CS226789B1 - Method of preparing 2-cyan-4-nitrobenzenediazoniumsulphate - Google Patents
Method of preparing 2-cyan-4-nitrobenzenediazoniumsulphate Download PDFInfo
- Publication number
- CS226789B1 CS226789B1 CS500582A CS500582A CS226789B1 CS 226789 B1 CS226789 B1 CS 226789B1 CS 500582 A CS500582 A CS 500582A CS 500582 A CS500582 A CS 500582A CS 226789 B1 CS226789 B1 CS 226789B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- cyano
- nitroaniline
- acid
- sulfuric acid
- diazotization
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 claims description 10
- 238000006193 diazotization reaction Methods 0.000 claims description 8
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- FZNMOMVJDPDJAN-UHFFFAOYSA-L 2-cyano-4-nitrobenzenediazonium;sulfate Chemical compound [O-]S([O-])(=O)=O.[O-][N+](=O)C1=CC=C([N+]#N)C(C#N)=C1.[O-][N+](=O)C1=CC=C([N+]#N)C(C#N)=C1 FZNMOMVJDPDJAN-UHFFFAOYSA-L 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 2
- 239000001099 ammonium carbonate Substances 0.000 claims description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález se týká přípravy 2-kyan-4-nitrobenzendiažoniumsulfatu vzorceThe invention relates to the preparation of 2-cyano-4-nitrobenzenediazonium sulphate of the formula
který se používá jako aktivní komponenta při kopulaci některých, disperzních azobarviv.which is used as an active component in the coupling of some, disperse azo dyes.
Příprava této komponenty se provádí diazotací 2-kyan-4-nitroanilínu, který se chová jako velmi slabá zásada, takže je nutno provádět jeho diazotaci v koncentrované kyselině. Známým technickým postupem diazotace slabě zásaditých aminů je vnášení suché, jemně rozemleté zásady do předloženého roztoku kyseliny nitrosylsírové v přebytku koncentrované kyseliny sírové.The preparation of this component is carried out by diazotization of 2-cyano-4-nitroaniline, which behaves as a very weak base, so it is necessary to carry out its diazotization in concentrated acid. A known technique for diazotizing weakly basic amines is to introduce a dry, finely ground base into the present nitrosylsulfuric acid solution in excess of concentrated sulfuric acid.
Nevýhodou tohoto postupu je nutnost použití značného přebytku koncentrované kyseliny sírové pro poměrně špatnou rozpustnost 2-kyan-4-nitroanilínu, jehož zanášení do nitrosylsírová kyseliny je ztíženo vysokou specifickou hmotností předložených kyselin. Prášek vnášeni aminu zůstává v důsledku toho i při dobrém míchání na hladině, stržením pod hladinu vytváří hrubé žmolky uvnitř suché, obalené lepivou a slizovitou vrstvou, v důsledku čehož není dokonalé prodiazotování veškerého aminu ani po 24 hodinách míchání prakticky skončeno.The disadvantage of this process is the necessity to use a large excess of concentrated sulfuric acid because of the relatively poor solubility of 2-cyano-4-nitroaniline, which introduction into nitrosylsulphuric acid is hampered by the high specific gravity of the present acids. As a result, the amine introducing powder remains coarse even when well mixed, drawing down below the surface to form coarse lumps inside dry, encased in an adhesive and mucilaginous layer, so that the perfect pro-diazotization of all the amine is virtually complete even after 24 hours of stirring.
Tyto nevýhody řeší způsob přípravy 2-kyan-4-nitrobenzendiazoniumsulfátu diazotacíThese disadvantages are solved by a process for the preparation of 2-cyano-4-nitrobenzenediazonium sulfate by diazotization
2-kyan-4-nitroanilínu podle vynálezu tím, že se diazotace do kyseliny nitrosylsírové, rozpuštěné v kyselině sírové, vnáší suchý práSek 2-kyan-4-nitroanilínu současně s 0,1 až 10%2-Cyano-4-nitroaniline according to the invention by introducing a diazotization into nitrosylsulphuric acid dissolved in sulfuric acid by introducing a dry powder of 2-cyano-4-nitroaniline simultaneously with 0.1 to 10%
226 789226 789
226 789 kyselého nebo normálního uhličitanu alkalického kovu a/nebo uhličitanu amonného, vztaženo na hmotnost 2-kyan-4-nitroanilínu. V roztoku kyseliny nitrosylsírové v kyselině sírové připadá na 140 g kyseliny nitrosylsírové 900 až 1 200 g kyseliny sírové a suchý prášek 2-kyan-4-nitroanilínu se s výhodou před diazotací zhomogenizuje,s použitým uhličitanem.226,789 acidic or normal alkali metal carbonate and / or ammonium carbonate based on the weight of 2-cyano-4-nitroaniline. In a solution of nitrosylsulphuric acid in sulfuric acid, 140 g of nitrosylsulphuric acid account for 900 to 1200 g of sulfuric acid, and the dry powder of 2-cyano-4-nitroaniline is preferably homogenized prior to diazotization with the carbonate used.
Výhody postupu podle vynálezu spočívají v odstranění tvorby uzavřených shluků neprodiazotované zásady. Diazotace probíhá za těchto okolností natolik hladce, že je možno doposud užívané množství 1 200 až 1 500 g koncentrované kyseliny sírové na 1 mol použité zásady snížit až na 900 g. Bghem 1 až 4 hodin se získá dokonale prodiazotováný produkt, beze zbytku rozpustný v ledové vodě a schopný kopulace s vhodnými pasivními komponentami k získání azobarviv ve vysokém výtěžku.Advantages of the process according to the invention are the elimination of the formation of closed clumps of unprodiazated base. The diazotization proceeds so smoothly in these circumstances that the amount of 1200 to 1500 g of concentrated sulfuric acid used per mole of base used so far can be reduced to 900 g. Bghem for 1 to 4 hours gives a perfectly prodiazotized product, completely soluble in ice water and capable of coupling with suitable passive components to obtain azo dyes in high yield.
PříkladExample
Do 230 g koncentrované kyseliny sírové se vnáší 14 g bezvodé, jemně rozetřeného dusičnanu sodného za případného přihřátí na 65 až 70 °C do úplného rozpuštění. Vzniklá nitrosylsírová kyselina se ochladí na 0 až 5 °C,- do které se během 1/2 až 1 hod. vnáší 32,6 g 2-kyan-4-nitroanilínu jemně rozemletého se dokonale promíchá s 3 % kyselého uhličitanu sodného tak, aby teplota nepřestoupila 10 °C ae míchá ještě 2 hodiny, kdy kapka odebraného vzorku se rozpustí v malém množství,ledové Vody beze zbytku. Reakční směs nalitá opatrně na 800 g ledu dává bledě žlutý roztok diazoniové sloučeniny, kterou lže ihned zpracovat s pasivní komponentou na příslušně ůzobarvivo.14 g of anhydrous, finely divided sodium nitrate are introduced into 230 g of concentrated sulfuric acid, possibly warming to 65 to 70 ° C until complete dissolution. The resulting nitrosylsulphuric acid is cooled to 0-5 ° C, to which 32.6 g of finely divided 2-cyano-4-nitroaniline is introduced in 1/2 to 1 hour, thoroughly mixed with 3% sodium bicarbonate so that the temperature did not exceed 10 ° C and was stirred for a further 2 hours, when a drop of the sample was dissolved in a small amount of ice water. The reaction mixture poured cautiously onto 800 g of ice gives a pale yellow solution of the diazonium compound, which can be immediately processed with the passive component into the corresponding dye.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS500582A CS226789B1 (en) | 1982-07-01 | 1982-07-01 | Method of preparing 2-cyan-4-nitrobenzenediazoniumsulphate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS500582A CS226789B1 (en) | 1982-07-01 | 1982-07-01 | Method of preparing 2-cyan-4-nitrobenzenediazoniumsulphate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226789B1 true CS226789B1 (en) | 1984-04-16 |
Family
ID=5394070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS500582A CS226789B1 (en) | 1982-07-01 | 1982-07-01 | Method of preparing 2-cyan-4-nitrobenzenediazoniumsulphate |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS226789B1 (en) |
-
1982
- 1982-07-01 CS CS500582A patent/CS226789B1/en unknown
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