CA1178975A - Process for producing unsaturated ethers - Google Patents
Process for producing unsaturated ethersInfo
- Publication number
- CA1178975A CA1178975A CA000394036A CA394036A CA1178975A CA 1178975 A CA1178975 A CA 1178975A CA 000394036 A CA000394036 A CA 000394036A CA 394036 A CA394036 A CA 394036A CA 1178975 A CA1178975 A CA 1178975A
- Authority
- CA
- Canada
- Prior art keywords
- acetal
- formula
- catalyst
- process according
- cleavage
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 150000002170 ethers Chemical class 0.000 title abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 11
- 230000007017 scission Effects 0.000 claims abstract description 11
- 239000000292 calcium oxide Substances 0.000 claims abstract description 8
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims abstract description 8
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 .alpha.,.beta.-unsaturated alkenyl ethers Chemical class 0.000 claims abstract description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 7
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
- 238000001577 simple distillation Methods 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 abstract description 24
- 238000005798 acetal elimination reaction Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 235000013580 sausages Nutrition 0.000 description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004946 alkenylalkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 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
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH24481A CH644833A5 (de) | 1981-01-15 | 1981-01-15 | Verfahren zur herstellung von ungesaettigten aethern. |
| CH244/81-7 | 1981-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1178975A true CA1178975A (en) | 1984-12-04 |
Family
ID=4182580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000394036A Expired CA1178975A (en) | 1981-01-15 | 1982-01-13 | Process for producing unsaturated ethers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4396782A (https=) |
| JP (1) | JPS57139030A (https=) |
| CA (1) | CA1178975A (https=) |
| CH (1) | CH644833A5 (https=) |
| DE (1) | DE3200635A1 (https=) |
| FR (1) | FR2497793A1 (https=) |
| GB (1) | GB2091259B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4973751A (en) * | 1985-03-02 | 1990-11-27 | Basf Aktiengesellschaft | Preparation of unsaturated compounds by elimination reaction |
| DE3507378A1 (de) * | 1985-03-02 | 1986-09-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ungesaettigten verbindungen durch eliminierungsreaktion |
| DE3535128A1 (de) * | 1985-10-02 | 1987-04-02 | Degussa | Katalytische dealkoxylierung von geminalen di-alkoxyverbindungen, geeignete katalysatoren und deren herstellung |
| JPH0780801B2 (ja) * | 1987-04-03 | 1995-08-30 | 日曹丸善ケミカル株式会社 | ２−クロロエチルビニルエ−テルの精製方法 |
| DE3722891A1 (de) * | 1987-07-10 | 1989-01-19 | Basf Ag | Verfahren zur herstellung von vinylethern |
| DE3726126A1 (de) * | 1987-08-06 | 1989-02-16 | Basf Ag | Verfahren zur herstellung von 1.2-dialoxyethenen |
| DE3804162A1 (de) * | 1988-02-11 | 1989-08-24 | Basf Ag | Verfahren zur herstellung von vinylethern |
| DE4039950A1 (de) * | 1990-12-14 | 1992-06-17 | Hoechst Ag | Verfahren zur herstellung von ungesaettigten ethern |
| RU2144021C1 (ru) * | 1998-08-31 | 2000-01-10 | Волгоградское открытое акционерное общество "Химпром" | Способ получения винил-н-бутилового эфира |
| CN111348991B (zh) * | 2018-12-20 | 2022-08-05 | 万华化学集团股份有限公司 | 一种生产乙烯基醚方法 |
| CN118324613B (zh) * | 2024-06-13 | 2024-08-30 | 安徽华甬新材料股份有限公司 | 一种2-烷氧基丙烯的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218359A (en) * | 1965-11-16 | Preparation of alkoxyalkenes | ||
| GB681059A (en) | 1949-11-23 | 1952-10-15 | Celanese Corp | Unsaturated ethers |
| FR1282507A (fr) * | 1956-08-13 | 1962-01-27 | Air Reduction | Procédé de fabrication de l'éther trifluoroéthyl-vinylique |
| US3546300A (en) * | 1968-07-05 | 1970-12-08 | Gulf Research Development Co | Conversion of gem-dialkoxy compounds to unsaturated ethers using cacl2 |
| JPS541683B1 (https=) * | 1970-12-11 | 1979-01-27 | ||
| US4014941A (en) * | 1970-12-11 | 1977-03-29 | Kyowa Yuka Co., Ltd. | Method of producing α,β-unsaturated ether |
| JPS4945382A (https=) * | 1972-09-08 | 1974-04-30 |
-
1981
- 1981-01-15 CH CH24481A patent/CH644833A5/de not_active IP Right Cessation
-
1982
- 1982-01-07 US US06/337,898 patent/US4396782A/en not_active Expired - Fee Related
- 1982-01-11 GB GB8200655A patent/GB2091259B/en not_active Expired
- 1982-01-12 DE DE19823200635 patent/DE3200635A1/de not_active Withdrawn
- 1982-01-13 CA CA000394036A patent/CA1178975A/en not_active Expired
- 1982-01-14 JP JP57004769A patent/JPS57139030A/ja active Pending
- 1982-01-14 FR FR8200511A patent/FR2497793A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2497793B1 (https=) | 1984-02-24 |
| JPS57139030A (en) | 1982-08-27 |
| GB2091259A (en) | 1982-07-28 |
| US4396782A (en) | 1983-08-02 |
| GB2091259B (en) | 1984-09-26 |
| CH644833A5 (de) | 1984-08-31 |
| FR2497793A1 (fr) | 1982-07-16 |
| DE3200635A1 (de) | 1982-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1178975A (en) | Process for producing unsaturated ethers | |
| RU2132055C1 (ru) | Способ количественного анализа неочищенного фторметил-1,1,1,3,3,3-гексафторизопропилового эфира и способ получения фторметил-1,1,1,3,3,3-гексафторизопропилового эфира | |
| JP3252391B2 (ja) | α−フルオロエーテルからハイドロフルオロカーボンの製造 | |
| Brown et al. | Hydroboration. 51. Hydroboration of representative allenes with 9-borabicyclo [3.3. 1] nonane. An exceptional directive effect providing a direct synthesis of B-allyl-9-borabicyclo [3.3. 1] nonane derivatives | |
| JP3056310B2 (ja) | フツ素化エーテルの合成 | |
| EP0976705A1 (en) | Method of producing a phenolalkylether compound | |
| US12595219B2 (en) | Continuos flow synthesis of cannabidiol | |
| RU2039055C1 (ru) | Способ получения галоидированных 1,3-диоксоланов и галоидированные 1,3-диоксоланы | |
| KR910008368B1 (ko) | 불소화 알코올의 알콕실화 방법 | |
| US4288636A (en) | Preparation of citral | |
| TERAMOTO et al. | Selectivity of consecutive gas-liquid reactions | |
| JPH0853438A (ja) | トリオキサンを製造するための方法 | |
| Wong et al. | Reactivities and electronic aspects of nucleic acid heterocycles. II. Diazomethane methylation of uracil and its methyl derivatives | |
| EP0499157B1 (en) | Process for preparing 1,3-dioxoles | |
| US5196600A (en) | Synthesis of fluorinated dimethyl ethers | |
| Agarwala et al. | Kinetics of methylchlorosilane formation on Zn‐promoted Cu3Si | |
| JPWO1993016973A1 (ja) | １，１，１，２，２，４，４，５，５，５‐デカフルオロペンタンの製造方法及びその製造用中間体 | |
| EP0603002B1 (en) | Synthesis of difluoromethyl methyl ether | |
| EP0421322B1 (en) | Process for preparing penta-fluorodichloropropanes | |
| JP3489179B2 (ja) | ハイドロフルオロカーボンの製造方法 | |
| JP3325295B2 (ja) | イソフルランの製造方法 | |
| CA2268226A1 (en) | Process for preparing 3-methoxy-1-propanol | |
| US2544737A (en) | 11-oxabicyclo [4.4.1] undecanes and their preparation | |
| JPH0696560B2 (ja) | ２−プロピル−または２−ブチルピリミジンの製造法 | |
| Selve et al. | A novel procedure for the synthesis of ether-bridged perfluoro non-ionic surfactants |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |