WO2004074231A1 - 芳香族カルボン酸の製造方法 - Google Patents
芳香族カルボン酸の製造方法 Download PDFInfo
- Publication number
- WO2004074231A1 WO2004074231A1 PCT/JP2004/001549 JP2004001549W WO2004074231A1 WO 2004074231 A1 WO2004074231 A1 WO 2004074231A1 JP 2004001549 W JP2004001549 W JP 2004001549W WO 2004074231 A1 WO2004074231 A1 WO 2004074231A1
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- WO
- WIPO (PCT)
- Prior art keywords
- acetic acid
- aromatic carboxylic
- carboxylic acid
- methyl acetate
- producing
- Prior art date
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Classifications
-
- 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
Definitions
- the present invention relates to a method for producing an aromatic carboxylic acid, and more particularly to a method for producing an aromatic carboxylic acid using acetic acid as a solvent or the like during production.
- an alkyl aromatic hydrocarbon such as para-xylene is converted into an acetic acid solvent with molecular oxygen in the presence of a catalyst containing cobalt, manganese and bromine.
- a slurry containing crystals of terephthalic acid or other aromatic carboxylic acid produced by an oxidative reaction in a liquid phase is subjected to solid-liquid separation treatment, subjected to a drying step to obtain a coarse aromatic carboxylic acid, and then obtained.
- a crude aromatic carboxylic acid is dissolved in water, and this aqueous solution is purified by hydrogenation to produce a high-purity aromatic carboxylic acid.
- the method for producing such an aromatic carboxylic acid has a problem that acetic acid, which is a solvent, is consumed during the oxidation reaction, that is, acetic acid is lost during the production process.
- One of the causes is as follows. There is by-product of methyl acetate due to the heterogeneous reaction of acetic acid. Condensable components contained in the oxidizing exhaust gas generated from the reactor are condensed by a condenser to suppress the by-product of methyl acetate, and then the methyl acetate contained in the uncondensed gas is recovered by contacting and absorbing with acetic acid.
- a technique is known in which the concentration of methyl acetate in the reaction mother liquor is increased by circulating this to the reactor to suppress the by-product reaction from acetic acid to methyl acetate (see Patent Document 1). .
- the oxidized exhaust gas is directly introduced into the distillation column for distillation, and aliphatic carboxylic acid esters such as methyl acetate contained in the exhaust gas from the distillation column are brought into contact with aliphatic sulfonic acid such as acetic acid to be absorbed.
- aliphatic carboxylic acid esters such as methyl acetate contained in the exhaust gas from the distillation column are brought into contact with aliphatic sulfonic acid such as acetic acid to be absorbed.
- Patent Document 2 A method is also known in which methyl acetate contained in the distillate obtained in the solvent recovery step of dehydrating oxidized water from the acetic acid solvent is recovered by distillation and returned to the oxidation reactor.
- Patent Document 1 Japanese Patent Application Laid-Open No. 53-83493 (lower left column of page 2)
- Patent Document 2 Japanese Patent Application Laid-Open No. 2000-0727 14
- Patent Document 3 Japanese Patent Application Laid-Open No. Sho 53-3-84932
- Patent Document 4 International Publication No. 98/45 2 3 9
- methyl acetate is included in the exhaust gas mainly composed of inert gas (inert gas) after the vapor distilled by distillation in the solvent recovery step is fractionated and methyl acetate is recovered from the vapor accompanying methyl acetate. It still accompanies, and it is unclear what should be used effectively.
- an object of the present invention is to solve the above-mentioned problems, minimize the consumption of an acetic acid solvent in a process for producing an aromatic carboxylic acid, industrially increase the production efficiency, and advantageously improve terephthalic acid.
- aromatic carboxylic acids such as acids.
- an aromatic carboxylic acid is produced by producing a slurry containing an aromatic carboxylic acid by oxidizing an alkyl aromatic compound in a liquid phase using acetic acid as a solvent.
- the method for producing aromatic carboxylic acid in a step subsequent to the oxidation reaction step, is characterized in that methyl acetate contained in the generated exhaust gas is separated and collected, and the collected methyl acetate is returned to the oxidation reaction step.
- methyl acetate contained in the oxidized exhaust gas generated from the reactor recovered, but also a step subsequent to the oxidation reaction, for example, a crystallization step Since the methyl acetate contained in the exhaust gas generated in one or more steps selected from the solid-liquid separation step, the drying step and the solvent recovery step is returned to the oxidation reaction step, the by-product of methyl acetate is suppressed, The loss of acetic acid as a solvent during the reaction is reduced, and the production efficiency is improved.
- an alkyl aromatic compound is oxidized in a liquid phase to produce a slurry containing an aromatic carboxylic acid, and an aromatic carboxylic acid is produced from this slurry through at least a solid-liquid separation step.
- Acetic acid contained in the liquid or vapor generated from the oxidation reaction step or the solid-liquid separation step or both steps is recovered by distillation, and the methyl acetate in the exhaust gas generated by this distillation is recovered And then return to the oxidation reaction step to produce an aromatic carboxylic acid.
- a method of recovering methyl acetate in the exhaust gas a method of recovering methyl acetate by absorbing it in an acetic acid solution is efficient and preferable.
- the acetic acid used for collecting methyl acetate it is preferable to use acetic acid obtained by separating acetic acid and water in a solvent collecting step.
- a method for producing an aromatic carboxylic acid comprising recovering methyl acetate from the process gas and returning the acetic acid component to the oxidation reaction step.
- the acetic acid component collected as an aqueous acetic acid solution is used as a part of the solvent.
- the aqueous acetic acid solution may be used in a cake washing step in a solid-liquid separation step, or may be supplied to a solvent recovery step to reduce water content, and then reused together with other recovered acetic acid.
- water separated by separating acetic acid and water in the solvent recovery step can be used.
- para-xylene can be used as the alkyl aromatic compound in the above-described step
- terephthalic acid can be used as the aromatic carboxylic acid.
- FIG. 1 is a system diagram of an aromatic carboxylic acid production apparatus showing an embodiment of the present invention.
- 1 is a reactor
- 2 is a condenser
- 3 is an exhaust gas
- 4 is a condensate
- 5 is a crystallization tank
- 6 is a solid-liquid separator
- 7 is a solvent recovery tower
- 8 is a dehydration tower.
- Reference numeral 9 denotes a dryer
- 10 denotes a high-pressure absorption tower
- 11 denotes a low-pressure absorption tower.
- the alkyl aromatic compound used in the present invention is an alkylbenzene or alkyl such as mono-, di-, or trialkylbenzene which is converted into an aromatic carboxylic acid such as aromatic monocarboxylic acid, aromatic dicarboxylic acid, or aromatic tricarboxylic acid by liquid phase oxidation.
- aromatic carboxylic acid such as aromatic monocarboxylic acid, aromatic dicarboxylic acid, or aromatic tricarboxylic acid by liquid phase oxidation.
- Naphthalene, etc. including those in which some of the alkyl groups have been oxidized.
- the method for producing the aromatic carboxylic acid used in the present invention typically includes
- (V) a solvent recovery step of recovering acetic acid from a vapor or liquid containing acetic acid generated from at least one of the steps (i) to (iV).
- the present invention is particularly applicable to the production of terephthalic acid, and the preferred aromatic aromatic compound is para-xylene.
- the amount of acetic acid used as a solvent in the present invention is usually 2 to 6 times the weight of paraxylene as a raw material.
- the acetic acid solvent may contain a small amount of water, specifically, 15% by weight or less.
- a molecular oxygen-containing gas is used. It is usually used because air is simple equipment and can be used at low cost. Dilution air and oxygen-enriched air can also be used.
- a catalyst containing cobalt (Co), manganese '(Mn) and bromine (Br) as constituent elements is usually used as a catalyst.
- the reaction for oxidizing para-xylene in the liquid phase is performed in the presence of a catalyst in an acetic acid solvent, in the range of 140 to 230. C., preferably at 150 to 210 ° C., by oxidizing para-xylene while continuously supplying a molecular oxygen-containing gas.
- the pressure in the oxidation reaction step is a pressure at which the mixture can maintain a liquid phase at least at the reaction temperature or higher, and is usually 0.2 to 5 MPa, preferably 1 to 2 MPa.
- the reactor is usually a tank equipped with a stirrer, but the stirrer is not always necessary and may be a bubble column type.
- a cooler is provided at the upper part of the reactor, and a gas supply port containing molecular oxygen is provided at the lower part. Then, the molecular oxygen-containing gas supplied from the lower part is used for the oxidation reaction, is extracted from the reactor as an exhaust gas accompanied by a large amount of solvent vapor, and is then condensed from the exhaust gas in a reflux cooler. After being condensed and separated, it is discharged as oxidizing exhaust gas. Part of the condensate is purged out of the system to control the water content of the reaction mother liquor, and the rest is returned to the reactor.
- the oxidized exhaust gas is introduced into a high-pressure absorption tower, and the methyl acetate in the exhaust gas is absorbed by gas-liquid contact with acetic acid or a liquid containing acetic acid.
- acetic acid it is preferable to use acetic acid recovered from the solvent recovery step.
- the acetic acid that has absorbed methyl acetate in this way is returned to the oxidation reactor and subjected to the oxidation reaction, and is used for the terephthalic acid generation reaction.
- a crystallization step for a slurry of the reaction product obtained in the oxidation reaction step the reaction slurry is lowered to an appropriate temperature and pressure to obtain a terephthalic acid slurry.
- the crystallization conditions are 1 to 6 crystallization stages, and preferably 2 to 4 crystallization stages.
- a series of crystallization steps employ flash cooling, and the final step is preferably performed under reduced pressure boiling.
- Terephthalic acid is usually recovered from the crystallized slurry through a solid-liquid separation step and a drying step, and sent to the hydrogenation purification step.
- the drying step is omitted, and the acetic acid solvent is passed through a solvent replacement step. May be replaced with an aqueous solvent, and sent directly to the hydrorefining step.
- a device for performing solid-liquid separation a device such as a centrifuge, a horizontal belt filter, a rotary vacuum filter, or the like is generally used, but is not limited thereto.
- the solvent recovery step is a step of purifying the condensate of the oxidized exhaust gas and the mother liquor separated at the time of solid-liquid separation to recover acetic acid.Since the water produced by oxidation is removed, the solvent recovery step is also referred to as the acetic acid dehydration step. Is done.
- exhaust gas containing methyl acetate and acetic acid generated in each step must be used. Aggregate at least one of the above into a collected gas, which is absorbed It can be carried out by introducing the acetic acid into a droplet and guiding it to a tower to absorb the acetic acid. This absorption condition is preferably as low as possible from the viewpoint of absorption efficiency, and is usually carried out at 50 ° C or lower.
- a liquid containing water is added to crude terephthalic acid to form a slurry, which is heated and dissolved, and then subjected to hydrogenation treatment in the presence of a catalyst.
- This is a method for producing high-purity terephthalic acid by performing liquid separation.
- the crude terephthalic acid is usually supplied to the hydrogenation reaction system as a slurry of 20 to 35 % by weight / 0 with respect to the liquid containing water.
- any known catalyst can be used, and examples thereof include palladium, ruthenium, rhodium, osmium, iridium, and platinum supported on activated carbon. These catalysts may be used in combination.
- the conditions for the hydrorefining reaction are usually as follows: a reaction temperature of 255 to 300 ° C, a reaction pressure of 1 to 12 MPa, and a hydrogen partial pressure of 0.05 to 3 MPa. Is common, but is not limited to this.
- Terephthalic acid purified by a hydrogenation reaction is generally separated as a solid by crystallization and solid-liquid separation.
- the crystallization conditions are selected in consideration of the yield of the solids to be precipitated, the purity of the solids, etc.
- the crystallization is carried out in a plurality of stages, and the crystallization conditions in the final stage are as follows. 40 to 180 ° C, 0.3 to 1. OMPa. At this time, the residence time in each crystallization tank is about 5 to 200 minutes. If the temperature of the crystallization tank in the final stage is lower than the above range, the precipitation amount of impurities such as p-TA rapidly increases, which is not preferable because the purity of terephthalic acid separated as a solid content is low.
- terephthalic acid precipitated in the crystallization step is separated from a liquid whose main component is water.
- the temperature and pressure conditions for the solid-liquid separation are generally selected to be substantially the same as the above-mentioned conditions for the crystallization tank, and when the crystallization process is performed in multiple stages, the conditions for the final crystallization tank.
- a device for performing solid-liquid separation a device such as a centrifuge, a horizontal belt filter, a rotary vacuum filter, or the like is generally used, but is not limited thereto. Also, these It is also possible to use two or more devices in combination.
- Terephthalic acid obtained by separating solids precipitated after the purification step by solid-liquid separation may be dried as it is to obtain a product, or after slurrying with fresh water in a suspension washing tank, washing, and then solidifying.
- the solid content separated by liquid separation may be dried to obtain a product.
- a reactor also referred to as an oxidation reactor
- a reactor 1 is supplied with a mixture of a catalyst containing Co / Mn / Br, an acetic acid solvent, and a raw material xylene, and a molecular oxygen-containing gas.
- the gas component extracted from the reactor 1 is condensed and separated from condensable components such as acetic acid in a condenser (gas-liquid separator) 2 and then discharged from the heat exchanger 2 as oxidized exhaust gas.
- a part of the condensate 4 is discharged out of the system as a purge for water control, and then refluxed to the reactor 1.
- the slurry obtained by the oxidation treatment in the reactor 1 is transferred to a low-temperature re-oxidation tank (not shown), and is oxidized at a lower temperature than the reactor 1 by a small amount of molecular oxygen-containing gas.
- the oxidized slurry is further crystallized in the crystallization tank 5.
- the number of crystallization stages is usually 1 to 6 stages.
- the slurry subjected to the crystallization treatment is separated into a mother liquor component and a crude terephthalic acid cake by a solid-liquid separator 6, and a crude terephthalic acid is obtained via a dryer 9.
- the crude terephthalic acid is converted into a slurry with water-containing liquid in a mixing tank (not shown), and after dissolution, transferred to a hydrogenation and purification reactor where it is purified and processed into high-purity terephthalic acid.
- the oxidized exhaust gas condensate and the mother liquor component separated by the solid-liquid separator 6 are transferred to a solvent recovery step having a solvent recovery tower 7 and a dehydration tower 8, and acetic acid is recovered.
- Exhaust gas 3 is discharged not only from the reactor 1, but also from the crystallization tank 5, the solid-liquid separator 6, the dryer 9, and the dehydration tower 8.
- Exhaust gas composed of such an aggregate of one or more local exhaust gases is introduced into the high-pressure absorption tower 10 or the low-pressure absorption tower 11 and is entrained in the exhaust gas using acetic acid as an absorbing solution. Absorb methyl acetate and collect in reactor 1.
- an inert gas such as a process gas is passed through the drier so that the solvent component evaporated in the drier accompanies the gas and goes out of the drier.
- a means for discharging since the gas contains methyl acetate, it is preferable to apply the means for collecting methyl acetate of the present invention.
- acetic acid obtained by separating acetic acid and water in the solvent recovery step (7 and 8) is preferable. Further, it is preferable to provide a device for absorbing and recovering acetic acid using water on the downstream side of the high-pressure absorption tower 10 and the low-pressure absorption tower 11.
- the methyl acetate absorption device and the acetic acid absorption device may be separate towers, or may be provided integrally with the same tower.
- the water used for acetic acid absorption at this time was water obtained by separating acetic acid and water in the solvent recovery step (7 and 8) or solid-liquid separation in the hydrogenation purification step. A separation mother liquor containing water as a main component is preferred.
- methyl acetate is produced from the exhaust gas of the aggregate of the exhaust gas containing methyl acetate generated in one or more steps selected from the crystallization step, the solid-liquid separation step, the drying step and the solvent recovery step.
- a by-product reaction of methyl acetate is suppressed, loss of acetic acid as a solvent during the reaction is reduced, and production efficiency is improved.
- the present invention not only recovers the methyl acetate contained in the oxidized exhaust gas generated from the reactor, but also performs the steps subsequent to the oxidation reaction step, ie, the crystallization step and the solid-liquid separation step.
- methyl acetate obtained from exhaust gas generated in one or more steps selected from the drying step and the solvent recovery step is also returned to the oxidation reaction step, so that the recovery efficiency of methyl acetate is increased,
- the loss of acetic acid as a solvent therein is reduced and the production efficiency is improved.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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AU2004213274A AU2004213274A1 (en) | 2003-02-21 | 2004-02-13 | Process for producing aromatic carboxylic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2003-044121 | 2003-02-21 | ||
JP2003044121 | 2003-02-21 |
Publications (1)
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WO2004074231A1 true WO2004074231A1 (ja) | 2004-09-02 |
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PCT/JP2004/001549 WO2004074231A1 (ja) | 2003-02-21 | 2004-02-13 | 芳香族カルボン酸の製造方法 |
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CN (1) | CN100402482C (ja) |
AU (1) | AU2004213274A1 (ja) |
WO (1) | WO2004074231A1 (ja) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100368370C (zh) * | 2006-03-29 | 2008-02-13 | 中国石化仪征化纤股份有限公司 | 对二甲苯氧化母液中悬浮物的回收系统装置 |
US7863481B2 (en) | 2006-03-01 | 2011-01-04 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7880032B2 (en) | 2006-03-01 | 2011-02-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7888530B2 (en) | 2004-09-02 | 2011-02-15 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
US7897810B2 (en) | 2004-09-02 | 2011-03-01 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
US7897808B2 (en) | 2006-03-01 | 2011-03-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7956215B2 (en) | 2006-03-01 | 2011-06-07 | Grupo Petrotemex, S.A. De C.V. | Versatile oxidation byproduct purge process |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101914003A (zh) * | 2010-07-02 | 2010-12-15 | 逸盛大化石化有限公司 | 一种烷基芳香烃液相催化氧化生产芳香族羧酸的方法 |
GB201417621D0 (en) * | 2014-10-06 | 2014-11-19 | Invista Tech Sarl | Production of an aromatic dicarboxylic acid |
GB201417735D0 (en) * | 2014-10-07 | 2014-11-19 | Invista Tech Sarl | Production of an aromatic dicarboxylic acid |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5384932A (en) * | 1976-12-30 | 1978-07-26 | Mitsubishi Chem Ind Ltd | Preparation of terephthalic acid |
JP2000072714A (ja) * | 1998-08-24 | 2000-03-07 | Mitsui Chemicals Inc | 芳香族カルボン酸の製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1088561A (en) * | 1976-12-30 | 1980-10-28 | Hiroshi Hashizume | Process for producing terephthalic acid |
KR20000005733A (ko) * | 1998-06-05 | 2000-01-25 | 나까니시 히로유끼 | 방향족카복실산의제조방법 |
US6143926A (en) * | 1999-09-21 | 2000-11-07 | E. I. Du Pont De Nemours And Company | Process for producing pure terephthalic acid with improved recovery of precursors, solvent and methyl acetate |
-
2004
- 2004-02-13 WO PCT/JP2004/001549 patent/WO2004074231A1/ja active Application Filing
- 2004-02-13 CN CNB2004800045914A patent/CN100402482C/zh not_active Expired - Lifetime
- 2004-02-13 AU AU2004213274A patent/AU2004213274A1/xx active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5384932A (en) * | 1976-12-30 | 1978-07-26 | Mitsubishi Chem Ind Ltd | Preparation of terephthalic acid |
JP2000072714A (ja) * | 1998-08-24 | 2000-03-07 | Mitsui Chemicals Inc | 芳香族カルボン酸の製造方法 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7888530B2 (en) | 2004-09-02 | 2011-02-15 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
US7897810B2 (en) | 2004-09-02 | 2011-03-01 | Eastman Chemical Company | Optimized production of aromatic dicarboxylic acids |
US7959879B2 (en) * | 2004-09-02 | 2011-06-14 | Grupo Petrotemex, S.A. De C.V. | Optimized production of aromatic dicarboxylic acids |
US7863481B2 (en) | 2006-03-01 | 2011-01-04 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7880032B2 (en) | 2006-03-01 | 2011-02-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7897808B2 (en) | 2006-03-01 | 2011-03-01 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7902395B2 (en) | 2006-03-01 | 2011-03-08 | Eastman Chemical Company | Versatile oxidation byproduct purge process |
US7956215B2 (en) | 2006-03-01 | 2011-06-07 | Grupo Petrotemex, S.A. De C.V. | Versatile oxidation byproduct purge process |
CN100368370C (zh) * | 2006-03-29 | 2008-02-13 | 中国石化仪征化纤股份有限公司 | 对二甲苯氧化母液中悬浮物的回收系统装置 |
Also Published As
Publication number | Publication date |
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CN100402482C (zh) | 2008-07-16 |
CN1751015A (zh) | 2006-03-22 |
AU2004213274A1 (en) | 2004-09-02 |
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