Halogen Containing Catalyst, Initiator, Or Promoter Utilized Patents (Class 562/416)
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Patent number: 7572936Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: August 11, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede
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Patent number: 7568361Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: August 4, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Robert Lin, Marcel de Vreede, Lee Reynolds Partin
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Patent number: 7566802Abstract: This invention relates to a process for the manufacture of aromatic carboxylic acids by exothermic liquid phase oxidation of an aromatic feedstock. More particularly, this invention relates to the efficient energy recovery of the exotherm produced by the liquid phase oxidation of an aromatic feedstock. Also, this invention relates to the efficient energy recovery of the exotherm produced by the liquid phase oxidation of an aromatic feedstock while also utilizing the heat from the energy of oxidation to efficiently remove water resulting from the exothermic oxidation reaction.Type: GrantFiled: May 24, 2006Date of Patent: July 28, 2009Assignee: Eastman Chemical CompanyInventors: Timothy Alan Upshaw, Ronald Buford Sheppard
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Patent number: 7557243Abstract: A process is provided for producing an enriched carboxylic acid compositions produced by contacting composition comprising a carboxylic acid with an enrichment feed in an enrichment zone to form an enriched carboxylic acid composition. This invention also relates to a process and the resulting compositions for removing catalyst from a carboxylic acid composition to produce a post catalyst removal composition.Type: GrantFiled: March 1, 2006Date of Patent: July 7, 2009Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker, Ronald Buford Sheppard
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Patent number: 7556784Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically producing aromatic discarboxylic acids. The process reduces costs associated with hydrogenation by forming a final composite product containing unhydrogenated acid particles.Type: GrantFiled: March 18, 2008Date of Patent: July 7, 2009Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede
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Patent number: 7546747Abstract: The present invention relates to a process by which a dried carboxylic acid cake is obtained from a slurry or cake carboxylic acid product through the use of at least one counter current wash. More specifically, the present invention relates to a process by which a dried terephthalic acid cake suitable as a starting material for polyester or co-polyester production is obtained from a slurry or cake terephthalic acid product through the use of at least one counter current wash.Type: GrantFiled: January 15, 2004Date of Patent: June 16, 2009Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Robert Lin, Philip Edward Gibson
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Patent number: 7541489Abstract: A method of preparing a halophthalic acid is disclosed which comprises the steps of contacting in a liquid phase reaction mixture at least one halogen-substituted ortho-xylene with oxygen and acetic acid at a temperature in a range between about 120° C. and about 220° C. in the presence of a catalyst system yielding a product mixture comprising less than 10 percent halogen-substituted ortho-xylene starting material, a halophthalic acid product, and less than about 10,000 ppm halobenzoic acid and less than about 1000 ppm halophthalide by-products based on a total amount of halophthalic acid present in the product mixture. In addition methods for the preparation of halophthalic anhydride, and recovery of high purity acetic acid from an aqueous acetic acid stream comprising HCl, which is generated during the preparation of the halophthalic acid are also disclosed.Type: GrantFiled: June 29, 2005Date of Patent: June 2, 2009Assignee: SABIC Innovative Plastics IP B.V.Inventors: Robert Edgar Colborn, David Bruce Hall, Peter Alois Koch, Bernd Volker Demuth, Thomas Wessel, KarlErnst Mack, Prashant Anil Tatake, Utpal Mahendra Vakil, Shyamal Bhaskar Gondkar, John Edward Pace, Kwang Woong Won
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Patent number: 7507856Abstract: The present invention relates to a process for the oxidation of hydrocarbons, in particular of branched or unbranched saturated aliphatic hydrocarbons, of cycloaliphatic or alkylaromatic hydrocarbons or of alcohols and/or ketones, to acid or polyacid compounds. It relates more particularly to the oxidation, by an oxidizing agent comprising molecular oxygen, of cyclohexane and/or of cyclohexanol and/or cyclohexanone to adipic acid, in the presence of an aromatic organic acid and a manganese-based catalyst. The yield and selectivity for adipic acid are of a high level with respect to those obtained with other solvents and catalysts.Type: GrantFiled: July 15, 2002Date of Patent: March 24, 2009Assignee: Rhodia Polyamide IntermediatesInventors: Didier Bonnet, Eric Fache, Jean-Pierre Simonato
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Patent number: 7504535Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: March 17, 2009Assignee: Eastman Chemical CompanyInventors: Marcel de Vreede, Alan George Wonders, Robert Lin
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Publication number: 20090062563Abstract: The present invention relates to a process for making terephthalic acid by reacting a starting material and oxygen in the presence of a heterogeneous catalyst and p-xylene as solvent to produce a solution of terephthalic acid (TPA). The starting material is p-xylene, p-toluic acid, 4 carboxybenzaldehyde, or a mixture of any two or more thereof. No solid TPA is formed during the reaction in contrast to previous manufacturing methods that utilize acidic solvents and precipitate TPA as it forms. By avoiding the direct precipitation of TPA during formation, the present methods avoid many shortcomings of the conventional manufacturing methods used to produce TPA. In particular, the present methods do not require additional purification steps to remove reaction byproducts; film grade TPA can be obtained directly from starting material in a one-step process.Type: ApplicationFiled: December 20, 2005Publication date: March 5, 2009Inventors: Johannes Maria Franciscus Sijben, Herman Jozef Claudius De Meyer
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Patent number: 7498003Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: August 29, 2007Date of Patent: March 3, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Lee Reynolds Partin, Wayne Scott Strasser, Marcel deVreede, Puneet Gupta
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Patent number: 7498002Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: August 29, 2007Date of Patent: March 3, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Howard Wood Jenkins, Jr., Lee Reynolds Partin, Wayne Scott Strasser, Marcel deVreede
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Patent number: 7494641Abstract: Disclosed is a process that relates to the recovery of a metal catalyst from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic acid. The process involves the addition of a wash solution to a high temperature molten dispersion to recover the metal catalyst and then subjecting an aqueous mixture or purified aqueous mixture so formed to a single stage extraction to remove organic impurities to produce an extract stream and a raffinate stream comprising the metal catalyst.Type: GrantFiled: September 23, 2004Date of Patent: February 24, 2009Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede
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Patent number: 7495125Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: February 24, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede
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Patent number: 7491369Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: August 29, 2007Date of Patent: February 17, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Thomas Earl Woodruff, Ronald Buford Sheppard, Wayne Scott Strasser
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Publication number: 20090043124Abstract: Trimellitic acid is produced by oxidation of pseudocumene in acetic acid at temperatures between 130 and 240° C. in the presence of a catalyst composition containing cobalt, manganese and bromine. The process comprises the stages of: (i) simultaneously feeding pseudocumene and air or an oxygen-containing gas into a solution containing acetic acid and the catalyst composition, at an addition rate resulting in an oxygen concentration in the off-gas of less than 8 vol %, and at a temperature and a pressure sufficient to result in 5 to 25 mol % of the total amount of oxygen required to oxidize the pseudocumene to trimellitic acid being consumed, and (ii) feeding air or an oxygen-containing gas into the reaction mixture obtained in stage (i) until essentially all of the pseudocumene has been consumed and a molar yield of trimellitic acid of at least 90% has been obtained. There is no supplementation of catalyst after stage (i).Type: ApplicationFiled: May 6, 2006Publication date: February 12, 2009Inventors: Gian Luca Castiglioni, Roberto Pirola, Carlo Fumagalli
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Patent number: 7485747Abstract: Disclosed is a process for producing a benzenedicarrboxylic acid such as terephthalic acid wherein a dialkyl benzene compound and acetic acid having catalyst components dissolved therein are fed to a first reaction zone wherein the dialkyl benzene compound is oxidized with molecular oxygen to provide a first oxidation zone product comprising a benzenedicarboxylic acid containing minor amounts of mono-carboxylic acid by-products such as carboxybenzaldehyde and toluic acid. The first oxidation zone product comprising a slurry of a benzenedicarboxylic acid containing minor amounts of mono-carboxylic acid by-products is fed to a second oxidation reaction zone that is operated under more severe conditions of temperature and pressure. The rate of the feed of a molecular oxygen containing gas to the second oxidation zone is about 3% or less of the the rate of the feed of the molecular oxygen containing gas to the first oxidation zone.Type: GrantFiled: May 28, 2002Date of Patent: February 3, 2009Assignee: Eastman Chemical CompanyInventors: Ronald Buford Sheppard, Charles Edwan Sumner, Jr., Brent Alan Tennant
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Patent number: 7485746Abstract: A process for oxidation with oxygen of at least one aromatic hydrocarbon having oxidizable, substituents that maximizes the utilization of oxygen without reduction in the quality of the carboxylic acid products produced by means of a stagewise countercurrent oxidation system is disclosed.Type: GrantFiled: November 14, 2003Date of Patent: February 3, 2009Assignee: BP Corporation North America Inc.Inventors: Frank G. Belmonte, David L. Sikkenga, Olusola Sunday Ogundiran, Kenneth J. Abrams, Linus Kai-Wah Leung, Christopher G. Meller, Dale A. Figgins, Allen B. Mossman
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Patent number: 7482482Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: January 27, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Marcel de Vreede, Lee Reynolds Partin, Wayne Scott Strasser
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Patent number: 7465824Abstract: A process is disclosed for producing at least one high purity aromatic carboxylic acid by oxidizing an aromatic feedstock with oxygen in a reaction medium comprising the aromatic feedstock, a promoter, a heavy metal catalyst, and a solvent which comprises benzoic acid and water to produce a reactor effluent wherein substantially all of the aromatic carboxylic acid produced remains in solution; and then hydrogenating the reactor effluent in the presence of a catalyst and hydrogen. This process efficiently and effectively produces high purity aromatic carboxylic acids by utilizing a common solvent for both oxidation and purification and eliminating the need for intermediate process steps and equipment.Type: GrantFiled: February 8, 2007Date of Patent: December 16, 2008Assignee: BP Corporation North America Inc.Inventors: Carolyn E. Schmit, David L. Sikkenga, Christopher G. Meller
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Publication number: 20080293964Abstract: The present invention relates to a process for preparing high purity terephthalic acid by catalytic, liquid phase oxidation of p-xylene utilizing a partially homogeneous reaction in the presence of a very specific catalyst. The process produces a high purity terephthalic acid without the secondary purification step currently practiced.Type: ApplicationFiled: December 9, 2005Publication date: November 27, 2008Inventors: Milan Hronec, Hussain Al Ghatta, Roberto Ruggieri
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Publication number: 20080242887Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: ApplicationFiled: May 7, 2008Publication date: October 2, 2008Applicant: EASTMAN CHEMICAL COMPANYInventors: Alan George Wonders, Wayne Scott Strasser, Marcel de Vreede, J. Thomas Tidwell
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Publication number: 20080194866Abstract: A process is disclosed for producing at least one high purity aromatic carboxylic acid by oxidizing an aromatic feedstock with oxygen in a reaction medium comprising the aromatic feedstock, a promoter, a heavy metal catalyst, and a solvent which comprises benzoic acid and water to produce a reactor effluent wherein substantially all of the aromatic carboxylic acid produced remains in solution; and then hydrogenating the reactor effluent in the presence of a catalyst and hydrogen. This process efficiently and effectively produces high purity aromatic carboxylic acids by utilizing a common solvent for both oxidation and purification and eliminating the need for intermediate process steps and equipment.Type: ApplicationFiled: February 8, 2007Publication date: August 14, 2008Applicant: BP Corporation North America Inc.Inventors: Carolyn E. Schmit, David L. Sikkenga, Christopher G. Meller
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Patent number: 7410632Abstract: A method for removing impurities from a mother liquor comprising a carboxylic acid, a metal catalyst, impurities by (a) evaporating the mother liquor comprising a carboxylic acid, the metal catalyst, impurities, water and a solvent in a first evaporator zone to produce a vapor stream and a concentrated mother liquor stream; (b) evaporating the concentrated mother liquor stream in a second evaporator zone to form a solvent rich stream and a super concentrated mother liquor stream; (c) separating organic impurities with a water-solvent solution from the super concentrated mother liquor in a solid-liquid separation zone to form an aqueous stream and a second aqueous stream; (d) mixing in a mixing zone water and optionally and extraction solvent with the aqueous stream and second aqueous stream to form an aqueous mixture; and (e) adding an extraction solvent to the aqueous mixture in an extraction zone to form an extract stream and a raffinate stream.Type: GrantFiled: June 5, 2003Date of Patent: August 12, 2008Assignee: Eastman Chemical CompanyInventor: Robert Lin
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Patent number: 7399882Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: July 15, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Howard Wood Jenkins, Jr., Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede
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Patent number: 7390921Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: June 24, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Marcel de Vreede, Lee Reynolds Partin, Wayne Scott Strasser, Puneet Gupta
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Patent number: 7381386Abstract: A method for removing impurities from a mother liquor comprising a carboxylic acid, a metal catalyst, impurities by (a) evaporating the mother liquor comprising a carboxylic acid, a metal catalyst, impurities and a solvent in a first evaporator zone to produce a vapor stream and a concentrated mother liquor stream; (b) evaporating the concentrated mother liquor stream in a second evaporator zone to form a solvent rich stream and a super concentrated mother liquor stream; (c) mixing in a mixing zone a water-solvent solution and optionally an extraction solvent with the super concentrated mother liquor stream to form an aqueous mixture; (d) optionally separating organic impurities from the aqueous mixture in a solid-liquid separation zone to form a purified aqueous mixture; and (e) extracting the aqueous mixture or purified aqueous mixture with an extraction solvent in an extraction zone to form an extract stream and the raffinate stream.Type: GrantFiled: June 5, 2003Date of Patent: June 3, 2008Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede
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Patent number: 7381836Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: June 3, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede, Puneet Gupta
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Patent number: 7378544Abstract: The present invention relates to the liquid phase oxidation of aromatic hydrocarbons in the presence of at least one heavy metal oxidation catalyst and bromine, which is activated by at least one of anthracene or another polycyclic aromatic compound to produce aromatic carboxylic acids.Type: GrantFiled: November 3, 2004Date of Patent: May 27, 2008Assignee: BP Corporation North America Inc.Inventors: Wayne P. Schammel, Victor A. Adamian, Yenamandra Viswanath, Igor V. Zakharov
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Patent number: 7371866Abstract: A process for catalytically oxidizing alkylaromatic compounds of the formula (I) Ar—CH2—R where Ar is an optionally substituted, aromatic or heteroaromatic 5-membered or 6-membered ring or a ring system having up to 20 carbon atoms where Ar may optionally be fused to a C1-C6-alkyl group in which up to 2 carbon atoms may be replaced by a heteroatom, and R is hydrogen, phenyl, benzyl or heteroaryl, where the phenyl, benzyl or heteroaryl radicals may also be joined to Ar by a bridge, or R together with Ar forms an optionally substituted ring system which may contain one or more optionally substituted heteroatoms, to the corresponding aromatic or heteroaromatic carboxylic acids in a solvent with ozone in the presence of a transition metal catalyst and optionally in the presence of an acid at a temperature between ?70° C. and 110° C. to the corresponding carboxylic acid.Type: GrantFiled: May 15, 2003Date of Patent: May 13, 2008Assignee: DSM Fine Chemicals Austria Nfg GmbH & Co KGInventors: Walther Jary, Peter Poechlauer, Thorsten Ganglberger
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Patent number: 7371894Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: May 13, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Marcel de Vreede, Lee Reynolds Partin, Wayne Scott Strasser
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Patent number: 7361784Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: June 16, 2005Date of Patent: April 22, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Gino Georges Lavoie, Charles Edwan Sumner, Jr.
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Patent number: 7358392Abstract: Disclosed is a process to produce a purified carboxylic acid slurry. The process comprises removing impurities from a crystallized product in a solid liquid displacement zone to form the purified carboxylic acid slurry. The process produces purified carboxylic acid slurry having good color and low impurity levels without the use of purification steps like hydrogenation or an impurity removal process.Type: GrantFiled: February 2, 2006Date of Patent: April 15, 2008Assignee: Eastman Chemical CompanyInventors: Ronald Buford Sheppard, Brent Alan Tennant, Thomas Earl Woodruff, Robert Lin, Ruairi Seosamh O'Meadhra
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Patent number: 7358389Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: March 1, 2006Date of Patent: April 15, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Thomas Earl Woodruff, Ronald Buford Sheppard, Wayne Scott Strasser
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Patent number: 7355068Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: March 1, 2006Date of Patent: April 8, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Thomas Earl Woodruff, Ronald Buford Sheppard, Wayne Scott Strasser
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Patent number: 7348452Abstract: A method for liquid phase oxidation of p-xylene with molecular oxygen to terephthalic acid that minimizes solvent loss through solvent burn and minimizes the formation of incomplete oxidation products such as 4-carboxybenzaldehyde (4-CBA). P-xylene is oxidized at a temperature in the range of 120° C. to 250° C. and in the presence of a source of molecular oxygen and a catalyst composition substantially free of zirconium atoms comprising a source of nickel (Ni) atoms, a source of manganese (Mn) atoms, and a source of bromine (Br) atoms, to form a crude reaction mixture comprising terephthalic acid and incompletely oxidized reaction products comprising 4-CBA, wherein the stoichiometric molar ratio of bromine atoms to manganese atoms is 1.5 or less, and the amount of nickel atoms is at least 500 ppm.Type: GrantFiled: April 22, 2004Date of Patent: March 25, 2008Assignee: Eastman Chemical CompanyInventor: Gino Georges Lavoie
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Patent number: 7276625Abstract: In this invention, a process is provided by which a carboxylic acid/diol mixture suitable as starting material for a polyester production is obtained from a decolorized carboxylic acid solution without isolation of a substantially dry carboxylic acid solid. More specifically, in this invention, a process is provided by which a terephthalic acid/ethylene glycol mixture suitable as starting material for a polyester production is obtained from a decolorized terephthalic acid solution without isolation of a substantially dry terephthalic acid solid.Type: GrantFiled: October 15, 2002Date of Patent: October 2, 2007Assignee: Eastman Chemical CompanyInventor: Robert Lin
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Patent number: 7238833Abstract: A process for the production of an aromatic carboxylic acid comprising contacting in the presence of a catalyst, within a continuous flow reactor, one or more precursors of the aromatic carboxylic acid with an oxidant, such contact being effected with said precursor(s) and the oxidant in an aqueous solvent comprising water under supercritical conditions or near supercritical conditions close to the supercritical point such that said one or more precursors, oxidant and aqueous solvent constitute a substantially single homogeneous phase in the reaction zone, wherein the contact of at least part of said precursor with said oxidant is contemporaneous with contact of said catalyst with at least part of said oxidant.Type: GrantFiled: April 28, 2004Date of Patent: July 3, 2007Assignee: Invista North America S.A.R.L.Inventors: Derek Alexander Graham, Paul Anthony Hamley, Raymond Oliver, Martyn Poliakoff, Duncan C. Woodcock, Thomas Iikenhans
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Patent number: 7196215Abstract: Disclosed is a process for the production of terephthalic acid by a plurality of process steps including the catalyst oxidation of a dialkylbenzene compound, a second oxidation, a hydrogenation of the product of the second oxidation, and crystallization of the hydrogenation terephthalic acid using a plurality of series-connected crystallizers.Type: GrantFiled: May 31, 2002Date of Patent: March 27, 2007Assignee: Eastman Chemical CompanyInventors: Robert Lin, Ruairi Seosamh O'Meadhra, Ronald Buford Sheppard
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Patent number: 7173149Abstract: A process for preparing alkynecarboxylic acids includes the oxidation of an alkyne alcohol with a hypohalite in the presence of a nitroxyl compound at a pH of greater than 7 with continual addition of the alkyne alcohol and of the hypohalite to the reaction mixture.Type: GrantFiled: September 22, 2003Date of Patent: February 6, 2007Assignee: Consortium für elektrochemische Industrie GmbHInventors: Jürgen Stohrer, Elke Fritz-Langhals, Christian Brüninghaus
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Patent number: 7161027Abstract: Disclosed is a process to produce a purified carboxylic acid slurry. The process comprises removing impurities from a crystallized product in a solid liquid displacement zone to form the purified carboxylic acid slurry. The purified carboxylic acid slurry is further cooled in a cooling zone and subsequently filtered and dried in a filtration and drying zone. The process produces purified carboxylic acid product having good color and low impurity levels without the use of purification steps like hydrogenation or filtrate purge.Type: GrantFiled: August 21, 2003Date of Patent: January 9, 2007Assignee: Eastman Chemical CompanyInventors: Ronald Buford Sheppard, Brent Alan Tennant, Thomas Earl Woodruff, Robert Lin
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Patent number: 7132566Abstract: Disclosed is a process to produce a purified carboxylic acid product. The process comprises removing impurities from a crude carboxylic acid slurry in a solid-liquid displacement zone to form a slurry product. The slurry product if further treated in a staged oxidation zone and a crystallization zone to from a crystallized product. The crystallized product is further cooled in a cooling zone and subsequently filtered and dried in a filtration and drying zone. The process produces purified carboxylic acid product having good color and low impurity levels without the use of purification steps like hydrogenation.Type: GrantFiled: September 22, 2003Date of Patent: November 7, 2006Assignee: Eastman Chemical CompanyInventors: Charles Edwan Sumner, Jr., Philip Edward Gibson, Robert Lin, Eric Jackson Fugate, Ernest William Arnold
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Patent number: 7060853Abstract: The present invention relates to a method for increasing the production capacity of a conventional oxidation reactor for catalytic liquid phase oxidation of paraxylene by staging the oxidation reaction into a first high pressure and high solvent ratio reaction zone followed by the conventional reactor.Type: GrantFiled: March 21, 2003Date of Patent: June 13, 2006Assignee: Invista North America S.a r.l.Inventors: Samuel Duncan Housley, John A. Turner
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Patent number: 6949673Abstract: Improved process for producing aromatic carboxylic acids by catalytic liquid phase oxidation of a corresponding precursor in a suitable solvent comprising feeding the reactants to a first oxidation reaction zone at high pressure and high solvent ratio, wherein uptake of oxygen is less than that required for full conversion of the precursor to its corresponding carboxylic acid, and then feeding the resulting reaction medium to a second oxidation reaction zone.Type: GrantFiled: March 21, 2003Date of Patent: September 27, 2005Assignee: E.I. Du Pont de Nemours and CompanyInventors: Samuel Duncan Housley, John A Turner
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Patent number: 6852879Abstract: Disclosed is a method and solvent composition capable of removing iron oxide deposits from the surface of titanium components without substantially damaging the underlying titanium component. Iron oxide deposits may be removed from the surface of a titanium component by contacting the titanium component with the solvent composition of the invention. The solvent composition may then be removed from contact with the titanium component to obtain a recyclable solvent composition which is recycled into repeated contact with the titanium component. The solvent composition comprises an aqueous mixture of an organic acid and a hydrohalide acid.Type: GrantFiled: September 26, 2002Date of Patent: February 8, 2005Assignee: BP Corporation North America Inc.Inventors: Frank G. Belmonte, Kenneth J. Abrams, James Delaney, Jr., Scott G. Kramer, David L. Sikkenga
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Patent number: 6759550Abstract: The present invention pertains to an improved method of oxidizing substituted aromatic compounds (such as p xylene) to their corresponding aromatic acids (such as terephthalic acid). The improvement involves carrying out the oxidation reaction in an aqueous medium, wherein the aqueous medium contains at least 30 percent water, preferably up to 30 percent surfactant and preferably a low molecular weight material containing a hydrophilic end group as a co-surfactant. The reaction is carried out at a pH of less than 3.0.Type: GrantFiled: November 13, 2002Date of Patent: July 6, 2004Assignee: The Dow Chemical CompanyInventors: John Klier, Christopher J. Tucker, Thomas H. Kalantar, Kenneth A. Burdett, Daniel Patrick Green, Luciano Piras, Sergio Schena, Guo-shuh John Lee
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Patent number: 6747171Abstract: A process for purifying a naphthalenic carboxylic acid comprising contacting at a temperature below about 575° F. a mixture comprising an impure naphthalenic carboxylic acid and a solvent in the presence of hydrogen gas with a noble metal on carbon catalyst. The process results in reduced amounts of organic impurities in the purified acid when compared to other purification processes.Type: GrantFiled: February 1, 2001Date of Patent: June 8, 2004Assignee: BP Corporation North America Inc.Inventor: Bruce I. Rosen
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Patent number: 6730808Abstract: Reactor membranes for used in oxidation reactions of hydrocarbons involving oxygen comprising a selective oxidation catalyst on a mixed conducting, oxide ion selective ceramic membrane of the composition (Sr1-xCax)1-yAyMn1-zBzO3-&dgr;, where A is Ba, Pb, Na, K, Y, an element of the lanthanide group or a combination thereof, B is Mg, Al, Ga, In, Sn, an element of the 3d or 4d period or a combination thereof, x is from 0.2 to 0.8, y is from 0 to 0.4, z is from 0 to 0.6, and &dgr; is a number, dependent on x, y and z, that renders the composition charge neutral.Type: GrantFiled: May 23, 2002Date of Patent: May 4, 2004Assignee: BASF AktiengesellschaftInventors: Stefan Bitterlich, Hartwig Voss, Hartmut Hibst, Andreas Tenten, Ingolf Voigt, Ute Pippardt
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Patent number: 6717009Abstract: A high-purity naphthalenedicarboxylic acid is produced by a method including Steps [1] and [2]: In Step [I], a raw mixture of crude terephthalic acid and crude naphthalenedicarboxylic acid is dissolved into high-temperature high-pressure water to form a dibasic acid solution wherein the crude naphthalenedicarboxylic acid content is 0.1 to 10 mass percent of the crude terephthalic acid content, the dibasic acid solution is brought into contact with hydrogen in the presence of a catalyst. In Step [II], the resultant in the dibasic acid solution is crystallized by multiple stages while the temperature and the pressure are reduced for each stage, and acid mixtures containing enriched naphthalenedicarboxylic acid or enriched terephthalic acid are obtained by solid-liquid separation.Type: GrantFiled: October 7, 2002Date of Patent: April 6, 2004Assignee: Kabushiki Kaisha Kobe Seiko Sho (Kobe Steel, Ltd.)Inventors: Masahiro Motoyuki, Tomoki Uemura, Koji Yamamoto
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Patent number: 6689903Abstract: Disclosed is a method for the recovery of crystalline terephthalic acid containing less than about 150 ppmw p-toluic acid by subjecting a solution of terephthalic acid containing minor amounts of p-toluic acid to crystallization in a crystallization zone comprising a plurality of series-connected crystallizers wherein the solution is subjected to rate-controlled evaporative cooling by sequential reduction in pressure and temperature to cause crystallization of terephthalic acid, wherein the pressure of the solution at the end of the crystallization zone is about ambient pressure or less. Solvent which is evaporated from the crystallizers is collected and condensed and the condensed solvent is returned to the crystallization zone at a point subsequent to the crystallizer from which it was obtained.Type: GrantFiled: May 30, 2002Date of Patent: February 10, 2004Assignee: Eastman Chemical CompanyInventors: Ruairi Seosamh O'Meadhra, Robert Lin, Shane Kipley Kirk, Brian David McMurray