CN110709149A - 纯化(甲基)丙烯酸酯的方法 - Google Patents
纯化(甲基)丙烯酸酯的方法 Download PDFInfo
- Publication number
- CN110709149A CN110709149A CN201880035815.XA CN201880035815A CN110709149A CN 110709149 A CN110709149 A CN 110709149A CN 201880035815 A CN201880035815 A CN 201880035815A CN 110709149 A CN110709149 A CN 110709149A
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- Prior art keywords
- column
- meth
- section
- purified
- wall
- Prior art date
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims description 49
- 238000000746 purification Methods 0.000 claims abstract description 40
- 239000011541 reaction mixture Substances 0.000 claims abstract description 27
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 24
- 238000002955 isolation Methods 0.000 claims abstract description 3
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical group CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 33
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 17
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 14
- -1 acrylic ester Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- 239000012264 purified product Substances 0.000 claims description 11
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000005194 fractionation Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
- HZLFQUWNZMMHQM-UHFFFAOYSA-N piperazin-1-ylmethanol Chemical compound OCN1CCNCC1 HZLFQUWNZMMHQM-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 19
- 238000000926 separation method Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 238000004064 recycling Methods 0.000 abstract description 3
- 238000010924 continuous production Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 29
- 238000004821 distillation Methods 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 20
- 229960002887 deanol Drugs 0.000 description 18
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 16
- 239000006227 byproduct Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 11
- 239000012535 impurity Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229950000688 phenothiazine Drugs 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000005265 energy consumption Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 241000183024 Populus tremula Species 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 229960003505 mequinol Drugs 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- UVSPBAFXKQMDBG-UHFFFAOYSA-N 2-(dimethylamino)ethyl propanoate Chemical compound CCC(=O)OCCN(C)C UVSPBAFXKQMDBG-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- RPZAHMQZOPZKFV-UHFFFAOYSA-N CN(C)CCOC(C(=O)OCCN(C)C)C Chemical compound CN(C)CCOC(C(=O)OCCN(C)C)C RPZAHMQZOPZKFV-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241001045956 Psorothamnus Species 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/141—Fractional distillation or use of a fractionation or rectification column where at least one distillation column contains at least one dividing wall
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1757038A FR3069538B1 (fr) | 2017-07-25 | 2017-07-25 | Procede de purification d'esters (meth)acryliques. |
| FR1757038 | 2017-07-25 | ||
| PCT/FR2018/051645 WO2019020889A1 (fr) | 2017-07-25 | 2018-07-03 | Procede de purification d'esters (meth)acryliques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110709149A true CN110709149A (zh) | 2020-01-17 |
Family
ID=60138503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880035815.XA Pending CN110709149A (zh) | 2017-07-25 | 2018-07-03 | 纯化(甲基)丙烯酸酯的方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11261150B2 (enExample) |
| EP (1) | EP3658249B1 (enExample) |
| JP (1) | JP7079272B2 (enExample) |
| KR (1) | KR102610677B1 (enExample) |
| CN (1) | CN110709149A (enExample) |
| FR (1) | FR3069538B1 (enExample) |
| SA (1) | SA519410648B1 (enExample) |
| WO (1) | WO2019020889A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116323537B (zh) * | 2021-09-14 | 2025-07-22 | 株式会社Lg化学 | 多组分混合物分离系统 |
| AU2024209766A1 (en) * | 2023-01-20 | 2025-07-31 | Kemira Oyj | Surfactant compositions derived from waste streams, and methods |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040204614A1 (en) * | 2001-07-05 | 2004-10-14 | Catalytic Distillation Technologies | Process and apparatus for catalytic distillations |
| JP2005239564A (ja) * | 2004-02-24 | 2005-09-08 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸エステルの製造方法 |
| US20090139852A1 (en) * | 2007-12-04 | 2009-06-04 | Vannuland Marco L | Separation Method And Apparatus |
| CN102639679A (zh) * | 2009-12-01 | 2012-08-15 | 埃克森美孚研究工程公司 | 使用分隔壁塔分馏器的两阶段加氢加工 |
| CN203494195U (zh) * | 2013-09-24 | 2014-03-26 | 中国石油化工股份有限公司 | 用于共沸精馏的分壁精馏塔 |
| CN104918911A (zh) * | 2012-12-17 | 2015-09-16 | 阿肯马法国公司 | 丙烯酸烷基酯的制备方法 |
| CN106748758A (zh) * | 2016-12-21 | 2017-05-31 | 常州大学 | 热泵分隔壁反应精馏塔制备乙酸异丙酯的装置 |
| CN106861353A (zh) * | 2015-12-14 | 2017-06-20 | 财团法人工业技术研究院 | 分离装置 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5035214A (en) * | 1990-02-16 | 1991-07-30 | Siemens Automotive L.P. | Engine throttle blade sealing |
| JPH0613462B2 (ja) * | 1990-09-25 | 1994-02-23 | 東亞合成化学工業株式会社 | ジメチルアミノエチルアクリレートの貯蔵方法 |
| FR2777561B1 (fr) | 1998-04-21 | 2000-06-02 | Atochem Elf Sa | Procede de fabrication en continu de (meth)acrylates de dialkylaminoalkyle |
| DE10127938A1 (de) | 2001-06-08 | 2002-07-25 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10127939A1 (de) | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| SG190284A1 (en) * | 2010-11-22 | 2013-06-28 | Rohm & Haas | Acrylate production process |
| KR101496488B1 (ko) * | 2010-12-29 | 2015-02-26 | 주식회사 엘지화학 | 고순도 2-에틸헥실-아크릴레이트 생산을 위한 분리벽형 증류탑 및 이를 이용한 제조방법 |
| FR2985999B1 (fr) | 2012-01-23 | 2014-01-31 | Arkema France | Procede de production d'acrylate de 2-octyle par transesterification |
| KR101583145B1 (ko) * | 2013-07-18 | 2016-01-07 | 주식회사 엘지화학 | 증류 장치 |
-
2017
- 2017-07-25 FR FR1757038A patent/FR3069538B1/fr active Active
-
2018
- 2018-07-03 WO PCT/FR2018/051645 patent/WO2019020889A1/fr not_active Ceased
- 2018-07-03 EP EP18749024.8A patent/EP3658249B1/fr active Active
- 2018-07-03 US US16/616,528 patent/US11261150B2/en active Active
- 2018-07-03 JP JP2019563593A patent/JP7079272B2/ja active Active
- 2018-07-03 KR KR1020197035333A patent/KR102610677B1/ko active Active
- 2018-07-03 CN CN201880035815.XA patent/CN110709149A/zh active Pending
-
2019
- 2019-11-27 SA SA519410648A patent/SA519410648B1/ar unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040204614A1 (en) * | 2001-07-05 | 2004-10-14 | Catalytic Distillation Technologies | Process and apparatus for catalytic distillations |
| JP2005239564A (ja) * | 2004-02-24 | 2005-09-08 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸エステルの製造方法 |
| US20090139852A1 (en) * | 2007-12-04 | 2009-06-04 | Vannuland Marco L | Separation Method And Apparatus |
| CN102639679A (zh) * | 2009-12-01 | 2012-08-15 | 埃克森美孚研究工程公司 | 使用分隔壁塔分馏器的两阶段加氢加工 |
| CN104918911A (zh) * | 2012-12-17 | 2015-09-16 | 阿肯马法国公司 | 丙烯酸烷基酯的制备方法 |
| CN203494195U (zh) * | 2013-09-24 | 2014-03-26 | 中国石油化工股份有限公司 | 用于共沸精馏的分壁精馏塔 |
| CN106861353A (zh) * | 2015-12-14 | 2017-06-20 | 财团法人工业技术研究院 | 分离装置 |
| CN106748758A (zh) * | 2016-12-21 | 2017-05-31 | 常州大学 | 热泵分隔壁反应精馏塔制备乙酸异丙酯的装置 |
Non-Patent Citations (2)
| Title |
|---|
| NORBERT ASPRION ET AL: "Dividing wall columns: Fundamentals and recent advances", 《CHEMICAL ENGINEERING AND PROCESSING》 * |
| 裘兆蓉等: "国内外分隔壁精馏塔现状与发展趋势", 《江苏工业学院学报》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3658249A1 (fr) | 2020-06-03 |
| FR3069538B1 (fr) | 2020-05-15 |
| BR112019024485A2 (pt) | 2020-06-16 |
| US11261150B2 (en) | 2022-03-01 |
| KR20200033797A (ko) | 2020-03-30 |
| KR102610677B1 (ko) | 2023-12-05 |
| FR3069538A1 (fr) | 2019-02-01 |
| JP7079272B2 (ja) | 2022-06-01 |
| US20210300857A1 (en) | 2021-09-30 |
| SA519410648B1 (ar) | 2023-01-10 |
| JP2020528398A (ja) | 2020-09-24 |
| EP3658249B1 (fr) | 2021-10-27 |
| WO2019020889A1 (fr) | 2019-01-31 |
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