With Recycle Or Recovery Of Reaction Component Patents (Class 562/414)
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Patent number: 11220730Abstract: Undercooled liquid metallic core-shell particles, whose core is stable against solidification at ambient conditions, i.e. under near ambient temperature and pressure conditions, are used to join or repair metallic non-particulate components. The undercooled-shell particles in the form of nano-size or micro-size particles comprise an undercooled stable liquid metallic core encapsulated inside an outer shell, which can comprise an oxide or other stabilizer shell typically formed in-situ on the undercooled liquid metallic core. The shell is ruptured to release the liquid phase core material to join or repair a component(s).Type: GrantFiled: March 12, 2019Date of Patent: January 11, 2022Assignee: Iowa State University Research Foundation, Inc.Inventors: Martin Thuo, Ian Tevis
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Patent number: 10843995Abstract: A process for manufacturing a carboxylic acid is provided, in one aspect, the process comprises oxidizing a feedstock comprising a substituted aromatic hydrocarbon to form a liquid-phase aromatic carboxylic acid; crystallizing at least a portion of the liquid-phase aromatic carboxylic acid in the presence of oxygen and an oxidation catalyst in a first crystallizer to form solid aromatic carboxylic acid, under reaction conditions suitable to oxidize unreacted feedstock to form additional aromatic carboxylic acid; and crystallizing at least a portion of the first crystallization effluent in the presence of oxygen and an oxidation catalyst in a second crystallizer to form additional solid aromatic carboxylic acid, under reaction conditions suitable to oxidize unreacted feedstock to form additional aromatic carboxylic acid, wherein the oxygen is present in a gaseous phase inside the second crystallizer in an amount of no more than 11% by volume on a dry basis.Type: GrantFiled: June 19, 2018Date of Patent: November 24, 2020Assignee: BP Corporation North America Inc.Inventor: Anders Bitsch-Larsen
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Patent number: 10435799Abstract: A carboxylic acid-containing composition, which composition contains an aldehyde, is purified in a process, which process comprises introducing the carboxylic acid-containing composition and an aqueous electrolyte into an electrolytic cell comprising electrodes; electrochemically oxidizing the aldehyde in the electrolytic cell to obtain an electrochemically oxidized product composition comprising a carboxylic acid derived from the aldehyde; and, optionally, separating carboxylic acid from the electrochemically oxidized product composition.Type: GrantFiled: May 20, 2016Date of Patent: October 8, 2019Assignee: Avantium Knowledge Centre B.V.Inventors: Klaas Jan Pieter Schouten, Jan Cornelis Van Der Waal, Maria Varini, Gerardus Johannes Maria Gruter
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Patent number: 10273198Abstract: A solvent exchanger and a method is provided for: pressurizing a CTA slurry into a solvent exchanger for separation and obtaining a mother liquor, a bias flow mother liquor and a suspended matter A; washing the suspended matter A to obtain a primary filtrate, a bias flow primary filtrate and a suspended matter B; washing the suspended matter B to obtain a secondary filtrate, a bias flow secondary filtrate and a suspended matter C; washing the suspended matter C to obtain a tertiary filtrate, a bias flow tertiary filtrate and a suspended matter D; washing the suspended matter D to obtain a fourth filtrate, a bias flow fourth filtrate and a suspended matter E; washing the suspended matter E to obtain a fifth filtrate, a bias flow fifth filtrate and a filter cake; and after finished, back-flushing the filter cake and then pulping to obtain a slurry, and discharging.Type: GrantFiled: January 9, 2015Date of Patent: April 30, 2019Assignee: TIANHUA INSTITUTE OF CHEMICAL MACHINERY AND AUTOMATION CO., LTDInventors: Xu Zhao, Wanyao Zhang, Zhongxin Sun, Yongpeng Tan, Xiangnan Zhai, Tianbao Wang, Yuanyue Liang, Guohai Zhang, Xiaopeng Feng, Yanshun Shen
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Patent number: 10156801Abstract: A toner, including: a colorant; a binder resin; and a releasing agent, wherein the binder resin includes a polyester resin, and the toner satisfies requirements (1) and (2) below: (1): G?(50)?3.0×107 Pa and 1.0×105 Pa?G?(60)?1.0×107 Pa, where G?(50) is a storage modulus at 50° C. of the toner and G?(60) is a storage modulus at 60° C. of the toner; and (2): a spin-spin relaxation time of the toner at 50° C. measured by solid echo method of pulse NMR is 1.0 ms or shorter.Type: GrantFiled: August 13, 2014Date of Patent: December 18, 2018Assignee: Ricoh Company, Ltd.Inventors: Kohsuke Nagata, Shinya Nakayama, Tsuyoshi Sugimoto, Daisuke Asahina, Susumu Chiba
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Patent number: 9550712Abstract: The invention provides a method for preparing a carboxylic acid, which method includes the steps of providing magnesium carboxylate, wherein the carboxylic acid corresponding with the carboxylate has a solubility in water at 20° C. of 80 g/100 g water or less; acidifying the magnesium carboxylate with HCl, thereby obtaining a solution comprising carboxylic acid and magnesium chloride (MgCl2); optionally a concentration step, wherein the solution comprising carboxylic acid and MgCl2 is concentrated; precipitating the carboxylic acid from the solution comprising the carboxylic acid and MgCl2, thereby obtaining a carboxylic acid precipitate and a MgCl2 solution.Type: GrantFiled: August 16, 2012Date of Patent: January 24, 2017Assignee: PURAC BIOCHEM B.V.Inventors: André Banier De Haan, Jan Van Breugel, Paulus Loduvicus Johannes Van Der Weide, Peter Paul Jansen, José María Vidal Lancis, Augustín Cerdà Baró
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Patent number: 9422219Abstract: Processes for manufacturing a purified aromatic carboxylic acid include heating a purification reaction mixture in a pre-heating zone, the purification reaction mixture comprising a crude aromatic carboxylic acid and a solvent, and purifying the crude aromatic carboxylic acid in the purification reaction mixture to form a purified aromatic carboxylic acid product. One or more operations are maintained at a pressure above ambient in order to achieve energy savings.Type: GrantFiled: December 30, 2014Date of Patent: August 23, 2016Assignee: BP Corporation North America Inc.Inventor: Thomas M. Bartos
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Patent number: 9415371Abstract: A multi-phase reactor system for performing multi-phase reactions is disclosed. The reactor system includes a reaction vessel having a slinger device (100) mounted on a centrally positioned agitator shaft (102) proximal to an operative top of the reaction vessel. The slinger device (100) comprises a holding means defined by a vertical circumferential plate (108) and a cover plate (107) for at least partially encasing the agitator shaft (102) to define a space for collecting a liquid. The holding means comprise at least one spraying means including spray pipes (106) for distributing the liquid on an inner wall of the reaction vessel by a projectile trajectory path on rotation of the agitator shaft. A concave blade (104) may be positioned over the cover plate (107) for preventing overflow of the liquid from the holding means and forming an umbrella of the flowing liquid to effect scrubbing of the vapors and off-gas.Type: GrantFiled: April 1, 2013Date of Patent: August 16, 2016Assignee: Reliance Industries LimitedInventors: Rajaram S. Ghadge, Thomas Mathew
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Patent number: 9144750Abstract: A method of replacing a first dispersion medium, in a starting slurry composed of the first dispersion medium and either terephthalic acid crystals or isophthalic acid crystals, with a second dispersion medium, and apparatus therefore. The starting slurry is tangentially fed to a vertically extending cylindrical portion of a cyclone-shaped nozzle disposed at an upper portion of a replacement tank of a dispersion medium replacement apparatus, from a tangential direction of the cylindrical portion, and moves circularly along an inner wall of the cylindrical portion. The slurry circularly moving is then discharged from an opening which is disposed at a vertically lower end of the cylindrical portion and dispersed in a second dispersion medium which is fed from a lower portion of the replacement tank.Type: GrantFiled: August 16, 2012Date of Patent: September 29, 2015Assignee: MITSUBISHI GAS CHEMICAL COMPANY, LTD.Inventors: Masato Inari, Fumiya Zaima
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Publication number: 20150094487Abstract: A process and a mixture for oxidizing an alkyl-aromatic compound comprises forming a mixture comprising the alkyl-aromatic compound, a solvent, a bromine source, a catalyst, and ammonium acetate; and contacting the mixture with an oxidizing agent at oxidizing conditions to produce an oxidation product comprising at least one of an aromatic aldehyde, an aromatic alcohol, an aromatic ketone, and an aromatic carboxylic acid. The solvent comprises a carboxylic acid having from 1 to 7 carbon atoms; and the catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium.Type: ApplicationFiled: December 9, 2014Publication date: April 2, 2015Inventors: Alakananda Bhattacharyya, Joel T. Walenga
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Patent number: 8697905Abstract: Methods of producing terephthalic acid are described. The methods involve using a p-xylene stream enriched with p-toluic acid. The p-xylene stream enriched with p-toluic acid, a solvent comprising an ionic liquid and optionally a carboxylic acid, a bromine source, a catalyst, and an oxidizing agent are contacted to produce a product comprising terephthalic acid.Type: GrantFiled: December 29, 2011Date of Patent: April 15, 2014Assignee: UOP LLCInventors: Alakananda Bhattacharyya, Joel T. Walenga
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Patent number: 8685334Abstract: 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: February 11, 2011Date of Patent: April 1, 2014Assignee: Grupo Petrotemex, S.A. de C.V.Inventors: Alan George Wonders, Puneet Gupta, Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede
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Patent number: 8658820Abstract: Various embodiments of the invention herein described generally relate to novel processes for the production of aromatic acids by fixed bed catalytic oxidation of aromatic compounds carrying at least one oxidizable substituent group attached directly to the carbon atom of the corresponding aromatic nucleus. In an embodiment, a novel oxidation process of the present invention comprises the steps of: a) catalytically oxidizing, with an oxidation catalyst, a liquid phase aromatic acid precursor in the presence of a gaseous oxygen source; b) separating a finished product; c) purging the solvent and the oxidation catalyst; d) optionally recycling at least a portion of the solvent into the oxidation reactor; e) recovering at least a portion of the oxidation catalyst; f) recharging the at least a portion of the oxidation catalyst over a solid recharging catalyst bed; and (g) feeding a reactivated oxidation catalyst to the oxidation reactor.Type: GrantFiled: May 26, 2009Date of Patent: February 25, 2014Assignee: GTC Technology US, LLCInventors: George A. Ball, Joseph C. Gentry, Joseph P. Weller, Zhongyi Ding, John R. H. Wilson, Meritxell Guino, Weihua Jin
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Patent number: 8466312Abstract: The process relates improving terephthalic acid purge filtration rate by controlling % water in filter feed slurry and to the recovery of a metal catalyst from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic acid, while utilizing pressure filtration.Type: GrantFiled: August 20, 2010Date of Patent: June 18, 2013Assignee: Grupo Petrotemex, S.A. De C.V.Inventors: Kenny Randolph Parker, Larry Wayne Blair
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Publication number: 20120220800Abstract: A process and apparatus for manufacture of aromatic carboxylic acids comprises a liquid phase oxidation of aromatic hydrocarbon feed materials and treatment of a high pressure off-gas from the liquid phase oxidation to separate water and reaction solvent and purification of impure aromatic carboxylic acid products wherein a purification liquid includes water from off-gas treatment.Type: ApplicationFiled: May 7, 2012Publication date: August 30, 2012Applicant: BP Corporation North America Inc.Inventor: Thomas M. Bartos
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Patent number: 8242304Abstract: A method for producing isophthalic acid, comprising: subjecting a m-phenylene compound and a molecular-oxygen-containing gas to liquid-phase oxidation reaction in the presence of a catalyst comprising a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby precipitate isophthalic acid; removing the isophthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor by following steps (1) to (4) as described.Type: GrantFiled: March 15, 2011Date of Patent: August 14, 2012Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.Inventors: Fumiya Zaima, Nobuo Namiki, Hideaki Fujita, Masato Inari
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Patent number: 8236982Abstract: A method for producing terephthalic acid comprising: subjecting a p-phenylene compound to a liquid-phase oxidation reaction by the use of a molecular-oxygen-containing gas in the presence of a catalyst at least containing a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby cause terephthalic acid to precipitate; removing the terephthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor through a series of operations (1) to (4), as described, for reusing at least a portion of the catalyst in the liquid-phase oxidation reaction.Type: GrantFiled: March 15, 2011Date of Patent: August 7, 2012Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.Inventors: Fumiya Zaima, Masato Inari, Hideaki Fujita, Nobuo Namiki
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Publication number: 20120046493Abstract: The process relates improving terephthalic acid purge filtration rate by controlling % water in filter feed slurry and to the recovery of a metal catalyst from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic acid, while utilizing pressure filtration.Type: ApplicationFiled: August 20, 2010Publication date: February 23, 2012Applicant: EASTMAN CHEMICAL COMPANYInventors: Kenny Randolph Parker, Larry Wayne Blair
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Patent number: 8084639Abstract: A method of reducing or eliminating inflow of water to a dehydration tower using steam for separating water from a carboxylic acid from a reactor outlet gas produced in a reactor during oxidation of an aromatic compound in a carboxylic acid solvent to produce an aromatic acid, for example, oxidation of p-xylene in acetic acid solvent to produce terepthalic acid. The aromatic compound is introduced at the top of an absorption tower and collects ascending carboxylic acid solvent, introduced in the reactor outlet gas at the bottom of the absorption tower, for reintroduction into the reactor eliminating the need to remove and recover the solvent. The absorption tower, condensers and an organic-water separator remove the water in the reactor outlet gas as waste water, and the amount of water inflow to the dehydration tower is reduced or eliminated, as is the amount of steam required for separation.Type: GrantFiled: February 15, 2007Date of Patent: December 27, 2011Assignees: Amtpacific Co., Ltd.Inventor: Ki Joon Kang
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Patent number: 8058369Abstract: The present invention relates to a bubble column reactor comprising a column reactor having a sparger plate dividing the column reactor into a top reaction compartment and a bottom compartment, characterized in that an inlet and outlet line for introducing and disposing a flushing medium are connected to the bottom compartment; and an operation method thereof.Type: GrantFiled: September 6, 2006Date of Patent: November 15, 2011Assignees: Saudi Basic Industries Corporation, Linde AGInventors: Richard Schneider, Peter M. Fritz, Sebastian Muschelknautz, Heinz Bölt, Talal Ali, Fuad Mosa
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Publication number: 20110144384Abstract: A liquid-gas phase reactor system including a slinger located in an upper section (headspace region) of a reaction vessel. The slinger comprises an upper horizontal surface including a plurality of vertically raised vanes extending radially outward along a curved path which effectively distribute liquid about the reactor vessel. A method for conducting an oxidation reaction using a liquid-gas phase reactor system is also disclosed. The disclosed reactor system and method have a broad range of applications but are particularly suited for the production of terephthalic acid.Type: ApplicationFiled: September 20, 2007Publication date: June 16, 2011Inventors: Luciano Piras, Marzio Monagheddu, Andrea Gnagnetti, Kishore K. Kar
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Patent number: 7959879Abstract: Disclosed is an optimized process and apparatus for more efficiently producing aromatic dicarboxylic acids (e.g., terephthalic acid). In one embodiment the process/apparatus reduces costs by recovering and purifying residual terephthalic acid present in the liquid phase of an initial oxidation slurry. In another embodiment the process apparatus reduces costs associated with hydrogenation by forming a final composite product containing unhydrogenated acid particles.Type: GrantFiled: March 18, 2008Date of Patent: June 14, 2011Assignee: Grupo Petrotemex, S.A. de C.V.Inventors: Robert Lin, Marcel de Vreede
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Patent number: 7956215Abstract: Disclosed is a process and apparatus for treating a purge stream in a carboxylic acid production process. The process employs a purge process that allows for the separation of oxidation byproducts into benzoic acid and non-benzoic acid oxidation byproducts, thus providing flexibility in the treatment and use of such oxidation byproducts.Type: GrantFiled: August 16, 2007Date of Patent: June 7, 2011Assignee: Grupo Petrotemex, S.A. de C.V.Inventors: Philip Edward Gibson, Kenny Randolph Parker
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Publication number: 20110108763Abstract: Various embodiments of the invention herein described generally relate to novel processes for the production of aromatic acids by fixed bed catalytic oxidation of aromatic compounds carrying at least one oxidizable substituent group attached directly to the carbon atom of the corresponding aromatic nucleus. In an embodiment, a novel oxidation process of the present invention comprises the steps of: a) catalytically oxidizing, with an oxidation catalyst, a liquid phase aromatic acid precursor in the presence of a gaseous oxygen source; b) separating a finished product; c) purging the solvent and the oxidation catalyst; d) optionally recycling at least a portion of the solvent into the oxidation reactor; e) recovering at least a portion of the oxidation catalyst; f) recharging the at least a portion of the oxidation catalyst over a solid recharging catalyst bed; and (g) feeding a reactivated oxidation catalyst to the oxidation reactor.Type: ApplicationFiled: May 26, 2009Publication date: May 12, 2011Inventors: George A. Ball, Joseph C. Gentry, Joseph P. Weller, Zhongyi Ding, John R.H. Wilson, Meritxell Guino, Weihua Jin
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Patent number: 7919652Abstract: 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: April 5, 2011Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker, Ruairi Seosamh O'Meadhra
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Patent number: 7901636Abstract: 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: February 25, 2009Date of Patent: March 8, 2011Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Robert Lin, Marcel de Vreede, Lee Reynolds Partin
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Patent number: 7902395Abstract: Disclosed is a process and apparatus for treating a purge stream in a carboxylic acid production process. The process employs a purge process that allows for the separation of oxidation byproducts into benzoic acid and non-benzoic acid oxidation byproducts, thus providing flexibility in the treatment and use of such oxidation byproducts.Type: GrantFiled: August 16, 2007Date of Patent: March 8, 2011Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker
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Patent number: 7897809Abstract: 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: August 27, 2007Date of Patent: March 1, 2011Assignee: Eastman Chemical CompanyInventors: Johannes Wilhelmus Sluijmers, Kenny Randolph Parker, Philip Edward Gibson, Marcel de Vreede, Ardie Heijblom
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Patent number: 7897808Abstract: Disclosed is a process and apparatus for treating a purge stream in a carboxylic acid production process. The process employs a purge process that allows for the separation of oxidation byproducts into benzoic acid and non-benzoic acid oxidation byproducts, thus providing flexibility in the treatment and use of such oxidation byproducts.Type: GrantFiled: January 19, 2007Date of Patent: March 1, 2011Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker
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Patent number: 7888529Abstract: 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: February 12, 2007Date of Patent: February 15, 2011Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Philip Edward Gibson
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Patent number: 7884231Abstract: 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: February 8, 2011Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Philip Edward Gibson, Ruairi Seosamh O'Meadhra
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Patent number: 7880031Abstract: 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: February 1, 2011Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker
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Patent number: 7880032Abstract: Disclosed is a process and apparatus for treating a purge stream in a carboxylic acid production process. The process employs a purge process that allows for the separation of oxidation byproducts into benzoic acid and non-benzoic acid oxidation byproducts, thus providing flexibility in the treatment and use of such oxidation byproducts.Type: GrantFiled: January 19, 2007Date of Patent: February 1, 2011Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Philip Edward Gibson
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Patent number: 7863481Abstract: Disclosed is a process and apparatus for treating a purge stream in a carboxylic acid production process. The process employs a purge process that allows for the separation of oxidation byproducts into benzoic acid and non-benzoic acid oxidation byproducts, thus providing flexibility in the treatment and use of such oxidation byproducts.Type: GrantFiled: August 16, 2007Date of Patent: January 4, 2011Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker
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Patent number: 7855305Abstract: 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: October 2, 2008Date of Patent: December 21, 2010Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Philip Edward Gibson, Ruairi Seosamh O'Meadhra
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Patent number: 7829037Abstract: 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: November 9, 2010Assignee: Eastman Chemical CompanyInventors: Thomas Earl Woodruff, Alan George Wonders
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Patent number: 7692039Abstract: The present invention relates to a process for preparing purified terephthalic acid [PTA,], comprising the steps: dissolving crude terephthalic acid [CTA] in an aqueous medium in a reactor; hydrogenating CTA at a temperature of about 260-320° C. and a pressure of about 1100-1300 psig using a hydrogenation catalyst; crystallizing terephthalic acid in the reactor by lowering the temperature of the solution to about 160° C. without evaporation cooling; transferring the content of the reactor to a filtration unit; filtrating the content at a temperature of about 140-160° C. and a pressure of about 40-100 psig, preferably 80-100 psig to obtain a filter cake, washing the filter cake obtained with water having a temperature of about 140-160° C. in the filtration unit; and drying the filter cake.Type: GrantFiled: December 9, 2005Date of Patent: April 6, 2010Assignee: Saudi Basic Industries CorporationInventors: Syed Mohammed Azhar Hashmi, Sulaiman Al-Luhaidan
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Publication number: 20100016629Abstract: The invention provides a method for producing terephthalic acid, characterized by including subjecting a p-phenylene compound to liquid-phase oxidation reaction by use of a molecular-oxygen-containing gas in the presence of a catalyst at least containing a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby cause terephthalic acid to precipitate; removing the terephthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor through a series of the following steps (1) to (4) for reusing at least a portion of the catalyst in the liquid-phase oxidation reaction: (1) an adsorption step including regulating the ratio “amount by mole of bromide ions in the mother liquor/total amount by mole of heavy metal ions in the mother liquor” to 0.Type: ApplicationFiled: December 7, 2007Publication date: January 21, 2010Applicants: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.Inventors: Fumiya Zaima, Masato Inari, Hideaki Fujita, Nobuo Namiki
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Patent number: 7649109Abstract: A polyester production process employing an esterification system that uses a distillation column to recover alcohol produced from an esterification zone and then recirculates the recovered alcohol back to the esterification zone without substantially cooling the recovered alcohol.Type: GrantFiled: December 7, 2006Date of Patent: January 19, 2010Assignee: Eastman Chemical CompanyInventor: Bruce Roger DeBruin
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Publication number: 20090326264Abstract: The present invention relates to a method of reducing water from the reactor outlet gas in the oxidation process of an aromatic compound, for example, in the preparation of terephthalic acid by oxidation of xylene in an acetic acid solvent. As water is removed from the reactor outlet gas at the first absorption tower, the amount of water inflow to the dehydration tower is reduced and, thus, the amount of steam required to separate water and acetic acid at the dehydration tower is reduced and the load of the dehydration tower can be decreased. Further, by carefully controlling the flow amount of the reactor outlet gas to the first absorption tower, the operation of the dehydration tower may be made unnecessary.Type: ApplicationFiled: February 15, 2007Publication date: December 31, 2009Applicants: Ki Joon Kang, AMTPACIFIC CO., LTDInventor: Ki Joon Kang
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Patent number: 7608732Abstract: 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: October 27, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Gino Georges Lavoie, Charles Edwan Sumner, Jr., Bryan Wayne Davenport, Marcel de Vreede, Brent Alan Tennant
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Patent number: 7598415Abstract: The present invention provides a process for the preparation of p-toluic acid by liquid phase oxidation of p-xylene using oxygen or air as oxidant in the presence of p-toluic acid, water as solvent and cobalt salt or its combinations with salts of Ce, Mn as catalyst. Oxidation is carried out at 130-190° C. and pressure sufficient to keep water in liquid state. Oxidation step is followed by filteration to obtain p-toluic acid as major product. Untreated p-xylene is recovered and recycled and the catalyst is recovered from aqueous phase and is recycled.Type: GrantFiled: March 17, 2006Date of Patent: October 6, 2009Assignee: Council of Scientific & Industrial ResearchInventors: Mahendra Pratap Saxena, Ashok Kumar Gupta, Satish Kumar Sharma, Dinesh Prasad Bangwal, Krishan Kumar
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Publication number: 20090234156Abstract: A process and apparatus for manufacture of aromatic carboxylic acids comprises a liquid phase oxidation of aromatic hydrocarbon feed materials and treatment of a high pressure off-gas from the liquid phase oxidation to separate water and reaction solvent and purification of impure aromatic carboxylic acid products wherein a purification liquid includes water from off- gas treatment.Type: ApplicationFiled: March 20, 2006Publication date: September 17, 2009Applicant: BP Corporation North America Inc.Inventor: Thomas M. Bartos
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Patent number: 7582793Abstract: 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: September 1, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Gino Georges Lavoie, Charles Edwan Sumner, Jr.
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Patent number: 7569722Abstract: A process is disclosed that relates to the removal of impurities, specifically benzoic acid, from a mother liquor produced in the synthesis of carboxylic acid, typically terephthalic acid.Type: GrantFiled: August 11, 2005Date of Patent: August 4, 2009Assignee: Eastman Chemical CompanyInventors: Robert Lin, Philip Edward Gibson, Kenny Randolph Parker
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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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Publication number: 20090156858Abstract: The present invention provides an industrially advantageous process for producing 5-phenylisophthalic acid, which process attains excellent selectivity and yield and also realizes recovery and reuse of a catalyst. The process for producing 5-phenylisophthalic acid represented by formula (1) is characterized in that the process includes the following steps (A) to (C): (A) reacting m-xylene with cyclohexene in the presence of hydrogen fluoride and boron trifluoride, to thereby produce 1-cyclohexyl-3,5-dimethylbenzene; (B) dehydrogenating the 1-cyclohexyl-3,5-dimethylbenzene produced in step (A) in the presence of a dehydrogenation catalyst, to thereby produce 3,5-dimethylbiphenyl; and (C) dissolving the 3,5-dimethylbiphenyl produced in step (B) in a solvent and oxidizing the 3,5-dimethylbiphenyl in the co-presence of an oxidation catalyst, to thereby produce 5-phenylisophthalic acid.Type: ApplicationFiled: April 4, 2007Publication date: June 18, 2009Inventor: Junya Nishiuchi
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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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Patent number: 7501537Abstract: Disclosed is an optimized system for more efficiently and economically producing terephthalic acid. The system minimizes or eliminates the need for liquor exchange upstream of oxidative digestion and/or upstream of substantial cooling of the TPA-containing slurry.Type: GrantFiled: March 1, 2006Date of Patent: March 10, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Ronald Buford Sheppard, Martin De Boer, Raymond Elbert Fogle, Marcel de Vreede
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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