With Recycle Or Recovery Of Reaction Component Patents (Class 562/414)
  • Patent number: 10843995
    Abstract: 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: Grant
    Filed: June 19, 2018
    Date of Patent: November 24, 2020
    Assignee: BP Corporation North America Inc.
    Inventor: Anders Bitsch-Larsen
  • Patent number: 10435799
    Abstract: 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: Grant
    Filed: May 20, 2016
    Date of Patent: October 8, 2019
    Assignee: Avantium Knowledge Centre B.V.
    Inventors: Klaas Jan Pieter Schouten, Jan Cornelis Van Der Waal, Maria Varini, Gerardus Johannes Maria Gruter
  • Patent number: 10273198
    Abstract: 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: Grant
    Filed: January 9, 2015
    Date of Patent: April 30, 2019
    Assignee: TIANHUA INSTITUTE OF CHEMICAL MACHINERY AND AUTOMATION CO., LTD
    Inventors: Xu Zhao, Wanyao Zhang, Zhongxin Sun, Yongpeng Tan, Xiangnan Zhai, Tianbao Wang, Yuanyue Liang, Guohai Zhang, Xiaopeng Feng, Yanshun Shen
  • Patent number: 10156801
    Abstract: 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: Grant
    Filed: August 13, 2014
    Date of Patent: December 18, 2018
    Assignee: Ricoh Company, Ltd.
    Inventors: Kohsuke Nagata, Shinya Nakayama, Tsuyoshi Sugimoto, Daisuke Asahina, Susumu Chiba
  • Patent number: 9550712
    Abstract: 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: Grant
    Filed: August 16, 2012
    Date of Patent: January 24, 2017
    Assignee: 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
  • Patent number: 9422219
    Abstract: 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: Grant
    Filed: December 30, 2014
    Date of Patent: August 23, 2016
    Assignee: BP Corporation North America Inc.
    Inventor: Thomas M. Bartos
  • Patent number: 9415371
    Abstract: 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: Grant
    Filed: April 1, 2013
    Date of Patent: August 16, 2016
    Assignee: Reliance Industries Limited
    Inventors: Rajaram S. Ghadge, Thomas Mathew
  • Patent number: 9144750
    Abstract: 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: Grant
    Filed: August 16, 2012
    Date of Patent: September 29, 2015
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, LTD.
    Inventors: Masato Inari, Fumiya Zaima
  • Publication number: 20150094487
    Abstract: 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: Application
    Filed: December 9, 2014
    Publication date: April 2, 2015
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Patent number: 8697905
    Abstract: 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: Grant
    Filed: December 29, 2011
    Date of Patent: April 15, 2014
    Assignee: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Patent number: 8685334
    Abstract: 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: Grant
    Filed: February 11, 2011
    Date of Patent: April 1, 2014
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Alan George Wonders, Puneet Gupta, Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede
  • Patent number: 8658820
    Abstract: 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: Grant
    Filed: May 26, 2009
    Date of Patent: February 25, 2014
    Assignee: GTC Technology US, LLC
    Inventors: George A. Ball, Joseph C. Gentry, Joseph P. Weller, Zhongyi Ding, John R. H. Wilson, Meritxell Guino, Weihua Jin
  • Patent number: 8466312
    Abstract: 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: Grant
    Filed: August 20, 2010
    Date of Patent: June 18, 2013
    Assignee: Grupo Petrotemex, S.A. De C.V.
    Inventors: Kenny Randolph Parker, Larry Wayne Blair
  • Publication number: 20120220800
    Abstract: 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: Application
    Filed: May 7, 2012
    Publication date: August 30, 2012
    Applicant: BP Corporation North America Inc.
    Inventor: Thomas M. Bartos
  • Patent number: 8242304
    Abstract: 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: Grant
    Filed: March 15, 2011
    Date of Patent: August 14, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Nobuo Namiki, Hideaki Fujita, Masato Inari
  • Patent number: 8236982
    Abstract: 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: Grant
    Filed: March 15, 2011
    Date of Patent: August 7, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Masato Inari, Hideaki Fujita, Nobuo Namiki
  • Publication number: 20120046493
    Abstract: 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: Application
    Filed: August 20, 2010
    Publication date: February 23, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Kenny Randolph Parker, Larry Wayne Blair
  • Patent number: 8084639
    Abstract: 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: Grant
    Filed: February 15, 2007
    Date of Patent: December 27, 2011
    Assignees: Amtpacific Co., Ltd.
    Inventor: Ki Joon Kang
  • Patent number: 8058369
    Abstract: 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: Grant
    Filed: September 6, 2006
    Date of Patent: November 15, 2011
    Assignees: Saudi Basic Industries Corporation, Linde AG
    Inventors: Richard Schneider, Peter M. Fritz, Sebastian Muschelknautz, Heinz Bölt, Talal Ali, Fuad Mosa
  • Publication number: 20110144384
    Abstract: 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: Application
    Filed: September 20, 2007
    Publication date: June 16, 2011
    Inventors: Luciano Piras, Marzio Monagheddu, Andrea Gnagnetti, Kishore K. Kar
  • Patent number: 7959879
    Abstract: 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: Grant
    Filed: March 18, 2008
    Date of Patent: June 14, 2011
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Robert Lin, Marcel de Vreede
  • Patent number: 7956215
    Abstract: 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: Grant
    Filed: August 16, 2007
    Date of Patent: June 7, 2011
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Philip Edward Gibson, Kenny Randolph Parker
  • Publication number: 20110108763
    Abstract: 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: Application
    Filed: May 26, 2009
    Publication date: May 12, 2011
    Inventors: George A. Ball, Joseph C. Gentry, Joseph P. Weller, Zhongyi Ding, John R.H. Wilson, Meritxell Guino, Weihua Jin
  • Patent number: 7919652
    Abstract: 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: Grant
    Filed: March 1, 2006
    Date of Patent: April 5, 2011
    Assignee: Eastman Chemical Company
    Inventors: Philip Edward Gibson, Kenny Randolph Parker, Ruairi Seosamh O'Meadhra
  • Patent number: 7902395
    Abstract: 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: Grant
    Filed: August 16, 2007
    Date of Patent: March 8, 2011
    Assignee: Eastman Chemical Company
    Inventors: Philip Edward Gibson, Kenny Randolph Parker
  • Patent number: 7901636
    Abstract: 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: Grant
    Filed: February 25, 2009
    Date of Patent: March 8, 2011
    Assignee: Eastman Chemical Company
    Inventors: Alan George Wonders, Robert Lin, Marcel de Vreede, Lee Reynolds Partin
  • Patent number: 7897808
    Abstract: 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: Grant
    Filed: January 19, 2007
    Date of Patent: March 1, 2011
    Assignee: Eastman Chemical Company
    Inventors: Philip Edward Gibson, Kenny Randolph Parker
  • Patent number: 7897809
    Abstract: 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: Grant
    Filed: August 27, 2007
    Date of Patent: March 1, 2011
    Assignee: Eastman Chemical Company
    Inventors: Johannes Wilhelmus Sluijmers, Kenny Randolph Parker, Philip Edward Gibson, Marcel de Vreede, Ardie Heijblom
  • Patent number: 7888529
    Abstract: 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: Grant
    Filed: February 12, 2007
    Date of Patent: February 15, 2011
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Philip Edward Gibson
  • Patent number: 7884231
    Abstract: 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: Grant
    Filed: March 1, 2006
    Date of Patent: February 8, 2011
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Philip Edward Gibson, Ruairi Seosamh O'Meadhra
  • Patent number: 7880032
    Abstract: 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: Grant
    Filed: January 19, 2007
    Date of Patent: February 1, 2011
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Philip Edward Gibson
  • Patent number: 7880031
    Abstract: 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: Grant
    Filed: March 1, 2006
    Date of Patent: February 1, 2011
    Assignee: Eastman Chemical Company
    Inventors: Philip Edward Gibson, Kenny Randolph Parker
  • Patent number: 7863481
    Abstract: 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: Grant
    Filed: August 16, 2007
    Date of Patent: January 4, 2011
    Assignee: Eastman Chemical Company
    Inventors: Philip Edward Gibson, Kenny Randolph Parker
  • Patent number: 7855305
    Abstract: 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: Grant
    Filed: October 2, 2008
    Date of Patent: December 21, 2010
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Philip Edward Gibson, Ruairi Seosamh O'Meadhra
  • Patent number: 7829037
    Abstract: 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: Grant
    Filed: August 29, 2007
    Date of Patent: November 9, 2010
    Assignee: Eastman Chemical Company
    Inventors: Thomas Earl Woodruff, Alan George Wonders
  • Patent number: 7692039
    Abstract: 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: Grant
    Filed: December 9, 2005
    Date of Patent: April 6, 2010
    Assignee: Saudi Basic Industries Corporation
    Inventors: Syed Mohammed Azhar Hashmi, Sulaiman Al-Luhaidan
  • Publication number: 20100016629
    Abstract: 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: Application
    Filed: December 7, 2007
    Publication date: January 21, 2010
    Applicants: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Masato Inari, Hideaki Fujita, Nobuo Namiki
  • Patent number: 7649109
    Abstract: 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: Grant
    Filed: December 7, 2006
    Date of Patent: January 19, 2010
    Assignee: Eastman Chemical Company
    Inventor: Bruce Roger DeBruin
  • Publication number: 20090326264
    Abstract: 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: Application
    Filed: February 15, 2007
    Publication date: December 31, 2009
    Applicants: Ki Joon Kang, AMTPACIFIC CO., LTD
    Inventor: Ki Joon Kang
  • Patent number: 7608732
    Abstract: 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: Grant
    Filed: June 16, 2005
    Date of Patent: October 27, 2009
    Assignee: Eastman Chemical Company
    Inventors: Alan George Wonders, Gino Georges Lavoie, Charles Edwan Sumner, Jr., Bryan Wayne Davenport, Marcel de Vreede, Brent Alan Tennant
  • Patent number: 7598415
    Abstract: 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: Grant
    Filed: March 17, 2006
    Date of Patent: October 6, 2009
    Assignee: Council of Scientific & Industrial Research
    Inventors: Mahendra Pratap Saxena, Ashok Kumar Gupta, Satish Kumar Sharma, Dinesh Prasad Bangwal, Krishan Kumar
  • Publication number: 20090234156
    Abstract: 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: Application
    Filed: March 20, 2006
    Publication date: September 17, 2009
    Applicant: BP Corporation North America Inc.
    Inventor: Thomas M. Bartos
  • Patent number: 7582793
    Abstract: 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: Grant
    Filed: June 16, 2005
    Date of Patent: September 1, 2009
    Assignee: Eastman Chemical Company
    Inventors: Alan George Wonders, Gino Georges Lavoie, Charles Edwan Sumner, Jr.
  • Patent number: 7569722
    Abstract: 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: Grant
    Filed: August 11, 2005
    Date of Patent: August 4, 2009
    Assignee: Eastman Chemical Company
    Inventors: Robert Lin, Philip Edward Gibson, Kenny Randolph Parker
  • Patent number: 7556784
    Abstract: 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: Grant
    Filed: March 18, 2008
    Date of Patent: July 7, 2009
    Assignee: Eastman Chemical Company
    Inventors: Robert Lin, Marcel de Vreede
  • Publication number: 20090156858
    Abstract: 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: Application
    Filed: April 4, 2007
    Publication date: June 18, 2009
    Inventor: Junya Nishiuchi
  • Patent number: 7504535
    Abstract: 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: Grant
    Filed: June 16, 2005
    Date of Patent: March 17, 2009
    Assignee: Eastman Chemical Company
    Inventors: Marcel de Vreede, Alan George Wonders, Robert Lin
  • Patent number: 7501537
    Abstract: 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: Grant
    Filed: March 1, 2006
    Date of Patent: March 10, 2009
    Assignee: Eastman Chemical Company
    Inventors: Alan George Wonders, Ronald Buford Sheppard, Martin De Boer, Raymond Elbert Fogle, Marcel de Vreede
  • Patent number: 7498002
    Abstract: 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: Grant
    Filed: August 29, 2007
    Date of Patent: March 3, 2009
    Assignee: Eastman Chemical Company
    Inventors: Alan George Wonders, Howard Wood Jenkins, Jr., Lee Reynolds Partin, Wayne Scott Strasser, Marcel deVreede
  • Patent number: 7498003
    Abstract: 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: Grant
    Filed: August 29, 2007
    Date of Patent: March 3, 2009
    Assignee: Eastman Chemical Company
    Inventors: Alan George Wonders, Lee Reynolds Partin, Wayne Scott Strasser, Marcel deVreede, Puneet Gupta