Of Aromatic Compound Patents (Class 562/408)
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Patent number: 12138687Abstract: A method of forming an article comprises forming a feed material around one or more shapeholders and sintering the feed material and the one or more shapeholders to form a sintered article comprising the one or more shapeholders in a base material. The sintered article is exposed to a solvent to remove the one or more shapeholders from the base material. Additional methods are disclosed, as well as articles including one or more microchannels exhibiting a diameter of from about 5 ?m to about 10 mm.Type: GrantFiled: October 13, 2023Date of Patent: November 12, 2024Assignee: Battelle Energy Alliance, LLCInventors: Donna P. Guillen, Robert V. Fox, Dennis S. Tucker, Troy B. Holland
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Patent number: 11008226Abstract: Systems, apparatuses, and methods for cleaning brine solution are provided. In particular, one or more embodiments comprise a brine cleaning system that includes a brine cooker, a brine filter, and a brine storage unit. The brine cooker heats a dirty brine solution to separate the dirty brine solution into a liquid portion and a solids portion. The brine filter is coupled to the brine cooker to receive the liquid portion and the solids portion from the brine cooker and then substantially remove the solids portion. The brine storage unit is coupled to the brine filter to accumulate the liquid portion once the solids portion have been substantially removed by the brine filter. This allows for more efficient and environmentally friendly use of brine solution in the curing of animal.Type: GrantFiled: October 4, 2019Date of Patent: May 18, 2021Assignee: National Beef Packing Company, LLCInventor: Donald Joseph Determann
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Patent number: 10479690Abstract: A process for producing an integrated layer (10 nm to 500 ?m) of highly oriented halogenated graphene sheets, comprising: (a) preparing a graphene oxide (GO) dispersion having GO sheets dispersed in a fluid medium; (b) dispensing and depositing a layer of GO dispersion onto a surface of a supporting substrate under a shear stress condition that induces orientation of GO sheets to form a wet layer of GO on the supporting substrate; (c) introducing a halogenating agent into the wet layer of graphene oxide and effecting a chemical reaction between the halogenating agent and GO sheets to form a wet layer of halogenated graphene, C6ZxOy, wherein Z is a halogen element selected from F, Cl, Br, I, or a combination thereof, x=0.01 to 6.0, y=0 to 5.0, and x+y?6.0; and (d) removing the fluid medium.Type: GrantFiled: September 15, 2017Date of Patent: November 19, 2019Assignee: Global Graphene Group, Inc.Inventors: Aruna Zhamu, Bor Z. Jang
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Patent number: 10414712Abstract: Processes for manufacturing a purified aromatic carboxylic acid include oxidizing a substituted aromatic compound in a reaction zone to form a crude aromatic carboxylic acid and a gaseous stream; heating the crude aromatic carboxylic acid in a pre-heating zone, contacting the crude aromatic carboxylic acid with hydrogen in the presence of a catalyst in a hydrogenation reactor to form a purified aromatic carboxylic acid, crystallizing the purified aromatic carboxylic acid in a crystallization zone to form a slurry stream comprising solid purified aromatic carboxylic acid and a vapor stream. At least a portion of the vapor stream is directed to the pre-heating zone and at least a portion of the vapor stream from the pre-heating zone is vented to the off-gas treatment zone in order to achieve energy savings.Type: GrantFiled: November 28, 2017Date of Patent: September 17, 2019Assignee: BP Corporation North America Inc.Inventors: Thomas Bartos, Kathryn Buckalew
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Patent number: 9809459Abstract: A process for producing an integrated layer (10 nm to 500 ?m) of highly oriented halogenated graphene sheets, comprising: (a) preparing a graphene oxide (GO) dispersion having GO sheets dispersed in a fluid medium; (b) dispensing and depositing a layer of GO dispersion onto a surface of a supporting substrate under a shear stress condition that induces orientation of GO sheets to form a wet layer of GO on the supporting substrate; (c) introducing a halogenating agent into the wet layer of graphene oxide and effecting a chemical reaction between the halogenating agent and GO sheets to form a wet layer of halogenated graphene, C6ZxOy, wherein Z is a halogen element selected from F, Cl, Br, I, or a combination thereof, x=0.01 to 6.0, y=0 to 5.0, and x+y?6.0; and (d) removing the fluid medium.Type: GrantFiled: September 23, 2015Date of Patent: November 7, 2017Assignee: Nanotek Instruments, Inc.Inventors: Aruna Zhamu, Bor Z Jang
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Patent number: 9024060Abstract: 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: GrantFiled: December 26, 2013Date of Patent: May 5, 2015Assignee: Saudi Basic Industries CorporationInventors: Corrado Berti, Enrico Binassi, Martino Colonna, Maurizio Fiorini, Ganesh Kannan, Sreepadaraj Karanam, Marzia Mazzacurati, Ihab Odeh
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Patent number: 8968686Abstract: Disclosed are process and apparatus for vertical splitting of the oxygen supply to a post-oxidation reactor. Further disclosed are process and apparatus for supplying reaction medium to a post-oxidation reactor at a mid-level inlet. Such apparatus and process can assist in reducing oxygen pinch throughout the post-oxidation reactor.Type: GrantFiled: December 1, 2010Date of Patent: March 3, 2015Assignee: Grupo Petrotemex, S.A. de C.V.Inventors: Ashfaq Shaikh, Alan George Wonders
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Patent number: 8957247Abstract: In pretreating a pyridine ring-containing chelate resin which is used in the step for adsorption and collection of a heavy metal ion and a bromide ion derived from a catalyst from the oxidation reaction mother liquid in the process of producing an aromatic carboxylic acid, there may occur phenomena such as swelling of the resin, heat generation of the resin, and air bubbles generation, thereby causing fracture and deterioration of the resin. As a first treatment, Br? conversion, under a certain condition, of a pyridine ring-containing chelate resin with an aqueous solution of hydrobromic acid is performed, and then as a second treatment, replacement with acetic acid solvent is performed, thereby making it possible to prevent fracture and deterioration of the resin.Type: GrantFiled: February 18, 2011Date of Patent: February 17, 2015Assignees: Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.Inventors: Fumiya Zaima, Hideaki Fujita
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Patent number: 8946472Abstract: 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: GrantFiled: December 31, 2008Date of Patent: February 3, 2015Assignee: Sabic Innovative Plastics IP B.V.Inventors: Corrado Berti, Enrico Binassi, Martino Colonna, Maurizio Fiorini, Ganesh Kannan, Sreepadaraj Karanam, Marzia Mazzacurati, Ihab Odeh
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Patent number: 8940255Abstract: Disclosed are process and apparatus for vertical splitting of the oxygen supply to a post-oxidation reactor. Further disclosed are process and apparatus for supplying reaction medium to a post-oxidation reactor at a mid-level inlet. Such apparatus and process can assist in reducing oxygen pinch throughout the post-oxidation reactor.Type: GrantFiled: December 1, 2010Date of Patent: January 27, 2015Assignee: Grupo Petrotemex, S.A. de C.V.Inventors: Ashfaq Shaikh, Alan George Wonders
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Patent number: 8936767Abstract: Disclosed are process and apparatus for vertical splitting of the oxygen supply to a post-oxidation reactor. Further disclosed are process and apparatus for supplying reaction medium to a post-oxidation reactor at a mid-level inlet. Such apparatus and process can assist in reducing oxygen pinch throughout the post-oxidation reactor.Type: GrantFiled: December 1, 2010Date of Patent: January 20, 2015Assignee: Grupo Petrotemex. S.A. DE C.V.Inventors: Ashfaq Shaikh, Alan George Wonders, David Lange
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Patent number: 8933265Abstract: A process and a mixture for oxidizing an alkyl-aromatic compound comprises forming a mixture comprising the alkyl-aromatic compound, a solvent, a bromine source, a catalyst, and ammonium acetate; and contacting the mixture with an oxidizing agent at oxidizing conditions to produce an oxidation product comprising at least one of an aromatic aldehyde, an aromatic alcohol, an aromatic ketone, and an aromatic carboxylic acid. The solvent comprises a carboxylic acid having from 1 to 7 carbon atoms; and the catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium.Type: GrantFiled: June 8, 2011Date of Patent: January 13, 2015Assignee: UOP LLCInventors: Alakananda Bhattacharyya, Joel T. Walenga
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Patent number: 8865932Abstract: Provided are a fluorinated graphene oxide and a preparation method thereof. In the fluorinated graphene oxide, the mass percent of fluorine is 0.5%<F %<40%; the mass percent of carbon is 50%<C %<80%, and the mass percent of oxygen is 0.5%<O %<30%. The preparation method comprises the following steps: providing graphite; preparing graphene oxide by using the graphite; and subjecting the graphene oxide to reacting with a mixed gas of N2 and F2 at 20˜200° C. for 0.5˜24 h, to prepare the fluorinated graphene oxide. The preparation method is simple, has fewer steps, and has better prospect of application.Type: GrantFiled: December 22, 2010Date of Patent: October 21, 2014Assignee: Ocean's King Lighting Science & Technology Co., Ltd.Inventors: Mingjie Zhou, Daxi Liu, Yaobing Wang
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Patent number: 8710260Abstract: A process for preparing an aromatic carboxylic acid having a heteroatom containing substituent is provided that includes reaction in a vessel of an aromatic precursor having an aromatic core with at least one heteroatom containing substituent and at least one hydrogen extending from the core, with a haloacetonitrile under reaction conditions to form an aromatic acetonitrile with an acetonitrile moiety. The aromatic acetonitrile is exposed to an oxidizing agent under conditions to convert the acetonitrile moiety to a carboxylic acid group to prepare the aromatic carboxylic acid having the heteroatom containing substituent.Type: GrantFiled: March 8, 2010Date of Patent: April 29, 2014Assignee: PerkinElmer Health Sciences, Inc.Inventors: Crist N. Filer, Terence P. Kelly, Chrisopher Wright
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Publication number: 20140018569Abstract: By selectively hydrogenating a feedstock containing two or more hydrocarbons selected from the group consisting of tricyclic aromatic hydrocarbons having an anthracene skeleton and tricyclic aromatic hydrocarbons having a phenanthrene skeleton to 1,2,3,4,5,6,7,8-octahydro bodies using, as a hydrogenation catalyst, a catalyst containing two or more active metals selected from the group consisting of nickel, molybdenum, cobalt, and tungsten and then, by oxidizing the 1,2,3,4,5,6,7,8-octahydro body using a metal oxide, a benzenetetracarboxylic acid can be efficiently manufactured.Type: ApplicationFiled: March 21, 2012Publication date: January 16, 2014Inventors: Ryoji Ida, Shinichiro Yanagawa
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Publication number: 20130289303Abstract: Provided is a simple filtering operation method capable of conducting a filtering operation without clogging in a ceramic filter for a long period of time, in the operation of filtering fine crystals of an aromatic carboxylic acid in an oxidation reaction mother liquor obtained in a process of an aromatic carboxylic acid production by a cross-flow filtration using the ceramic filter. The present invention can be accomplished by conducting an operation for filtering the fine crystals and a back washing operation with a filtrate while maintaining a flowing circulation operation of the oxidation reaction mother liquor under predetermined conditions.Type: ApplicationFiled: October 25, 2011Publication date: October 31, 2013Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventor: Fumiya Zaima
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Publication number: 20130237723Abstract: Provided are a fluorinated graphene oxide and a preparation method thereof. In the fluorinated graphene oxide, the mass percent of fluorine is 0.5%<F %<40%; the mass percent of carbon is 50%<C %<80%, and the mass percent of oxygen is 0.5%<0%<30%. The preparation method comprises the following steps: providing graphite; preparing graphene oxide by using the graphite; and subjecting the graphene oxide to reacting with a mixed gas of N2 and F2 at 20˜200° C. for 0.5˜24 h, to prepare the fluorinated graphene oxide. The preparation method is simple, has fewer steps, and has better prospect of application.Type: ApplicationFiled: December 22, 2010Publication date: September 12, 2013Inventors: Mingjie Zhou, Daxi Liu, Yaobing Wang
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Patent number: 8524922Abstract: A process for recovering solid reaction products during partial oxidation of hydrocarbons in a liquid solvent as a reaction medium by multi-stage evaporative crystallization includes determining a final temperature of the multi-stage evaporative crystallization based on a melting point of the solvent. The pressure and temperature of the solvent is reduced in steps via successive crystallization stages until the final temperature is reached. Each of the crystallization stages includes a compressor configured to perform the reducing of the pressure and to withdraw vapors formed. The vapors from the compressor of a lower expansion pressure crystallization stage are introduced into a vapor discharge conduit of a next successive higher expansion pressure crystallization stage upstream of the compressor of the higher expansion pressure crystallization stage.Type: GrantFiled: August 13, 2009Date of Patent: September 3, 2013Assignee: Lurgi GmbHInventors: Thomas Gutermuth, Robert Szabo
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Publication number: 20130190528Abstract: A one-pot method for the oxidative cleavage of unsaturated carbon-carbon bonds to provide a carboxylic acid or a ketone-containing compound is disclosed. The method comprises contacting an alkene or an alkyne with hydrogen peroxide and a manganese transition metal catalyst having a ligand of formula (I): wherein: and p is 3.Type: ApplicationFiled: July 21, 2011Publication date: July 25, 2013Applicant: CATEXEL LIMITEDInventors: Ronald Hage, Johannes Wietse De Boer, Pattama Saisaha
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Publication number: 20130172608Abstract: Processes for oxidizing an alkyl-aromatic compound are described. The processes include contacting an alkyl-aromatic compound, a solvent, a bromine source, a catalyst, and an oxidizing agent to produce a product comprising at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid. The composition of the solvent is controlled to reduce the impurities in the product.Type: ApplicationFiled: December 29, 2011Publication date: July 4, 2013Applicant: UOP LLCInventors: Alakananda Bhattacharyya, Joel T. Walenga
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Publication number: 20130045156Abstract: A first precipitate is formed by mixing graphite and an oxidizer containing an alkali metal salt in a solution. Next, a second precipitate is formed by ionizing the oxidizer which is included in the first precipitate, with an acid solution, and removing the oxidizer from the first precipitate. Then, a dispersion liquid in which graphene oxide is dispersed is prepared by mixing the second precipitate and water to form a mixed solution and then applying ultrasonic waves to the mixed solution or mechanically stirring the mixed solution, so that the graphene oxide is separated from graphite oxide that is the graphite which is included in the second precipitate and oxidized. Next, graphene oxide salt is formed by mixing the dispersion liquid, a basic solution, and an organic solvent and reacting the graphene oxide included in the dispersion liquid and a base included in the basic solution to each other.Type: ApplicationFiled: August 9, 2012Publication date: February 21, 2013Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.Inventors: Kuniharu Nomoto, Nobuhiro Inoue, Mikio Yukawa, Tatsuya Ikenuma
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Patent number: 8236921Abstract: The invention provides improved energy content in and shaft power recovery from off-gas from xylene oxidation reactions while at the same time minimizing wastewater treatment cost. More shaft power is produced using off-gas than is required to drive the main air compressor, even with preferred, relatively low oxidation temperatures. Simultaneously, an amount of wastewater greater than byproduct water from oxidation of xylene is kept in vapor form and treated along with off-gas pollutants in a self-sustaining (self-fueling) gas-phase thermal oxidative destruction unit. Optionally, off-gas is combined from multiple xylene oxidation reactors, comprising primary and/or secondary oxidation reactors and forming TPA and/or IPA.Type: GrantFiled: March 30, 2012Date of Patent: August 7, 2012Assignee: Eastman Chemical CompanyInventors: Raymond Elbert Fogle, III, Ronald Buford Sheppard, Timothy Alan Upshaw, Alan George Wonders
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Publication number: 20120183770Abstract: The present invention relates to the exfoliation and dispersion of carbon nanotubes resulting in high aspect ratio, surface-modified carbon nanotubes that are readily dispersed in various media. A method is disclosed for their production in high yield. Further modifications by surface active or modifying agents are also disclosed. Application of the carbon nanotubes of this invention as composites with materials such as elastomers, thermosets and thermoplastics are also described.Type: ApplicationFiled: June 20, 2011Publication date: July 19, 2012Inventors: Clive P. Bosnyak, Kurt W. Swogger
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Patent number: 8188309Abstract: The present invention relates to a process for making terephthalic acid by reacting a starting material and oxygen in the presence of a heterogeneous catalyst and p-xylene as solvent to produce a solution of terephthalic acid (TPA). The starting material is p-xylene, p-toluic acid, 4 carboxybenzaldehyde, or a mixture of any two or more thereof. No solid TPA is formed during the reaction in contrast to previous manufacturing methods that utilize acidic solvents and precipitate TPA as it forms. By avoiding the direct precipitation of TPA during formation, the present methods avoid many shortcomings of the conventional manufacturing methods used to produce TPA. In particular, the present methods do not require additional purification steps to remove reaction byproducts; film grade TPA can be obtained directly from starting material in a one-step process.Type: GrantFiled: December 20, 2005Date of Patent: May 29, 2012Assignee: Process Design Center B.V.Inventors: Johannes Maria Franciscus Sijben, Herman Jozef Claudius De Meyer
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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: 8173835Abstract: Disclosed is a method and apparatus for drying a wet cake in a carboxylic acid production process. The method comprises employing a contact dryer for drying solid particles of carboxylic acid, where the solid particles can have a residence time of less than about 7 minutes in the dryer and an exit temperature of less than about 250° C. upon exiting the dryer.Type: GrantFiled: February 1, 2007Date of Patent: May 8, 2012Assignee: Grupo Petrotemex, S.A. DE C.V.Inventors: Kenny Randolph Parker, Philip Edward Gibson
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Patent number: 8173836Abstract: Disclosed is a method and apparatus for drying a wet cake in a carboxylic acid production process. The method comprises employing a contact dryer for drying solid particles of carboxylic acid, where the solid particles can have a residence time of less than about 7 minutes in the dryer and an exit temperature of less than about 250° C. upon exiting the dryer.Type: GrantFiled: February 1, 2007Date of Patent: May 8, 2012Assignee: Grupo Petrotemex, S.A. De C.V.Inventors: Kenny Randolph Parker, Philip Edward Gibson
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Patent number: 8173834Abstract: A process and apparatus for manufacture of aromatic carboxylic acids comprises a liquid phase oxidation of aromatic hydrocarbon feed materials and treatment of a high pressure off-gas from the liquid phase oxidation to separate water and reaction solvent and purification of impure aromatic carboxylic acid products wherein a purification liquid includes water from off-gas treatment.Type: GrantFiled: March 20, 2006Date of Patent: May 8, 2012Assignee: BP Corporation North America Inc.Inventor: Thomas M. Bartos
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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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Publication number: 20120101300Abstract: A method for making a hydrophilic carbon nanotube film is provided. A reactor, an oxidative acid solution disposed in the reactor, and at least one primary carbon nanotube film are provided. The primary carbon nanotube film is set in the reactor disposed apart from the oxidative acid solution. The oxidative acid solution is then volatilized to form oxidative acid gas and the reactor is filled with the oxidative acid gas.Type: ApplicationFiled: December 25, 2010Publication date: April 26, 2012Applicants: HON HAI PRECISION INDUSTRY CO., LTD., TSINGHUA UNIVERSITYInventors: ZHI-MIN TAO, LI FAN, WEN-MEI ZHAO
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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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Publication number: 20120095143Abstract: A method for dispersing nanotubes, comprising forming a nanocomposite solution with associated nanotubes and nanoplatelets, mixing a surfactant to the nanocomposite solution, separating the nanocomposite in solution, wherein the nanotubes remain suspended in the surfactant solution, and isolating the nanotubes in solution. In certain instances, the method further comprises functionalizing the nanotubes in solution.Type: ApplicationFiled: December 28, 2010Publication date: April 19, 2012Applicants: KANEKA TEXAS CORPORATION, THE TEXAS A&M UNIVERSITY SYSTEMInventors: Hung-Jue Sue, Xi Zhang, Riichi Nishimura
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Publication number: 20120041226Abstract: The present invention relates to an improved process of ozonolysis of carbon nanotubes assisted by water vapour. The improved methodology provides an eco-friendly, cheaper, practical and efficient approach to functionalize carbon nanotubes with oxygen-containing moieties for further chemical functionalization and composite dispersion.Type: ApplicationFiled: February 27, 2010Publication date: February 16, 2012Applicant: BAYER MATERIALsCIENCE AGInventors: Helmut Meyer, Stefan Bahnmüller, Julia Hitzbleck, Zhong Zhang, Lu-Qi Liu, Ke Peng, Hongchao Li
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Publication number: 20120004448Abstract: A process and a mixture for oxidizing an alkyl-aromatic compound comprises forming a mixture comprising the alkyl-aromatic compound, a solvent, a bromine source, a catalyst, and ammonium acetate; and contacting the mixture with an oxidizing agent at oxidizing conditions to produce an oxidation product comprising at least one of an aromatic aldehyde, an aromatic alcohol, an aromatic ketone, and an aromatic carboxylic acid. The solvent comprises a carboxylic acid having from 1 to 7 carbon atoms; and the catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium.Type: ApplicationFiled: June 8, 2011Publication date: January 5, 2012Applicant: UOP LLCInventors: Alakananda Bhattacharyya, Joel T. Walenga
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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: 20110213180Abstract: A method for producing isophthalic acid, comprising: subjecting a m-phenylene compound and a molecular-oxygen-containing gas to liquid-phase oxidation reaction in the presence of a catalyst comprising a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby precipitate isophthalic acid; removing the isophthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor by following steps (1) to (4) as described.Type: ApplicationFiled: March 15, 2011Publication date: September 1, 2011Applicant: Mitsubishi Gas Chemical Company, Inc.Inventors: Fumiya ZAIMA, Nobuo Namiki, Hideaki Fujita, Masato Inari
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Publication number: 20110213181Abstract: A method for producing terephthalic acid comprising: subjecting a p-phenylene compound to a liquid-phase oxidation reaction by the use of a molecular-oxygen-containing gas in the presence of a catalyst at least containing a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby cause terephthalic acid to precipitate; removing the terephthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor through a series of operations (1) to (4), as described, for reusing at least a portion of the catalyst in the liquid-phase oxidation reaction.Type: ApplicationFiled: March 15, 2011Publication date: September 1, 2011Applicants: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., LTD., MIZUSHIMA AROMA COMPANY, LTD.Inventors: Fumiya ZAIMA, Masato Inari, Hideaki Fujita, Nobuo Namiki
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Publication number: 20110184208Abstract: An oxidation process for the production of an aromatic carboxylic acid, said process comprising contacting in the presence of a catalyst, within a continuous flow reactor, one or more precursor(s) of the aromatic carboxylic acid with an oxidant, such contact being effected with said precursor(s) and the oxidant in an aqueous solvent comprising water under supercritical conditions or near supercritical conditions, wherein said catalyst comprises copper.Type: ApplicationFiled: April 29, 2009Publication date: July 28, 2011Inventors: Joan Fraga-Dubreuil, Samuel Duncan Housley, Walter Partenheimer
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Patent number: 7956200Abstract: A multimetal oxide of the formula I Aga-bMbV2Ox*cH2O,??I where M is a metal selected from the group consisting of Li, Na, K, Rb, Cs, Tl, Mg, Ca, Sr, Ba, Cu, Zn, Cd, Pb, Cr, Au, Al, Fe, Co, Ni and/or Mo, a is from 0.3 to 1.9 and b is from 0 to 0.5, with the proviso that the difference (a?b)?0.1 and c is from 0 to 20 and x is a number determined by the valence and amount of elements different from oxygen in the formula I, which has a crystal structure giving an X-ray powder diffraction pattern which displays reflections at the lattice spacings d of 15.23±0.6, 12.16±0.4, 10.68±0.3, 3.41±0.04, 3.09±0.04, 3.02±0.04, 2.36±0.04 and 1.80±0.04 ?. Precatalysts and catalysts produced therefrom for the partial oxidation of aromatic hydrocarbons are also provided.Type: GrantFiled: February 7, 2010Date of Patent: June 7, 2011Assignee: BASF AktiengesellschaftInventors: Thomas Heidemann, Hartmut Hibst, Stefan Bauer, Ulf Dietrich
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Patent number: 7935844Abstract: Energy is recovered during the production of aromatic carboxylic acids by liquid phase oxidation of aromatic hydrocarbons by performing a high efficiency separation on the reactor overhead vapor to form a high pressure gaseous overhead stream comprising water and organic impurities; recovering heat energy from the high pressure gaseous overhead stream by exchanging heat with a suitable heat sink material such that a condensate comprising from about 20 wt % to about 60 wt % of the water present in the high pressure gaseous overhead stream is formed and a high pressure off-gas is formed; and recovering energy in the form of work from the high pressure off-gas. Preferably such work is recovered using isentropic means for energy recovery, for example an expander. Apparatus for such process is also provided.Type: GrantFiled: March 20, 2006Date of Patent: May 3, 2011Assignee: BP Corporation North America Inc.Inventor: Thomas M. Bartos
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Patent number: 7910749Abstract: A method oxidizes an organic compound with oxygen in the presence of a catalyst, in which the catalyst contains a N-hydroxy- or N-(substituted oxy)-imide compound derivable from at least one selected from a target product, a reaction intermediate, and a reaction byproduct, and the catalyst is produced from at least one component selected from the target product, reaction intermediate, and reaction byproduct each formed as a result of the reaction and is used in the oxidation reaction so as to make up for a loss of the catalyst due to denaturation in the reaction. The method can easily and inexpensively make up for a loss of the catalyst denaturated in the course of reaction.Type: GrantFiled: February 22, 2006Date of Patent: March 22, 2011Assignee: Daicel Chemical Industrial, Ltd.Inventors: Yasuteru Kajikawa, Naruhisa Hirai, Jun Kuwana
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Patent number: 7902396Abstract: 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 24, 2009Date of Patent: March 8, 2011Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Gino Georges Lavoie, Charles Edwan Sumner, Jr.
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Patent number: 7897810Abstract: Disclosed is an optimized process and apparatus for more efficiently producing aromatic dicarboxylic acids (e.g., terephthalic acid). In one embodiment the process/apparatus reduces costs by recovering and purifying residual terephthalic acid present in the liquid phase of an initial oxidation slurry. In another embodiment the process apparatus reduces costs associated with hydrogenation by forming a final composite product containing unhydrogenated acid particles.Type: GrantFiled: March 18, 2008Date of Patent: March 1, 2011Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede
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Patent number: 7888530Abstract: Disclosed is an optimized process and apparatus for more efficiently producing aromatic dicarboxylic acids (e.g., terephthalic acid). In one embodiment the process/apparatus reduces costs by recovering and purifying residual terephthalic acid present in the liquid phase of an initial oxidation slurry. In another embodiment the process apparatus reduces costs associated with hydrogenation by forming a final composite product containing unhydrogenated acid particles.Type: GrantFiled: July 14, 2005Date of Patent: February 15, 2011Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede
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Patent number: 7884232Abstract: 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: March 1, 2006Date of Patent: February 8, 2011Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Thomas Young Lightfoot, Thomas Earl Woodruff, Charles Helton Hitchcock, David Lee Denton, Carl Norman McCurry
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Publication number: 20100228047Abstract: In a process for oxidizing a hydrocarbon to the corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, a reaction medium comprising a hydrocarbon is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH and NO2, or from the atoms H, F, Cl, Br and I provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N, and CR3; each of X and Z is independently selected from C, S, CH2, N, P and an element of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; l is 0, 1, or 2; m is 1 to 3; and R3 can be any of the entities listed for R1.Type: ApplicationFiled: October 8, 2008Publication date: September 9, 2010Inventors: Francisco M. Benitez, Jihad M. Dakka, Edmund J. Mozeleski, Stephen Zushma, John Scott Buchanan, Jon E. Stanat
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Publication number: 20100228048Abstract: A process for preparing an aromatic carboxylic acid having a heteroatom containing substituent is provided that includes reaction in a vessel of an aromatic precursor having an aromatic core with at least one heteroatom containing substituent and at least one hydrogen extending from the core, with a haloacetonitrile under reaction conditions to form an aromatic acetonitrile with an acetonitrile moiety. The aromatic acetonitrile is exposed to an oxidizing agent under conditions to convert the acetonitrile moiety to a carboxylic acid group to prepare the aromatic carboxylic acid having the heteroatom containing substituent.Type: ApplicationFiled: March 8, 2010Publication date: September 9, 2010Applicant: PerkinElmer Health Sciences, Inc.Inventors: Crist N. Filer, Terence P. Kelly, Chrisopher Wright
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Publication number: 20100222609Abstract: In a process for oxidizing a hydrocarbon to a corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH and NO2, or from the atoms H, F, Cl, Br and I provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N and CR3; each of X and Z is independently selected from C, S, CH2, N, P and elements of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; 1 is 0, 1, or 2; m is 1 to 3, and R3 can be any of the entities listed for R1.Type: ApplicationFiled: October 8, 2008Publication date: September 2, 2010Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
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Publication number: 20100145094Abstract: 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: ApplicationFiled: May 1, 2008Publication date: June 10, 2010Applicant: 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
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Publication number: 20100113824Abstract: The invention provides improved energy content in and shaft power recovery from off-gas from xylene oxidation reactions while at the same time minimizing wastewater treatment cost. More shaft power is produced using off-gas than is required to drive the main air compressor, even with preferred, relatively low oxidation temperatures. Simultaneously, an amount of wastewater greater than byproduct water from oxidation of xylene is kept in vapor form and treated along with off-gas pollutants in a self-sustaining (self-fueling) gas-phase thermal oxidative destruction unit. Optionally, off-gas is combined from multiple xylene oxidation reactors, comprising primary and/or secondary oxidation reactors and forming TPA and/or IPA. Optionally, air compressor condensate and caustic scrubber blowdown are used in a TPA process or as utility water, effectively eliminating normal flow of liquid wastewater effluent from a TPA plant.Type: ApplicationFiled: September 9, 2009Publication date: May 6, 2010Applicant: EASTMAN CHEMICAL COMPANYInventors: Raymond Elbert Fogle, III, Ronald Buford Sheppard, Timothy Alan Upshaw, Alan George Wonders