Of Alcohol Or Alcoholate Patents (Class 562/519)
  • Publication number: 20090082593
    Abstract: A process produces acetic acid by continuously carrying out a reaction of methanol with carbon monoxide in the presence of a Group VIII metal catalyst, an iodide salt, methyl iodide, and water in a reactor, continuously withdrawing a reaction mixture from the reactor, introducing the reaction mixture into an evaporation process at a pressure lower than that in the reaction to separate the reaction mixture into low-boiling components and high-boiling components containing the Group VIII metal and the iodide salt, and recycling the separated high-boiling components containing the Group VIII metal and the iodide salt to the reactor, in which the separated high-boiling components are brought into contact with hydrogen at temperatures of 80° C. or higher for 6 seconds or longer before the high-boiling components reaching the reactor, which hydrogen is introduced in an amount of 0.1 time by mole or more that of the Group VIII metal.
    Type: Application
    Filed: September 26, 2006
    Publication date: March 26, 2009
    Inventor: Hidetaka Kojima
  • Patent number: 7491842
    Abstract: A carbonylation process for producing a carbonylation product by contacting carbon monoxide with a feed comprising an alcohol and/or a reactive derivative thereof in the vapour phase using an heterogeneous heteropolyacid catalyst comprising one or more metal cations selected from Cu, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and Pt and wherein there is at least 0.5 wt % water present in the feed.
    Type: Grant
    Filed: February 9, 2005
    Date of Patent: February 17, 2009
    Assignee: BP Chemicals Limited
    Inventor: Warren John Smith
  • Publication number: 20090030229
    Abstract: A process for continuous carbonylation of carbonylatable reactants with carbon monoxide in the gaseous phase in the presence of a catalyst, wherein said catalyst is a Supported Ionic Liquid-Phase (SILP) catalyst comprising a solution of a Group VIII metal in an ionic liquid confined on a support. The SILP catalyst offers a very large active catalyst area resulting in a very efficient use of catalyst material and a simple apparatus design.
    Type: Application
    Filed: May 19, 2006
    Publication date: January 29, 2009
    Inventors: Anders Riisager, Rasmus Fehrmann
  • Patent number: 7476761
    Abstract: A process for producing a carboxylic acid comprises allowing an alcohol having a carbon number of “n” to continuously react with carbon monoxide in the presence of a carbonylation catalyst system, and a limited amount of water, continuously withdrawing the reaction mixture from the reaction system 1, introducing the withdrawn reaction mixture into a distillation step (distillation columns 3a and 3b), and separating a higher-boiling component and a lower-boiling component containing a carboxylic acid having a carbon number of “n+1”, respectively.
    Type: Grant
    Filed: December 14, 2005
    Date of Patent: January 13, 2009
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Hidetaka Kojima
  • Patent number: 7473800
    Abstract: Acetic acid is manufactured by carbonylating methanol with carbon monoxide by way of a heterogeneous catalytic reaction in a bubble column reactor. The carbonylating reaction is conducted with a solid catalyst concentration of not less than 100 kg/m3 in terms of the reaction volume. For the reaction, the partial pressure of carbon monoxide in the reactor is confined to a range between 1.0 and 2.5 MPa while the exhaustion ratio of carbon monoxide is confined to a range between 3 and 15% of the theoretical reaction volume of carbon monoxide and the liquid superficial velocity is made to be found in a range between 0.2 and 1.0 m/sec.
    Type: Grant
    Filed: March 11, 2004
    Date of Patent: January 6, 2009
    Assignee: Chiyoda Corporation
    Inventors: Yasuo Hosono, Tadashi Matsumoto, Rei Sato, Takeshi Minami, Chieko Nagasawa, Munenori Maekawa
  • Patent number: 7470811
    Abstract: An integrated process for making methanol, acetic acid, and a product from an associated process is disclosed. Syngas (120) is produced by combined steam reforming (109) and autothermal reforming (118) of natural gas (102) where a portion (112) of the natural gas bypasses the steam reformer (109) and is blended with the steam reformer effluent for supply to the autothermal reformer (ATR) (118) with CO2 recycle (110). A portion of the syngas is fed to CO2 removal (122) to obtain the recycle CO2 and cold box (130) to obtain a hydrogen stream (131) and a CO stream (135). The remaining syngas, hydrogen stream (131) and CO2 from an associated process are fed to methanol synthesis (140), which produces methanol and a purge stream (124) supplied to the CO2 removal unit. The methanol is supplied to an acetic acid unit (13)6 with the CO (135) to make acetic acid, which in turn is supplied to a VAM synthesis unit (148).
    Type: Grant
    Filed: January 22, 2004
    Date of Patent: December 30, 2008
    Assignee: Acetex (Cyprus) Limited
    Inventor: Daniel Marcel Thiebaut
  • Publication number: 20080319223
    Abstract: A process for the production of acetic acid by carbonylating methanol and/or a reactive derivative thereof with carbon monoxide in the presence of a promoted iridium carbonylation catalyst wherein the promoters are boron and gallium.
    Type: Application
    Filed: January 10, 2007
    Publication date: December 25, 2008
    Inventors: Andrew John Miller, Marc John Payne
  • Publication number: 20080269519
    Abstract: A process and catalyst for the production of acetic acid by the carbonylation of methanol and/or a reactive derivative thereof wherein the catalyst system comprises a rhodium carbonylation catalyst, methyl iodide, a non-hydrohalogenoic acid promoter and optionally a co-promoter capable of generating ionic iodide.
    Type: Application
    Filed: November 17, 2005
    Publication date: October 30, 2008
    Inventors: Andrew John Miller, George Ernest Morris
  • Publication number: 20080269518
    Abstract: An apparatus and method for carbonylating a reactant, including sequestering Group VIII catalyst metal from a process stream which generally has a ppb concentration of the catalyst metal. The process stream is treated with a polymer having nitrogen-containing heterocyclic repeat units to sequester the catalyst from the stream, thus allowing valuable catalyst to be recovered and returned to the reaction mixture. An apparatus provides a resin bed downstream of the light ends column in a carbonylation process. Preferably, spent resin is regenerated with a regenerant composition compatible with the carbonylation reaction mixture so that catalyst metal can be directly recycled and the resin re-used.
    Type: Application
    Filed: April 25, 2007
    Publication date: October 30, 2008
    Inventors: Mark O. Scates, Joshua Gregory Wagner
  • Patent number: 7381837
    Abstract: A method comprises continuously supplying an alcohol to a pressurized reaction system, pressurizing carbon monoxide with a compressor 8 attached to a first feed line 22, for continuously supplying carbon monoxide to the reaction system via a second feed line 23 with a reference flow rate F, and converging excess carbon monoxide in the reaction system in the first feed line via a branched circulation line 24 for allowing to react alcohol with carbon monoxide. The reference flow rate F in the second feed line 23 is a total rate of a reference consumption flow rate Fcs in the reaction and a flow rate F1 in excess rate over a fluctuation consumption flow rate ?Fcv in the reaction system (F=Fcs+F1, F1>?Fcv).
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: June 3, 2008
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hidehiko Nakajima, Yoshiyuki Harano, Manabu Yamada
  • Patent number: 7368597
    Abstract: A process for the liquid phase carbonylation of an alcohol and/or a reactive derivative thereof in the presence of hydrogen in which there is employed a catalyst comprising rhodium of iridium coordinated with a polydentate ligand.
    Type: Grant
    Filed: May 5, 2004
    Date of Patent: May 6, 2008
    Assignee: BP Chemicals Limited
    Inventors: Sander Gaemers, John Glenn Sunley
  • Patent number: 7345197
    Abstract: A method for removing aldehyde impurities from acetic acid is disclosed. The method comprises extracting the aldehyde impurities from a methyl iodide solution such as the decanter heavy phase with a polyol. After the aldehyde impurities are removed, the methyl iodide heavy phase can be recycled to the carbonylation.
    Type: Grant
    Filed: June 5, 2007
    Date of Patent: March 18, 2008
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Noel C. Hallinan, Brian A. Salisbury
  • Patent number: 7342129
    Abstract: A process for the production of acetic acid by carbonylating methanol and/or a reactive derivative thereof with carbon monoxide in a carbonylation reactor containing a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide co-catalyst, a finite concentration of water, acetic acid, methyl acetate, at least one promoter selected from ruthenium, osmium and rhenium and a stablising compound selected from the group consisting of alkali metal iodides, alkaline earth metal iodides, metal complexes capable of generating I?, salts capable of generating I?, and mixtures of two or more thereof wherein the molar ratio of promoter to iridium is greater than 2:1, and the molar ratio of stabilising compound to iridium is in the range [greater than 0 to 5]:1.
    Type: Grant
    Filed: May 29, 2003
    Date of Patent: March 11, 2008
    Assignee: BP Chemicals Limited
    Inventors: David John Law, Andrew David Poole, Stephen James Smith, John Glenn Sunley
  • Patent number: 7335799
    Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: February 26, 2008
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Publication number: 20070293695
    Abstract: Disclosed is a carbonylation process for the production of carboxylic acids, carboxylic acid esters and/or carboxylic acid anhydrides wherein a carbonylation feedstock compound selected from one or more organic oxygenates such as alcohols, ethers, and esters is contacted with carbon monoxide in the presence of a carbonylation catalyst and one or more onium compounds. The carbonylation process differs from known carbonylation processes in that a halide compound such as a hydrogen halide, typically hydrogen iodide, and/or alkyl halide, typically methyl iodide, extraneous or exogenous to the carbonylation process is not fed or supplied separately to the process.
    Type: Application
    Filed: June 15, 2006
    Publication date: December 20, 2007
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Joseph Robert Zoeller, Mary Kathleen Moore, Andrew James Vetter
  • Publication number: 20070287862
    Abstract: Disclosed is a process for the production of acetic acid or mixtures of acetic acid and acetic anhydride in a carbonylation process wherein a mixture comprising methyl acetate and/or dimethyl ether and methyl iodide is contacting in the liquid phase with carbon monoxide in the presence of a carbonylation catalyst at elevated pressures and temperatures. Methanol, water, or a mixture thereof is added to an acetic anhydride-containing stream within a flash evaporation zone to convert some or all of the acetic anhydride to acetic acid and optionally methyl acetate and to provide heat for the evaporation of a portion of the product effluent produced by the carbonylation process.
    Type: Application
    Filed: June 9, 2006
    Publication date: December 13, 2007
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Robert Sterling Kline, Gregory Abbott Wellman, Jr., Brandon Tyler Earls, Jerry Lee Bewley
  • Patent number: 7276626
    Abstract: A process for the production of a carboxylic acid and/or the alcohol ester of a carboxylic acid by carbonylating an alcohol and/or a reactive derivative thereof with carbon monoxide employing as the carbonylation catalyst, cobalt, rhodium or iridium coordinated with a tridentate ligand.
    Type: Grant
    Filed: May 5, 2004
    Date of Patent: October 2, 2007
    Assignee: BP Chemicals Limited
    Inventors: Sander Gaemers, John Glenn Sunley
  • Patent number: 7265240
    Abstract: A process for the carbonylation of ethylenically unsaturated compounds is described. The process comprises reacting an ethylenically unsaturated compound with carbon monoxide in the presence of a source of hydroxyl groups and a catalyst system. The catalyst system is obtained by combining: (a) metal of Group VIII or a compound thereof; and (b) a bidentate phosphine of general formula (I) The carbonylation reaction is carried out at a temperature of between ?30° C. to 49° C. and under a CO partial pressure of less than 30×105 N.
    Type: Grant
    Filed: August 4, 2003
    Date of Patent: September 4, 2007
    Assignee: Lucite International UK Limited
    Inventors: Graham R. Eastham, Cristina Jimenez, David Cole-Hamilton
  • Patent number: 7256308
    Abstract: A process for the production of acetic acid by carbonylating methanol and/or a reactive derivative thereof in a carbonylation reactor in a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide, methyl acetate, water, acetic acid and at least one promoter selected from the group consisting of ruthenium, rhenium and osmium, characterized in that there is also present in the reaction composition a bis-phosphonate compound having the formula (I): wherein R1, R2, R3, R4 are independently hydrogen or an organic functional group; Y is an optionally substituted C1-C10 alkylene or C6-C10 aryl group.
    Type: Grant
    Filed: May 29, 2003
    Date of Patent: August 14, 2007
    Assignee: BP Chemicals Limited
    Inventor: David John Law
  • Patent number: 7223886
    Abstract: An improvement of the methanol carbonylation process for manufacturing acetic acid is disclosed. Specifically disclosed is a method for reducing the formation of alkyl iodides and C3-8 carboxylic acids by removing permanganate reducing compounds (“PRC's”) from the light phase of the condensed light ends overhead stream, including (a) distilling the light phase to yield a PRC enriched overhead stream; and (b) extracting the third overhead stream with water in at least two consecutive stages and separating therefrom one or more aqueous streams containing PRC's.
    Type: Grant
    Filed: March 2, 2004
    Date of Patent: May 29, 2007
    Assignee: Celanese International Corporation
    Inventors: Mark O. Scates, David A. Trueba, Raymond J. Zinobile
  • Patent number: 7208624
    Abstract: An improved process is disclosed for producing acetic acid, including the following steps: reacting a carbonylatable reactant such as methanol, methyl acetate, methyl formate or dimethyl ether with carbon monoxide in a reaction medium containing water, methyl iodide, and a catalyst to produce a reaction product that contains acetic acid; separating the reaction product to provide a volatile phase containing acetic acid, water, and methyl iodide and a less volatile phase; distilling the volatile phase to produce a purified acetic acid product and a first overhead containing water, methyl acetate, and methyl iodide; phase separating the first overhead to provide a first liquid phase containing water and a second liquid phase containing methyl iodide; and adding dimethyl ether to the process in an amount effective to enhance separation of the first overhead to form the first and second liquid phases.
    Type: Grant
    Filed: March 2, 2004
    Date of Patent: April 24, 2007
    Assignee: Celanese International Corporation
    Inventors: Mark O. Scates, David A. Trueba
  • Patent number: 7202382
    Abstract: A process for the production of acetic acid which comprises carbonylating methanol and/or a reactive derivative thereof in one or more reactors in a liquid reaction composition comprising iridium carbonylation catalyst, ruthenium promoter, methyl iodide co-catalyst, methyl acetate, acetic acid and water. The liquid reaction composition from the one or more reactors is passed to one or more flash separation stages to form (i) a vapor fraction comprising condensable components and a low pressure off-gas comprising carbon monoxide and (ii) a liquid fraction comprising iridium carbonylation catalyst, ruthenium promoter and acetic acid solvent. The condensable components are separated from the low pressure off-gas. The concentration of carbon monoxide in the low pressure off-gas is maintained according to the formula: Y>mX+C wherein Y is the molar concentration of carbon monoxide in the low pressure off-gas, X is the concentration in ppm by weight of ruthenium in the liquid reaction composition, m is about 0.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: April 10, 2007
    Assignee: BP Chemicals Limited
    Inventor: Michael James Muskett
  • Patent number: 7169954
    Abstract: A ruthenium-carrying alumina, which is prepared by suspending alumina in a solution containing trivalent ruthenium and adding a base to the suspension, is provided. This ruthenium-carrying alumina is useful as a catalyst for oxidizing alcohols by contacting the alcohols with molecular oxygen, and can be used for oxidizing the alcohols at a high conversion to produce ketones, aldehydes, carboxylic acids, etc. with good productivity.
    Type: Grant
    Filed: April 25, 2003
    Date of Patent: January 30, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritaka Mizuno, Kazuya Yamaguchi, Hajime Ishida
  • Patent number: 7115774
    Abstract: In a process for liquid phase carbonylation of alcohols by carbon monoxide, the carbonylation reaction is carried out in a reaction zone at a temperature of 50° C. to 150° C. at a pressure in the range 0.5 MPa to 20 MPa in the presence of at least one catalyst comprising at least one rhodium and/or iridium complex and a halogenated promoter in at least one non-aqueous ionic liquid comprising at least one salt with general formula Q+A?, in which Q+ represents a quaternary ammonium and/or a quaternary phosphonium cation, said salt having a melting point of less than 90° C.; the non-aqueous ionic liquid containing at least the major portion of the catalyst is separated; and the separated non-aqueous ionic liquid containing at least the major portion of the catalyst is returned to the reaction zone.
    Type: Grant
    Filed: May 22, 2003
    Date of Patent: October 3, 2006
    Assignee: Institut Francais du Petrole
    Inventors: Lionel Magna, Helene Olivier-Bourbigou, Stephane Harry, Dominique Commereuc
  • Patent number: 7109379
    Abstract: An oily solution of water-insoluble aliphatic alcohol is allowed to react with an aqueous hydrogen peroxide solution in the presence of a catalyst containing a metal compound belonging to Group 8 to 10 of the Periodic Table in a heterogeneous solution system. As a result, a carbonyl compound can be produced from an aqueous hydrogen peroxide solution under mild conditions in high yield. Also, the reaction operation is simple and easy, a step for removing solvent after completion of the reaction is not necessary and influence and toxicity upon the environment and human body are markedly small. Thus, a carbonyl compound can be produced safely, simply and efficiently.
    Type: Grant
    Filed: July 24, 2003
    Date of Patent: September 19, 2006
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Kazuhiko Sato, Youko Usui
  • Patent number: 7098363
    Abstract: A process for the production of a product comprising a carboxylic acid having n+1 carbon atoms which process comprises reacting in the liquid phase at elevated temperature and pressure a composition comprising an alcohol having n carbon atoms and/or a reactive derivative thereof, a halogen and/or a halogen compound promoter, water and carbon monoxide in the presence of hydrogen and a heterogeneous catalyst comprising a Group VIII noble metal species on a polymeric resin having a functional group selected from nitrogen-containing heterocycles.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: August 29, 2006
    Assignee: BP Chemicals Limited
    Inventor: Michael David Jones
  • Patent number: 7053241
    Abstract: Processes for the production of acetic acid by carbonylation of methanol, and reactive derivatives thereof, in a reaction mixture using a rhodium-based catalyst system with at least one metal salt catalyst stabilizer selected from the group of ruthenium salts, tin salts, and mixtures thereof are provided. The metal salt stabilizers minimize precipitation of the rhodium metal during recovery of the acetic acid product, particularly in flasher units in an acetic acid recovery scheme. Stability of the rhodium metal is achieved even when the acetic acid is produced in low water content reaction mixtures in the presence of an iodide salt co-promoter at a concentration that generated an iodide ion concentration of greater than about 3 wt. % of the reaction mixture. The stabilizing metal salts may be present in the reaction mixtures for the production of acetic acid at molar concentrations of metal to rhodium of about 0.1:1 to about 20:1.
    Type: Grant
    Filed: February 24, 2005
    Date of Patent: May 30, 2006
    Assignee: Celanese International Corporation
    Inventor: G. Paull Torrence
  • Patent number: 7034170
    Abstract: Manganese(IV) complex salts of formula [LMn(?-O)3MnL]n[XM12O40]m, (I), wherein L is 1,4,7-trimethyl-1,4,7-triazacyclononane, X is P or Si, M is Mo or W, n is 2 or 3, and m is 1 or 2, with the provisos that (i) if X is Si, then n=2 and m=1 and (ii) if X is P, then n=3 and m=2. These compounds are active catalysts in the partial oxidation of various organic compounds with peroxy compounds, e.g., the preparation of ketones from secondary alcohols or the epoxidation of olefins.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: April 25, 2006
    Assignee: Lonza AG
    Inventors: Marco Bosch, Dario Veghini
  • Patent number: 7009070
    Abstract: The invention relates to a continuous process for the manufacture of acetic acid and/or methyl acetate, characterized in that, during the continuous operation of the installation for a continuous industrial process, called the initial process, for the carbonylation of methanol or a carbonylatable derivative of methanol such as dimethyl ether, methyl halides or methyl acetate, in the homogeneous liquid phase and under carbon monoxide pressure, in the presence of a catalyst system comprising a rhodium-based homogeneous catalyst and a halogenated promoter, and in the presence of a concentration of water greater than or equal to 14% in the reaction medium, the composition of said homogeneous catalyst is modified gradually by adding an iridium compound over time.
    Type: Grant
    Filed: February 5, 2002
    Date of Patent: March 7, 2006
    Assignee: Acetex Chimie
    Inventors: Daniel Thiebaut, Daniel Marchand, Philippe Kalck, Carole Le Berre, Philippe Serp
  • Patent number: 7005541
    Abstract: The invention relates to a process for the production of acetic acid by carbonylation of methanol, and reactive derivatives thereof, in a reaction mixture using a rhodium-based catalyst in low water conditions. The process is used to achieve reaction rates of at least 15 g mol/l/hr. The high rate reactions proceed at water concentrations of less than 2.0 wt. %. Under certain conditions, the water concentration in the reaction mixture of the process is maintained at a desired concentration by at least one process step including adding a compound such as methyl acetate, dimethyl ether, acetic anhydride, or mixtures of these compounds to the reaction system. The process step of adding the components to the reaction mixture may be combined with other process steps for controlling water concentrations in reaction mixtures for the carbonylation of methanol.
    Type: Grant
    Filed: December 23, 2002
    Date of Patent: February 28, 2006
    Assignee: Celanese International Corporation
    Inventors: Hosea Cheung, Michael E. Huckman, G. Paull Torrence
  • Patent number: 6916952
    Abstract: The invention relates to a process for the preparation of acetic acid and/or methyl acetate in the liquid phase by the carbonylation of methanol and/or the isomerization of methyl formate in the presence of water, a solvent, a homogeneous catalyst system comprising iridium and a halogen-containing promoter, and carbon monoxide, wherein said catalyst system also comprises platinum.
    Type: Grant
    Filed: October 29, 1999
    Date of Patent: July 12, 2005
    Assignee: Acetex Chimie
    Inventors: Carole Le Berre, Philippe Kalck, Philippe Serp, Lise Layeillon, Daniel Thiebaut
  • Patent number: 6916951
    Abstract: Disclosed is a continuous process wherein carbon monoxide, a carbonylatable reactant, and a halide in the gas phase are contacted with a non-volatile catalyst solution comprising an ionic liquid and a Group VIII metal to produce a carbonylation product in the gas phase. The process is useful for the continuous preparation of acetic acid by the carbonylation of methanol.
    Type: Grant
    Filed: May 9, 2003
    Date of Patent: July 12, 2005
    Assignee: Eastman Chemical Company
    Inventors: Gerald Charles Tustin, Regina Michelle Moncier
  • 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: 6858753
    Abstract: The present invention provides an improved process for the production of carboxylic acids by the carbonylation of alcohol. The process involves contacting an alcohol with carbon monoxide in the presence of a nickel compound, a heterocyclic organic compound and an iodide promoter to produce the corresponding carboxylic acid. The improvement relates to the use of heterocyclic organic compound as a promoter containing at least two heteroatoms of which at least one is selected independently from S or N, which provides an inexpensive and stable catalyst system.
    Type: Grant
    Filed: March 14, 2002
    Date of Patent: February 22, 2005
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, Sunil Shankar Joshi, Ashutosh Anant Kelkar, Sunil Sadashiv Divekar
  • Patent number: 6846951
    Abstract: An integrated large capacity, single-train process for making 1,00020,000 MTPD methanol and 3006,000 MTPD acetic acid is disclosed. Syngas 120 is produced by autothermal reforming 118 of natural gas 102 where the feed 112 of the natural gas is supplied with oxygen and CO2 recycle 110 to the autothermal reformer (ATR) 118. A portion (5-50%) of the syngas is fed to CO2 removal 122 to obtain the recycle CO2 and cold box 130 to obtain a hydrogen stream 131 and a CO stream 135. The 50-95% remaining syngas, hydrogen stream 131 and optionally any CO2 from an associated process are fed to methanol synthesis 140, which produces the methanol. The methanol is supplied to an acetic acid unit 136 with the CO 135 to make the acetic acid, which in turn can be supplied to a VAM synthesis unit 148. Oxygen for the ATR and any VAM synthesis can be supplied by a single common air separation unit 116, and utilities such as steam generation can further integrate the process.
    Type: Grant
    Filed: October 9, 2003
    Date of Patent: January 25, 2005
    Assignee: Acetex (Cyprus) Limited
    Inventor: Daniel Marcel Thiebaut
  • Patent number: 6784313
    Abstract: A process for producing a carboxylic acid having (n+1) carbon atoms, which includes carbonylating an alcohol having n carbon atoms, and/or an ester of the alcohol and the carboxylic acid in each alkyl group with carbon monoxide in the presence of a catalytic system containing a rhodium catalyst. The process uses a reaction medium for the carbonylation that includes: (1) a rhodium catalyst, (2) an organic halide corresponding to said alcohol, (3) an ester of the alcohol and the carboxylic acid, (4) the carboxylic acid, optionally (5) water, a haloid acid, an inorganic halogen salt or an acetate, and (6) a cocatalyst selected from arginine, N-acetyl alanine, or nitrogen- and oxygen-containing organic compounds.
    Type: Grant
    Filed: October 4, 2002
    Date of Patent: August 31, 2004
    Assignee: China Petrochemical Development Corporation
    Inventors: Chia Jung Tsai, Yao Lung Liu, Hsi Chin Tsai
  • Publication number: 20040122257
    Abstract: The invention relates to a process for the production of acetic acid by carbonylation of methanol, and reactive derivatives thereof, in a reaction mixture using a rhodium-based catalyst in low water conditions. The process is used to achieve reaction rates of at least 15 g mol/l/hr. The high rate reactions proceed at water concentrations of less than 2.0 wt. %. Under certain conditions, the water concentration in the reaction mixture of the process is maintained at a desired concentration by at least one process step including adding a compound such as methyl acetate, dimethyl ether, acetic anhydride, or mixtures of these compounds to the reaction system. The process step of adding the components to the reaction mixture may be combined with other process steps for controlling water concentrations in reaction mixtures for the carbonylation of methanol.
    Type: Application
    Filed: December 23, 2002
    Publication date: June 24, 2004
    Inventors: Hosea Cheung, Michael E. Huckman, G. Paull Torrence
  • Publication number: 20040059153
    Abstract: In a process for liquid phase carbonylation of alcohols by carbon monoxide:
    Type: Application
    Filed: May 22, 2003
    Publication date: March 25, 2004
    Applicant: Institut Francais du Petrole
    Inventors: Lionel Magna, Helene Olivier-Bourbigou, Stephane Harry, Dominique Commereuc
  • Publication number: 20040044245
    Abstract: The invention relates to a continuous process for the manufacture of acetic acid and/or methyl acetate, characterized in that, during the continuous operation of the installation for a continuous industrial process, called the initial process, for the carbonylation of methanol or a carbonylatable derivative of methanol such as dimethyl ether, methyl halides or methyl acetate, in the homogeneous liquid phase and under carbon monoxide pressure, in the presence of a catalyst system comprising a rhodium-based homogeneous catalyst and a halogenated promoter, and in the presence of a concentration of water greater than or equal to 14% in the reaction medium, the composition of said homogeneous catalyst is modified gradually by adding an iridium compound over time.
    Type: Application
    Filed: June 11, 2003
    Publication date: March 4, 2004
    Inventors: Daniel Thiebaut, Daniel Marchand, Philippe Kalck, Carole Le Berre, Philippe Serp
  • Patent number: 6686500
    Abstract: A process for the production of acetic acid by reacting carbon monoxide with methanol and/or a reactive derivative thereof in a liquid reaction composition comprising an iridium carbonylation catalyst, methyl iodide, methyl acetate, water and acetic acid characterised in that there is also present in the reaction composition a monodentate phosphine oxide compound in an amount of up to and including 200 mol per gram atom of iridium.
    Type: Grant
    Filed: October 31, 2000
    Date of Patent: February 3, 2004
    Assignee: BP Chemicals Limited
    Inventor: Robert John Watt
  • Patent number: 6677480
    Abstract: A process for monitoring and controlling reactor conditions during the production of acetic acid by the catalyzed carbonylation of methanol is provided. The process of the present invention comprises measuring the density of the heavy phase of the light ends distillation column in the purification system of the carbonylation process. The density measurement is used to adjust the feed of methanol and/or to regulate the temperature in the reaction zone to optimize reactor conditions. The density measurement may also be used to adjust other parameters in the reactor system. The invention is also directed to the system for manufacturing acetic acid based on the process control procedure described.
    Type: Grant
    Filed: January 28, 2002
    Date of Patent: January 13, 2004
    Assignee: Celanese International Corporation
    Inventors: Michael E. Huckman, G. Paull Torrence, Hung-Cheun Cheung
  • Patent number: 6667418
    Abstract: A method and system is provided for producing acetic acid by the catalytic carbonylation of methanol with carbon monoxide to obtain a reaction product stream comprising acetic acid and a minor amount of acetaldehyde. The acetaldehyde content in the reaction product stream is reduced by oxidation to convert at least a portion of the acetaldehyde in the stream to acetic acid or further to CO2 and H2O. The oxidized stream may then be directed to the purification section, the reaction section, or both whereby the deleterious effects of acetaldehyde are reduced. Advantage of the present invention over conventional processes is the reduced need to dispose of acetaldehyde as waste and improved overall system efficiency in the production of acetic acid.
    Type: Grant
    Filed: April 16, 2002
    Date of Patent: December 23, 2003
    Assignee: Celanese International Corporation
    Inventors: Jerry A. Broussard, Hung-Cheun Cheung, Stephen Andrew Houliston, Michael E. Huckman, Peggy McKarns Macatangay, Madan Singh, Michael L. Karnilaw, G. Paull Torrence
  • Patent number: 6657078
    Abstract: A low energy process for producing acetic acid by the carbonylation of methanol is disclosed. The process involves a rhodium-catalyzed system operated at less than about 14% water utilizing up to 2 distillation columns. The process is preferably controlled such that the product stream has a low level of propionic acid impurity and the level of aldehyde impurities is minimized by way of aldehyde removal or minimizing aldehyde generation. The level of iodides is controlled by contacting the product, at elevated temperatures, with ion exchange resins. In preferred embodiments, at least one silver or mercury exchanged macroreticular strong acid ion exchange resin is used to purify the product. The high temperature treatment provides the added benefit of controlling the Color Value (Pt—Co units) of the product stream.
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: December 2, 2003
    Assignee: Celanese International Corporation
    Inventors: Mark O. Scates, George A. Blay, G. Paull Torrence, Jerry A. Broussard
  • Patent number: 6646154
    Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compounds, and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase carbonylation conditions with a catalyst having a catalytically effective amount of a Group VIII metal selected from platinum or palladium, and tungsten which are associated with a solid catalyst support material.
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: November 11, 2003
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6642413
    Abstract: A continuous preparative process, including monitoring production, for acetic acid, methyl acetate or a mixture thereof, by carbonylation, in an industrial installation, of methanol or a carbonylatable derivative of methanol with carbon monoxide in a liquid phase in the presence of water and a homogeneous catalyst system. In a reaction zone I, the carbonylation is carried out in the liquid phase at a temperature of 150 to 250° C., under a pressure of 5·105 to 200·105 Pa and with venting of part of a gaseous canopy above a liquid phase level in said reactor. Then, in a vaporization or flash zone II, a liquid originating from the zone I at a pressure below that of zone I is partially vaporized to form a liquid fraction which is recycled into the reactor, and in a purification zone III, a vaporized fraction originating from flash zone II is distilled on a distillation column.
    Type: Grant
    Filed: September 13, 2001
    Date of Patent: November 4, 2003
    Assignee: Acetex Chimie
    Inventor: Daniel Thiebaut
  • 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
  • Publication number: 20030199711
    Abstract: A method and system is provided for producing acetic acid by the catalytic carbonylation of methanol with carbon monoxide to obtain a reaction product stream comprising acetic acid and a minor amount of acetaldehyde. The acetaldehyde content in the reaction product stream is reduced by oxidation to convert at least a portion of the acetaldehyde in the stream to acetic acid or further to CO2 and H2O. The oxidized stream may then be directed to the purification section, the reaction section, or both whereby the deleterious effects of acetaldehyde are reduced. Advantage of the present invention over conventional processes is the reduced need to dispose of acetaldehyde as waste and improved overall system efficiency in the production of acetic acid.
    Type: Application
    Filed: April 16, 2002
    Publication date: October 23, 2003
    Inventors: Jerry A. Broussard, Hung-Cheun Cheung, Stephen Andrew Houliston, Michael E. Huckman, Peggy McKarns MacAtangay, Madan Singh, Michael L. Karnilaw, G.Paull Torrence
  • Patent number: 6627770
    Abstract: A method and apparatus for sequestering entrained or volatile catalyst species in a carbonylation process includes contacting the product stream with a vinyl pyridine or a vinyl pyrrolidone resin bed which is operative to sequester entrained or volatile catalytic species. The invention is particularly useful in connection with the iridium catalyzed carbonylation of methanol wherein the loss of entrained or volatile catalyst species depletes the catalytic content of the reactor. The resin may be digested in order to recover the catalytic metals.
    Type: Grant
    Filed: August 24, 2000
    Date of Patent: September 30, 2003
    Assignee: Celanese International Corporation
    Inventors: Hung-Cheun Cheung, Valerie Santillan, Mark O. Scates, Elaine C. Sibrel, G. Paull Torrence
  • Publication number: 20030181760
    Abstract: While supplying methanol and carbon monoxide via feed lines 17 and 19, respectively, to a liquid phase reaction system 3 including a carbonylation catalytic system, and maintaining a substantially constant liquid level of the reaction system, part of the reaction mixture containing the produced acetic acid is drawn out from the reaction system and supplied to a flash distillation column 4, and the high boiling point component, which contains the carbonylation catalytic system that has been separated by ths flash distillation, is circulated to the reaction system 3 by means of a circulation line 21. At circulation line 21, the flow rate is detected by a flow rate sensor F3 and the temperature is detected by a temperature sensor T2, and based on the detection data, a control unit 8 is used to control the temperature of the circulated high boiling point component by means of a temperature regulating unit 6 and thereby to suppress temperature and pressure fluctuations of the above-mentioned reaction system.
    Type: Application
    Filed: October 10, 2002
    Publication date: September 25, 2003
    Inventors: Hidehiko Nakajima, Yoshiyuki Harano
  • Publication number: 20030176732
    Abstract: The present invention provides an improved process for the production of carboxylic acids by the carbonylation of alcohol. The process involves contacting an alcohol with carbon monoxide in the presence of a nickel compound, a heterocyclic organic compound and an iodide promoter to produce the corresponding carboxylic acid. The improvement relates to the use of heterocyclic organic compound as a promoter containing at least two heteroatoms of which at least one is selected independently from S or N, which provides an inexpensive and stable catalyst system.
    Type: Application
    Filed: March 14, 2002
    Publication date: September 18, 2003
    Inventors: Raghunath Vitthal Chaudhari, Sunil Shankar Joshi, Ashutosh Anant Kelkar, Sunil Sadashiv Divekar