RU2492162C2 - Способы и устройство для очистки ненасыщенных соединений - Google Patents
Способы и устройство для очистки ненасыщенных соединений Download PDFInfo
- Publication number
- RU2492162C2 RU2492162C2 RU2010125500/04A RU2010125500A RU2492162C2 RU 2492162 C2 RU2492162 C2 RU 2492162C2 RU 2010125500/04 A RU2010125500/04 A RU 2010125500/04A RU 2010125500 A RU2010125500 A RU 2010125500A RU 2492162 C2 RU2492162 C2 RU 2492162C2
- Authority
- RU
- Russia
- Prior art keywords
- evaporator
- evaporation
- mass flow
- evaporators
- condensed
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 57
- 150000001875 compounds Chemical class 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000001704 evaporation Methods 0.000 claims abstract description 21
- 230000008020 evaporation Effects 0.000 claims abstract description 21
- 238000000746 purification Methods 0.000 claims abstract description 11
- 238000009434 installation Methods 0.000 claims description 50
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- -1 glycol ethers Chemical class 0.000 claims description 11
- 239000012071 phase Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 150000002334 glycols Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000010408 film Substances 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 11
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 9
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 230000002045 lasting effect Effects 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000012935 Averaging Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
- 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
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-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
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-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
- JQTYAZKTBXWQOM-UHFFFAOYSA-N 4-n-octan-2-yl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CCCCCC)=CC=C1NC1=CC=CC=C1 JQTYAZKTBXWQOM-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-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
- RPDUDBYMNGAHEM-UHFFFAOYSA-N PROXYL Chemical group CC1(C)CCC(C)(C)N1[O] RPDUDBYMNGAHEM-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
- 150000001412 amines Chemical class 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- PYYXCLLGYQVCJB-UHFFFAOYSA-N n-cyclohexyl-n-hydroxynitramide Chemical compound [O-][N+](=O)N(O)C1CCCCC1 PYYXCLLGYQVCJB-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
- 150000002989 phenols Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Images
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007056926A DE102007056926A1 (de) | 2007-11-23 | 2007-11-23 | Verfahren und Anlage zur Aufreinigung von ungesättigten Verbindungen |
| DE102007056926.4 | 2007-11-23 | ||
| PCT/EP2008/061359 WO2009065633A1 (de) | 2007-11-23 | 2008-08-29 | Verfahren und anlage zur aufreinigung von ungesättigten verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010125500A RU2010125500A (ru) | 2011-12-27 |
| RU2492162C2 true RU2492162C2 (ru) | 2013-09-10 |
Family
ID=40456713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010125500/04A RU2492162C2 (ru) | 2007-11-23 | 2008-08-29 | Способы и устройство для очистки ненасыщенных соединений |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8394982B2 (enExample) |
| EP (1) | EP2209760B1 (enExample) |
| JP (1) | JP5631214B2 (enExample) |
| KR (2) | KR101565179B1 (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 |
| CN118804909A (zh) | 2022-03-08 | 2024-10-18 | 罗姆化学有限责任公司 | 制备高纯度(甲基)丙烯酸酯的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1502601A (zh) * | 2002-11-25 | 2004-06-09 | 上海高桥石化丙烯酸厂 | （甲基）丙烯酸羟烷基酯的提纯方法 |
| RU2005100767A (ru) * | 2002-06-11 | 2005-08-10 | Басф Акциенгезелльшафт (De) | Сложный (мет)акриловый эфир полиалкоксилированного триметилпропана |
Family Cites Families (8)
| 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 |
| ATE308572T1 (de) * | 1998-08-06 | 2005-11-15 | Akzo Nobel Nv | Verfahren zur initiierung einer chemischen reaktion unter verwendung vom dialkylperoxid- verbindungen |
| 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 |
| 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 RU RU2010125500/04A patent/RU2492162C2/ru active
- 2008-08-29 KR KR1020107008903A patent/KR101565179B1/ko active Active
- 2008-08-29 US US12/677,540 patent/US8394982B2/en active Active
- 2008-08-29 WO PCT/EP2008/061359 patent/WO2009065633A1/de not_active Ceased
- 2008-08-29 ES ES08803358T patent/ES2408683T3/es active Active
- 2008-08-29 CN CN2008801074221A patent/CN101801905B/zh active Active
- 2008-08-29 KR KR1020157020800A patent/KR20150092372A/ko not_active Ceased
- 2008-08-29 EP EP08803358A patent/EP2209760B1/de active Active
- 2008-08-29 JP JP2010534422A patent/JP5631214B2/ja 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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2005100767A (ru) * | 2002-06-11 | 2005-08-10 | Басф Акциенгезелльшафт (De) | Сложный (мет)акриловый эфир полиалкоксилированного триметилпропана |
| CN1502601A (zh) * | 2002-11-25 | 2004-06-09 | 上海高桥石化丙烯酸厂 | （甲基）丙烯酸羟烷基酯的提纯方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009065633A1 (de) | 2009-05-28 |
| TWI441798B (zh) | 2014-06-21 |
| ES2408683T3 (es) | 2013-06-21 |
| KR101565179B1 (ko) | 2015-11-02 |
| US9259664B2 (en) | 2016-02-16 |
| CN101440033A (zh) | 2009-05-27 |
| CN101801905A (zh) | 2010-08-11 |
| DE102007056926A1 (de) | 2009-05-28 |
| KR20100093031A (ko) | 2010-08-24 |
| JP5631214B2 (ja) | 2014-11-26 |
| CN101801905B (zh) | 2013-08-21 |
| RU2010125500A (ru) | 2011-12-27 |
| EP2209760B1 (de) | 2013-03-13 |
| HK1143970A1 (en) | 2011-01-21 |
| US20100217030A1 (en) | 2010-08-26 |
| US20130066104A1 (en) | 2013-03-14 |
| KR20150092372A (ko) | 2015-08-12 |
| TW200942509A (en) | 2009-10-16 |
| JP2011504475A (ja) | 2011-02-10 |
| EP2209760A1 (de) | 2010-07-28 |
| US8394982B2 (en) | 2013-03-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD4A | Correction of name of patent owner | ||
| PD4A | Correction of name of patent owner | ||
| PC41 | Official registration of the transfer of exclusive right |
Effective date: 20201217 |