Preparing Esters By Carbonylation Patents (Class 560/232)
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Publication number: 20080146833Abstract: A product comprising a C1-C3 aliphatic carboxylic acid or corresponding ester is produced by a process comprising carbonylating a C1-C3 aliphatic alcohol or a corresponding ester with carbon monoxide in the presence of a zeolite catalyst having an 8-member ring channel which is interconnected with a channel defined by a ring with greater than or equal to 8 members, the 8-member ring having a window size of at least 2.5 Angstroms×at least 3.6 Angstroms and at least one Brønsted acid site and the zeolite having a silica:X2O3 ratio of at least 5, wherein X is selected from aluminium, boron, iron, gallium and mixtures thereof with the proviso that the zeolite is not mordenite or ferrierite.Type: ApplicationFiled: December 15, 2006Publication date: June 19, 2008Applicant: The Regents of the University of CaliforniaInventors: Enrique Iglesia, John Glenn Sunley, David John Law, Aditya Bhan
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Publication number: 20070293695Abstract: 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: ApplicationFiled: June 15, 2006Publication date: December 20, 2007Applicant: EASTMAN CHEMICAL COMPANYInventors: Joseph Robert Zoeller, Mary Kathleen Moore, Andrew James Vetter
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Patent number: 7309798Abstract: A product comprising a lower alkyl ester of a lower aliphatic carboxylic acid is produced by a process comprising reacting a lower alkyl ether with carbon monoxide in the presence of a catalyst comprising mordenite and/or ferrierite, optionally including an additional framework metal such as gallium, boron and/or iron, under substantially anhydrous conditions. More specifically, methyl acetate is selectively produced by reaction of dimethyl ether with carbon monoxide in the presence of a catalyst comprising mordenite or ferrierite, under substantially anhydrous conditions.Type: GrantFiled: May 3, 2006Date of Patent: December 18, 2007Assignees: The Regents of the University of California, BP Chemicals LimitedInventors: Patricia Cheung, Enrique Iglesia, John Glenn Sunley, Aditya Bhan, David John Law
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Patent number: 7288672Abstract: The present invention relates to a process for the preparation of esters of hydroxy tiglic aldehydes which are the key intermediates for Vitamin-A acetate synthesis and various perfumistic products, said process relates to the hydroformylation of biscarboxylic esters of but-2-ene-1,4-diol, followed by deacetoxylation of its hydroformylation compound, in the presence of heterogeneous catalyst having rhodium complex entrapped, anchored or teethered on the acidic support, said acidic support causes deacetoxylation in the reaction mixture immediately after hydroformylation, to give 100% selectivity to the carboxylic esters of hydroxyl tiglic aldehydes in a single step.Type: GrantFiled: March 29, 2004Date of Patent: October 30, 2007Assignee: Council of Scientific & Industriual ResearchInventors: Raghunath Vitthal Chaudhari, Rashmi Chansarkar, Kausik Mukhopadhyay, Ashutosh Anant Kelkar
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Patent number: 7276626Abstract: 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: GrantFiled: May 5, 2004Date of Patent: October 2, 2007Assignee: BP Chemicals LimitedInventors: Sander Gaemers, John Glenn Sunley
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Patent number: 7265242Abstract: A process for the carbonylation of unsaturated compounds by contacting the unsaturated compound with carbon monoxide in the presence of a catalyst system comprising: (a) a source of palladium and/or platinum; and (b) an unsymmetrical bidentate diphosphine ligand of formula I, R1R2>P1?R3?P2<R4R5??(I) wherein P1 and P2 represent phosphorus atoms; R3 represents a divalent organic bridging group; and R1, R2, R4 and R5 each individually, or R1 and R2 jointly, and/or R4 and R5 jointly represent organic groups that are covalently linked to the phosphorus; and wherein R1, R2, R4 and R5 are chosen in such way, that the phosphino group R1R2>P1 differs from the phosphino group P2<R4R5.Type: GrantFiled: November 24, 2004Date of Patent: September 4, 2007Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager, Robert Ian Pugh
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Patent number: 7253304Abstract: Disclosed is a carbonylation process wherein a mixture of a dialkyl carbonate and halide compound is contacted with carbon monoxide in the presence of a metal selected from Group VIII of the Periodic Table to co-produce carbon dioxide and a carbonyl compound selected from a carboxylic acid, an alkyl carboxylate ester, a carboxylic acid anhydride or a mixture of any two or more thereof. The carbon dioxide co-product of the process may be recovered, and sold or further reacted with a suitable substrate to produce useful chemicals such as urea or cyclic carbonates.Type: GrantFiled: June 20, 2006Date of Patent: August 7, 2007Assignee: Eastman Chemical CompanyInventor: Gerald Charles Tustin
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Patent number: 7223886Abstract: 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: GrantFiled: March 2, 2004Date of Patent: May 29, 2007Assignee: Celanese International CorporationInventors: Mark O. Scates, David A. Trueba, Raymond J. Zinobile
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Patent number: 7151192Abstract: A manufacturing process for the preparation of ?,?-branched alkane carboxylic acids, by reacting a mono-olefin or a precursor thereof, with carbon monoxide in the presence of a strong acid catalyst characterized in that the starting olefin is a dimmer C8 or trimer C12 derived from n-butene, which predominantly comprise 2-butene, that the acid catalyst is composed of BF3/H3PO4 in a molar ratio of BF3:H3PO4 in the range of from 0.5:1.0 to 5.0:1.0, or of CF3SO 3H, that the weight ratio of the catalyst relative to the mono-olefin is in the range of from 1:1 to 10:1, that the reaction is carried out at a temperature in the range of from 60 to 140° C., and with an initial water content in the catalyst system in the range of from 8 to 25 wt %; and vinyl esters and glycidyl esters derived from said carboxylic acids.Type: GrantFiled: July 2, 2002Date of Patent: December 19, 2006Assignee: Hexion Specialty Chemicals, Inc.Inventors: Hendrik Stichter, Leonardus Petrus, Hans Arie Stil
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Patent number: 7081547Abstract: A process for producing a formic ester comprises reacting carbon monoxide with an alcohol to produce a formic ester, wherein the reaction is performed in the presence of water and/or carbon dioxide and in the presence of (1) an alkali metal-type catalyst other than an alkali metal alkoxide and other than an alkali fluoride, or (2) an alkali metal-type catalyst other than an alkali metal alkoxide and other than an alkali fluoride in combination with an alkaline earth metal-type catalyst.Type: GrantFiled: March 4, 2004Date of Patent: July 25, 2006Assignee: Nippon Steel CorporationInventors: Kaoru Fujimoto, Noritatsu Tsubaki, Kenichiro Fujimoto
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Patent number: 7052657Abstract: 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: GrantFiled: February 15, 2002Date of Patent: May 30, 2006Assignee: Daicel Chemical Industries, Ltd.Inventors: Hidehiko Nakajima, Yoshiyuki Harano
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Patent number: 7053239Abstract: The invention relates to a process for the preparation of methyl formate by reacting methanol with carbon monoxide at a pressure of from 0.5 to 10 MPa abs. and a temperature of from 50 to 150° C. in the presence of a metal alkoxide as catalyst in a reactor, in which a gas stream is withdrawn from the reactor, entrained methyl formate is removed from this gas stream by condensation, and all or some of the remaining gas stream is returned to the reactor as circulating-gas stream and a mean gas superficial velocity of from 1 to 20 cm/s is set in at least one region of the reactor in which the gas flows essentially in one direction.Type: GrantFiled: April 15, 2003Date of Patent: May 30, 2006Assignee: BASF AktiengesellschaftInventors: Christoph Adami, Michael Slany, Jörn Karl, Gerd Kaibel, Martin Schäfer, Peter Zehner, Michael Röper
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Patent number: 7009070Abstract: 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: GrantFiled: February 5, 2002Date of Patent: March 7, 2006Assignee: Acetex ChimieInventors: Daniel Thiebaut, Daniel Marchand, Philippe Kalck, Carole Le Berre, Philippe Serp
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Patent number: 7005537Abstract: Disclosed is a process for the production of esters. In particular, the process includes contacting an olefin or an ether with carbon monoxide and an acid composition comprising BF3.2CH3OH to from a product composition, adding an alcohol to the product composition, and separating the BF3.2CH3OH from the ester. The separated BF3.2CH3OH may then be recycled to the reaction unit.Type: GrantFiled: December 26, 2000Date of Patent: February 28, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Edmund J. Mozeleski, Carl R. Beck, Kirk C. Nadler, Richard H. Schlosberg
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Patent number: 6956134Abstract: Feeds comprising methanol, dimethyl ether or a mixture of the two are oxidized by contacting the feed with an oxygen-containing gas and a supported heteropolyacid catalyst containing molybdenum or molybdenum and vanadium. The primary products are methylal (dimethoxymethane) and methyl formate. Production of dimethyl ether from methanol can be inhibited by partial deactivation of acid sites on the Keggin catalyst.Type: GrantFiled: January 8, 2004Date of Patent: October 18, 2005Assignee: The Regents of the University of CaliforniaInventors: Haichao Liu, Enrique Iglesia
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Patent number: 6921833Abstract: A description is given of a process for preparing methyl formate by reacting excess methanol with carbon monoxide under superatmospheric pressure and at elevated temperature in the presence of alkali metal methoxide or alkaline earth metal methoxide as catalyst in a pressure-rated reactor, in which the use of at least two reactor elements, preferably operated in countercurrent, at about 100° C. and a pressure of about 100 bar in combination with a solids-free desalting of the reaction product makes possible very economical, largely trouble-free production of methyl formate in any desired quality and with a very good production capacity. Furthermore, the process for solids-free desalting and apparatuses for carrying out this process are described.Type: GrantFiled: July 26, 2000Date of Patent: July 26, 2005Assignee: BASF AktiengesellschaftInventors: Heinz Auer, Jürgen Dahlhaus, Karl Fischer, Hans Hammer, Jochen Kellenbenz, Michael Schulz, Joachim Thiel, Maximilian Vicari
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Patent number: 6916951Abstract: 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: GrantFiled: May 9, 2003Date of Patent: July 12, 2005Assignee: Eastman Chemical CompanyInventors: Gerald Charles Tustin, Regina Michelle Moncier
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Patent number: 6916952Abstract: 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: GrantFiled: October 29, 1999Date of Patent: July 12, 2005Assignee: Acetex ChimieInventors: Carole Le Berre, Philippe Kalck, Philippe Serp, Lise Layeillon, Daniel Thiebaut
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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: 6846951Abstract: 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: GrantFiled: October 9, 2003Date of Patent: January 25, 2005Assignee: Acetex (Cyprus) LimitedInventor: Daniel Marcel Thiebaut
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Publication number: 20040171704Abstract: A production process and a catalyst are provided, which can be less decreased in activity of the catalyst even when CO2, water and the like are present in the starting material and/or the reaction system, and which can produce a formic ester or a methanol at a low temperature and a low pressure.Type: ApplicationFiled: March 4, 2004Publication date: September 2, 2004Applicant: Nippon Steel CorporationInventors: Kaoru Fujimoto, Noritatsu Tsubaki, Kenichiro Fujimoto
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Patent number: 6781014Abstract: The retrofitting of an existing methanol or methanol/ammonia plant to make acetic acid is disclosed. The existing plant has a reformer (10) to which natural gas or another hydrocarbon and steam (water) are fed. Syngas is formed in the reformer (10). All or part of the syngas is process to separate out carbon dioxide (24), carbon monoxide (30) and hydrogen (32), and the separated carbon dioxide (24) is the existing to the existing methanol synthesis loop (12) for methanol synthesis, or back into the feed to the reformer (10) to enhance carbon monoxide formation in the syngas (18). Any remaining syngas (38) not fed to the carbon dioxide separator (22) can be converted to methanol in the existing methanol synthesis loop (12) along with carbon dioxide (24) from the separator (22) and/or imported carbon dioxide (25), and hydrogen (35) from the separator (28). The separated carbon monoxide (30) is then reacted with the methanol (36) to produce acetic acid (40) or an acetic acid precursor by a conventional process.Type: GrantFiled: April 30, 2002Date of Patent: August 24, 2004Assignee: Acetex (Cyprus) LimitedInventors: Kenneth Ebenes Vidalin, Daniel Marcel Thiebaut
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Patent number: 6774083Abstract: A process for improving the stability and/or preventing the deactivation of catalyst in processes of continuous manufacture of acetic acid and/or methyl acetate includes a first, reaction step wherein at least one methyl formate isomerization reaction is carried out in a liquid phase reaction medium, in the presence of carbon monoxide and of a catalytic system including at least one halogenated promoter and at least one iridium-based catalytic compound, and, a second, flash step in which partial vaporization of a reaction medium originating from the first step is carried out in a flash separator. In a non-vaporized liquid fraction resulting from the partial vaporization in the flash separator, an overall content of formic acid and methyl formate is maintained at least equal to 1% by weight of said non-vaporized liquid fraction.Type: GrantFiled: May 1, 2003Date of Patent: August 10, 2004Assignee: Acetex ChimieInventors: Daniel Thiebaut, Carl Patois, Lise Layeillon, Daniel Marchand
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Patent number: 6706912Abstract: Process for the carbonylation of ethylenically unsaturated compounds having 3 or more carbon atoms by reaction with carbon monoxide and an hydroxyl group containing compound in the presence of a catalyst system. The catalyst system includes (a) a source of palladium cations; (b) a bidentate diphosphine of formula I, R1R2>P—R3—R—R4—P<R5R6 (I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted alkylene groups and R represents an optionally substituted aromatic group; (c) a source of anions derived from an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution. The process is carried out in the presence of an aprotic solvent.Type: GrantFiled: March 13, 2001Date of Patent: March 16, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
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Publication number: 20040044245Abstract: 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: ApplicationFiled: June 11, 2003Publication date: March 4, 2004Inventors: Daniel Thiebaut, Daniel Marchand, Philippe Kalck, Carole Le Berre, Philippe Serp
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Patent number: 6646154Abstract: 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: GrantFiled: June 20, 2001Date of Patent: November 11, 2003Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6646159Abstract: Long chain alcohols and acids or other similar oxygenates such as esters are produced from paraffins of similar carbon number by a process comprising paraffin dehydrogenation, carbonylation, and separation. Preferably a mixture of paraffins extending over several carbon numbers and recovered from a kerosene fraction is processed, and unconverted paraffins are recycled to a dehydrogenation zone. Alternative reaction zone configurations, catalyst systems and product recovery methods are disclosed.Type: GrantFiled: December 21, 2000Date of Patent: November 11, 2003Assignee: UOP LLCInventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
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Patent number: 6642413Abstract: 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: GrantFiled: September 13, 2001Date of Patent: November 4, 2003Assignee: Acetex ChimieInventor: Daniel Thiebaut
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Patent number: 6617472Abstract: The present invention relates to process for improving the stability and/or preventing the deactivation of the catalyst in processes of manufacture of acetic acid and/or of methyl acetate according to which processes, in a first step, referred to as the reaction step, at least one methyl formate isomerization reaction is carried out in liquid phase, in the presence of carbon monoxide and of a catalytic system comprising at least one halogenated promoter and at least one iridium-based catalytic compound, and, in a second step, referred to as the flash step, the partial vaporization of the reaction medium originating from the first step is carried out in a separator referred to as the flash separator, characterized in that it consists in maintaining an overall content of formic acid and of methyl formate at least equal to 1% by weight of said liquid fraction, preferably between 1 and 50%, preferably between 1 and 30%, by weight with respect to said liquid fraction, in the non-vaporized liquid fraction originatiType: GrantFiled: December 13, 2001Date of Patent: September 9, 2003Assignee: Acetex ChimieInventors: Daniel Thiebaut, Carl Patois, Lise Layeillon, Daniel Marchand
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Patent number: 6617471Abstract: 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 conditions with a catalyst having a catalytically effective amount of iridium and tin associated with a solid carrier material.Type: GrantFiled: June 20, 2001Date of Patent: September 9, 2003Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6613938Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compositions and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase conditions with a catalyst having a catalytically effective amount of platinum and tin associated with a solid carrier material.Type: GrantFiled: June 19, 2001Date of Patent: September 2, 2003Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6602476Abstract: Apparatus and process for heat exchange with fluid beds comprises heat-exchange tubes located longitudinally with respect to the axis of a fluidization zone with a rectangular pitch, one side of which having a length at least one and a half times the length of the other side and/or with a triangular pitch, having two sides each at least one and a half times the length of the shortest side reduces the impact of the heat-exchange tubes on the fluidization characteristics of the fluid bed. The invention is particularly suitable for oxidation reactions using molecular oxygen-containing gas in the presence of a fluid bed of fluidizable catalyst, such as (a) the acetoxylation of olefins, (b) the oxidation of ethylene to acetic acid and/or the oxidation of ethane to ethylene and/or acetic acid, (c) the ammoxidation of propylene and/or propane to acrylonitrile and (d) the oxidation of C4's to maleic anhydride.Type: GrantFiled: September 28, 2001Date of Patent: August 5, 2003Assignee: BP Chemicals LimitedInventors: Stanley John Becker, Timothy Crispin Bristow, Michele Fiorentino, David Newton, Bruce Leo Williams
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Patent number: 6596781Abstract: An integrated process for carrying out the production of Fischer-Tropsch products and acetic acid made using the methanol and carbonylation route which utilizes the hydrogen recovered from the methanol production to upgrade the Fischer-Tropsch products.Type: GrantFiled: May 2, 2002Date of Patent: July 22, 2003Assignee: Chevron U.S.A. Inc.Inventor: William L. Schinski
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Publication number: 20030065217Abstract: 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 conditions with a catalyst having a catalytically effective amount of iridium and tin associated with a solid carrier material.Type: ApplicationFiled: June 20, 2001Publication date: April 3, 2003Inventors: Joseph Zoeller, Andy Singleton, Gerald Tustin, Donald Carver
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Publication number: 20030060660Abstract: 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: ApplicationFiled: June 20, 2001Publication date: March 27, 2003Inventors: Joseph Zoeller, Andy Singleton, Gerald Tustin, Donald Carver
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Patent number: 6521783Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.Type: GrantFiled: July 10, 2000Date of Patent: February 18, 2003Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
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Publication number: 20030018212Abstract: A vapor-phase carbonylation method for producing esters and carboxylic acids from reactants comprising lower alkyl alcohols, lower alkyl alcohol generating compositions and mixtures thereof. The method includes contacting the reactants and carbon monoxide in a carbonylation zone of a carbonylation reactor under vapor-phase conditions with a catalyst having a catalytically effective amount of platinum and tin associated with a solid carrier material.Type: ApplicationFiled: June 19, 2001Publication date: January 23, 2003Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Publication number: 20030018213Abstract: The invention relates to a process for monitoring acetic acid and/or methyl acetate production in a continuous preparative process by the carbonylation of methanol or a carbonylatable derivative of methanol with carbon monoxide in the liquid phase, in the presence of water and a homogeneous catalyst system, carried out in an industrial installation comprising a reaction zone, a flash zone and a distillative purification zone, wherein the reactor temperature and the feed rate of the methanol or carbonylatable derivative in said reactor are brought under the control, preferably via a multivariable predictive controller, of the carbon monoxide feed rate and at least one of the parameters defining the composition of the reaction medium and/or the vents.Type: ApplicationFiled: September 13, 2001Publication date: January 23, 2003Inventor: Daniel Thiebaut
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Publication number: 20020198403Abstract: The subject for the invention is to efficiently use, recover, and reuse a soluble metallic catalyst with great ease at low cost in various liquid-phase reactions using the soluble metallic catalyst.Type: ApplicationFiled: March 25, 2002Publication date: December 26, 2002Applicant: NIPPON SHOKUBAI CO., LTD.Inventor: Takafumi Kubo
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Patent number: 6472558Abstract: 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 characterized in that there is also present in the reaction composition a polydentate phosphine oxide compound in an amount of less than 10 mol per gram atom of iridium.Type: GrantFiled: October 31, 2000Date of Patent: October 29, 2002Assignee: BP Chemicals LimitedInventors: Lesley Ann Key, David John Law
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Patent number: 6452043Abstract: A method for producing esters, carboxylic acids and mixtures thereof includes contacting, under carbonylation conditions, lower alkyl alcohols, ethers, lower alkyl alcohol derivatives and mixtures thereof and carbon monoxide with a catalyst having a catalytically effective amount a metal selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, tin and mixtures thereof associated with a carbonized polysulfonated divinylbenzene-styrene copolymer matrix. In a preferred aspect of the invention the method is called out under vapor-phase conditions.Type: GrantFiled: April 5, 2000Date of Patent: September 17, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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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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Patent number: 6395927Abstract: A method for preparing acetic acid and/or methyl acetate by simultaneous isomerization and carbonylation reactions. A reaction mixture is provided containing at least one reagent which provides formyl radicals and at least one further reagent which provides methyl radicals, together with water in an amount of at most 5% by weight, carbon monoxide at a partial pressure between 0.1·105 Pa and 25·105 Pa, a solvent and a catalytic system which contains at least one halogenated promoter and at least one iridium-based compound. In a typical reaction mixture, methyl formate is isomerized to form acetic acid according to the reaction: HCOOCH3CH3COOH while methanol undergoes carbonylation to form acetic acid according to the reaction: CH3OH+COCH3COOH The reagent which provides the formyl radicals is kept at or below 20% by weight of the reaction mixture, while the molar ratio of methyl radicals to formyl radicals in the mixture is greater than 1.Type: GrantFiled: September 23, 1998Date of Patent: May 28, 2002Assignee: Acetex ChimieInventors: Carl Patois, Robert Perron, Daniel Thiebaut
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Patent number: 6355595Abstract: A solid supported catalyst suitable for the vapor phase carbonylation of lower aliphatic alcohols, ethers, ester, and ester-alcohol mixtures, and desirably, methanol, to produce acetic acid, methyl acetate and mixtures thereof. The solid supported catalyst includes an effective amount of iridium and at least one second metal selected from group metals of the periodic table of elements, their respective salts and mixtures thereof associated with a solid support material. Desirably, the support material is selected from carbon, activated carbon, pumice, alumina, silica, silica-alumina, magnesia, diatomaceous earth, bauxite, titania, zirconia, clay, magnesium silicate, silicon carbide, zeolites, ceramics and combinations thereof.Type: GrantFiled: August 25, 1999Date of Patent: March 12, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6355837Abstract: A method for producing esters and carboxylic acids from lower alkyl alcohols, ethers, esters and ester-alcohol reactant mixtures and includes the step of contacting a vaporous mixture of the reactants, carbon monoxide and a halide with a supported catalyst under vapor-phase carbonylation conditions. The catalyst includes iridium and a second metal selected from group 4 (titanium, zirconium, hafnium) metals of the periodic table of elements. Desirably, the iridium and secondary metal are deposited on activated carbon as a support material. In a preferred aspect of the invention, the vapor phase carbonylation process is useful for preparing acetic acid, methyl acetate or a mixture thereof.Type: GrantFiled: August 25, 1999Date of Patent: March 12, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
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Patent number: 6348621Abstract: A catalyst system capable of catalyzing the carbonylation of ethylene and a process which uses such a system wherein the catalyst system is obtainable by combining a metal of Group VIII, e.g., palladium, or a compound thereof and a bidentate phosphine, e.g. bis(di-t-butyl phospino)-o-xylene, according to the equation C2H4+CO+ROH→C2H5CO2R,.Type: GrantFiled: October 13, 1999Date of Patent: February 19, 2002Assignee: Imperial Chemical Industries PLCInventors: Xiao Lan Wang, Robert Paul Tooze, Keith Whiston, Graham Ronald Eastham
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Patent number: 6348622Abstract: There is provided a compound of the formula[I]: wherein R represents a hydrogen atom or a protective group for a hydroxyl group; and A represents a hydrogen atom, a halogen atom or a group of the formula A1: Q represents Q3: when A represents a halogen atom or a protective group for a hydroyl group, A represents Q4: wherein R1 and R2 represent a hydrogen atom or a protective group for a hydroxyl group; and when A represents a hydrogen atom, Q is Q2:Type: GrantFiled: February 9, 2000Date of Patent: February 19, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
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Patent number: 6331656Abstract: In a process for the hydroformylation of olefins having from 12 to 100 carbon atoms in the presence of a cobalt carbonyl catalyst at pressures of from 100 to 400 bar and at from 100 to 200° C., depressurization and recovery of the cobalt catalyst by extraction with an aqueous acid solution in the presence of atmospheric oxygen, (a) the extraction is carried out in the presence of a polymeric emulsion breaker selected from the group consisting of alkoxylated compounds containing amino, imino or OH groups, and (b) to achieve complete phase separation in the organic phase still containing small amounts of aqueous phase, the formation of relatively large droplets of the dispersed aqueous phase is effected in a coalescence stage.Type: GrantFiled: March 4, 1999Date of Patent: December 18, 2001Assignee: BASF AktiengesellschaftInventors: Heinrich-Josef Blankertz, Armin Volker Grenacher, Friedrich Sauer, Harald Schwahn, Willi Schönmann, Michael Röper
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Publication number: 20010041808Abstract: Disclosed is a process for the production of esters. In particular, the process includes contacting an olefin or an ether with carbon monoxide and an acid composition comprising BF3.2CH3OH to from a product composition, adding an alcohol to the product composition, and separating the BF3.2CH3OH from the ester. The separated BF3.2CH3OH may then be recycled to the reaction unit.Type: ApplicationFiled: December 26, 2000Publication date: November 15, 2001Inventors: Edmund J. Mozeleski, Carl R. Beck, Kirk C. Nadler, Richard H. Schlosberg
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Patent number: 6310235Abstract: The invention relates to an improved method for producing ester plasticizers by reacting di- or polycarboxylic acids or their anhydrides with alcohols in the presence of metal catalysts.Type: GrantFiled: November 17, 1999Date of Patent: October 30, 2001Assignee: Celanese GmbHInventor: Wilhelm Gick