TW475925B - Production of high purity monoethylene glycol - Google Patents
Production of high purity monoethylene glycol Download PDFInfo
- Publication number
- TW475925B TW475925B TW088115552A TW88115552A TW475925B TW 475925 B TW475925 B TW 475925B TW 088115552 A TW088115552 A TW 088115552A TW 88115552 A TW88115552 A TW 88115552A TW 475925 B TW475925 B TW 475925B
- Authority
- TW
- Taiwan
- Prior art keywords
- patent application
- scope
- item
- tower
- monoethylene glycol
- Prior art date
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 124
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 52
- 238000004821 distillation Methods 0.000 claims abstract description 28
- 230000007062 hydrolysis Effects 0.000 claims abstract description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000018044 dehydration Effects 0.000 claims description 73
- 238000006297 dehydration reaction Methods 0.000 claims description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 238000000746 purification Methods 0.000 claims description 27
- 238000000926 separation method Methods 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 11
- 230000002079 cooperative effect Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 210000000416 exudates and transudate Anatomy 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 2
- 238000010626 work up procedure Methods 0.000 abstract 1
- 208000005156 Dehydration Diseases 0.000 description 58
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 22
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 18
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 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 3
- 238000010586 diagram Methods 0.000 description 3
- -1 ethyl Chemical class 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229910052704 radon Inorganic materials 0.000 description 2
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- Y10S203/00—Distillation: processes, separatory
- Y10S203/20—Power plant
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843697A DE19843697A1 (de) | 1998-09-23 | 1998-09-23 | Verfahren zur Herstellung von hochreinem Monoethylenglykol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW475925B true TW475925B (en) | 2002-02-11 |
Family
ID=7882020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088115552A TW475925B (en) | 1998-09-23 | 1999-09-09 | Production of high purity monoethylene glycol |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6605192B1 (enExample) |
| EP (1) | EP1115682B1 (enExample) |
| JP (1) | JP4427190B2 (enExample) |
| KR (1) | KR100611284B1 (enExample) |
| CN (1) | CN1217898C (enExample) |
| AR (1) | AR020655A1 (enExample) |
| AT (1) | ATE255084T1 (enExample) |
| AU (1) | AU5980199A (enExample) |
| BR (1) | BR9913889B1 (enExample) |
| CA (1) | CA2345053C (enExample) |
| DE (2) | DE19843697A1 (enExample) |
| ES (1) | ES2212671T3 (enExample) |
| MY (1) | MY121383A (enExample) |
| PL (1) | PL195588B1 (enExample) |
| RU (1) | RU2235710C2 (enExample) |
| SA (1) | SA99200783B1 (enExample) |
| TW (1) | TW475925B (enExample) |
| UA (1) | UA60383C2 (enExample) |
| WO (1) | WO2000017141A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6372925B1 (en) * | 2000-06-09 | 2002-04-16 | Shell Oil Company | Process for operating the epoxidation of ethylene |
| US7095741B1 (en) * | 2000-12-20 | 2006-08-22 | Cisco Technology, Inc. | Port isolation for restricting traffic flow on layer 2 switches |
| DE10321733A1 (de) * | 2003-05-14 | 2004-12-02 | Basf Ag | Verfahren zur Herstellung von ameisensauren Formiaten |
| DE602006012549D1 (de) * | 2005-12-29 | 2010-04-08 | Basf Se | Verfahren zur trennung von propylenglykol von wässrigen zusammensetzungen |
| RU2312696C1 (ru) * | 2006-03-17 | 2007-12-20 | Андрей Григорьевич Вендило | Универсальная установка для очистки высококипящих растворителей вакуумной ректификацией и способы очистки вакуумной ректификацией на ней этиленгликоля, моноэтаноламина, метилцеллозольва, этилцеллозольва, бутилцеллозольва, n-метилпирролидона и бензилового спирта |
| EP2035359B1 (en) * | 2006-06-13 | 2010-02-24 | Shell Internationale Research Maatschappij B.V. | Glycol separation and purification |
| RU2511442C2 (ru) * | 2008-10-09 | 2014-04-10 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ регенерации моноэтиленгликоля |
| WO2010053900A2 (en) * | 2008-11-10 | 2010-05-14 | Dow Technology Investments, Llc | Process for producing low color glycols |
| PL217778B1 (pl) | 2011-06-20 | 2014-08-29 | Piotr Medoń | Sposób osuszania glikolu i układ do osuszania glikolu |
| CN103265401B (zh) * | 2013-04-24 | 2014-12-17 | 河南朝歌日光新能源股份有限公司 | 一种煤制乙二醇工艺副产残液的回收方法 |
| US9732019B1 (en) * | 2016-04-01 | 2017-08-15 | Cameron Solutions, Inc. | System and method to remove organic acid from a rich MEG stream by stripping |
| GB201710508D0 (en) * | 2017-06-30 | 2017-08-16 | Johnson Matthey Davy Technologies Ltd | Process |
| WO2019101707A1 (en) * | 2017-11-23 | 2019-05-31 | Shell Internationale Research Maatschappij B.V. | Processes for the production of ethylene oxide and ethylene glycol |
| NL2025637B1 (en) * | 2020-05-20 | 2021-12-07 | Ioniqa Tech B V | A separation method and reactor system for a glycol-water mixture |
| CN119868990B (zh) * | 2025-03-12 | 2025-10-24 | 连云港石化有限公司 | 一种乙二醇预脱水塔装置及其使用方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2510548A (en) * | 1947-06-20 | 1950-06-06 | Lummus Co | Multiple-effect distillation |
| DE1942094A1 (de) | 1968-08-22 | 1970-02-26 | Union Carbide Corp | Verfahren zur Reinigung von verunreinigten Glykolen |
| IT972794B (it) | 1972-12-22 | 1974-05-31 | Sir Soc Italiana Resine Spa | Procedimento perfezionato per la produzione del glicole etilenico |
| US4182659A (en) * | 1977-10-31 | 1980-01-08 | Davy International Aktiengesellschaft | Method of concentrating a water-containing glycol |
| DE3001727A1 (de) | 1980-01-18 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von hochreinem monoethylenglykol |
| DE3338488A1 (de) | 1982-10-29 | 1984-05-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von temperaturempfindlichen produkten durch thermisch schonende destillation mittels eines mit einer destillationskolonne verbundenen duennschichtverdampfers und eine anordnung zur durchfuehrung des verfahrens |
| JPS6089439A (ja) | 1983-10-24 | 1985-05-20 | Mitsui Toatsu Chem Inc | エチレングリコ−ルの製造方法 |
| FR2564458B1 (fr) | 1984-05-15 | 1986-09-12 | Atochem | Procede de separation de l'ethyleneglycol sous forme concentree dans un procede de fabrication d'oxyde d'ethylene |
| DE4306144A1 (de) * | 1993-02-27 | 1994-09-01 | Brown John Deutsche Eng Gmbh | Verfahren und Polykondensationsanlage zur Aufbereitung von verunreinigtem Ethylenglykol |
| DE19602116A1 (de) | 1996-01-22 | 1997-07-24 | Basf Ag | Verfahren zur Gewinnung von Glykolen mit niedrigem Aldehydgehalt |
| RU2111949C1 (ru) * | 1996-08-19 | 1998-05-27 | Акционерное общество "Нижнекамскнефтехим" | Способ извлечения моно- и диэтиленгликолей из кубового остатка процесса выделения моноэтиленгликоля |
| US5738417A (en) * | 1997-01-29 | 1998-04-14 | Westinghouse Air Brake Company | Brake pipe sensing unit |
-
1998
- 1998-09-23 DE DE19843697A patent/DE19843697A1/de not_active Withdrawn
-
1999
- 1999-09-09 TW TW088115552A patent/TW475925B/zh not_active IP Right Cessation
- 1999-09-20 MY MYPI99004083A patent/MY121383A/en unknown
- 1999-09-21 KR KR1020017003647A patent/KR100611284B1/ko not_active Expired - Lifetime
- 1999-09-21 EP EP99969405A patent/EP1115682B1/de not_active Expired - Lifetime
- 1999-09-21 AT AT99969405T patent/ATE255084T1/de not_active IP Right Cessation
- 1999-09-21 AU AU59801/99A patent/AU5980199A/en not_active Abandoned
- 1999-09-21 PL PL99347580A patent/PL195588B1/pl unknown
- 1999-09-21 CN CN998112844A patent/CN1217898C/zh not_active Expired - Lifetime
- 1999-09-21 UA UA2001042717A patent/UA60383C2/uk unknown
- 1999-09-21 CA CA002345053A patent/CA2345053C/en not_active Expired - Lifetime
- 1999-09-21 ES ES99969405T patent/ES2212671T3/es not_active Expired - Lifetime
- 1999-09-21 DE DE59907884T patent/DE59907884D1/de not_active Expired - Lifetime
- 1999-09-21 WO PCT/EP1999/006968 patent/WO2000017141A1/de not_active Ceased
- 1999-09-21 US US09/787,616 patent/US6605192B1/en not_active Expired - Lifetime
- 1999-09-21 BR BRPI9913889-1A patent/BR9913889B1/pt not_active IP Right Cessation
- 1999-09-21 JP JP2000574053A patent/JP4427190B2/ja not_active Expired - Lifetime
- 1999-09-21 RU RU2001111009/04A patent/RU2235710C2/ru active
- 1999-09-22 AR ARP990104764A patent/AR020655A1/es active IP Right Grant
- 1999-11-30 SA SA99200783A patent/SA99200783B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE19843697A1 (de) | 2000-03-30 |
| BR9913889B1 (pt) | 2011-01-11 |
| EP1115682B1 (de) | 2003-11-26 |
| AR020655A1 (es) | 2002-05-22 |
| JP2002526463A (ja) | 2002-08-20 |
| WO2000017141A1 (de) | 2000-03-30 |
| KR100611284B1 (ko) | 2006-08-10 |
| CA2345053C (en) | 2008-07-15 |
| AU5980199A (en) | 2000-04-10 |
| MY121383A (en) | 2006-01-28 |
| RU2235710C2 (ru) | 2004-09-10 |
| CN1217898C (zh) | 2005-09-07 |
| CN1319080A (zh) | 2001-10-24 |
| CA2345053A1 (en) | 2000-03-30 |
| EP1115682A1 (de) | 2001-07-18 |
| UA60383C2 (uk) | 2003-10-15 |
| ES2212671T3 (es) | 2004-07-16 |
| ATE255084T1 (de) | 2003-12-15 |
| DE59907884D1 (de) | 2004-01-08 |
| PL195588B1 (pl) | 2007-10-31 |
| PL347580A1 (en) | 2002-04-08 |
| SA99200783B1 (ar) | 2006-08-12 |
| BR9913889A (pt) | 2001-07-03 |
| JP4427190B2 (ja) | 2010-03-03 |
| US6605192B1 (en) | 2003-08-12 |
| KR20010075276A (ko) | 2001-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GD4A | Issue of patent certificate for granted invention patent | ||
| MK4A | Expiration of patent term of an invention patent |