Serizawa, Ankush B. Argade
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Patent number: 8110708Abstract: 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: GrantFiled: April 27, 2011Date of Patent: February 7, 2012Assignee: King Abdulaziz City for Science and Technology (KACST)Inventors: Abdulaziz A Bagabas, Mohamed Mokhtar Mohamed Mostafa, Abdulrahman A Al-Rabiah, Vagif Melik Akhmedov
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Patent number: 8101805Abstract: 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: GrantFiled: June 7, 2011Date of Patent: January 24, 2012Assignee: King Abdulaziz City for Science and Technology (KACST)Inventors: Abdulrahman A Al-Rabiah, Abdulaziz A Bagabas, Akhmedov Vagif Malik
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Publication number: 20110288240Abstract: 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: ApplicationFiled: August 4, 2011Publication date: November 24, 2011Applicant: 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
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Patent number: 7973198Abstract: 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: GrantFiled: April 17, 2008Date of Patent: July 5, 2011Assignee: BASF SEInventors: Joachim Schmidt-Leithoff, Christoph Jäkel, Rocco Paciello
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Patent number: 7951976Abstract: 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: GrantFiled: August 15, 2010Date of Patent: May 31, 2011Assignee: King Abdulaziz City for Science and Technology (KACST)Inventors: Abdulaziz Ahmed Bagabas, Vagif Melik Akhmedov, Abdulrahman Al-Rabiah, Mohamed Mokhtar Mohamed Mostafa
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Publication number: 20110124922Abstract: 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: ApplicationFiled: November 24, 2010Publication date: May 26, 2011Inventors: Jose Antonio Trejo, Eric J. Langenmayr
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Patent number: 7935849Abstract: 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: GrantFiled: September 14, 2005Date of Patent: May 3, 2011Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Thomas Kircher, Rolf Kuenzi, Johannes Tschumi
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Publication number: 20110039888Abstract: 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: ApplicationFiled: April 21, 2009Publication date: February 17, 2011Inventors: Don M. Coltart, Daniel Lim
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Publication number: 20110040128Abstract: 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: ApplicationFiled: April 22, 2009Publication date: February 17, 2011Inventors: Roberto Nasser, Dalva Janine Rita, Joël Schwartz
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Patent number: 7855311Abstract: 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: GrantFiled: March 10, 2009Date of Patent: December 21, 2010Inventor: Melvin K. Carter
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Publication number: 20100317898Abstract: 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: ApplicationFiled: September 29, 2008Publication date: December 16, 2010Inventors: Barbara Noziere, Armando Cordova
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Publication number: 20100313937Abstract: 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: ApplicationFiled: June 10, 2010Publication date: December 16, 2010Applicant: SYRACUSE UNIVERSITYInventors: Tewodros Asefa, Richard E. Mishler, II, Eric A. Schiff
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Publication number: 20100317897Abstract: 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: ApplicationFiled: July 17, 2008Publication date: December 16, 2010Inventor: Jeffrey Scott Sawrey
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Patent number: 7850841Abstract: 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: GrantFiled: December 12, 2006Date of Patent: December 14, 2010Assignee: Neste Oil OyjInventors: Eija Koivusalmi, Ilkka Kilpeläinen, Pirkko Karhunen, Jorma Matikainen
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Publication number: 20100261237Abstract: 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: ApplicationFiled: October 1, 2008Publication date: October 14, 2010Applicant: EVONIK DEGUSSA GmbhInventors: 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
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Publication number: 20100222612Abstract: 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: ApplicationFiled: November 27, 2006Publication date: September 2, 2010Inventors: Tristan Erich Hahn, Jochemus Gildenhuys Johannes, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
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Patent number: 7767863Abstract: 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: GrantFiled: September 26, 2006Date of Patent: August 3, 2010Inventors: Jeffrey S. Sawrey, Richard W. Wegman
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Patent number: 7671239Abstract: 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: GrantFiled: November 27, 2006Date of Patent: March 2, 2010Assignee: Sasol Technology (Pty) LimitedInventors: Tristan Erich Hahn, Johannes Jochemus Gildenhuys, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
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Patent number: 7652172Abstract: 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: GrantFiled: September 20, 2005Date of Patent: January 26, 2010Assignee: The Trustees of Princeton UniversityInventors: Martin F. Semmelhack, Shawn R. Campagna, Bonnie L. Bassler, Michael J. Federle
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Publication number: 20090306434Abstract: 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: ApplicationFiled: September 26, 2006Publication date: December 10, 2009Inventors: Jeffrey S. Sawrey, Richard W. Wegman
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Publication number: 20090253940Abstract: 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: ApplicationFiled: November 27, 2006Publication date: October 8, 2009Inventors: Tristan Erich Hahn, Johannes Jochemus Gildenhuys, Braam Van Dyk, James Christoffel Crause, Paranjothi Moodliar
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Publication number: 20090112026Abstract: 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: ApplicationFiled: October 29, 2007Publication date: April 30, 2009Applicant: Carter TechnologiesInventor: Melvin Keith Carter
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Patent number: 7504542Abstract: 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: GrantFiled: August 10, 2007Date of Patent: March 17, 2009Assignee: Evonik Degussa GmbHInventors: Ralf Jackstell, Irina Jovel, Matthias Beller, Martin Hateley, Christoph Weckbecker, Klaus Huthmacher
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Patent number: 7495132Abstract: 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: GrantFiled: January 28, 2005Date of Patent: February 24, 2009Assignee: BASF AktiengesellschaftInventors: Christian Walsdorff, Thorsten Johann, Beatrice Roessler, Hartmut Hibst, Joaquim Henrique Teles, Sebastian Storck, Jens Klein
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Patent number: 7456322Abstract: 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: GrantFiled: May 17, 2005Date of Patent: November 25, 2008Assignee: Dow Global Technologies Inc.Inventor: Clark S. Davis
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Patent number: 7393982Abstract: 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: GrantFiled: May 20, 2004Date of Patent: July 1, 2008Assignee: Show A Denko K.K.Inventors: Makoto Saito, Takashi Ueda, Takashi Tani, Keiichi Nakamura
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Patent number: 7351850Abstract: 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: GrantFiled: May 18, 2005Date of Patent: April 1, 2008Assignee: Kuraray Co., Ltd.Inventors: Fumihiko Okabe, Hideki Matsuda, Takashi Yamaguchi
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Patent number: 7345206Abstract: 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: GrantFiled: March 28, 2007Date of Patent: March 18, 2008Assignee: Firmenich SAInventors: Ferdinand Naef, René Decorzant
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Patent number: 7345205Abstract: A process is described for preparing tetrahydrogeranylacetone in which pseudoionone, geranylacetone and/or dihydrogeranylacetone in a liquid phase, in which particles of a catalyst which is capable of preferentially hydrogenating carbon-carbon double bonds over carbon-oxygen double bonds are suspended, is conducted through a device which inhibits the transport of the catalyst particles in the presence of a hydrogen-containing gas.Type: GrantFiled: July 14, 2003Date of Patent: March 18, 2008Assignee: BASF AktiengesellschaftInventors: Hans-Georg Goebbel, Gerd Kaibel, Christian Miller, Walter Dobler, Thomas Dirnsteiner, Thilo Hahn, Klaus Breuer, Werner Aquila
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Patent number: 7323603Abstract: 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: GrantFiled: March 8, 2002Date of Patent: January 29, 2008Assignee: Japan Science and Technology CorporationInventors: Shu Kobayashi, Kei Manabe
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Patent number: 7285685Abstract: Process for preparing alpha, beta-unsaturated acyclic or cyclic carbonyl compounds by dehydrogenation of the corresponding saturated carbonyl compounds in the gas phase over a heterogeneous dehydrogenation catalyst comprising platinum and/or palladium and tin on an oxidic support.Type: GrantFiled: July 22, 2004Date of Patent: October 23, 2007Assignee: BASF AktiengesellschaftInventors: Christian Walsdorff, Beatrice Rössler, Götz-Peter Schindler, Joaquim H. Teles, Klaus Harth
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Patent number: 7084306Abstract: 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: GrantFiled: December 18, 2002Date of Patent: August 1, 2006Assignee: Showa Denko K.K.Inventors: Makoto Saito, Takashi Ueda, Takashi Tani
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Patent number: 7030280Abstract: 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: GrantFiled: August 24, 2004Date of Patent: April 18, 2006Assignee: Central Glass Company, LimitedInventors: Kazumasa Funabiki, Hitoshi Yamamoto, Masashi Nagamori, Masaki Matsui
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Patent number: 7005551Abstract: 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: GrantFiled: March 8, 2005Date of Patent: February 28, 2006Inventor: John Stauffer
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Patent number: 6977314Abstract: 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: GrantFiled: December 3, 2002Date of Patent: December 20, 2005Assignee: Rohm and Haas CompanyInventors: Mark Thornton Vandersall, Rudolf Alfred Weinand
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Patent number: 6933414Abstract: 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: GrantFiled: June 21, 2004Date of Patent: August 23, 2005Inventor: John E. Stauffer
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Patent number: 6872854Abstract: 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: GrantFiled: July 3, 2002Date of Patent: March 29, 2005Assignee: Crompton CorporationInventors: Edward Krainer, Michael H. Fisch, Ulrich Stewen, Radu Bacaloglu, Ilze Bacaloglu