CS224568B1 - Method for polarographic determination 4-n-acetylaminphenol - Google Patents
Method for polarographic determination 4-n-acetylaminphenol Download PDFInfo
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- CS224568B1 CS224568B1 CS88481A CS88481A CS224568B1 CS 224568 B1 CS224568 B1 CS 224568B1 CS 88481 A CS88481 A CS 88481A CS 88481 A CS88481 A CS 88481A CS 224568 B1 CS224568 B1 CS 224568B1
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- CS
- Czechoslovakia
- Prior art keywords
- aminophenol
- acetylaminophenol
- determination
- solution
- mol
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 43
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 6
- 150000001989 diazonium salts Chemical class 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- ZRBROGSAUIUIJE-UHFFFAOYSA-N azanium;azane;chloride Chemical compound N.[NH4+].[Cl-] ZRBROGSAUIUIJE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BCESCHGDVIYYPC-UHFFFAOYSA-N 2-(ethylamino)phenol Chemical compound CCNC1=CC=CC=C1O BCESCHGDVIYYPC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011550 stock solution 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
- 229940124530 sulfonamide Drugs 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(54) Způsob polarografického stanovení 4-L-acetylaminofenolu a 4-aminofenolu vedle sebe( 54 ) Polarographic determination of 4-L-acetylaminophenol and 4-aminophenol side-by-side
224 568 . ,1..224 568. , 1 ..
224 568224 568
Vynález se týká stanovení 4-Ií-acetylaminofenolu a 4-aminofenolu vedle sebe v reakčních produktech po acetylaci 4-aminofenolu7 a to polarografickou analýzou·The invention relates to the determination of 4-N-acetylaminophenol and 4-aminophenol side-by-side in reaction products after acetylation of 4-aminophenol 7 by polarographic analysis.
4-Aminofenol je možno v reakční směsi stanovit elektroforézou na tenké vrstvě. Pro 4-H-acetylaminofenol není k dispozici doposud vhodná analytická metoda, takže analýza hlavních složek zůstává nedořešena.4-Aminophenol can be determined by thin layer electrophoresis in the reaction mixture. For 4-H-acetylaminophenol, a suitable analytical method is not yet available, so the analysis of the main components remains unresolved.
Tento nedostatek odstraňuje způsob polarografického stanovení hlavních složek v reakční směsi, a to 4-N-acetylaminofenolu a 4-aminofenolu, který podle tohoto vynálezu spočívá v tom, že se 4-N-acetylaminofenol znitrozuje na N-nitrozoderivát dusitanem sodným a 4-aminofenol na diazoniovou sůl rovněž dusitanem sodným, načež se N-nitrozoderivát stanoví v amoniakálním prostředí při potenciálu E^yg = “°»^5 V a diazoniová sůl při potenciálu E-yg = -0,60 V, popřípadě se dále diazoniová sůl rozloží v alkalickém prostředí při pH 14 a po následném polarografickém stanovení se zaznamená vlna N-nitrozoderivátu. Obě tyto látky jsou polarografioky aktivní a lze je tedy polarografioky stanovit vedle sebe.This deficiency is eliminated by the method of the polarographic determination of the main components in the reaction mixture, namely 4-N-acetylaminophenol and 4-aminophenol, which according to the invention consists in the 4-N-acetylaminophenol being nationalized to the N-nitroso derivative with sodium nitrite and 4-aminophenol to the diazonium salt also with sodium nitrite, whereupon the N-nitroso derivative is determined in an ammoniacal medium at a potential E-yg = 5 ° V and a diazonium salt at a potential E-yg = -0.60 V, optionally further decomposing the diazonium salt into The pH of the N-nitroso derivative is recorded in an alkaline medium at pH 14 and after subsequent polarographic determination. Both of these substances are polarographic and are therefore active side by side.
V prostředí chlorid amonný - amoniak o pH přibližně 9»8 se redukuje při E^yg = -0,45 V nitrozovaný 4-N-acetylaminofenol a při negativnějším potenciálu při E^yg =-0*60 V diazo 4-aminofenolu. Z polarogramu se odečte vlna diaza-4-aminofenolu a případně i vlna nitrozovaného 4-N-acetylaminofenolu. Pro snadnější odečítání vlny N-nitrozoderivátu se diazo 4-aminofenolu rozloží v alkalickém prostředí o pH 14* při laboratorní teplotě kvantitativně po 60 minutách, takže na polarogramu, získaném za analogických podmínek jak je uvedeno shora, se získá jen vlna N-nitrozoderivátu. Srovnávacími pokusy bylo prokázáno, že zaIn an ammonium chloride-ammonia medium having a pH of about 9-8, the nitrosated 4-N-acetylaminophenol is reduced at E [gamma] = -0.45 V and the diazo of 4-aminophenol at a negative potential at E [gamma] = -0 * 60 V. A wave of diaza-4-aminophenol and possibly a wave of nitrosated 4-N-acetylaminophenol are read from the polarogram. For easier reading of the N-nitroso derivative wave, the diazo of 4-aminophenol is decomposed in an alkaline medium at pH 14 * at room temperature quantitatively after 60 minutes, so that only the N-nitroso derivative wave is obtained on the polarogram obtained under analogous conditions above. Comparative experiments proved that
224 568 uvedených podmínek ae diazo 4-aminofenolu rozkládá kvantitativně, zatímco nitrozovaný 4-N-acetylaminofenol zůstává beze změny· Je výhodné odečítat vlnu diaza 4-aminofenolu v původní směsi a vlnu nitrozovaného 4-N-acetylaminofenolu po předchozím alkalickém rozkladu diaza 4-aminofenolu·224 568 of these conditions and decomposes 4-aminophenol diazo quantitatively, while nitrosated 4-N-acetylaminophenol remains unchanged · It is advantageous to read the 4-aminophenol diaza wave in the original mixture and the nitrosated 4-N-acetylaminophenol wave after previous alkaline decomposition of 4-aminophenol diaza ·
4-N-acetylaminofenol (paracetamol) je farmaceutický výrobek chemického průmyslu· Vyrábí se acetylací 4-aminofenolu v kyselém prostředí. Popisovaná polar©grafická metoda slouží ke stanovení jednak výsledného produktu - paracetamolu, jednak 4-aminofenolu v reakčních směsích.4-N-acetylaminophenol (paracetamol) is a pharmaceutical product of the chemical industry · It is produced by acetylation of 4-aminophenol under acidic conditions. The described polar graphic method serves for the determination of both the resulting product - paracetamol and 4-aminophenol in the reaction mixtures.
Příklad provedeníExemplary embodiment
Asi 15 g heterogenní reakční směsi (za předpokladu, že obsahuje cca 1 až 2 % hm. 4-aminofenolu a cca 7 až 8 % hm. 4-N-acetylaminofenolu) se odváží do 250 ml odraěmé baňky. Směs se rozpustí v cca 100 ml ledové kyseliny octové a 50 ml destilované vody a po rozpuštění se doplní po značku destilovanou vodou.About 15 g of the heterogeneous reaction mixture (assuming it contains about 1 to 2% by weight of 4-aminophenol and about 7 to 8% by weight of 4-N-acetylaminophenol) is weighed into a 250 ml volumetric flask. Dissolve the mixture in about 100 ml of glacial acetic acid and 50 ml of distilled water and make up to the mark with distilled water.
Do dvou 100 ml odměrných baněk se odpipetuje po 10 ml zásobního roztoku· Do každé baňky se přidá 2 ml koncentrované kyseliny chlorovodíkové a O,5 ml koncentrované kyseliny bromovodíkóvé. Po ochlazení na 0 až 5 °C se najednou přidá 20 ml roztoku dusitanu sodného o koncentraci c (NaNOg) =0,1 mol/1· Po jedné hodině N-nitrozace se přebytek kyseliny dusité opatrně odstraní roztokem kyseliny sulfaminové o koncentraci o (kyselina sulfaminová) = 0,1 mol/1.Pipette 10 ml of the stock solution into two 100 ml graduated flasks. 2 ml of concentrated hydrochloric acid and 0.5 ml of concentrated hydrobromic acid are added to each flask. After cooling to 0 to 5 ° C, 20 ml of sodium nitrite solution of c (NaNOg) = 0.1 mol / l are added all at once. After one hour of N-nitrosation, excess nitrous acid is carefully removed with a solution of sulfamic acid o (acid) sulfamine) = 0.1 mol / l.
Stanovení 4-aminofenolu.Determination of 4-aminophenol.
Obsah jedné odměrné baňky se opatrně zneutralizuje roztokem hydroxidu sodného o koncentraci c (NaOH) = 2 mol/1 na hodnotu pH 6 až 7. Poté se přilije 1 ml 1% hm. Syntegalu V-7 a 15 ml roztoku chlorid amonný - amoniak o koncentraci c (NH^Cl) =Carefully neutralize the contents of one volumetric flask to a pH of 6 to 7 with c (NaOH) = 2 mol / l sodium hydroxide solution. Syntegal V-7 and 15 ml of ammonium chloride-ammonia solution c (NH4Cl) =
- 1 mol/1 a c (NH^OH) = 1 mol/1. Baňka se doplní po značku destilovanou vodou. Roztok ae polarografxje při 25 °C. Roztok 4-aminofenolu o koncentraci c (4-aminofenol) = 1 · 10 J mol/1 — poskytuje za experimentálních podmínek proud 6,6 . 10 “-'A.- 1 mol / l ac (NH 4 OH) = 1 mol / l. Make up to the mark with distilled water. The solution is polarographed at 25 ° C. A solution of 4-aminophenol having a concentration of c (4-aminophenol) = 1 · 10 J mol / l gives a current of 6.6 under experimental conditions. 10 “-A.
Pro výpočet obsahu 4-aminofenolu platí vztah:The following applies to the calculation of the 4-aminophenol content:
fx . 25 . 100 % hm· af x . 25. 100% wt
- 3 224 568 kde f^ jsou gramy 4-aminof enolu, odpovídající výšce vlny 1 mm a je navážka heterogenní reakční směsi v gramech.Where β are the grams of 4-aminophenol corresponding to a wave height of 1 mm and the weight of the heterogeneous reaction mixture is in grams.
Stanovení 4-N-ac ety laminofenolu.Determination of 4-N-ac ethylaminophenol.
Obsah roztoku druhé odměrné baňky se zalkalizuje roztokem hydroxidu sodného o koncentraci c (NaOH) = 2 mol/1 na pH > 14·The solution of the second volumetric flask is made alkaline with a sodium hydroxide solution of c (NaOH) = 2 mol / l to a pH> 14 ·
Po cca 1 hodině, kdy je splněn předpoklad kvantitativního rozkladu diaza 4-aminofenolu, se roztok opatrně zneutralizuje koncentrovanou kyselinou chlorovodíkovou na pH cca 6 až 7, přidá se 1 ml 1% hm· Syntegalu V-7, 15 ml roztoku chlorid amonný - amoniak o koncentraci o (NH^Cl) = 1 mol/1 a c (NH^OH) = 1 mol/1 a doplní se po značku destilovanou vodou. Polarografuje se za stejných podmínek jako je uvedeno shora.After about 1 hour, when the quantitative decomposition of the diaza 4-aminophenol is met, the solution is carefully neutralized with concentrated hydrochloric acid to a pH of about 6 to 7, 1 ml of 1 wt.% Syntegal V-7, 15 ml of ammonium chloride-ammonia solution are added. Concentration o (NH 4 Cl) = 1 mol / l and c (NH 4 OH) = 1 mol / l and make up to the mark with distilled water. Polarograph under the same conditions as above.
Roztok 4-N-acetylaminofenolu o koncentraci o (4-N-aoetylaminofenol) « 1 · 10“^ mol/1 poskytuje za experimentálních podmínek proud 6,6 . 10“^a,A solution of 4-N-acetylaminophenol having a concentration of o (4-N-aethylaminophenol) of < 1 · 10 < 10 > 10 “^ a ,
Pro výpočet obsahu 4-N-acetylaminofenolu platí vztah:The following applies to the calculation of the 4-N-acetylaminophenol content:
. 25 . 100 % hm. a —6---— a. 25. 100% wt. and —6 ---— and
kde fg jsou gramy 4-N-acetylaminofenolu odpovídající výšce vlny 1 mm .where fg are grams of 4-N-acetylaminophenol corresponding to a wave height of 1 mm.
a je navážka heterogenní reakční směsi v gramech.and is the weight of the heterogeneous reaction mixture in grams.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88481A CS224568B1 (en) | 1981-02-06 | 1981-02-06 | Method for polarographic determination 4-n-acetylaminphenol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88481A CS224568B1 (en) | 1981-02-06 | 1981-02-06 | Method for polarographic determination 4-n-acetylaminphenol |
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| CS224568B1 true CS224568B1 (en) | 1984-01-16 |
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| CS88481A CS224568B1 (en) | 1981-02-06 | 1981-02-06 | Method for polarographic determination 4-n-acetylaminphenol |
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1981
- 1981-02-06 CS CS88481A patent/CS224568B1/en unknown
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