DE3905786A1 - Verfahren und vorrichtung zur trennung von diacetylhaltigen gemischen aus methylethylketon, ethylacetat, ethanol und wasser sowie gegebenenfalls toluol und n-hexanen - Google Patents
Verfahren und vorrichtung zur trennung von diacetylhaltigen gemischen aus methylethylketon, ethylacetat, ethanol und wasser sowie gegebenenfalls toluol und n-hexanenInfo
- Publication number
- DE3905786A1 DE3905786A1 DE3905786A DE3905786A DE3905786A1 DE 3905786 A1 DE3905786 A1 DE 3905786A1 DE 3905786 A DE3905786 A DE 3905786A DE 3905786 A DE3905786 A DE 3905786A DE 3905786 A1 DE3905786 A1 DE 3905786A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- weight
- ethyl acetate
- column
- mixture
- 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 title claims abstract description 342
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 title claims abstract description 320
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 166
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 title claims abstract description 27
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 129
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000000605 extraction Methods 0.000 claims abstract description 58
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000284 extract Substances 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
- 238000004064 recycling Methods 0.000 claims abstract description 10
- 235000019439 ethyl acetate Nutrition 0.000 claims description 127
- 238000000926 separation method Methods 0.000 claims description 31
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 150000002170 ethers Chemical class 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 9
- SEUTYDPWWXFDLF-UHFFFAOYSA-N O.C(C)(=O)OCC.CC(=O)CC Chemical compound O.C(C)(=O)OCC.CC(=O)CC SEUTYDPWWXFDLF-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 239000001632 sodium acetate Substances 0.000 claims description 6
- 235000017281 sodium acetate Nutrition 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 239000011877 solvent mixture Substances 0.000 claims description 5
- 239000002351 wastewater Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
- -1 methyl tert-butyl Chemical group 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000013505 freshwater Substances 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims 2
- KMQWOHBEYVPGQJ-SNAWJCMRSA-N (e)-1-methoxybut-1-ene Chemical compound CC\C=C\OC KMQWOHBEYVPGQJ-SNAWJCMRSA-N 0.000 claims 1
- QHMVQKOXILNZQR-ONEGZZNKSA-N (e)-1-methoxyprop-1-ene Chemical compound CO\C=C\C QHMVQKOXILNZQR-ONEGZZNKSA-N 0.000 claims 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 claims 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 claims 1
- KBMDBLCFKPRPOC-UHFFFAOYSA-N 2-bromo-3,3,3-trifluoro-2-(trifluoromethyl)propanenitrile Chemical compound FC(F)(F)C(Br)(C#N)C(F)(F)F KBMDBLCFKPRPOC-UHFFFAOYSA-N 0.000 claims 1
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 claims 1
- FSGHEPDRMHVUCQ-UHFFFAOYSA-N 2-ethoxyprop-1-ene Chemical compound CCOC(C)=C FSGHEPDRMHVUCQ-UHFFFAOYSA-N 0.000 claims 1
- ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 238000007599 discharging Methods 0.000 claims 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 claims 1
- 230000009965 odorless effect Effects 0.000 claims 1
- 230000003134 recirculating effect Effects 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000895 extractive distillation Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000010887 waste solvent Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/84—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3905786A DE3905786A1 (de) | 1989-02-24 | 1989-02-24 | Verfahren und vorrichtung zur trennung von diacetylhaltigen gemischen aus methylethylketon, ethylacetat, ethanol und wasser sowie gegebenenfalls toluol und n-hexanen |
| EP90103447A EP0384458B1 (de) | 1989-02-24 | 1990-02-22 | Verfahren zur Trennung von diacetylhaltigen Gemischen aus Methylethylketon, Ethylacetat, Ethanol, Wasser sowie gegebenenfalls Toluol und n-Hexan |
| AT90103447T ATE98888T1 (de) | 1989-02-24 | 1990-02-22 | Verfahren zur trennung von diacetylhaltigen gemischen aus methylethylketon, ethylacetat, ethanol, wasser sowie gegebenenfalls toluol und n-hexan. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3905786A DE3905786A1 (de) | 1989-02-24 | 1989-02-24 | Verfahren und vorrichtung zur trennung von diacetylhaltigen gemischen aus methylethylketon, ethylacetat, ethanol und wasser sowie gegebenenfalls toluol und n-hexanen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3905786A1 true DE3905786A1 (de) | 1990-08-30 |
| DE3905786C2 DE3905786C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-06-13 |
Family
ID=6374870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3905786A Granted DE3905786A1 (de) | 1989-02-24 | 1989-02-24 | Verfahren und vorrichtung zur trennung von diacetylhaltigen gemischen aus methylethylketon, ethylacetat, ethanol und wasser sowie gegebenenfalls toluol und n-hexanen |
Country Status (3)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10336556A1 (de) * | 2003-08-05 | 2005-03-10 | Basf Ag | Destillatives Verfahren zur Trennung von engsiedenden oder azeotropen Gemischen unter Verwendung von ionischen Flüssigkeiten |
| CN100418602C (zh) * | 2003-12-01 | 2008-09-17 | 中国科学院生态环境研究中心 | 一次性固相微萃取离子液体涂层的制备 |
| CA2639030C (en) | 2008-07-23 | 2015-12-01 | Shaun T. Mesher | Mutual solvent system and method for improved oil and gas permeability in high temperature formations |
| CN107011171B (zh) * | 2017-04-14 | 2023-06-06 | 长江师范学院 | 变压精馏分离乙酸乙酯和正己烷共沸体系的系统和方法 |
| CN109111337B (zh) * | 2018-10-31 | 2024-04-09 | 福建技术师范学院 | 一种含甲苯、乙酸乙酯和乙醇等混合溶剂的分离设备及方法 |
| CN115093326A (zh) * | 2022-06-28 | 2022-09-23 | 青岛科技大学 | 一种萃取变压精馏分离乙酸乙酯-乙醇-丁酮混合物的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2649407A (en) * | 1952-03-14 | 1953-08-18 | Gulf Research Development Co | Separation of ethyl acetate and ethanol by azeotropic distillation with methanol |
| US2702783A (en) * | 1952-03-14 | 1955-02-22 | Gulf Research Development Co | Process of separating mixtures of organic compounds |
| US2862853A (en) * | 1954-06-03 | 1958-12-02 | Celanese Corp | Recovery of methyl ethyl ketone |
| DE3606121A1 (de) * | 1986-02-26 | 1987-08-27 | Texaco Ag | Verfahren zur kontinuierlichen abtrennung von wasser aus gemischen mit organischen substanzen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4470881A (en) * | 1981-03-23 | 1984-09-11 | Celanese Corporation | Separation of ethyl acetate from methyl ethyl ketone by extractive distillation |
-
1989
- 1989-02-24 DE DE3905786A patent/DE3905786A1/de active Granted
-
1990
- 1990-02-22 AT AT90103447T patent/ATE98888T1/de active
- 1990-02-22 EP EP90103447A patent/EP0384458B1/de not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2649407A (en) * | 1952-03-14 | 1953-08-18 | Gulf Research Development Co | Separation of ethyl acetate and ethanol by azeotropic distillation with methanol |
| US2702783A (en) * | 1952-03-14 | 1955-02-22 | Gulf Research Development Co | Process of separating mixtures of organic compounds |
| US2862853A (en) * | 1954-06-03 | 1958-12-02 | Celanese Corp | Recovery of methyl ethyl ketone |
| DE3606121A1 (de) * | 1986-02-26 | 1987-08-27 | Texaco Ag | Verfahren zur kontinuierlichen abtrennung von wasser aus gemischen mit organischen substanzen |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0384458A1 (de) | 1990-08-29 |
| ATE98888T1 (de) | 1994-01-15 |
| DE3905786C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-06-13 |
| EP0384458B1 (de) | 1993-12-22 |
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