DE3200635A1 - "verfahren zur herstellung von ungesaettigten aethern" - Google Patents
"verfahren zur herstellung von ungesaettigten aethern"Info
- Publication number
- DE3200635A1 DE3200635A1 DE19823200635 DE3200635A DE3200635A1 DE 3200635 A1 DE3200635 A1 DE 3200635A1 DE 19823200635 DE19823200635 DE 19823200635 DE 3200635 A DE3200635 A DE 3200635A DE 3200635 A1 DE3200635 A1 DE 3200635A1
- Authority
- DE
- Germany
- Prior art keywords
- acetals
- formula
- catalyst
- cleavage
- acetal
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 21
- 150000002170 ethers Chemical class 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001241 acetals Chemical class 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 22
- 239000000292 calcium oxide Substances 0.000 claims description 10
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 10
- 238000003776 cleavage reaction Methods 0.000 claims description 10
- 230000007017 scission Effects 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 8
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 β-unsaturated alkenyl ethers Chemical class 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000001577 simple distillation Methods 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 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
- 150000001298 alcohols Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 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
- KJESGYZFVCIMDE-UHFFFAOYSA-N 1-chloroethanol Chemical compound CC(O)Cl KJESGYZFVCIMDE-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
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000005798 acetal elimination reaction Methods 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
- 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
- 239000012876 carrier material Substances 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 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
- 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- 239000000463 material Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002894 organic compounds 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
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH24481A CH644833A5 (de) | 1981-01-15 | 1981-01-15 | Verfahren zur herstellung von ungesaettigten aethern. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3200635A1 true DE3200635A1 (de) | 1982-08-12 |
Family
ID=4182580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823200635 Withdrawn DE3200635A1 (de) | 1981-01-15 | 1982-01-12 | "verfahren zur herstellung von ungesaettigten aethern" |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4396782A (2) |
| JP (1) | JPS57139030A (2) |
| CA (1) | CA1178975A (2) |
| CH (1) | CH644833A5 (2) |
| DE (1) | DE3200635A1 (2) |
| FR (1) | FR2497793A1 (2) |
| GB (1) | GB2091259B (2) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3811095A1 (de) * | 1987-04-03 | 1988-10-13 | Nisso Maruzen Chemical Co | Verfahren zur isolierung von 2-chlorethylvinylether |
Families Citing this family (10)
| 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 |
| 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 (2) * | 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 (2) * | 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3811095A1 (de) * | 1987-04-03 | 1988-10-13 | Nisso Maruzen Chemical Co | Verfahren zur isolierung von 2-chlorethylvinylether |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2497793B1 (2) | 1984-02-24 |
| JPS57139030A (en) | 1982-08-27 |
| CA1178975A (en) | 1984-12-04 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |