JP5485584B2 - （メタ）アクリル酸の製造方法および晶析システム - Google Patents
（メタ）アクリル酸の製造方法および晶析システム Download PDFInfo
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- JP5485584B2 JP5485584B2 JP2009119162A JP2009119162A JP5485584B2 JP 5485584 B2 JP5485584 B2 JP 5485584B2 JP 2009119162 A JP2009119162 A JP 2009119162A JP 2009119162 A JP2009119162 A JP 2009119162A JP 5485584 B2 JP5485584 B2 JP 5485584B2
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- 238000002425 crystallisation Methods 0.000 title claims description 169
- 230000008025 crystallization Effects 0.000 title claims description 168
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 162
- 238000004519 manufacturing process Methods 0.000 title claims description 57
- 238000010438 heat treatment Methods 0.000 claims description 432
- 239000002826 coolant Substances 0.000 claims description 399
- 238000002844 melting Methods 0.000 claims description 84
- 230000008018 melting Effects 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 61
- 239000013078 crystal Substances 0.000 claims description 53
- 238000007599 discharging Methods 0.000 claims description 41
- 238000001816 cooling Methods 0.000 description 49
- 239000000243 solution Substances 0.000 description 48
- 238000005265 energy consumption Methods 0.000 description 25
- 238000010309 melting process Methods 0.000 description 21
- 239000007788 liquid Substances 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 8
- 238000004891 communication Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 230000035900 sweating Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- IPLONMMJNGTUAI-UHFFFAOYSA-M lithium;bromide;hydrate Chemical compound [Li+].O.[Br-] IPLONMMJNGTUAI-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009119162A JP5485584B2 (ja) | 2009-05-15 | 2009-05-15 | （メタ）アクリル酸の製造方法および晶析システム |
| CN201080018465.XA CN102414160B (zh) | 2009-05-15 | 2010-05-07 | 制备(甲基)丙烯酸的方法和结晶系统 |
| EP10774860.0A EP2431350B1 (en) | 2009-05-15 | 2010-05-07 | Method for producing (meth)acrylic acid and crystallization system |
| US13/266,983 US8592627B2 (en) | 2009-05-15 | 2010-05-07 | Process for producing (meth)acrylic acid and crystallization system |
| PCT/JP2010/057808 WO2010131603A1 (ja) | 2009-05-15 | 2010-05-07 | (メタ)アクリル酸の製造方法および晶析システム |
| BRPI1012135A BRPI1012135A2 (pt) | 2009-05-15 | 2010-05-07 | processo para produzir ácido (met) acrílico e sistema de cristalização |
| SG2011079142A SG175379A1 (en) | 2009-05-15 | 2010-05-07 | Process for producing (meth)acrylic acid and crystallization system |
| TW99114899A TWI466862B (zh) | 2009-05-15 | 2010-05-11 | Production method and crystallization system of methacrylic acid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009119162A JP5485584B2 (ja) | 2009-05-15 | 2009-05-15 | （メタ）アクリル酸の製造方法および晶析システム |
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| Publication Number | Publication Date |
|---|---|
| JP2010265227A JP2010265227A (ja) | 2010-11-25 |
| JP2010265227A5 JP2010265227A5 (enExample) | 2012-03-29 |
| JP5485584B2 true JP5485584B2 (ja) | 2014-05-07 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2009119162A Active JP5485584B2 (ja) | 2009-05-15 | 2009-05-15 | （メタ）アクリル酸の製造方法および晶析システム |
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| Country | Link |
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| JP (1) | JP5485584B2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5485585B2 (ja) * | 2009-05-15 | 2014-05-07 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
| JP5580813B2 (ja) * | 2009-05-15 | 2014-08-27 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06159831A (ja) * | 1992-11-19 | 1994-06-07 | Shin Meiwa Ind Co Ltd | 冷凍装置 |
| JP3214322B2 (ja) * | 1995-01-24 | 2001-10-02 | 三菱化学株式会社 | 反応温度の調節方法 |
| JP4326353B2 (ja) * | 2004-01-22 | 2009-09-02 | 新明和工業株式会社 | 超低温冷凍装置 |
| JP5715318B2 (ja) * | 2005-12-06 | 2015-05-07 | 株式会社日本触媒 | アクリル酸の製造方法 |
| JP4253330B2 (ja) * | 2006-04-07 | 2009-04-08 | 株式会社日本触媒 | 有機酸の製造方法 |
| JP4256887B2 (ja) * | 2006-09-20 | 2009-04-22 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
| CN105477897B (zh) * | 2007-03-14 | 2017-09-19 | 三菱化学株式会社 | 析晶方法及用于其的析晶装置 |
| JP5485585B2 (ja) * | 2009-05-15 | 2014-05-07 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
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- 2009-05-15 JP JP2009119162A patent/JP5485584B2/ja active Active
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| Publication number | Publication date |
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| JP2010265227A (ja) | 2010-11-25 |
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