Green synthesis of UV absorber (E)-2-(((4-(benzyloxy)phenyl)imino)methyl)phenol by microwave method

Authors

  • Kieu-Khanh Nguyen Thi Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • Anh-Thu Nguyen Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • Anh - Vu Ho Pham Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • Viet-Hai Le Faculty of Materials Science and Technology, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • Ngoc-An Nguyen Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • Thanh-Nguyen Huynh Le Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • Thanh-Thien Co Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • Hoang-Thai Nguyen Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam
  • That-Quang Ton Faculty of Chemistry, University of Science (UoS), Vietnam National University Ho Chi Minh City (VNU-HCM), 227 Nguyen Van Cu, District 5, HoChiMinh City, Vietnam

DOI:

https://doi.org/10.56764/hpu2.jos.2023.2.2.59-67

Abstract

In this work, a UV absorber compound (E)-2-(((4-(benzyloxy)phenyl)imino)methyl)phenol was synthesized by microwave method using a two steps protocol. In the first step, α-(4-hydroxyphenylimino)-o-cresol (1) was synthesized from 4-aminophenol and salicylaldehyde by circulating under microwave heating at 60 oC for 8 minutes, the reaction yield reached 82.91 %. In the second step (E)-2-(((4-(benzyloxy)phenyl)imino)methyl)phenol (2) was synthesized from precursor (1) and benzyl bromide by circulating under microwave heating at 80 oC for 3 minutes, the reaction yield reached 25.08 %. The overall yield for the synthesis of UV absorber 2 was 20.79 %. The molecular structures of precursor (1) and product (2) were analysed by high performance liquid chromatography - mass spectrometry (LC/MS) and nuclear magnetic resonance (NMR) methods. The UV absorbance of precursor (1) and product (2) was investigated by UV absorption spectrometry. The obtained results show that product (2) has a higher UV absorption intensity than precursor (1), the UV absorption region extends from 240 nm to 390 nm, the maximum absorption peak is at the wavelength (λmax) of 350 nm. The UV absorber (E)-2-(((4-(benzyloxy)phenyl)imino)methyl)phenol with cyclic structure, low molecular weight, and high UV absorbance has potential application as an UV absorber for greenhouse covering plastic, paint and ink systems.

References

. Jafferson J.M., Chatterjee D. (2021), “A review on polymeric materials in additive manufacturing”, Mater. Today: Proc. 46(2):1349-65. https://doi.org/10.1016/j.matpr.2021.02.485.

. Guillet, J. E. (1972), "Fundamental processes in the U.V. degradation and stabilization of polymers", Pure Appl. Chem., 30(1-2): 35- 44. https://doi.org/10.1351/pac197230010135.

. Peterson, J.D., Vyazovkin, S. and Wight, C.A. (2001), "Kinetics of the Thermal and Thermo-Oxidative Degradation of Polystyrene, Polyethylene and Poly(propylene)", Macromol. Chem. Phys., 202: 775-84. https://onlinelibrary.wiley.com/doi/10.1002/1521-3935(20010301)202:6%3C775::AID-MACP775%3E3.0.CO;2-G.

. Pospisil J., Nespurek S. (2000), "Photostabilization of coatings Mechanisms and performance", Prog. Polym. Sci., 25, 1261-335. https://doi.org/10.1016/S0079-6700(00)00029-0

. Pfaendner, R., Herbst, H., Hoffmann, K. and Sitek, F. (1995), "Recycling and restabilization of polymers for high quality applications. An Overview", Angew. Makromol. Chem., 232: 193-227. https://doi.org/10.1002/apmc.1995.052320113.

. Pavanello A., Gomez-Mendoza M., Víctor A. de la Peña O'Shea, Miguel A. Miranda, M. Marin L. (2022), “Degradation of Benzotriazole UV-stabilizers in the presence of organic photosensitizers and visible light: A time-resolved mechanistic study”, J. Photochem. Photobiol. B, Biol., 230: 112444. https://doi.org/10.1016/j.jphotobiol.2022.112444.

. Yousif, E., Bakir, E., Salimon J., Salih, N. (2012), "Evaluation of Schiff bases of 2,5-dimercapto-1,3,4-thiadiazole as photostabilizer for poly(methyl methacrylate) ", J. Saudi Chem. Soc., 16, 279–285. https://doi.org/ 10.1016/j.jscs.2011.01.009.

. Ocal,N., Aker, A., Ergindemir, H. N. and Hamitbeyli, A. (2016), "Synthesis of novel heterocyclic imine type UV absorbers for

application on cotton based textile materials", J. Chem., Volume 2016, Article ID 6387305, 6 pages http://dx.doi.org/10.1155/2016/6387305.

. Yousif, E., Salimon, J., Salih, N. (2012), "New stabilizers for polystyrene based on 2-N-salicylidene-5- (substituted)-1,3,4-thiadiazole compounds", J. Saudi Chem. Soc., 16, 299-306. http://dx.doi.org/10.1016/j.jscs.2011.01.011.

. Shen, Y., Zhen, L., Huang, D., Xue, J. (2014), "Improving anti-UV performances of cotton fabrics via graft modification using a reactive UV-absorber", Cellulose, 21, 3745–3754, http://dx.doi.org/ 10.1007/s10570-014-0367-3.

. Soley, M.B., Videla, P.E., Nibbering, E.T.J., and Batista, V. S. (2022), "Ultrafast Charge Relocation Dynamics in Enol−Keto Tautomerization Monitored with a Local Soft-X-ray Probe” J. Phys. Chem. Lett., 13, 8254−8263. https://doi.org/10.1021/acs.jpclett.2c02037.

. Joshi, H.C., and Antonov L. (2021), "Excited-State Intramolecular Proton Transfer: A Short Introductory Review”, Molecules, 26, 1475. https://doi.org/10.3390/molecules26051475.

Published

31-08-2023

How to Cite

Nguyen Thi, K.-K., Nguyen, A.-T., Ho Pham, A. .-. V., Le, V.-H., Nguyen, N.-A., Huynh Le, T.-N., Co, T.-T., Nguyen, H.-T., & Ton, T.-Q. (2023). Green synthesis of UV absorber (E)-2-(((4-(benzyloxy)phenyl)imino)methyl)phenol by microwave method. HPU2 Journal of Science: Natural Sciences and Technology, 2(2), 59–67. https://doi.org/10.56764/hpu2.jos.2023.2.2.59-67

Volume and Issue

Section

Natural Sciences and Technology