DE2727612C2 - Verfahren zur Herstellung von 2-(2,2-Dihalogenvinyl)-3,3-dimethylcyclopropancarbonitrilen - Google Patents
Verfahren zur Herstellung von 2-(2,2-Dihalogenvinyl)-3,3-dimethylcyclopropancarbonitrilenInfo
- Publication number
- DE2727612C2 DE2727612C2 DE19772727612 DE2727612A DE2727612C2 DE 2727612 C2 DE2727612 C2 DE 2727612C2 DE 19772727612 DE19772727612 DE 19772727612 DE 2727612 A DE2727612 A DE 2727612A DE 2727612 C2 DE2727612 C2 DE 2727612C2
- Authority
- DE
- Germany
- Prior art keywords
- cyano
- dihalovinyl
- preparation
- formula
- dimethylcyclopropanecarbonitriles
- 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 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 229910021529 ammonia Inorganic materials 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- -1 2,2-dichlorovinyl Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- XOLBXXZZQLVKRU-UHFFFAOYSA-N C1CC1.[C] Chemical compound C1CC1.[C] XOLBXXZZQLVKRU-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- AFRPUUYIQUBHLH-UHFFFAOYSA-N azane;cyclopropanecarboxylic acid Chemical compound [NH4+].[O-]C(=O)C1CC1 AFRPUUYIQUBHLH-UHFFFAOYSA-N 0.000 description 1
- XOHJEHZDPJGUCU-UHFFFAOYSA-N azanium;1-cyano-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound [NH4+].CC1(C)C(C=C(Cl)Cl)C1(C#N)C([O-])=O XOHJEHZDPJGUCU-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| GB2589576A GB1580202A (en) | 1976-06-22 | 1976-06-22 | Process for the preparation of cyclopropanecarbonitriles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2727612A1 DE2727612A1 (de) | 1978-01-05 |
| DE2727612C2 true DE2727612C2 (de) | 1986-03-06 |
Family
ID=10235106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772727612 Expired DE2727612C2 (de) | 1976-06-22 | 1977-06-20 | Verfahren zur Herstellung von 2-(2,2-Dihalogenvinyl)-3,3-dimethylcyclopropancarbonitrilen |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS52156838A (cs) |
| BE (1) | BE855693A (cs) |
| BR (1) | BR7703996A (cs) |
| CA (1) | CA1085873A (cs) |
| CH (1) | CH628326A5 (cs) |
| DE (1) | DE2727612C2 (cs) |
| DK (1) | DK155829C (cs) |
| FR (1) | FR2355810A1 (cs) |
| GB (1) | GB1580202A (cs) |
| IT (1) | IT1080224B (cs) |
| NL (1) | NL188639C (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2606635A1 (de) * | 1976-02-19 | 1977-08-25 | Bayer Ag | Verfahren zur herstellung von 2,2-dimethyl-3-(2',2'-dichlorvinyl) -cyclopropan-1-carbonsaeure |
-
1976
- 1976-06-22 GB GB2589576A patent/GB1580202A/en not_active Expired
-
1977
- 1977-06-03 CA CA279,843A patent/CA1085873A/en not_active Expired
- 1977-06-15 BE BE1008192A patent/BE855693A/xx not_active IP Right Cessation
- 1977-06-20 FR FR7718842A patent/FR2355810A1/fr active Granted
- 1977-06-20 DK DK271777A patent/DK155829C/da not_active IP Right Cessation
- 1977-06-20 IT IT2486777A patent/IT1080224B/it active
- 1977-06-20 JP JP7226077A patent/JPS52156838A/ja active Pending
- 1977-06-20 DE DE19772727612 patent/DE2727612C2/de not_active Expired
- 1977-06-20 NL NL7706754A patent/NL188639C/xx not_active IP Right Cessation
- 1977-06-20 BR BR7703996A patent/BR7703996A/pt unknown
- 1977-06-20 CH CH752577A patent/CH628326A5/de not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1085873A (en) | 1980-09-16 |
| NL188639B (nl) | 1992-03-16 |
| DK155829C (da) | 1989-10-02 |
| BR7703996A (pt) | 1978-04-25 |
| GB1580202A (en) | 1980-11-26 |
| IT1080224B (it) | 1985-05-16 |
| DK271777A (da) | 1977-12-23 |
| FR2355810B1 (cs) | 1978-10-20 |
| NL188639C (nl) | 1992-08-17 |
| BE855693A (nl) | 1977-12-15 |
| FR2355810A1 (fr) | 1978-01-20 |
| CH628326A5 (en) | 1982-02-26 |
| JPS52156838A (en) | 1977-12-27 |
| DK155829B (da) | 1989-05-22 |
| NL7706754A (nl) | 1977-12-27 |
| DE2727612A1 (de) | 1978-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |