Air, Oxygen, Or Ozone Oxidant Patents (Class 562/412)
  • Patent number: 10322991
    Abstract: A process for selective oxidation of dimethyl-1,1?-biphenyl to form methyl-1,1?-biphenyl mono-carboxylic acid(s), comprising contacting a solution of dimethyl-1,1?-biphenyl in acetic acid solvent in the presence of a Co(II) acetate catalyst and air, and optionally adding a co-solvent, or adding sodium or potassium acetate, and oxidizing the dimethyl-1,1?-biphenyl under time and temperature conditions sufficient to form one or more methyl-1,1?-biphenyl mono-carboxylic acid(s). The mono-carboxylic acids are advantageously isolated and esterified to form biphenyl mono-esters for use as plasticizers.
    Type: Grant
    Filed: December 1, 2017
    Date of Patent: June 18, 2019
    Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
    Inventors: Michael P. Lanci, Joshua W. Allen, Jarid M. Metz, Victor DeFlorio, Jihad M. Dakka, Bryan A. Patel, Michael Salciccioli, Michael W. Weber, Stephen Zushma
  • Patent number: 10287230
    Abstract: A process for selective oxidation of dimethyl-1,1?-biphenyl(s) to form methyl-1,1?-biphenyl mono-carboxylic acid(s), which can be esterified to form plasticizers, comprising contacting a solution of dimethyl-1,1?-biphenyl(s) in acetic acid in the presence of an oxidation catalyst and air under time and temperature conditions sufficient to oxidize the dimethyl-1,1?-biphenyl(s) into one or more methyl-1,1?-biphenyl mono-carboxylic acid(s) products, conducting at least one of (i) adding an antisolvent, or (ii) optimizing a total conversion of dimethyl-1,1?-biphenyl(s) by oxidation based upon a molar ratio of dimethyl-1,1?-biphenyl isomers, or (iii) precipitating the methyl-1,1?-biphenyl mono-carboxylic acid(s) products by lowering the temperature, or (iv) decreasing the oxidation reaction temperature to enhance conversion of aldehydes over methyl functional groups, so as to limit over-oxidation of the dimethyl-1,1?-biphenyl(s), wherein the oxidation reaction is conducted in the absence of bromide-containing cata
    Type: Grant
    Filed: December 1, 2017
    Date of Patent: May 14, 2019
    Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
    Inventors: Michael P. Lanci, Joshua W. Allen, Jarid M. Metz, Victor DeFlorio, Jihad M. Dakka, Bryan A. Patel, Michael Salciccioli, Michael W. Weber, Stephen Zushma
  • Patent number: 9447013
    Abstract: Provided is a method of oxidizing a substrate with excellent oxidizing power to yield a corresponding oxide. The method can employ a commercially available imide compound as intact as a catalyst and can produce the oxide in a high yield under mild conditions. A method for producing an oxide according to the present invention includes performing oxidation of a substrate in the presence of oxygen and ozone under catalysis of an imide compound to yield a corresponding oxide. The imide compound has a cyclic imide skeleton represented by Formula (I). In the formula, n is selected from 0 and 1; and X is selected from an oxygen atom and an —OR group, where R is selected from hydrogen and a hydroxy-protecting group.
    Type: Grant
    Filed: July 14, 2014
    Date of Patent: September 20, 2016
    Assignee: DAICEL CORPORATION
    Inventors: Yasutaka Ishii, Ichiro Takase, Yoshiya Narasaki, Takamasa Suzuki
  • Patent number: 9394223
    Abstract: A process including: (a) contacting an aqueous solution including a crude aromatic carboxylic acid with an oxygen source in the presence of an oxidation catalyst including at least one of Ru, Au, Pt, Ir or V, and oxides, alloys, salts and mixtures thereof; and (b) purifying the product of step (a) to form a purified aromatic carboxylic acid.
    Type: Grant
    Filed: December 30, 2014
    Date of Patent: July 19, 2016
    Assignee: BP Corporation North America Inc.
    Inventor: Peter Metelski
  • Patent number: 9388111
    Abstract: Disclosed is a method for purifying aromatic dicarboxylic acid such as isophthalic acid or terephthalic acid. The process treats a crude carboxylic acid (CCA) composition by feeding a CCA composition comprising a liquid and a solid to a filter cake formation zone to form a CCA wet cake composition and a first mother liquor stream; dewatering said CCA wet cake composition to form a dewatered CCA wet cake composition having a second liquid level that is lower than the first liquid level or having no liquid level and a second mother liquor stream; and washing the dewatered CCA wet cake composition with a wash stream in a wash zone to forma washed CCA wet cake composition and a wash liquor stream.
    Type: Grant
    Filed: December 27, 2013
    Date of Patent: July 12, 2016
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Jennifer Caroline Moffitt, Kevin John Fontenot
  • Patent number: 9328051
    Abstract: Disclosed is a method for purifying aromatic dicarboxylic acid such as isophthalic acid or terephthalic acid.
    Type: Grant
    Filed: December 27, 2013
    Date of Patent: May 3, 2016
    Assignee: Eastman Chemical Company
    Inventors: Kenny Randolph Parker, Jennifer Caroline Moffitt
  • Patent number: 9315441
    Abstract: Processes for manufacturing purified aromatic carboxylic acids include: generating high-pressure steam from boiler feed water supplied to a boiler; heating a crude aromatic carboxylic acid using the high-pressure steam, whereby the high pressure steam is condensed to form a high-pressure condensate; and purifying the crude aromatic carboxylic acid to form a purified aromatic carboxylic acid. The boiler feed water includes at least a portion of the high-pressure condensate and makeup boiler feed water from at least one additional source.
    Type: Grant
    Filed: December 30, 2014
    Date of Patent: April 19, 2016
    Assignee: BP Corporation North America Inc.
    Inventors: Fred T. Clark, Thomas M. Bartos, Allen Nelson
  • Patent number: 9266809
    Abstract: A solid terephthalic acid composition and a process for producing terephthalic acid from para-xylene. The process comprises forming a mixture comprising the para-xylene, a solvent, a bromine source, and a catalyst; and oxidizing the para-xylene by contacting the mixture with an oxidizing agent at oxidizing conditions to produce a solid oxidation product comprising terephthalic acid, para-toluic acid, 4-carboxybenzaldehyde. The solvent comprises a carboxylic acid having from 1 to 7 carbon atoms and an dialkyl imidazolium ionic liquid; and the catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium. The solid terephthalic acid composition comprises, less than about 4,000 ppm-wt 4-carboxybenzaldehyde content, and more than about 2,000 ppm-wt a para-toluic acid.
    Type: Grant
    Filed: November 7, 2014
    Date of Patent: February 23, 2016
    Assignees: UOP LLC, BORESKOV INSTITUTE OF CATALYSIS
    Inventors: Alakananda Bhattacharyya, Joseph A. Kocal, Joel T. Walenga, Nikolay Y. Adonin, Nina I. Kuznetsova, Bair S. Bal'zhinimaev
  • Patent number: 9260359
    Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose) and ethylene in the presence of an acid, such as a Lewis acid. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF) and 2-methylfuran, which may be converted into para-xylene and toluene, respectively. In particular, para-xylene can then be oxidized to form terephthalic acid.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: February 16, 2016
    Assignee: Micromidas, Inc.
    Inventors: Makoto N. Masuno, Douglas Cannon, John Bissell, Ryan L. Smith, Alex Benjamin Wood, Patrick B. Smith, Dennis A. Hucul, Katherine Brune
  • Patent number: 9260370
    Abstract: Processes for manufacturing purified aromatic carboxylic acids include: oxidizing a substituted aromatic compound in a reaction zone to form a crude aromatic carboxylic add; transferring a vapor phase from the reaction zone to a separation zone, the vapor phase containing water and a plurality of organic compounds including at least one oxidation by-product; withdrawing an organic-depleted water stream from the separation zone and combining at least a portion of the organic-depleted water stream with at least a portion of the crude aromatic carboxylic acid in a purification zone; and purifying the crude aromatic carboxylic acid in the purification zone.
    Type: Grant
    Filed: December 30, 2014
    Date of Patent: February 16, 2016
    Assignee: BP Corporation North America Inc.
    Inventor: Thomas M. Bartos
  • Patent number: 9199904
    Abstract: The present invention relates to a process of making a compound of formula (XII) or (XIIA): wherein R1,R2, R4 and X are as defined herein.
    Type: Grant
    Filed: March 15, 2012
    Date of Patent: December 1, 2015
    Assignee: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
    Inventors: Jean-Nicolas Desrosiers, Joe Ju Gao, Jason Alan Mulder, Jinhua J. Song, Xingzhong Zeng
  • Patent number: 9150484
    Abstract: Methods of producing terephthalic acid are described. The methods involve using a p-xylene stream enriched with p-toluic acid and optionally terephthalic acid at impurity levels. 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 12, 2013
    Date of Patent: October 6, 2015
    Assignee: UOP LLC
    Inventor: Alakananda Bhattacharyya
  • Patent number: 9062690
    Abstract: A gas compression system for use with a gas stream. The gas compression system may include a number of compressors for compressing the gas stream, one or more ejectors for further compressing the gas stream, a condenser positioned downstream of the ejectors, and a waste heat source. A return portion of the gas stream may be in communication with the ejectors via the waste heat source.
    Type: Grant
    Filed: November 30, 2010
    Date of Patent: June 23, 2015
    Assignee: General Electric Company
    Inventors: Miguel Angel Gonzalez, Matthias Finkenrath, Vittorio Michelassi
  • Patent number: 9035090
    Abstract: In a process for removing aromatic carboxylic acid from a slurry thereof in solvent, the slurry is split into sub streams and each of said sub streams is supplied to a respective rotary pressure filter such that the sub stream pass through the filters in parallel. Gas is passed through the rotary pressure filters in series in an open-loop arrangement.
    Type: Grant
    Filed: January 12, 2012
    Date of Patent: May 19, 2015
    Assignee: Davy Process Technology Limited
    Inventor: Andrea Gnagnetti
  • Patent number: 9024059
    Abstract: Methods of producing terephthalic acid are described. The methods involve using a substantially pure p-toluic acid stream. The substantially pure p-toluic acid stream, 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: May 5, 2015
    Assignee: UOP LLC
    Inventor: Alakananda Bhattacharyya
  • Patent number: 8968686
    Abstract: Disclosed are process and apparatus for vertical splitting of the oxygen supply to a post-oxidation reactor. Further disclosed are process and apparatus for supplying reaction medium to a post-oxidation reactor at a mid-level inlet. Such apparatus and process can assist in reducing oxygen pinch throughout the post-oxidation reactor.
    Type: Grant
    Filed: December 1, 2010
    Date of Patent: March 3, 2015
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Ashfaq Shaikh, Alan George Wonders
  • Patent number: 8952195
    Abstract: A process for oxidizing an alkyl-aromatic compound is described. The process includes contacting the alkyl-aromatic compound, a solvent comprising an ionic liquid, a bromine source, a catalyst, and an oxidizing agent in a first reaction zone to produce a first product comprising a first mother liquor and at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid.
    Type: Grant
    Filed: October 12, 2012
    Date of Patent: February 10, 2015
    Assignee: UOP LLC
    Inventors: Alakananda Bhattacharyya, Raymond Shih
  • Patent number: 8946471
    Abstract: Processes for oxidizing an alkyl-aromatic compound are described. The processes include contacting an alkyl-aromatic compound, a solvent, a bromine source, a catalyst, and an oxidizing agent to produce a product comprising at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid. The composition of the solvent is controlled to reduce the impurities in the product.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: February 3, 2015
    Assignee: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Patent number: 8940255
    Abstract: Disclosed are process and apparatus for vertical splitting of the oxygen supply to a post-oxidation reactor. Further disclosed are process and apparatus for supplying reaction medium to a post-oxidation reactor at a mid-level inlet. Such apparatus and process can assist in reducing oxygen pinch throughout the post-oxidation reactor.
    Type: Grant
    Filed: December 1, 2010
    Date of Patent: January 27, 2015
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Ashfaq Shaikh, Alan George Wonders
  • Patent number: 8936767
    Abstract: Disclosed are process and apparatus for vertical splitting of the oxygen supply to a post-oxidation reactor. Further disclosed are process and apparatus for supplying reaction medium to a post-oxidation reactor at a mid-level inlet. Such apparatus and process can assist in reducing oxygen pinch throughout the post-oxidation reactor.
    Type: Grant
    Filed: December 1, 2010
    Date of Patent: January 20, 2015
    Assignee: Grupo Petrotemex. S.A. DE C.V.
    Inventors: Ashfaq Shaikh, Alan George Wonders, David Lange
  • Patent number: 8933266
    Abstract: A process for producing terephthalic acid from para-xylene. The process comprises forming a mixture comprising the para-xylene, a solvent, a bromine source, a catalyst, and ammonium acetate; and oxidizing the para-xylene by contacting the mixture with an oxidizing agent at oxidizing conditions to produce a solid oxidation product comprising terephthalic acid, para-toluic acid, 4-carboxybenzaldehyde. 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: Grant
    Filed: June 8, 2011
    Date of Patent: January 13, 2015
    Assignee: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Patent number: 8927764
    Abstract: Methods of producing terephthalic acid are described. The methods involve using a substantially pure 4-CBA stream. The substantially pure 4-CBA stream, 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: January 6, 2015
    Assignee: UOP LLC
    Inventor: Alakananda Bhattacharyya
  • Publication number: 20140371484
    Abstract: Disclosed is a halide-free catalyst system and method for oxidizing toluene to form benzoic acid in benzoic acid solvent. The catalyst system contains Co, at least one of Zr and Hf, and an alkali metal basic salt.
    Type: Application
    Filed: September 3, 2014
    Publication date: December 18, 2014
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, JR., Stephanie Nicole Rollins-Testerman, Craig Steven Dunn
  • Patent number: 8884054
    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, and a catalyst; 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 an ionic liquid selected from the group consisting of an imidazolium ionic liquid, a pyridinium ionic liquid, a phosphonium ionic liquid, a tetra alkyl ammonium ionic liquid, and combinations thereof. The catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium.
    Type: Grant
    Filed: June 8, 2011
    Date of Patent: November 11, 2014
    Assignees: UOP LLC, Boreskov Institute of Catalysis
    Inventors: Alakananda Bhattacharyya, Joseph A. Kocal, Joel T. Walenga, Nikolay Y. Adonin, Nina I. Kuznetsova, Bair S. Bal'zhinimaev
  • Patent number: 8884055
    Abstract: A solid terephthalic acid composition and a process for producing terephthalic acid from para-xylene. The process comprises forming a mixture comprising the para-xylene, a solvent, a bromine source, and a catalyst; and oxidizing the para-xylene by contacting the mixture with an oxidizing agent at oxidizing conditions to produce a solid oxidation product comprising terephthalic acid, para-toluic acid, 4-carboxybenzaldehyde. The solvent comprises a carboxylic acid having from 1 to 7 carbon atoms and an dialkyl imidazolium ionic liquid; and the catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium. The solid terephthalic acid composition comprises, less than about 4,000 ppm-wt 4-carboxybenzaldehyde content, and more than about 2,000 ppm-wt a para-toluic acid.
    Type: Grant
    Filed: June 8, 2011
    Date of Patent: November 11, 2014
    Assignees: UOP LLC, Boreskov Institute of Catalysis
    Inventors: Alakananda Bhattacharyya, Joseph A. Kocal, Joel T. Walenga, Nikolay Y. Adonin, Nina I. Kuznetsova, Bair S. Bal'zhinimaev
  • Patent number: 8790601
    Abstract: Disclosed are process and apparatus for vertical splitting of the oxygen supply to a post-oxidation reactor. Further disclosed are process and apparatus for supplying reaction medium to a post-oxidation reactor at a mid-level inlet. Such apparatus and process can assist in reducing oxygen pinch throughout the post-oxidation reactor.
    Type: Grant
    Filed: December 1, 2010
    Date of Patent: July 29, 2014
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Ashfaq Shaikh, David Lange
  • Patent number: 8779185
    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: Grant
    Filed: May 7, 2012
    Date of Patent: July 15, 2014
    Assignee: BP Corporation North America Inc.
    Inventor: Thomas M. Bartos
  • Patent number: 8759571
    Abstract: A process for oxidizing an alkyl-aromatic compound is described. The process includes oxidizing the alkyl-aromatic compound to produce a first oxidation product; contacting at least a portion of the first oxidation product, a solvent comprising an ionic liquid, a bromine source, a catalyst, and an oxidizing agent to produce a second oxidation product comprising at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: June 24, 2014
    Assignee: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • 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
  • Publication number: 20140051884
    Abstract: An applicator instrument (1600) for dispensing surgical fasteners includes a housing (1606) and a curved shaft (1616). Surgical fasteners are disposed within the curved shaft for being dispensed from the distal end of the curved shaft. An advancer (1466) is disposed inside the curved shaft for shifting the surgical fasteners one position closer to the distal end of the curved shaft each time the advancer moves distally. A firing element (1474) is disposed inside the curved shaft and is movable between the proximal and distal ends of the curved shaft for dispensing the surgical fasteners from the distal end of the curved shaft. A staging assembly (1521) is adapted to receive a leading one of the surgical fasteners from the advancer as the advancer moves distally to shift the leading surgical fastener into substantial alignment with the firing element when the advancer moves proximally.
    Type: Application
    Filed: November 8, 2011
    Publication date: February 20, 2014
    Applicant: INVISTA North America S.a.r.l.
    Inventors: Alan Macpherson Ure, Ajay Tharakan
  • Patent number: 8624055
    Abstract: Catalytic compositions for conversion of substituted aromatic feed materials to oxidized products comprising aromatic carboxylic acid derivatives of the substituted aromatic feed materials comprise solid particles comprising palladium in combination with at least one of antimony, bismuth and gold, and optionally, an additional metal or metalloid component effective to promote activity or selectivity of the palladium and antimony, bismuth or gold for oxidation to aromatic carboxylic acids. A process for oxidizing substituted aromatic feed materials comprises contacting the feed material with oxygen in the presence of such catalytic compositions in a liquid reaction mixture.
    Type: Grant
    Filed: May 1, 2008
    Date of Patent: January 7, 2014
    Assignee: BP Corporation North America Inc.
    Inventors: Wayne P. Schammel, Bradley J. Huggins, Matthew A. Kulzick, Philip O. Nubel, Bryan M. Rabatic, Chengxiang Zhou, Victor A. Adamian, William H. Gong, Peter D. Metelski, Jeffrey T. Miller
  • Patent number: 8614350
    Abstract: Methods and apparatus for producing a carboxylic acid employing a solvent from esterification of lignocellulosic materials. An acid-containing composition from esterification of lignocellulosic materials can be employed in the oxidation of para-xylene to terephthalic acid. The acid-containing composition can comprise acetic acid, acetic anhydride, and one or more terpenes or terpenes derivatives.
    Type: Grant
    Filed: August 24, 2012
    Date of Patent: December 24, 2013
    Assignee: Eastman Chemical Company
    Inventors: Mesfin Ejerssa Janka, Charles Edwan Sumner, Jr., Adam Scott Howard, Kenny Randolph Parker
  • Patent number: 8575387
    Abstract: The present invention relates to a method for preparing carboxylic acids comprising the step of contacting an aromatic hydrocarbon comprising at least one group including an ? C-atom that is oxidizable to a carboxylic group in liquid phase with an oxygen containing gas in the presence of a heterogeneous catalyst with perovskite structure ABO3 with A being selected from at least one element of groups 1 to 3 of the Periodic Table, lanthanides or actinides, and B being selected from at least one element of the groups 4 to 15 of the periodic table or an oxygen-defective derivative of that catalyst having the formula ABO3?? with 0<?<1.
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: November 5, 2013
    Assignee: King Saud University
    Inventors: Saeed Mohammed Al-Zahrani, Horacio Falcon Richeni, Ainara Aguadero Garin, Jose Antonio Alonso Alonso, Jose Miguel Campos Martin, Jose Luis Garcia Fierro
  • Patent number: 8501986
    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 10, 2010
    Date of Patent: August 6, 2013
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Alan George Wonders, Robert Lin, Lee Reynolds Partin, Marcel de Vreede, Wayne Scott Strasser
  • 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
  • Patent number: 8455680
    Abstract: Methods and apparatus for producing a carboxylic acid employing a solvent from esterification of lignocellulosic materials. An acid-containing composition from esterification of lignocellulosic materials can be employed in the oxidation of para-xylene to terephthalic acid. The acid-containing composition can comprise acetic acid, acetic anhydride, and one or more terpenes.
    Type: Grant
    Filed: January 7, 2009
    Date of Patent: June 4, 2013
    Assignee: Eastman Chemical Company
    Inventors: Wout Fornara, Martin Gout, Charles Edwan Sumner, Jr.
  • Publication number: 20130130345
    Abstract: The invention provides a process for producing a variety renewable aromatic compounds such as benzene, toluene, xylenes, and cumene, as well as compounds derived from these including, for example, aniline, benzoic acid, cresol, cyclohexane, cyclohexanone, phenol and bisphenol A, toluene di-isocyanate, isophthalic acid, phthalic anhydride, terephthalic acid and dimethyl terephthalate. The invention also provides for renewable forms of these aromatic compounds.
    Type: Application
    Filed: June 28, 2011
    Publication date: May 23, 2013
    Applicant: JNF BIOCHEMICALS, LLC
    Inventors: Wendy Thai, David A. Sikkenga, Will Schroeder
  • Publication number: 20130041175
    Abstract: A process for oxidizing an alkyl-aromatic compound is described. The process includes contacting the alkyl-aromatic compound, a solvent comprising an ionic liquid, a bromine source, a catalyst, and an oxidizing agent in a first reaction zone to produce a first product comprising a first mother liquor and at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid.
    Type: Application
    Filed: October 12, 2012
    Publication date: February 14, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Raymond Shih
  • Patent number: 8314267
    Abstract: Catalytic processes for the conversion of 2,5-dimethyl furan (DMF) to para-xylene are described. Para-xylene is a key product that is currently obtained commercially from petroleum sources. However, it has now been determined that the cycloaddition of ethylene to DMF provides an alternative route to para-xylene. Advantageously, the DMF starting material for the processes may be synthesized from carbohydrates (e.g., glucose or fructose), thereby providing a pathway that relies at least partly, if not completely, on renewable feedstocks.
    Type: Grant
    Filed: June 26, 2009
    Date of Patent: November 20, 2012
    Assignee: UOP LLC
    Inventor: Timothy A. Brandvold
  • Patent number: 8188309
    Abstract: 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: Grant
    Filed: December 20, 2005
    Date of Patent: May 29, 2012
    Assignee: Process Design Center B.V.
    Inventors: Johannes Maria Franciscus Sijben, Herman Jozef Claudius De Meyer
  • Patent number: 8178716
    Abstract: The present invention relates to a multi-stage crystallization process which comprises the steps of feeding a solution of terephthalic acid or a slurry (raw slurry) containing terephthalic acid partially precipitated to a first crystallization vessel to precipitate the terephthalic acid therein; and feeding a slurry (crystallization slurry) containing the thus precipitated terephthalic acid sequentially to second and subsequent crystallization vessels, wherein while continuously supplying a cleaning solvent to a delivery conduit connecting the former-stage crystallization vessel and the next latter-stage crystallization vessel to each other, the crystallization slurry is fed through the delivery conduit.
    Type: Grant
    Filed: May 2, 2007
    Date of Patent: May 15, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Nirou Hoshishima
  • Patent number: 8173836
    Abstract: Disclosed is a method and apparatus for drying a wet cake in a carboxylic acid production process. The method comprises employing a contact dryer for drying solid particles of carboxylic acid, where the solid particles can have a residence time of less than about 7 minutes in the dryer and an exit temperature of less than about 250° C. upon exiting the dryer.
    Type: Grant
    Filed: February 1, 2007
    Date of Patent: May 8, 2012
    Assignee: Grupo Petrotemex, S.A. De C.V.
    Inventors: Kenny Randolph Parker, Philip Edward Gibson
  • Patent number: 8173834
    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: Grant
    Filed: March 20, 2006
    Date of Patent: May 8, 2012
    Assignee: BP Corporation North America Inc.
    Inventor: Thomas M. Bartos
  • Patent number: 8173835
    Abstract: Disclosed is a method and apparatus for drying a wet cake in a carboxylic acid production process. The method comprises employing a contact dryer for drying solid particles of carboxylic acid, where the solid particles can have a residence time of less than about 7 minutes in the dryer and an exit temperature of less than about 250° C. upon exiting the dryer.
    Type: Grant
    Filed: February 1, 2007
    Date of Patent: May 8, 2012
    Assignee: Grupo Petrotemex, S.A. DE C.V.
    Inventors: Kenny Randolph Parker, Philip Edward Gibson
  • Patent number: 8168819
    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: Grant
    Filed: April 4, 2007
    Date of Patent: May 1, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Junya Nishiuchi
  • Patent number: 8163954
    Abstract: Catalytic compositions for conversion of substituted aromatic feed materials to oxidized products comprising aromatic carboxylic acid derivatives of the substituted aromatic feed materials comprise a combination comprising a palladium component, an antimony component and/or a bismuth component, and one or more Group 4, 5, 6 or 14 metal or metalloid components. A process for oxidizing substituted aromatic feed materials comprises contacting the feed material with oxygen in the presence of such a catalytic composition in a liquid reaction mixture.
    Type: Grant
    Filed: May 4, 2007
    Date of Patent: April 24, 2012
    Assignee: BP Corporation North America Inc.
    Inventors: Wayne P. Schammel, Victor Adamian, Stephen P. Brugge, William H. Gong, Peter D. Metelski, Philip O. Nubel, Chengxiang Zhou
  • Patent number: 8153840
    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 22, 2010
    Date of Patent: April 10, 2012
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Thomas Earl Woodruff, Alan George Wonders
  • Patent number: 8115029
    Abstract: Oxidations of hydrocarbons, cycloalkanes and alkenes, arylalkanes, and a variety of other organic substrates are accomplished by cobalt-N-hydroxysuccinimide co-catalyzed reactions with dioxygen under unusually mild, near ambient conditions of temperature and pressure. The improved safety of the oxidation method and the high yields of product obtained make use of a unique combination of cobalt (II) complexes with N-hydroxysuccinimide. These autoxidation reactions do not have prolonged initiation times. Many of these reactions can be safely performed under normal chemical laboratory conditions and do not require specialized equipment or reagents.
    Type: Grant
    Filed: November 2, 2007
    Date of Patent: February 14, 2012
    Assignee: University of Kansas
    Inventors: Richard S. Givens, Chi Cheng Ma, Daryle H. Busch, Bala Subramaniam, Bhuma Rajagopalan
  • Publication number: 20120004451
    Abstract: A process for producing terephthalic acid from para-xylene. The process comprises forming a mixture comprising the para-xylene, a solvent, a bromine source, a catalyst, and ammonium acetate; and oxidizing the para-xylene by contacting the mixture with an oxidizing agent at oxidizing conditions to produce a solid oxidation product comprising terephthalic acid, para-toluic acid, 4-carboxybenzaldehyde. 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: June 8, 2011
    Publication date: January 5, 2012
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Publication number: 20120004449
    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, and a catalyst; 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 an ionic liquid selected from the group consisting of an imidazolium ionic liquid, a pyridinium ionic liquid, a phosphonium ionic liquid, a tetra alkyl ammonium ionic liquid, and combinations thereof. The catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium.
    Type: Application
    Filed: June 8, 2011
    Publication date: January 5, 2012
    Applicants: Boreskov Institute of Catalysis, UOP LLC
    Inventors: Alakananda Bhattacharyya, Joseph A. Kocal, Joel T. Walenga, Nikolay Y. Adonin, Nina L. Kuznetsova, Bair S. Bal'zhinimaev