JPH038343B2 - - Google Patents
Info
- Publication number
- JPH038343B2 JPH038343B2 JP10043482A JP10043482A JPH038343B2 JP H038343 B2 JPH038343 B2 JP H038343B2 JP 10043482 A JP10043482 A JP 10043482A JP 10043482 A JP10043482 A JP 10043482A JP H038343 B2 JPH038343 B2 JP H038343B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- compound
- carried out
- dichloroethane
- hydroxypyrazole
- 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
- -1 aluminum halide Chemical class 0.000 claims description 29
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 20
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 14
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 12
- 238000006482 condensation reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 description 3
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- UZYYBZNZSSNYSA-UHFFFAOYSA-N 1,2,4-trichloro-3-methylbenzene Chemical compound CC1=C(Cl)C=CC(Cl)=C1Cl UZYYBZNZSSNYSA-UHFFFAOYSA-N 0.000 description 2
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 description 2
- NDELSWXIAJLWOU-UHFFFAOYSA-N 2,5-dimethyl-4h-pyrazol-3-one Chemical compound CN1N=C(C)CC1=O NDELSWXIAJLWOU-UHFFFAOYSA-N 0.000 description 2
- UWKAOSCWPJJPFU-UHFFFAOYSA-N CC1=NN(C)C(O)=C1C(=O)C1=CC=C(Cl)C(C)=C1Cl Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(Cl)C(C)=C1Cl UWKAOSCWPJJPFU-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
- RCTKUIOMKBEGTG-UHFFFAOYSA-N 1,3,5-trichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=C(Cl)C=C1Cl RCTKUIOMKBEGTG-UHFFFAOYSA-N 0.000 description 1
- KWLWVGAAGRYCAG-UHFFFAOYSA-N 1,3-dichloro-2,4-dimethylbenzene Chemical group CC1=CC=C(Cl)C(C)=C1Cl KWLWVGAAGRYCAG-UHFFFAOYSA-N 0.000 description 1
- NUDVJQOVBFONPG-UHFFFAOYSA-N 1,3-dichloro-2-ethylbenzene Chemical compound CCC1=C(Cl)C=CC=C1Cl NUDVJQOVBFONPG-UHFFFAOYSA-N 0.000 description 1
- KFAKZJUYBOYVKA-UHFFFAOYSA-N 1,4-dichloro-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1Cl KFAKZJUYBOYVKA-UHFFFAOYSA-N 0.000 description 1
- MJTYPPBFTMKLGA-UHFFFAOYSA-N 2,4-dichloro-1-ethylbenzene Chemical compound CCC1=CC=C(Cl)C=C1Cl MJTYPPBFTMKLGA-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SSYUTAXWVQELNV-UHFFFAOYSA-N CN1N=C(C(=C1O)C(C1=C(C(=C(C(=C1)Cl)C)Cl)Cl)=O)C Chemical compound CN1N=C(C(=C1O)C(C1=C(C(=C(C(=C1)Cl)C)Cl)Cl)=O)C SSYUTAXWVQELNV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10043482A JPS58216161A (ja) | 1982-06-11 | 1982-06-11 | ４−ベンゾイル−５−ヒドロキシピラゾ−ル系化合物の製造方法 |
| US06/400,025 US4415739A (en) | 1981-08-03 | 1982-07-20 | Process for producing 4-benzoylpyrazoles |
| EP82106626A EP0071833B1 (fr) | 1981-08-03 | 1982-07-22 | Procédé pour la préparation de benzoyl-4 pyrazoles |
| DE8282106626T DE3275376D1 (en) | 1981-08-03 | 1982-07-22 | Process for producing 4-benzoylpyrazoles |
| KR8203397A KR860001084B1 (ko) | 1981-08-03 | 1982-07-29 | 4-벤조일-5-히드록시 피라졸게 화합물의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10043482A JPS58216161A (ja) | 1982-06-11 | 1982-06-11 | ４−ベンゾイル−５−ヒドロキシピラゾ−ル系化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58216161A JPS58216161A (ja) | 1983-12-15 |
| JPH038343B2 true JPH038343B2 (fr) | 1991-02-05 |
Family
ID=14273840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10043482A Granted JPS58216161A (ja) | 1981-08-03 | 1982-06-11 | ４−ベンゾイル−５−ヒドロキシピラゾ−ル系化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58216161A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106751229B (zh) * | 2017-02-23 | 2019-04-30 | 湖北工业大学 | 一种含有杂环类有机物及多元醇复合pvc热稳定剂的组合物及其制备方法 |
-
1982
- 1982-06-11 JP JP10043482A patent/JPS58216161A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58216161A (ja) | 1983-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019081748A (ja) | ハロゲン化合物の製造方法 | |
| JPH038343B2 (fr) | ||
| JP2003335735A (ja) | パーフルオロイソプロピルアニリン類の製造方法 | |
| JP3948745B2 (ja) | ３，５−ジアリールピラゾールの製造 | |
| JP4467890B2 (ja) | チオフェンのクロロメチル化 | |
| JPS6335625B2 (fr) | ||
| EP0071833B1 (fr) | Procédé pour la préparation de benzoyl-4 pyrazoles | |
| JPH0616613A (ja) | ２−クロル−４，５−ジフルオルベンゾニトリル及び その製法 | |
| JP6124015B2 (ja) | ペンタフルオロスルファニル安息香酸の製造方法 | |
| JPS59110649A (ja) | α−ビニルプロピオン酸エステルの製法 | |
| JP2001181228A (ja) | ポリ−（フルオロアルキル）−アセトフェノンの製造方法 | |
| JP4221782B2 (ja) | ジハロトリフルオロアセトンの精製方法 | |
| JP2853929B2 (ja) | ２−クロロ−４，５−ジフルオロ−３−メトキシ安息香酸の製造方法 | |
| JP2003517029A (ja) | トリフルオロメチルアセトフェノンの製造方法 | |
| JP3242253B2 (ja) | アゾアルカン誘導体の製造法 | |
| HU186389B (en) | Process for producing chlorinated derivatives of benzoxazolone | |
| JP3122334B2 (ja) | トリメチルシリルプロピナールの製造方法 | |
| JPH08208623A (ja) | イミダゾール系化合物の製造方法 | |
| JPS59227864A (ja) | ピラゾ−ル誘導体の製造方法 | |
| JPH07215913A (ja) | ２，４，５−トリハロゲノ−３−メチル安息香酸の製造方法 | |
| JP2002155022A (ja) | 場合により置換基を有する塩化ビフェニルカルボニルの製造方法 | |
| JPS6232181B2 (fr) | ||
| JPS6163659A (ja) | ４−（２，４−ジクロルベンゾイル）−１−メチル−５−ヒドロキシピラゾ−ルの製造法 | |
| JPH0344375A (ja) | ５―ヒドロキシピラゾール類の製造法 | |
| WO2000061530A1 (fr) | Procede de preparation de composes halogenes |