JPS638100B2 - - Google Patents
Info
- Publication number
- JPS638100B2 JPS638100B2 JP61064300A JP6430086A JPS638100B2 JP S638100 B2 JPS638100 B2 JP S638100B2 JP 61064300 A JP61064300 A JP 61064300A JP 6430086 A JP6430086 A JP 6430086A JP S638100 B2 JPS638100 B2 JP S638100B2
- Authority
- JP
- Japan
- Prior art keywords
- atom
- acid
- reaction
- temperature
- chlorine
- 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 description 8
- -1 3-phenoxybenzyl ester Chemical class 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
- IVUPBSLRQYWNKZ-UHFFFAOYSA-N 4,6,6,6-tetrachloro-2-cyano-3,3-dimethylhexanoic acid Chemical compound N#CC(C(O)=O)C(C)(C)C(Cl)CC(Cl)(Cl)Cl IVUPBSLRQYWNKZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2589676A GB1580203A (en) | 1976-06-22 | 1976-06-22 | Preparation of cyclopropane derivatives |
| GB25896/1976 | 1976-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61233658A JPS61233658A (ja) | 1986-10-17 |
| JPS638100B2 true JPS638100B2 (enrdf_load_stackoverflow) | 1988-02-19 |
Family
ID=10235120
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7226277A Granted JPS52156839A (en) | 1976-06-22 | 1977-06-20 | Process for manufacture of cyclopropane derivatives |
| JP61064300A Granted JPS61233658A (ja) | 1976-06-22 | 1986-03-24 | 新規シクロプロパン誘導体 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7226277A Granted JPS52156839A (en) | 1976-06-22 | 1977-06-20 | Process for manufacture of cyclopropane derivatives |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK276879A (da) * | 1978-07-18 | 1980-01-19 | Ici Ltd | Fremgangsmaade til fremstilling af cyclopropannitriler |
| FR2485004A1 (fr) * | 1980-06-20 | 1981-12-24 | Roussel Uclaf | Derives cyclopropane-1-carboxyliques et leurs sels, leur preparation et leur application a la synthese d'intermediaires de composes pyrethrinoides de configuration cis |
| EP0064781B1 (en) * | 1981-04-30 | 1984-05-23 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of cyclopropane compounds |
| NL8203002A (nl) * | 1981-08-06 | 1983-03-01 | Shell Int Research | Stereospecifieke decarboxylering van dihalogeenvinylcyclopropaancarbonzuren. |
| GB2127012A (en) * | 1982-09-22 | 1984-04-04 | Shell Int Research | Process for the preparation of cyclopropane compounds |
-
1976
- 1976-06-22 GB GB2589676A patent/GB1580203A/en not_active Expired
-
1977
- 1977-05-03 CA CA277,560A patent/CA1123006A/en not_active Expired
- 1977-06-15 BE BE1008190A patent/BE855691A/xx not_active IP Right Cessation
- 1977-06-20 DK DK271877A patent/DK156955C/da not_active IP Right Cessation
- 1977-06-20 DE DE19772727613 patent/DE2727613A1/de active Granted
- 1977-06-20 JP JP7226277A patent/JPS52156839A/ja active Granted
- 1977-06-20 BR BR7703975A patent/BR7703975A/pt unknown
- 1977-06-20 FR FR7718843A patent/FR2355811A1/fr active Granted
- 1977-06-20 NL NL7706755A patent/NL7706755A/xx not_active Application Discontinuation
- 1977-06-20 CH CH752677A patent/CH629758A5/de not_active IP Right Cessation
- 1977-06-20 IT IT2486677A patent/IT1080226B/it active
-
1986
- 1986-03-24 JP JP61064300A patent/JPS61233658A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61233658A (ja) | 1986-10-17 |
| BE855691A (nl) | 1977-12-15 |
| JPS6140660B2 (enrdf_load_stackoverflow) | 1986-09-10 |
| CA1123006A (en) | 1982-05-04 |
| DK271877A (da) | 1977-12-23 |
| FR2355811A1 (fr) | 1978-01-20 |
| GB1580203A (en) | 1980-11-26 |
| DK156955C (da) | 1990-02-26 |
| DE2727613A1 (de) | 1977-12-29 |
| BR7703975A (pt) | 1978-04-25 |
| DK156955B (da) | 1989-10-23 |
| FR2355811B1 (enrdf_load_stackoverflow) | 1980-12-05 |
| IT1080226B (it) | 1985-05-16 |
| NL7706755A (nl) | 1977-12-27 |
| CH629758A5 (en) | 1982-05-14 |
| DE2727613C2 (enrdf_load_stackoverflow) | 1988-03-03 |
| JPS52156839A (en) | 1977-12-27 |
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