CS197937B1 - Process for the separation of 2-phenyl-4,5-dichlor-pyridazin-3-one - Google Patents
Process for the separation of 2-phenyl-4,5-dichlor-pyridazin-3-one Download PDFInfo
- Publication number
- CS197937B1 CS197937B1 CS423678A CS423678A CS197937B1 CS 197937 B1 CS197937 B1 CS 197937B1 CS 423678 A CS423678 A CS 423678A CS 423678 A CS423678 A CS 423678A CS 197937 B1 CS197937 B1 CS 197937B1
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- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- dichloropyridazin
- solvent
- solution
- aromatic hydrocarbons
- Prior art date
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- 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 title claims description 14
- 238000000034 method Methods 0.000 title claims description 5
- 238000000926 separation method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000012454 non-polar solvent Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical compound OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 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 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 3
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 3
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 3
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
Predmetom vynálezu je sposob separácie 2-fenyl-4,5-<3ichlórpyridazín-3-ónu z jeho roztoku v inertnom nepolámom rozpustidle.The present invention provides a process for separating 2-phenyl-4,5- [3-chloropyridazin-3-one from a solution thereof in an inert, non-polar solvent.
2-fenyl-4,5-dichlórpyridazín-3-ón je východiskovým produktom pri výrobě herbicídneho přípravku do cukrovky s účinnou látkou 2-fenyl-4-chlór-5-amínopyridazín-3-ón.2-Phenyl-4,5-dichloropyridazin-3-one is the starting product in the manufacture of a herbicidal preparation for diabetes with the active ingredient 2-phenyl-4-chloro-5-aminopyridazin-3-one.
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Podía doteraz znánych postupov výroby sa 2-fenyl-4,5-dichlórpyridazín-3-ón izoloval z reakčného prostredia filtráciou (USA pat. 2,628.181, Brit. pat. 881.616, Franc. pat. 1.261.605).According to prior art processes, 2-phenyl-4,5-dichloropyridazin-3-one was isolated from the reaction medium by filtration (U.S. Pat. 2,628,181, British Pat. 881.616, French Pat. 1.261.605).
Podlá čs. autorského osviedčenia č. 192 282 sa výroba 2-fenyl-4,5-dichlórpyridazín-3-ónu uekutočňujá reakciou mukochlórovej kyseliny a fenylhydrazínhydrochloridu vo vodnom prostředí za přítomnosti inertného nepolárného rozpustidla.Podlá čs. of the author's certificate no. 192,282, the preparation of 2-phenyl-4,5-dichloropyridazin-3-one is carried out by reacting mucochloric acid and phenylhydrazine hydrochloride in an aqueous medium in the presence of an inert non-polar solvent.
Vzniknutý 2-fenyl-4,5-dichlórpyridazín-3-ón rozpuštěný v inertnom nepolárnom rozpustidle sa oddělí od vody a izoluje sa z rozpustidla například azeotropickou destiláciou a vodou, alebo priamym oddestilovaním pokial rozpustidlo je z radu alifatických uhlovodíkov.The resulting 2-phenyl-4,5-dichloropyridazin-3-one dissolved in an inert nonpolar solvent is separated from water and isolated from the solvent by, for example, azeotropic distillation and water, or by direct distillation if the solvent is a series of aliphatic hydrocarbons.
Je známe, že aromatické uhlovodíky a halogenované aromatické uhlovodíky sa nedajú oddeatilovať z 2-fenyl-4,5-úiehlórpyridazín-3-ónu asi při teplote do 250 °C.It is known that aromatic hydrocarbons and halogenated aromatic hydrocarbons cannot be distilled off from 2-phenyl-4,5-fluoropyridazin-3-one at about 250 ° C.
197 937197 937
197 937197 937
Pri výrobě 2-fenyl-4-chlór-5-amínopyridazín-3-ónu například podlá če. pat, 120.858 je žiadúce, aby východiskový 2-fenyl-4,5-dichlórpyridazín-3-ón neobsahoval aromatické uhlovodíky, ktoré brzdia priebeh reakcie.In the preparation of 2-phenyl-4-chloro-5-aminopyridazin-3-one, for example, according to U.S. Pat. U.S. Pat. No. 120,858, it is desirable that the starting 2-phenyl-4,5-dichloropyridazin-3-one should not contain aromatic hydrocarbons that inhibit the reaction.
Teraz aa zistilo, že postupom podlá vynálezu je možná separovat 2-feny 1-4,5-dichlórpyridazín-3-ón z roztoku v inertrom nepolárnom rozpuatidle zo skupiny zahrnujúoej aromatické uhlovodíky a halogenované aromatické uhlovodíky, ak sa do zahuštěného 2-feny1-4,5-dichlórpyridazín-3-ónu a obsahom 30 až 1 $ rozpuatidle pri teplote 160 až 230 °C pod hladinu zavádza vodná para o teplote 100 až 180 Zmes deatilačnýeh pár rozpúžtadla sa odvádza z prostredia separácie a získaný 2-fenyl-4,5-dichlórpyridazín-3-*ón odtéká vo formě taveniny.It has now been found that by the process of the invention it is possible to separate 2-phenyl-1,4,5-dichloropyridazin-3-one from a solution in an inert, nonpolar solvent from the group consisting of aromatic hydrocarbons and halogenated aromatic hydrocarbons when the concentrated 2-phenyl-4 , 5-dichloropyridazin-3-one and containing 30 to 10% of the solvent at 160 to 230 ° C below the water level are introduced into water vapor at a temperature of 100 to 180. The solvent distillation vapor mixture is removed from the separation medium and the 2-phenyl-4,5 Dichloropyridazin-3-one flows as a melt.
Izolovaný 2-fenyl-4,5-dichlórpyridazín-3-ón vo formě taveniny je možná okamžité použit pre přípravu 2-fenyl-4-chlór-5-amínopyridazín-3-ónu podlá čs. patentu č. 120858.The isolated 2-phenyl-4,5-dichloropyridazin-3-one in the form of a melt may be used immediately to prepare 2-phenyl-4-chloro-5-aminopyridazin-3-one according to U.S. Pat. U.S. Patent No. 5,768,549; 120,858th
Separácia je jednoduchá a je možné uskutočnit ju aj kontinuitne. Postupom podlá vynálezu sa odstráni nepříjemná manipulácia pri filtrácii 2-fenyl-4,5-dichlórpyridázín-3-ónu, ktorého toxické účinky sú známe.The separation is simple and can also be carried out continuously. The present invention eliminates the nuisance of filtering 2-phenyl-4,5-dichloropyridazin-3-one whose toxic effects are known.
Nasledujúce příklady osvetlujú, ale v ničom neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.
PřikladlEXAMPLE
Zmes 33,9 g mukochlórovej tyseliny 99 fcnej, 392 g vodného roztoku fenylhydrazínhydro' chloridu 7,75 %ného a 250 ml chlórbenzénu sa udržuje pri teplote refluxu za miežania po dobu 2 hodin. Zmes sa ochladí na 80 °C a chlórbenzénový roztok 2-fenyl-4,5-diehLórpyridazín-3-ónu sa oddělí od vodnej vrstvy. Chlórbenzénový roztok sa zahustí za miežania na ole· jovom kúpeli. Po dosiahnutí 200 % teploty vo varníku zavádza sa vodná para, pradohriata na 150 °C pod hladinu. Tým sa odstránia posledné zbytky chlórbenzénu z taveniny 2-fenyl-4,5-dichlórpyridazín-3-ónu, ktorý sa získá vo výtažku 46,5 g čistoty 96,3 %,A mixture of 33.9 g of 99% mucochloric acid, 392 g of 7.75% phenylhydrazine hydrochloride aqueous solution and 250 ml of chlorobenzene is maintained at reflux temperature for 2 hours. The mixture was cooled to 80 ° C and the chlorobenzene solution of 2-phenyl-4,5-dichloropyridazin-3-one was separated from the aqueous layer. The chlorobenzene solution is concentrated while stirring in an oil bath. After reaching 200% of the temperature in the kettle, steam is introduced, preheated to 150 ° C below the surface. This removes the last chlorobenzene residue from the 2-phenyl-4,5-dichloropyridazin-3-one melt, which is obtained in a yield of 46.5 g of 96.3% purity,
Příklad 2Example 2
Zmes 33,9 g mukochlórovej kyseliny 99 %nej, 50 g vody a 392 g vodného roztoku fenylhydrazínhydrochloridu 7,75 ftnáho sa udržuje za miežania pri teplote 90 až 100 °C po dobu 2 hodin. Po uplynutí reakčnej doby přidá sa 250 g xylénu a upraví aa teplota zmesi na 85 °C. Vodný podiel sa oddělí od xylénového roztoku 2-fenyl-4,5-dichlórpyridazln-3-ónu, ktorý sa zahustí na olejovom kúpeli do dosiahnutia teploty vo varníku 190 °C. K zbytku pod hladinu za miežania sa zavádza mokrá vodná para teploty 100 °C, čím sa vydestiluje zbytkový xylén v množstve 10 g. Získá sa 47,2 g taveniny 2-fenyl-4,5-diohlórpyridazín-3-ónu čistoty 96,5A mixture of 33.9 g of 99% mucochloric acid, 50 g of water and 392 g of an aqueous solution of phenylhydrazine hydrochloride of 7.75 php is kept under stirring at 90-100 ° C for 2 hours. After the reaction time, 250 g of xylene are added and the mixture is brought to a temperature of 85 ° C. The aqueous portion was separated from the xylene solution of 2-phenyl-4,5-dichloropyridazin-3-one, which was concentrated in an oil bath to a boiling temperature of 190 ° C. Wet water vapor at a temperature of 100 ° C was introduced to the residue below the sieve level, distilling off the residual xylene in an amount of 10 g. 47.2 g of a 2-phenyl-4,5-diohoropyridazin-3-one melt of 96.5 are obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS423678A CS197937B1 (en) | 1978-06-28 | 1978-06-28 | Process for the separation of 2-phenyl-4,5-dichlor-pyridazin-3-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS423678A CS197937B1 (en) | 1978-06-28 | 1978-06-28 | Process for the separation of 2-phenyl-4,5-dichlor-pyridazin-3-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197937B1 true CS197937B1 (en) | 1980-05-30 |
Family
ID=5384626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS423678A CS197937B1 (en) | 1978-06-28 | 1978-06-28 | Process for the separation of 2-phenyl-4,5-dichlor-pyridazin-3-one |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS197937B1 (en) |
-
1978
- 1978-06-28 CS CS423678A patent/CS197937B1/en unknown
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