WO2011001891A1 - (メタ)アクリル酸の製造方法 - Google Patents
(メタ)アクリル酸の製造方法 Download PDFInfo
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- WO2011001891A1 WO2011001891A1 PCT/JP2010/060749 JP2010060749W WO2011001891A1 WO 2011001891 A1 WO2011001891 A1 WO 2011001891A1 JP 2010060749 W JP2010060749 W JP 2010060749W WO 2011001891 A1 WO2011001891 A1 WO 2011001891A1
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- acrylic acid
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
- B01D9/0013—Crystallisation cooling by heat exchange by indirect heat exchange
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/004—Fractional crystallisation; Fractionating or rectifying columns
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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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
Definitions
- the present invention relates to a method for producing (meth) acrylic acid.
- (Meth) acrylic acid is generally obtained by conducting a (meth) acrylic acid-containing gas obtained by catalytic gas phase oxidation reaction to a condensing tower or a collecting tower to obtain a crude (meth) acrylic acid solution, which is further purified. Manufactured. As such a purification method, crystallization is used in addition to distillation, diffusion, extraction and the like.
- the (meth) acrylic acid-containing gas obtained by the catalytic gas phase oxidation reaction is mixed with other components such as acetic acid and dimer in addition to the raw material compound. Therefore, it is difficult to obtain (meth) acrylic acid having a sufficiently high purity by a single purification, and it is necessary to combine purification by various means or repeat the same purification means.
- Patent Documents 1 and 2 acrylic acid or the like is crystallized and purified multiple times.
- a tank corresponding to each crystallization purification stage is provided, and a compound stored in each tank is used as a raw material for the next stage of crystallization.
- the crystallizer is more complex and expensive than the tank, so the number of crystallizers is usually the same as the number of crystallizations. I don't mean.
- Patent Documents 1 and 2 do not describe any specific operating conditions of the crystallizer for efficient crystallization purification.
- crystallization purification it is common not only to crystallize (meth) acrylic acid but also to melt crystals obtained from the ease of transport. That is, in the crystallizer, both cold heat for crystallizing (meth) acrylic acid from a crude (meth) acrylic acid solution and warm heat for melting (meth) acrylic acid crystals are required.
- an object of the present invention is to provide a method for producing (meth) acrylic acid in which production efficiency is improved by efficiently switching from heating to cooling in a crystallizer.
- the inventors of the present invention have made extensive studies to solve the above problems.
- switching from the heating medium necessary for melting the (meth) acrylic acid crystals to the cooling medium necessary for crystallizing the (meth) acrylic acid is performed from the crystallizer.
- the present invention has been completed by discovering that the transition from the melting step to the crystallization step can be quickly carried out by starting during the transfer of the liquid.
- the method for producing (meth) acrylic acid according to the present invention uses a batch crystallizer to crystallize a crude (meth) acrylic acid solution and melt the obtained (meth) acrylic acid crystal. Including a step; while the (meth) acrylic acid melt is being transferred from the crystallizer, precooling of the crystallizer is started for the next crystallization step.
- FIG. 1 is a diagram schematically showing a crystallizer and its peripheral equipment for carrying out the method for producing (meth) acrylic acid according to the present invention.
- 1 indicates a crystallizer
- 2 indicates a crystallization tube
- 3 indicates a crude (meth) acrylic acid supply port
- 4 indicates a heat medium supply port
- 5 indicates a heat medium discharge port.
- 6 indicates a circulation supply pump
- 7 indicates a valve
- 8 indicates an intermediate storage tank
- 9 indicates a transfer pump
- 10 indicates a valve
- 11 indicates a line to the mother liquor tank of each crystallization purification stage.
- 12 indicates a valve
- 13 indicates a line to the (meth) acrylic acid tank of each crystallization purification stage.
- the method of the present invention includes a step of crystallizing a crude (meth) acrylic acid solution using a batch crystallizer.
- the crude (meth) acrylic acid solution is not particularly limited as long as it contains impurities in addition to the target compound (meth) acrylic acid.
- a crude (meth) acrylic acid solution obtained by bringing a (meth) acrylic acid-containing gas obtained by a catalytic gas phase oxidation reaction into contact with a collection liquid or condensing can be mentioned.
- the crude (meth) acrylic acid solution obtained by bringing the (meth) acrylic acid-containing gas into contact with the collection liquid or condensing includes water, acetic acid, propionic acid in addition to (meth) acrylic acid and unreacted raw materials.
- By-product impurities such as maleic acid, acetone, acrolein, furfural and formaldehyde are contained.
- the melt of (meth) acrylic acid once obtained through crystallization purification may be supplied to the crystallizer, and the crystallization purification may be repeated. . That is, in the present invention, crystallization purification may be repeated twice or more. In the present invention, even if (meth) acrylic acid that has undergone crystallization purification once or more is supplied to a crystallizer for further crystallization purification, crude (meth) acrylic acid is used for convenience. Let's say.
- (meth) acrylic acid is crystallized and purified using a crystallizer, but the type of crystallizer is not particularly limited.
- the purpose of the present invention is to efficiently shift from the melting step to the crystallization step in the same crystallizer, both crystallization of (meth) acrylic acid and melting of the crystal can be performed.
- a crystallizer is used.
- a crystallizer that has a heat transfer surface and can crystallize or melt (meth) acrylic acid by heat exchange on the heat transfer surface can be mentioned.
- the inside of the crystallizer includes a portion to which a cooling medium or a heating medium is supplied (a heating medium existing portion), a crude (meth) acrylic acid solution and / or a (meth) acrylic acid crystal by a heat transfer surface. It is preferably divided into existing portions (crystallized product existing portions). In such a crystallizer, so-called dynamic crystallization can be performed in which the crude (meth) acrylic acid solution is crystallized while flowing down the heat transfer surface.
- (meth) acrylic acid is crystallized from the crude (meth) acrylic acid solution in the crystallization process and crystallized in the melting process by heat exchange on the heat transfer surface.
- (Meth) acrylic acid is melted.
- a cooling medium is supplied to the crystallizer, and a (meth) acrylic acid-containing solution is supplied to the crystallizer, and the crude (meth) acrylic is supplied by the cooling medium via the heat transfer surface.
- the acid solution is cooled and (meth) acrylic acid crystallizes.
- a heating medium is supplied to the crystallizer, and the crystallized (meth) acrylic acid itself is heated by the heating medium via the heat transfer surface, or (meth) acrylic acid that is circulated and supplied. Thaw by being heated by the heat of the melt.
- a device generally used as a heat exchanger can be adopted, and it is particularly preferable to employ a device used as a heat exchanger that performs heat exchange between liquids.
- a plate-type heat exchanger in which one plate is arranged, or a plurality of plates are laminated at intervals, and a heat medium existence part and a crystallized substance existence part are alternately arranged via the plates;
- a multi-tube type (shell and tube type) heat exchanger in which the tubes are arranged in a container and exchange heat inside and outside the tube; the inner tube is placed inside the outer tube, and heat is exchanged inside and outside the inner tube.
- a double pipe heat exchanger or the like that performs the exchange can be employed.
- the cross-sectional shape of the tube used in the multi-tube heat exchanger or the double tube heat exchanger is not particularly limited.
- a static crystallizer manufactured by BEFSPROKEEM (France) or a dynamic crystallizer manufactured by Sulzer Chemtech (Switzerland) can be used.
- a dynamic crystallizer is used because crystals and mother liquor can be easily separated.
- the method of the present invention can be suitably applied to a method (Falling Film type) in which a crude (meth) acrylic acid solution is circulated and fed to a crystallizer in a batch manner, and crystallization is performed while flowing into a falling film.
- the melting point of acrylic acid is 13.5 ° C., and the melting point of methacrylic acid is 16 ° C.
- the freezing point of (meth) acrylic acid is lower than these melting points, but by sufficiently cooling, (meth) acrylic acid is crystallized.
- This cooling may be performed in stages. That is, it can be said that the purity of the crystal of the compound is higher when the time is obtained at a relatively high temperature than when it is obtained in a short time at a relatively low temperature. It is also known that if the crystal purity at the initial stage of crystallization is increased, the purity of crystals grown thereafter can also be increased. Therefore, the cooling temperature of the crude (meth) acrylic acid solution in the initial stage of crystallization can be made relatively high, and after obtaining crystals with high purity, the cooling temperature can be lowered to grow the crystals sufficiently.
- the (meth) acrylic acid crystals and the solution (mother liquor) are separated.
- the dynamic crystallizer dynamic crystallization occurs on the heat transfer surface, and the crystal grows on the heat transfer surface, whereas the solution (mother liquor) is discharged from the heat transfer surface.
- (Meth) acrylic acid obtained by the crystallization process is subjected to a melting process.
- This melting step is for making (meth) acrylic acid liquid and facilitating the transfer or discharging the crystal from the crystallizer, but a sweating operation may be optionally performed to increase the purity.
- the amount of impurities present in the solution relatively increases as crystallization of (meth) acrylic acid proceeds, and thus impurities may adhere to the surface of (meth) acrylic acid crystals. . Therefore, the purity of the crystal can be increased by partially melting the surface of the (meth) acrylic acid crystal and discharging the melted portion. Such a partial melting process is called a sweating operation.
- the temperature of the heating medium is set to be equal to or higher than the melting point of (meth) acrylic acid, about 1% by mass to 10% by mass of the crystal is melted, and the melt is discharged. Good.
- the circulation of the mother liquor is stopped so that impurities do not further adhere to the (meth) acrylic acid crystal.
- the degree of crystal melting can be estimated from, for example, the increment of the liquid in the reservoir of the crystallizer.
- the partial melt obtained by the sweating operation is combined with the mother liquor of the crystallization process and mixed with crude (meth) acrylic acid for the crystallization process when crystallization purification before the same stage (the same number of times) is performed separately.
- the crystallization process is performed by mixing with crude (meth) acrylic acid in the case where the crystallization purification is performed once less than the same stage.
- the mother liquor of a crystallization process will accumulate in the storage part of the lower part of the crystallizer 1.
- FIG. 1 When the sweating operation is performed, the partial melt also accumulates in the storage part.
- the mixture of the mother liquor and the partial melt is transferred to the intermediate storage tank 8 by opening the valve 7. Further, by opening the valve 10 and operating the pump 9, the mixture is transferred to the mother liquor tank of each crystallization purification stage. Since the mixture contains (meth) acrylic acid, the yield can be improved by mixing with crude (meth) acrylic acid and separately performing crystallization purification.
- the mother liquor and / or partial melt is completely discharged from the crystallizer, and then the temperature of the heating medium is raised to completely remove the (meth) acrylic acid crystals. Melt. Such melting may be performed by warming the (meth) acrylic acid crystal to the melting point or higher. Similarly to the crystallization process, it is possible to use a plurality of heating media each having a different temperature and to carry out the melting process step by step. In the melting step, a melt of (meth) acrylic acid may be circulated and supplied. By supplying the melt to the crystallization tube, it is possible to accelerate the melting of the crystals by the heat.
- the (meth) acrylic acid crystals present in the crystallization tube 2 are completely melted, and the molten liquid is accumulated in the storage section below the crystallizer 1.
- the melt is transferred to the intermediate storage tank 8 by opening the valve 7. Further, by opening the valve 12 and operating the pump 9, the mixture is transferred to the (meth) acrylic acid tank of each crystallization purification stage. If the purity is not sufficient, the (meth) acrylic acid may be used as crude (meth) acrylic acid in a further crystallization purification stage. If the purity is sufficient, the product may be used as it is.
- crystallization purification described above may be repeated twice or more in order to obtain higher purity (meth) acrylic acid.
- crystallization purification can be performed once or more and 6 times or less, more preferably 2 times or more and 5 times or less, and further preferably 3 times or more and 5 times or less.
- the purity of (meth) acrylic acid is improved, and the concentration of the polymerization inhibitor added when the solution is collected or condensed from the (meth) acrylic acid-containing gas. Is lowered by crystallization purification, so that the polymerization becomes easier.
- the possibility of polymerization is increased by heating in the melting step. Therefore, it is preferable to use a polymerization inhibitor in the melting step.
- polymerization inhibitors examples include N-oxyl compounds such as 2,2,6,6-tetramethylpiperidino-1-oxyl; phenol compounds such as p-methoxyphenol; manganese salt compounds such as manganese acetate; dibutyldithiocarbamic acid Examples thereof include dialkyldithiocarbamate compounds such as copper; nitroso compounds; amine compounds; phenothiazine compounds.
- N-oxyl compounds such as 2,2,6,6-tetramethylpiperidino-1-oxyl
- phenol compounds such as p-methoxyphenol
- manganese salt compounds such as manganese acetate
- dibutyldithiocarbamic acid examples thereof include dialkyldithiocarbamate compounds such as copper; nitroso compounds; amine compounds; phenothiazine compounds.
- a polymerization inhibitor may be used only 1 type and may use 2 or more types together.
- the polymerization inhibitor may be added directly to a (meth) acrylic acid melt or the like, or the solution may be added.
- the solvent of the solution (meth) acrylic acid solution, water, acetic acid and the like can be used, and among these, (meth) acrylic acid solution is preferable.
- the (meth) acrylic acid purified at each crystallization purification stage is crystallized in a tank according to the stage before performing another crystallization purification. Must be transferred from the vessel. However, this transfer takes time, especially in industrial mass production.
- crystallization purification is repeatedly performed. More specifically, crystallization purification at the same stage may be repeated, or crystallization purification at different stages may be performed. In any case, the crystallization process and the melting process are alternately performed in one crystallizer. Therefore, it is necessary to alternately cool and heat the crystallizer. Conventionally, however, no effort has been made to efficiently switch between cooling and heating.
- the melt obtained by heating the (meth) acrylic acid crystal in the melting step is transferred from the crystallizer to the storage tank, it is crystallized for the next crystallization step.
- Start pre-cooling of the device That is, even after the melting of the (meth) acrylic acid crystals is completely completed, the heating medium for heating remains in the crystallizer immediately after that. Therefore, even if the heating medium is switched to the cooling medium for the next crystallization step and the supply of the cooling medium to the crystallizer is started, the crystallizer is not immediately cooled.
- the heat medium temperature and the heat medium discharge at the heat medium supply port of the crystallizer are used because of the remaining hot medium and residual heat.
- the heat medium temperature at the outlet is greatly different.
- the temperature of the heat medium at the heat medium outlet continues to decrease due to the supply of the cold medium, it takes time to stabilize.
- the production efficiency is improved by providing a time for transferring the (meth) acrylic acid melt from the crystallizer and cooling the crystallizer in parallel.
- pre-cooling refers to starting cooling of the crystallizer before introducing the crude (meth) acrylic acid into the crystallizer for the crystallization process, and the temperature at the start of the next crystallization. It means that the temperature is lowered to about the heat medium temperature. More specifically, after completion of the melting process, the heating medium supplied to the crystallizer for the next crystallization process is switched from the heating medium to the cooling medium, and the temperature of the cooling medium introduced into the crystallizer is crystallized. It means that the temperature is about the same as the temperature of the supply cooling heat medium for the crystallization process, preferably within ⁇ 5 ° C. of the temperature of the supply cooling heat medium for the crystallization process. In addition, since there is no (meth) acrylic acid solution or crystals in the crystallization tube between the melting step and the crystallization step, the heating medium temperature at the heating medium supply port is almost equal to the temperature of the crystallizer. Can be considered.
- the transfer of the (meth) acrylic acid melt from the crystallizer is completed before the pre-cooling is completed. That is, the pre-cooling of the crystallizer is started for the next crystallization process while the (meth) acrylic acid melt is being transferred from the crystallizer, and the pre-cooling is completed before the (meth) acrylic is completed.
- the transfer of the acid melt from the crystallizer is completed, and the supply of crude (meth) acrylic acid as a raw material for the next crystallization process to the crystallizer reservoir is started.
- the next crystallization process can be efficiently started by starting the circulation supply of the crude (meth) acrylic acid in the crystallizer reservoir immediately after the pre-cooling is completed.
- a circulation feed i.e. a crystallization process, may be started.
- the crystallizer is precooled.
- pre-cooling is started when 90% or less of the (meth) acrylic acid melt is transferred from the crystallizer, the transition from the melting step to the crystallization step can be performed sufficiently efficiently.
- pre-cooling is started when the ratio is less than 50%, the introduction of the crude (meth) acrylic acid solution into the crystallizer immediately after the transfer of the (meth) acrylic acid melt from the crystallizer is completed.
- the crystallizer reservoir has not been introduced with sufficient crude (meth) acrylic acid solution to circulate and the process from the melting step to the crystallization step There is a possibility that the migration cannot be performed efficiently.
- the time for transferring the melt and the precooling of the crystallizer is provided in parallel, and the blank time when shifting from the melting process to the crystallization process in the crystallizer is reduced as much as possible. This makes it possible to increase the production efficiency of (meth) acrylic acid.
- Example 1 Production of crude acrylic acid solution Propylene is subjected to a catalytic gas phase oxidation reaction in a reactor, and the resulting reaction gas is introduced into a collection tower and brought into contact with the collection liquid. A crude acrylic acid solution was obtained. When the obtained crude acrylic acid solution was analyzed, 90.0% by mass of acrylic acid, 3.2% by mass of water, 1.9% by mass of acetic acid, 0.6% by mass of maleic acid, 1.5% of acrylic acid dimer It contained 0.07% by mass of furfural, 0.07% by mass of furfural, 0.06% by mass of formaldehyde, 0.1% by mass of hydroquinone, and 2.3% by mass of other impurities. Further, the temperature at the bottom of the collection tower at this time, that is, the temperature of the crude acrylic acid solution immediately after being taken out from the collection tower was 91 ° C.
- the temperature of the crude acrylic acid solution was adjusted to about 25 ° C. with a heat exchanger, and then supplied to the reservoir of the crystallizer 1 schematically shown in FIG. More specifically, the crystallizer 1 is configured so that a crude acrylic acid solution can be circulated and supplied from the reservoir to the upper part by a circulation supply pump 6.
- the pipe for circulating supply is a metal pipe having a length of 6 m and an inner diameter of 70 mm.
- the crude acrylic acid solution supplied to the upper part falls on the inner wall of the crystallization tube 2 in the form of a film.
- the surface of the crystallization tube 2 is composed of a double jacket, and the temperature is controlled by the heat medium supplied from the heat medium supply port 4 and discharged from the heat medium discharge port 5.
- the crude acrylic acid that has passed through the crystallization tube 2 is once stored in the storage section and then continuously circulated and supplied to the upper part.
- the circulation supply pump 6 was stopped, the heating medium was switched to the heating medium, and about 2 to 5% by mass of the crystals were sweated.
- the amount of sweat was estimated from the increment of the crude acrylic acid solution in the reservoir.
- the valve 7 was opened, the perspiration liquid in the reservoir and the mother liquor at the time of crystallization were transferred to the intermediate storage tank 8, and the valve 12 was further opened to be transferred to the first mother liquid tank.
- melt was circulated and supplied to the upper part of the crystallizer 1 by the pump 6, and the melting of the crystals was promoted by flowing down on the acrylic acid crystals in the crystallizer.
- the valve 7 was opened, and the transfer of the melt present in the reservoir to the intermediate storage tank 8 was started.
- the hot medium supplied to the crystallizer 1 was switched to the cold medium, and the transfer of the melt and the cooling of the crystallization tube 2 were performed in parallel.
- the purity of acrylic acid was 99.94% by mass, and in addition, water 94 mass ppm, acetic acid 440 mass ppm, maleic acid 2 mass ppm, and acrylic acid dimer 47 mass. It contained ppm, furfural 0.2 mass ppm, benzaldehyde 0.1 mass ppm, and no formaldehyde was detected.
- the production efficiency from the first crystallization purification to the fourth crystallization purification was 3.68 kg / hour.
- the purity of acrylic acid was 99.94% by mass, and in addition, 92 mass ppm of water, 460 mass ppm of acetic acid, 2 mass ppm of maleic acid, 51 mass of acrylic acid dimer. It contained ppm, furfural 0.3 mass ppm, benzaldehyde 0.2 mass ppm, and no formaldehyde was detected.
- the production efficiency from the first crystallization purification to the fourth crystallization purification was 3.32 kg / hour.
- the transition from the melting step to the crystallization step can be accelerated.
- the method of the present invention is extremely useful industrially as it can improve the production efficiency of (meth) acrylic acid.
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Abstract
Description
(1) 粗アクリル酸溶液の製造
反応器内でプロピレンを接触気相酸化反応に付し、得られた反応ガスを捕集塔に導入して捕集液と接触させ、捕集塔の塔底より粗アクリル酸溶液を得た。得られた粗アクリル酸溶液を分析したところ、アクリル酸90.0質量%、水3.2質量%、酢酸1.9質量%、マレイン酸0.6質量%、アクリル酸二量体1.5質量%、フルフラール0.07質量%、ベンズアルデヒド0.27質量%、ホルムアルデヒド0.06質量%、ハイドロキノン0.1質量%、その他の不純物2.3質量%を含んでいた。また、このときの捕集塔塔底温度、即ち捕集塔より取り出された直後における粗アクリル酸溶液の温度は、91℃であった。
上記晶析器へ、冷熱媒を供給し、晶析器1の熱媒供給口4付近における冷熱媒の温度が結晶化工程の開始温度の±5℃以内となった後、貯留部の粗アクリル酸溶液の循環供給を開始した。貯留部における粗アクリル酸溶液量から晶析管2の内壁に晶析した結晶の量を推定し、原料粗アクリル酸溶液に含まれる粗アクリル酸の約60~90質量%が結晶化するまで循環を継続した。
晶析器1から全ての融解液の移送を完了させてから直ぐに、第1アクリル酸タンクのアクリル酸の全量を上記晶析器1へ供給し、上記第1晶析精製と同様に晶析精製を行った後、アクリル酸を第2アクリル酸タンクへ移送した。なお、熱媒供給口4付近における冷熱媒の温度が結晶化工程の開始温度の±5℃以内になった時点において、晶析器1の貯留部には十分量の粗アクリル酸がたまっており、速やかに粗アクリル酸の循環供給を開始することができ、第2晶析精製へ効率的に移行することが可能であった。
晶析器1から全ての融解液の移送を完了させてから直ぐに、第2アクリル酸タンクのアクリル酸の全量を上記晶析器1へ供給し、上記第1晶析精製と同様に晶析精製を行った。但し、融解工程においては、重合防止剤であるp-メトキシフェノールの5質量%アクリル酸溶液を晶析器1の貯留部へ投入し、晶析管中のアクリル酸結晶上を流下させた。得られたアクリル酸を第3アクリル酸タンクへ移送した。
晶析器1から全ての融解液の移送を完了させてから直ぐに、第3アクリル酸タンクのアクリル酸の全量を上記晶析器1へ供給し、上記第3晶析精製と同様の条件で晶析精製を行った後、アクリル酸を第4アクリル酸タンクへ移送した。
第1晶析精製後、晶析器1内のアクリル酸の全量を中間貯留タンク8へ移送してから、晶析器1へ供給する温熱媒を冷熱媒に切り替えて晶析管2の冷却を開始した以外は上記実施例1と同様にして、アクリル酸を精製した。
Claims (3)
- (メタ)アクリル酸を製造するための方法であって;
回分式の晶析器を用いて、粗(メタ)アクリル酸溶液を結晶化する工程と、得られた(メタ)アクリル酸結晶を融解する工程を含み;
(メタ)アクリル酸融解液を晶析器から移送している間に、次の結晶化工程のために晶析器の事前冷却を開始することを特徴とする(メタ)アクリル酸の製造方法。 - 事前冷却が完了するまでに、(メタ)アクリル酸融解液の晶析器からの移送を完了させる請求項1に記載の製造方法。
- 融解工程後、得られた(メタ)アクリル酸融解液の50%以上、90%以下が晶析器から移送された時点で晶析器の事前冷却を開始する請求項1または2に記載の製造方法。
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CN201080026408.6A CN102471212B (zh) | 2009-07-01 | 2010-06-24 | (甲基)丙烯酸的制备方法 |
US13/377,273 US8680331B2 (en) | 2009-07-01 | 2010-06-24 | Process for production of (meth)acrylic acid |
EP10794060.3A EP2450338B1 (en) | 2009-07-01 | 2010-06-24 | Process for production of (meth)acrylic acid |
JP2011520885A JP6151884B2 (ja) | 2009-07-01 | 2010-06-24 | (メタ)アクリル酸の製造方法 |
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Cited By (2)
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CN102260161A (zh) * | 2011-05-26 | 2011-11-30 | 上海华谊丙烯酸有限公司 | 一种(甲基)丙烯酸的脱色方法 |
JP2014065705A (ja) * | 2012-09-06 | 2014-04-17 | Nippon Shokubai Co Ltd | (メタ)アクリル酸の製造方法 |
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EP3012244A1 (en) | 2014-10-24 | 2016-04-27 | Sulzer Chemtech AG | Process and apparatus for purification of acrylic acid |
CN113877235B (zh) * | 2020-07-02 | 2023-05-02 | 中国石油化工股份有限公司 | 静态结晶器和静态结晶方法 |
CN115970326A (zh) * | 2023-02-08 | 2023-04-18 | 连云港铭磊科技有限公司 | 一种高纯度丙烯酸用结晶器 |
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CN102260161A (zh) * | 2011-05-26 | 2011-11-30 | 上海华谊丙烯酸有限公司 | 一种(甲基)丙烯酸的脱色方法 |
CN102260161B (zh) * | 2011-05-26 | 2014-06-04 | 上海华谊丙烯酸有限公司 | 一种(甲基)丙烯酸的脱色方法 |
JP2014065705A (ja) * | 2012-09-06 | 2014-04-17 | Nippon Shokubai Co Ltd | (メタ)アクリル酸の製造方法 |
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US8680331B2 (en) | 2014-03-25 |
JPWO2011001891A1 (ja) | 2012-12-13 |
EP2450338A4 (en) | 2015-08-05 |
JP6151884B2 (ja) | 2017-06-21 |
US20120083624A1 (en) | 2012-04-05 |
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CN102471212A (zh) | 2012-05-23 |
EP2450338A1 (en) | 2012-05-09 |
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