JP2018527376A5 - - Google Patents
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- Publication number
- JP2018527376A5 JP2018527376A5 JP2018513794A JP2018513794A JP2018527376A5 JP 2018527376 A5 JP2018527376 A5 JP 2018527376A5 JP 2018513794 A JP2018513794 A JP 2018513794A JP 2018513794 A JP2018513794 A JP 2018513794A JP 2018527376 A5 JP2018527376 A5 JP 2018527376A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl methacrylate
- reactor
- process step
- methacrylic acid
- alcohol
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000002815 homogeneous catalyst Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- -1 alkyl methacrylates Chemical class 0.000 claims 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- 238000000605 extraction Methods 0.000 claims 5
- 238000004821 distillation Methods 0.000 claims 4
- 239000012074 organic phase Substances 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000008346 aqueous phase Substances 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 230000002194 synthesizing effect Effects 0.000 claims 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000005395 methacrylic acid group Chemical class 0.000 claims 2
- 238000006709 oxidative esterification reaction Methods 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- 239000002699 waste material Substances 0.000 claims 2
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 239000002638 heterogeneous catalyst Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- 238000012805 post-processing Methods 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15185441.1 | 2015-09-16 | ||
| EP15185441.1A EP3144291A1 (de) | 2015-09-16 | 2015-09-16 | Synthese von methacrylsäure aus auf methacrolein basierenden alkylmethacrylat |
| PCT/EP2016/071241 WO2017046001A1 (de) | 2015-09-16 | 2016-09-09 | Synthese von methacrylsäure aus auf methacrolein basierenden alkylmethacrylat |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018527376A JP2018527376A (ja) | 2018-09-20 |
| JP2018527376A5 true JP2018527376A5 (enExample) | 2021-01-14 |
| JP6824253B2 JP6824253B2 (ja) | 2021-02-03 |
Family
ID=54147092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018513794A Active JP6824253B2 (ja) | 2015-09-16 | 2016-09-09 | メタクロレインをベースとするアルキルメタクリレートからのメタクリル酸の合成 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10479754B2 (enExample) |
| EP (2) | EP3144291A1 (enExample) |
| JP (1) | JP6824253B2 (enExample) |
| KR (1) | KR102638806B1 (enExample) |
| CN (1) | CN108137474B (enExample) |
| BR (1) | BR112018005075B8 (enExample) |
| ES (1) | ES2738990T3 (enExample) |
| RU (1) | RU2722364C2 (enExample) |
| SA (1) | SA518391122B1 (enExample) |
| SG (1) | SG11201802077QA (enExample) |
| TW (1) | TWI707842B (enExample) |
| WO (1) | WO2017046001A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018217961A1 (en) * | 2017-05-25 | 2018-11-29 | Rohm And Haas Company | Process for preparing methacrolein |
| CN108440281B (zh) * | 2018-03-16 | 2021-03-02 | 上海载正化工科技发展有限公司 | 化学反应装置及其应用 |
| FR3080623B1 (fr) * | 2018-04-27 | 2021-01-08 | Arkema France | Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse |
| EP3587390A1 (de) * | 2018-06-26 | 2020-01-01 | Röhm GmbH | Verfahren zur herstellung von mma in hohen ausbeuten |
| EP3608305A1 (en) * | 2018-08-10 | 2020-02-12 | Röhm GmbH | Process for producing methacrylic acid or methacrylic acid esters |
| EP3760608A1 (de) * | 2019-07-05 | 2021-01-06 | Röhm GmbH | Verfahren zur herstellung von alkylmethacrylaten und optional methacrylsäure |
| EP3786148A1 (de) | 2019-08-28 | 2021-03-03 | Röhm GmbH | Vereinfachte aufarbeitung des reaktoraustrags einer oxidativen veresterung |
| EP3798206A1 (de) | 2019-09-25 | 2021-03-31 | Röhm GmbH | Verfahren zur herstellung von alkylmethacrylaten mit verbesserter wasser- und säureführung |
| EP3798202A1 (de) * | 2019-09-25 | 2021-03-31 | Röhm GmbH | Verfahren zur aufreinigung von methylmethacrylat von leichtsiedenden komponenten |
| KR102735575B1 (ko) * | 2019-10-01 | 2024-11-27 | 주식회사 엘지화학 | (메트)아크릴산 및 메틸메타크릴레이트의 제조 방법 |
| EP4045479B1 (de) * | 2020-10-23 | 2022-10-26 | Röhm GmbH | Optimiertes verfahren zur herstellung von alkylmethacrylat durch reduzierung störender nebenprodukte |
| US20240327327A1 (en) | 2021-10-08 | 2024-10-03 | Dow Global Technologies Llc | Process for methacrylic acid production |
| EP4605365A1 (en) | 2022-12-08 | 2025-08-27 | Rohm and Haas Company | Process for concurrent methyl methacrylate and methacrylic acid production |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH430691A (de) | 1963-09-17 | 1967-02-28 | Lonza Ag | Verfahren zur Herstellung von Methacrylverbindungen |
| US3819685A (en) * | 1971-12-06 | 1974-06-25 | Standard Oil Co | Preparation of esters from unsaturated aldehydes and alcohols |
| DE3106557A1 (de) | 1981-02-21 | 1982-09-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (alpha)-alkylacroleinen |
| DE3213681A1 (de) | 1982-04-14 | 1983-10-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (alpha)-alkylacroleinen |
| JP2959121B2 (ja) | 1990-11-28 | 1999-10-06 | 三菱瓦斯化学株式会社 | メタクリル酸の製造法 |
| JP3681285B2 (ja) * | 1997-07-08 | 2005-08-10 | 旭化成ケミカルズ株式会社 | メタクリル酸メチルの製造方法 |
| JPH11246453A (ja) * | 1998-03-04 | 1999-09-14 | Asahi Chem Ind Co Ltd | メタクロレイン及びメタノールの回収方法 |
| JP2003113132A (ja) * | 2001-10-05 | 2003-04-18 | Asahi Kasei Corp | メタクロレインの製造方法 |
| ZA200303241B (en) | 2002-05-01 | 2003-11-04 | Rohm & Haas | Improved process for methacrylic acid and methcrylic acid ester production. |
| CN1214865C (zh) * | 2003-01-22 | 2005-08-17 | 中国科学院过程工程研究所 | 一种用于甲基丙烯醛一步氧化酯化生产甲基丙烯酸甲酯的新型催化剂 |
| MY139387A (en) * | 2004-11-17 | 2009-09-30 | Asahi Kasei Chemicals Corp | Oxidation catalyst and oxidation method |
| EP1995231B1 (en) * | 2007-05-25 | 2013-11-20 | Evonik Röhm GmbH | Process for preparation of methyl methacrylate using recycled methanol |
| CN101074192A (zh) * | 2007-06-20 | 2007-11-21 | 天津大学 | 以甲醛为原料制备甲基丙烯酸甲酯的方法 |
| RU89631U1 (ru) | 2009-08-12 | 2009-12-10 | Открытое акционерное общество Конструкторско-производственное предприятие "Авиамотор" | Устройство для привода исполнительного механизма |
| DE102011076642A1 (de) * | 2011-05-27 | 2012-11-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
| US20140206897A1 (en) * | 2013-01-22 | 2014-07-24 | Saudi Basic Industries Corporation | Method for making methyl methacrylate from propionaldehyde and formaldehyde via oxidative esterification |
| ES2673104T3 (es) | 2013-04-19 | 2018-06-19 | Evonik Röhm Gmbh | Procedimiento para la preparación de metacrilato de metilo |
| CN103254091B (zh) * | 2013-05-21 | 2015-04-08 | 重庆紫光化工股份有限公司 | 一种甲基丙烯酰胺、甲基丙烯酸甲酯和甲基丙烯酸的联合生产方法 |
| US9580374B2 (en) * | 2013-09-26 | 2017-02-28 | Evonik Roehm Gmbh | Method for producing methacrolein and the conditioning/draining thereof for direct oxidative esterification |
| CN103846104A (zh) | 2014-02-17 | 2014-06-11 | 河南颖泰农化股份有限公司 | 以丙醛、甲醛为原料合成异丁烯醛用催化剂及其应用 |
-
2015
- 2015-09-16 EP EP15185441.1A patent/EP3144291A1/de not_active Withdrawn
-
2016
- 2016-09-09 JP JP2018513794A patent/JP6824253B2/ja active Active
- 2016-09-09 BR BR112018005075A patent/BR112018005075B8/pt active IP Right Grant
- 2016-09-09 EP EP16763037.5A patent/EP3350152B1/de active Active
- 2016-09-09 ES ES16763037T patent/ES2738990T3/es active Active
- 2016-09-09 KR KR1020187010571A patent/KR102638806B1/ko active Active
- 2016-09-09 RU RU2018113528A patent/RU2722364C2/ru active
- 2016-09-09 US US15/753,206 patent/US10479754B2/en active Active
- 2016-09-09 WO PCT/EP2016/071241 patent/WO2017046001A1/de not_active Ceased
- 2016-09-09 CN CN201680053437.9A patent/CN108137474B/zh active Active
- 2016-09-09 SG SG11201802077QA patent/SG11201802077QA/en unknown
- 2016-09-12 TW TW105129615A patent/TWI707842B/zh active
-
2018
- 2018-03-15 SA SA518391122A patent/SA518391122B1/ar unknown
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