TWI441798B - 用以純化不飽和化合物之方法及設備 - Google Patents
用以純化不飽和化合物之方法及設備 Download PDFInfo
- Publication number
- TWI441798B TWI441798B TW097144524A TW97144524A TWI441798B TW I441798 B TWI441798 B TW I441798B TW 097144524 A TW097144524 A TW 097144524A TW 97144524 A TW97144524 A TW 97144524A TW I441798 B TWI441798 B TW I441798B
- Authority
- TW
- Taiwan
- Prior art keywords
- evaporator
- mass flow
- added
- range
- purified
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 49
- 150000001875 compounds Chemical class 0.000 title claims description 37
- 239000010409 thin film Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- -1 glycol ester Chemical class 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 4
- 238000011068 loading method Methods 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 9
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 8
- 230000007774 longterm Effects 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- LQUFHIPRZXGNBM-UHFFFAOYSA-N 2,2,4,4-tetramethylazetidine Chemical compound CC1(C)CC(C)(C)N1 LQUFHIPRZXGNBM-UHFFFAOYSA-N 0.000 description 1
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 1
- VJMWPHGVWSFDFW-UHFFFAOYSA-N 2,2-dimethyl-4,4-dipropylazetidine Chemical compound CCCC1(CCC)CC(C)(C)N1 VJMWPHGVWSFDFW-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
- VGTGKCFPAUECEZ-UHFFFAOYSA-N 4-ethoxy-2,2,6,6-tetramethylpiperidine Chemical compound CCOC1CC(C)(C)NC(C)(C)C1 VGTGKCFPAUECEZ-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- MNDJKTIGCWCQIG-UHFFFAOYSA-N 4-n-naphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(C=CC=C2)C2=C1 MNDJKTIGCWCQIG-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical class [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 1
- OBBCYCYCTJQCCK-UHFFFAOYSA-L copper;n,n-diethylcarbamodithioate Chemical compound [Cu+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S OBBCYCYCTJQCCK-UHFFFAOYSA-L 0.000 description 1
- ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LXCJGJYAOVCKLO-UHFFFAOYSA-N n-cyclohexyl-n-hydroxynitrous amide Chemical compound O=NN(O)C1CCCCC1 LXCJGJYAOVCKLO-UHFFFAOYSA-N 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical compound O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/0088—Cascade evaporators
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/0094—Evaporating with forced circulation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/22—Evaporating by bringing a thin layer of the liquid into contact with a heated surface
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
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)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007056926A DE102007056926A1 (de) | 2007-11-23 | 2007-11-23 | Verfahren und Anlage zur Aufreinigung von ungesättigten Verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200942509A TW200942509A (en) | 2009-10-16 |
| TWI441798B true TWI441798B (zh) | 2014-06-21 |
Family
ID=40456713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097144524A TWI441798B (zh) | 2007-11-23 | 2008-11-18 | 用以純化不飽和化合物之方法及設備 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8394982B2 (enExample) |
| EP (1) | EP2209760B1 (enExample) |
| JP (1) | JP5631214B2 (enExample) |
| KR (2) | KR20150092372A (enExample) |
| CN (2) | CN101801905B (enExample) |
| DE (1) | DE102007056926A1 (enExample) |
| ES (1) | ES2408683T3 (enExample) |
| RU (1) | RU2492162C2 (enExample) |
| TW (1) | TWI441798B (enExample) |
| WO (1) | WO2009065633A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007056926A1 (de) * | 2007-11-23 | 2009-05-28 | Evonik Röhm Gmbh | Verfahren und Anlage zur Aufreinigung von ungesättigten Verbindungen |
| KR101278225B1 (ko) * | 2011-10-12 | 2013-06-24 | 박화성 | 2-하이드록시에틸메타아크릴레이트 정제장치 |
| KR101990058B1 (ko) | 2015-12-22 | 2019-06-17 | 주식회사 엘지화학 | (메트)아크릴산의 연속 회수 방법 |
| CN105854324B (zh) * | 2016-04-25 | 2018-10-30 | 钮德明 | 喷射式气液接触蒸发器 |
| CN105944398A (zh) * | 2016-06-28 | 2016-09-21 | 钮德明 | 外循环电磁热管加热真空蒸发器 |
| CN110227278A (zh) * | 2019-07-22 | 2019-09-13 | 余小海 | 一种甲苯蒸馏釜 |
| EP3904327A1 (de) | 2020-04-30 | 2021-11-03 | Röhm GmbH | Verfahren zur herstellung von hydroxyalkyl(meth)acrylsäureestern durch oxidative spaltung von methacrolein-acetalen |
| WO2023169863A1 (en) | 2022-03-08 | 2023-09-14 | Röhm Gmbh | Process for preparing high purity (meth)acrylates |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08245511A (ja) * | 1995-03-06 | 1996-09-24 | Daicel Chem Ind Ltd | （メタ）アクリレ―ト化合物の精製方法 |
| JP2002522576A (ja) * | 1998-08-06 | 2002-07-23 | アクゾ ノーベル ナムローゼ フェンノートシャップ | ジアルキルパーオキサイド化合物及び該化合物を化学反応を開始するために使用する方法 |
| JP3592970B2 (ja) * | 1999-10-07 | 2004-11-24 | 株式会社日本触媒 | ヒドロキシアルキル（メタ）アクリレートの精製方法 |
| DE10063175A1 (de) * | 2000-12-18 | 2002-06-20 | Basf Ag | Verfahren zur Herstellung von höheren (Meth)acrylsäureestern |
| JP4351827B2 (ja) * | 2002-03-28 | 2009-10-28 | 三菱レイヨン株式会社 | ヒドロキシアルキル（メタ）アクリレートの精製方法 |
| WO2003104300A1 (de) * | 2002-06-01 | 2003-12-18 | Basf Aktiengesellschaft | (meth)acrylester von polyalkoxyliertem trimethylolpropan |
| CN1220672C (zh) | 2002-11-25 | 2005-09-28 | 上海华谊丙烯酸有限公司 | （甲基）丙烯酸羟烷基酯的提纯方法 |
| DE10301007A1 (de) * | 2003-01-13 | 2004-07-22 | Röhm GmbH & Co. KG | Verbessertes Verfahren zur kontinuierlichen Herstellung von Alkyl(meth)acrylaten mit mehrfacher Katalysatorrezyklierung. |
| DE102006029318B3 (de) * | 2006-06-23 | 2007-10-11 | Röhm Gmbh | Verfahren zur kontinuierlichen Herstellung von ungesättigten Carbonsäureanhydriden |
| DE102007056926A1 (de) * | 2007-11-23 | 2009-05-28 | Evonik Röhm Gmbh | Verfahren und Anlage zur Aufreinigung von ungesättigten Verbindungen |
-
2007
- 2007-11-23 DE DE102007056926A patent/DE102007056926A1/de not_active Withdrawn
-
2008
- 2008-08-29 KR KR1020157020800A patent/KR20150092372A/ko not_active Ceased
- 2008-08-29 JP JP2010534422A patent/JP5631214B2/ja active Active
- 2008-08-29 ES ES08803358T patent/ES2408683T3/es active Active
- 2008-08-29 CN CN2008801074221A patent/CN101801905B/zh active Active
- 2008-08-29 WO PCT/EP2008/061359 patent/WO2009065633A1/de not_active Ceased
- 2008-08-29 RU RU2010125500/04A patent/RU2492162C2/ru active
- 2008-08-29 EP EP08803358A patent/EP2209760B1/de active Active
- 2008-08-29 KR KR1020107008903A patent/KR101565179B1/ko active Active
- 2008-08-29 US US12/677,540 patent/US8394982B2/en active Active
- 2008-11-14 CN CNA2008101761837A patent/CN101440033A/zh active Pending
- 2008-11-18 TW TW097144524A patent/TWI441798B/zh active
-
2012
- 2012-11-06 US US13/669,607 patent/US9259664B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| HK1143970A1 (en) | 2011-01-21 |
| EP2209760B1 (de) | 2013-03-13 |
| RU2010125500A (ru) | 2011-12-27 |
| KR20100093031A (ko) | 2010-08-24 |
| US9259664B2 (en) | 2016-02-16 |
| KR101565179B1 (ko) | 2015-11-02 |
| RU2492162C2 (ru) | 2013-09-10 |
| ES2408683T3 (es) | 2013-06-21 |
| EP2209760A1 (de) | 2010-07-28 |
| CN101801905B (zh) | 2013-08-21 |
| US8394982B2 (en) | 2013-03-12 |
| JP2011504475A (ja) | 2011-02-10 |
| CN101440033A (zh) | 2009-05-27 |
| US20100217030A1 (en) | 2010-08-26 |
| US20130066104A1 (en) | 2013-03-14 |
| KR20150092372A (ko) | 2015-08-12 |
| CN101801905A (zh) | 2010-08-11 |
| TW200942509A (en) | 2009-10-16 |
| JP5631214B2 (ja) | 2014-11-26 |
| DE102007056926A1 (de) | 2009-05-28 |
| WO2009065633A1 (de) | 2009-05-28 |
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