Alkyl Side Chain Oxidized Patents (Class 562/409)
  • Patent number: 10604455
    Abstract: The present invention relates to a process for preparing an aromatic hydrocarbon, and processes for producing p-xylene and terephthalic acid. The process for producing said aromatic hydrocarbon comprises a step of contacting an olefin with a diene in the presence of a catalyst to produce an aromatic hydrocarbon, which is characterized in that, at least a part of said olefin is substituted with dienophile. The reaction pressure can be reduced and the xylene selectivity can be increased with the improvement of the present invention.
    Type: Grant
    Filed: October 12, 2016
    Date of Patent: March 31, 2020
    Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPEC
    Inventors: Dejin Kong, Sc Edman Tsang, Ivo Teixeria, Qi Song
  • Patent number: 9428436
    Abstract: An improved process for preparing aromatic carboxylic acids by the exothermic liquid-phase oxidation reaction of an aromatic feedstock compound wherein water is efficiently recovered from the exothermic liquid-phase oxidation reaction and treated to reduce corrosive agents residing therein.
    Type: Grant
    Filed: December 11, 2014
    Date of Patent: August 30, 2016
    Assignee: BP Corporation North America Inc.
    Inventors: Thomas Michael Bartos, David A. Peterson
  • Patent number: 9302971
    Abstract: This invention relates to the production of terephthalic acid by 1) cycloaddition of 2,5 substituted furan (such as 2,5-bis hydroxymethylfuran or 5-hydroxymethylfurfural) and ethylene, and 2) the subsequent oxidation of the dehydrated cycloaddition product to terephthalic acid. The invention relates more particularly to overall biobased pathways for making terephthalic acid from carbohydrates such as hexoses (e.g., glucose or fructose).
    Type: Grant
    Filed: October 16, 2014
    Date of Patent: April 5, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Guang Cao, James R. Lattner, Javier Guzman, Shifang L. Luo
  • Patent number: 9233905
    Abstract: A process for oxidizing and crystallizing alkyl aromatics is described. The solvent and operating conditions are controlled to maintain the aromatic carboxylic acid in solution in the reaction zone, and the aromatic carboxylic acid is crystallized in a downstream crystallizer, resulting in reduced impurity levels in the product.
    Type: Grant
    Filed: December 14, 2012
    Date of Patent: January 12, 2016
    Assignee: UOP LLC
    Inventors: Raymond Shih, Alakananda Bhattacharyya, Carl J Stevens, Joel T. Walenga
  • Publication number: 20150141695
    Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose, starch, sugar) and ethylene in the presence of a catalyst. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF), which may be converted into para-xylene by cycloaddition of ethylene to DMF. Para-xylene can then be oxidized to form terephthalic acid.
    Type: Application
    Filed: October 20, 2014
    Publication date: May 21, 2015
    Applicant: MICROMIDAS, INC.
    Inventors: Makoto N. MASUNO, Patrick B. SMITH, Dennis A. HUCUL, Adina DUMITRASCU, Katherine BRUNE, Ryan L. SMITH, John A. BISSELL, Marc FOSTER
  • Publication number: 20150133627
    Abstract: Methods or preparing para-xylene from biomass by carrying out a Diels-Alder cycloaddition at controlled temperatures and activity ratios. Methods of preparing bio-terephthalic acid and bio-poly(ethylene terephthalate (bio-PET) are also disclosed, as well as products formed from bio-PET.
    Type: Application
    Filed: January 22, 2015
    Publication date: May 14, 2015
    Inventors: INDRA PRAKASH, VENKATA SAI PRAKASH CHATURVEDULA, ROBERT M. KRIEGEL, XIAOYAN HUANG HUANG
  • Patent number: 9024060
    Abstract: Bio-based terephthalic acid (bio-TPA), bio-based dimethyl terephthalate (bio-DMT), and bio-based polyesters, which are produced from a biomass containing a terpene or terpenoid, such as limonene are described, as well as the process of making these products. The bio-based polyesters include poly(alkylene terephthalate)s such as bio-based poly(ethylene terephthalate) (bio-PET), bio-based poly(trimethylene terephthalate) (bio-PTT), bio-based poly(butylene terephthalate) (bio-PBT), and bio-based poly(cyclohexylene dimethyl terephthalate) (bio-PCT).
    Type: Grant
    Filed: December 26, 2013
    Date of Patent: May 5, 2015
    Assignee: Saudi Basic Industries Corporation
    Inventors: Corrado Berti, Enrico Binassi, Martino Colonna, Maurizio Fiorini, Ganesh Kannan, Sreepadaraj Karanam, Marzia Mazzacurati, Ihab Odeh
  • Publication number: 20150099897
    Abstract: Processes have been developed to obtain recycle ionic liquid streams which are active for oxidation of alkyl aromatic compounds, and which reduce the amount of 4-CBA in the solid oxidation products. The process can reduce the makeup amount of ionic liquid, carboxylic acid, catalyst, bromine source, and ammonia source.
    Type: Application
    Filed: October 8, 2013
    Publication date: April 9, 2015
    Applicant: UOP LLC
    Inventors: Avram M. Buchbinder, Raymond Shih, Alakananda Bhattacharyya, Evan B. Jorgenson, Tatsamai Jarusiripipat, Nina Kuznetsova
  • Patent number: 9000214
    Abstract: Methods of purifying crude or contaminated terephthalic acid using ionic liquids are described. Crude or contaminated terephthalic acid is contacted with a solvent in the absence of an oxidizing agent to form a purified product having at least 30 wt % less 4-carboxybenzaldehyde compared to the crude or contaminated terephthalic acid. The solvent consists essentially of an ionic liquid, optionally an ionic solid or a material capable of forming an ionic salt, and optionally an aqueous solvent. The ionic liquid is formed in situ from at least one ionic liquid precursor.
    Type: Grant
    Filed: June 6, 2013
    Date of Patent: April 7, 2015
    Assignee: UOP LLC
    Inventors: Susie C. Martins, Kaitlin DeSalvo, Alakananda Bhattacharyya
  • Publication number: 20150094486
    Abstract: Ionic liquid compositions derived from imidazolium based ionic liquids that have been thermally treated or thermally and oxidatively treated are disclosed. These compositions can be utilized as the medium for oxidation of alkylaromatic compounds and their oxidized derivatives or as a medium for purification of aromatic carboxylic acids.
    Type: Application
    Filed: September 27, 2013
    Publication date: April 2, 2015
    Applicant: UOP LLC
    Inventors: Avram M. Buchbinder, Alakananda Bhattacharyya, Praneeth D. Edirisinghe, Joel T. Walenga
  • Publication number: 20150080546
    Abstract: In a process for producing 3,4? and/or 4,4? dimethyl-substituted biphenyl compounds, a feed comprising toluene is contacted with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluenes. At least part of the hydroalkylation reaction product is dehydrogenated in the presence of a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising a mixture of dimethyl-substituted biphenyl isomers. The dehydrogenation reaction product is then separated into at least a first stream containing at least 50% of 3,4? and 4,4? dimethylbiphenyl isomers by weight of the first stream and at least one second stream comprising one or more 2,x? (where x? is 2?, 3?, or 4?) and 3,3? dimethylbiphenyl isomers.
    Type: Application
    Filed: September 8, 2014
    Publication date: March 19, 2015
    Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Keith H. Kuechler, Neeraj Sangar, Michael Salciccioli, Alan A. Galuska, Gary D. Mohr
  • Publication number: 20150065339
    Abstract: Catalysts prepared from abundant, cost effective metals, such as cobalt, nickel, chromium, manganese, iron, and copper, and containing one or more neutrally charged ligands (e.g., monodentate, bidentate, and/or polydentate ligands) and methods of making and using thereof are described herein. Exemplary ligands include, but are not limited to, phosphine ligands, nitrogen-based ligands, sulfur-based ligands, and/or arsenic-based ligands. In some embodiments, the catalyst is a cobalt-based catalyst or a nickel-based catalyst. The catalysts described herein are stable and active at neutral pH and in a wide range of buffers that are both weak and strong proton acceptors. While its activity is slightly lower than state of the art cobalt-based water oxidation catalysts under some conditions, it is capable of sustaining electrolysis at high applied potentials without a significant degradation in catalytic current. This enhanced robustness gives it an advantage in industrial and large-scale water electrolysis schemes.
    Type: Application
    Filed: July 2, 2014
    Publication date: March 5, 2015
    Inventors: Aaron J. Bloomfield, Stafford W. Sheehan, Samuel L. Collom, Robert H. Crabtree, Paul T. Anastas
  • 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: 8952194
    Abstract: A method of manufacturing aromatic hydrocarbons, which are suitable for the production of terephthalic acid, from tall oil-based raw material. According to the invention, the raw material that contains tall oil or its fraction is catalytically deoxygenated with hydrogen, and one or more aromatic hydrocarbons that can be converted into terephthalic acid are separated from the deoxygenated reaction yield. The deoxygenation catalyst is a NiMo catalyst and, in addition, a cracking catalyst can be used, such as an acidic zeolite catalyst. The separated hydrocarbon can be p-xylene, o-xylene or p-cymene. According to the invention, these can be converted by oxidation and, when needed, by a re-arrangement reaction into terephthalic acid that is suitable for the source material of the manufacture of bio-based polyethylene terephthalate.
    Type: Grant
    Filed: June 3, 2011
    Date of Patent: February 10, 2015
    Assignee: Stora Enso OYJ
    Inventors: Ali Harlin, Jari Räsänen, Tapani Penttinen
  • Patent number: 8946472
    Abstract: Bio-based terephthalic acid (bio-TPA), bio-based dimethyl terephthalate (bio-DMT), and bio-based polyesters, which are produced from a biomass containing a terpene or terpenoid, such as limonene are described, as well as the process of making these products. The bio-based polyesters include poly(alkylene terephthalate)s such as bio-based poly(ethylene terephthalate) (bio-PET), bio-based poly(trimethylene terephthalate) (bio-PTT), bio-based poly(butylene terephthalate) (bio-PBT), and bio-based poly(cyclohexylene dimethyl terephthalate) (bio-PCT).
    Type: Grant
    Filed: December 31, 2008
    Date of Patent: February 3, 2015
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Corrado Berti, Enrico Binassi, Martino Colonna, Maurizio Fiorini, Ganesh Kannan, Sreepadaraj Karanam, Marzia Mazzacurati, Ihab Odeh
  • 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: 8940931
    Abstract: The present invention provides a method, as a means for industrially producing a refined 6-bromo-2-naphthalenecarboxylic acid product from a crude 6-bromo-2-naphthalenecarboxylic acid product, comprising: causing the above crude product to react with sodium hydroxide in water to precipitate a sodium salt of 6-bromo-2-naphthalenecarboxylic acid; performing recrystallization treatment for the obtained precipitate; causing the obtained crystal to react with acid in water to precipitate 6-bromo-2-naphthalenecarboxylic acid; and recovering the obtained precipitate.
    Type: Grant
    Filed: October 28, 2010
    Date of Patent: January 27, 2015
    Assignee: Air Water Inc.
    Inventors: Takeshi Namekata, Ikuo Ito
  • 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
  • Publication number: 20140350294
    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: Application
    Filed: September 14, 2012
    Publication date: November 27, 2014
    Applicant: MICROMIDAS, INC.
    Inventors: Makoto N. Masuno, Douglas Cannon, John Bissell, Ryan L. Smith, Marc Foster, Alex Benjamin Wood, Patrick B. Smith, Dennis A. Hucul
  • Patent number: 8835678
    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: September 16, 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: 8802704
    Abstract: The invention relates to oxadiazole compounds of formula I. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: August 12, 2014
    Assignee: Merck Serono SA
    Inventors: Anna Quattropani, Cyril Montagne, Wolfgang Sauer, Stefano Crosignani, Agnès Bombrun
  • 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
  • Publication number: 20140171679
    Abstract: A process for oxidizing and crystallizing alkyl aromatics is described. The solvent and operating conditions are controlled to maintain the aromatic carboxylic acid in solution in the reaction zone, and the aromatic carboxylic acid is crystallized in a downstream crystallizer, resulting in reduced impurity levels in the product.
    Type: Application
    Filed: December 14, 2012
    Publication date: June 19, 2014
    Applicant: UOP LLC
    Inventors: Raymond Shih, Alakananda Bhattacharyya, Carl J. Stevens, Joel T. Walenga
  • 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
  • Publication number: 20130245316
    Abstract: The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose, starch, sugar) and ethylene in the presence of a catalyst. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF), which may be converted into para-xylene by cycloaddition of ethylene to DMF. Para-xylene can then be oxidized to form terephthalic acid.
    Type: Application
    Filed: March 15, 2013
    Publication date: September 19, 2013
    Applicant: MICROMIDAS, INC.
    Inventors: Makoto N. MASUNO, Patrick B. SMITH, Dennis A. HUCUL, Adina DUMITRASCU, Katherine BRUNE, Ryan L. SMITH, John BISSELL, Marc FOSTER
  • Publication number: 20130178650
    Abstract: A method of manufacturing aromatic hydrocarbons, which are suitable for the production of terephthalic acid, from tall oil-based raw material. According to the invention, the raw material that contains tall oil or its fraction is catalytically deoxygenated with hydrogen, and one or more aromatic hydrocarbons that can be converted into terephthalic acid are separated from the deoxygenated reaction yield. The deoxygenation catalyst is a NiMo catalyst and, in addition, a cracking catalyst can be used, such as an acidic zeolite catalyst. The separated hydrocarbon can be p-xylene, o-xylene or p-cymene. According to the invention, these can be converted by oxidation and, when needed, by a re-arrangement reaction into terephthalic acid that is suitable for the source material of the manufacture of bio-based polyethylene terephthalate.
    Type: Application
    Filed: June 3, 2011
    Publication date: July 11, 2013
    Applicant: STORA ENSO OYJ
    Inventors: Ali Harlin, Jari Räsänen, Tapani Penttinen
  • Publication number: 20130172610
    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 product comprising a mother liquor and at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid; and adding at least a portion of the mother liquor in the contacting step.
    Type: Application
    Filed: December 29, 2011
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Raymond C. Shih
  • Publication number: 20130172609
    Abstract: A process for oxidizing an alkyl-aromatic compound to reduce the level of impurities is described. The solvent pH level controlled to reduce the impurities.
    Type: Application
    Filed: December 29, 2011
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Publication number: 20130172605
    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: Application
    Filed: December 29, 2011
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Publication number: 20130172608
    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: Application
    Filed: December 29, 2011
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Joel T. Walenga
  • Publication number: 20130172606
    Abstract: Methods and apparatus for producing terephthalic acid using a p-xylene stream enriched with p-toluic acid are described. The apparatus includes first and second reactor zones. The reactor zones can be in the same reactor or in different reactors.
    Type: Application
    Filed: December 29, 2011
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Raymond C. Shih
  • Publication number: 20130172607
    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: Application
    Filed: December 29, 2011
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventor: Alakananda Bhattacharyya
  • Publication number: 20120172622
    Abstract: Methods are disclosed for producing, from renewable carbon sources, acetic acid in an economical manner. In particular, these methods are directed to the separation and recovery of acetic acid as a substantial product (e.g., as much as 5% by weight or more) of biomass pyrolysis. For a given commercial biomass pyrolysis unit, the acetic acid yield can represent a significant quantity of that used in a major industrial applications such as purified terephthalic acid (PTA) production. According to some embodiments, pyrolysis conditions and/or flow schemes advantageously improve the recovery of acetic acid for a given purity level.
    Type: Application
    Filed: December 30, 2010
    Publication date: July 5, 2012
    Applicant: UOP LLC
    Inventor: JOSEPH ANTHONY KOCAL
  • 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: 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: 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: 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: 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
  • Publication number: 20120035226
    Abstract: The invention relates to oxadiazole compounds of formula I. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.
    Type: Application
    Filed: March 29, 2010
    Publication date: February 9, 2012
    Applicant: MERCK SERONO SA
    Inventors: Anna Quattropani, Cyril Montagne, Wolfgang Sauer, Stefano Crosignani, Agnés Bombrun
  • Publication number: 20120004450
    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: 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 I. Kuznetsova, Bair S. Bal'zhinimaev
  • 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
  • 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: 8080685
    Abstract: A method for producing benzoic acid or a methylbenzoic acid isomer is disclosed which comprises forming a dispersion comprising oxygen-containing gas bubbles dispersed in either toluene or an xylene isomer, wherein the bubbles have a mean diameter less than 1 micron. The dispersion is then subjected to reaction conditions comprising a pressure of less than about 1013 kPa and a temperature of less than about 160° C., whereby at least a portion of the toluene or xylene isomer is partially oxidized to form benzoic acid or the corresponding methylbenzoic acid isomer, respectively. In some embodiments, the methylbenzoic acid isomer is an intermediate compound, and the method further includes subjecting any unreacted xylene isomer and the intermediate compound to further oxidization, to form 1,2-benzenedicarboxylic acid, 1,3-benzenedicarboxylic acid, or 1,4-benzenedicarboxylic acid. A system of apparatus for performing the method is also disclosed.
    Type: Grant
    Filed: June 12, 2008
    Date of Patent: December 20, 2011
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 8053597
    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: June 26, 2009
    Date of Patent: November 8, 2011
    Assignee: Grupo Petrotemex, S.A. DE C.V.
    Inventors: Philip Edward Gibson, Kenny Randolph Parker, Ronald Buford Sheppard
  • Patent number: 8049036
    Abstract: Alkenes, unsaturated saturated carboxylic acids, saturated carboxylic acids and their higher analogues are prepared cumulatively from corresponding alkanes utilizing using a multi-staged catalyst system and a multi-stage process which comprises steam cracking of alkanes to corresponding alkenes at flame temperatures and at short contact times in combination with one or more oxidation catalysts for catalytically converting the corresponding alkenes to further corresponding oxygenated products using short contact time reactor conditions.
    Type: Grant
    Filed: January 18, 2008
    Date of Patent: November 1, 2011
    Assignee: Rohm and Haas Company
    Inventors: Abraham Benderly, Anne Mae Gaffney, Mark Anthony Silvano
  • Patent number: 7960581
    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: July 29, 2010
    Date of Patent: June 14, 2011
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Marcel de Vreede, Alan George Wonders, Robert Lin