Of Alcohol Or Alcoholate Patents (Class 562/519)
-
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
-
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
-
Publication number: 20030144548Abstract: 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: ApplicationFiled: January 28, 2002Publication date: July 31, 2003Inventors: Michael E. Huckman, G. Paull Torrence, Hung-Cheun Cheung
-
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
-
Publication number: 20030135070Abstract: The present invention is directed to using methyl acetate from a vinyl acetate-based or a vinyl-or ethylene-alcohol based polymer or copolymer process directly for use in a methanol carbonylation production process to produce acetic acid, acetic anhydride, or a coproduction of each.Type: ApplicationFiled: December 19, 2002Publication date: July 17, 2003Inventors: Wayne David Picard, Mark O. Scates, Stephen Charles Webb, Duane Lyle Usrey
-
Publication number: 20030130540Abstract: A process for producing a carboxylic acid is disclosed.Type: ApplicationFiled: October 4, 2002Publication date: July 10, 2003Inventors: Chia Jung Tsai, Yao Lung Liu, Hsi Chin Tsai
-
Patent number: 6573403Abstract: A process for producing acetic acid which comprises charging reactants methanol, dimethyl ether, methyl acetate or any mixture thereof into a reactor containing: (1) a rhodium carbonylation catalyst, (2) an alkyl iodide or alkyl bromide, and (3) a hydrogenation catalyst, and contacting the reactants with carbon monoxide and hydrogen to produce acetic acid.Type: GrantFiled: December 5, 2000Date of Patent: June 3, 2003Assignee: Haldor Topsoe A/SInventor: Finn Joensen
-
Patent number: 6552221Abstract: A method of real time process control in a reaction system for the production of acetic acid from the carbonylation of methanol. Reaction system samples are collected from columns and/or transfer lines downstream of a reactor vessel, and the concentration of one or more components in the sample is measured by an infrared analyzer. The concentration measurements are then used to make adjustments in the concentration of components in the reaction system, directly or indirectly, such as by adjusting the temperature profile in a particular column, the flow rate of solution in to or out of a column, the vent gas rate out of the reactor or a column, or the addition or extraction of a component to or from the solution. For optimum process control, the measurements are transmitted to a control unit for real time analysis, and the adjustments are made substantially instantly after the infrared analysis.Type: GrantFiled: September 29, 2000Date of Patent: April 22, 2003Assignee: Millenium Petrochemicals, Inc.Inventors: Noel Hallinan, James A. Hinnenkamp, Javan Shelly
-
Patent number: 6531630Abstract: The converting of an existing methanol plant to make acetic acid is disclosed. The converted plant utilizes the steam reformer (10) to which (a) a hydrocarbon ,e.g., natural gas, or a lower alkanol, e.g., methanol, and (b) steam (water) are fed. Syngas is formed in the reformer (10). All or part of the syngas is processed to separate out carbon dioxide (24), carbon monoxide (30) and hydrogen (32), and the separated carbon dioxide (24) is fed either 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). When a lower alkanol is fed to the reformer (10), the methanol synthesis loop (12) is shutdown and isolated from the rest of the plant.Type: GrantFiled: December 29, 2000Date of Patent: March 11, 2003Inventor: Kenneth Ebenes Vidalin
-
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
-
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
-
Patent number: 6506933Abstract: Disclosed herein is a vapor phase carbonylation process useful for producing carboxylic acids, esters and mixtures thereof from lower aliphatic alcohols, ethers, ester, and ester-alcohol mixtures. The vapor phase carbonylation process is characterized in that it utilizes a solid supported catalyst having an effective amount of gold associated with a solid support material.Type: GrantFiled: May 22, 2000Date of Patent: January 14, 2003Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
-
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
-
Publication number: 20020151746Abstract: 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: ApplicationFiled: February 7, 2001Publication date: October 17, 2002Inventors: Mark O. Scates, George A. Blay, G. Paull Torrence, Jerry A. Broussard
-
Patent number: 6458995Abstract: An improvement to methanol carbonylation processes utilizing a homogeneous iridium catalyst system comprises adding a rate-promoting amount of an insoluble pyridine ring-containing polymer. Typically, polyvinylpyridine is added to the reactor in amounts of up to about 2 wt. percent.Type: GrantFiled: March 31, 2000Date of Patent: October 1, 2002Assignee: Celanese International CorporationInventors: Hung-Cheun Cheung, Elaine C. Sibrel, G. Paul Torrence
-
Publication number: 20020137660Abstract: The present invention relates to a process for the preparation of alkylcarboxylic allyl esters by reacting allyl alcohol and alkylcarboxylic acids.Type: ApplicationFiled: March 18, 2002Publication date: September 26, 2002Inventors: Walter Kuhn, Gerhard Senft
-
Patent number: 6455023Abstract: Carbon monolith-supported catalysts with high leach resistance used in catalytic applications involving strong acidic and basic conditions in a pH range of from 0 to 6.5 and from 7.5 to 14, are respectively described. The leach resistance of the catalyst system originates from strong interaction between the catalyst and the unsaturated valence of the carbon surface. In addition to surprisingly high resistance to leach out, the catalysts also have substantial differential advantages in catalyst performance: catalyst activity, selectivity, and stability.Type: GrantFiled: October 11, 2000Date of Patent: September 24, 2002Assignee: Corning IncorporatedInventors: Kishor P. Gadkaree, Tinghong Tao
-
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
-
Patent number: 6441222Abstract: Disclosed herein is a vapor phase carbonylation process useful for producing carboxylic acids, esters and mixtures thereof from lower aliphatic alcohols, ethers, ester, and ester-alcohol mixtures. The vapor phase carbonylation process is characterized in that it utilizes a solid supported catalyst having an effective amount of iridium and gold associated with a solid support material.Type: GrantFiled: May 22, 2000Date of Patent: August 27, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
-
Publication number: 20020103397Abstract: 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 nitrile group.Type: ApplicationFiled: January 30, 2001Publication date: August 1, 2002Applicant: Council of Scientific and Industrial ResearchInventors: Ashutosh Anant Kelkar, Sunil Sopana Tonde, Sunil Sadashiv Divekar, Raghunath Vitthal Chaudhari
-
Patent number: 6420304Abstract: The invention relates to a polymer-supported carbonylation catalyst and its use in a process for preparing organic carboxylic acid or anhydride having n+1 carbon atoms. The invention relates also to a process for preparing organic carboxylic acid or anhydride having n+1 carbon atoms by carbonylating with monoxide, in the presence of the above-mentioned carbonylation catalyst, on alcohols having n carbon atoms, ethers having 2n carbon atoms or esters formed from said alcohols and acids. In particular, the invention relates to a process for preparing acetic acid by carbonylating methanol with carbon monooxide in the presence of said carbonylation catalyst. By using said carbonylation catalyst, the temperature for carbonylation can be lowered to about 160° C. with a reaction rate better than that of a traditional process, while the tendency of catalyst precipitation in the course of carbonylation can be improved also.Type: GrantFiled: April 20, 2000Date of Patent: July 16, 2002Assignee: China Petrochemical Development CorporationInventors: Chia-Jung Tsai, Yao-Lung Liu, Hsi-Chin Tsai
-
Patent number: 6395928Abstract: The present invention relates to an improved process for producing an organic carboxylic acid having (n+1) carbon atoms by reacting an alcohol having n carbon atoms with carbon monoxide in the presence of a rhodium catalyst system. More particularly, the present invention relates to carbonylation of alcohol such as methanol catalyzed by a rhodium system to produce acetic acid. The characteristic of the present invention is the addition of a catalyst stabilizer in the reaction medium to avoid or to alleviate the precipitation of the catalyst in the liquid phase. The catalyst as used herein is a an inorganic salt of alkaline metal having the following formula (A): XnMm (A) X=Li+, Na+, K+; M=CO3−2, HCO3−, PO4−3, HPO4−2, H2PO4−, SO4−2, HSO4−, C2O4−2, HC2O4−, B(C6Y5)4−1; Y=H, F or CF3.Type: GrantFiled: January 12, 2000Date of Patent: May 28, 2002Assignee: China Petrochemical Development CorporationInventors: Kuo-Chen Shih, Shu-Hei Wang, Tsu-Tseng Weng, Kou-Suein Ai
-
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
-
Patent number: 6380426Abstract: The present invention relates to a process for the preparation of a carboxylic acid by carbonylating the corresponding alcohol in carbon monoxide atmosphere and in the presence of water, a solvent, a palladium catalyst and a promoter system consisting of an organic or inorganic halide and an organic sulphonic acid, at a temperature in the range of 50-250° C., at a pressure in the range of 50-2000 psig for 1 to 10 hours, the concentration of the catalyst being one mole of catalyst per every 50-50000 moles of the alcohol, the amount of the organic or inorganic halide being in the range of 5-500 moles per mole of the catalyst, and the amount of the organic sulphonic acid being in the range of 5-500 moles per mole of the catalyst, collecting the resulting product.Type: GrantFiled: September 26, 2001Date of Patent: April 30, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Ashutosh A Kelkar, Sunil S Tonde, Raghunath V Chaudhari
-
Patent number: 6362366Abstract: There is provided a process control method for the production of acetic acid by the catalyzed carbonylation of methanol and a process for the manufacture of acetic acid using the process control method. The process control method comprises measuring various reactor component concentrations, specifically the active catalyst species, methyl iodide, water and methyl acetate by means of an infrared analyzer, and adjusting in response thereto the concentrations of at least the catalyst species, methyl iodide and water to optimize the acetic acid reaction.Type: GrantFiled: July 6, 2000Date of Patent: March 26, 2002Assignee: Millennium Petrochemicals IncInventors: Noel Hallinan, James A. Hinnenkamp
-
Publication number: 20020035291Abstract: A process for the production of oxygenated C2 hydrocarbons from cellulose is disclosed. The input cellulose waste is gasified using steam in the absence of air and the primary gaseous products of carbon monoxide and hydrogen are subjected to heat, pressure, and catalysts to form methyl alcohol. Carbon monoxide is added to the methyl alcohol and further subjected to heat, pressure and catalysts to form acetic acid. The acetic acid is purified using a distillation tower, and removed for sale. Output production is increased by adding further carbon monoxide and hydrogen from burners used to heat the gasifiers. Further carbon monoxide and hydrogen are also produced by steam gasification of the carbon residue to promote a water/gas shift. These gases are fed into the gas stream produced by the gasification of cellulose, and provide more feedstock for the reactions.Type: ApplicationFiled: March 6, 2001Publication date: March 21, 2002Inventors: Larry Jack Melnichuk, Karen Venita Kelly
-
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
-
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
-
Patent number: 6353132Abstract: 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 5 (vanadium, niobium, tantalum) 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 5, 2002Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
-
Patent number: 6353133Abstract: The retrofitting of an existing methanol or methanol/ammonia plant to make acetic acid is disclosed. The plant is retrofitted to feed carbon dioxide into a reformer to which natural gas and steam (water) are fed. Syngas is formed in the reformer wherein both the natural gas and the carbon dioxide are reformed to produce syngas with a large proportion of carbon monoxide relative to reforming without added carbon dioxide. The syngas is split into a first part and a second part. The first syngas part is converted to methanol in a conventional methanol synthesis loop that is operated at about half of the design capacity of the original plant. The second syngas part is processed to separate out carbon dioxide and carbon monoxide, and the separated carbon dioxide is fed back into the feed to the reformer to enhance carbon monoxide formation. The separated carbon monoxide is then reacted with the methanol to produce acetic acid or an acetic acid precursor by a conventional process.Type: GrantFiled: May 9, 2001Date of Patent: March 5, 2002Assignee: Acetex (Cyprus) LimitedInventors: Daniel Marcel Thiebaut, Kenneth Ebenes Vidalin
-
Patent number: 6346645Abstract: Carbonyl compounds (e.g. acetone and acetaldehyde) are often present as impurities in oxygenated organic liquids such as acetic acid made by the carbonylation of methanol or in phenol produced by the oxidation of cumene. These impurities can render petrochemical products unsuitable for long-term storage or otherwise adversely affect downstream processing operations. It has now been found that detrimental carbonyl impurities can be easily removed from oxygenated organic liquids by contact with resins having amine functional groups.Type: GrantFiled: April 18, 2000Date of Patent: February 12, 2002Assignee: UOP LLCInventors: Santi Kulprathipanja, David W. House, Peter R. Pujado
-
Patent number: 6346644Abstract: The present invention relates to an improved process for producing an organic carboxylic acid having (n+1) carbon atoms by reacting an alcohol having n carbon atoms with carbon monoxide in the presence of a rhodium catalyst system. More particularly, the present invention relates to carbonylation of alcohol such as methanol catalyzed by a rhodium system to produce acetic acid. The characteristic of the present invention is the addition of a catalyst stabilizer in the reaction medium to avoid or to alleviate the precipitation of the catalyst in the liquid phase. The catalyst stabilizer as used herein is a pyridine derivative having substituent(s) of such as (CH2)mCOOR or (CH2)mSO3R (R═H or hydrocarbons; m=0-6).Type: GrantFiled: January 12, 2000Date of Patent: February 12, 2002Assignee: China Petrochemical Development Corp.Inventors: Kuo-Chen Shih, Shu-Hei Wang, Tsu-Tseng Weng, Kou-Suein Ai
-
Patent number: 6339171Abstract: Disclosed is a method to manufacture high purity acetic acid. Although described in relation to that produced by a low water carbonylation process the present invention is applicable to other mechanisms for production of acetic acid which results in formation of permanganate reducing compounds such as acetaldehyde and its derivatives, and alkyl iodide impurities in intermediate process streams. It has been found that permanganate reducing compounds and alkyl iodides may be conveniently removed from a light phase of an intermediate stream in the reaction process by employing a multiple distillation process coupled with an optional post extraction of acetaldehyde. The distillation process involves first distilling a light phase to concentrate the permanganate reducing compounds, and in particular the acetaldehyde, and then separating the permanganate reducing compounds and alkyl iodides in a second distillation tower.Type: GrantFiled: May 3, 1999Date of Patent: January 15, 2002Assignee: Celanese International CorporationInventors: Madan Singh, George A. Blay, Michael L. Karnilaw, Melchior A. Meilchen, Robin Suzanne Tanke, G. Paull Torrence
-
Patent number: 6326455Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.Type: GrantFiled: April 5, 2001Date of Patent: December 4, 2001Assignee: RPC Inc.Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
-
Patent number: 6326515Abstract: A process for removing higher organic iodides, including hexyl iodide, from an acetic acid product obtained by carbonylating methanol and/or a reactive derivative thereof in the presence of a finite concentration of water, Group VIII noble metal catalyst, methyl iodide as co-catalyst, and optionally a catalyst promoter, which process includes the step of subjecting an aqueous composition comprising acetic acid and at least one higher organic iodide to distillation in a column, or section of a column, separating water overhead from a dry acetic acid fraction, wherein the water concentration on the feed tray of the column, or section of the column, is greater than 8% by weight and the water concentration in the head of the column, and/or section of the column, is greater than 70% by weight.Type: GrantFiled: September 8, 1999Date of Patent: December 4, 2001Assignee: BP Chemicals LimitedInventors: Kirsten Everald Clode, Derrick John Watson
-
Patent number: 6323364Abstract: The method of the present invention provides an improvement upon prior art methanol carbonylation methods which substantially reduces the production of carbonyl impurities. The production of carbonyl impurities, particularly acetaldehyde, crotonaldehyde, and 2-ethyl crotonaldehyde, in methanol carbonylation reactions has been found to decrease by maintaining less than about 4.5 wt % methyl iodide in the reaction medium during the course of the reaction.Type: GrantFiled: August 31, 1999Date of Patent: November 27, 2001Assignee: Celanese International CorporationInventors: Pramod Agrawal, Hung-Cheun Cheung, Darrell A. Fisher, Valerie Santillan, Mark O. Scates, Elaine C. Sibrel, G. Paul Torrence
-
Patent number: 6303813Abstract: The method of the present invention provides an improvement upon prior art methanol carbonylation methods which substantially reduces the production of carbonyl impurities. The production of carbonyl impurities, particularly acetaldehyde, crotonaldehyde, and 2-ethyl crotonaldehyde, in methanol carbonylation reactions has been found to decrease by maintaining a partial pressure of hydrogen between about 0.1 and 4 psia at reaction total pressure of from about 15 to about 40 atmospheres total reaction pressure.Type: GrantFiled: August 31, 1999Date of Patent: October 16, 2001Assignee: Celanese International CorporationInventors: Mark O. Scates, Valerie Santillan, Pramod Agrawal, G. Paull Torrence, R. Jay Warner
-
Patent number: 6294691Abstract: A process for manufacture of branched carboxylic acids from branched olefins by means of reaction with carbon monoxide and a solid acid catalyst, characterized in that a branched olefin, or a precursor thereof, is reacted in a batch reactor or a plug flow reactor with carbon monoxide and water, in the presence of an acidic ion exchanger, having sufficient acid groups to provide requisite protons for conversion of said olefin or a precursor of it, and carbon monoxide into branched carboxylic acids, and in the presence of a polar non-coordinating organic solvent.Type: GrantFiled: June 22, 1998Date of Patent: September 25, 2001Inventor: Jean-Paul Lange
-
Publication number: 20010023285Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.Type: ApplicationFiled: April 5, 2001Publication date: September 20, 2001Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
-
Patent number: 6274096Abstract: The retrofitting of an existing methanol or methanol/ammonia plant to make acetic acid is disclosed. The plant is retrofitted to feed carbon dioxide into a reformer to which natural gas and steam (water) are fed. Syngas is formed in the reformer wherein both the natural gas and the carbon dioxide are reformed to produce syngas with a large proportion of carbon monoxide relative to reforming without added carbon dioxide. The syngas is split into a first part and a second part. The first syngas part is converted to methanol in a conventional methanol synthesis loop that is operated at about half of the design capacity of the original plant. The second syngas part is processed to separate out carbon dioxide and carbon monoxide, and the separated carbon dioxide is fed back into the feed to the reformer to enhance carbon monoxide formation. The separated carbon monoxide is then reacted with the methanol to produce acetic acid or an acetic acid precursor by a conventional process.Type: GrantFiled: November 1, 1999Date of Patent: August 14, 2001Assignee: Acetex (Cyprus) LimitedInventors: Daniel Marcel Thiebaut, Kenneth Ebenes Vidalin
-
Publication number: 20010007911Abstract: The invention relates to a process for preparing N-acylglycine derivatives of the formula (III) 1Type: ApplicationFiled: July 7, 1999Publication date: July 12, 2001Inventors: HOLGER GEISSLER, SANDRA BOGDANOVIC, MATTHIAS BELLER, MARKUS ECKERT, FRANK VOLLMULLER
-
Patent number: 6255527Abstract: A method of controlling the carbon monoxide flow to a reactor wherein acetic acid is produced continuously by feeding carbon monoxide through a control valve and methanol and/or a reactive derivative thereof, there being maintained in the reactor a liquid reaction composition comprising at least 5% w/w methyl acetate, a finite concentration of water, from 1 to 30% w/w methyl iodide, a Group VIII noble metal catalyst, optionally at least one promoter and acetic acid comprising the remainder of the composition which method comprises the steps of: (i) measuring the carbon monoxide flow through the control valve; (ii) performing a background calculation to arrive at a time-averaged carbon monoxide flow rate; (iii) adding a constant value to the time-averaged carbon monoxide flow to arrive at a maximum allowable carbon monoxide flow rate; and (iv) feeding information comprising the calculated maximum allowable carbon monoxide flow rate to a control system which operates in a manner such that the carbon monoxidType: GrantFiled: September 3, 1999Date of Patent: July 3, 2001Assignee: BP Chemicals LimitedInventor: Michael James Muskett
-
Patent number: 6232352Abstract: The retrofitting of an existing methanol or methanol/ammonia plant to make acetic acid is disclosed. The existing plant has a reformer to which natural gas or another hydrocarbon and steam (water) are fed. Syngas is formed in the reformer. All or part of the syngas is processed to separate out carbon dioxide, carbon monoxide and hydrogen, and the separated carbon dioxide is fed either to the existing methanol synthesis loop for methanol synthesis, or back into the feed to the reformer to enhance carbon monoxide formation in the syngas. Any remaining syngas not fed to the carbon dioxide separator can be converted to methanol in the existing methanol synthesis loop along with carbon dioxide from the separator and/or imported carbon dioxide, and hydrogen from the separator. The separated carbon monoxide is then reacted with the methanol to produce acetic acid or an acetic acid precursor by a conventional process.Type: GrantFiled: April 12, 2000Date of Patent: May 15, 2001Assignee: Acetex limitedInventor: Kenneth Ebenes Vidalin
-
Patent number: 6211405Abstract: The present invention provides a process for the carbonylation of an alcohol, ether or ester to products comprising a carboxylic acid, the anhydride thereof or coproduction of the carboxylic acid and anhydride. More particularly, the present invention provides a process for the carbonylation of methanol to produce acetic acid by reacting methanol with carbon monoxide in a liquid reaction medium containing a catalyst comprising rhodium, iridium, iodide ion, and said reaction medium further comprising water, acetic acid, methyl iodide, and methyl acetate and subsequently recovering acetic acid from the resulting reaction product.Type: GrantFiled: October 23, 1998Date of Patent: April 3, 2001Assignee: Celanese International CorporationInventors: Hung-Cheun Cheung, Elaine C. Sibrel, Robin S. Tanke, G. Paull Torrence
-
Patent number: 6175039Abstract: A process for the production and purification of acetic acid by carbonylation of methanol, DME or reactive derivatives thereof in a distillation column containing a homogenous catalyst system.Type: GrantFiled: August 2, 1999Date of Patent: January 16, 2001Assignee: Haldor Topsoe A/SInventor: Bodil Voss
-
Patent number: 6160163Abstract: A method for the vapor-phase carbonylation of lower alkyl alcohols to esters and optionally, carboxylic acids using a catalyst having a platinum on a solid support material as a first component and a vaporous halide as a second component. Desirably, the catalyst includes platinum on an activated carbon support and the vaporous halide is selected from hydrogen halides, alkyl halides and aryl halides having up to 12 carbon atoms, and mixtures thereof.Type: GrantFiled: February 16, 1999Date of Patent: December 12, 2000Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
-
Patent number: 6153792Abstract: A process for the production of a carboxylic acid in the presence of solid catalyst particles that employs a flash step with a liquid wash is disclosed. This process helps prevent the buildup of deposits of solid catalyst particles, attrited solid catalyst particles, and heavy by-products in the flash zone. This invention is useful for the production of carboxylic acids, especially acetic acid.Type: GrantFiled: December 18, 1998Date of Patent: November 28, 2000Assignee: UOP LLCInventors: William A. Leet, Santi Kulprathipanja
-
Patent number: 6143930Abstract: Disclosed is a method to manufacture high purity acetic acid. Although described in relation to that produced by a low water carbonylation process the present invention is applicable to other mechanisms for production of acetic acid which results in formation of permanganate reducing compounds such as acetaldehyde, propionic acid, and alkyl iodide impurities in intermediate process streams. It has been found that permanganate reducing compounds and alkyl iodides may be conveniently removed from a light phase of an intermediate stream in the reaction process by employing a multiple distillation process coupled with an optional extraction of acetaldehyde. The distillation process involves first distilling a light phase to concentrate the permanganate reducing compounds, and in particular the acetaldehyde, and then separating the permanganate reducing compounds and alkyl iodides in a second distillation tower.Type: GrantFiled: October 17, 1997Date of Patent: November 7, 2000Assignee: Celanese International CorpInventors: Madan Singh, George A. Blay, Michael L. Karnilaw, Melchior A. Meilchen, Wayne David Picard, Valerie Santillan, Mark O. Scates, Robin Suzanne Tanke, G. Paull Torrence, Richard F. Vogel, Jr., R. Jay Warner
-
Patent number: 6140535Abstract: A process as provided for producing an acetic acid process stream having less than 400 ppm propionic acid and less than 1500 ppm water. Methanol or a reactive derivative thereof and carbon monoxide is fed to a carbonylation reactor in which there is maintained during the course of the process a liquid reaction composition containing an iridium carbonylation catalyst, methyl iodide co-catalyst, a promoter, water at a concentration of less than about 8% by weight, methyl acetate, acetic acid, and propionic acid by-product and its precursors. Liquid reaction composition is withdrawn from the carbonylation reactor and introduced to a flash zone to form a vapor fraction comprising water, acetic acid product, propionic acid by-product, methyl acetate, methyl iodide and propionic acid precursors, and a liquid fraction comprising involatile iridium catalyst, involatile optional promoter or promoters, acetic acid and water.Type: GrantFiled: December 17, 1997Date of Patent: October 31, 2000Assignee: BP Chemicals LimitedInventor: Bruce L Williams
-
Patent number: 6137000Abstract: A vapor phase process for the carbonylation of lower alkyl alcohols to esters and optionally, carboxylic acids using a catalyst containing iridium and at least one second metal selected from the Lanthanide Series. 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 process is useful for preparing acetic acid, methyl acetate or a mixture thereof by contacting the catalyst with a vapor comprising methanol, a halide and carbon monoxide under carbonylation process conditions.Type: GrantFiled: February 16, 1999Date of Patent: October 24, 2000Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver