RU2014131232A - METHOD FOR PRODUCING TERPHTHALIC ACID - Google Patents

METHOD FOR PRODUCING TERPHTHALIC ACID Download PDF

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RU2014131232A
RU2014131232A RU2014131232A RU2014131232A RU2014131232A RU 2014131232 A RU2014131232 A RU 2014131232A RU 2014131232 A RU2014131232 A RU 2014131232A RU 2014131232 A RU2014131232 A RU 2014131232A RU 2014131232 A RU2014131232 A RU 2014131232A
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xylene
toluic acid
ionic liquid
stream
paragraphs
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RU2014131232A
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Russian (ru)
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Алакананда Бхаттачария
Реймонд К. ШИ
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Юоп Ллк
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Priority claimed from US13/340,122 external-priority patent/US8697905B2/en
Priority claimed from US13/340,132 external-priority patent/US9085522B2/en
Application filed by Юоп Ллк filed Critical Юоп Ллк
Publication of RU2014131232A publication Critical patent/RU2014131232A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0053—Details of the reactor
    • B01J19/006—Baffles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/18—Stationary reactors having moving elements inside
    • B01J19/1862—Stationary reactors having moving elements inside placed in series
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/245—Stationary reactors without moving elements inside placed in series
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J4/00—Feed or outlet devices; Feed or outlet control devices
    • B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
    • B01J4/004—Sparger-type elements
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2204/00—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices
    • B01J2204/002—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices the feeding side being of particular interest
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/0004—Processes in series
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00042—Features relating to reactants and process fluids
    • B01J2219/00047—Ionic liquids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00101—Reflux columns
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00761—Details of the reactor
    • B01J2219/00763—Baffles
    • B01J2219/00765—Baffles attached to the reactor wall
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/02—Apparatus characterised by their chemically-resistant properties
    • B01J2219/025—Apparatus characterised by their chemically-resistant properties characterised by the construction materials of the reactor vessel proper
    • B01J2219/0277—Metal based

Abstract

1. Способ получения терефталевой кислоты, включающийсоздание потока п-ксилола, обогащенного п-толуиловой кислотой;контактирование потока п-ксилола, обогащенного п-толуиловой кислотой, растворителя, включающего ионную жидкость, источника брома, катализатора и окислителя для получения продукта, включающего терефталевую кислоту.2. Способ по п. 1, в котором создание потока п-ксилола, обогащенного п-толуиловой кислотой, включаетсоздание потока п-ксилола, включающего п-толуиловую кислоту, который получают способом, в котором поддерживают п-толуиловую кислоту на уровне по меньшей мере 5 мас.% от полученного при этом потока п-ксилола.3. Способ по п. 1, в котором создание потока п-ксилола, обогащенного п-толуиловой кислотой, включаетконтактирование п-ксилола, первого растворителя, первого источника брома, первого катализатора и первого окислителя для получения потока п-ксилола, обогащенного п-толуиловой кислотой.4. Способ по любому из пп. 1-3, в котором растворитель дополнительно включает карбоновую кислоту.5. Способ по п. 4, в котором растворитель имеет массовое отношение карбоновой кислоты к ионной жидкости в интервале от 1:16 до 16:1.6. Способ по любому из пп. 1-3, в котором катализатор включает по меньшей мере один металл, выбранный из кобальта, титана, марганца, хрома, меди, никеля, ванадия, железа, молибдена, олова, церия и циркония.7. Способ по любому из пп. 1-3, в котором ионная жидкость образуется in situ из по меньшей мере одного предшественника ионной жидкости.8. Способ по любому из пп. 1-3, в котором катион ионной жидкости образуется из имидазолов, пиразолов, тиазолов, изотиазолов, азатиазолов, оксотиазолов, оксазинов, оксазолинов, оксазаборолов, дитиозолов, триазолов, селенозолов, окса1. A method of producing terephthalic acid, comprising generating a stream of p-xylene enriched with p-toluic acid; contacting a stream of p-xylene enriched with p-toluic acid, a solvent comprising an ionic liquid, a bromine source, a catalyst and an oxidizing agent to obtain a product comprising terephthalic acid .2. The method of claim 1, wherein generating a p-xylene stream enriched with p-toluic acid comprises generating a p-xylene stream comprising p-toluic acid, which is produced by a method in which p-toluic acid is maintained at least 5 wt. % of the resulting p-xylene stream. 3. The method of claim 1, wherein generating a p-xylene stream enriched with p-toluic acid comprises contacting p-xylene, a first solvent, a first bromine source, a first catalyst and a first oxidizing agent to produce a p-xylene stream enriched with p-toluic acid. four. The method according to any one of paragraphs. 1-3, in which the solvent further comprises a carboxylic acid. 5. The method according to claim 4, in which the solvent has a mass ratio of carboxylic acid to ionic liquid in the range from 1:16 to 16: 1.6. The method according to any one of paragraphs. 1-3, in which the catalyst includes at least one metal selected from cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium and zirconium. 7. The method according to any one of paragraphs. 1-3, in which the ionic liquid is formed in situ from at least one ionic liquid precursor. The method according to any one of paragraphs. 1-3, in which the cation of the ionic liquid is formed from imidazoles, pyrazoles, thiazoles, isothiazoles, azathiazoles, oxothiazoles, oxazines, oxazolines, oxazaborols, dithiozoles, triazoles, selenozoles, oxa

Claims (10)

1. Способ получения терефталевой кислоты, включающий1. The method of obtaining terephthalic acid, including создание потока п-ксилола, обогащенного п-толуиловой кислотой;creating a stream of p-xylene enriched with p-toluic acid; контактирование потока п-ксилола, обогащенного п-толуиловой кислотой, растворителя, включающего ионную жидкость, источника брома, катализатора и окислителя для получения продукта, включающего терефталевую кислоту.contacting the p-xylene stream enriched with p-toluic acid, a solvent including an ionic liquid, a bromine source, a catalyst and an oxidizing agent to produce a product including terephthalic acid. 2. Способ по п. 1, в котором создание потока п-ксилола, обогащенного п-толуиловой кислотой, включает2. The method according to p. 1, in which the creation of a stream of p-xylene enriched with p-toluic acid includes создание потока п-ксилола, включающего п-толуиловую кислоту, который получают способом, в котором поддерживают п-толуиловую кислоту на уровне по меньшей мере 5 мас.% от полученного при этом потока п-ксилола.creating a p-xylene stream comprising p-toluic acid, which is obtained by a process in which p-toluic acid is maintained at a level of at least 5% by weight of the p-xylene stream obtained. 3. Способ по п. 1, в котором создание потока п-ксилола, обогащенного п-толуиловой кислотой, включает3. The method according to p. 1, in which the creation of a stream of p-xylene enriched with p-toluic acid includes контактирование п-ксилола, первого растворителя, первого источника брома, первого катализатора и первого окислителя для получения потока п-ксилола, обогащенного п-толуиловой кислотой.contacting p-xylene, a first solvent, a first bromine source, a first catalyst and a first oxidizing agent to produce a p-xylene stream enriched with p-toluic acid. 4. Способ по любому из пп. 1-3, в котором растворитель дополнительно включает карбоновую кислоту.4. The method according to any one of paragraphs. 1-3, in which the solvent further comprises a carboxylic acid. 5. Способ по п. 4, в котором растворитель имеет массовое отношение карбоновой кислоты к ионной жидкости в интервале от 1:16 до 16:1.5. The method according to p. 4, in which the solvent has a mass ratio of carboxylic acid to ionic liquid in the range from 1:16 to 16: 1. 6. Способ по любому из пп. 1-3, в котором катализатор включает по меньшей мере один металл, выбранный из кобальта, титана, марганца, хрома, меди, никеля, ванадия, железа, молибдена, олова, церия и циркония.6. The method according to any one of paragraphs. 1-3, in which the catalyst includes at least one metal selected from cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium and zirconium. 7. Способ по любому из пп. 1-3, в котором ионная жидкость образуется in situ из по меньшей мере одного предшественника ионной жидкости.7. The method according to any one of paragraphs. 1-3, in which the ionic liquid is formed in situ from at least one ionic liquid precursor. 8. Способ по любому из пп. 1-3, в котором катион ионной жидкости образуется из имидазолов, пиразолов, тиазолов, изотиазолов, азатиазолов, оксотиазолов, оксазинов, оксазолинов, оксазаборолов, дитиозолов, триазолов, селенозолов, оксафосфолов, пирролов, боролов, фуранов, тифенов, фосфолов, пентазолов, индолов, индолинов, оксазолов, изотиразолов, тетразолов, бензофурана, дибензофуранов, бензотиофенов, дибензотиофенов, тиадиазолов, пиридинов, пиримидинов, пиразинов, пиридазинов, пиперазинов, пиперидинов, морфолинов, пиранов, аннолинов, фталазинов, хиназолинов, хиноксалинов или их комбинаций.8. The method according to any one of paragraphs. 1-3, in which the cation of the ionic liquid is formed from imidazoles, pyrazoles, thiazoles, isothiazoles, azathiazoles, oxothiazoles, oxazines, oxazolines, oxazaborols, dithiozoles, triazoles, selenozoles, oxaphosphols, pyrroles, boroles, furans, typhenes, phosphols, indole, , indolines, oxazoles, isothirazoles, tetrazoles, benzofuran, dibenzofurans, benzothiophenes, dibenzothiophenes, thiadiazoles, pyridines, pyrimidines, pyrazines, pyridazines, piperazines, piperidines, morpholines, pyranes, annolines, quinolines, quinoline quinolines, quinolines, quinolines, quinolines, quinolines in or combinations thereof. 9. Способ по любому из пп. 1-3, в котором анион ионной жидкости представляет собой галогениды, бориды, фосфаты, арсенаты, стибаты, ацетат, карбоксилаты, азолаты, сульфаты, ацильные группы, СО3 2-; NO2 1-, NO3 1-, SO4 2-, PO4 3-, (CF3)SO3 1-, их производные или их комбинации.9. The method according to any one of paragraphs. 1-3, in which the anion of the ionic liquid is a halide, boride, phosphate, arsenate, stibate, acetate, carboxylate, azolate, sulfate, acyl group, CO 3 2- ; NO 2 1- , NO 3 1- , SO 4 2- , PO 4 3- , (CF 3 ) SO 3 1- , derivatives thereof or combinations thereof. 10. Установка для окисления алкилароматических соединений, состоящая, по существу, из10. Installation for the oxidation of alkylaromatic compounds, consisting essentially of первой реакционной зоны, имеющей по меньшей мере один впускной клапан и по меньшей мере один выпускной клапан;a first reaction zone having at least one inlet valve and at least one outlet valve; второй реакционной зоны, имеющей по меньшей мере один впускной клапан и по меньшей мере один выпускной клапан, причем по меньшей мере один впускной клапан второй реакционной зоны связан по текучей среде по меньшей мере с одним выпускным клапаном первой реакционной зоны; иa second reaction zone having at least one inlet valve and at least one outlet valve, wherein at least one inlet valve of the second reaction zone is fluidly connected to at least one outlet valve of the first reaction zone; and зоны очистки, имеющей по меньшей мере один впускной клапан и по меньшей мере один выпускной клапан, причем по меньшей мере один впускной клапан зоны очистки связан по текучей среде по меньшей мере с одним выпускным клапаном второй реакционной зоны, и по меньшей мере один выпускной клапан зоны очистки связан по текучей среде по меньшей мере с одним впускным клапаном первой реакционной зоны или по меньшей мере с одним впускным клапаном второй реакционной зоны или и с тем, и с другим. a cleaning zone having at least one inlet valve and at least one outlet valve, wherein at least one inlet valve of the cleaning zone is fluidly connected to at least one outlet valve of the second reaction zone and at least one outlet valve of the zone the purification is fluidly connected to at least one inlet valve of the first reaction zone or to at least one inlet valve of the second reaction zone or both.
RU2014131232A 2011-12-29 2012-10-18 METHOD FOR PRODUCING TERPHTHALIC ACID RU2014131232A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US13/340,122 US8697905B2 (en) 2011-12-29 2011-12-29 Process for producing terephthalic acid
US13/340,122 2011-12-29
US13/340,132 US9085522B2 (en) 2011-12-29 2011-12-29 Process for producing terephthalic acid
US13/340,132 2011-12-29
PCT/US2012/060704 WO2013101331A1 (en) 2011-12-29 2012-10-18 Process for producing terephthalic acid

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US9150485B2 (en) * 2013-10-08 2015-10-06 Uop Llc Process for controlling reaction and crystallization solvent composition in process for production of aromatic carboxylic acid
HUE059415T2 (en) * 2020-05-15 2022-11-28 Archer Daniels Midland Co Co-production of monomers, including at least one bio-based monomer

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US4334086A (en) * 1981-03-16 1982-06-08 Labofina S.A. Production of terephthalic acid
KR970000136B1 (en) * 1993-09-28 1997-01-04 브이.피. 유리예프 Process for producing highly purified benzenedicarboxylic acid isomers
US6949673B2 (en) * 2000-01-12 2005-09-27 E.I. Du Pont De Nemours And Company Process for producing carboxylic acids
KR20020069261A (en) * 2000-01-21 2002-08-29 비피 코포레이션 노쓰 아메리카 인코포레이티드 Production of high purity aromatic carboxylic acid by oxidation in benzoic acid and water solvent
GB0024745D0 (en) * 2000-10-10 2000-11-22 Univ Belfast Oxidation of alkyl-aromatic compounds
US7485746B2 (en) * 2003-11-14 2009-02-03 Bp Corporation North America Inc. Staged countercurrent oxidation
GB0422447D0 (en) * 2004-10-08 2004-11-10 Univ Cambridge Tech Use of ionic liquids
US7326808B2 (en) * 2006-03-01 2008-02-05 Eastman Chemical Company Polycarboxylic acid production system employing cooled mother liquor from oxidative digestion as feed to impurity purge system
ES2625604T3 (en) * 2006-12-21 2017-07-20 Saudi Basic Industries Corporation Process for the preparation of aromatic polycarboxylic acid by oxidation in liquid phase

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