KR950006801B1 - △1-엔올 에테르의 연속적인 제조방법 - Google Patents
△1-엔올 에테르의 연속적인 제조방법 Download PDFInfo
- Publication number
- KR950006801B1 KR950006801B1 KR1019920700773A KR920700773A KR950006801B1 KR 950006801 B1 KR950006801 B1 KR 950006801B1 KR 1019920700773 A KR1019920700773 A KR 1019920700773A KR 920700773 A KR920700773 A KR 920700773A KR 950006801 B1 KR950006801 B1 KR 950006801B1
- Authority
- KR
- South Korea
- Prior art keywords
- enol ether
- alkyl
- acid
- reaction
- general formula
- 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
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- -1 R 3 is H Chemical group 0.000 claims description 4
- GVOUFPWUYJWQSK-UHFFFAOYSA-N Cyclofenil Chemical group C1=CC(OC(=O)C)=CC=C1C(C=1C=CC(OC(C)=O)=CC=1)=C1CCCCC1 GVOUFPWUYJWQSK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229960002944 cyclofenil Drugs 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002084 enol ethers Chemical class 0.000 description 26
- 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
- 238000000926 separation method Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KDMASJAWKNAFBX-UHFFFAOYSA-N 2-methoxy-3-methylbut-1-ene Chemical compound COC(=C)C(C)C KDMASJAWKNAFBX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class 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
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000011005 laboratory method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3933247A DE3933247C1 (enrdf_load_stackoverflow) | 1989-10-05 | 1989-10-05 | |
| DEP3933247.0 | 1989-10-05 | ||
| PCT/EP1990/001646 WO1991004956A1 (de) | 1989-10-05 | 1990-10-01 | Kontinuierliches verfahren zur herstellung von δ1-enolethern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR927003496A KR927003496A (ko) | 1992-12-18 |
| KR950006801B1 true KR950006801B1 (ko) | 1995-06-22 |
Family
ID=6390869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920700773A Expired - Lifetime KR950006801B1 (ko) | 1989-10-05 | 1990-10-01 | △1-엔올 에테르의 연속적인 제조방법 |
Country Status (9)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4433949A1 (de) * | 1994-09-23 | 1996-03-28 | Huels Chemische Werke Ag | Verfahren zur Herstellung von ungesättigten Ethern |
| 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 EP EP90914531A patent/EP0494906A1/de not_active Withdrawn
- 1990-10-01 WO PCT/EP1990/001646 patent/WO1991004956A1/de not_active Application Discontinuation
- 1990-10-01 KR KR1019920700773A patent/KR950006801B1/ko not_active Expired - Lifetime
- 1990-10-01 AU AU64429/90A patent/AU6442990A/en not_active Abandoned
- 1990-10-01 JP JP2513602A patent/JPH05500667A/ja active Pending
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| DE3933247C1 (enrdf_load_stackoverflow) | 1991-01-17 |
| JPH05500667A (ja) | 1993-02-12 |
| ZA907922B (en) | 1991-07-31 |
| KR927003496A (ko) | 1992-12-18 |
| IL95896A0 (en) | 1991-07-18 |
| HU9201136D0 (en) | 1992-07-28 |
| EP0494906A1 (de) | 1992-07-22 |
| WO1991004956A1 (de) | 1991-04-18 |
| HUT61259A (en) | 1992-12-28 |
| AU6442990A (en) | 1991-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19920404 |
|
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19920404 Comment text: Request for Examination of Application |
|
| PG1501 | Laying open of application | ||
| G160 | Decision to publish patent application | ||
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19950526 |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19950928 |
|
| NORF | Unpaid initial registration fee | ||
| PC1904 | Unpaid initial registration fee |