Producing Carboxyl Group By Oxidation Patents (Class 560/77)
  • 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
  • Patent number: 8859801
    Abstract: The present invention relates to the 3,4-Dicarboalkoxybiphenyl-3?,4?-dicarboxylic acid (including the corresponding acid anhydride) represented by the general formula (1): wherein R11 and R12 each represents an alkyl group having 1 to 4 carbon atoms, and n represents the number of waters of hydration that is 0 or 1.
    Type: Grant
    Filed: October 7, 2011
    Date of Patent: October 14, 2014
    Assignee: Ube Industries, Ltd.
    Inventors: Yasushi Yamamoto, Yasutaka Yoshida, Hikaru Yatabe, Yoshihiro Yamauchi, Tetsurou Tsuji
  • Publication number: 20140275607
    Abstract: In a process for producing a methyl-substituted biphenyl compound, at least one methyl-substituted cyclohexylbenzene compound of the formula: wherein each of m and n is independently an integer from 1 to 3, is contacted with a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising at least one methyl-substituted biphenyl compound. The dehydrogenation catalyst comprises an element or compound thereof from Group 10 of the Periodic Table of Elements deposited on a refractory support, such as alumina.
    Type: Application
    Filed: March 7, 2014
    Publication date: September 18, 2014
    Inventors: Jihad M. Dakka, Chuansheng Bai, James J. Tanke, Gregory J. De Martin, Mary T. Van Nostrand, Michael Salciccioli, Ali A. Kheir, Neeraj Sangar
  • Publication number: 20140275606
    Abstract: In a process for producing a methyl-substituted biphenyl compound, at least one methyl-substituted cyclohexylbenzene compound of the formula: is contacted with a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising at least one methyl-substituted biphenyl compound, wherein each of m and n is independently an integer from 1 to 3 and wherein the dehydrogenation catalyst comprises (i) an element or compound thereof from Group 10 of the Periodic Table of Elements and (ii) tin or a compound thereof.
    Type: Application
    Filed: March 7, 2014
    Publication date: September 18, 2014
    Inventors: Chuansheng Bai, Jihad M. Dakka, Lorenzo C. DeCaul
  • Publication number: 20140213709
    Abstract: Provided are compounds of the following: wherein R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is the residue of a C4 to C14 OXO-alcohol. Also provided are processes for making the compounds and plasticized polymer compositions containing said compounds.
    Type: Application
    Filed: January 28, 2013
    Publication date: July 31, 2014
    Applicant: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
    Inventor: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
  • Publication number: 20140107373
    Abstract: A polyvalent vinyl aromatic compound represented by chemical formula (4) is produced by reacting (1) a specific vinyl aromatic compound and (2) a specific vinyl compound in the presence of (3-1) a metal complex and (3-2) a percarboxylic acid or a hypervalent iodine compound so that a vinyl group derived from the vinyl compound is introduced onto a carbon atom that is adjacent to the carbon atom to which a vinyl group is bonded in the vinyl aromatic compound. (In the formula, Ar represents a monocyclic aromatic hydrocarbon group or the like; R1a represents a —CH2OC(?O)R4 group or the like; R2 represents a hydrogen atom or the like; R3 represents a hydrogen atom or the like; A represents an alkyl group having 1-20 carbon atoms, or the like; and n represents an integer of 1-m.
    Type: Application
    Filed: May 18, 2012
    Publication date: April 17, 2014
    Applicant: Tokyo Instutute of Technology
    Inventors: Koichi Mikami, Hiroki Serizawa, Norimichi Saito
  • Patent number: 8541615
    Abstract: Disclosed is a method for producing a biphenyltetracarboxylic acid ester by oxidative coupling a phthalic acid ester by using a catalyst comprising at least a palladium salt, a copper salt and a ?-dicarbonyl compound in the presence of a molecular oxygen, wherein the ?-dicarbonyl compound is supplied into a reaction mixture liquid intermittently at an interval of less than 30 minutes, or continuously. This method allows, in particular, the selective and economical production of an asymmetric biphenyltetracarboxylic acid tetraester such as 2,3,3?,4?-biphenyltetracarboxylic acid tetraester.
    Type: Grant
    Filed: August 6, 2009
    Date of Patent: September 24, 2013
    Assignee: Ube Industries, Ltd.
    Inventors: Masayuki Nishio, Hiroaki Imajima, Takato Nakamura, Yoshihiro Yamauchi
  • Publication number: 20130197261
    Abstract: The present invention relates to the 3,4-Dicarboalkoxybiphenyl-3?,4?-dicarboxylic acid (including the corresponding acid anhydride) represented by the general formula (1): wherein R11 and R12 each represents an alkyl group having 1 to 4 carbon atoms, and n represents the number of waters of hydration that is 0 or 1.
    Type: Application
    Filed: October 7, 2011
    Publication date: August 1, 2013
    Applicant: UBE INDUSTRIES, LTD.
    Inventors: Yasushi Yamamoto, Yasutaka Yoshida, Hikaru Yatabe, Yoshihiro Yamauchi, Tetsurou Tsuji
  • Publication number: 20120279570
    Abstract: Disclosed herein is a method for preparing large soluble graphenes. The method comprises attaching one or more hindering groups to the graphene, which can prevent face-to-face graphene stacking by reducing the effects of inter-graphene attraction. The large graphenes can absorb a wide spectrum of light from UV to near infrared, and are useful in photovoltaic devices and sensitizers in nanocrystalline solar cells.
    Type: Application
    Filed: January 7, 2011
    Publication date: November 8, 2012
    Applicant: INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION
    Inventors: Liang-shi Li, Xin Yan
  • Publication number: 20120035308
    Abstract: Mono- or diester plasticizers of the formula: wherein A is either —OC(O)R? or ?O, and X is either —COC(O)R or —C(O)OR, and R and R? are C3 to C13 alkyl, which are the same or different, formed from cyclohexylbenzene and processes of making them.
    Type: Application
    Filed: August 3, 2011
    Publication date: February 9, 2012
    Applicant: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
    Inventors: Kun Wang, Jihad Mohammed Dakka, Edmund John Mozeleski, Francisco Manuel Benitez, Lisa Saunders Baugh, Allen David Godwin, Diana S. Smirnova, Stephen Zushma
  • Publication number: 20110137069
    Abstract: Disclosed is a method for producing a biphenyltetracarboxylic acid ester by oxidative coupling a phthalic acid ester by using a catalyst comprising at least a palladium salt, a copper salt and a ?-dicarbonyl compound in the presence of a molecular oxygen, wherein the ?-dicarbonyl compound is supplied into a reaction mixture liquid intermittently at an interval of less than 30 minutes, or continuously. This method allows, in particular, the selective and economical production of an asymmetric biphenyltetracarboxylic acid tetraester such as 2,3,3?,4?-biphenyltetracarboxylic acid tetraester.
    Type: Application
    Filed: August 6, 2009
    Publication date: June 9, 2011
    Applicant: UBE INDUSTRIES, LTD.
    Inventors: Masayuki Nishio, Hiroaki Imajima, Takato Nakamura, Yoshihiro Yamauchi
  • Publication number: 20100168372
    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: Application
    Filed: December 31, 2008
    Publication date: July 1, 2010
    Inventors: Corrado Berti, Enrico Binassi, Martino Colonna, Maurizio Fiorini, Ganesh Kannan, Sreepadaraj Karanam, Marzia Mazzacurati, Ihab Odeh
  • Publication number: 20090215978
    Abstract: A process for the alkoxyalkylation of an unsubstituted aromatic substrate or a substituted aromatic substrate, said substitution being via a carbon-carbon bond, said process comprising reacting the aromatic substrate with a dialkoxyalkane in the presence of a catalyst.
    Type: Application
    Filed: February 21, 2006
    Publication date: August 27, 2009
    Applicant: Davy Process Technology Limited
    Inventors: Simon Darby Roberts, Stephan William Colley
  • Patent number: 7569720
    Abstract: This invention relates to newly identified ester-linked gemini surfactant compounds, to the use of such compounds and to their production. The invention also relates to the use of the ester-linked gemini surfactant compounds to facilitate the transfer of polynucleotides into cells.
    Type: Grant
    Filed: August 4, 2008
    Date of Patent: August 4, 2009
    Assignee: Glaxo Group Limited
    Inventors: Mariano Javier Castro, Christopher Kitson, Mark Ladlow, Alpesh Patel
  • Patent number: 7528277
    Abstract: The present invention relates to a method for obtaining a carboxylic acid ester from an aqueous solution of the corresponding carboxylic acid ammonium salt using alcoholysis. The recovered carboxylic acid ester may be subsequently hydrolyzed to produce the corresponding carboxylic acid.
    Type: Grant
    Filed: December 21, 2005
    Date of Patent: May 5, 2009
    Assignee: E.I. DuPont de Nemours and Company
    Inventors: F. Glenn Gallagher, Robert DiCosimo
  • Publication number: 20080132714
    Abstract: Esters are prepared from hydroxyl-containing compounds and carboxylic acids or anhydrides or lower alkyl esters thereof using a multiple catalyst approach, wherein a first catalyst such as an organotin catalyst can be present at the beginning of the reaction and a second catalyst such as an organotitanium catalyst can be added any time after the addition of the first catalyst, or when the acid value of the reaction mixture falls below a predetermined acid value. The second catalyst can be added multiple times, and a third or additional catalysts can also be used.
    Type: Application
    Filed: May 9, 2005
    Publication date: June 5, 2008
    Inventor: D. Kip Hillshafer
  • Patent number: 7098360
    Abstract: The invention provides processes and apparatus for the production of materials requiring a plurality of chemical reaction steps. In the prior art the number of reaction vessels is minimized by performing two or more reactions together in the same vessel. Instead each process is separated into separate successive steps, in each of which at least two principal components are reacted together, with or without at least one catalyst. In each step the components are reacted under optimum conditions for that reaction, using motion-augmented, sub-Kolmogoroff, micro-agitation provided by a separate discrete motor-operated, micro-agitation means. Such means are much smaller in size, but are extremely flexible as to the flow rate and reaction conditions, so that they can be adjusted to suit the reaction, without compromises dictated by attempting to perform other reactions in the same vessel.
    Type: Grant
    Filed: July 16, 2002
    Date of Patent: August 29, 2006
    Assignee: Kreido Laboratories
    Inventors: Richard A. Holl, James E. Doss, Eric A. Gulliver
  • Patent number: 7070712
    Abstract: There is disclosed a liquid crystalline polyacetylene having a repeat structure of the formula where spa is a spacer group and mes is a mesogenic substituent.
    Type: Grant
    Filed: April 12, 2005
    Date of Patent: July 4, 2006
    Assignee: The Hong Kong University of Science & Technology
    Inventors: Ben Zhong Tang, Wing Yip Lam, Xiangxing Kong, Hoi Sing Kwok
  • Patent number: 6831195
    Abstract: A method for producing an organic acid and/or an organic acid ester which utilizes a steam system permitting stable production of an organic acid and/or an organic acid ester and realizing a high thermal efficiency constantly relative to the waste heat generated in the process of the production is provided. More particularly, this invention concerns a method for the production of an organic acid and/or an organic acid ester, wherein heat generated in the process for producing an organic acid and/or an organic acid ester is recovered in the form of steam, and the steam is used in any of the following forms: {circle around (1)} thermal energy, {circle around (2)} dynamic energy, and {circle around (3)} electrical energy in the process for producing an organic acid and/or an organic acid ester.
    Type: Grant
    Filed: August 21, 2002
    Date of Patent: December 14, 2004
    Assignee: Nippon Shokubai, Co., LTD
    Inventors: Takeshi Nishimura, Tetsuji Mitsumoto, Kazuhiko Sakamoto, Hidefumi Haramaki
  • Publication number: 20030130537
    Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) 1
    Type: Application
    Filed: October 3, 2002
    Publication date: July 10, 2003
    Applicant: Clariant GmbH
    Inventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
  • Patent number: 6495710
    Abstract: The synthesis of dimethyl-1,5-naphthalenedicarboxylate and polymers and articles formed therefrom is disclosed, as well as applications for dimethyl-1,5-naphthalenedicarboxylate, its corresponding acid 1,5-NDA, and various synthesis intermediates.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: December 17, 2002
    Assignee: BP Corporation North America Inc.
    Inventors: John A. Macek, Bruce I. Rosen, Juergen K. Holzhauer, John S. Bramlet, Larry D. Lillwitz, David J. Schneider, Lawrence L. Lang, Edward E. Paschke, John M. Weis, Yenamandra Viswanath, Stefanos L. Sakellarides
  • Publication number: 20020173673
    Abstract: This invention provides a process for purifying the crude aromatic dicarboxylic acids produced by oxidation of dialkyl aromatic hydrocarbons and for using the purified acids in the preparation of polyethylene terephthalate, polyethylene naphthalate and other polyesters. The invention simplifies the manufacturing process by converting the crude aromatic acids into bis-glycol esters in an esterification reactor 4, from which the esterified partial oxidation impurities present in the oxidation product are removed by distillation in distillation tower 5. After removal of the volatile impurities, the dicarboxylic acid esters can separated by distillation in distillation tower 6 or by crystallization and converted to polyesters by polycondensation. The volatile impurities reoved as overhead from tower 5 can be recycled as stream 16 to the oxidation reactor where they act as oxidation promoters thereby optionally allowing for a bromine-free oxidation process for dialkyl aromatic hydrocarbons.
    Type: Application
    Filed: May 18, 2001
    Publication date: November 21, 2002
    Inventors: Krishna Kulai Rao, Russell D. Sellen, Xiaobing Feng
  • Publication number: 20020173674
    Abstract: This invention provides a process for purifying the crude aromatic dicarboxylic acids produced by oxidation of dialkyl aromatic hydrocarbons and for using the purified acids in the preparation of polyethylene terephthalate, polyethylene naphthalate and other polyesters. The invention simplifies the manufacturing process by converting the crude aromatic acids into bis-glycol esters in an esterification reactor 4, from which the esterified partial oxidation impurities present in the oxidation product are removed by distillation in distillation tower 5. After removal of the volatile impurities, the dicarboxylic acid esters can separated by distillation in distillation tower 6 or by crystallization and converted to polyesters by polycondensation. The volatile impurities reoved as overhead from tower 5 can be recycled as stream 16 to the oxidation reactor where they act as oxidation promoters thereby optionally allowing for a bromine-free oxidation process for dialkyl aromatic hydrocarbons.
    Type: Application
    Filed: April 26, 2002
    Publication date: November 21, 2002
    Inventors: Krishna Kulai Rao, Russell D. Sellen, Xiaobing Feng, James Spanswick, William F. Huber
  • Publication number: 20020169203
    Abstract: The present invention relates to ion channel modulating agents. More particularly, the present invention relates to a particular class of chemical compounds that has proven useful as modulators of SK Ca, IK Ca and BK Ca channels. In further aspects, the present invention relates to the use of these SK/IK/BK channel modulating agents for the manufacture of medicaments, for methods of therapy, and pharmaceutical compositions comprising the SK/IK/BK channel modulating agents. The SK/IK/BK channel modulating agents of the invention are useful for the treatment or alleviation of diseases and conditions associated with the SK/IK/BK channels.
    Type: Application
    Filed: May 15, 2001
    Publication date: November 14, 2002
    Inventors: Bo Skaaning Jensen, Dorte Strobaek, Palle Christophersen, Lene Teuber, Jurgen Beyer
  • Patent number: 6329547
    Abstract: The present invention provides compounds represented by the following general formula [I] and salts thereof, which are useful as therapeutic agents for glaucoma, wherein R1 is H, lower alkyl or phenyl, and the phenyl can be substituted by lower alkyl, hydroxy, lower alkoxy, halogen, nitro or phenyl; R2 and R3, being the same or different, are H, halogen or lower alkyl; R4 and R5, being the same or different, are H, lower alkyl or carboxyl or ester thereof; and R6 is carboxyl or phosphono or ester thereof.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: December 11, 2001
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Eiichi Shirasawa, Koji Konomi, Masaki Ichikawa, Hiroshi Suhara
  • Publication number: 20010031852
    Abstract: The synthesis of dimethyl-1,5-naphthalenedicarboxylate and polymers and articles formed therefrom is disclosed, as well as applications for dimethyl-1,5-naphthalenedicarboxylate, its corresponding acid 1,5-NDA, and various synthesis intermediates.
    Type: Application
    Filed: January 12, 2001
    Publication date: October 18, 2001
    Inventors: John A. Macek, Bruce I. Rosen, Juergen K. Holzhauer, John S. Bramlet, Larry D. Lillwitz, David J. Schneider, Lawrence L. Lang, Edward E. Paschke, John M. Weis, Yenamandra Viswanath, Stefanos L. Sakellarides
  • Patent number: 6297348
    Abstract: Disclosed is a method for closely linking a process for producing 2,6-naphthalene dicarboxylic acid (2,6-NDA) with a process for producing polyethylene naphthalate, thus eliminating the need for drying 2,6-NDA, handling solid 2,6-NDA, and optimizing particle size of 2,6-NDA which comprises: a) Adding an aqueous slurry of polymer grade 2,6-NDA directly into a process for making PEN, either by directly adding a stream from a 2,6 NDA process into a PEN process, or by adding water to polymer grade 2-6-NDA prior to adding the resulting slurry to a PEN process. b) Removing the slurry water during the first esterification reaction at the same time the water of reaction is removed.
    Type: Grant
    Filed: August 22, 2000
    Date of Patent: October 2, 2001
    Assignee: Shell Oil Company
    Inventors: John Bernard Rodden, Glenn William Elliott
  • Publication number: 20010007910
    Abstract: Improved process for producing carboxylic acids or their esters by catalytic liquid phase oxidation of a corresponding precursor in a suitable solvent comprising feeding the reactants to a first oxidation reaction zone at high pressure and high solvent ratio, wherein uptake of oxygen is limited to less than 50% of the oxygen required for full conversion of the precursor to its corresponding carboxylic acid, and then feeding the resulting reaction medium to a second oxidation reaction zone.
    Type: Application
    Filed: January 9, 2001
    Publication date: July 12, 2001
    Inventors: Samuel D. Housley, John A. Turner
  • Patent number: 6197216
    Abstract: A novel ferrielectric liquid crystal compound of the formula (1), wherein R is a linear alkyl group having 6 to 12 carbon atoms, X is a hydrogen atom or a fluorine atom, m is an integer of 1 to 3, n is an integer of 1 to 3, and C* is an asymmetric carbon atom. The ferrielectric liquid crystal compound of the invention characteristically has a ferrielectric phase in a broad temperature range and shows a high speed optical response in spite of a small spontaneous polarization.
    Type: Grant
    Filed: September 28, 1999
    Date of Patent: March 6, 2001
    Assignee: Mitsubishi Gas Chemical Co INC
    Inventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui
  • Patent number: 6160159
    Abstract: The invention is directed to a process for the production of terephthalic acid and esters thereof from p-tolualdehyde or mixtures of p-tolualdehyde and p-xylene. The process of the invention can be carried out at lower temperatures and faster throughput than conventional processes using p-xylene. The use of p-tolualdehyde facilitates safety considerations by eliminating the induction period and high oxiding fluid concentrations encountered in typical oxidation reactions which use only p-xylene as the terephthalic acid or ester precursor.
    Type: Grant
    Filed: July 30, 1999
    Date of Patent: December 12, 2000
    Assignee: Arteva North America, S.a.r.l.
    Inventor: Brad Lee Smith
  • Patent number: 6133470
    Abstract: A process for producing terephthalic acid and/or dimethyl terephthalate includes contacting a toluene-containing reaction stream with a first catalyst under toluene disproportionation conditions to produce an intermediate product stream of para-xylene with negligible ortho-xylene. The first catalyst includes a crystalline molecular sieve which has an ortho-xylene diffusion rate of at least 50 minutes. The first catalyst can be modified by selectivation with a silicon compound or carbon compound. The intermediate product stream, without need for para-xylene purification, is oxidized to terephthalic acid or dimethyl terephthalate.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: October 17, 2000
    Assignee: Mobil Oil Corporation
    Inventors: Jeffery S. Beck, David L. Stern
  • Patent number: 6028211
    Abstract: Methods for reducing the fouling of process equipment used in the manufacture of aromatic compounds such as dimethyl-2,6-naphthalenedicarboxylate are disclosed. The methods require treating manufacturing process streams with a metal complexing agent. Novel compositions useful in the manufacture of aromatic materials such as dimethyl-2,6-naphthalenedicarboxylate also are disclosed.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: February 22, 2000
    Assignee: BP Amoco Corporation
    Inventors: Allen B. Mossman, David A. Young, Paul K. Behrens, Juergen K. Holzhauer
  • Patent number: 5877341
    Abstract: Methods and devices for controlling the reaction rate of a hydrocarbon to an acid or other intermediate oxidation product by pressure drop rate adjustments. The pressure drop rate measurements arc conducted at predetermined time intervals, after stopping the feeding and exiting of gases. The pressure drop at a predetermined time interval is measured or the time it takes for the pressure to drop by a certain degree. Adjustments are then made in one or more temperature, feeding rates of hydrocarbon, solvent, catalyst, promoter, and the like until the pressure drop rate and the reaction rate fall within desirable predetermined limits.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: March 2, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Eustathios Vassiliou, Mark W. Dassel, David C. DeCoster, Ader M. Rostami, Sharon M. Aldrich
  • Patent number: 5869736
    Abstract: A process is provided for the oxidation of p-xylene and methyl p-tolulate with oxygen-containing gases in the Witten-Hercules process for preparing dimetyl terephthalate in at least two sequentially arranged stages and in the presence of a catalyst, wherein the process involves oxidizing p-xylene and methyl p-toluate with oxygen containing gases in at least two sequential stages in the presence of a catalyst, wherein the at least two sequential stages include at least one p-xylene rich stage and at least one methyl p-toluate rich stage, wherein at least one of the following steps (a) and (b) occurs:(a) in the at least one p-xylene rich stage at least a portion of p-xylene present is oxidized in the presence of 5 to 30% by mass of methyl p-toluate, based on a total amount of oxidation mixture in the at least one p-xylene rich stage; or(b) in the methyl p-toluate rich stage at least one of methyl p-toluate or p-toluic acid is oxidized in the presence of 2 to 30% by mass of p-xylene, based on a total amount of m
    Type: Grant
    Filed: October 14, 1997
    Date of Patent: February 9, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Stefan Jelko, Anton Schoengen, Hermann-Josef Korte, Gerhard Franz, Hans-Guenther Srebny, Thomas Jostmann, Frank Steding
  • Patent number: 5852201
    Abstract: A process for preparing crude dimethyl terephthalate, comprises oxidizing a mixture comprising para-xylene and methyl para-toluate, esterifying the oxidized mixture with methanol, separating the resulting crude ester into fractions. By separating the crude ester with a distillation column containing structured packing and using a lower bottom temperature, product yield is increased, and the process is made more economical.
    Type: Grant
    Filed: January 17, 1997
    Date of Patent: December 22, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Udo Lenz, Ulrich Neutzler, Anton Schoengen, Reinhard Sigg
  • Patent number: 5614159
    Abstract: In the purification of an off-gas stream originating from a process of oxidizing a liquid mixture of para-xylene with methyl para-toluate with an oxygen-containing gas under pressure, the off-gas being contaminated with at least one of an aliphatic and an aromatic impurity, which comprises expanding the off-gas stream in an expansion turbine for generating mechanical or electrical energy so as to obtain an at least partial recovery of the energy contained in the off-gas, the improvement comprising subjecting the off-gas to at least one absorption step under pressure to remove at least one component from the off-gas and subjecting the resultant off-gas stream to combustion under a pressure of more than 3 bar prior to expanding the off-gas stream in the expansion turbine.
    Type: Grant
    Filed: April 10, 1995
    Date of Patent: March 25, 1997
    Assignee: Huls Aktiengesellschaft, Werk Troisdorf
    Inventors: Rudolf Modic, Hermann-Josef Korte, Anton Schoengen, Johann-Heinrich Schroeder, J org Porschen
  • Patent number: 5587508
    Abstract: A process for producing 2,6-naphthalenedicarboxylic acid (NDCA) is disclosed. This process comprises oxidizing a 2,6-dialkylnaphthalene with a gas containing molecular oxygen in a solvent containing a lower aliphatic carboxylic acid in the presence of a catalyst comprising heavy metal compounds and a bromine compound, and is characterized in that an ester mixture containing dimethyl 2,6-naphthalenedicarboxylate (NDCM) is added to the oxidation reaction. The low boiling distillate, the high boiling still residue, and the residue of the mother liquor after recrystallization, occurring during purification of the crude NDCM, are also used as additives to the oxidation reaction. According to the present invention, NDCA with large particle size and bulk density can be obtained. Therefore, solid-liquid separation of the crystals, drying of the separated crystals and transportation of the dried crystals are made easier.
    Type: Grant
    Filed: January 3, 1996
    Date of Patent: December 24, 1996
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Hiroshi Machida
  • Patent number: 5350874
    Abstract: A continuous process for preparing a dialkylester of a naphthalenedicarboxylic acid comprising passing a liquid phase reaction mixture comprising a low molecular weight alcohol, a naphthalenedicarboxylic acid and a dialkylester of a naphthalenedicarboxylic acid at an elevated temperature through series arranged reaction zones while introducing a naphthalenedicarboxylic acid and a low molecular weight alcohol to an upstream reaction zone, agitating at least one reaction zone, and removing a liquid product mixture comprising the dialkylester of the naphthalenedicarboxylic acid produced by the reaction of the naphthalenedicarboxylic acid with the low molecular weight alcohol from a downstream reaction zone.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: September 27, 1994
    Assignee: Amoco Corporation
    Inventors: Paul K. Behrens, Juergen K. Holzhauer, Gregory P. Hussmann, David L. Sikkenga
  • Patent number: 5338882
    Abstract: The invention relates to a process for the production of a DMT intermediate product as well as its working up to fibregrade DMT and to medium pure and pure terephthalic acid.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: August 16, 1994
    Assignee: Huls Aktiengesellschaft
    Inventors: Hermann-Josef Korte, Anton Miletic, Hans U. Neutzler, Anton Schoengen, Johann H. Schroeder, Ralf Wirges
  • Patent number: 5334754
    Abstract: Provided is a process for preparing 2,5-diphenylterephthalic acid, which is useful in preparing certain polyesters, especially liquid-crystalline polyesters. In this process, p-xylene is di-alkylated with cyclohexene to provide 2,5-dicyclo-hexyl-p-xylene, which is in turn dehydrogenated to provide 2,5-diphenylxylene. 2,5-Diphenylxylene is then oxidized to provide 2,5-diphenylterephthalic acid by utilization of a cobaltous/manganous/bromide oxidation system.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: August 2, 1994
    Assignee: Eastman Chemical Company
    Inventors: Charles E. Sumner, Jr., Bruce L. Gustafson, Ernest W. Arnold, III, Eric J. Fugate, Dewey W. Fuller, Jr.
  • Patent number: 5286896
    Abstract: The invention relates to a process for the production of a DMT intermediate product as well as its working up to fibregrade DMT and to medium pure and pure terephthalic acid.
    Type: Grant
    Filed: August 15, 1991
    Date of Patent: February 15, 1994
    Assignee: Huls Aktiengesellschaft
    Inventors: Hermann-Josef Korte, Anton Miletic, Hans U. Neutzler, Anton Schoengen, Johann H. Schroeder, Ralf Wirges
  • Patent number: 5254719
    Abstract: A process for preparing purified dimethyl-2,6-naphthalenedicarboxylate by the esterification of 2,6-naphthalenedicarboxylic acid is disclosed, and which process provides for the efficient removal of residual oxidation catalyst metals from the dimethyl-2,6-naphthalenedicarboxylate and efficient removal of particulate contaminants.
    Type: Grant
    Filed: May 31, 1991
    Date of Patent: October 19, 1993
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, David A. Young
  • Patent number: 5202469
    Abstract: Partially fluorinated dicarboxylic acid and the acid chloride thereof, a process for its preparation and its use.The compound of the formula (I) ##STR1## and the acid chloride thereof are prepared by air oxidation in the presence of a catalyst mixture composed of the ions of cobalt, manganese and bromine in an acid organic medium. The compounds can be used for the preparation of linear polycarboxamides and polycarboxylic acid esters.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: April 13, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
  • Patent number: 5138025
    Abstract: A method for stabilizing molten diesters of naphthalenedicarboxylic acids and stabilized naphthalenedicarboxylic acid diester compositions are disclosed.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: August 11, 1992
    Assignee: Amoco Corporation
    Inventor: Allen B. Mossman
  • Patent number: 5101050
    Abstract: A process for the production of aromatic esters or aromatic anhydrides with improved color properties is disclosed. This process comprises treating the aromatic ester or aromatic anhydride with an activated boric acid followed by fractionation.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: March 31, 1992
    Assignee: Amoco Corporation
    Inventors: Chang M. Park, Ronald Coates, Juergen K. Holzhauer, John V. Peterson
  • Patent number: 5095135
    Abstract: A process for the preparation of naphthalenecarboxylic acid esters in which a substituted naphthalene is oxidized with molecular oxygen in the presence of a heavy metal-based catalyst in a solvent comprising a lower aliphatic monocarboxylic acid to form a naphthalenecarboxylic acid and the resulting acid is then esterified. The esterified product is purified by washing, recrystallization, and distillation in that order. Heavy metals are recovered as carbonates from filtrates and washings obtained by seeparation of crude acid and ester products and by washing thereof.
    Type: Grant
    Filed: April 4, 1991
    Date of Patent: March 10, 1992
    Assignee: Sumikin Chemical Co., Ltd.
    Inventors: Teruaki Yamada, Kazuhiko Maeda, Ryohei Minami, Yukio Nagao, Kazuki Sugiura
  • Patent number: 4952721
    Abstract: A process is disclosed for the oxidation of esters of para- and meta-methyl-substituted phenols to the corresponding aromatic carboxylic acid in the presence of a promoter comprising an anhydride of a lower aliphatic carboxylic acid and a heavy metal catalyst with or without the presence of bromine. The resulting carboxylic acids are useful in liquid crystal polymers and polymers useful in engineering plastics.
    Type: Grant
    Filed: March 8, 1989
    Date of Patent: August 28, 1990
    Assignee: Amoco Corporation
    Inventor: Kristi A. Fjare
  • Patent number: 4950786
    Abstract: A method for making 2,6-naphthalene dicarboxylic acid by the oxidation of 2,6-diisopropylnaphthalene or its oxidation derivatives in the presence of a catalyst comprising cobalt, manganese, cerium and bromine components is disclosed.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: August 21, 1990
    Assignee: Amoco Corporation
    Inventors: Paul A. Sanchez, David A. Young, George E. Kuhlmann, Walter Partenheimer, Wayne P. Schammel
  • Patent number: 4908471
    Abstract: Disclosed is a method for the production of benzene carboxylic acids and benzene carboxylic acid esters or their mixtures, while p-toloylic acid is made from p-xylene and terephthalic acid monomethyl ester is simultaneously prepared from p-toluylic acid ester. The oxidation is performed by the addition of oxidator liquid and gases containing oxygen in single orifice mixing nozzles with the formation of a highly disperse reaction phase and the single orifice mixing nozzles open into the oxidator liquid.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: March 13, 1990
    Assignee: Huels Troisdorf AG
    Inventors: Hans Leuck, Hans-Jorg Westermann
  • Patent number: 4906772
    Abstract: A process is disclosed for the co-production of aliphatic monocarboxylic acids and polycarboxylic aromatic acids in high selectivity, conversion and yield. The aliphatic monocarboxylic acid can serve as a component of the solvent for the process.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: March 6, 1990
    Assignee: Amoco Corporation
    Inventors: Calvin T. Chew, Rosemary F. McMahon, Kristi A. Fjare, Wayne P. Schammel