Initiator Or Promoter Used With Catalyst Patents (Class 562/417)
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Patent number: 10676420Abstract: 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: GrantFiled: October 17, 2016Date of Patent: June 9, 2020Assignee: SABIC GLOBAL TECHNOLOGIES B.V.Inventors: Syed Azhar Hashmi, Labeeb A. Chaudhary, Nedumbamana Sankaran
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Patent number: 9000214Abstract: 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: GrantFiled: June 6, 2013Date of Patent: April 7, 2015Assignee: UOP LLCInventors: Susie C. Martins, Kaitlin DeSalvo, Alakananda Bhattacharyya
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Publication number: 20140100386Abstract: 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: ApplicationFiled: December 12, 2013Publication date: April 10, 2014Applicant: UOP LLCInventor: Alakananda Bhattacharyya
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Patent number: 8624055Abstract: 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: GrantFiled: May 1, 2008Date of Patent: January 7, 2014Assignee: 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
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Patent number: 8501986Abstract: 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: GrantFiled: February 10, 2010Date of Patent: August 6, 2013Assignee: Grupo Petrotemex, S.A. de C.V.Inventors: Alan George Wonders, Robert Lin, Lee Reynolds Partin, Marcel de Vreede, Wayne Scott Strasser
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Patent number: 8410308Abstract: 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: GrantFiled: February 27, 2009Date of Patent: April 2, 2013Assignee: Daicel Chemical Industries, Ltd.Inventors: Minoru Takano, Naruhisa Hirai, Yasutaka Ishii
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Patent number: 8321082Abstract: 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: GrantFiled: September 13, 2011Date of Patent: November 27, 2012Assignee: Toyota Jidosha Kabushiki KaishaInventor: Yasushi Ando
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Patent number: 8178716Abstract: 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: GrantFiled: May 2, 2007Date of Patent: May 15, 2012Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.Inventors: Fumiya Zaima, Nirou Hoshishima
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Patent number: 8168819Abstract: 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: GrantFiled: April 4, 2007Date of Patent: May 1, 2012Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Junya Nishiuchi
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Patent number: 8163954Abstract: 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: GrantFiled: May 4, 2007Date of Patent: April 24, 2012Assignee: 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
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Patent number: 8080685Abstract: 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: GrantFiled: June 12, 2008Date of Patent: December 20, 2011Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8053597Abstract: 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: GrantFiled: June 26, 2009Date of Patent: November 8, 2011Assignee: Grupo Petrotemex, S.A. DE C.V.Inventors: Philip Edward Gibson, Kenny Randolph Parker, Ronald Buford Sheppard
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Publication number: 20110071314Abstract: 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: ApplicationFiled: June 10, 2009Publication date: March 24, 2011Inventors: Akihiro Shibamoto, Takahiro Iwahama
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Publication number: 20110071313Abstract: 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: ApplicationFiled: May 21, 2009Publication date: March 24, 2011Inventor: Akihiro Shibamoto
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Patent number: 7868201Abstract: 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: GrantFiled: July 1, 2005Date of Patent: January 11, 2011Assignee: ExxonMobil Research and Engineering CompanyInventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
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Publication number: 20100331569Abstract: 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: ApplicationFiled: February 27, 2009Publication date: December 30, 2010Inventors: Minoru Takano, Naruhisa Hirai, Yasutaka Ishii
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Patent number: 7692036Abstract: 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: GrantFiled: June 16, 2005Date of Patent: April 6, 2010Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Robert Lin, Lee Reynolds Partin, Marcel de Vreede, Wayne Scott Strasser
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Publication number: 20090326265Abstract: 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: ApplicationFiled: December 18, 2007Publication date: December 31, 2009Inventors: Syed Azahar Hashmi, Sulaiman Al-Luhaidan
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Patent number: 7465824Abstract: 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: GrantFiled: February 8, 2007Date of Patent: December 16, 2008Assignee: BP Corporation North America Inc.Inventors: Carolyn E. Schmit, David L. Sikkenga, Christopher G. Meller
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Publication number: 20080194866Abstract: 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: ApplicationFiled: February 8, 2007Publication date: August 14, 2008Applicant: BP Corporation North America Inc.Inventors: Carolyn E. Schmit, David L. Sikkenga, Christopher G. Meller
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Patent number: 7378544Abstract: 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: GrantFiled: November 3, 2004Date of Patent: May 27, 2008Assignee: BP Corporation North America Inc.Inventors: Wayne P. Schammel, Victor A. Adamian, Yenamandra Viswanath, Igor V. Zakharov
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Patent number: 7371866Abstract: 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: GrantFiled: May 15, 2003Date of Patent: May 13, 2008Assignee: DSM Fine Chemicals Austria Nfg GmbH & Co KGInventors: Walther Jary, Peter Poechlauer, Thorsten Ganglberger
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Patent number: 7348452Abstract: 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: GrantFiled: April 22, 2004Date of Patent: March 25, 2008Assignee: Eastman Chemical CompanyInventor: Gino Georges Lavoie
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Patent number: 7342128Abstract: 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: GrantFiled: October 20, 2005Date of Patent: March 11, 2008Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede, Johannes Wilhelmus Sluijmers, Martin De Boer, Thomas Earl Woodruff
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Patent number: 7196215Abstract: 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: GrantFiled: May 31, 2002Date of Patent: March 27, 2007Assignee: Eastman Chemical CompanyInventors: Robert Lin, Ruairi Seosamh O'Meadhra, Ronald Buford Sheppard
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Patent number: 6759550Abstract: 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: GrantFiled: November 13, 2002Date of Patent: July 6, 2004Assignee: The Dow Chemical CompanyInventors: John Klier, Christopher J. Tucker, Thomas H. Kalantar, Kenneth A. Burdett, Daniel Patrick Green, Luciano Piras, Sergio Schena, Guo-shuh John Lee
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Patent number: 6756509Abstract: 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: GrantFiled: July 12, 2002Date of Patent: June 29, 2004Assignee: Kobe Steel, Ltd.Inventors: Yoshiyuki Nagase, Koji Yamamoto, Takeharu Tanaka, Maki Hamaguchi
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Patent number: 6747171Abstract: 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: GrantFiled: February 1, 2001Date of Patent: June 8, 2004Assignee: BP Corporation North America Inc.Inventor: Bruce I. Rosen
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Patent number: 6717009Abstract: 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: GrantFiled: October 7, 2002Date of Patent: April 6, 2004Assignee: Kabushiki Kaisha Kobe Seiko Sho (Kobe Steel, Ltd.)Inventors: Masahiro Motoyuki, Tomoki Uemura, Koji Yamamoto
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Patent number: 6562997Abstract: 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: GrantFiled: January 19, 2001Date of Patent: May 13, 2003Assignee: BP Corporation North America Inc.Inventors: David L. Sikkenga, Alpen K. Pandya, Ian C. Zaenger, Kenneth J. Abrams, Thomas M. Bartos
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Patent number: 6521786Abstract: 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: GrantFiled: August 8, 2001Date of Patent: February 18, 2003Inventors: Franco Codignola, Antonio Moro
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Patent number: 6355835Abstract: 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: GrantFiled: December 8, 1999Date of Patent: March 12, 2002Assignee: Chemintel (India) Private LimitedInventors: 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
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Publication number: 20020002303Abstract: 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: ApplicationFiled: February 1, 2001Publication date: January 3, 2002Inventor: Bruce I. Rosen
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Publication number: 20010041811Abstract: 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: ApplicationFiled: January 19, 2001Publication date: November 15, 2001Inventors: David L. Sikkenga, Alpen K. Pandya, Ian C. Zaenger, Kenneth J. Abrams, Thomas M. Bartos
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Publication number: 20010016667Abstract: 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: 1Type: ApplicationFiled: March 19, 2001Publication date: August 23, 2001Applicant: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Patent number: 5980801Abstract: 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: GrantFiled: June 25, 1998Date of Patent: November 9, 1999Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
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Patent number: 5824819Abstract: 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: GrantFiled: May 21, 1997Date of Patent: October 20, 1998Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster, Ader M. Rostami
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Patent number: 5523473Abstract: 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: GrantFiled: May 25, 1995Date of Patent: June 4, 1996Assignee: Nippon Shokubai Co., Ltd.Inventors: Noboru Saitou, Koichi Hirota, Ren Hasebe, Norimasa Okuda, Ikuyo Katsumi
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Patent number: 5453538Abstract: 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: GrantFiled: February 14, 1994Date of Patent: September 26, 1995Assignee: Amoco CorporationInventors: Jeffrey L. Broeker, Walter Partenheimer, Bruce I. Rosen
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Patent number: 5420344Abstract: 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: GrantFiled: October 13, 1993Date of Patent: May 30, 1995Assignee: Mitsubishi Chemical CorporationInventors: Yoshiaki Izumisawa, Tsukasa Kawahara, Yoshiyuki Sumi, Takehiko Baba, Yoshio Ishinaga, Katsuhiko Fukui, Hironori Ohgi
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Patent number: 5334754Abstract: 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: GrantFiled: August 14, 1992Date of Patent: August 2, 1994Assignee: Eastman Chemical CompanyInventors: Charles E. Sumner, Jr., Bruce L. Gustafson, Ernest W. Arnold, III, Eric J. Fugate, Dewey W. Fuller, Jr.
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Patent number: 5288908Abstract: 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: GrantFiled: July 19, 1993Date of Patent: February 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
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Patent number: 5274126Abstract: 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: GrantFiled: June 5, 1992Date of Patent: December 28, 1993Assignee: Hoechst AGInventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
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Patent number: 5256817Abstract: 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: GrantFiled: June 18, 1992Date of Patent: October 26, 1993Assignee: Amoco CorporationInventors: David L. Sikkenga, Stephen V. Hoover
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Patent number: 5250724Abstract: 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: GrantFiled: May 12, 1992Date of Patent: October 5, 1993Assignee: Alusuisse Italia S.p.A.Inventors: Carlo Fumagalli, Lorenzo Capitanio, Giancarlo Stefani
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Patent number: 5202469Abstract: 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: GrantFiled: June 20, 1991Date of Patent: April 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
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Patent number: 5183933Abstract: 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: GrantFiled: October 15, 1991Date of Patent: February 2, 1993Assignee: Amoco CorporationInventors: Jon J. Harper, George E. Kuhlmann, Keith D. Larson, Rosemary F. McMahon, Paul A. Sanchez
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Patent number: 5175352Abstract: 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: GrantFiled: January 6, 1992Date of Patent: December 29, 1992Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara
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Patent number: 5171881Abstract: 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: GrantFiled: November 29, 1990Date of Patent: December 15, 1992Assignee: Yukong LimitedInventors: Sang H. Park, Jae S. Go, Jung W. Sim, Chun G. Kim
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Patent number: 5144066Abstract: 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: GrantFiled: June 25, 1991Date of Patent: September 1, 1992Assignee: Nippon Shokubai Co., Ltd.Inventors: Noboru Saitou, Koichi Hirota, Ren Hasebe, Norimasa Okuda, Ikuyo Katsumi