JP4654584B2 - (メタ)アクリル酸エステル含有液の取り扱い方法 - Google Patents
(メタ)アクリル酸エステル含有液の取り扱い方法 Download PDFInfo
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- JP4654584B2 JP4654584B2 JP2004056333A JP2004056333A JP4654584B2 JP 4654584 B2 JP4654584 B2 JP 4654584B2 JP 2004056333 A JP2004056333 A JP 2004056333A JP 2004056333 A JP2004056333 A JP 2004056333A JP 4654584 B2 JP4654584 B2 JP 4654584B2
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- JP
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- Prior art keywords
- meth
- extraction
- acrylic acid
- liquid
- tower
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000007788 liquid Substances 0.000 title claims description 32
- -1 acrylic ester Chemical class 0.000 title description 9
- 238000000605 extraction Methods 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 38
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 239000007864 aqueous solution Substances 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- 239000002699 waste material Substances 0.000 claims description 22
- 238000000926 separation method Methods 0.000 claims description 20
- 239000002351 wastewater Substances 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 17
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 14
- 238000006386 neutralization reaction Methods 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000011084 recovery Methods 0.000 description 14
- 239000010410 layer Substances 0.000 description 11
- 238000000622 liquid--liquid extraction Methods 0.000 description 11
- 238000000638 solvent extraction Methods 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000003377 acid catalyst Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 239000010802 sludge Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000007774 longterm Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 229910017053 inorganic salt Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011973 solid acid Substances 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/66—Treatment of water, waste water, or sewage by neutralisation; pH adjustment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0488—Flow sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/26—Treatment of water, waste water, or sewage by extraction
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
- C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Environmental & Geological Engineering (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Specific Substances (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Extraction Or Liquid Replacement (AREA)
- Physical Water Treatments (AREA)
Description
アクリル酸メチルエステル製造工程で、エステル化反応生成物中のアクリル酸などの重質分を蒸留除去した留分を原料に使用し、図1のフロー図に示す装置で連続運転を実施した。
実施例1において、平均組成が、水:13重量%、メタノール:10重量%、アクリル酸メチル:75重量%、その他:2重量%であるフィード原料を使用し、平均流量を3.0トン/時間に、抽出操作温度を20℃にそれぞれ変更した以外は、実施例1と同様の操作により連続運転を行った。300日間の連続運転の結果、抽出塔(1)上部の有機層中のメタノール濃度は0.2〜0.3重量%の間で安定し、連続安定運転が達成できた。
実施例1において、アルコール回収塔(2)の塔底から排出される廃水溶液について、冷却およびフィルター処理をしないこと以外は、実施例1と全く同一の装置、原料および運転条件で連続運転を実施した。その結果、200日経過時点から回収塔(2)の上部の有機層中のメタノール濃度が0.2重量%を超えた。更に、抽出塔(1)内で析出固形物の蓄積が始まったために液液界面が不安定となり、管路(L3)の液中にエタノール及び水が増加し、管路(L3)以降の設備の運転が不可能になった。一方、アルコール回収塔(2)においても塔頂−塔底間の差圧が上昇し始め、塔底温度が上昇したためにアルコール回収塔(2)の熱源であるスチームの供給が低下し、運転不可能となった。
実施例2において、アルコール回収塔(2)の塔底から排出される廃水溶液について、冷却およびフィルター処理をしないこと以外は、実施例2と全く同一の装置、原料および運転条件で連続運転を実施した。その結果、150日経過時点から回収塔(2)の上部の有機層中のメタノール濃度が0.3重量%を超えた。更に、抽出塔(1)内で析出固形物の蓄積が始まったために液液界面が不安定となり、管路(L3)の液中にエタノール及び水が増加し、管路(L3)以降の設備の運転が不可能になった。一方、アルコール回収塔(2)においても塔頂−塔底間の差圧が上昇し始め、塔底温度が上昇したためにアルコール回収塔(2)の熱源であるスチームの供給が低下し、運転不可能となった。
2:アルコール回収塔
3:熱交換器
4:熱交換器
5:バッファードラム
6:フィルター
Claims (7)
- (メタ)アクリル酸エステル含有液に対し、洗浄、中和、抽出の何れか1又は2以上のプロセスで処理を行う(メタ)アクリル酸エステル含有液の取り扱い方法において、上記の何れか1又は2以上のプロセスでの処理を10〜50℃で行い、処理後に蒸留によりアルコールを回収し、回収した後の廃水または廃水溶液をその前プロセスに循環使用するに当たり、予め、10〜50℃の温度に冷却した後に、静置分離槽に導入し、軽析出固形分を除去した後、濾過することによって固形分を除去することを特徴とする(メタ)アクリル酸エステル含有液の取り扱い方法。
- 前記廃水または廃水溶液の温度が80〜110℃である請求項1に記載の方法。
- 洗浄および/または抽出が抽出塔で行われる操作である請求項1又は2に記載の方法。
- 前記プロセスが抽出である請求項1〜3の何れかに記載の方法。
- 前記蒸留により塔頂からアルコールを回収し、塔底から廃水または廃水溶液が得られる請求項1〜4の何れかに記載の方法。
- 濾過が透過粒径1〜10μmのフィルターを使用して行う請求項1〜5の何れかに記載の方法。
- (メタ)アクリル酸エステルが、アクリル酸メチル、アクリル酸エチル又はメタクリル酸メチルである請求項1〜6の何れかに記載の方法。
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004056333A JP4654584B2 (ja) | 2004-03-01 | 2004-03-01 | (メタ)アクリル酸エステル含有液の取り扱い方法 |
AU2004235633A AU2004235633A1 (en) | 2004-03-01 | 2004-10-08 | Method for handling (meth)acrylic ester-containing solution |
BRPI0405628-0A BRPI0405628B1 (pt) | 2004-03-01 | 2004-10-08 | Método para manipulação de solução contendo éster (met) acrílico |
CN2004800003907A CN1697823B (zh) | 2004-03-01 | 2004-10-08 | 处理含(甲基)丙烯酸酯溶液的方法 |
EP04792201A EP1721886B1 (en) | 2004-03-01 | 2004-10-08 | Method of processing methacrylic-ester-containing solution |
ZA200409853A ZA200409853B (en) | 2004-03-01 | 2004-10-08 | Method for handling (meth)acrylic ester-containing solution |
ES04792201T ES2358194T3 (es) | 2004-03-01 | 2004-10-08 | Método de procesado de una disolución que contiene éster (met)acrílico. |
RU2004137684/15A RU2004137684A (ru) | 2004-03-01 | 2004-10-08 | Способ обработки раствора, содержащего сложный эфир (мет) акриловой кислоты |
PCT/JP2004/014932 WO2005082831A1 (ja) | 2004-03-01 | 2004-10-08 | (メタ)アクリル酸エステル含有液の取り扱い方法 |
US11/015,744 US20050189296A1 (en) | 2004-03-01 | 2004-12-20 | Method for handling (meth) acrylic ester-containing solution |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004056333A JP4654584B2 (ja) | 2004-03-01 | 2004-03-01 | (メタ)アクリル酸エステル含有液の取り扱い方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005246132A JP2005246132A (ja) | 2005-09-15 |
JP4654584B2 true JP4654584B2 (ja) | 2011-03-23 |
Family
ID=34908909
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004056333A Expired - Lifetime JP4654584B2 (ja) | 2004-03-01 | 2004-03-01 | (メタ)アクリル酸エステル含有液の取り扱い方法 |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1721886B1 (ja) |
JP (1) | JP4654584B2 (ja) |
CN (1) | CN1697823B (ja) |
AU (1) | AU2004235633A1 (ja) |
BR (1) | BRPI0405628B1 (ja) |
ES (1) | ES2358194T3 (ja) |
RU (1) | RU2004137684A (ja) |
WO (1) | WO2005082831A1 (ja) |
ZA (1) | ZA200409853B (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006058251A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Verfahren und Vorrichtung zur Herstellung von Methacrylsäurealkylestern |
JP2009167374A (ja) * | 2007-07-10 | 2009-07-30 | Sekisui Chem Co Ltd | 高分子量のヒドロキシ安息香酸エステル類の製造方法 |
CN101343223B (zh) * | 2008-08-20 | 2011-03-16 | 山东齐鲁石化开泰实业股份有限公司 | 连续酯化法丙烯酸甲/乙酯生产系统可调节装置 |
JP5720528B2 (ja) * | 2011-10-19 | 2015-05-20 | 東亞合成株式会社 | アクリレートの製造方法及びアクリル酸の回収方法 |
FR3010998B1 (fr) * | 2013-09-23 | 2016-11-25 | Arkema France | Procede d'extraction liquide - liquide pour la production d'esters acryliques |
CN105084608B (zh) * | 2015-09-17 | 2017-05-31 | 博天环境集团股份有限公司 | 一种丙烯酸酯废水生化处理的预处理方法 |
CN106117014A (zh) * | 2016-06-20 | 2016-11-16 | 山东广浦生物科技有限公司 | 从甲基丙烯酸甲酯‑甲醇混合液中萃取甲醇的方法 |
JP7396455B2 (ja) * | 2020-02-26 | 2023-12-12 | 三菱ケミカル株式会社 | 水を含む結晶の分離方法、メタクリル酸の製造方法、及びメタクリル酸エステルの製造方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6299345A (ja) * | 1985-10-24 | 1987-05-08 | Nippon Kayaku Co Ltd | アクリル酸エステル又はメタクリル酸エステルの回収法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3346822B2 (ja) * | 1993-03-31 | 2002-11-18 | 三菱化学株式会社 | アクリル酸エステル又はメタクリル酸エステルの製造法 |
DE10144490A1 (de) * | 2001-09-10 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
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2004
- 2004-03-01 JP JP2004056333A patent/JP4654584B2/ja not_active Expired - Lifetime
- 2004-10-08 ZA ZA200409853A patent/ZA200409853B/en unknown
- 2004-10-08 ES ES04792201T patent/ES2358194T3/es active Active
- 2004-10-08 AU AU2004235633A patent/AU2004235633A1/en not_active Abandoned
- 2004-10-08 EP EP04792201A patent/EP1721886B1/en active Active
- 2004-10-08 RU RU2004137684/15A patent/RU2004137684A/ru not_active Application Discontinuation
- 2004-10-08 CN CN2004800003907A patent/CN1697823B/zh active Active
- 2004-10-08 BR BRPI0405628-0A patent/BRPI0405628B1/pt active IP Right Grant
- 2004-10-08 WO PCT/JP2004/014932 patent/WO2005082831A1/ja not_active Application Discontinuation
Patent Citations (1)
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JPS6299345A (ja) * | 1985-10-24 | 1987-05-08 | Nippon Kayaku Co Ltd | アクリル酸エステル又はメタクリル酸エステルの回収法 |
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ES2358194T3 (es) | 2011-05-06 |
ZA200409853B (en) | 2007-04-25 |
CN1697823B (zh) | 2010-11-10 |
BRPI0405628B1 (pt) | 2014-02-18 |
RU2004137684A (ru) | 2006-03-20 |
EP1721886B1 (en) | 2011-03-09 |
JP2005246132A (ja) | 2005-09-15 |
CN1697823A (zh) | 2005-11-16 |
AU2004235633A1 (en) | 2005-09-15 |
BRPI0405628A (pt) | 2006-02-21 |
WO2005082831A1 (ja) | 2005-09-09 |
EP1721886A4 (en) | 2007-05-09 |
EP1721886A1 (en) | 2006-11-15 |
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