Synthesis and Characterization of New Azo Dye Derived from Sulfamethaxolevia Diazonium Reaction and Study its Abilityas an Acid-base Indicator

Authors

DOI:

https://doi.org/10.23851/mjs.v35i2.1375

Keywords:

Sulfamethoxazole, 4-methoxy phenol, Indicator, Azo dye, acid-base indicator

Abstract

Background: Most azo dyes are synthesized by diazotization of a primary amine, followed by conjugation with one or more electron-rich nucleophiles. Objective: This study presents the synthesis of a new azocompound by converting sulfamethoxazole to a diazonium salt. Methods: via reaction with hydrochloric acid and sodium nitrite at temperatures between 0 and 5 °C, the resulting salt is then coupled with a 4-methoxyphenol reagent in alkaline medium at the above temperatures to produce an azodye given the IUPAC name of (4-((2-hydroxy-5-methoxyphenyl)diazenyl)-N-(5-methylisoxazol-3yl)benzenesulfonamide). The azo dye precipitate was purified by crystallization methods using a solvent mixture of ethanol water. Characterization was done using different analytical methods such as IR, UV-Vis and H1-NMR in addition to measurements of physical properties. Results: The reddish-pink azo compound gave a maximum absorbance of 495 nm. Acid-base titrimetric analysis was conducted to examine the chemical indicator properties of the azo dye. Clear color differences were obtained between two spaces in the pH range 2-12, where a reddishpink color was obtained in the basic medium and a yellow color in the acidic medium. Conclusions: A new azo dye successfully presented its properties as an indicator.

Downloads

Download data is not yet available.

References

Mohammed, S. A., Al-Hamdany, N. M., &Abdulkader, A. N.,"Spectrophotometric determination of sulfamethoxazole in pure and in pharmaceutical preparations by diazotization and coupling reaction" Rafidain Journal of Science, 28(3), 15-26, 2018.

CrossRef

Le, T. H., Lee, H. J., Kim, J. H., & Park, S. J., "Highly selective fluorescence sensor based on graphene quantum dots for sulfamethoxazole determination" Materials, 13(11), 2521, 2020.

CrossRef | PubMed

Ayejuyo, O. O., Courage, N., Hamed, M. O., &Oladipo, O. J., "liquid chromatographic technique for the simultaneous determination of sulphamethoxazole and trimethoprim in pharmaceutical formulations", unilag Journal of Medicine Science and Technology, 4(2), 120-132, 2020.

Wan, J., Jin, C., Liu, B., She, Z., Gao, M., & Wang, Z., "Electrochemical oxidation of sulfamethoxazole using Ti/SnO2-Sb/Co-PbO2 electrode through ANN-PSO" , Journal of the Serbian Chemical Society, 84(7), 713-727, 2019.

CrossRef

Dimpe, K. M., Mpupa, A., &Nomngongo, P. N.,"Microwave assisted solid phase extraction for separation preconcentrationsulfamethoxazole in wastewater using tyre based activated carbon as solid phase material prior to spectrophotometric determination" ,SpectrochimicaActa Part A: Molecular and Biomolecular Spectroscopy, 188, 341-348, 2018.‏

CrossRef | PubMed

Abood, N. K., &Hassana, M. J. M., "Spectrophotometric Determination of Sulfadoxine Drug use Cloud point and Flow injection Methods in Pharmaceutical Formulations", Egyptian Journal of Chemistry, 64(6), 2913-2924, 2021.

Wan, H., Li, C., Mahmud, S., & Liu, H., "Kappa carrageenan reduced-stabilized colloidal silver nanoparticles for the degradation of toxic azo compound", Colloids and Surfaces A: Physicochemical and Engineering Aspects, 616, 126325, 2021.

CrossRef

Maliyappa, M. R., Keshavayya, J., Mahanthappa, M., Shivaraj, Y., &Basavarajappa, K. V.,"6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: synthesis, characterization, electrochemical and DFT studies", Journal of Molecular Structure, 1199, 126959,2020.

CrossRef

Roopa, K. P., &Jayanna, B. K.,"Spectrophotometric determination of some cephalosporins in bulk and in pharmaceutical formulations", Analytical Chemistry Letters, 6(2), 143-152, 2016.

CrossRef

Benkhaya, S., M'rabet, S., & El Harfi, A.,"Classifications, properties, recent synthesis and applications ofazo dyes", Heliyon, 6(1), e03271, 2020.

CrossRef | PubMed

Hassan, M. J. M., & Al-Rubaiawi, M. S. F., "Cloud point extraction spectrophotometric method for determination of three types of cephalosporin via diazotization reactions with different reagents", Br. J. Anal chem, 4(17), 2017.

Kahlert, H., Meyer, G., & Albrecht, A.,"Colour maps of acid-base titrations with colour indicators: how to choose the appropriate indicator and how to estimate the systematic titration errors", ChemTexts, 2, 1-28, 2016.

CrossRef

Raghavendra, N., Hublikar, L. V., R Chitnis, S., A Joseph, R., S Sheelimath, D., & S Pattan, P., "Areca catechu seed extract as improvised acid-base indicator in titrimetric Analysis: An environmental benign approach", Journal of Water and Environmental Nanotechnology, 5(2), 129-138, 2020.

Vogler, N., Lindemann, M., Drabetzki, P., &Kühne, H. C., "Alternative pH-indicators for determination of carbonation depth on cement-based concretes:, Cement and Concrete Composites, 109, 103565, 2020.

CrossRef

Hua, X. W., Bao, Y. W., & Wu, F. G., "Fluorescent carbon quantum dots with intrinsic nucleolus-targeting capability for nucleolus imaging and enhanced cytosolic and nuclear drug delivery", ACS applied materials &interfaces, 10(13), 10664-10677, 2018.

CrossRef | PubMed

Leshe, S., &Baye, H.,"Extraction of Green Acid-Base Indicators From Acanthus Pubescens Flower for Use in the School Laboratory", International Journal of Chemistry, 12(2), 35-44, 2020.

CrossRef

O. OLANREWAJU and N. O ADEOSUN, "Application of principles and tools in green chemistry to education using rose flower extract as Acid-Base indicator", J. Chem. Soc. Nigeria, Vol. 48, No. 1, pp 045 - 050, 2023.

CrossRef

MussaratJabeen, Kainat Tariq, AtiyaRehman, Syed UbaidHussain, Ansa M. Zafar," Evaluation of Improvised and Eco-Friendly Natural pH-Paper Indicators", Frontiers In Chemical Sciences, 3(2):22-31, 2022.

CrossRef

Tao, C. P., Jiang, C. C., Wang, Y. H., Zheng, J. F., Shao, Y., & Zhou, X. S., " Single-molecule sensing of interfacial acid-base chemistry", The Journal of Physical Chemistry Letters, 11(23), 10023-10028, 2020.

CrossRef | PubMed

GeneviveChinyereOnuegbu, OnyekachiOnyinyechiNnorom, Gerald OkwuchiOnyedika, "Comparative Study on the Acid-Base Indicator Properties of Natural Dye, Turmeric Rhizome (Curcuma longa) and Synthetic Dyes", Journal of Textile Science and Technology, 9, 20-29, 2023.

CrossRef

Sager, M. A. J. A. G., "Preparation and Characterization of Two Azo Dyes ForDibenzothiophen by The Diazotization Reaction and Studying Their action as Acid-Base Indicators", Journal of university of Anbar for Pure science, 7(2), 2013.

CrossRef

Al-Jorani, K. R., Abbas, R. F., &Waheb, A. A., "Synthesis and characterization of a novel benzimidazole derivative: Solvatochromic and acid-base indicator applications", Materials Today: Proceedings, 42, 1791-1799, 2021.‏

CrossRef

Yang, J., Xu, X., Yang, Y., Rui, J., Zhang, Y., Kuang, H., ...& Wu, L., "Synthesis, optical properties, and acid-base indicating performance of novel ketene hydroxybenzylidenenopinone derivatives", RSC advances, 6(113), 111760-111766, 2016.

CrossRef

Downloads

Key Dates

Received

17-04-2023

Revised

20-07-2023

Accepted

04-08-2023

Published

30-06-2024

Data Availability Statement

Data is available in the article.

Issue

Section

Original Article

How to Cite

[1]
M. S. . Falih, N. I. . Mahdi, A. A. wahid . Jasim, R. F. Abbas, and A. A. A. A. . Rahi, “Synthesis and Characterization of New Azo Dye Derived from Sulfamethaxolevia Diazonium Reaction and Study its Abilityas an Acid-base Indicator”, Al-Mustansiriyah J. Sci., vol. 35, no. 2, pp. 1–8, Jun. 2024, doi: 10.23851/mjs.v35i2.1375.

Similar Articles

1-10 of 199

You may also start an advanced similarity search for this article.