DE3933247C1 - - Google Patents
Info
- Publication number
- DE3933247C1 DE3933247C1 DE3933247A DE3933247A DE3933247C1 DE 3933247 C1 DE3933247 C1 DE 3933247C1 DE 3933247 A DE3933247 A DE 3933247A DE 3933247 A DE3933247 A DE 3933247A DE 3933247 C1 DE3933247 C1 DE 3933247C1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- alkyl
- formula
- acid
- 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.)
- Expired - Fee Related
Links
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- JEPJBZHWRGLINP-UHFFFAOYSA-N 2,2-dimethoxy-3-methylbutane Chemical compound COC(C)(OC)C(C)C JEPJBZHWRGLINP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000002084 enol ethers Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 Tribromomethyl Chemical group 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-N 2,2-diethylpropanedioic acid Chemical compound CCC(CC)(C(O)=O)C(O)=O LTMRRSWNXVJMBA-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- IMFKDZCVWYKAAL-UHFFFAOYSA-N phosphoric acid pyridine Chemical compound P(=O)(O)(O)O.N1=CC=CC=C1.N1=CC=CC=C1 IMFKDZCVWYKAAL-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3933247A DE3933247C1 (enrdf_load_stackoverflow) | 1989-10-05 | 1989-10-05 | |
| EP90914531A EP0494906A1 (de) | 1989-10-05 | 1990-10-01 | KONTINUIERLICHES VERFAHREN ZUR HERSTELLUNG VON $g(D)1-ENOLETHERN |
| AU64429/90A AU6442990A (en) | 1989-10-05 | 1990-10-01 | Method for continuous production of delta1-enol ethers |
| PCT/EP1990/001646 WO1991004956A1 (de) | 1989-10-05 | 1990-10-01 | Kontinuierliches verfahren zur herstellung von δ1-enolethern |
| KR1019920700773A KR950006801B1 (ko) | 1989-10-05 | 1990-10-01 | △1-엔올 에테르의 연속적인 제조방법 |
| JP2513602A JPH05500667A (ja) | 1989-10-05 | 1990-10-01 | △１―エノールエーテルの連続的製造方法 |
| IL95896A IL95896A0 (en) | 1989-10-05 | 1990-10-03 | Continuous process for the preparation of delta 1 enol ethers |
| ZA907922A ZA907922B (en) | 1989-10-05 | 1990-10-04 | Continuous process for the preparation of delta 1 enol ethers |
| HU9201136A HUT61259A (en) | 1989-10-05 | 1992-04-03 | Process for producing delta-1 enol ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3933247A DE3933247C1 (enrdf_load_stackoverflow) | 1989-10-05 | 1989-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3933247C1 true DE3933247C1 (enrdf_load_stackoverflow) | 1991-01-17 |
Family
ID=6390869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3933247A Expired - Fee Related DE3933247C1 (enrdf_load_stackoverflow) | 1989-10-05 | 1989-10-05 |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0703211A1 (de) * | 1994-09-23 | 1996-03-27 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von ungesättigten Ethern |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116444352B (zh) * | 2022-01-06 | 2024-06-25 | 万华化学集团股份有限公司 | 一种2-甲氧基丙烯液相合成的新方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE596888A (fr) * | 1959-11-19 | 1961-05-09 | Hoffmann La Roche | Procédé pour la préparation d'éthers énoliques |
| DE3804162A1 (de) * | 1988-02-11 | 1989-08-24 | Basf Ag | Verfahren zur herstellung von vinylethern |
-
1989
- 1989-10-05 DE DE3933247A patent/DE3933247C1/de not_active Expired - Fee Related
-
1990
- 1990-10-01 JP JP2513602A patent/JPH05500667A/ja active Pending
- 1990-10-01 AU AU64429/90A patent/AU6442990A/en not_active Abandoned
- 1990-10-01 KR KR1019920700773A patent/KR950006801B1/ko not_active Expired - Lifetime
- 1990-10-01 WO PCT/EP1990/001646 patent/WO1991004956A1/de not_active Application Discontinuation
- 1990-10-01 EP EP90914531A patent/EP0494906A1/de not_active Withdrawn
- 1990-10-03 IL IL95896A patent/IL95896A0/xx unknown
- 1990-10-04 ZA ZA907922A patent/ZA907922B/xx unknown
-
1992
- 1992-04-03 HU HU9201136A patent/HUT61259A/hu unknown
Non-Patent Citations (2)
| Title |
|---|
| Chem. Ber. 116, S. 220-9, 1983 * |
| HOUBEN-WEYL: Methoden der organischen Chemie, Bd. 6/3, S. 97 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0703211A1 (de) * | 1994-09-23 | 1996-03-27 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von ungesättigten Ethern |
Also Published As
| Publication number | Publication date |
|---|---|
| KR927003496A (ko) | 1992-12-18 |
| HU9201136D0 (en) | 1992-07-28 |
| WO1991004956A1 (de) | 1991-04-18 |
| AU6442990A (en) | 1991-04-28 |
| JPH05500667A (ja) | 1993-02-12 |
| ZA907922B (en) | 1991-07-31 |
| EP0494906A1 (de) | 1992-07-22 |
| IL95896A0 (en) | 1991-07-18 |
| KR950006801B1 (ko) | 1995-06-22 |
| HUT61259A (en) | 1992-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |