WO2010090100A1 - フィルターの再生方法 - Google Patents
フィルターの再生方法 Download PDFInfo
- Publication number
- WO2010090100A1 WO2010090100A1 PCT/JP2010/050974 JP2010050974W WO2010090100A1 WO 2010090100 A1 WO2010090100 A1 WO 2010090100A1 JP 2010050974 W JP2010050974 W JP 2010050974W WO 2010090100 A1 WO2010090100 A1 WO 2010090100A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acrylic acid
- filter
- regeneration
- regenerating
- purified
- Prior art date
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D65/00—Accessories or auxiliary operations, in general, for separation processes or apparatus using semi-permeable membranes
- B01D65/02—Membrane cleaning or sterilisation ; Membrane regeneration
-
- 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
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2321/00—Details relating to membrane cleaning, regeneration, sterilization or to the prevention of fouling
- B01D2321/16—Use of chemical agents
- B01D2321/162—Use of acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2321/00—Details relating to membrane cleaning, regeneration, sterilization or to the prevention of fouling
- B01D2321/16—Use of chemical agents
- B01D2321/164—Use of bases
Definitions
- the present invention relates to a method for regenerating a filter, and more particularly to a method for regenerating a filter used in a filtration step of a process for producing acrylic acid.
- a process for producing acrylic acid through a catalytic gas phase oxidation step, a collection and / or condensation step, a distillation purification and / or a crystallization step is widely performed industrially.
- Purified acrylic acid is transferred to and stored in a storage tank. If a small amount of acrylic acid polymer is contained in the purified acrylic acid, additional acrylic acid polymer is generated during the storage, and purified acrylic acid is produced. Problems such as reduced acid purity occur.
- the acrylic acid polymer adhering to the filter can be substantially removed by washing with water and a sodium hydroxide aqueous solution and further washing with water.
- the final water washing is performed in order to remove the alkali residue remaining on the filter after washing with a sodium hydroxide aqueous solution.
- the filter regenerated by the above method is reused for filtration of purified acrylic acid
- the color of the purified acrylic acid after the resumption of filtration is poor, the metal (mainly iron) content is high, and the metal is purified acrylic acid.
- the present inventors have found that the color tone is affected.
- the color tone and metal content of purified acrylic acid are numerical values in purified acrylic acid immediately after the crystallization process by passing a certain amount of purified acrylic acid through a filter, and are the usual numerical values generally required for product acrylic acid. It was found that APHA can be returned to 5 or less and the metal content to 1 mass ppm or less.
- an object of the present invention is to provide a method for regenerating a filter that prevents deterioration of the color tone of purified acrylic acid.
- the present inventors have conducted a detailed investigation and found that the metal contains a metal component (mainly iron component) that is slightly eluted from the reactor used in the process of producing acrylic acid. That is, the metal remains on the filter as an oxide when the filter is washed with an alkaline aqueous solution, and is eluted into the purified acrylic acid when the filter is reused, which deteriorates the color tone of the purified acrylic acid. It is. In order to eliminate the above cause, the present inventors have intensively studied and completed the present invention.
- a metal component mainly iron component
- the present invention is a method for regenerating a filter used in a filtration step of a process for producing acrylic acid, the step (A) of washing the filter with an alkaline aqueous solution, and the filter after the step (A).
- a method for regenerating a filter comprising: (B) washing with water; and (C) contacting the filter with regenerating acrylic acid for at least 1 hour after the step (B).
- This embodiment is a method for regenerating a filter used in a filtration step of a process for producing acrylic acid, wherein the filter is washed with water after the step (A) of washing the filter with an alkaline aqueous solution and the step (A).
- a method of regenerating a filter comprising: a step (B) of washing; and a step (C) of contacting the filter with acrylic acid for regeneration for at least 1 hour after the step (B).
- the process for producing this form of acrylic acid is not particularly limited.
- the process which consists of a process which manufactures acrylic acid through a contact gas-phase oxidation process, a collection and / or condensation process, and also a distillation purification and / or crystallization process, etc. are mentioned.
- the “crystallization process” is a well-known process for purifying acrylic acid by crystallization, sweating and melting.
- the filtration step of this embodiment is performed for the purpose of removing the acrylic acid polymer contained in the purified acrylic acid, and is performed using a filter.
- the filtration step is not particularly limited as long as it is performed in the process of producing acrylic acid, but is performed when the purified acrylic acid obtained from the distillation purification and / or crystallization step is transferred to the storage tank. Or when the acrylic acid solution obtained from the collection and / or condensation process is transferred to another storage tank provided as needed before being supplied to the distillation purification and / or crystallization process. And the like. Especially, it is preferable to carry out in the line which transfers the refined acrylic acid obtained from a crystallization process to the storage tank.
- the type, shape, material, and the like of the filter regenerated in this embodiment are not particularly limited as long as it can be used for removing the acrylic acid polymer.
- a commercially available cartridge type filter is preferably used for reasons such as work simplicity.
- Specific examples include a membrane cartridge filter made of polytetrafluoroethylene (PTFE), a pleated cartridge filter made of polypropylene (PP), a depth cartridge filter, a wind cartridge filter, and a pleated cartridge filter made of stainless steel.
- PTFE polytetrafluoroethylene
- PP polypropylene
- This embodiment is particularly effective for the regeneration of a resin cartridge filter such as PTFE or PP that cannot be backwashed in strength.
- the filter regeneration method can be used in any form in which a filter housing containing a cartridge type filter is used alone, or two or more filter housings containing cartridge type filters are arranged in series and / or in parallel.
- two filter housings (I) and (II) are installed in parallel, and first, filtration is performed by flowing purified acrylic acid through the filter housing (I). Thereafter, if the differential pressure applied to the filter increases due to the adhesion of the polymerized product on the filter, the flow of the purified acrylic acid is switched to the filter housing (II), and the filtration of the purified acrylic acid is continued.
- the filters in the filter housing (I) are not particularly limited to the following order, but are regenerated as follows, for example.
- step (C) 1) Remove and recover the acrylic acid remaining in the housing. 2) Wash the inside of the housing with water and wash away the remaining acrylic acid [step (X)]. 3) Fill the housing with an alkaline aqueous solution to remove the polymer adhering to the filter [step (A)]. 4) After extracting the aqueous alkali solution from the inside of the housing, the inside of the housing is washed with water to wash away the alkali [step (B)]. 5) The housing is filled with acrylic acid for regeneration, and the filter is brought into contact with the acrylic acid [step (C)].
- the above step 1) may be general removal and / or recovery, such as flushing out.
- the recovered acrylic acid can be circulated to the acrylic acid collection step.
- the pH of the water after washing away the remaining acrylic acid is 4.0 or more, more preferably 5.5 or more, and even more preferably 6.5 or more. Wash out repeatedly.
- a lithium hydroxide aqueous solution As the “alkali aqueous solution” used in the above step 3), a lithium hydroxide aqueous solution, a sodium hydroxide aqueous solution, a magnesium hydroxide aqueous solution, a potassium hydroxide aqueous solution, a calcium hydroxide aqueous solution, a barium hydroxide aqueous solution and the like can be used.
- a sodium hydroxide aqueous solution and a potassium hydroxide aqueous solution are preferable from the viewpoint of availability and the ability to remove a polymer.
- the concentration of the aqueous alkali solution is not particularly limited, but is preferably 0.1 to 30% by mass, more preferably 1.0 to 20% by mass, and still more preferably 2.0 to 15% by mass.
- the alkaline aqueous solution is circulated in the housing to promote the removal of the polymer adhering to the filter.
- step 4 the washing is repeated until the pH of the water after washing away the remaining alkali is 8.0 or less, more preferably 7.5 or less.
- the filter may be brought into contact with acrylic acid for regeneration, and the contact method is not particularly limited.
- the acrylic acid for regeneration is dripped from the upper part of the filter, or the filter is immersed in the acrylic acid for regeneration.
- the filter When the filter is immersed in the regenerating acrylic acid, it may be simply immersed in the stationary regenerating acrylic acid, and in some cases, it may be immersed in the circulating regenerating acrylic acid.
- a mechanical method such as rubbing off may be added at an arbitrary point in contact with the acrylic acid for regeneration.
- the regenerating acrylic acid preferably has a purity capable of efficiently washing the filter, and the APHA of the regenerating acrylic acid is preferably 10 or less, more preferably 5 or less, and even more preferably 2 or less.
- the metal content of the acrylic acid for regeneration is preferably 3 ppm by mass or less, more preferably 1 ppm by mass or less, and even more preferably 0.1 ppm by mass or less.
- the temperature of the acrylic acid for regeneration is preferably in the range of 14 to 80 ° C. in consideration of the melting point of acrylic acid, the heat resistant temperature of the filter, etc., and more preferably in consideration of the polymerizability of acrylic acid. Is 15 to 40 ° C.
- the time for bringing the filter into contact with the regenerating acrylic acid under the above conditions is preferably at least 1 hour, more preferably 2 hours or more. If the filter is immersed in regenerating acrylic acid for 1 hour or longer, the metal oxide on the filter can be sufficiently removed, and the amount of off-spec products as described above is reduced.
- the deterioration of the color tone of the purified acrylic acid can be efficiently prevented by using the filter after performing the above steps 1 to 5 in the filtration step.
- the regeneration of the filter may be performed outside the housing with the filter removed. Moreover, the filter after reproduction
- the color tone and the metal content were measured by the following methods.
- Color tone An absorption colorimeter (Sigrist Co. color plus “Color Plus”) was installed in the liquid feeding line, and chromaticity (APHA) was measured online (measurement light wavelength: 365 nm, comparative light wavelength: 650 nm).
- APHA chromaticity
- Iron content After acrylic acid was diluted 5 times with ultrapure water, it was analyzed with an ICP (high frequency induction plasma) emission spectrometer.
- the purified acrylic acid used here was prepared as follows. ⁇ Acrylic acid collection process> A reaction gas obtained by catalytic vapor phase oxidation of propylene by the same method as in Example 1 of JP-A-2005-15478 is brought into contact with an aqueous solution for collection, and acrylic acid 90.0 is introduced from the bottom of the collection tower. Mass%, water 3.2 mass%, acetic acid 1.9 mass%, maleic acid 0.6 mass%, acrylic acid dimer 1.5 mass%, aldehydes 0.4 mass%, hydroquinone 0.1 mass% An acrylic acid solution having a composition of 2.3% by mass of other impurities was obtained.
- the bottom temperature of the collection tower at this time that is, the temperature of the acrylic acid solution taken out from the collection tower was 91 ° C.
- ⁇ Acrylic acid crystallization process> After cooling the acrylic acid solution, it was supplied to a crystallizer and purified by performing dynamic crystallization four times.
- the dynamic crystallization was performed with a crystallization apparatus according to the crystallization apparatus described in Japanese Patent Publication No. 53-41637. That is, a reservoir is provided at the bottom, a metal pipe having a length of 6 m and an inner diameter of 70 mm, the liquid in the reservoir is transferred to the top of the pipe by a circulation pump, and the liquid is allowed to flow in the form of a falling film on the inner wall surface of the pipe.
- the surface of the tube is composed of a double jacket, and the jacket is controlled by a thermostat so as to have a constant temperature.
- One dynamic crystallization was performed by the following procedure. 1) Crystallization: Acrylic acid was supplied to the reservoir, and it was allowed to flow in the form of a falling film on the wall surface of the tube by a circulation pump, the temperature of the jacket was lowered below the freezing point, and about 60 to 90% by mass was crystallized on the wall surface. 2) Sweating: The circulation pump was stopped, the jacket temperature was raised to near the freezing point, and about 2 to 20% was sweated. After sweating, the residual melt was pumped out. 3) Melting: The temperature of the jacket was raised above the freezing point, the crystals were melted, and pumped out.
- the temperature and freezing point depend on each process to be performed.
- purified acrylic acid having a purity of 99.93% by mass was obtained.
- the composition of other components of the purified acrylic acid was 100 mass ppm of water, 475 mass ppm of acetic acid, 2 mass ppm of maleic acid, 30 mass ppm of acrylic acid dimer, and 0.4 mass ppm of aldehydes.
- methoquinone was added as a stabilizer so as to be 200 ppm by mass.
- the APHA of the purified acrylic acid was 2, and the iron content was 0.1 ppm by mass.
- the purified acrylic acid was supplied to a storage tank through a cartridge housing containing a cartridge filter (TCP-1 manufactured by ADVANTEC, pleated cartridge filter manufactured by PP, pore diameter 1 ⁇ m). At this time, the linear velocity of the purified acrylic acid in the filter part was 0.01 m / s.
- a cartridge filter TCP-1 manufactured by ADVANTEC, pleated cartridge filter manufactured by PP, pore diameter 1 ⁇ m.
- Example 1 When the differential pressure at the filter portion reached 0.1 MPa, the supply of purified acrylic acid was stopped, and the filter was regenerated by the following procedure.
- Example 1 1) Acrylic acid remaining in the housing was extracted. The acrylic acid was recovered and circulated to the acrylic acid collection step. 2) Water was supplied into the housing, and the filter was washed with water. That is, after filling the inside of the housing with water, the continuous operation of extracting water immediately was repeated until the pH of the water after washing reached 6.5. A part of the water after the early washing was collected and then circulated to the acrylic acid collecting step, and the remaining washed water was removed from the system. 3) A 10% by mass aqueous sodium hydroxide solution was supplied into the housing, and the filter was alkali washed.
- the alkali cleaning was performed as follows. That is, the inside of the housing was filled with an aqueous sodium hydroxide solution, and the aqueous sodium hydroxide solution was circulated through the housing for a while with a pump and then extracted from the housing. This operation was repeated three times. The alkaline aqueous solution after washing was removed from the system. 4) Water was supplied into the housing, and the filter was washed with water. That is, after filling the housing with water, the continuous operation of extracting water immediately was repeated until the pH of the liquid after washing became 7.5. 5) Purified acrylic acid was supplied into the housing as a regenerating acrylic acid, and the inside of the housing was filled with the acrylic acid. The filter was immersed for 1 hour with the temperature of the acrylic acid for regeneration being 40 ° C., and then the acrylic acid was extracted. The extracted acrylic acid was collected and circulated to the acrylic acid crystallization step.
- Example 2> In step 5), the same procedure as in Example 1 was performed except that the temperature of the acrylic acid for regeneration was 25 ° C. ⁇ Example 3> In the step 5), the same procedure as in Example 1 was performed, except that the temperature of the acrylic acid for regeneration was 15 ° C. ⁇ Example 4> In the step 5), the same procedure as in Example 2 was performed, except that the regenerating acrylic acid was immersed for 2 hours. ⁇ Example 5> In step 5), the same procedure as in Example 2 was performed, except that the regeneration acrylic acid was immersed for 3 hours. ⁇ Example 6> In the step 5), the same procedure as in Example 2 was performed, except that the regenerating acrylic acid was immersed for 6 hours.
- Example 7> In the step 5), the same procedure as in Example 2 was performed, except that the regeneration acrylic acid was immersed for 9 hours.
- Example 8> In the step 5), the same procedure as in Example 2 was performed, except that the regeneration acrylic acid was immersed for 12 hours.
- ⁇ Comparative Example 1> In the step 5), the same procedure as in Example 2 was performed except that the acrylic acid for regeneration was not satisfied.
- ⁇ Comparative example 2> In the above step 5), the same procedure as in Example 2 was performed, except that the regeneration acrylic acid was immersed for 0.5 hour.
- Example 3> In the step 5), the same procedure as in Example 1 was performed, except that the regeneration acrylic acid immersion time was 0.5 hour.
- ⁇ Comparative example 4> In step 5), the same procedure as in Example 3 was performed, except that the regeneration acrylic acid immersion time was 0.5 hour.
- the required time refers to the color tone and metal content of the filtered acrylic acid after the reactivation of the filter and the metal content (mainly iron) It means the time until it reaches the value of (content) (0.1 mass ppm) and can be transferred to the storage tank.
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- Chemical Kinetics & Catalysis (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
1)ハウジング内に残ったアクリル酸を除去して、回収する。
2)ハウジング内を水洗浄し、残留するアクリル酸を洗い流す[工程(X)]。
3)アルカリ水溶液をハウジング内に満たし、フィルターに付着した重合物を除去する[工程(A)]。
4)アルカリ水溶液をハウジング内から抜き出した後、ハウジング内を水洗浄し、アルカリを洗い流す[工程(B)]。
5)ハウジング内を再生用アクリル酸で満たし、フィルターを前記アクリル酸に接触させる[工程(C)]。
色調: 送液ラインに吸光色度計(シグリスト社製色度計「カラープラス」)を設置し、オンラインにて色度(APHA)を測定した(測定光波長:365nm、比較光波長:650nm)。
鉄含有量: アクリル酸を超純水で5倍に希釈した後、ICP(高周波誘導プラズマ)発光分析装置にて分析した。
<アクリル酸の捕集工程>
特開2005-15478号公報の実施例1と同様の方法によるプロピレンの接触気相酸化反応によって得られる反応ガスを捕集用水溶液と接触させ、捕集塔の塔底より、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%、アルデヒド類0.4質量%、ハイドロキノン0.1質量%、その他の不純物2.3質量%の組成をもつアクリル酸溶液を得た。なお、このときの捕集塔の塔底温度、すなわち捕集塔より取り出されるアクリル酸溶液の温度は91℃であった。
<アクリル酸の晶析工程>
上記アクリル酸溶液を冷却した後、晶析装置に供給し、動的結晶化を4回行い、精製した。動的結晶化は、特公昭53-41637号公報に記載された晶析装置に準じた晶析装置で行った。すなわち、下部に貯蔵器を備え、長さ6m、内径70mmの金属管で、循環ポンプにより貯蔵器中の液体を管上部へ移送し、液体を管内壁面に落下被膜(falling film)状に流すことができるようになっている装置である。管の表面は二重ジャケットから構成され、該ジャケットは、サーモスタットで一定温度になるように制御されている。1回の動的結晶化は以下の手順で行った。
1)結晶化:貯蔵器にアクリル酸を供給し、循環ポンプにより管壁面に落下皮膜状に流し、ジャケットの温度を凝固点以下に下降させ、約60~90質量%を壁面に結晶化させた。
2)発汗:循環ポンプを停止させ、ジャケットの温度を凝固点付近にまで上昇させ、約2~20%を発汗させた。発汗後、残留融解液をポンプで汲み出した。
3)融解:ジャケットの温度を凝固点以上に上昇させ、結晶を融解し、ポンプで汲み出した。
<実施例1>
1)ハウジング内に残存しているアクリル酸を抜き出した。該アクリル酸を回収して、前記アクリル酸の捕集工程へ循環した。
2)ハウジング内に水を供給し、フィルターの水洗浄を行った。すなわち、ハウジング内を水で満たした後、すぐに水を抜き出すという連続操作を、洗浄後の水のpHが6.5になるまで繰り返し行った。早期の洗浄後の水の一部は、回収後、前記アクリル酸の捕集工程へ循環し、残りの洗浄後の水は系外に除去した。
3)ハウジング内に10質量%の水酸化ナトリウム水溶液を供給し、フィルターのアルカリ洗浄を行った。アルカリ洗浄は次のようにして行った。すなわち、ハウジング内を水酸化ナトリウム水溶液で満たし、該水酸化ナトリウム水溶液をポンプによりハウジング内をしばらく循環させた後、ハウジング内から抜き出した。該操作を3回繰り返した。洗浄後のアルカリ水溶液は系外に除去した。
4)ハウジング内に水を供給し、フィルターの水洗浄を行った。すなわち、ハウジング内を水で満たした後、すぐに水を抜き出すという連続操作を、洗浄後の液のpHが7.5になるまで繰り返し行った。
5)再生用アクリル酸として精製アクリル酸をハウジング内に供給し、ハウジング内を該アクリル酸で満たした。前記再生用アクリル酸の温度が40℃になるようにしたまま、フィルターを1時間浸漬した後、該アクリル酸を抜き出した。抜き出したアクリル酸を回収し、前記アクリル酸の晶析工程へ循環した。
<実施例2>
前記工程5)において、再生用アクリル酸の温度を25℃としたこと以外は、実施例1と同様の方法で行った。
<実施例3>
前記工程5)において、再生用アクリル酸の温度を15℃としたこと以外は、実施例1と同様の方法で行った。
<実施例4>
前記工程5)において、再生用アクリル酸の浸漬時間を2時間としたこと以外は、実施例2と同様の方法で行った。
<実施例5>
前記工程5)において、再生用アクリル酸の浸漬時間を3時間としたこと以外は、実施例2と同様の方法で行った。
<実施例6>
前記工程5)において、再生用アクリル酸の浸漬時間を6時間としたこと以外は、実施例2と同様の方法で行った。
<実施例7>
前記工程5)において、再生用アクリル酸の浸漬時間を9時間としたこと以外は、実施例2と同様の方法で行った。
<実施例8>
前記工程5)において、再生用アクリル酸の浸漬時間を12時間としたこと以外は、実施例2と同様の方法で行った。
<比較例1>
前記工程5)において、再生用アクリル酸を満たさないこと以外は、実施例2と同様の方法で行った。
<比較例2>
前記工程5)において、再生用アクリル酸の浸漬時間を0.5時間としたこと以外は、実施例2と同様の方法で行った。
<比較例3>
前記工程5)において、再生用アクリル酸の浸漬時間を0.5時間としたこと以外は、実施例1と同様の方法で行った。
<比較例4>
前記工程5)において、再生用アクリル酸の浸漬時間を0.5時間としたこと以外は、実施例3と同様の方法で行った。
Claims (6)
- アクリル酸を製造するプロセスのろ過工程で使用したフィルターの再生方法であって、
前記フィルターをアルカリ水溶液で洗浄する工程(A)と、
前記工程(A)の後に、前記フィルターを水洗浄する工程(B)と、
前記工程(B)の後に、前記フィルターを再生用アクリル酸に少なくとも1時間接触させる工程(C)と、
を含むフィルターの再生方法。 - 前記再生用アクリル酸の温度が14~80℃である、請求項1に記載の再生方法。
- 前記工程(C)の接触が浸漬である、請求項1または2に記載の再生方法。
- 前記フィルターがカートリッジ型フィルターである、請求項1~3のいずれか1項に記載の再生方法。
- 前記工程(A)の前に、前記フィルターを水洗浄する工程(X)をさらに含む、請求項1~4のいずれか1項に記載の再生方法。
- 前記ろ過工程が、アクリル酸を製造するプロセスの晶析工程で得られた精製アクリル酸を貯蔵タンクに移送するライン中で行われるものである、請求項1~5のいずれか1項に記載の再生方法。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP10738438.0A EP2394732B1 (en) | 2009-02-03 | 2010-01-26 | Method for regenerating filter |
JP2010549439A JP5461442B2 (ja) | 2009-02-03 | 2010-01-26 | フィルターの再生方法 |
US13/147,261 US8734655B2 (en) | 2009-02-03 | 2010-01-26 | Method for regenerating filter |
CN201080006417.9A CN102300626B (zh) | 2009-02-03 | 2010-01-26 | 过滤器的再生方法 |
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JP2009022639 | 2009-02-03 | ||
JP2009-022639 | 2009-09-30 |
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WO2010090100A1 true WO2010090100A1 (ja) | 2010-08-12 |
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PCT/JP2010/050974 WO2010090100A1 (ja) | 2009-02-03 | 2010-01-26 | フィルターの再生方法 |
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US (1) | US8734655B2 (ja) |
EP (1) | EP2394732B1 (ja) |
JP (1) | JP5461442B2 (ja) |
CN (1) | CN102300626B (ja) |
WO (1) | WO2010090100A1 (ja) |
Citations (9)
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DE10122787A1 (de) * | 2001-05-10 | 2002-06-06 | Basf Ag | Verfahren zur Herstellung einer gereinigten Schmelze wenigstens eines Monomeren |
EP1810958B1 (en) * | 2006-01-20 | 2010-03-17 | Nippon Shokubai Co., Ltd. | Method for purifying acrylic acid |
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JPS5341637B1 (ja) | 1967-04-14 | 1978-11-06 | ||
JPS62120341A (ja) * | 1985-11-20 | 1987-06-01 | Mitsui Toatsu Chem Inc | メタクリル酸の精製法 |
JPH01307407A (ja) * | 1988-06-02 | 1989-12-12 | Nitto Denko Corp | 膜モジュールの殺菌洗浄方法 |
JPH09141058A (ja) * | 1995-11-15 | 1997-06-03 | Nippon Millipore Kk | 半導体ウエハ処理液の精製膜及び方法 |
JP2002248325A (ja) * | 2001-02-27 | 2002-09-03 | Asahi Kasei Corp | 分離膜の洗浄方法 |
JP2005015478A (ja) | 2003-06-05 | 2005-01-20 | Nippon Shokubai Co Ltd | アクリル酸の製造方法 |
WO2007052505A1 (ja) * | 2005-11-01 | 2007-05-10 | Asahi Kasei Chemicals Corporation | イソブテン及び第3級ブタノールの製造方法 |
JP2007191449A (ja) * | 2006-01-20 | 2007-08-02 | Nippon Shokubai Co Ltd | アクリル酸の製造方法 |
JP2007217403A (ja) * | 2006-01-20 | 2007-08-30 | Nippon Shokubai Co Ltd | アクリル酸の精製方法および製造方法 |
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CN102300626A (zh) | 2011-12-28 |
EP2394732A4 (en) | 2013-05-22 |
JPWO2010090100A1 (ja) | 2012-08-09 |
CN102300626B (zh) | 2014-10-15 |
US20110284470A1 (en) | 2011-11-24 |
JP5461442B2 (ja) | 2014-04-02 |
US8734655B2 (en) | 2014-05-27 |
EP2394732B1 (en) | 2021-03-31 |
EP2394732A1 (en) | 2011-12-14 |
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