CS233226B1 - Method of 4,5-dichlorine-1-phenyl-1-6-oxo-1h-pyridazine making - Google Patents
Method of 4,5-dichlorine-1-phenyl-1-6-oxo-1h-pyridazine making Download PDFInfo
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- CS233226B1 CS233226B1 CS312583A CS312583A CS233226B1 CS 233226 B1 CS233226 B1 CS 233226B1 CS 312583 A CS312583 A CS 312583A CS 312583 A CS312583 A CS 312583A CS 233226 B1 CS233226 B1 CS 233226B1
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- Czechoslovakia
- Prior art keywords
- oxo
- phenyl
- pyridazine
- dichloro
- preparation
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 9
- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002955 isolation Methods 0.000 claims abstract description 4
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 claims description 10
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 claims description 10
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 5
- 229940067157 phenylhydrazine Drugs 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- GXIWMALOYDSQMW-UHFFFAOYSA-N ClCl(=O)=O Chemical compound ClCl(=O)=O GXIWMALOYDSQMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000011888 foil Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 4
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XTDAAEAUAXRJLR-UHFFFAOYSA-N 2-phenyl-4,5-dihydropyridazin-3-one Chemical compound O=C1CCC=NN1C1=CC=CC=C1 XTDAAEAUAXRJLR-UHFFFAOYSA-N 0.000 description 1
- BFOMTEBFEFQJHY-UHFFFAOYSA-N 2-phenylpyridazin-3-one Chemical compound O=C1C=CC=NN1C1=CC=CC=C1 BFOMTEBFEFQJHY-UHFFFAOYSA-N 0.000 description 1
- VUTBELPREDJDDH-UHFFFAOYSA-N 4-amino-5-hydroxymethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CO)C(N)=N1 VUTBELPREDJDDH-UHFFFAOYSA-N 0.000 description 1
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
Abstract
Vynález ee týká apSaobu výroby 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu reakciou kyseliny «ukochlorovej a fenylhydrezínu v prostředí zriedenej kyseliny chlorovodíkové!, diekontlnuélnýa alebo kontinuálny* epoeobom v prietokovo* reaktore, pričoa netečný roztok zlzkaný po izolácii reakciou vzniknutého 4,5-dichlor-1-fenyl- -6-oxo-1H-pyrldazlnu za opatovné pouáije k jeho výrobě. Uvedená zlúčenlnu je nožno použit ako aedziprodukt pri výrobě herblcldneho přípravku Burexu.The invention relates to the preparation of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine reaction chlorochloric acid and phenylhydrezine in dilute hydrochloric acid! continuous or continuous * epoeobom in a flow reactor, praoa an inert solution leached after isolation by reacting the resulting 4,5-dichloro-1-phenyl- -6-oxo-1 H -pyridazine is used with caution its production. The compound is used as a foil and an intermediate in the manufacture of a drug composition Burex.
Description
Vynález sa týká spdsobu výroby 4,5-diehlór-1-fenyl-6-oxo-1H-pyridazínu.The present invention relates to a process for the preparation of 4,5-dihydro-1-phenyl-6-oxo-1H-pyridazine.
4,5-dlchlór-1-fenyl-6-oxo-1H-pyridazín je medzlproduktom pri výrobě herbicidnáho přípravku (Burex, Pyramín).4,5-Chloro-1-phenyl-6-oxo-1H-pyridazine is an intermediate product in the manufacture of a herbicidal preparation (Burex, Pyramine).
Doteraz sú známe viacere spdsoby přípravy 4,5-dichlór-1-fenyl-6-oxo~1H-pyridazinu. PodTa DAS 1 086 278 příprava sa uskutoCnl reakciou kyseliny mukochlorovej a fenylhydrazlnu v prostředí organického rozpúšťadla. Čs. AO 205 592 popisuje reakciu kyseliny mukochlorovej s fenylhydrazlnom v zmesi organického nepolárného rozpúšťadla a vody. PodTa USA pat.Several methods for the preparation of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine are known to date. According to DAS 1 086 278, the preparation is carried out by reacting mucochloric acid and phenylhydrazine in an organic solvent medium. MS. AO 205 592 describes the reaction of mucochloric acid with phenylhydrazylic acid in a mixture of an organic non-polar solvent and water. According to US Pat.
628 181 sa uskutoční reakcia mukochlorovej kyseliny a fenylhydrazínhydrochloridu vo vodě za přítomnosti uhličitanu sodného, pričom vzniklnutý produkt fenylhydrazon kyseliny mukochlorovej sa izoluje a varom v ladovej kyselino octovej sa prevedie na 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazín.628 181, the reaction of mucochloric acid and phenylhydrazine hydrochloride in water in the presence of sodium carbonate is isolated and the resulting phenylhydrazone mucochloric acid product is isolated and boiled in glacial acetic acid to give 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine .
Ďalšie známe postupy výroby 4,5-diehlór-1-fenyl-6-oxo-1H-pyridazinu spočívajú v reakci! mukochlorovej kyseliny a fenylhydrazínu v prostředí zriedenej minerálnej kyseliny (Brit. pat. č. 881 616; DOS 1 545 595; čs. AÓ 220 299). Společným znakom doterajších postupov je, že pri výrobě 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu a po izolácii technického produktu ostávájú kvapalné odpady znečisťujúce životné prostredie, v ktorých je rozpuštěná časť vyrobeného 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazinu.Other known processes for the preparation of 4,5-dichloro-1-phenyl-6-oxo-1 H -pyridazine involve the reaction of a compound of formula I. mucochloric acid and phenylhydrazine in a dilute mineral acid medium (Brit. Pat. No. 881 616; DOS 1 545 595; No. AO 220 299). A common feature of the prior art is that in the production of 4,5-dichloro-1-phenyl-6-oxo-1 H -pyridazine and after isolation of the technical product, liquid environmental wastes remain in which part of the produced 4,5-dichloro-2-ol is dissolved. 1-phenyl-6-oxo-1 H-pyridazine.
Terez sa našiel spdsob výroby 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu reakciou kyseliny mukochlorovej a fenylhydrazlnu v prostředí zriedenej kyseliny chlorovodíkovej kontinuálně alebo dlskontinuálne, spdsobom podTa vynálezu.A process for the preparation of 4,5-dichloro-1-phenyl-6-oxo-1 H -pyridazine by reacting mucochloric acid and phenylhydrazine in dilute hydrochloric acid continuously or in a batchwise manner according to the invention has been found.
Podstata vynálezu spočívá v tom, že matečný roztok získaný po Izolácii reakciou vzniknutého 4,5-diehlór-1-fenyl-6-oxo-1H-pyrldazínu sa opatovne použije k jeho výrobě.SUMMARY OF THE INVENTION The mother liquor obtained after isolation of the resulting 4,5-dichloro-1-phenyl-6-oxo-1H-pyrldazine is carefully used for its preparation.
Výhoda nového postupu výroby 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu spočívá v takmer jeho bezodpadovom epdsobe výroby, čo má velký význam pri ochraně životného prostredia, najma, Že nezreagovaný fenylhydrezín ako zvlášť nebezpečný jed se prakticky nedostává do odpadových vdd. Je.potřebné áalej zddrazniť tú skutočnosť, že pri výrobě 4,5-dichlór-1-fenyl-6-oxo-1H-pyrldazínu podTa vynálezu v matečnom roztoku rozpustný 4,5-dlchlór-l-fenyl-6-oxo-1H-pyridazin sa opatovne použije pri reakcii čo sa odzrkadTuje v nižších stratách daných jeho rozpustnosťou. ’The advantage of the new process for the production of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine lies in its almost waste-free production process, which is of great importance in environmental protection, in particular that unreacted phenylhydrezine as a particularly dangerous poison is virtually absent. to waste vdd. It should be further emphasized that, in the preparation of 4,5-dichloro-1-phenyl-6-oxo-1H-pyrldazine according to the invention, soluble 4,5-dichloro-1-phenyl-6-oxo-1H- pyridazine is used cautiously in the reaction, which is reflected in lower losses due to its solubility. '
Nasledujúce příklady ilustrujú, ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the invention.
PřikladlEXAMPLE
Do reakčného kotlá sa předložilo 8,1 kg kyseliny mukochlorovej, 125 kg 1,82 %-nej kyseliny chlorovodíkovej a 99,2 kg 7 %-ného vodného roztoku fenylhydrazínhydrochloridu. Reakčné zmes se udržiava za miešania pri teplote 95 °C po dobu 1 hodiny. Technický produkt 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu sa izoloval filtráciou. Po premyti a vysušení sa získalo 10,95 kg 99 %-ného 4,5-diehlór-1-fenyl-6-oxo-1H-pyridazínu, čo zodpovědí 95 %-nému výťažku.8.1 kg of mucochloric acid, 125 kg of 1.82% hydrochloric acid and 99.2 kg of a 7% aqueous phenylhydrazine hydrochloride solution were charged to the reaction vessel. The reaction mixture is kept under stirring at 95 ° C for 1 hour. Technical product 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine was isolated by filtration. After washing and drying, 10.95 kg of 99% 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine was obtained, which corresponds to a 95% yield.
Příklad 2Example 2
Matečný roztok z pripravy 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu poplsaného v příklade 1 o hmotnosti 218,6 kg sa opať předložil do kotlá, přidalo sa 5,2 kg fenylhydrazínu a 8,1 kg kyseliny mukochlorovej. Reakčné zmes sa udržovala za miešania pri teplote 95 až 100 °C po dobu 1 hodiny. Po ochladerií reakčnej zmesi tuhý produkt sa izoloval filtráciou. Získalo sa 11,3 kg 99,1 %-ného technického produktu 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu, čo zodpovedé 96,8 %-nému výťažku.The mother liquor from the preparation of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine described in Example 1 weighing 218.6 kg was again charged to the boiler, 5.2 kg of phenylhydrazine and 8.1 kg of acid were added. mucochloric. The reaction mixture was kept under stirring at 95-100 ° C for 1 hour. After cooling the reaction mixture, the solid product was isolated by filtration. 11.3 kg of a 99.1% technical product of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine, corresponding to a 96.8% yield, were obtained.
Příklad 3Example 3
Po 30-násobnom opakovaní postupu popísanáho v příklade 2 sa získalo 11,2 kg 99,3 %-ného technického produktu 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu.After 30-fold of the procedure described in Example 2, 11.2 kg of a 99.3% technical product 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine were obtained.
Příklad 4Example 4
Do prietokového reaktora pozostévajúceho z troch kotlov vzájomne spojených y kaskádě a opatřených miešadlom sa dávkovalo hodinové 13,3 kg 6 %-ného vodného roztoku kyseliny mukochlórovej s obsahom 0,23 kg volného chlorovodíka o teplote 60 °C a 9,9 kg 7 %-ného vodného roztoku fenylhydrazínhydrochloridu. Reakčná zmes sa udržovala v reaktore pri teplote 95 °C a zádrž bola 1 h. Technický produkt 4,5-diehlór-1-fenyl-6-oxo-1H-pyridazínu sa izoloval filtráciou. Za 1 h sa získalo 1,03 kg produktu o čistotě 99 %.13.3 kg of a 6% aqueous solution of mucochloric acid containing 0.23 kg of free hydrogen chloride at a temperature of 60 ° C and 9.9 kg of 7% - was charged to the flow reactor consisting of three boilers connected to each other in a cascade and equipped with a stirrer. % of an aqueous solution of phenylhydrazine hydrochloride. The reaction mixture was held in the reactor at 95 ° C and held for 1 h. The technical product 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine was isolated by filtration. 1.03 kg of a product with a purity of 99% was obtained in 1 hour.
Matečný roztok 22,1 kg sa rozdělil následovně: 12,5 kg po doplnění s 2,6 g 31 %-nej kyseliny chlorovodíkovej sa použilo na přípravu 6 %-ného roztoku kyseliny mukochlorovej a 9,4 kg sa použ.ilo po doplnění s 12 g 31 %-nej kyseliny chlorovodíkovej na přípravu 7 %-ného roztoku fenylhydrazínhydrochloridu. Popísáným postupom sa postupovalo 360 h.The mother liquor of 22.1 kg was distributed as follows: 12.5 kg after addition with 2.6 g of 31% hydrochloric acid was used to prepare a 6% solution of mucochloric acid and 9.4 kg was used after addition with 12 g of 31% hydrochloric acid for the preparation of 7% phenylhydrazine hydrochloride solution. The procedure described was 360 h.
Po uvedenej době za 1 h sa získalo 1,05 kg technického 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu o čistotě 99,4 %.After 1 h, 1.05 kg of technical 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine was obtained with a purity of 99.4%.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS312583A CS233226B1 (en) | 1983-05-04 | 1983-05-04 | Method of 4,5-dichlorine-1-phenyl-1-6-oxo-1h-pyridazine making |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS312583A CS233226B1 (en) | 1983-05-04 | 1983-05-04 | Method of 4,5-dichlorine-1-phenyl-1-6-oxo-1h-pyridazine making |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS233226B1 true CS233226B1 (en) | 1985-02-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS312583A CS233226B1 (en) | 1983-05-04 | 1983-05-04 | Method of 4,5-dichlorine-1-phenyl-1-6-oxo-1h-pyridazine making |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS233226B1 (en) |
-
1983
- 1983-05-04 CS CS312583A patent/CS233226B1/en unknown
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