CA2345053C - Method for producing highly pure monoethylene glycol - Google Patents
Method for producing highly pure monoethylene glycol Download PDFInfo
- Publication number
- CA2345053C CA2345053C CA002345053A CA2345053A CA2345053C CA 2345053 C CA2345053 C CA 2345053C CA 002345053 A CA002345053 A CA 002345053A CA 2345053 A CA2345053 A CA 2345053A CA 2345053 C CA2345053 C CA 2345053C
- Authority
- CA
- Canada
- Prior art keywords
- column
- monoethylene glycol
- stream
- pressure
- dewatering
- 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.)
- Expired - Lifetime
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 107
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 54
- 238000004821 distillation Methods 0.000 claims abstract description 33
- 230000007062 hydrolysis Effects 0.000 claims abstract description 18
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims description 53
- 238000011084 recovery Methods 0.000 claims description 6
- 238000010626 work up procedure Methods 0.000 claims description 4
- 230000006872 improvement Effects 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 abstract 3
- 238000006297 dehydration reaction Methods 0.000 abstract 3
- 238000012958 reprocessing Methods 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 57
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 35
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- 150000002334 glycols Chemical class 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- -1 bisulfite ions Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- PHOLIFLKGONSGY-CSKARUKUSA-N (e)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazine Chemical compound C1=CC=C2S\C(=N\N)N(C)C2=C1 PHOLIFLKGONSGY-CSKARUKUSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000018734 Sambucus australis Nutrition 0.000 description 1
- 244000180577 Sambucus australis Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843697A DE19843697A1 (de) | 1998-09-23 | 1998-09-23 | Verfahren zur Herstellung von hochreinem Monoethylenglykol |
| DE19843697.1 | 1998-09-23 | ||
| PCT/EP1999/006968 WO2000017141A1 (de) | 1998-09-23 | 1999-09-21 | Verfahren zur herstellung von hochreinem monoethylenglykol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2345053A1 CA2345053A1 (en) | 2000-03-30 |
| CA2345053C true CA2345053C (en) | 2008-07-15 |
Family
ID=7882020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002345053A Expired - Lifetime CA2345053C (en) | 1998-09-23 | 1999-09-21 | Method for producing highly pure 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 |
| TW475925B (en) | 2002-02-11 |
| 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 |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20190923 |