Preparing Esters By Dehydrogenation Of Alcohols Patents (Class 560/239)
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Patent number: 11506620Abstract: A double capsule assembly includes an outer capsule and an inner capsule configured to be positioned within the outer capsule. The inner capsule is configured to have a sample positioned therein. The double capsule assembly is configured to be placed in a solid media assembly to analyze or synthesize the sample.Type: GrantFiled: July 16, 2019Date of Patent: November 22, 2022Assignee: United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Kevin Righter
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Patent number: 10279984Abstract: A cartridge for obtaining a beverage by injecting into the cartridge a pressurized fluid, comprising a box-like body, which accommodates a substance from which it is possible to extract the beverage, and which accommodates on its inside an insert which separates the substance from a bottom wall of the box-like body, forming an interspace. The insert comprises an orifice for the passage of the beverage toward the interspace, whereas the bottom wall comprises a region which can be pierced to obtain an opening for the outflow of the beverage. In the interspace there is a basin which is arranged laterally with respect to the pierceable region in order to accumulate the beverage received directly from the orifice and make it flow out of the opening by overflowing.Type: GrantFiled: February 18, 2013Date of Patent: May 7, 2019Assignee: ILLYCAFFE' S.P.A.Inventors: Luca Mastropasqua, Angelo Dori, Stefano Santagiuliana, Giuseppe Cutuli, Gaia Brollo, Furio Suggi Liverani, Gianluca Giamba
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Patent number: 10077226Abstract: Processes are disclosed for the conversion of 1,6-hexanediol to adipic acid employing a chemocatalytic reaction in which 1,6-hexanediol is reacted with oxygen in the presence of particular heterogeneous catalysts including at least one of platinum or gold. The metals are preferably provided on a support selected from the group of titania, stabilized titania, zirconia, stabilized zirconia, silica or mixtures thereof, most preferably zirconia stabilized with tungsten. The reaction with oxygen is carried out at a temperature from about 100° C. to about 300° C. and at a partial pressure of oxygen from about 50 psig to about 2000 psig.Type: GrantFiled: October 17, 2016Date of Patent: September 18, 2018Assignee: Archer-Daniels-Midland CompanyInventors: Eric L. Dias, Vincent J. Murphy, James A. W. Shoemaker
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Patent number: 9790164Abstract: The present invention is related to a novel and improved process for the production of dehydrolinalyl acetate (DLA), which IUPAC name is acetic acid 1-ethynyl-1,5-dimethyl-hex-4-enyl ester, starting from dehydrolinalool (DLL), which IUPAC name is 3,7-dimethyloct-6-en-1-yn-3-ol, by acetylation.Type: GrantFiled: May 7, 2014Date of Patent: October 17, 2017Assignee: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Fabrice Aquino, Johannes Tschumi
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Patent number: 9000212Abstract: Provided by the present invention is a method for efficient oxidation of alcohols by using, as a catalyst for dehydrogenation oxidation, a ruthenium complex which can be easily produced and easily handled and is obtainable at a relatively low cost. The invention relates to a method of producing a compound having a carbonyl group by dehydrogenation oxidation of alcohols by using as a catalyst the ruthenium carbonyl complex represented by the following general formula (1) RuXY(CO)(L) (1) (in the general formula (1), X and Y may be the same or different from each other and represent an anionic ligand, and L represents a tridentate aminodiphosphine ligand).Type: GrantFiled: April 18, 2012Date of Patent: April 7, 2015Assignee: Takasago International CorporationInventors: Taichiro Touge, Kunimori Aoki, Hideki Nara, Wataru Kuriyama
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Publication number: 20140243519Abstract: The present invention includes compounds useful as intermediates in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing macrolactams. One use of the methods and intermediates described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity.Type: ApplicationFiled: August 16, 2012Publication date: August 28, 2014Inventors: Nobuyoshi Yasuda, Jeffrey T. Kuethe, Guy Humphrey, Gregory L. Beutner, Yong-Li Zhong, Edward Cleator, Carl Baxter
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Publication number: 20140235890Abstract: Catalysts and methods for their manufacture and use for the dehydrogenation of alcohols are disclosed. The catalysts and methods utilize a highly dispersible alumina, for example, boehmite or pseudoboehmite, to form catalysts that exhibit high dehydrogenation activities. Specifically, the catalysts include Cu that is highly dispersed by reaction of an alumina formed by peptizing of boehmite or pseudoboehmite and precursors of ZrO2, ZnO and CuO.Type: ApplicationFiled: April 1, 2014Publication date: August 21, 2014Applicant: BASF CorporationInventors: Rostam Jai Madon, Peter Nagel, Deepak S. Thakur
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Publication number: 20140142013Abstract: The present invention is generally directed to monoester-based lubricant compositions. The present invention is also directed to methods of making these and other similar lubricant compositions. In some embodiments, the methods for making such monoester-based lubricants utilize a biomass precursor and/or low value Fischer-Tropsch (FT) olefins and/or alcohols so as to produce high value monoester-based lubricants. In some embodiments, such monoester-based lubricants are derived from FT olefins and fatty acids. The fatty acids can be from a bio-based source (i.e., biomass, renewable source) or can be derived from FT alcohols via oxidation.Type: ApplicationFiled: November 20, 2012Publication date: May 22, 2014Applicant: Chervon U.S.A. Inc.Inventor: Saleh Ali Elomari
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Patent number: 8703994Abstract: A process for preparing carboxylic acid derivatives of the formula H—(C?O)—R, R is OR1 or NR2R3, R1 is optionally substituted C1-C15-alkyl, C5-C10-cycloalkyl, C5-C10-heterocyclyl, C5-C10-aryl or C5-C10-heteroaryl, substituents are C1-C15-alkyl, C1-C6-alkoxy, C5-C10-cycloalkyl or C5-C10-aryl; R2 and R3 are independently hydrogen or optionally substituted C1-C15-alkyl, C5-C10 cycloalkyl, C5-C10-heterocyclyl, C5-C10-aryl or C5-C10-heteroaryl, substituents are selected from the group consisting of C1-C15-alkyl, C5-C10-cycloalkyl and C5-C10-aryl or R2 and R3 together with the nitrogen atom form a five- or six-membered ring which optionally comprises one or more heteroatoms selected from O, S and N and bearing the substituent R4, R4 is hydrogen or C1-C6-alkyl; by reacting a reaction mixture comprising carbon dioxide, hydrogen and an alcohol of the formula R1—OH or an amine of the formula NHR2R3 in the presence of a catalyst comprising gold at a pressure from 0.2 to 30 MPa and a temperature from 20 to 200° C.Type: GrantFiled: July 26, 2012Date of Patent: April 22, 2014Assignee: BASF SEInventors: Thomas Schaub, Rocco Paciello, Marek Pazicky, Giuseppe Fachinetti, Debora Preti
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Publication number: 20140024854Abstract: The present invention relates to a process for preparing carboxylic acid esters, comprising the reaction of at least one primary monoalcohol or of a mixture of a primary monoalcohol and at least one alcohol different therefrom in the presence of a transition metal carbene complex catalyst K which has, as central atom M, at least one transition metal atom of group 8, 9 or 10 of the Periodic Table of the Elements (IUPAC) and at least one monodentate N-heterocyclic carbene ligand, in the presence of a base, wherein the catalyst K is prepared by reacting a transition metal compound V which has at least one transition metal atom of group 8, 9 or 10 of the Periodic Table of the Elements (IUPAC), but no carbene ligand, with an imidazolium salt in the presence of the primary monoalcohol and the base, the reaction being carried out without dilution.Type: ApplicationFiled: July 17, 2013Publication date: January 23, 2014Inventors: Thomas Schaub, Stefan Rüdenauer, Daniel Schneider, Rocco Paciello
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Publication number: 20140012037Abstract: A method of purifying an ethyl acetate stream comprises contacting an inlet stream with a solvent, transferring at least a portion of the impurity compound from the inlet stream into the solvent to form an extract and a purified product, separating the extract from the purified product, separating the portion of the impurity compound from the extract, forming an impurities stream and a regenerated solvent, and recycling at least a portion of the regenerated solvent to contact the inlet stream. The inlet stream comprises ethyl acetate and an impurity compound, and the extract comprises the solvent and the portion of the impurity compound transferred from the inlet stream.Type: ApplicationFiled: September 10, 2013Publication date: January 9, 2014Inventors: Sagar B. Gadewar, Peter K. Stoimenov
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Publication number: 20130296603Abstract: Dehydrogenative coupling can be achieved in nearly quantitative conversions and yields using a membrane reactor.Type: ApplicationFiled: May 3, 2013Publication date: November 7, 2013Applicant: KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGYInventor: KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY
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Publication number: 20130281664Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e.Type: ApplicationFiled: October 11, 2011Publication date: October 24, 2013Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
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Patent number: 8562921Abstract: A process for the production of high purity ethyl acetate from ethanol is described. The process involves reacting ethanol over a suitable catalyst in a reactive distillation column. The reactive distillation setup allows overcoming the reaction equilibrium for increased conversion of ethanol. Hydrogen is removed as the distillate and ethyl acetate is obtained as a bottoms product from the reactive distillation column. A feed of hydrogen at the bottom of the column and a suitable hydrogenation catalyst placed at the bottom of the column allows for a significant reduction of impurities such as butan-2-one and/or n-butyraldehyde in the ethyl acetate product. Adding side reactors to the reactive distillation column allows additional catalyst holdup for improved reactant conversion.Type: GrantFiled: March 16, 2012Date of Patent: October 22, 2013Assignee: Greenyug, LLC.Inventor: Sagar B. Gadewar
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Patent number: 8558025Abstract: A process for the production of high purity ethyl acetate from ethanol is described. The process involves reacting ethanol over a suitable catalyst in a reactive distillation column. The reactive distillation setup allows overcoming the reaction equilibrium for increased conversion of ethanol. Hydrogen is removed as the distillate and ethyl acetate is obtained as a bottoms product from the reactive distillation column. A feed of hydrogen at the bottom of the column and a suitable hydrogenation catalyst placed at the bottom of the column allows for a significant reduction of impurities such as butan-2-one, butyraldehyde in the ethyl acetate product. Adding side reactors to the reactive distillation column allows additional catalyst holdup for improved reactant conversion.Type: GrantFiled: October 20, 2010Date of Patent: October 15, 2013Assignee: Greenyug, LLCInventor: Sagar B Gadewar
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Publication number: 20130197266Abstract: A reactive distillation method comprises introducing an feed stream comprising ethanol to a reactive distillation column, contacting the feed stream with a catalyst in the reactive distillation column during a distillation, where the feed stream reacts in the presence of the catalyst to produce a reaction product comprising ethyl acetate and hydrogen, removing ethyl acetate during the distillation from the reactive distillation column as a bottoms stream, and removing hydrogen during the distillation from the reactive distillation column as an overhead stream.Type: ApplicationFiled: February 1, 2012Publication date: August 1, 2013Applicant: GREENYUG, LLCInventors: Sagar B. GADEWAR, Brian Christopher VICENTE, Robert Elliot NORTON, Michael Francis DOHERTY
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Patent number: 8455677Abstract: A methanol dehydrogenating catalyst used for production of methyl formate, which contains a copper-zinc-aluminum oxide, a phosphoric acid compound, and an alkali metal bromide, wherein the catalyst has high methyl formate selectivity and excellent durability and heat resistance; and a method of producing methyl formate by using the catalyst.Type: GrantFiled: September 14, 2009Date of Patent: June 4, 2013Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kenji Nakamura, Hideaki Ogino, Yoriko Obata
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Publication number: 20120178962Abstract: A process for the production of high purity ethyl acetate from ethanol is described. The process involves reacting ethanol over a suitable catalyst in a reactive distillation column. The reactive distillation setup allows overcoming the reaction equilibrium for increased conversion of ethanol. Hydrogen is removed as the distillate and ethyl acetate is obtained as a bottoms product from the reactive distillation column. A feed of hydrogen at the bottom of the column and a suitable hydrogenation catalyst placed at the bottom of the column allows for a significant reduction of impurities such as butan-2-one and/or n-butyraldehyde in the ethyl acetate product. Adding side reactors to the reactive distillation column allows additional catalyst holdup for improved reactant conversion.Type: ApplicationFiled: March 16, 2012Publication date: July 12, 2012Applicant: GREENYUG, LLCInventor: Sagar B. GADEWAR
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Publication number: 20120035390Abstract: A process for the production of high purity ethyl acetate from ethanol is described. The process involves reacting ethanol over a suitable catalyst in a reactive distillation column. The reactive distillation setup allows overcoming the reaction equilibrium for increased conversion of ethanol. Hydrogen is removed as the distillate and ethyl acetate is obtained as a bottoms product from the reactive distillation column. A feed of hydrogen at the bottom of the column and a suitable hydrogenation catalyst placed at the bottom of the column allows for a significant reduction of impurities such as butan-2-one, butyraldehyde in the ethyl acetate product. Adding side reactors to the reactive distillation column allows additional catalyst holdup for improved reactant conversion.Type: ApplicationFiled: October 20, 2010Publication date: February 9, 2012Inventor: Sagar B. Gadewar
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Patent number: 8058481Abstract: Described is a process for the alkoxylation of alcohols with I, Cl, or CH3CO2 endgroups, using alkylene epoxides in the presence of boron based catalysts.Type: GrantFiled: April 30, 2009Date of Patent: November 15, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Kenneth Gene Moloy, James A. Schultz
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Publication number: 20110245532Abstract: A methanol dehydrogenating catalyst used for production of methyl formate, which contains a copper-zinc-aluminum oxide, a phosphoric acid compound, and an alkali metal bromide, wherein the catalyst has high methyl formate selectivity and excellent durability and heat resistance; and a method of producing methyl formate by using the catalyst.Type: ApplicationFiled: September 14, 2009Publication date: October 6, 2011Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Kenji Nakamura, Hideaki Ogino, Yoriko Obata
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Publication number: 20110152570Abstract: The present invention relates to processes for the production of sterically hindered diol ethers and diacyl ethers of formulaType: ApplicationFiled: August 26, 2010Publication date: June 23, 2011Applicant: The Research Foundation of State University of New YorkInventors: Robert L. Brainard, Brian Cardineau
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Publication number: 20100187472Abstract: A method is disclosed for the recovery of an organic acid from a dilute salt solution in which the cation of the salt forms an insoluble carbonate salt. A tertiary amine and CO2 are introduced to the solution to form the insoluble carbonate salt and a complex between the acid and an amine. A water immiscible solvent, such as an alcohol, is added to extract the acid/amine complex from the dilute salt solution to a reaction phase. The reaction phase is continuously dried and a product between the acid and the solvent, such as an ester, is formed.Type: ApplicationFiled: August 26, 2009Publication date: July 29, 2010Applicant: ZeaChem, Inc.Inventors: Dan W. Verser, Timothy J. Eggeman
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Patent number: 7355066Abstract: A process for making terpene esters is disclosed. Reaction of a terpene alcohol with acetic anhydride in the presence of a high-boiling amine provides a terpene ester. Acetic acid, which is distilled from the reaction mixture as it forms can be recovered. The terpene ester is distilled from the high-boiling amine to provide a product that is substantially free of nitrogen-containing impurities. The reaction mixture can be reused for subsequent acylations. The simple, economical process gives high-quality terpene esters while avoiding waste-disposal issues of other common acylation procedures.Type: GrantFiled: December 4, 2006Date of Patent: April 8, 2008Assignee: Millenium Specialty Chemicals, Inc.Inventors: Walter E. Johnson, C. Rodney Gorman
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Patent number: 7199263Abstract: A method of co-producing acetic anhydride and an acetate ester includes pyrolizing acetic acid at elevated temperature to produce a first ketene stream, the first ketene stream being a vapor phase stream comprising ketene, acetic acid and water; cooling the first ketene stream to condense acetic acid and water therefrom, thereby generating (i) a weak acid aqueous stream and (ii) a ketene feed stream; feeding the ketene feed stream to an acetic anhydride reactor where the ketene is reacted with acetic acid to produce acetic anhydride; concurrently with step (c), feeding the weak acid aqueous stream to an esterification reactor wherein acetic acid in the weak acid stream is reacted with an organic alcohol to produce an acetate ester.Type: GrantFiled: August 18, 2004Date of Patent: April 3, 2007Assignee: Celanese International CorporationInventor: R. Jay Warner
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Patent number: 7183421Abstract: The present invention provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound thereon and an oxidative catalyst thereon, and oxidizing the alcohol compound in the presence of an oxidizing agent, giving an oxide higher in oxidizing degree than the alcohol compound, and also provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound, and subjecting the alcohol compound to an electrolytic oxidation, giving an oxide higher in oxidizing degree than the alcohol compound.Type: GrantFiled: August 11, 2004Date of Patent: February 27, 2007Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Hideo Tanaka, Yutaka Kameyama
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Patent number: 7160524Abstract: The invention relates to an apparatus for the production of butylacetate by esterification of acetic acid with butanol in the presence of a solid acidic catalyst in which distillatory separation of components runs simultaneously with esterification. Thus, acetic acid and butanol are introduced in defined amounts and in the molar ratio 1:1 to 1:10 into a system, in which the reaction and the distillatory separation proceeds in three zones. The reaction together with distillatory separation of the components with different boiling points run in the reaction zone, while only distillation takes place in lower and upper separation zones. A volatile mixture is separated in the upper separation zone, from which, after being cooled at 5 to 80° C., water and organic phases are separated, the latest being refluxed into the system. The ratio of the feed amount to the organic phase reflux amount is 1:1 to 1:20, the reflux amount representing 60 to 100% of the whole amount of the organic phase.Type: GrantFiled: July 15, 2002Date of Patent: January 9, 2007Assignees: Sulzer Chemtech AG, Chemopetrol, a.s.Inventors: Jaromír Lederer, Jirí Kolena, Jirí Hanika, Pavel Morávek, Quido Smejkal, Vladimír Macek, Willem Levering, Oliver Bailer
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Patent number: 7091155Abstract: A catalyst for ester production which comprises zirconium oxide, copper, and at least one oxide selected from the group consisting of zinc oxide, chromium oxide, aluminum oxide and silicon oxide, and is obtainable by reducing with hydrogen a catalyst precursor prepared by the reaction of a salt containing at least one of metals constituting the oxides, a zirconium salt and a copper salt with an alkali hydroxide; and a process for producing an ester which comprises bringing either an alcohol or an alcohol and an aldehyde into contact with this catalyst in a gas phase.Type: GrantFiled: November 15, 2002Date of Patent: August 15, 2006Assignee: Chisso CorporationInventors: Kanichiro Inui, Takayoshi Takahashi, Toru Kurabayashi
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Patent number: 6867164Abstract: An acetic acid production catalyst that contains (b) at least one element selected from the group consisting of Group 14 elements, Group 15 elements and Group 16 elements of the Periodic Table and/or (c) at least one element selected from the group consisting of Group 6 elements, Group 7 elements, Group 8 elements, Group 9 elements, Group 10 elements, Group 11 elements and Group 12 elements of the Periodic Table, added to a palladium-loaded catalyst, as well as an acetic acid and ethyl acetate production catalyst that contains (b) at least one compound selected from the group consisting of inorganic acids and salts thereof and/or (c) at least one element selected from the group consisting of Group 14 elements, Group 15 elements and Group 16 elements of the Periodic Table and/or (d) at least one element selected from the group consisting of Group 6 elements, Group 7 elements, Group 8 elements, Group 9 elements, Group 10 elements, Group 11 elements and Group 12 elements of the Periodic Table, added to palladiumType: GrantFiled: September 17, 2002Date of Patent: March 15, 2005Assignee: Showa Denko K.K.Inventors: Yoshiaki Obana, Hiroshi Uchida, Ken-ichi Sano
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Patent number: 6809217Abstract: Ethanol is dehydrogenated in the presence of hydrogen over a dehydrogenation catalyst, for example, a copper on silica catalyst. The liquefiable products present in the resulting intermediate reaction product mixture are selectively hydrogenated over a suitable catalyst, such as 5% ruthenium on carbon, so as selectively to hydrogenate reactive carbonyl-containing by-products to the corresponding alcohols. Butan-2-one and n-butyraldehyde are thereby hydrogenated to 2-butanol and n-butanol respectively. A two stage distillation procedure is then used to purify the selectively hydrogenated product. A first distillate of ethyl acetate, ethanol and water produced in the first distillation zone is redistilled in the second distillation zone, thereby producing a bottom product comprising, typically, from about 99.8 mol % to about 99.Type: GrantFiled: June 5, 2001Date of Patent: October 26, 2004Assignee: Davy Process Technology LimitedInventors: Stephen William Colley, Christopher Richard Fawcett, Colin Rathmell, Michael William Marshall Tuck
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Patent number: 6797830Abstract: The present invention provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound thereon and an oxidative catalyst thereon, and oxidizing the alcohol compound in the presence of an oxidizing agent, giving an oxide higher in oxidizing degree than the alcohol compound, and also provides a process for producing an oxide from an alcohol compound, the process comprising the steps of causing silica gel to carry the alcohol compound, and subjecting the alcohol compound to an electrolytic oxidation, giving an oxide higher in oxidizing degree than the alcohol compound.Type: GrantFiled: November 28, 2001Date of Patent: September 28, 2004Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Hideo Tanaka, Yutaka Kameyama
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Patent number: 6740785Abstract: Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.Type: GrantFiled: July 26, 2002Date of Patent: May 25, 2004Assignee: The University of KansasInventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
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Patent number: 6639091Abstract: Bidentate ligand of formula II, R1R2M1—R—M2R3R4 (II) wherein M1 and M2 are independently P, As or Sb; R1, R2, R3 and R4 independently represent tertiary alkyl groups, or R1 and R2 together and/or R3 and R4 together represent an optionally substituted bivalent cycloaliphatic group whereby the two free valencies are linked to M1 or M2, and R represents a bivalent aliphatic bridging group containing from 2 to 6 atoms in the bridge, which is substituted with two or more substituents. A catalyst system comprising: a) a source of group VIII metal cations; b) a source of such a bidentate ligand; and c) a source of anions, and use of such a catalyst system in a process for the carbonylation of optionally substituted ethylenically or acetylenically unsaturated compounds by reaction with carbon monoxide and a coreactant is provided.Type: GrantFiled: May 17, 2001Date of Patent: October 28, 2003Assignee: Shell Oil CompanyInventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
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Patent number: 6521784Abstract: Methanol is reacted in presence of catalyst system comprising of an iron containing compound and a tin containing compound with or without an organic compound containing C, N, O, P, S, diamine, diketone, and or diphosphines as a ligand to produce acetic acid or methyl acetate. The reaction is effected in a solvent containing nitro or nitrite group.Type: GrantFiled: January 30, 2001Date of Patent: February 18, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Ashutosh Anant Kelkar, Sunil Sopana Tonde, Sunil Sadashiv Divekar, Raghunath Vitthal Chaudhari
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Patent number: 6458992Abstract: The invention relates to a process of butylacetate production by esterification of acetic acid with butanol in the presence of a solid acidic catalyst in which distillatory separation of components runs simultaneously with esterification. Thus, acetic acid and butanol are introduced in defined amounts and in the molar ratio 1:1 to 1:10 into a system, in which the reaction and the distillatory separation proceeds in three zones. The reaction together with distillatory separation of the components with different boiling points run in the reaction zone, while only distillation takes place in lower and upper separation zones. A volatile mixture is separated in the upper separation zone, from which, after being cooled at 5 to 80° C., water and organic phases are separated, the latest being refluxed into the system. The ratio of the feed amount to the organic phase reflux amount is 1:1 to 1:20, the reflux amount representing 60 to 100% of the whole amount of the organic phase.Type: GrantFiled: December 6, 2000Date of Patent: October 1, 2002Assignees: Sulzer Chemtech AG, Chemopetrol, A.S.Inventors: Jaromír Lederer, Ji{haeck over (r)}í Kolena, Ji{haeck over (r)}í Hanika, Willem Wiekert Levering, Oliver Bailer, Pavel Morävek, Quido Smejkal, Vladimír Macek
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Publication number: 20020128506Abstract: A method of oxidizing an organic alcohol, wherein the organic alcohol is contacted with a stoichiometric excess of oxygen in the presence of an effective catalytic amount of a manganese-containing octahedral molecular sieve or octahedral layer. Primary alcohols are selectively oxidized to aldehydes, and secondary alcohols are selectively oxidized to ketones.Type: ApplicationFiled: August 14, 2001Publication date: September 12, 2002Inventors: Steven L. Suib, Young Chan Son, Amy R. Howell
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Patent number: 6444842Abstract: The present invention provides an improved method for the preparation of carboxylic acid esters of alkylene glycol monoalkyl ethers by the acid catalyzed esterification of the monoalkyl ether with a carboxylic acid. In a preferred embodiment of the invention, the carboxylic acid and alcohol are reacted in a reactor/column and the resulting ester product is distilled into an overhead decanter/extractor as a single phase. A small amount of solvent, preferably a hydrocarbon is added to the mixture causing the resulting distillate to separate into two phases, one phase containing the desired product, the other containing primarily water. The process described is applicable to both batch and continuous operation and is not constrained by the difficulty of separating closely boiling azeotropes and results in substantially higher production rates than achieved by current processes.Type: GrantFiled: April 19, 2000Date of Patent: September 3, 2002Assignee: Celanese International CorporationInventors: H. Robert Gerberich, R. Jay Warner
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Patent number: 6399828Abstract: A process for making compound of formula I from a phenylpropanolamine salt of formula II wherein: R1 is hydrogen or a lower alkyl group; each R2 is independently a hydrogen, halogen, lower alkyl group, lower alkoxy groups, lower alkyl group substituted with 1 to 5 halogens, lower alkoxy groups substituted with 1 to 5 halogens, or both R2 together when on adjacent carbons constitute a —O(CH2)xO— where x is 1 to 4, thereby forming a ring structure fused with the phenyl group; R3 is a C1-C8-alkyl group, a C1-C12-aralkyl group, C1-C12-alkaryl group, or a phenyl group, each optionally substituted by 1 to 5 substituents selected from halogen, hydroxy, or C1-C6-alkyl; and HX is an equivalent of an organic or inorganic acid, the process comprising: (a) acylating the phenylpropanolamine salt of formula II with an acylating agent in a solvent at elevated temperature to make a reaction mixture containing an O-acylated phenylpropanolamine salt of formula III which canType: GrantFiled: October 29, 2001Date of Patent: June 4, 2002Assignee: Boehringer Ingelheim Chemicals, Inc.Inventors: Robert Frederick Boswell, Young Sek Lo
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Publication number: 20020002289Abstract: The present invention provides a method for producing a carbonyl compound by dehydrogenating an alcohol. Namely, it relates to a method for producing a carbonyl compound, which comprises dehydrogenating an alcohol in the presence of a complex compound catalyst comprising ruthenium and an organic phosphine wherein aliphatic carbons are bonded to two or more of the three bonding hands of the phosphorus atom.Type: ApplicationFiled: August 21, 2001Publication date: January 3, 2002Applicant: MITSUBISHI CHEMICAL CORPORATIONInventors: Masaru Utsunomiya, Kazunari Takahashi, Yoko Seto, Souichi Orita, Souichi Amano
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Patent number: 6316664Abstract: Formic ester is transesterified with a hydroxyl-containing compound in the presence of a tertiary amine as transesterification catalyst to form a formic ester which differs from the formic ester used as reactant, and of a hydroxyl-containing compound which is different from the hydroxyl-containing compound used as reactant.Type: GrantFiled: May 8, 1998Date of Patent: November 13, 2001Assignee: BASF AktiengesellschaftInventors: Detlef Kratz, Christoph Sigwart
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Patent number: 6278015Abstract: The present invention provides a process for preparing esters or thioesters of trifluoroacetic acid from trifluoroacetyl chloride and an alcohol or a thiol with the ester or thioester being present as the solvent. Esters and thioesters of trifluoroacetic acid are fine chemical intermediates which can be used in the manufacture of pharmaceuticals, agricultural chemicals, liquid crystals, dyes and industrial chemicals. Trifluoroacetate esters and thioesters can also be used as solvents in the manufacture of other fine chemicals, pharmaceuticals, agricultural chemicals, liquid crystals, industrial chemicals and dyes.Type: GrantFiled: July 17, 2000Date of Patent: August 21, 2001Assignee: Rohm and Haas CompanyInventors: Lori Ann Spangler, Fereydon Abdesaken, Joshua Anthony Chong
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Patent number: 6093845Abstract: This invention relates to a process for the simultaneous co-production of ethyl acetate and n-butyl acetate. The process involves reacting a reaction mixture of ethanol, n-butanol and acetic acid in the liquid phase, in the presence of an acidic catalyst. The process is carried out in a series of reactor and distillation columns. The process is capable of using relatively impure reactants and provides for removing some of the aldehyde type impurities by the use of resin guard beds.Type: GrantFiled: November 25, 1998Date of Patent: July 25, 2000Assignee: BP Chemicals LimitedInventors: Patrick Eduard van Acker, Olivier Mathieu, Russell James Milner, Witold Franciszek Pacynko
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Patent number: 6072077Abstract: 5-Z-octenyl esters of the formula ##STR1## in which R represents hydrogen, methyl or ethyl, have an intensive mango aroma, so that the compounds I can be added to fruit compositions and aroma compositions; they have flavor-intensifying and flavor-rounding action.Type: GrantFiled: June 5, 1997Date of Patent: June 6, 2000Assignee: Haarmann & Reimer, GmbHInventors: Heinz-Jurgen Bertram, Matthias Guntert, Gunter Kindel
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Patent number: 5998658Abstract: An improved process for the preparation of acetic esters is disclosed. It comprises a fixed bed reaction and a catalytic distillation. The fixed bed reaction comprises the steps of: (a) charging acetic acid and alcohol into a fixed bed reactor under a predetermined reaction condition; and (b) reacting the esterification reactants in the fixed bed reactor. The fixed bed reactor contains acidic catalysts that are present in a solid phase, and the reaction condition is controlled such that (i) the reactants and the products co-exist in a gas-liquid two-phase equilibrium in the fixed bed reactor and that (ii) at least one component of the reactants is present in one phase and at least one component of the products is present in another phase.Type: GrantFiled: June 26, 1998Date of Patent: December 7, 1999Assignee: Industrial Technology Research InstituteInventors: Kuo-Ching Wu, Ching-Tang Lin
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Patent number: 5981792Abstract: The process for preparing 1-functional allyl alcohol carboxylic esters comprises reacting a 3-functional allyl alcohol with the anhydride of the carboxylic acid at temperatures above 100.degree. C. in the presence of metal compounds of transition groups V to VII, namely at temperatures of 100-200.degree. C., preferably 130-150.degree. C. As metal compounds, it is possible to use oxidic metal compounds in the highest or at least second highest oxidation state of the transition metals, for example tungstic acid or its salts and/or tungsten(VI) oxide and/or molybdenum(V) oxide and/or molybdenum(VI) oxide and/or rhenium(VII) oxide. The 3-functional allyl alcohol and the carboxylic anhydride are advantageously used in equimolar amounts, if desired with a slight excess of anhydride, and an alkali metal salt of a weak acid, for example sodium carbonate or sodium acetate, can be added to the reaction mixture in an amount sufficient to trap free protons.Type: GrantFiled: February 26, 1998Date of Patent: November 9, 1999Assignee: Dragoco Gerberding & Co. AGInventor: Jurgen Vollhardt
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Patent number: 5977402Abstract: 4-tert.-Butylcyclohexanol having a larger content of its cis-isomer is prepared by hydrogenating 4-tert.-butylphenol in a solvent in the presence of a rhodium catalyst and a compound selected from the group consisting of hydrogen chloride and (anhydrous) sulfuric acid. Furthermore, 4-tert.-butylcyclohexanol obtained by the above hydrogenation is acetylated to give 4-tert.-butylcyclohexyl acetate.Type: GrantFiled: April 22, 1998Date of Patent: November 2, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Masahito Sekiguchi, Shin Tanaka
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Patent number: 5900369Abstract: Optically active oxodicyclopentadiene is produced by adding lipase into ketoalcohol (1) and vinyl acetate, stirring them to obtain optically active acetate, and methylating and oxidizing to cleavage the reactant, and treating the product under basic conditions.Type: GrantFiled: July 8, 1998Date of Patent: May 4, 1999Assignee: Chisso CorporationInventors: Kunio Ogasawara, Takahiko Taniguchi
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Patent number: 5869739Abstract: Formic acid or derivatives thereof are produced from non-toxic carbon dioxide in the supercritical state, using it as raw materials, without using solvents, and at a high efficiency owing to a high reaction velocity, by reacting said carbon dioxide and an active hydrogen group-containing compound.Type: GrantFiled: November 20, 1996Date of Patent: February 9, 1999Assignees: Research Development Corporation of Japan, NKK CorporationInventors: Takao Ikariya, Philip Gregory Jessop, Yi Hsiao, Ryoji Noyori
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Patent number: 5840962Abstract: A process for preparing an ester comprising reacting an alcohol with a ketene in an ester solvent in the presence of an acid catalyst, resulting in a high yield of the ester product, with a minimum of byproducts.Type: GrantFiled: February 17, 1995Date of Patent: November 24, 1998Assignee: Industrias Monfel S.A. De C.V.Inventors: Michel Cohen, Mikhail Khramov
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Patent number: 5831116Abstract: A process for partially oxidizing alcohols such as methanol, comprising the steps of a) introducing into a reactor unit containing a solid acid catalyst amounts of alcohol and oxygen; and a supercritical fluid (such as SCF CO.sub.2) mobile phase; and b) partially oxidizing the alcohol to its corresponding ether, aldehyde, ester or acid. In an advantageous embodiment, methanol is oxidized using an aerogel acid catalyst to produce methyl ether.Type: GrantFiled: April 18, 1997Date of Patent: November 3, 1998Assignee: Northeastern UniversityInventors: Chien-Tsung Wang, Ronald J. Willey