WO1999005137A1 - Verfahren zur abtrennung von trioxan - Google Patents
Verfahren zur abtrennung von trioxan Download PDFInfo
- Publication number
- WO1999005137A1 WO1999005137A1 PCT/EP1998/004094 EP9804094W WO9905137A1 WO 1999005137 A1 WO1999005137 A1 WO 1999005137A1 EP 9804094 W EP9804094 W EP 9804094W WO 9905137 A1 WO9905137 A1 WO 9905137A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- trioxane
- mixture
- formaldehyde
- water
- stream
- Prior art date
Links
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002955 isolation Methods 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000005373 pervaporation Methods 0.000 claims abstract description 17
- 239000012466 permeate Substances 0.000 claims abstract description 9
- 239000012528 membrane Substances 0.000 claims description 12
- 239000012465 retentate Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- -1 polydimethylsiloxane Polymers 0.000 claims description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
- 229920002614 Polyether block amide Polymers 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VPRUMANMDWQMNF-UHFFFAOYSA-N phenylethane boronic acid Chemical compound OB(O)CCC1=CC=CC=C1 VPRUMANMDWQMNF-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/362—Pervaporation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
- C07D323/04—Six-membered rings
- C07D323/06—Trioxane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S159/00—Concentrating evaporators
- Y10S159/27—Micropores
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S159/00—Concentrating evaporators
- Y10S159/28—Porous member
Definitions
- the invention relates to a process for separating trioxane from an aqueous mixture which consists essentially of trioxane, formaldehyde and water.
- trioxane creates an azeotropic mixture that consists essentially of trioxane, water and formaldehyde.
- Trioxane is extracted from this mixture with the aid of an entrainer, e.g. chlorine-containing entraining agents such as methylene chloride or benzene are separated off.
- an entrainer e.g. chlorine-containing entraining agents such as methylene chloride or benzene are separated off.
- Other constituents of the mixture in minor amounts are usually formic acid, methylal and dimethoxy dimethyl ester.
- the entrainer is recovered and returned to the extractive distillation.
- large amounts of entraining agents have to be used and recovered with high energy expenditure. Inevitable emissions have to be disposed of, since methylene chloride and benzene are classified as dangerous pollutants.
- EP-A 596 381 discloses a process for the separation of trioxane which removes water from the azeotropic mixture by pervaporation.
- aqueous mixture consisting of 65% by weight of trioxane, 27.5% by weight of water and 7.5% by weight of formaldehyde is in a pervaporation unit 2 which has a membrane 3 made of polyvinyl alcohol from Sulzer Chemtech GmbH -Membrantechnik, D-66540 Neun Wegn / Saar contains, water (line 4) withdrawn.
- the separation takes place at 90 ° C.
- the pressure on the retentate side 5 is 1 bar, on the permeate side 6 50 mbar.
- the permeate obtained is water and the retentate is a mixture of 84% by weight of trioxane, 10% by weight of formaldehyde and 6% by weight of water (line 7).
- the retentate is decomposed in a rectification column 8 under normal pressure into pure trioxane (bottom product, line 9) and an azeotropic mixture of trioxane, formaldehyde and water (top product, line 10).
- This process has the disadvantage that it does not offer complete trioxane workup. A return of the column stream 10, for example before the pervaporation, would not make sense, since formaldehyde would accumulate.
- the object of the present invention was to provide a process for separating trioxane from this azeotropic mixture, which offers the most complete possible possible recovery of the trioxane.
- trioxane is removed from the mixture by pervaporation and the trioxane-enriched mixture (permeate) by rectification in trioxane and an azeotropic mixture of trioxane, water and formaldehyde.
- the process according to the invention offers the advantages of a largely quantitative work-up of the reactor discharge with the most complete possible recovery of the trioxane and formaldehyde. No other feedstocks are required.
- Stream 1 represents the reactor discharge which is produced in the production of trioxane. As a rule, this consists essentially of 35 to 45% by weight of trioxane, 35 to 45% by weight of water and 15 to 30% by weight of formaldehyde. Stream 1 is passed into a 1st rectification column K1, in which there is a separation into 2 fractions, stream 2 containing a mixture of water and formaldehyde and stream 3 containing the azeotropic mixture.
- the distillation is preferably carried out in a rectification column K1, which can have up to 60 trays. As a rule, the distillation is carried out under normal pressure.
- Stream 2 is then returned to the formaldehyde concentration.
- the azeotropic mixture (stream 3) is transferred to a vaporization unit (PV) which contains suitable membranes for organophilic pervaporation.
- the membranes used are usually pore-free polymer membranes, in which the permeating component dissolves and diffuses through the membrane.
- Suitable membranes are, for example, those made from polydimethylsiloxane and polyether amide block copolymers.
- the polydimethylsiloxane membrane preferably contains a hydrophobic zeolite.
- the thickness of the membrane is preferably from 5 to 200 ⁇ m, preferably from 50 to 150 ⁇ m.
- Such membranes are commercially available under the trade names Pervap® 1070 from Sulzer Chemtech GmbH-Membrantechnik and PEBA 40 from GSE (Gesellschaft für Spezialfolienponent).
- the pervaporation is preferably carried out at temperatures from 70 to 120 ° C., preferably from 80 to 90 ° C. and a pressure of 1 to 3, preferably 1 to 1.5 bar on the retentate side and 10 to 150 mbar, preferably 10 to 20 mbar on the permeate side.
- the stream 5 depleted in trioxane (retentate) is returned to the first distillation column K 1, while the stream 6 enriched with trioxane (permeate) is fed into a second distillation column K 2, in which rectification then takes place.
- the trioxane fraction is the product and (stream 7) is fed into a reactor in which polyoxymethylenes are produced from trioxane.
- aqueous mixture consisting of 40% by weight of trioxane, 40% by weight of water and 20% by weight of formaldehyde was in a first distillation column (Kl, 25 stages) under normal pressure in a water / formaldehyde stream (stream 2) and separated into an azeotropic mixture (stream 3).
- Stream 3 was passed into the pervaporation unit, which contained a membrane of polydimethylsiloxane with a hydrophobic zeolite.
- the total thickness was 200 ⁇ m
- the support layer consisted of polyacrylonitrile.
- the thickness of the separating layer was 15-20 ⁇ m. (Membrane Pervap® 1070 from Sulzer Chemtech GmbH-membrane technology). The separation took place at 80 ° C.
- the pressure on the retentate side (5) was 1 bar and on the permeate side (6) 10 mbar.
- the stream depleted in trioxane (stream 5) was fed to the first distillation column (K1).
- the bottom stream from this distillation column was passed on to the formaldehyde concentration.
- trioxane 98.4% by weight of trioxane, based on 3200 kg of trioxane used - 100% by weight of formaldehyde, based on 1600 kg of formaldehyde used
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000504133A JP2001510839A (ja) | 1997-07-26 | 1998-07-02 | トリオキサンの単離 |
KR1020007000817A KR20010022244A (ko) | 1997-07-26 | 1998-07-02 | 트리옥산의 단리법 |
PL98338381A PL338381A1 (en) | 1997-07-26 | 1998-07-02 | Method of isolating trioxane |
EP98939607A EP1001954A1 (de) | 1997-07-26 | 1998-07-02 | Verfahren zur abtrennung von trioxan |
US09/462,627 US6200429B1 (en) | 1997-07-26 | 1998-07-02 | Method for trioxane isolation |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19732291A DE19732291A1 (de) | 1997-07-26 | 1997-07-26 | Verfahren zur Abtrennung von Trioxan |
DE19732291.3 | 1997-07-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999005137A1 true WO1999005137A1 (de) | 1999-02-04 |
Family
ID=7837039
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/004094 WO1999005137A1 (de) | 1997-07-26 | 1998-07-02 | Verfahren zur abtrennung von trioxan |
Country Status (8)
Country | Link |
---|---|
US (1) | US6200429B1 (de) |
EP (1) | EP1001954A1 (de) |
JP (1) | JP2001510839A (de) |
KR (1) | KR20010022244A (de) |
CN (1) | CN1264374A (de) |
DE (1) | DE19732291A1 (de) |
PL (1) | PL338381A1 (de) |
WO (1) | WO1999005137A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005063733A1 (de) * | 2003-12-23 | 2005-07-14 | Basf Aktiengesellschaft | Verfahren zur abtrennung von trioxan aus einem trioxan/formaldehyd/wasser-gemisch mittels druckwechsel-rektifikation |
WO2006018302A1 (de) * | 2004-08-19 | 2006-02-23 | Basf Aktiengesellschaft | Verfahren zur destillativen abtrennung von rein-trioxan |
WO2006040065A1 (de) * | 2004-10-08 | 2006-04-20 | Ticona Gmbh | Verfahren zur herstellung und entwässerung von zyklischen formalen |
WO2006040064A1 (de) * | 2004-10-08 | 2006-04-20 | Ticona Gmbh | Verfahren zur herstellung und entwässerung von zyklischen formalen |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE457192T1 (de) * | 2001-10-19 | 2010-02-15 | Mitsubishi Chem Corp | Destillationsvorrichtung für wasserlösliche organische stoffe |
US6644921B2 (en) | 2001-11-08 | 2003-11-11 | General Electric Company | Cooling passages and methods of fabrication |
DE10361518A1 (de) * | 2003-12-23 | 2005-07-28 | Basf Ag | Verfahren zur Abtrennung von Trioxan aus einem Trioxan/Formaldehyd/Wasser-Gemisch |
DE102004051118A1 (de) | 2004-10-20 | 2006-04-27 | Basf Ag | Verfahren zur Herstellung von Trioxan |
DE102005037294A1 (de) * | 2005-08-08 | 2007-02-15 | Basf Ag | Integriertes Verfahren zur Herstellung von Trioxan aus Formaldehyd |
DE102005051974A1 (de) * | 2005-10-31 | 2007-05-03 | Basf Ag | Verfahren zur Herstellung von Trioxan und mindestens einem Comonomer |
CA2654892A1 (en) * | 2006-06-12 | 2007-12-21 | Basf Se | Integrated method for the preparation of trioxane from formaldehyde |
MY153212A (en) | 2007-01-25 | 2015-01-29 | Basf Se | Method for separating trioxane from a triozane/formaldehyde/water mixture by means of pressure change rectification |
US20100130756A1 (en) * | 2007-03-30 | 2010-05-27 | Basf Se | Method for producing trioxane from trioxymethylene glycol dimethyl ether |
JP2010523483A (ja) * | 2007-03-30 | 2010-07-15 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリオキシジアルキルエーテルからの環状ホルムアルデヒド誘導体の製造方法 |
CN101121709B (zh) * | 2007-09-17 | 2010-08-11 | 浙江三博聚合物有限公司 | 三聚甲醛合成后的初步提浓、净化的方法 |
US8350063B2 (en) | 2007-10-09 | 2013-01-08 | Basf Se | Method for separating tioxane from a trioxane/formaldehyde/water mixture by means of pressure change rectification |
JP5355587B2 (ja) * | 2007-12-19 | 2013-11-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 粗トリオキサンの製造法 |
WO2011067229A1 (de) | 2009-12-01 | 2011-06-09 | Basf Se | Verwendung von trioxan, gewonnen aus einem verfahren zur abtrennung von trioxan aus einem trioxan/formaldehyd/wasser - gemisch, zur herstellung von polyoxymethylendialkylethern |
WO2013121594A1 (en) * | 2012-02-17 | 2013-08-22 | Mitsubishi Rayon Co., Ltd. | Dehydration of water containing source of formaldehyde, and a method for producing an ethylenically unsaturated carboxylic ester |
CN108329294A (zh) * | 2018-04-10 | 2018-07-27 | 中国科学院成都有机化学有限公司 | 甲醛制备三聚甲醛的耦合方法 |
CN109771981B (zh) * | 2019-02-02 | 2021-05-18 | 南京工业大学 | 一种节能型精馏-膜法-精馏耦合分离共沸有机溶剂的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5061349A (en) * | 1988-12-20 | 1991-10-29 | Kueppenbender Herbert | Method of isolating trioxane from aqueous trioxane solutions by distillative separation |
EP0596381A1 (de) * | 1992-10-31 | 1994-05-11 | Hoechst Aktiengesellschaft | Verfahren zum Abtrennen von Trioxan aus einem wässrigen Gemisch |
JPH0733762A (ja) * | 1993-07-20 | 1995-02-03 | Asahi Chem Ind Co Ltd | トリオキサンの製造方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53111087A (en) * | 1977-02-17 | 1978-09-28 | Mitsubishi Gas Chem Co Inc | Storing of trioxane |
WO1988004569A1 (en) * | 1986-12-15 | 1988-06-30 | Mitsubishi Chemical Industries Limited | Process for separating liquid mixture |
JPH069645B2 (ja) * | 1986-12-25 | 1994-02-09 | リグナイト株式会社 | 混合溶液の分離方法 |
US5767294A (en) * | 1993-02-17 | 1998-06-16 | Hoechst Celanese Corporation | Process for the production of trioxane from formaldehyde |
-
1997
- 1997-07-26 DE DE19732291A patent/DE19732291A1/de not_active Withdrawn
-
1998
- 1998-07-02 US US09/462,627 patent/US6200429B1/en not_active Expired - Fee Related
- 1998-07-02 EP EP98939607A patent/EP1001954A1/de not_active Withdrawn
- 1998-07-02 CN CN98807365A patent/CN1264374A/zh active Pending
- 1998-07-02 KR KR1020007000817A patent/KR20010022244A/ko not_active Application Discontinuation
- 1998-07-02 WO PCT/EP1998/004094 patent/WO1999005137A1/de not_active Application Discontinuation
- 1998-07-02 JP JP2000504133A patent/JP2001510839A/ja not_active Withdrawn
- 1998-07-02 PL PL98338381A patent/PL338381A1/xx unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5061349A (en) * | 1988-12-20 | 1991-10-29 | Kueppenbender Herbert | Method of isolating trioxane from aqueous trioxane solutions by distillative separation |
EP0596381A1 (de) * | 1992-10-31 | 1994-05-11 | Hoechst Aktiengesellschaft | Verfahren zum Abtrennen von Trioxan aus einem wässrigen Gemisch |
JPH0733762A (ja) * | 1993-07-20 | 1995-02-03 | Asahi Chem Ind Co Ltd | トリオキサンの製造方法 |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Week 9515, Derwent World Patents Index; AN 95110626, XP002083063 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005063733A1 (de) * | 2003-12-23 | 2005-07-14 | Basf Aktiengesellschaft | Verfahren zur abtrennung von trioxan aus einem trioxan/formaldehyd/wasser-gemisch mittels druckwechsel-rektifikation |
US7713387B2 (en) | 2003-12-23 | 2010-05-11 | Basf Aktiengesellschaft | Method for separating trioxane from a trioxane/formaldehyde/water mixture by means of pressure change rectification |
WO2006018302A1 (de) * | 2004-08-19 | 2006-02-23 | Basf Aktiengesellschaft | Verfahren zur destillativen abtrennung von rein-trioxan |
WO2006040065A1 (de) * | 2004-10-08 | 2006-04-20 | Ticona Gmbh | Verfahren zur herstellung und entwässerung von zyklischen formalen |
WO2006040064A1 (de) * | 2004-10-08 | 2006-04-20 | Ticona Gmbh | Verfahren zur herstellung und entwässerung von zyklischen formalen |
Also Published As
Publication number | Publication date |
---|---|
CN1264374A (zh) | 2000-08-23 |
PL338381A1 (en) | 2000-10-23 |
JP2001510839A (ja) | 2001-08-07 |
KR20010022244A (ko) | 2001-03-15 |
US6200429B1 (en) | 2001-03-13 |
EP1001954A1 (de) | 2000-05-24 |
DE19732291A1 (de) | 1999-01-28 |
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