CS264930B1 - 2-aminophenol-4-(n,4-carboxyphenyl/ sulphonamid and process for preparing thereof - Google Patents
2-aminophenol-4-(n,4-carboxyphenyl/ sulphonamid and process for preparing thereof Download PDFInfo
- Publication number
- CS264930B1 CS264930B1 CS881314A CS131488A CS264930B1 CS 264930 B1 CS264930 B1 CS 264930B1 CS 881314 A CS881314 A CS 881314A CS 131488 A CS131488 A CS 131488A CS 264930 B1 CS264930 B1 CS 264930B1
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- CS
- Czechoslovakia
- Prior art keywords
- carboxyphenyl
- aminophenol
- sulfonamide
- iron
- hydrochloric acid
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 13
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 11
- 229910052742 iron Inorganic materials 0.000 claims abstract description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- -1 ferrous hydrochloric acid salts Chemical class 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 5
- 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
- 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 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
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 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
Řešeni ,spadá do oblasti chemie organických barviv. Cílem řešení je sloučenina 2-aminofenol-4-(N,4'-karboxyfenyl)sulfonamid a způsob jeho přípravy. Způsob přípravy 2-aminofenol-4-(N,4'-karboxyfenyl)- sulfonamidu vzorce I spočívá v tom, že se 2-nitrofenol-4-(N,- 4'-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.The solution falls within the field of organic chemistry dyes. The goal of the solution is the compound 2-aminophenol-4- (N, 4'-carboxyphenyl) sulfonamide and the method of its preparation. Method of preparation 2-Aminophenol-4- (N, 4'-carboxyphenyl) - sulfonamide of formula I is that 2-nitrophenol-4- (N, - 4'-carboxyphenyl) sulfonamide reduces with an aqueous mixture of iron and acid hydrochloric acid or a mixture of iron and ferrous hydrochloric acid salts or sulfuric acid at 90 to 100 ° C.
Description
(57) Řešeni ,spadá do oblasti chemie organických barviv. Cílem řešení je sloučenina 2-aminofenol-4-(N,4'-karboxyfenyl)sulfonamid a způsob jeho přípravy. Způsob přípravy 2-aminofenol-4-(N,4'-karboxyfenyl)sulfonamidu vzorce I(57) The solution falls within the field of organic dye chemistry. The object of the invention is 2-aminophenol-4- (N, 4'-carboxyphenyl) sulfonamide and a process for its preparation. A process for preparing 2-aminophenol-4- (N, 4'-carboxyphenyl) sulfonamide of formula I
spočívá v tom, že se 2-nitrofenol-4-(N,4'-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.characterized in that the 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfonamide is reduced in an aqueous medium by 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 to 100 ° C.
CQCQ
O ωO ω
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CM (Z) oCM (Z) o
CS 264 930 BlCS 264 930 Bl
Vynález se týká 2-aminofenol-4-(N,4’-karboxyfenyl)sulfonamidu a způsobu jeho výroby.The invention relates to 2-aminophenol-4- (N, 4 ' -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-sulfonamid nebo 2-aminofenol-4’-N-metylsulfonamid.Metal-complex azo dyes are used for dyeing wool and polyamide, where 2-aminophenol-4-sulfonamide or 2-aminophenol-4'-N-methylsulfonamide is used as the active component.
Nyní byla připravena sloučenina 2-aminofenol-4-(N,4'-karboxyfenyl)sulfonylamid, která má obdobné použití.The compound 2-aminophenol-4- (N, 4'-carboxyphenyl) sulfonylamide has now been prepared for similar use.
Způsob přípravy 2-aminofenol-4-(N,4'-karboxyfenyl)sulfonamidu vzorce IA process for preparing 2-aminophenol-4- (N, 4'-carboxyphenyl) sulfonamide of formula I
spočívá v tom, že se ve vodném prostředí redukuje 2-nitrofenol-4-(N,4'-karboxyfenyl)sulfon amid 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 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfone amide is reduced by 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 to 100 ° C.
Vzniklá suspenze aminolátky se od produktů redukce (redukční kaly) oddělí převedením aminolátky alkalizací hydroxidem sodným do roztoku a následnou filtrací.The resulting amino compound suspension is separated from the reduction products (reducing sludge) by converting the amino compound into alkaline solution with sodium hydroxide and subsequent filtration.
Látka vzorce I se vyloučí z roztoku vykyselením vhodnou kyselinou, např. kyselinou chlorovodíkovou.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 tání 299 az 302 °C, s výtěžkem 85 % teorie. 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 chemical side reactions. After isolation, a practically pure compound of formula I is obtained with a melting point of 299 DEG -302 DEG C. in a yield of 85% of theory. 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 přidávají 4 ml kyseliny chlorovodíkové o koncentraci c(HCl) = 9 mol/1. Reakční směs se vyhřeje na 95 °C a nechá se při této teplotě 30 minut míchat.40 g of iron filings are added to 60 ml of water while stirring, heated to 80 ° C and 4 ml of hydrochloric acid having a concentration of c (HCl) = 9 mol / l are slowly added. The reaction mixture is heated to 95 ° C and allowed to stir at this temperature for 30 minutes.
Potom se teplota upraví na 100 °C a zvolna se vnese během 4 hodin 33,8 g 100% 2-nitro fenol-4-(N,4'-karboxyfenyl)sulfonamidu (0,1 mol). Po nadávkování se nechá směs 3 hodiny doreagovat při teplotě 100 °C.The temperature is then adjusted to 100 ° C and 33.8 g of 100% 2-nitro phenol-4- (N, 4'-carboxyphenyl) sulfonamide (0.1 mol) are slowly added over 4 hours. After dosing, the mixture was allowed to react for 3 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 alkalizací 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 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 26,2 g produktu vzorce I o t.t. 299 až 302 °C.26.2 g of the product of formula I of m.p. Mp 299-302 ° C.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881314A CS264930B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-(n,4-carboxyphenyl/ sulphonamid and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881314A CS264930B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-(n,4-carboxyphenyl/ sulphonamid and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS131488A1 CS131488A1 (en) | 1988-12-15 |
| CS264930B1 true CS264930B1 (en) | 1989-09-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS881314A CS264930B1 (en) | 1988-03-01 | 1988-03-01 | 2-aminophenol-4-(n,4-carboxyphenyl/ sulphonamid and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS264930B1 (en) |
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1988
- 1988-03-01 CS CS881314A patent/CS264930B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS131488A1 (en) | 1988-12-15 |
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