Preparing Esters By Dehydrogenation Of Alcohols Patents (Class 560/239)
  • Patent number: 11506620
    Abstract: 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: Grant
    Filed: July 16, 2019
    Date of Patent: November 22, 2022
    Assignee: United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Kevin Righter
  • Patent number: 10279984
    Abstract: 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: Grant
    Filed: February 18, 2013
    Date of Patent: May 7, 2019
    Assignee: ILLYCAFFE' S.P.A.
    Inventors: Luca Mastropasqua, Angelo Dori, Stefano Santagiuliana, Giuseppe Cutuli, Gaia Brollo, Furio Suggi Liverani, Gianluca Giamba
  • Patent number: 10077226
    Abstract: 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: Grant
    Filed: October 17, 2016
    Date of Patent: September 18, 2018
    Assignee: Archer-Daniels-Midland Company
    Inventors: Eric L. Dias, Vincent J. Murphy, James A. W. Shoemaker
  • Patent number: 9790164
    Abstract: 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: Grant
    Filed: May 7, 2014
    Date of Patent: October 17, 2017
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Fabrice Aquino, Johannes Tschumi
  • Patent number: 9000212
    Abstract: 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: Grant
    Filed: April 18, 2012
    Date of Patent: April 7, 2015
    Assignee: Takasago International Corporation
    Inventors: Taichiro Touge, Kunimori Aoki, Hideki Nara, Wataru Kuriyama
  • Publication number: 20140243519
    Abstract: 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: Application
    Filed: August 16, 2012
    Publication date: August 28, 2014
    Inventors: Nobuyoshi Yasuda, Jeffrey T. Kuethe, Guy Humphrey, Gregory L. Beutner, Yong-Li Zhong, Edward Cleator, Carl Baxter
  • Publication number: 20140235890
    Abstract: 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: Application
    Filed: April 1, 2014
    Publication date: August 21, 2014
    Applicant: BASF Corporation
    Inventors: Rostam Jai Madon, Peter Nagel, Deepak S. Thakur
  • Publication number: 20140142013
    Abstract: 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: Application
    Filed: November 20, 2012
    Publication date: May 22, 2014
    Applicant: Chervon U.S.A. Inc.
    Inventor: Saleh Ali Elomari
  • Patent number: 8703994
    Abstract: 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: Grant
    Filed: July 26, 2012
    Date of Patent: April 22, 2014
    Assignee: BASF SE
    Inventors: Thomas Schaub, Rocco Paciello, Marek Pazicky, Giuseppe Fachinetti, Debora Preti
  • Publication number: 20140024854
    Abstract: 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: Application
    Filed: July 17, 2013
    Publication date: January 23, 2014
    Inventors: Thomas Schaub, Stefan Rüdenauer, Daniel Schneider, Rocco Paciello
  • Publication number: 20140012037
    Abstract: 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: Application
    Filed: September 10, 2013
    Publication date: January 9, 2014
    Inventors: Sagar B. Gadewar, Peter K. Stoimenov
  • Publication number: 20130296603
    Abstract: Dehydrogenative coupling can be achieved in nearly quantitative conversions and yields using a membrane reactor.
    Type: Application
    Filed: May 3, 2013
    Publication date: November 7, 2013
    Applicant: KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY
    Inventor: KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY
  • Publication number: 20130281664
    Abstract: 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: Application
    Filed: October 11, 2011
    Publication date: October 24, 2013
    Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
  • Patent number: 8562921
    Abstract: 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: Grant
    Filed: March 16, 2012
    Date of Patent: October 22, 2013
    Assignee: Greenyug, LLC.
    Inventor: Sagar B. Gadewar
  • Patent number: 8558025
    Abstract: 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: Grant
    Filed: October 20, 2010
    Date of Patent: October 15, 2013
    Assignee: Greenyug, LLC
    Inventor: Sagar B Gadewar
  • Publication number: 20130197266
    Abstract: 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: Application
    Filed: February 1, 2012
    Publication date: August 1, 2013
    Applicant: GREENYUG, LLC
    Inventors: Sagar B. GADEWAR, Brian Christopher VICENTE, Robert Elliot NORTON, Michael Francis DOHERTY
  • Patent number: 8455677
    Abstract: 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: Grant
    Filed: September 14, 2009
    Date of Patent: June 4, 2013
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kenji Nakamura, Hideaki Ogino, Yoriko Obata
  • Publication number: 20120178962
    Abstract: 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: Application
    Filed: March 16, 2012
    Publication date: July 12, 2012
    Applicant: GREENYUG, LLC
    Inventor: Sagar B. GADEWAR
  • Publication number: 20120035390
    Abstract: 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: Application
    Filed: October 20, 2010
    Publication date: February 9, 2012
    Inventor: Sagar B. Gadewar
  • Patent number: 8058481
    Abstract: 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: Grant
    Filed: April 30, 2009
    Date of Patent: November 15, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Kenneth Gene Moloy, James A. Schultz
  • Publication number: 20110245532
    Abstract: 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: Application
    Filed: September 14, 2009
    Publication date: October 6, 2011
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Kenji Nakamura, Hideaki Ogino, Yoriko Obata
  • Publication number: 20110152570
    Abstract: The present invention relates to processes for the production of sterically hindered diol ethers and diacyl ethers of formula
    Type: Application
    Filed: August 26, 2010
    Publication date: June 23, 2011
    Applicant: The Research Foundation of State University of New York
    Inventors: Robert L. Brainard, Brian Cardineau
  • Publication number: 20100187472
    Abstract: 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: Application
    Filed: August 26, 2009
    Publication date: July 29, 2010
    Applicant: ZeaChem, Inc.
    Inventors: Dan W. Verser, Timothy J. Eggeman
  • Patent number: 7355066
    Abstract: 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: Grant
    Filed: December 4, 2006
    Date of Patent: April 8, 2008
    Assignee: Millenium Specialty Chemicals, Inc.
    Inventors: Walter E. Johnson, C. Rodney Gorman
  • Patent number: 7199263
    Abstract: 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: Grant
    Filed: August 18, 2004
    Date of Patent: April 3, 2007
    Assignee: Celanese International Corporation
    Inventor: R. Jay Warner
  • Patent number: 7183421
    Abstract: 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: Grant
    Filed: August 11, 2004
    Date of Patent: February 27, 2007
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Hideo Tanaka, Yutaka Kameyama
  • Patent number: 7160524
    Abstract: 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: Grant
    Filed: July 15, 2002
    Date of Patent: January 9, 2007
    Assignees: Sulzer Chemtech AG, Chemopetrol, a.s.
    Inventors: Jaromír Lederer, Jirí Kolena, Jirí Hanika, Pavel Morávek, Quido Smejkal, Vladimír Macek, Willem Levering, Oliver Bailer
  • Patent number: 7091155
    Abstract: 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: Grant
    Filed: November 15, 2002
    Date of Patent: August 15, 2006
    Assignee: Chisso Corporation
    Inventors: Kanichiro Inui, Takayoshi Takahashi, Toru Kurabayashi
  • Patent number: 6867164
    Abstract: 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 palladium
    Type: Grant
    Filed: September 17, 2002
    Date of Patent: March 15, 2005
    Assignee: Showa Denko K.K.
    Inventors: Yoshiaki Obana, Hiroshi Uchida, Ken-ichi Sano
  • Patent number: 6809217
    Abstract: 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: Grant
    Filed: June 5, 2001
    Date of Patent: October 26, 2004
    Assignee: Davy Process Technology Limited
    Inventors: Stephen William Colley, Christopher Richard Fawcett, Colin Rathmell, Michael William Marshall Tuck
  • Patent number: 6797830
    Abstract: 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: Grant
    Filed: November 28, 2001
    Date of Patent: September 28, 2004
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Hideo Tanaka, Yutaka Kameyama
  • Patent number: 6740785
    Abstract: 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: Grant
    Filed: July 26, 2002
    Date of Patent: May 25, 2004
    Assignee: The University of Kansas
    Inventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
  • Patent number: 6639091
    Abstract: 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: Grant
    Filed: May 17, 2001
    Date of Patent: October 28, 2003
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
  • Patent number: 6521784
    Abstract: 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: Grant
    Filed: January 30, 2001
    Date of Patent: February 18, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Ashutosh Anant Kelkar, Sunil Sopana Tonde, Sunil Sadashiv Divekar, Raghunath Vitthal Chaudhari
  • Patent number: 6458992
    Abstract: 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: Grant
    Filed: December 6, 2000
    Date of Patent: October 1, 2002
    Assignees: 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
  • Publication number: 20020128506
    Abstract: 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: Application
    Filed: August 14, 2001
    Publication date: September 12, 2002
    Inventors: Steven L. Suib, Young Chan Son, Amy R. Howell
  • Patent number: 6444842
    Abstract: 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: Grant
    Filed: April 19, 2000
    Date of Patent: September 3, 2002
    Assignee: Celanese International Corporation
    Inventors: H. Robert Gerberich, R. Jay Warner
  • Patent number: 6399828
    Abstract: 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 can
    Type: Grant
    Filed: October 29, 2001
    Date of Patent: June 4, 2002
    Assignee: Boehringer Ingelheim Chemicals, Inc.
    Inventors: Robert Frederick Boswell, Young Sek Lo
  • Publication number: 20020002289
    Abstract: 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: Application
    Filed: August 21, 2001
    Publication date: January 3, 2002
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Masaru Utsunomiya, Kazunari Takahashi, Yoko Seto, Souichi Orita, Souichi Amano
  • Patent number: 6316664
    Abstract: 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: Grant
    Filed: May 8, 1998
    Date of Patent: November 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Detlef Kratz, Christoph Sigwart
  • Patent number: 6278015
    Abstract: 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: Grant
    Filed: July 17, 2000
    Date of Patent: August 21, 2001
    Assignee: Rohm and Haas Company
    Inventors: Lori Ann Spangler, Fereydon Abdesaken, Joshua Anthony Chong
  • Patent number: 6093845
    Abstract: 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: Grant
    Filed: November 25, 1998
    Date of Patent: July 25, 2000
    Assignee: BP Chemicals Limited
    Inventors: Patrick Eduard van Acker, Olivier Mathieu, Russell James Milner, Witold Franciszek Pacynko
  • Patent number: 6072077
    Abstract: 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: Grant
    Filed: June 5, 1997
    Date of Patent: June 6, 2000
    Assignee: Haarmann & Reimer, GmbH
    Inventors: Heinz-Jurgen Bertram, Matthias Guntert, Gunter Kindel
  • Patent number: 5998658
    Abstract: 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: Grant
    Filed: June 26, 1998
    Date of Patent: December 7, 1999
    Assignee: Industrial Technology Research Institute
    Inventors: Kuo-Ching Wu, Ching-Tang Lin
  • Patent number: 5981792
    Abstract: 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: Grant
    Filed: February 26, 1998
    Date of Patent: November 9, 1999
    Assignee: Dragoco Gerberding & Co. AG
    Inventor: Jurgen Vollhardt
  • Patent number: 5977402
    Abstract: 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: Grant
    Filed: April 22, 1998
    Date of Patent: November 2, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahito Sekiguchi, Shin Tanaka
  • Patent number: 5900369
    Abstract: 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: Grant
    Filed: July 8, 1998
    Date of Patent: May 4, 1999
    Assignee: Chisso Corporation
    Inventors: Kunio Ogasawara, Takahiko Taniguchi
  • Patent number: 5869739
    Abstract: 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: Grant
    Filed: November 20, 1996
    Date of Patent: February 9, 1999
    Assignees: Research Development Corporation of Japan, NKK Corporation
    Inventors: Takao Ikariya, Philip Gregory Jessop, Yi Hsiao, Ryoji Noyori
  • Patent number: 5840962
    Abstract: 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: Grant
    Filed: February 17, 1995
    Date of Patent: November 24, 1998
    Assignee: Industrias Monfel S.A. De C.V.
    Inventors: Michel Cohen, Mikhail Khramov
  • Patent number: 5831116
    Abstract: 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: Grant
    Filed: April 18, 1997
    Date of Patent: November 3, 1998
    Assignee: Northeastern University
    Inventors: Chien-Tsung Wang, Ronald J. Willey