CS264698B1 - 2-aminophenol-4-/n,3-carboxyphenyl/sulphonamid and process for preparing them - Google Patents
2-aminophenol-4-/n,3-carboxyphenyl/sulphonamid and process for preparing them Download PDFInfo
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- CS264698B1 CS264698B1 CS881299A CS129988A CS264698B1 CS 264698 B1 CS264698 B1 CS 264698B1 CS 881299 A CS881299 A CS 881299A CS 129988 A CS129988 A CS 129988A CS 264698 B1 CS264698 B1 CS 264698B1
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- Prior art keywords
- carboxyphenyl
- sulfonamide
- aminophenol
- iron
- preparing
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- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 19
- -1 3-carboxyphenyl Chemical group 0.000 claims abstract description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 11
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 6
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řešení spadá do oblasti chemie organických barviv. Cílem řešení je sloučenina 2-aminofenol-4-(N,3-karboxyfenyl)sulfonamid a způsob její přípravy. Způsob přípravy 2-aminofenol-4-(N,3-karboxyfenyl)sulfonamidu vzorce spočívá v tom, že se 2-nitrofenol-4-(N,3-karboxyfenyl)sulfonamid redukuje ve vodném prostředí směsí železa a kyseliny chlorovodíkové nebo směsí železa a železnatých solí kyseliny chlorovodíkové nebo sírové při teplotě 90 až 100 °C. IThe solution is in the field of organic chemistry dyes. The aim of the solution is 2-aminophenol-4- (N, 3-carboxyphenyl) sulfonamide and the way its preparation. Process for preparing 2-aminophenol-4- (N, 3-carboxyphenyl) sulfonamide the formula is that 2-nitrophenol-4- (N, 3-carboxyphenyl) sulfonamide reduced in an aqueous environment a mixture of iron and hydrochloric acid or mixtures of iron and ferrous acid salts hydrochloric or sulfuric acid at a temperature of 90 to 100 ° C. AND
Description
Vynález se týká 2-aminofenoI-4-(N,3-karboxyfenyl)sulfonamidu a způsobu jeho výroby.The present invention relates to 2-aminophenyl-4- (N, 3-carboxyphenyl) sulfonamide and to a process for its preparation.
K barvení vlny a polyamidu se používají kovokomplexní azobarviva, kde se jako aktivní komponenty používá Íiiiiinoíenol 4 suitou amid nebo 2-aminofenol-4-N-metylsulfonainid.Metal-complex azo dyes are used for dyeing wool and polyamide, wherein the active component is a 4-amide or 2-aminophenol-4-N-methylsulfonainide active ingredient.
Nyní byla připravena sloučenina 2-aminofenol-4-(N,3-karboxyfenyl)sulfonamid, která má obdobné použití.A 2-aminophenol-4- (N, 3-carboxyphenyl) sulfonamide compound having similar uses has now been prepared.
Způsob přípravy 2-aminofenol-4-(N,3-karboxyfenyi)sulfonamidu vzorce lA process for preparing 2-aminophenol-4- (N, 3-carboxyphenyl) sulfonamide of Formula 1
spočívá v tom, že se ve vodném prostředí redukuje 2-nitrofenol-4-(N,3-karboxyfenyl)sulfonamid směsí železa a kyseliny chlorovodíkové nebo směsí železa a železnatých solí kyseliny chlorovodíkové nebo sírové při teplotě 90 až 100 °C.The process of claim 2 wherein the aqueous medium is to reduce 2-nitrophenol-4- (N, 3-carboxyphenyl) sulfonamide with a mixture of iron and hydrochloric acid or a mixture of iron and ferrous salts of hydrochloric or sulfuric acid at a temperature of 90-100 ° C.
Vzniklá směs suspenze aminolátky a redukčních produktů (redukční kaly) se oddělí tak, že se aminolátka převede alkalizací hydroxidem sodným do roztoku a pevná suspenze se izoluje filtrací. Látka vzorce I se vyloučí z roztoku vykyselením vhodnou kyselinou, např. kyselinou chlorovodíkovou.The resulting mixture of the amino compound slurry and the reducing products (reducing sludge) was separated by converting the amino compound into alkaline solution with sodium hydroxide and isolating the solid suspension by filtration. The compound of formula I is precipitated from the solution by acidification with a suitable acid, e.g. hydrochloric acid.
CS 264 698 BlCS 264 698 Bl
Průběh konverze není provázen vedlejšími reakcemi. Po izolaci se získá látka vzorce I s teplotou tání 253 až 255 °C. Diazotační a následnou kopulační titrací této látky byla potvrzena přítomnost aromaticky vázaného aminu a stanovena relativní molární hmotnost 308.The conversion process is not accompanied by side reactions. After isolation, the compound of formula I is obtained having a melting point of 253-255 ° C. Diazotization and subsequent coupling titration of this compound confirmed the presence of an aromatically bound amine and determined the relative molar mass of 308.
Provedení podle vynálezu upřesňuje dále uvedený příklad.An embodiment of the invention is illustrated by the following example.
PříkladExample
Do 60 ml vody se za stálého míchání vnese 40 g železných pilin, vyhřeje na 80 °C a pomalu se přidají 4 ml kyseliny chlorovodíkové o koncentraci c(HCl) = 9 mol/1. Reakční směs se vyhřeje na teplotu 85 až 90 °C a nechá se při této teplotě 30 minut míchatTo 60 ml of water, 40 g of iron filings are added while stirring, heated to 80 ° C and 4 ml of hydrochloric acid with a concentration of c (HCl) = 9 mol / l are slowly added. The reaction mixture was heated to 85-90 ° C and allowed to stir at this temperature for 30 minutes
Potom se teplota upraví na 95 až 100 °C a zvolna se vnese během 4,5 hodin 33,8 g 100% 2-nitrofenol-4-(N,3-karboxyfenyl)sulfonamidu (0,1 mol). Po nadávkování se nečítá směs 3 hodiny doreagovat při teplotě 100 °C.The temperature is then adjusted to 95-100 ° C and slowly added over 4.5 hours with 33.8 g of 100% 2-nitrophenol-4- (N, 3-carboxyphenyl) sulfonamide (0.1 mol). After dosing, the mixture did not count for 100 hours at 100 ° C.
Po ukončení redukce se suspenze převede do roztoku hydroxidem sodným o koncentraci c(NaOH) = 10 mol/1 a případným naředěním vodou. Po alkalizaci má roztok konečné pH 11 až 12,5.After the reduction is complete, the suspension is taken up in solution with sodium hydroxide c (NaOH) = 10 mol / l and possible dilution with water. After alkalization, the solution has a final pH of 11 to 12.5.
Roztok se vyhřeje na 100 °C, krátce se vymíchá a redukční kaly se oddělí filtrací. Filtrát se ochladí na teplotu 10 až 20 °C, zvolna se vykyselí kyselinou chlorovodíkovou a produkt se izoluje filtrací. Filtrační koláč se promyje vodou do ztráty kyselé reakce filtrátů.The solution is heated to 100 ° C, stirred briefly and the reducing sludges are separated by filtration. The filtrate is cooled to 10-20 ° C, acidified slowly with hydrochloric acid and the product isolated by filtration. The filter cake was washed with water until the acidic reaction of the filtrates was lost.
Získá se 26 g produktu vzorce 1 s výše uvedenou t.t.26 g of the product of formula 1 with the above m.p.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881299A CS264698B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-/n,3-carboxyphenyl/sulphonamid and process for preparing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881299A CS264698B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-/n,3-carboxyphenyl/sulphonamid and process for preparing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS129988A1 CS129988A1 (en) | 1988-11-15 |
| CS264698B1 true CS264698B1 (en) | 1989-08-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS881299A CS264698B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-/n,3-carboxyphenyl/sulphonamid and process for preparing them |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS264698B1 (en) |
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1988
- 1988-03-01 CS CS881299A patent/CS264698B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS129988A1 (en) | 1988-11-15 |
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