Síntesis y caracterización de dos materiales azo: Comparación  entre un compuesto sulfonado y su análogo no sulfonado

Byron Lopez Mayorga; Edward M. A. Guerrero-Gutiérrez; Allan Vásquez-Bolaños; José Castillo-Arroyave; Heriberto Pfeiffer

doi:10.36829/63CTS.v11i1.1596

Autores/as

Byron Lopez Mayorga Universidad de San Carlos de Guatemala https://orcid.org/0000-0001-7165-6283
Edward M. A. Guerrero-Gutiérrez Escuela de Ingeniería Química, Facultad de Ingeniería, Universidad de San Carlos de Guatemala https://orcid.org/0000-0002-5778-3953
Allan Vásquez-Bolaños Escuela de Química
José Castillo-Arroyave Escuela de Química, Facultad de Ciencias Químicas y Farmacia, Universidad de San Carlos de Guatemala
Heriberto Pfeiffer https://orcid.org/0000-0002-6623-5780

DOI:

https://doi.org/10.36829/63CTS.v11i1.1596

Palabras clave:

Grupo sulfónico, histéresis, compuesto azo, degradación térmica

Resumen

Esta investigación tuvo como objetivo la síntesis y caracterización de dos nuevos materiales azo obtenidos mediante una reacción clásica de diazotización. El primer material (A1) se sintetizó a partir de la reacción entre fluoroglucinol con p-fenilendiamina, mientras que el segundo (A2) se obtuvo a partir de la reacción entre fluoroglucinol con ácido 2,5-diaminobencensulfónico. Estos materiales fueron caracterizados químicamente mediante espectroscopia infrarroja (FTIR-ATR). Adicionalmente, se evaluó su estabilidad térmica por medio análisis termogravimétrico (TGA) y su estructura cristalina, utilizando difracción de rayos X de polvos (XRD). Los resultados muestran que A2 posee una mayor capacidad de absorción de agua atribuible a los grupos sulfónicos. Además, ambos materiales empiezan a degradarse a partir de los 140 °C y son de naturaleza amorfa, conun área de superficie menor a 1 m²g^-1. Destaca que A2 posee hasta un orden de magnitud mayor que A1 para la absorción de N₂. Ambos materiales mostraron características de adsorción de nitrógeno de isoterma tipo III, lo que sugiere bajas energías de interacción y propiedades de materiales no porosos.

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Ansari, M., Alam, A., Bera, R., Hassan, A., Goswami, S., & Das, N. (2020). Synthesis, characterization and adsorption studies of a novel triptycene based hydroxyl azo- nanoporous polymer for environmental remediation. Journal of Environmental Chemical Engineering, 8(2), Artículo 103558. https://doi.org/10.1016/j.jece.2019.103558

Avilés-Barreto, S. L., & Suleiman, D. (2013). Transport properties of sulfonated poly (styrene-isobutylene-styrene) membranes with counter-ion substitution. Journal of Applied Polymer Science, 129(4), 2294-2304. https://doi.org/10.1002/app.38952

Awad, A. M., Jalab, R., Benamor, A., Nasser, M. S., Ba-Abbad, M. M., El-Naas, M., & Mohammad, A. W. (2020). Adsorption of organic pollutants by nanomaterial-based adsorbents: An overview. Journal of Molecular Liquids, 301, Artículo 112335. https://doi.org/10.1016/j.molliq.2019.112335

Braun, D. E., Tocher, D. A., Price, S. L., & Griesser, U. J. (2012). The Complexity of Hydration of Phloroglucinol: A Comprehensive Structural and Thermodynamic Characterization. The Journal of Physical Chemistry B, 116(13), 3961-3972. https://doi.org/10.1021/jp211948q

Dong, S., Rene, E. R., Zhao, L., Xiaoxiu, L., & Ma, W. (2022). Design and preparation of functional azo linked polymers for the adsorptive removal of bisphenol A from water: Performance and analysis of the mechanism. Environmental Research, 206, 112601. https://doi.org/10.1016/j.envres.2021.112601

Fröschl, T., Hörmann, U., Kubiak, P., Kučerová, G., Pfanzelt, M., Weiss, C. K., Behm, R. J., Hüsing, N., Kaiser, U., Landfester, K., & Wohlfahrt-Mehrens, M. (2012). High surface area crystalline titanium dioxide: Potential and limits in electrochemical energy storage and catalysis. Chemical Society Reviews, 41(15), 5313-5360. https://doi.org/10.1039/C2CS35013K

Guerrero-Gutiérrez, E. M. A. (2021). Effect of Sulfonated Block Copolymer on the Equilibrium and Thermal Properties of Sulfonated Fluoro-block Copolymer Blend Membranes. Ciencia, Tecnología y Salud, 8(1), 57-66. https://doi.org/10.36829/63CTS.v8i1.887

Guerrero-Gutiérrez, E. M. A., Abad, M., Gaitán, I., & Guerrero, K. (2022). Efecto de las membranas con Cu+2 sobre el proceso de filtración y capacidad de biocida contra Escherichia coli. Ciencia, Tecnología y Salud, 9(1), 98-115. https://doi.org/10.36829/63CTS.v9i1.1041

Ho, M. S., Barrett, C., Paterson, J., Esteghamatian, M., Natansohn, A., & Rochon, P. (1996). Synthesis and Optical Properties of Poly{(4-nitrophenyl)[3-[N-[2-(methacryloyloxy)ethyl]-carbazolyl]] diazene}. Macromolecules, 29(13), 4613-4618. https://doi.org/10.1021/ma951432a

Huang, X.-Q., Hong, X., Lin, H., Cao, X.-M., Dang, Q., Tang, S.-B., Chen, D.-L., & Zhang, Y. (2022). Hypercrosslinked triazine-phloroglucinol hierarchical porous polymers for the effective removal of organic micropollutants. Chemical Engineering Journal, 435(Part 2), Artículo 134990. https://doi.org/10.1016/j.cej.2022.134990

Hung, L.-C., & Pan, N.-H. (2023). Using thermal analysis with kinetic calculation method to assess the thermal stability of azo compound on construction materials. Journal of Loss Prevention in the Process Industries, 84, Artículo 105107. https://doi.org/10.1016/j.jlp.2023.105107

Kazem-Rostami, M. (2020). Factors influencing the thermal stability of azo and bisazo compounds. Journal of Thermal Analysis and Calorimetry, 140(2), 613-623. https://doi.org/10.1007/s10973-019-08884-4

Kim, D.-J., & Nam, S.-Y. (2014). Characterization of Sulfonated Silica Nanocomposite Electrolyte Membranes for Fuel Cell. Journal of Nanoscience and Nanotechnology, 14(12), 8961-8963. https://doi.org/10.1166/jnn.2014.10073

Li, H.-Q., Liu, X., Zhang, Q., Li, S.-S., Liu, Y.-M., He, H.-Y., & Cao, Y. (2015). Deoxygenative coupling of nitroarenes for the synthesis of aromatic azo compounds with CO using supported gold catalysts. Chemical Communications, 51(56), 11217-11220. https://doi.org/10.1039/C5CC03134F

Li, Y., Xie, M., Wang, X., Chao, D., Liu, X., & Wang, X. (2013). Novel branched sulfonated poly(ether ether ketone) membranes for direct methanol fuel cells. International Journal of Hydrogen Energy, 38, 12051-12059. https://doi.org/10.1016/j.ijhydene.2013.06.090

López-Pardo, G. E. A., García-Guerra, C. A., Lainfiesta, R., & Guerrero-Gutiérrez, E. M. A. (2022). Caracterización colorimétrica del proceso termogravimétrico de la deshidroxilación de caolín hidrotermal y de toba. Ciencia, Tecnología y Salud, 9(1), 55-69. https://doi.org/10.36829/63CTS.v9i1.924

Lorenzo, M., Campo, J., & Picó, Y. (2018). Analytical challenges to determine emerging persistent organic pollutants in aquatic ecosystems. TrAC Trends in Analytical Chemistry, 103, 137-155. https://doi.org/10.1016/j.trac.2018.04.003

Lu, J., & Zhang, J. (2014). Facile synthesis of azo-linked porous organic frameworks via reductive homocoupling for selective CO2 capture. Journal of Materials Chemistry A, 2(34), 13831-13834. https://doi.org/10.1039/C4TA03015J

Luo, X.-S., Deng, H.-L., Chi, S., Liu, Y., & Huang, M.-H. (2021). 15N Solid-State NMR as Bright Eyes to See the Isomerization of the Azo Bond: Revision of Tris(β-hydroxyl-azo)benzene to Tris(β-keto-hydrazo)-cyclohexane in Porous Organic Polymers. The Journal of Physical Chemistry Letters, 12(29), 6767-6772. https://doi.org/10.1021/acs.jpclett.1c01750

Mandal, J., Jia, M., Overvig, A., Fu, Y., Che, E., Yu, N., & Yang, Y. (2019). Porous Polymers with Switchable Optical Transmittance for Optical and Thermal Regulation. Joule, 3(12), 3088-3099. https://doi.org/10.1016/j.joule.2019.09.016

Meyers, M. A., Mishra, A., & Benson, D. J. (2006). Mechanical properties of nanocrystalline materials. Progress in Materials Science, 51(4), 427-556. https://doi.org/10.1016/j.pmatsci.2005.08.003

Murad, A. R., Iraqi, A., Aziz, S. B., N. Abdullah, S., & Brza, M. A. (2020). Conducting polymers for optoelectronic devices and organic solar cells: A review. Polymers, 12(11), Artículo 2627. https://doi.org/10.3390/polym12112627

Peplowski, L., Szczesny, R., Skowronski, L., Krupka, A., Smokal, V., & Derkowska-Zielinska, B. (2022). Vibrational spectroscopy studies of methacrylic polymers containing heterocyclic azo dyes. Vibrational Spectroscopy, 120, Artículo 103377. https://doi.org/10.1016/j.vibspec.2022.103377

Pomonis, P. J., Petrakis, D. E., Ladavos, A. K., Kolonia, K. M., Armatas, G. S., Sklari, S. D., Dragani, P. C., Zarlaha, A., Stathopoulos, V. N., & Sdoukos, A. T. (2004). A novel method for estimating the C-values of the BET equation in the whole range. Microporous and Mesoporous Materials, 69(1), 97-107. https://doi.org/10.1016/j.micromeso.2004.01.009

Sánchez-Jiménez, P. E., Pérez-Maqueda, L. A., Perejón, A., & Criado, J. M. (2009). Combined kinetic analysis of thermal degradation of polymeric materials under any thermal pathway. Polymer Degradation and Stability, 94(11), 2079-2085. https://doi.org/10.1016/j.polymdegradstab.2009.07.006

Sava, I., Burescu, A., Stoica, I., Musteata, V., Cristea, M., Mihaila, I., Pohoata, V., & Topala, I. (2015). Properties of some azo-copolyimide thin films used in the formation of photoinduced surface relief gratings. RSC Advances, 5(14), 10125-10133. https://doi.org/10.1039/C4RA14218G

Sava, I., Hurduc, N., Sacarescu, L., Apostol, I., & Damian, V. (2013). Study of the nanostructuration capacity of some azopolymers with rigid or flexible chains. High Performance Polymers, 25(1), 13-24. https://doi.org/10.1177/0954008312454151

Selivanova, G. A. (2021). Azo chromophores for nonlinear-optical application. Russian Chemical Bulletin, 70(2), 213-238. https://doi.org/10.1007/s11172-021-3080-z

Shen, Y., Ni, W.-X., & Li, B. (2021). Porous Organic Polymer Synthesized by Green Diazo-Coupling Reaction for Adsorptive Removal of Methylene Blue. ACS Omega, 6(4), 3202-3208. https://doi.org/10.1021/acsomega.0c05634

Si, Y., & Samulski, E. T. (2008). Synthesis of Water Soluble Graphene. Nano Letters, 8(6), 1679-1682. https://doi.org/10.1021/nl080604h

Tajik, S., Beitollahi, H., Nejad, F. G., Dourandish, Z., Khalilzadeh, M. A., Jang, H. W., Venditti, R. A., Varma, R. S., & Shokouhimehr, M. (2021). Recent Developments in Polymer Nanocomposite-Based Electrochemical Sensors for Detecting Environmental Pollutants. Industrial & Engineering Chemistry Research, 60(3), 1112-1136. https://doi.org/10.1021/acs.iecr.0c04952

Thommes, M., Kaneko, K., Neimark, A. V., Olivier, J. P., Rodriguez-Reinoso, F., Rouquerol, J., & Sing, K. S. W. (2015). Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution (IUPAC Technical Report). Pure and Applied Chemistry, 87(9-10), 1051-1069. https://doi.org/10.1515/pac-2014-1117

Trivedi, M. K., Branton, A., Trivedi, D., Nayak, G., Singh, R., & Jana, S. (2015). Characterization of physical, thermal and spectroscopic properties of Biofield Energy Treated p-Phenylenediamine and p-Toluidine. Environmental & Analytical Toxicology, 5(6), Artículo 1000329. https://doi.org/10.4172/2161-0525.1000329

Wang, J., He, J., Zhi, C., Luo, B., Li, X., Pan, Y., Cao, X., & Gu, H. (2014). Highly efficient synthesis of azos catalyzed by the common metal copper (0) through oxidative coupling reactions. RSC Advances, 4(32), 16607-16611. https://doi.org/10.1039/C4RA00749B

Wang, Z., He, M., Chen, B., & Hu, B. (2020). Azo-linked porous organic polymers/polydimethylsiloxane coated stir bar for extraction of benzotriazole ultraviolet absorbers from environmental water and soil samples followed by high performance liquid chromatography-diode array detection. Journal of Chromatography A, 1616, Artículo 460793. https://doi.org/10.1016/j.chroma.2019.460793

Wongsa, P., Phatikulrungsun, P., & Prathumthong, S. (2022). FT-IR characteristics, phenolic profiles and inhibitory potential against digestive enzymes of 25 herbal infusions. Scientific Reports, 12(1), Artículo 6631. https://doi.org/10.1038/s41598-022-10669-z

Zhang, T., Bai, R., Shen, J., Wang, Q., Wang, P., Yuan, J., & Fan, X. (2018). Laccase-catalyzed polymerization of diaminobenzenesulfonic acid for pH-responsive color-changing and conductive wool fabrics. Textile Research Journal, 88(19), 2258-2266. https://doi.org/10.1177/0040517517720497

Zhang, Y., Hong, X., Cao, X.-M., Huang, X.-Q., Hu, B., Ding, S.-Y., & Lin, H. (2021). Functional Porous Organic Polymers with Conjugated Triaryl Triazine as the Core for Superfast Adsorption Removal of Organic Dyes. ACS Applied Materials & Interfaces, 13(5), 6359-6366. https://doi.org/10.1021/acsami.0c21374

Zhang, Y., & Riduan, S. N. (2012). Functional porous organic polymers for heterogeneous catalysis. Chemical Society Reviews, 41(6), 2083-2094. https://doi.org/10.1039/C1CS15227K

Zhao, G., Huang, X., Tang, Z., Huang, Q., Niu, F., & Wang, X. (2018). Polymer-based nanocomposites for heavy metal ions removal from aqueous solution: A review. Polymer Chemistry, 9(26), 3562-3582. https://doi.org/10.1039/C8PY00484F

Zhao, J., Yan, G., Zhang, X., Feng, Y., Li, N., Shi, J., & Qu, X. (2022). In situ interfacial polymerization of lithiophilic COF@PP and POP@PP separators with lower shuttle effect and higher ion transport for high-performance Li–S batteries. Chemical Engineering Journal, 442, Artículo 136352. https://doi.org/10.1016/j.cej.2022.136352

Zhou, W., Yoshino, M., Kita, H., & Okamoto, K. (2001). Carbon Molecular Sieve Membranes Derived from Phenolic Resin with a Pendant Sulfonic Acid Group. Industrial & Engineering Chemistry Research, 40(22), 4801-4807. https://doi.org/10.1021/ie010402v