CN108373409A - 甲基丙烯酸和甲基丙烯酸酯的制备方法 - Google Patents
甲基丙烯酸和甲基丙烯酸酯的制备方法 Download PDFInfo
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- CN108373409A CN108373409A CN201810206739.6A CN201810206739A CN108373409A CN 108373409 A CN108373409 A CN 108373409A CN 201810206739 A CN201810206739 A CN 201810206739A CN 108373409 A CN108373409 A CN 108373409A
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- 238000007445 Chromatographic isolation Methods 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
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- 239000005977 Ethylene Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- GCNLQHANGFOQKY-UHFFFAOYSA-N [C+4].[O-2].[O-2].[Ti+4] Chemical compound [C+4].[O-2].[O-2].[Ti+4] GCNLQHANGFOQKY-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- VPSLGSSVPWVZFG-UHFFFAOYSA-N butan-2-yl propanoate Chemical compound CCC(C)OC(=O)CC VPSLGSSVPWVZFG-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
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000007084 catalytic combustion reaction Methods 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- KTIGDTYUEDDRFL-UHFFFAOYSA-N chloromethane prop-1-ene Chemical group [H]CCl.[H]C=C([H])C KTIGDTYUEDDRFL-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
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- 150000001924 cycloalkanes Chemical class 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
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- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
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- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000011144 upstream manufacturing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0036—Crystallisation on to a bed of product crystals; Seeding
-
- 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
- B01D9/0045—Washing of crystals, e.g. in wash columns
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
-
- 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
-
- 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
-
- 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
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- 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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810206739.6A CN108373409A (zh) | 2011-09-16 | 2011-09-16 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201180073459.9A CN103827071A (zh) | 2011-09-16 | 2011-09-16 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
| CN201810206739.6A CN108373409A (zh) | 2011-09-16 | 2011-09-16 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
| PCT/CN2011/079774 WO2013037134A1 (en) | 2011-09-16 | 2011-09-16 | Process for preparation of methacrylic acid and methacrylic acid esters |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180073459.9A Division CN103827071A (zh) | 2011-09-16 | 2011-09-16 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
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| CN108373409A true CN108373409A (zh) | 2018-08-07 |
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| CN201810206739.6A Pending CN108373409A (zh) | 2011-09-16 | 2011-09-16 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
| CN201180073459.9A Pending CN103827071A (zh) | 2011-09-16 | 2011-09-16 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180073459.9A Pending CN103827071A (zh) | 2011-09-16 | 2011-09-16 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JP6008969B2 (ja) |
| KR (1) | KR101877597B1 (ja) |
| CN (2) | CN108373409A (ja) |
| MY (1) | MY161504A (ja) |
| SA (1) | SA112330845B1 (ja) |
| SG (1) | SG2014012587A (ja) |
| TW (1) | TWI627161B (ja) |
| WO (1) | WO2013037134A1 (ja) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013037136A1 (en) * | 2011-09-16 | 2013-03-21 | Evonik Roehm Gmbh | Process for preparation of methacrylic acid and methacrylic acid esters |
| MY165642A (en) * | 2011-09-16 | 2018-04-18 | Evonik Roehm Gmbh | Process for preparation of methacrylic acid and methacrylic acid ester |
| KR101628287B1 (ko) * | 2013-07-22 | 2016-06-08 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 및 장치 |
| WO2015012551A1 (ko) * | 2013-07-22 | 2015-01-29 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 및 장치 |
| US9718756B2 (en) * | 2013-07-23 | 2017-08-01 | Lg Chem, Ltd. | Method for continuously recovering (meth)acrylic acid and apparatus for the method |
| KR101601938B1 (ko) | 2013-08-30 | 2016-03-09 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 및 회수 장치 |
| WO2024049105A1 (ko) * | 2022-08-30 | 2024-03-07 | 주식회사 엘지화학 | 고순도 (메트)아크릴산의 제조방법 |
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| CN101497563A (zh) * | 2008-01-30 | 2009-08-05 | 赢创罗姆有限责任公司 | 制备高纯度甲基丙烯酸的方法 |
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| DE19709392A1 (de) * | 1997-03-07 | 1998-09-10 | Basf Ag | Verfahren zur Extraktion von (Meth)acrylsäure |
| JP2002128728A (ja) * | 2000-10-19 | 2002-05-09 | Mitsubishi Rayon Co Ltd | メタクリル酸の精製方法 |
| JP2002193875A (ja) * | 2000-12-27 | 2002-07-10 | Mitsubishi Rayon Co Ltd | メタクリル酸の回収方法 |
| DE10242746B4 (de) * | 2002-09-13 | 2010-07-01 | Evonik Degussa Gmbh | Waschvorrichtung, ein Verfahren zur Aufreinigung eines Waschguts sowie die Verwendung der Waschvorrichtung |
| EP1995231B1 (en) * | 2007-05-25 | 2013-11-20 | Evonik Röhm GmbH | Process for preparation of methyl methacrylate using recycled methanol |
| WO2013037136A1 (en) * | 2011-09-16 | 2013-03-21 | Evonik Roehm Gmbh | Process for preparation of methacrylic acid and methacrylic acid esters |
| MY165642A (en) * | 2011-09-16 | 2018-04-18 | Evonik Roehm Gmbh | Process for preparation of methacrylic acid and methacrylic acid ester |
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2011
- 2011-09-16 JP JP2014530068A patent/JP6008969B2/ja active Active
- 2011-09-16 MY MYPI2014000746A patent/MY161504A/en unknown
- 2011-09-16 CN CN201810206739.6A patent/CN108373409A/zh active Pending
- 2011-09-16 KR KR1020147006620A patent/KR101877597B1/ko active IP Right Grant
- 2011-09-16 WO PCT/CN2011/079774 patent/WO2013037134A1/en active Application Filing
- 2011-09-16 CN CN201180073459.9A patent/CN103827071A/zh active Pending
- 2011-09-16 SG SG2014012587A patent/SG2014012587A/en unknown
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2012
- 2012-09-12 TW TW101133297A patent/TWI627161B/zh not_active IP Right Cessation
- 2012-09-15 SA SA112330845A patent/SA112330845B1/ar unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54119412A (en) * | 1978-03-06 | 1979-09-17 | Mitsubishi Chem Ind Ltd | Purification of methacrylic acid |
| CN101497563A (zh) * | 2008-01-30 | 2009-08-05 | 赢创罗姆有限责任公司 | 制备高纯度甲基丙烯酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201329035A (zh) | 2013-07-16 |
| KR101877597B1 (ko) | 2018-07-12 |
| SA112330845B1 (ar) | 2015-07-07 |
| KR20140060528A (ko) | 2014-05-20 |
| JP6008969B2 (ja) | 2016-10-19 |
| JP2014528935A (ja) | 2014-10-30 |
| SG2014012587A (en) | 2014-06-27 |
| CN103827071A (zh) | 2014-05-28 |
| MY161504A (en) | 2017-04-14 |
| TWI627161B (zh) | 2018-06-21 |
| WO2013037134A1 (en) | 2013-03-21 |
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