CS264797B1 - 2-aminophenol-4-/n,2 -carboxyphenyl/sulphonamide and process for preparing them - Google Patents
2-aminophenol-4-/n,2 -carboxyphenyl/sulphonamide and process for preparing them Download PDFInfo
- Publication number
- CS264797B1 CS264797B1 CS881312A CS131288A CS264797B1 CS 264797 B1 CS264797 B1 CS 264797B1 CS 881312 A CS881312 A CS 881312A CS 131288 A CS131288 A CS 131288A CS 264797 B1 CS264797 B1 CS 264797B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carboxyphenyl
- aminophenol
- sulfonamide
- iron
- mixture
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- -1 2 - -carboxyphenyl Chemical group 0.000 claims abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract 1
- LEIQLPBQKARMTD-UHFFFAOYSA-N hydron;iron(2+);chloride Chemical class [H+].[Cl-].[Fe+2] LEIQLPBQKARMTD-UHFFFAOYSA-N 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
- 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
- 239000000706 filtrate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 1
- PIEMCTWSDZKTKH-UHFFFAOYSA-N CS(=O)(=O)N.NC1=C(C=CC=C1)O Chemical compound CS(=O)(=O)N.NC1=C(C=CC=C1)O PIEMCTWSDZKTKH-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide 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
- 238000006243 chemical reaction Methods 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
- 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
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension 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,2'-karboxyfenyl)sulfonamid a způsob její přípravy. Způsob přípravy 2- -aminofenol-4-(N,2'-karboxyfeny1)sulfonamid vzorce I OH ,nh2 COOH (i) Šo2 —NH—00 spočívá v tom, že se 2-nitrofenol-4-(N,2 - -karboxyfenyl)sulfonamid redukuje ve vodném prostředí směsí železa a kyseliny chlorovodíkové nebo směsí železa a železnátých solí kyseliny chlorovodíkové nebo sírové při teplotě 95 až 100 °C.The solution is in the field of organic chemistry dyes. The aim of the solution is compound 2- -aminophenol-4- (N, 2'-carboxyphenyl) sulfonamide and the method of its preparation. Method of preparation 2- -aminophenol-4- (N, 2'-carboxyphenyl) sulfonamide of Formula I OH , nh2 COOH (i) Šo2 —NH — 00 is that 2-nitrophenol-4- (N, 2 - -carboxyphenyl) sulfonamide reduces in aqueous with the mixture of iron and acid hydrochloric acid or a mixture of iron and iron (II) hydrochloric acid salts or sulfuric acid at 95 to 100 ° C.
Description
Vynález se týká 2-aminofenol-4- (N, 2'-karboxyfenyl) sulfonamidu a způsobu jeho výroby.The present invention relates to 2-aminophenol-4- (N, 2'-carboxyphenyl) sulfonamide and to a process for its preparation.
K barvení vlny a polyamidu se používají kovokomplexní azobarviva, kde se jako aktivní komponenty používá 2-aminofenol-4-sulfonamidu nebo 2-aminofenol-4-N-metylsulfonamidu.Metal-complex azo dyes are used for dyeing wool and polyamide, wherein 2-aminophenol-4-sulfonamide or 2-aminophenol-4-N-methylsulfonamide is used as the active component.
Nyní byla připravena sloučenina 2-aminofenol-4-(N,2'-karboxyfenyl)sulfonamid, která má obdobné použití.The compound 2-aminophenol-4- (N, 2'-carboxyphenyl) sulfonamide has now been prepared for similar use.
'Způsob přípravy 2-amihofenol-4-(N,2'-karboxyfenyl)sulfonamidu vzorce IProcess for the preparation of 2-aminophenol-4- (N, 2'-carboxyphenyl) sulfonamide of formula I
OHOH
spočívá v tom, že se ve vodném prostředí redukuje 2-nitrofenol-4-(N,2'-karboxyfenyl)sulfonamid směsí železa a kyseliny chlorovodíkové nebo směsi železa a železnatých soli kyseliny chlorovodíkové nebo sírové při teplotě 95 až 100 °C.The process of claim 2 wherein the aqueous medium is to reduce 2-nitrophenol-4- (N, 2'-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 95-100 ° C.
Vzniklá směs suspenze aminolátky a redukčních produktů (redukční kaly) se oddělí tak, že se aminolátka převede alkalizací hydroxydem sodným do roztoku a pevná suspenze se izoluje filtrací. Látka vzorce I se vyloučí z roztoku vykyseléním vhodnou kyselinou, např. kyselinou chlorovodíkovou.The resulting mixture of the amino compound slurry and 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.
Průběh konverze není provázen vedlejšími chemickými reakcemi. Po izolaci se získá prakticky čistá látka vzorce I s teplotou táni 213 až 215 °C, s výtěžkem 90 % teorie. Diazotační á následnou kopulační titrací této látky byla potvrzena přítomnost aromaticky vázaného aminu a stanovena relativní molární hmotnost 308.The conversion process is not accompanied by chemical side reactions. After isolation, a practically pure compound of formula I is obtained with a melting point of 213 DEG-215 DEG C. in a yield of 90% of theory. Diazotization and subsequent coupling titration of this compound confirmed the presence of the aromatically bound amine and determined the relative molar mass 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 a 4 ml kyseliny chlorovodíkové o koncentraci c(HCl) = 9 mol/1. Reakční směs se vyhřeje na teplotu 90 až 95 °C a nechá se při této teplotě 30 minut míchat.To 60 ml of water, 40 g of iron filings and 4 ml of hydrochloric acid having a concentration of c (HCl) = 9 mol / l are added while stirring. The reaction mixture was heated to 90-95 ° C and allowed to stir at this temperature for 30 minutes.
Potom se teplota upraví na 95 až 100 °C a zvolna se vnese 33,8 g 100% 2-nitrofenol-4-(N,2'-karboxyfenyl)sulfonamidu (0,1 mol). Po nadávkováni se nechá směs 5 až 8 hodin doreagovat při teplotě 100 °C.The temperature is then adjusted to 95-100 ° C and slowly added 33.8 g of 100% 2-nitrophenol-4- (N, 2'-carboxyphenyl) sulfonamide (0.1 mol). After dosing, the mixture was allowed to react for 5 to 8 hours at 100 ° C.
Po ukončení redukce se směs převede do roztoku hydroxidem sodným o koncentraci c(NaOH) = = 10 mol/1 s případným naředěním vodou. Po alkalizací má roztok konečné pH 11 až 12,5.Upon completion of the reduction, the mixture is brought into solution with sodium hydroxide c (NaOH) = 10 mol / l, optionally diluted 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.The solution is heated to 100 ° C, stirred briefly and the reducing sludges are separated by filtration.
Filtrát se ochladí na teplotu 10 až 20 °C, zvolna se vykyselí kyselinou chlorovodíkovou a produkt se izoluje filtraci. Filtrační koláč se promyje vodou do ztráty kyselosti filtrátů.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 filtrates lost acidity.
Získá se 27,7 g produktu vzorce I o t.t. 213 až 215 °C.27.7 g of the product of formula I of m.p. Mp 213-215 ° C.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881312A CS264797B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-/n,2 -carboxyphenyl/sulphonamide and process for preparing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881312A CS264797B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-/n,2 -carboxyphenyl/sulphonamide and process for preparing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS131288A1 CS131288A1 (en) | 1988-11-15 |
| CS264797B1 true CS264797B1 (en) | 1989-09-12 |
Family
ID=5347193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS881312A CS264797B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-/n,2 -carboxyphenyl/sulphonamide and process for preparing them |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS264797B1 (en) |
-
1988
- 1988-03-01 CS CS881312A patent/CS264797B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS131288A1 (en) | 1988-11-15 |
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