Initiator Or Promoter Used With Catalyst Patents (Class 562/417)
  • Patent number: 10676420
    Abstract: A process for producing terephthalic acid, comprising: passing a feed stream through a catalytic reactor wherein the feed stream comprises p-xylene; contacting the feed stream with a catalyst within the catalytic reactor to produce an oxidation reaction wherein the catalyst comprises, less than or equal to 10% of a metal component wherein the metal component comprises cobalt ions, manganese ions, or a combination comprising at least one of the foregoing, less than or equal to 15% bromide ions, and less than or equal to 2% silver ions; and producing a product stream comprising terephthalic acid, wherein the product stream exits the catalytic reactor.
    Type: Grant
    Filed: October 17, 2016
    Date of Patent: June 9, 2020
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Syed Azhar Hashmi, Labeeb A. Chaudhary, Nedumbamana Sankaran
  • 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: 20140100386
    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: Application
    Filed: December 12, 2013
    Publication date: April 10, 2014
    Applicant: UOP LLC
    Inventor: Alakananda Bhattacharyya
  • 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: 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: 8410308
    Abstract: Disclosed is a process for the production of an oxygen-containing organic compound by oxidizing an organic compound with molecular oxygen in a liquid phase in the presence both of a catalytic nitrogen-containing cyclic compound and a catalyst including a solid superacid and, supported thereon, a transition metal compound, in which the nitrogen-containing cyclic compound contains, as a ring constituent, a skeleton represented by following Formula (1), wherein X represents an —OR group, and wherein R represents hydrogen atom or a hydroxyl-protecting group. The process gives the oxygen-containing organic compound in a high yield and enables easy recovery and reuse of the catalyst.
    Type: Grant
    Filed: February 27, 2009
    Date of Patent: April 2, 2013
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Minoru Takano, Naruhisa Hirai, Yasutaka Ishii
  • Patent number: 8321082
    Abstract: In a hybrid vehicle, control is executed to operate an engine with fuel injection being performed, when an unexecuted percentage of catalyst degradation suppression control is equal to or greater than a threshold value of the unexecuted percentage, when a power storage percentage of a battery is equal to or greater than a threshold value of the power storage percentage and the battery is charging, and also when a vehicle speed is equal to or greater than a threshold value of the vehicle speed and a cumulative air amount is equal to or greater than a threshold value of the cumulative air amount, when a catalyst temperature is less than a first threshold temperature and equal to or greater than a second threshold temperature, when the catalyst temperature is equal to or greater than the first threshold temperature, when there is a braking request while the engine is operating.
    Type: Grant
    Filed: September 13, 2011
    Date of Patent: November 27, 2012
    Assignee: Toyota Jidosha Kabushiki Kaisha
    Inventor: Yasushi Ando
  • 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: 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: 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
  • Publication number: 20110071314
    Abstract: A process for producing an aromatic polycarboxylic acid in which all alkyl groups are converted into carboxyl groups in a high yield by decreasing a residual amount of an intermediate product is provided. The process comprises oxygen-oxidizing an aromatic compound having a plurality of alkyl groups (e.g., durene) in the presence of a catalyst containing a cyclic imino unit having an N—OR group (wherein R represents a hydrogen atom or a protecting group for a hydroxyl group) and a transition metal co-catalyst (e.g., a cobalt compound, a manganese compound, and a zirconium compound) under heating in a lower-temperature zone and a higher-temperature zone to produce an aromatic polycarboxylic acid in which a plurality of alkyl groups are oxidized into carboxyl groups. In an initial stage of the reaction, the reaction may be conducted in a first lower-temperature zone (a reaction temperature of 60 to 120° C.
    Type: Application
    Filed: June 10, 2009
    Publication date: March 24, 2011
    Inventors: Akihiro Shibamoto, Takahiro Iwahama
  • Publication number: 20110071313
    Abstract: A process for allowing an oxidation reaction efficiently to produce an object aromatic carboxylic acid with an efficient productivity by improving a catalyst activity even in the presence of a relatively small amount of a catalyst is provided. The process comprises oxygen-oxidizing an aromatic compound having an alkyl group and/or an alkylene group as a substrate in the presence of a catalyst containing a cyclic imino unit having an N—OR group (wherein R represents a hydrogen atom or a protecting group for a hydroxyl group) and a transition metal co-catalyst (a cobalt compound, a manganese compound, and a zirconium compound) to produce the aromatic carboxylic acid corresponding to the aromatic compound. The oxidation reaction is carried out with feeding a mixture of the catalyst and at least one member selected from the group consisting of the substrate, a reaction intermediate (e.g., a ketone and an aldehyde), and a reaction product (e.g.
    Type: Application
    Filed: May 21, 2009
    Publication date: March 24, 2011
    Inventor: Akihiro Shibamoto
  • Patent number: 7868201
    Abstract: A process for the oxidation of hydrocarbons comprises contacting the hydrocarbon with an oxygen-containing gas in the presence of a catalyst comprising a microporous solid support, preferably a zeolite, having from 8- to 12-ring open windows and comprising non-framework metal cations selected from manganese, iron, cobalt, vanadium, chromium, copper, nickel, and ruthenium, and mixtures thereof, providing that the oxygen-containing gas does not contain significant amounts of added hydrogen. The catalyst is novel and forms part of the invention. The process may be used for oxidation of alkanes, cycloalkanes, benzene and alkylbenzenes, and is suitable for use in regioselective terminal oxidation of straight chain alkanes and for selective oxidation/separation of p-dialkylbenzenes from an alkylbenzene mixture, for example, p-xylene from an isomeric mixture of xylenes.
    Type: Grant
    Filed: July 1, 2005
    Date of Patent: January 11, 2011
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
  • Publication number: 20100331569
    Abstract: Disclosed is a process for the production of an oxygen-containing organic compound by oxidizing an organic compound with molecular oxygen in a liquid phase in the presence both of a catalytic nitrogen-containing cyclic compound and a catalyst including a solid superacid and, supported thereon, a transition metal compound, in which the nitrogen-containing cyclic compound contains, as a ring constituent, a skeleton represented by following Formula (1), wherein X represents an —OR group, and wherein R represents hydrogen atom or a hydroxyl-protecting group. The process gives the oxygen-containing organic compound in a high yield and enables easy recovery and reuse of the catalyst.
    Type: Application
    Filed: February 27, 2009
    Publication date: December 30, 2010
    Inventors: Minoru Takano, Naruhisa Hirai, Yasutaka Ishii
  • Patent number: 7692036
    Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.
    Type: Grant
    Filed: June 16, 2005
    Date of Patent: April 6, 2010
    Assignee: Eastman Chemical Company
    Inventors: Alan George Wonders, Robert Lin, Lee Reynolds Partin, Marcel de Vreede, Wayne Scott Strasser
  • Publication number: 20090326265
    Abstract: The invention relates to a process for preparing an aromatic polycarboxylic acid by liquid phase oxidation of a di- or tri-substituted benzene or naphtalene compound, the process comprising a step of contacting the aromatic compound with an oxidant in the presence of a carboxylic acid solvent, a metal catalyst and a promoter in a reaction zone, wherein the promoter is an ionic liquid comprising an organic cation and a bromide or iodide anion. Advantages of this process include high conversion without severe corrosion problems otherwise associated with halogen-containing compounds as promoter. The process does not necessitate the use of special corrosion-resistant material or liners in the process equipment; thus offering savings on investment and maintenance costs and increasing plant reliability. The process of the invention is especially suited for production of terephthalic acid from p-xylene.
    Type: Application
    Filed: December 18, 2007
    Publication date: December 31, 2009
    Inventors: Syed Azahar Hashmi, Sulaiman Al-Luhaidan
  • Patent number: 7465824
    Abstract: A process is disclosed for producing at least one high purity aromatic carboxylic acid by oxidizing an aromatic feedstock with oxygen in a reaction medium comprising the aromatic feedstock, a promoter, a heavy metal catalyst, and a solvent which comprises benzoic acid and water to produce a reactor effluent wherein substantially all of the aromatic carboxylic acid produced remains in solution; and then hydrogenating the reactor effluent in the presence of a catalyst and hydrogen. This process efficiently and effectively produces high purity aromatic carboxylic acids by utilizing a common solvent for both oxidation and purification and eliminating the need for intermediate process steps and equipment.
    Type: Grant
    Filed: February 8, 2007
    Date of Patent: December 16, 2008
    Assignee: BP Corporation North America Inc.
    Inventors: Carolyn E. Schmit, David L. Sikkenga, Christopher G. Meller
  • Publication number: 20080194866
    Abstract: A process is disclosed for producing at least one high purity aromatic carboxylic acid by oxidizing an aromatic feedstock with oxygen in a reaction medium comprising the aromatic feedstock, a promoter, a heavy metal catalyst, and a solvent which comprises benzoic acid and water to produce a reactor effluent wherein substantially all of the aromatic carboxylic acid produced remains in solution; and then hydrogenating the reactor effluent in the presence of a catalyst and hydrogen. This process efficiently and effectively produces high purity aromatic carboxylic acids by utilizing a common solvent for both oxidation and purification and eliminating the need for intermediate process steps and equipment.
    Type: Application
    Filed: February 8, 2007
    Publication date: August 14, 2008
    Applicant: BP Corporation North America Inc.
    Inventors: Carolyn E. Schmit, David L. Sikkenga, Christopher G. Meller
  • Patent number: 7378544
    Abstract: The present invention relates to the liquid phase oxidation of aromatic hydrocarbons in the presence of at least one heavy metal oxidation catalyst and bromine, which is activated by at least one of anthracene or another polycyclic aromatic compound to produce aromatic carboxylic acids.
    Type: Grant
    Filed: November 3, 2004
    Date of Patent: May 27, 2008
    Assignee: BP Corporation North America Inc.
    Inventors: Wayne P. Schammel, Victor A. Adamian, Yenamandra Viswanath, Igor V. Zakharov
  • Patent number: 7371866
    Abstract: A process for catalytically oxidizing alkylaromatic compounds of the formula (I) Ar—CH2—R where Ar is an optionally substituted, aromatic or heteroaromatic 5-membered or 6-membered ring or a ring system having up to 20 carbon atoms where Ar may optionally be fused to a C1-C6-alkyl group in which up to 2 carbon atoms may be replaced by a heteroatom, and R is hydrogen, phenyl, benzyl or heteroaryl, where the phenyl, benzyl or heteroaryl radicals may also be joined to Ar by a bridge, or R together with Ar forms an optionally substituted ring system which may contain one or more optionally substituted heteroatoms, to the corresponding aromatic or heteroaromatic carboxylic acids in a solvent with ozone in the presence of a transition metal catalyst and optionally in the presence of an acid at a temperature between ?70° C. and 110° C. to the corresponding carboxylic acid.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: May 13, 2008
    Assignee: DSM Fine Chemicals Austria Nfg GmbH & Co KG
    Inventors: Walther Jary, Peter Poechlauer, Thorsten Ganglberger
  • Patent number: 7348452
    Abstract: A method for liquid phase oxidation of p-xylene with molecular oxygen to terephthalic acid that minimizes solvent loss through solvent burn and minimizes the formation of incomplete oxidation products such as 4-carboxybenzaldehyde (4-CBA). P-xylene is oxidized at a temperature in the range of 120° C. to 250° C. and in the presence of a source of molecular oxygen and a catalyst composition substantially free of zirconium atoms comprising a source of nickel (Ni) atoms, a source of manganese (Mn) atoms, and a source of bromine (Br) atoms, to form a crude reaction mixture comprising terephthalic acid and incompletely oxidized reaction products comprising 4-CBA, wherein the stoichiometric molar ratio of bromine atoms to manganese atoms is 1.5 or less, and the amount of nickel atoms is at least 500 ppm.
    Type: Grant
    Filed: April 22, 2004
    Date of Patent: March 25, 2008
    Assignee: Eastman Chemical Company
    Inventor: Gino Georges Lavoie
  • Patent number: 7342128
    Abstract: The present invention relates to a process for oxidizing a slurry composition in a post oxidation zone in the presence of added steam. More specifically, the present invention relates to a process for oxidizing a crude terephthalic acid composition in a post oxidation zone in the presence of added steam in a process for the production of a crystallized post oxidation composition.
    Type: Grant
    Filed: October 20, 2005
    Date of Patent: March 11, 2008
    Assignee: Eastman Chemical Company
    Inventors: Robert Lin, Marcel de Vreede, Johannes Wilhelmus Sluijmers, Martin De Boer, Thomas Earl Woodruff
  • Patent number: 7196215
    Abstract: Disclosed is a process for the production of terephthalic acid by a plurality of process steps including the catalyst oxidation of a dialkylbenzene compound, a second oxidation, a hydrogenation of the product of the second oxidation, and crystallization of the hydrogenation terephthalic acid using a plurality of series-connected crystallizers.
    Type: Grant
    Filed: May 31, 2002
    Date of Patent: March 27, 2007
    Assignee: Eastman Chemical Company
    Inventors: Robert Lin, Ruairi Seosamh O'Meadhra, Ronald Buford Sheppard
  • Patent number: 6759550
    Abstract: The present invention pertains to an improved method of oxidizing substituted aromatic compounds (such as p xylene) to their corresponding aromatic acids (such as terephthalic acid). The improvement involves carrying out the oxidation reaction in an aqueous medium, wherein the aqueous medium contains at least 30 percent water, preferably up to 30 percent surfactant and preferably a low molecular weight material containing a hydrophilic end group as a co-surfactant. The reaction is carried out at a pH of less than 3.0.
    Type: Grant
    Filed: November 13, 2002
    Date of Patent: July 6, 2004
    Assignee: The Dow Chemical Company
    Inventors: John Klier, Christopher J. Tucker, Thomas H. Kalantar, Kenneth A. Burdett, Daniel Patrick Green, Luciano Piras, Sergio Schena, Guo-shuh John Lee
  • Patent number: 6756509
    Abstract: A method for purifying crude 2,6-naphthalenedicarboxylic acid includes a reduction step of reducing crude 2,6-naphthalenedicarboxylic acid containing 6-formyl-2-naphthoic acid with hydrogen and a cleaning step of cleaning the reduction product with alcohol. Preferably, in the reduction step, the crude 2,6-naphthalenedicarboxylic acid and the hydrogen is brought into contact with a hydrogenation catalyst in a liquid phase, and particularly in water. The method makes the purification process less complex and makes it possible to produce high-purity 2,6-naphthalenedicarboxylic acid without damaging equipment or increasing cost.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: June 29, 2004
    Assignee: Kobe Steel, Ltd.
    Inventors: Yoshiyuki Nagase, Koji Yamamoto, Takeharu Tanaka, Maki Hamaguchi
  • Patent number: 6747171
    Abstract: A process for purifying a naphthalenic carboxylic acid comprising contacting at a temperature below about 575° F. a mixture comprising an impure naphthalenic carboxylic acid and a solvent in the presence of hydrogen gas with a noble metal on carbon catalyst. The process results in reduced amounts of organic impurities in the purified acid when compared to other purification processes.
    Type: Grant
    Filed: February 1, 2001
    Date of Patent: June 8, 2004
    Assignee: BP Corporation North America Inc.
    Inventor: Bruce I. Rosen
  • Patent number: 6717009
    Abstract: A high-purity naphthalenedicarboxylic acid is produced by a method including Steps [1] and [2]: In Step [I], a raw mixture of crude terephthalic acid and crude naphthalenedicarboxylic acid is dissolved into high-temperature high-pressure water to form a dibasic acid solution wherein the crude naphthalenedicarboxylic acid content is 0.1 to 10 mass percent of the crude terephthalic acid content, the dibasic acid solution is brought into contact with hydrogen in the presence of a catalyst. In Step [II], the resultant in the dibasic acid solution is crystallized by multiple stages while the temperature and the pressure are reduced for each stage, and acid mixtures containing enriched naphthalenedicarboxylic acid or enriched terephthalic acid are obtained by solid-liquid separation.
    Type: Grant
    Filed: October 7, 2002
    Date of Patent: April 6, 2004
    Assignee: Kabushiki Kaisha Kobe Seiko Sho (Kobe Steel, Ltd.)
    Inventors: Masahiro Motoyuki, Tomoki Uemura, Koji Yamamoto
  • Patent number: 6562997
    Abstract: Processes for the production of aromatic carboxylic acids is disclosed. The aromatic acids are produced by the liquid phase oxidation of a suitable acid precursor in a reaction medium comprising benzoic acid. According to one embodiment, the oxidation is carried out under plug-flow reaction conditions in a plug-flow reactor. The plug-flow conditions can be achieved by the use of a series of continuous stirred tank reactors. In another embodiment, the oxidation is carried out in two continuous stirred tank reactors fluidly connected in series. The preferred oxidation products are terephthalic acid, isophthalic acid, trimellitic acid, 2,6-naphthalene dicarboxylic acid, 1,5-napthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid and phthalic acid.
    Type: Grant
    Filed: January 19, 2001
    Date of Patent: May 13, 2003
    Assignee: BP Corporation North America Inc.
    Inventors: David L. Sikkenga, Alpen K. Pandya, Ian C. Zaenger, Kenneth J. Abrams, Thomas M. Bartos
  • Patent number: 6521786
    Abstract: A description is given here of a novel process for the production of monocarboxylic and polycarboxylic aromatic acids by the catalytic oxidation in homogeneous phase of aromatic compounds carrying at least one oxidizable substituent group attached directly to the carbon atom of the corresponding aromatic nucleus. The novel process according to the present invention comprises the steps of: a) catalytically oxidizing the corresponding aromatic precursors in liquid phase in the presence of gaseous oxygen; b) filtering the end product; c) recycling into the oxidation reactor at least part of the mother liquors resulting from the filtration stage, and is characterized by the fact that said steps from (a) to (c) are carried out in a closed and continuous cycle operating substantially under the same pressure and temperature conditions, preferably at 2-10 barg and 100-140° C.
    Type: Grant
    Filed: August 8, 2001
    Date of Patent: February 18, 2003
    Inventors: Franco Codignola, Antonio Moro
  • Patent number: 6355835
    Abstract: The present invention relates to a process for the preparation of benzene dicarboxylic acids by liquid phase oxidation of Xylene isomers using oxygen or air by oxidising in the presence of acetic acid as solvent, cobalt salt as catalyst and an initiator. The oxidation step is followed by flashing the said reaction mixture to remove volatile substances and cooling and filtering to get crude benzene di-carboxylic acid as a solid product and filtrate. The dicarboxylic acid solid product is recrystallised to get at least 99% pure benzene. The filtrate may be recycled.
    Type: Grant
    Filed: December 8, 1999
    Date of Patent: March 12, 2002
    Assignee: Chemintel (India) Private Limited
    Inventors: Girendra Narain Kulsrestha, Mahendra Pratap Saxena, Ashok Kumar Gupta, Satish Kumar Sharma, Dinesh Prasad Bangwal, Hari Bhagwan Goyal, Rameshwar Prasad, Sanjib Mall, Prakash D. Patel
  • Publication number: 20020002303
    Abstract: A process for purifying a naphthalenic carboxylic acid comprising contacting at a temperature below about 575° F. a mixture comprising an impure naphthalenic carboxylic acid and a solvent in the presence of hydrogen gas with a noble metal on carbon catalyst. The process results in reduced amounts of organic impurities in the purified acid when compared to other purification processes.
    Type: Application
    Filed: February 1, 2001
    Publication date: January 3, 2002
    Inventor: Bruce I. Rosen
  • Publication number: 20010041811
    Abstract: Processes for the production of aromatic carboxylic acids is disclosed. The aromatic acids are produced by the liquid phase oxidation of a suitable acid precursor in a reaction medium comprising benzoic acid. According to one embodiment, the oxidation is carried out under plug-flow reaction conditions in a plug-flow reactor. The plug-flow conditions can be achieved by the use of a series of continuous stirred tank reactors. In another embodiment, the oxidation is carried out in two continuous stirred tank reactors fluidly connected in series. The preferred oxidation products are terephthalic acid, isophthalic acid, trimellitic acid, 2,6-naphthalene dicarboxylic acid, 1,5-napthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid and phthalic acid.
    Type: Application
    Filed: January 19, 2001
    Publication date: November 15, 2001
    Inventors: David L. Sikkenga, Alpen K. Pandya, Ian C. Zaenger, Kenneth J. Abrams, Thomas M. Bartos
  • Publication number: 20010016667
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound: 1
    Type: Application
    Filed: March 19, 2001
    Publication date: August 23, 2001
    Applicant: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 5980801
    Abstract: Methods for oxidizing a hydrocarbon to an intermediate oxidation product by utilizing an activated initiator. The initiator is activated by partially oxidizing a first mixture of the initiator and a hydrocarbon, which mixture contains a rather large amount of initiator. The first mixture may even be just initiator. The first mixture, after the partial oxidation, is mixed with a second mixture containing hydrocarbon and a smaller amount of initiator. The second mixture may even contain no initiator at all. The oxidation is continued to a desired degree. Preferably, at least one of the two mixtures, and even more preferably both reaction mixtures contain an oxidation catalyst and an acidic solvent.
    Type: Grant
    Filed: June 25, 1998
    Date of Patent: November 9, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
  • Patent number: 5824819
    Abstract: Methods for oxidizing a hydrocarbon to an intermediate oxidation product by utilizing an activated initiator. The initiator is activated by partially oxidizing a first mixture of the initiator and a hydrocarbon, which mixture contains a rather large amount of initiator. The first mixture may even be just initiator. The first mixture, after the partial oxidation, is mixed with a second mixture containing hydrocarbon and a smaller amount of initiator. The second mixture may even contain no initiator at all. The oxidation is continued to a desired degree. Preferably, at least one of the two mixtures, and even more preferably both reaction mixtures contain an oxidation catalyst and an acidic solvent.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: October 20, 1998
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
  • Patent number: 5523473
    Abstract: A method of producing naphthalenedicarboxylic acids by the oxidation of dialkyl-substituted naphthalene with a gas containing molecular oxygen in an organic solvent and in the presence of a catalyst comprising copper and bromine, or a catalyst comprising copper, bromine and at least one kind of element/compound selected from the group of consisting of amine compounds and heavy metallic elements which are vanadium, manganese, iron, nickel, palladium and cerium. And a method of producing diaryldicarboxylic acids by the oxidation of dialkyl-substituted diaryl compounds with a gas containing molecular oxygen in an organic solvent and in the presence of the same catalyst. These methods permit high yields of naphthalenedicarboxylic acids of high purity and of diaryldicarboxylic acids of high purity with the use of small amounts of catalyst.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: June 4, 1996
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Noboru Saitou, Koichi Hirota, Ren Hasebe, Norimasa Okuda, Ikuyo Katsumi
  • Patent number: 5453538
    Abstract: A process for the manufacture of aromatic dicarboxylic acids is disclosed using a low bromine to metals ratio facilitated by the use of cerium along with the cobalt and manganese catalyst. Aromatic dicarboxylic acids such as terephthalic acid are useful in the manufacture of fiber, films, bottles and molded products.
    Type: Grant
    Filed: February 14, 1994
    Date of Patent: September 26, 1995
    Assignee: Amoco Corporation
    Inventors: Jeffrey L. Broeker, Walter Partenheimer, Bruce I. Rosen
  • Patent number: 5420344
    Abstract: A process for producing highly pure terephthalic acid, which comprises heating and dissolving crude terephthalic acid in water, and purifying it by contacting the aqueous solution with hydrogen at a temperature of from 260.degree. to 320.degree. C. in the presence of a platinum group metal catalyst, wherein the purification is initiated within three minutes after the aqueous solution under heating reaches a temperature of 250.degree. C.
    Type: Grant
    Filed: October 13, 1993
    Date of Patent: May 30, 1995
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yoshiaki Izumisawa, Tsukasa Kawahara, Yoshiyuki Sumi, Takehiko Baba, Yoshio Ishinaga, Katsuhiko Fukui, Hironori Ohgi
  • 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: 5288908
    Abstract: Compounds of the formula ##STR1## in which X represents hydrogen, --NO.sub.2 or --NH.sub.2 and Y represents --CH.sub.3, --COOH, --CONH.sub.2, --NH.sub.2 or --N.dbd.N--Z, in which the group --Z is ##STR2## with the proviso that if Y represents the group --N.dbd.N--Z, X is only --NO.sub.2, and if Y represents the group --CH.sub.3, X is only hydrogen, are described. A compound of the formula ##STR3## the preparation of which in a multi-stage process, in which the compounds of the general formula (I) are also obtained, is described, is preferred.The resulting 3,4'-diamino compound is suitable for the preparation of polycondensates and shaped articles, films and fibers of high heat resistance.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: February 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
  • Patent number: 5274126
    Abstract: A compound of the formula ##STR1## and the dianhydride thereof are prepared by air oxidation in the presence of a catalyst mixture composed of at least 2 heavy metal salts and also bromine in an acid organic medium. The compounds can be employed for the preparation of partially fluorinated polycondensates, such as polyimides, polycarboxamides, esters of polyamidecarboxylic acids, polyamides and imide-oligomers.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: December 28, 1993
    Assignee: Hoechst AG
    Inventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
  • Patent number: 5256817
    Abstract: A method for purifying a naphthalenedicarboxylic acid comprising contacting an impure naphthalenedicarboxylic acid with hydrogen in the presence of a hydrogenation catalyst and a solvent comprising a low molecular weight carboxylic acid, at a temperature of at least about 500.degree. F., and a pressure sufficient to maintain the solvent at least partially in the liquid phase and thereafter recovering purified naphthalenedicarboxylic acid.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: October 26, 1993
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Stephen V. Hoover
  • Patent number: 5250724
    Abstract: A very selective process for the catalytic air oxidation of pseudocumene to trimellitic acid. Manganese, cobalt, cerium and titanium in the presence of bromine are used as the catalyst.
    Type: Grant
    Filed: May 12, 1992
    Date of Patent: October 5, 1993
    Assignee: Alusuisse Italia S.p.A.
    Inventors: Carlo Fumagalli, Lorenzo Capitanio, Giancarlo Stefani
  • 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: 5183933
    Abstract: Provided is a continuous process for producing 2,6-naphthalenedicarboxylic acid by the liquid phase oxidation of 2,6-dimethylnaphthalene comprising continuously adding to a reaction zone the oxidation reaction components comprising 2,6-dimethylnaphthalene, a source of molecular oxygen, a solvent comprising an aliphatic monocarboxylic acid, and a catalyst comprising cobalt, manganese and bromine components, wherein the atom ratio of manganese to cobalt is about 5:1 to about 0.3:1, the total of cobalt and manganese is at least about 0.40 weight percent based on the weight of solvent, and maintaining the contents of the reaction zone at a temperature of about 370.degree. F. to about 420.degree. F. and at a pressure sufficient to maintain at least a portion of the monocarboxylic acid in the liquid phase thereby oxidizing the 2,6-dimethylnaphthalene to 2,6-naphthalenedicarboxylic acid.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: February 2, 1993
    Assignee: Amoco Corporation
    Inventors: Jon J. Harper, George E. Kuhlmann, Keith D. Larson, Rosemary F. McMahon, Paul A. Sanchez
  • Patent number: 5175352
    Abstract: A process for preparing 2,6-naphthalenedicarboxylic acid comprising oxidation reaction of 2,6-diisopropylnaphthalene or an oxidation product thereof with molecular oxygen in a solvent containing an aliphatic carboxylic acid in the presence of a catalyst comprising cobalt and manganese as heavy metals and a bromine compound is disclosed, in which said oxidation reaction is carried out in the presence of at least one nitrogen-containing compound selected from the group consisting of a pyridine compound, ammonia, a carboxylic acid ammonium salt, urea, a urea derivative, an amine, and a carboxylic acid amide. 2,6-Naphthalenedicarboxylic acid can be obtained at higher purity and in increased yield.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: December 29, 1992
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Hiroshi Iwane, Takahiro Sugawara
  • Patent number: 5171881
    Abstract: It is a process for producing trimellitic acid (trimellitic acid, 1, 2, 4-tricarboxylic acid) by oxidizing pseudocumene with a molecular oxygen containing gas. More particularly, pseudocumene is oxidized into trimellitic acid by introducing a molecular oxygen containing gas in an acetic acid solvent in the presence of oxidizing catalysts, wherein the oxidization reactions in two different stages which have different ranges of temperature and different compositions of catalyst, respectively.
    Type: Grant
    Filed: November 29, 1990
    Date of Patent: December 15, 1992
    Assignee: Yukong Limited
    Inventors: Sang H. Park, Jae S. Go, Jung W. Sim, Chun G. Kim
  • Patent number: 5144066
    Abstract: A method of producing naphthalenedicarboxylic acids by the oxidation of dialkyl-substituted naphthalene with a gas containing molecular oxygen under liquid phase conditions in an organic solvent and in the presence of a catalyst comprising copper and bromine, or a catalyst comprising copper, bromine and at least one kind of element/compound selected from the group of consisting of amine compounds and heavy metallic elements which are vanadium, manganese, iron, cobalt, nickel, palladium and cerium. And a method of producing diaryldicarboxylic acids by the oxidation of dialkyl-substituted diaryl compounds with a gas containing molecular oxygen in an organic solvent and in the presence of the same catalyst. These methods permit high yields of naphthalenedicarboxylic acids of high purity and of diaryldicarboxylic acids of high purity with the use of small amounts of catalyst.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: September 1, 1992
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Noboru Saitou, Koichi Hirota, Ren Hasebe, Norimasa Okuda, Ikuyo Katsumi