With Recycle Or Recovery Of Reaction Component Patents (Class 562/414)
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Patent number: 7498002Abstract: 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: August 29, 2007Date of Patent: March 3, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Howard Wood Jenkins, Jr., Lee Reynolds Partin, Wayne Scott Strasser, Marcel deVreede
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Patent number: 7494641Abstract: Disclosed is a process that relates to the recovery of a metal catalyst from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic acid. The process involves the addition of a wash solution to a high temperature molten dispersion to recover the metal catalyst and then subjecting an aqueous mixture or purified aqueous mixture so formed to a single stage extraction to remove organic impurities to produce an extract stream and a raffinate stream comprising the metal catalyst.Type: GrantFiled: September 23, 2004Date of Patent: February 24, 2009Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede
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Patent number: 7495125Abstract: 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: February 24, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede
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Patent number: 7491369Abstract: 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: August 29, 2007Date of Patent: February 17, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Thomas Earl Woodruff, Ronald Buford Sheppard, Wayne Scott Strasser
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Patent number: 7485746Abstract: A process for oxidation with oxygen of at least one aromatic hydrocarbon having oxidizable, substituents that maximizes the utilization of oxygen without reduction in the quality of the carboxylic acid products produced by means of a stagewise countercurrent oxidation system is disclosed.Type: GrantFiled: November 14, 2003Date of Patent: February 3, 2009Assignee: BP Corporation North America Inc.Inventors: Frank G. Belmonte, David L. Sikkenga, Olusola Sunday Ogundiran, Kenneth J. Abrams, Linus Kai-Wah Leung, Christopher G. Meller, Dale A. Figgins, Allen B. Mossman
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Patent number: 7482482Abstract: 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: January 27, 2009Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Marcel de Vreede, Lee Reynolds Partin, Wayne Scott Strasser
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Patent number: 7470370Abstract: A process is disclosed that relates to the recovery of a metal catalyst from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic. More particularly, the process involves recovery of a metal catalyst from an oxidizer purge stream through the use of a pressure filter, the combining of water with a mother liquor to recover the metal catalyst and then subjecting an aqueous mixture so formed to a single stage extraction with an extraction solvent to produce an extract stream comprising organic impurities and a raffinate stream comprising the metal catalyst.Type: GrantFiled: August 21, 2007Date of Patent: December 30, 2008Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Robert Lin
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Patent number: 7468456Abstract: An improved process for producing an aromatic carboxylic acid from an aromatic alkyl hydrocarbon is described, wherein the improvement comprises using the same aromatic alkyl hydrocarbon as the azeotropic agent for separation of acetic acid and methyl acetate from water via azeotropic distillation. The process of this invention has considerable advantages over other known processes, particularly in regards to consumption of the azeotropic agent and utilities, formation of undesirable impurities and operating costs.Type: GrantFiled: July 11, 2006Date of Patent: December 23, 2008Assignee: ANT CorporationInventors: Myron Myonkee Lee, Duk-Jun Kwon, Dong-Won Lee, Alexander Jongwon Lee
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Publication number: 20080194865Abstract: 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: ApplicationFiled: March 20, 2006Publication date: August 14, 2008Applicant: BP Corporation North America Inc.Inventor: Thomas M. Bartos
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Patent number: 7410632Abstract: A method for removing impurities from a mother liquor comprising a carboxylic acid, a metal catalyst, impurities by (a) evaporating the mother liquor comprising a carboxylic acid, the metal catalyst, impurities, water and a solvent in a first evaporator zone to produce a vapor stream and a concentrated mother liquor stream; (b) evaporating the concentrated mother liquor stream in a second evaporator zone to form a solvent rich stream and a super concentrated mother liquor stream; (c) separating organic impurities with a water-solvent solution from the super concentrated mother liquor in a solid-liquid separation zone to form an aqueous stream and a second aqueous stream; (d) mixing in a mixing zone water and optionally and extraction solvent with the aqueous stream and second aqueous stream to form an aqueous mixture; and (e) adding an extraction solvent to the aqueous mixture in an extraction zone to form an extract stream and a raffinate stream.Type: GrantFiled: June 5, 2003Date of Patent: August 12, 2008Assignee: Eastman Chemical CompanyInventor: Robert Lin
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Patent number: 7402694Abstract: A process is disclosed that relates to the removal of impurities, specifically benzoic acid, from a mother liquor produced in the synthesis of carboxylic acid, typically terephthalic acid.Type: GrantFiled: August 11, 2005Date of Patent: July 22, 2008Assignee: Eastman Chemical CompanyInventors: Robert Lin, Philip Edward Gibson, Kenny Randolph Parker
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Patent number: 7399882Abstract: 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: July 15, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Howard Wood Jenkins, Jr., Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede
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Patent number: 7390921Abstract: 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: June 24, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Marcel de Vreede, Lee Reynolds Partin, Wayne Scott Strasser, Puneet Gupta
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Patent number: 7381386Abstract: A method for removing impurities from a mother liquor comprising a carboxylic acid, a metal catalyst, impurities by (a) evaporating the mother liquor comprising a carboxylic acid, a metal catalyst, impurities and a solvent in a first evaporator zone to produce a vapor stream and a concentrated mother liquor stream; (b) evaporating the concentrated mother liquor stream in a second evaporator zone to form a solvent rich stream and a super concentrated mother liquor stream; (c) mixing in a mixing zone a water-solvent solution and optionally an extraction solvent with the super concentrated mother liquor stream to form an aqueous mixture; (d) optionally separating organic impurities from the aqueous mixture in a solid-liquid separation zone to form a purified aqueous mixture; and (e) extracting the aqueous mixture or purified aqueous mixture with an extraction solvent in an extraction zone to form an extract stream and the raffinate stream.Type: GrantFiled: June 5, 2003Date of Patent: June 3, 2008Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede
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Patent number: 7381836Abstract: 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: June 3, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Lee Reynolds Partin, Wayne Scott Strasser, Marcel de Vreede, Puneet Gupta
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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: 7371894Abstract: 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: May 13, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Marcel de Vreede, Lee Reynolds Partin, Wayne Scott Strasser
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Patent number: 7361784Abstract: 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 22, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Gino Georges Lavoie, Charles Edwan Sumner, Jr.
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Patent number: 7358389Abstract: 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: April 15, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Thomas Earl Woodruff, Ronald Buford Sheppard, Wayne Scott Strasser
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Patent number: 7355068Abstract: 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: April 8, 2008Assignee: Eastman Chemical CompanyInventors: Alan George Wonders, Thomas Earl Woodruff, Ronald Buford Sheppard, Wayne Scott Strasser
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Patent number: 7314954Abstract: A system and a method for recovering PTA (purified terephthalic acid) mother liquid as well as purifying and regenerating catalyst, the system and the method is used mainly in manufacturing PTA wherein the mother liquid of the PTA generated by hydrogenation reaction is recovered by means of a PTA mother liquid recovering system to produce cobalt containing inorganic acid solution which is passed through a catalyst purifying/regenerating system and is electrolyzed with a cobalt purifying/regenerating system to produce metal cobalt which is then passed through an oxidized catalyst producing system to produce oxidized catalyst to be circulated for use in the process of manufacturing PTA.Type: GrantFiled: November 9, 2006Date of Patent: January 1, 2008Assignee: Mechema Chemicals International Corp.Inventor: David Yen
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Patent number: 7291270Abstract: A process is disclosed that relates to the removal of impurities and the recovery of a mother liquor and wash filtrate from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic. More particularly, the process involves the removal of impurities and the recovery of a mother liquor and wash filtrate from an oxidizer purge stream and then routing the mother liquor and or wash filtrate to an oxidation zone.Type: GrantFiled: October 28, 2004Date of Patent: November 6, 2007Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker, Howard Wood Jenkins, Jr.
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Patent number: 7285677Abstract: A system/method for recovering CTA (crude terephthalic acid) residues and purifying and regenerating catalyst, being used for recovering residues generated in the reaction processes of oxidation in manufacturing PTA (purified terephthalic acid) as well as purifying and regenerating the residues to form oxidized catalyst to be circulated for reusing; wherein there are mainly a CTA residue recovering system and a catalyst purifying/regenerating system. The CTA residue recovering system treats the CTA residues and collects metallic salt that is then sent to the catalyst purifying/regenerating system and is reduced by electrolyzing metal cobalt with a cobalt purifying/ regenerating system, then is passed to an oxidized catalyst producing system to produce oxidized catalyst to be circulated for use in the oxidation reaction process for manufacturing PTA.Type: GrantFiled: November 13, 2006Date of Patent: October 23, 2007Assignee: Mechema Chemicals International Corp.Inventor: David Yen
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Patent number: 7282151Abstract: A process is disclosed that relates to the recovery of a metal catalyst from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic. More particularly, the process involves recovery of a metal catalyst from an oxidizer purge stream through the use of a pressure filter, the combining of water with a mother liquor to recover the metal catalyst and then subjecting an aqueous mixture so formed to a single stage extraction with an extraction solvent to produce an extract stream comprising organic impurities and a raffinate stream comprising the metal catalyst.Type: GrantFiled: June 23, 2004Date of Patent: October 16, 2007Assignee: Eastman Chemical CompanyInventors: Kenny Randolph Parker, Robert Lin
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Patent number: 7273559Abstract: A process is disclosed that relates to the removal of impurities and the recovery of a mother liquor and wash filtrate from an oxidizer purge stream produced in the synthesis of carboxylic acid, typically terephthalic. More particularly, the process involves the removal of impurities and the recovery of a mother liquor and wash filtrate from an oxidizer purge stream and then routing the mother liquor and or wash filtrate to an oxidation zone.Type: GrantFiled: October 28, 2004Date of Patent: September 25, 2007Assignee: Eastman Chemical CompanyInventors: Philip Edward Gibson, Kenny Randolph Parker, Howard Wood Jenkins, Jr.
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Patent number: 7238833Abstract: A process for the production of an aromatic carboxylic acid comprising contacting in the presence of a catalyst, within a continuous flow reactor, one or more precursors 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 close to the supercritical point such that said one or more precursors, oxidant and aqueous solvent constitute a substantially single homogeneous phase in the reaction zone, wherein the contact of at least part of said precursor with said oxidant is contemporaneous with contact of said catalyst with at least part of said oxidant.Type: GrantFiled: April 28, 2004Date of Patent: July 3, 2007Assignee: Invista North America S.A.R.L.Inventors: Derek Alexander Graham, Paul Anthony Hamley, Raymond Oliver, Martyn Poliakoff, Duncan C. Woodcock, Thomas Iikenhans
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Patent number: 7153480Abstract: A reactor for the oxidation of a precursor to an aromatic carboxylic acid or ester thereof in a liquid phase reaction mixture is disclosed. The reactor comprises an elongate vessel, substantially vertical in use, having an upper mixing element and a lower mixing element, characterised in that the upper mixing element is an axial pumping impeller and the lower mixing element is a radial pumping impeller. A process of producing a carboxylic acid or ester thereof in a reactor of the invention is also disclosed. In use, the configuration of mixing elements leads to three highly turbulent mixing zones. In a preferred embodiment of the process of the present invention oxidant, from one inlet, and solvent, precursor and catalyst, are introduced directly into a mixing zone. The highly turbulent mixing zones lead to rapid mass transfer suppressing the formation of unwanted, coloured by-products and reduced reactor fouling.Type: GrantFiled: May 22, 2003Date of Patent: December 26, 2006Inventors: David Robert Bickham, Michael Cooke, Martin Reid Burton Davis, Samuel Duncan Housley, Finbar Gerald McDonnell
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Patent number: 7135596Abstract: This invention relates to control or removal of amounts of dissolved iron that may be present in liquid process streams in the manufacture of aromatic acids. The present invention further relates to the control or removal of dissolved iron contaminants present in liquid streams during the manufacture of a crude aromatic acid. The present invention also further relates to the control or removal of dissolved iron contaminants present in liquid streams during the purification of a crude aromatic acid. The present invention also further relates to controlling of decreasing the formation of iron oxides on the surfaces of equipment used during the manufacture of crude aromatic acid and/or purification of crude aromatic acid.Type: GrantFiled: April 22, 2003Date of Patent: November 14, 2006Assignee: BP Corporation North America Inc.Inventors: Philip O. Nubel, Timothy H. Keyes, Ricky L. Wittman
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Patent number: 7060853Abstract: The present invention relates to a method for increasing the production capacity of a conventional oxidation reactor for catalytic liquid phase oxidation of paraxylene by staging the oxidation reaction into a first high pressure and high solvent ratio reaction zone followed by the conventional reactor.Type: GrantFiled: March 21, 2003Date of Patent: June 13, 2006Assignee: Invista North America S.a r.l.Inventors: Samuel Duncan Housley, John A. Turner
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Patent number: 7049465Abstract: This invention relates to a process for the manufacture of aromatic carboxylic acids by exothermic liquid phase oxidation of an aromatic feedstock. More particularly, this invention relates to the efficient energy recovery of the exotherm produced by the liquid phase oxidation of an aromatic feedstock. An apparatus useful in recovery of energy from the preparation of aromatic carboxylic acids by the exothermic liquid phase reaction of an aromatic feedstock is described where the primary means of energy recovery is by raising moderate pressure steam. This is coupled with a process to recovery low temperature energy using a process commonly known as an organic Rankine cycle and/or a heat pump. The combination of energy recovery methods increases the overall energy recovery and enables the recovery of reaction energy as either thermal energy (steam) or work or a combination of both.Type: GrantFiled: July 10, 2003Date of Patent: May 23, 2006Assignee: Eastman Chemical CompanyInventor: Robert Lin
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Patent number: 7022307Abstract: The present invention relates to a method for gas-solid contacting in a bubbling fluidized bed reactor by: (a) introducing into a reactor with bed length to bed diameter ratio below about 5.Type: GrantFiled: December 2, 2003Date of Patent: April 4, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ramchandra Choudhary, Tushar Vasant Choudhary
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Patent number: 6949673Abstract: Improved process for producing aromatic carboxylic acids by catalytic liquid phase oxidation of a corresponding precursor in a suitable solvent comprising feeding the reactants to a first oxidation reaction zone at high pressure and high solvent ratio, wherein uptake of oxygen is less than that required for full conversion of the precursor to its corresponding carboxylic acid, and then feeding the resulting reaction medium to a second oxidation reaction zone.Type: GrantFiled: March 21, 2003Date of Patent: September 27, 2005Assignee: E.I. Du Pont de Nemours and CompanyInventors: Samuel Duncan Housley, John A Turner
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Patent number: 6852879Abstract: Disclosed is a method and solvent composition capable of removing iron oxide deposits from the surface of titanium components without substantially damaging the underlying titanium component. Iron oxide deposits may be removed from the surface of a titanium component by contacting the titanium component with the solvent composition of the invention. The solvent composition may then be removed from contact with the titanium component to obtain a recyclable solvent composition which is recycled into repeated contact with the titanium component. The solvent composition comprises an aqueous mixture of an organic acid and a hydrohalide acid.Type: GrantFiled: September 26, 2002Date of Patent: February 8, 2005Assignee: BP Corporation North America Inc.Inventors: Frank G. Belmonte, Kenneth J. Abrams, James Delaney, Jr., Scott G. Kramer, David L. Sikkenga
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Publication number: 20040210084Abstract: A process for the preparation of 2,6-naphthalenedicarboxylic acid by liquid phase oxidation in acidic solution of 2,6-dimethylnaphthalene in presence of a cobalt-manganese-bromine-catalyst. An oxygen containing feed gas is introduced into the reaction zone such that the oxygen content in the dry exhaust gas does not exceed 1 percent by volume.Type: ApplicationFiled: March 5, 2004Publication date: October 21, 2004Inventors: Gian Luca Castiglioni, Carlo Fumagalli, Roberto Pirola
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Patent number: 6765113Abstract: A process for the production of an aromatic carboxylic acid comprising contacting in the presence of a catalyst, within a continuous flow reactor, one or more precursors 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 close to the supercritical point such that said one or more precursors, oxidant and aqueous solvent constitute a substantially single homogeneous phase in the reaction zone, wherein the contact of at least part of said precursor with said oxidant is contemporaneous with contact of said catalyst with at least part of said oxidant.Type: GrantFiled: July 13, 2001Date of Patent: July 20, 2004Assignee: E.I. Du Pont de Nemours and CompanyInventors: Derek Alexander Graham, Paul Anthony Hamley, Raymond Oliver, Martyn Poliakoff, Duncan Woodcock, Thomas Ilkenhans
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Patent number: 6761860Abstract: 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: June 3, 2002Date of Patent: July 13, 2004Inventors: Franco Codignola, Antonio Moro
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Publication number: 20040122116Abstract: The present invention relates to a method for gas-solid contacting in a bubbling fluidized bed reactor by:Type: ApplicationFiled: December 2, 2003Publication date: June 24, 2004Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCHInventors: Vasant Ramchandra Choudhary, Tushar Vasant Choudhary
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Publication number: 20040044246Abstract: This invention relates to control or removal of amounts of dissolved iron that may be present in liquid process streams in the manufacture of aromatic acids. The present invention further relates to the control or removal of dissolved iron contaminants present in liquid streams during the manufacture of a crude aromatic acid. The present invention also further relates to the control or removal of dissolved iron contaminants present in liquid streams during the purification of a crude aromatic acid. The present invention also further relates to controlling of decreasing the formation of iron oxides on the surfaces of equipment used during the manufacture of crude aromatic acid and/or purification of crude aromatic acid.Type: ApplicationFiled: April 22, 2003Publication date: March 4, 2004Inventors: Phillip O. Nubel, Timothy H. Keyes, Ricky L. Wittman
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Patent number: 6689903Abstract: Disclosed is a method for the recovery of crystalline terephthalic acid containing less than about 150 ppmw p-toluic acid by subjecting a solution of terephthalic acid containing minor amounts of p-toluic acid to crystallization in a crystallization zone comprising a plurality of series-connected crystallizers wherein the solution is subjected to rate-controlled evaporative cooling by sequential reduction in pressure and temperature to cause crystallization of terephthalic acid, wherein the pressure of the solution at the end of the crystallization zone is about ambient pressure or less. Solvent which is evaporated from the crystallizers is collected and condensed and the condensed solvent is returned to the crystallization zone at a point subsequent to the crystallizer from which it was obtained.Type: GrantFiled: May 30, 2002Date of Patent: February 10, 2004Assignee: Eastman Chemical CompanyInventors: Ruairi Seosamh O'Meadhra, Robert Lin, Shane Kipley Kirk, Brian David McMurray
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Patent number: 6642407Abstract: This invention provides a process for purifying the crude aromatic dicarboxylic acids produced by oxidation of dialkyl aromatic hydrocarbons and for using the purified acids in the preparation of polyethylene terephthalate, polyethylene naphthalate and other polyesters. The invention simplifies the manufacturing process by converting the crude aromatic acids into bis-glycol esters in an esterification reactor 4, from which the esterified partial oxidation impurities present in the oxidation product are removed by distillation in distillation tower 5. After removal of the volatile impurities, the dicarboxylic acid esters can separated by distillation in distillation tower 6 or by crystallization and converted to polyesters by polycondensation. The volatile impurities removed as overhead from tower 5 can be recycled as stream 16 to the oxidation reactor where they act as oxidation promoters thereby optionally allowing for a bromine-free oxidation process for dialkyl aromatic hydrocarbons.Type: GrantFiled: April 26, 2002Date of Patent: November 4, 2003Assignee: Exxon Mobil Chemical Patents Inc.Inventors: Krishna Kulai Rao, Russell D. Sellen, Xiaobing Feng, James Spanswick, William F. Huber, Jr.
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Patent number: 6620966Abstract: There is disclosed a process for continuously producing an aromatic carboxylic acid comprising the steps of (A) subjecting a poly-alkyl aromatic hydrocarbon to a liquid-phase oxidation by continuously supplying an oxidation reactor with said hydrocarbon, a catalyst, a reaction accelerator, acetic acid containing water and a gas containing molecular oxygen; (B) continuously taking out from the oxidation reactor, the reaction products containing aromatic carboxylic acids, and separating the same into crude aromatic carboxylic acids and acetic acid containing water; and (C) continuously taking out from the oxidation reactor, the oxidative reaction exhaust gas containing evaporated acetic acid containing water, introducing the above gas in a condenser, and condensing the above evaporated acid, wherein acetic acid containing water is supplied to an oxidative reaction exhaust gas inlet line leading to the condenser.Type: GrantFiled: January 16, 2002Date of Patent: September 16, 2003Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.Inventors: Fumio Ohkoshi, Ikuo Tsuboi, Nirou Hoshishima
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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: 6506931Abstract: A process for producing an aromatic carboxylic acid by a liquid phase oxidation of an alkylaromatic compound with molecular oxygen in a reaction solvent comprising a lower aliphatic carboxylic acid in the presence of an oxidation catalyst, in which an aromatic carboxylic acid having an improved hue of the powdery product thereof and exhibiting an improved light transmittance when dissolved in an aqueous solution of a base can be produced efficiently in a simple manner by suppressing contamination due to the intermediates and by-products formed by side reactions, the said process comprising performing the liquid phase oxidation of the alkylaromatic compound in the presence of a hydrogen gas-treated liquid containing the catalyst.Type: GrantFiled: September 7, 2000Date of Patent: January 14, 2003Assignee: Mitsui Chemicals, Inc.Inventors: Masayasu Ishibashi, Hiroshi Tomita
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Patent number: 6500347Abstract: A process for recovering crystals from a slurry which comprises supplying a slurry comprising crystals and a solvent to a rotary vacuum filter and successively conducting filtration under suction, washing, filtration under suction and cleavage of a cake continuously by rotation of a cylindrical filter medium, wherein a vapor having a same composition as that of the solvent is supplied as a blowing gas for cleaving the cake. The crystals can be continuously recovered for a long period of time without clogging of a filter medium when the crystals are recovered from a slurry by using a rotary vacuum filter.Type: GrantFiled: July 3, 2001Date of Patent: December 31, 2002Assignees: Mitsubishi GAs Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.Inventors: Fumio Ohkoshi, Masato Inari
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Publication number: 20020193630Abstract: 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: ApplicationFiled: May 31, 2002Publication date: December 19, 2002Inventors: Robert Lin, Ruairi Seosamh O'Meadhra, Ronald Buford Kingsport
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Publication number: 20020188155Abstract: 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: ApplicationFiled: June 3, 2002Publication date: December 12, 2002Inventors: Franco Codignola, Antonio Moro
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Publication number: 20020183546Abstract: Disclosed is a process for producing a benzenedicarrboxylic acid such as terephthalic acid wherein a dialkyl benzene compound and acetic acid having catalyst components dissolved therein are fed to a first reaction zone wherein the dialkyl benzene compound is oxidized with molecular oxygen to provide a first oxidation zone product comprising a benzenedicarboxylic acid containing minor amounts of mono-carboxylic acid by-products such as carboxybenzaldehyde and toluic acid. The first oxidation zone product comprising a slurry of a benzenedicarboxylic acid containing minor amounts of mono-carboxylic acid by-products is fed to a second oxidation reaction zone that is operated under more severe conditions of temperature and pressure. The rate of the feed of a molecular oxygen containing gas to the second oxidation zone is about 3% or less of the the rate of the feed of the molecular oxygen containing gas to the first oxidation zone.Type: ApplicationFiled: May 28, 2002Publication date: December 5, 2002Inventors: Ronald Buford Sheppard, Charles Edwan Sumner, Brent Alan Tennant
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Patent number: 6476257Abstract: The present invention relates to a method for preparing aromatic carboxylic acid from alkylaromatics by liquid-phase oxidation. More particularly, the present invention relates to a method for preparing aromatic carboxylic acid from alkylaromatics by oxidation in acetic acid as solvent with oxygen-containing gas in the presence of cobalt/manganese/bromine complex catalyst, wherein nickel and carbon dioxide in an appropriate amount are added to increase an activity of cobalt/manganese/bromine complex catalyst. Especially nickel has a synergistic effect with carbon dioxide and maximize the to formation of the desired product having the corresponding carboxylic groups to the number of alkyl groups in a reactant.Type: GrantFiled: September 28, 2001Date of Patent: November 5, 2002Assignee: Korea Institute of Chemical TechnologyInventors: Sang-Eon Park, Jin S. Yoo, Ki-Won Jun, David B. Raju, Young-Ho Kim
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Patent number: 6448436Abstract: Disclosed is an integrated process for producing 2,6-naphthalene dicarboxylicacid comprising oxidizing a methylnaphthalene feedstock, hydrodebrominating the crude naphthoic acid product under conditions different from any work known in the art, forming a potassium salt of the acid; disproportionating the potassium salt to produce 2,6 potassium salts of NDA; selectively precipitating K2NDA; selectively precipitating the monopotassium salt of 2,6 NDA(KHNDA); disproportionating the KHNDA into 2,6 NDA and K2NDA; further reacting the 2,6 NDA in a pipe reactor; and drying the product 2,6 NDA by conventional means or directly slurrying directly into a PEN process. The process can tolerate impurities in the economical methylnaphthalene feed and the resulting 2,6 NDA is of high quality with <50 ppm potassium.Type: GrantFiled: August 22, 2000Date of Patent: September 10, 2002Assignee: Mossi & Ghisolfi Overseas, S. A.Inventors: Keith Michael Kreitman, Steve Edward Brewer, John Bernard Rodden, Robert Lawrence Blackbourn, Thomas Fairchild Brownscombe, James Laurel Buechele, Ye-Mon Chen, Zaida Diaz, Donn Anthony DuBois, Raymond Lawrence June, Brendan Dermot Murray, Michael Wayne Potter
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Patent number: 6437176Abstract: 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:Type: GrantFiled: March 19, 2001Date of Patent: August 20, 2002Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura