DE2364150A1 - Verfahren zur herstellung von aethylenglykolaethern - Google Patents
Verfahren zur herstellung von aethylenglykolaethernInfo
- Publication number
- DE2364150A1 DE2364150A1 DE2364150A DE2364150A DE2364150A1 DE 2364150 A1 DE2364150 A1 DE 2364150A1 DE 2364150 A DE2364150 A DE 2364150A DE 2364150 A DE2364150 A DE 2364150A DE 2364150 A1 DE2364150 A1 DE 2364150A1
- Authority
- DE
- Germany
- Prior art keywords
- stage
- ethylene oxide
- glycol ether
- alcohol
- reaction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title 1
- 239000005977 Ethylene Substances 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 36
- -1 glycol ethers Chemical class 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- PRBXPAHXMGDVNQ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]acetic acid Chemical compound OCCOCCOCC(O)=O PRBXPAHXMGDVNQ-UHFFFAOYSA-N 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 1
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT33441/72A IT972792B (it) | 1972-12-22 | 1972-12-22 | Procedimento per la preparazione di glicoli eteri |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2364150A1 true DE2364150A1 (de) | 1974-07-25 |
Family
ID=11237442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2364150A Pending DE2364150A1 (de) | 1972-12-22 | 1973-12-21 | Verfahren zur herstellung von aethylenglykolaethern |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3935279A (enExample) |
| JP (1) | JPS5530496B2 (enExample) |
| CA (1) | CA1011345A (enExample) |
| CH (1) | CH603519A5 (enExample) |
| DE (1) | DE2364150A1 (enExample) |
| FR (1) | FR2211438B1 (enExample) |
| GB (1) | GB1418510A (enExample) |
| IT (1) | IT972792B (enExample) |
| NL (1) | NL7317387A (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1064527A (en) * | 1975-07-21 | 1979-10-16 | John L. Riddle | Preparation of secondary alkanol alkoxylates |
| DE3125107A1 (de) * | 1981-06-26 | 1983-01-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung lagerstabiler (poly-)alkylenglycolmonoalkylether |
| RU2159224C2 (ru) * | 1999-02-02 | 2000-11-20 | Открытое акционерное общество "Органический синтез" | Способ выделения бутиловых эфиров моно- и диэтиленгликоля из продуктов оксиэтилирования бутилового спирта |
| US6372925B1 (en) | 2000-06-09 | 2002-04-16 | Shell Oil Company | Process for operating the epoxidation of ethylene |
| BRPI0819403B1 (pt) * | 2007-12-12 | 2019-06-18 | Dow Global Technologies Inc. | Processo contínuo não aquoso para produzir glicol éter fenólico |
| KR20230027318A (ko) | 2016-08-09 | 2023-02-27 | 사이언티픽 디자인 컴파니 인코포레이티드 | 글리콜 에테르 제조 방법 |
| US12018220B2 (en) | 2019-05-24 | 2024-06-25 | Eastman Chemical Company | Thermal pyoil to a gas fed cracker furnace |
| EP3976735A4 (en) | 2019-05-24 | 2023-03-15 | Eastman Chemical Company | CO-CRACKING OF PYROLYTIC OIL WITH ETHANE |
| US11365357B2 (en) | 2019-05-24 | 2022-06-21 | Eastman Chemical Company | Cracking C8+ fraction of pyoil |
| US11319262B2 (en) | 2019-10-31 | 2022-05-03 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US12173237B2 (en) | 2019-10-31 | 2024-12-24 | Eastman Chemical Company | Processes and systems for formation of recycle-content hydrocarbon compositions |
| US12528995B2 (en) | 2019-10-31 | 2026-01-20 | ExxonMobil Product Solutions Company | Pyrolysis method and system for recycled waste |
| US11945998B2 (en) | 2019-10-31 | 2024-04-02 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| EP4051763A4 (en) | 2019-10-31 | 2024-03-20 | Eastman Chemical Company | METHOD AND SYSTEMS FOR PRODUCING HYDROCARBON COMPOSITIONS WITH RECYCLE CONTENT |
| WO2021092293A1 (en) | 2019-11-07 | 2021-05-14 | Eastman Chemical Company | Recycle content oxo glycols |
| WO2021211517A1 (en) | 2020-04-13 | 2021-10-21 | Eastman Chemical Company | Liquefying and dehalogenating waste plastics |
| RU2758851C1 (ru) * | 2020-07-08 | 2021-11-02 | Публичное акционерное общество "Омский каучук" | Способ получения бутилцеллозольва из окиси этилена и бутанола |
| WO2026062130A1 (en) | 2024-09-19 | 2026-03-26 | Basf Se | Energy-efficient process for preparing one or more ethers |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1696874A (en) * | 1928-12-25 | Process of making ethylene glycol monoalkyl ethers | ||
| US2276597A (en) * | 1942-03-17 | Manufacture of glycol ethers | ||
| US2870220A (en) * | 1953-08-11 | 1959-01-20 | Union Carbide Corp | Production of nonionic surface active agents |
| LU47604A1 (enExample) * | 1964-12-17 | 1966-06-17 |
-
1972
- 1972-12-22 IT IT33441/72A patent/IT972792B/it active
-
1973
- 1973-12-17 CH CH1763473A patent/CH603519A5/xx not_active IP Right Cessation
- 1973-12-18 GB GB5865473A patent/GB1418510A/en not_active Expired
- 1973-12-19 NL NL7317387A patent/NL7317387A/xx unknown
- 1973-12-19 CA CA188,503A patent/CA1011345A/en not_active Expired
- 1973-12-21 JP JP744698A patent/JPS5530496B2/ja not_active Expired
- 1973-12-21 FR FR7345938A patent/FR2211438B1/fr not_active Expired
- 1973-12-21 DE DE2364150A patent/DE2364150A1/de active Pending
- 1973-12-26 US US05/428,575 patent/US3935279A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT972792B (it) | 1974-05-31 |
| JPS5530496B2 (enExample) | 1980-08-11 |
| GB1418510A (en) | 1975-12-24 |
| NL7317387A (enExample) | 1974-06-25 |
| FR2211438B1 (enExample) | 1977-08-12 |
| US3935279A (en) | 1976-01-27 |
| CA1011345A (en) | 1977-05-31 |
| CH603519A5 (enExample) | 1978-08-15 |
| JPS5046612A (enExample) | 1975-04-25 |
| FR2211438A1 (enExample) | 1974-07-19 |
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