Mild Synthesis, Characterization, and Application of some Polythioester Polymers Catalyzed by Cetrimide Ionic Liquid as a Green and Eco-Friendly Phase-Transfer Catalyst
محورهای موضوعی : Iranian Journal of Catalysis
Azhar Ali
1
(Directorate of Education in Nineveh, Mosul, Iraq)
Mohanad Saleh
2
(Department of Chemistry, College of Education for pure science, University of Mosul, Mosul, Iraq)
Khalid Owaid
3
(Department of Chemistry, College of Education for pure science, University of Mosul, Mosul, Iraq)
کلید واژه: polymer, Phase transfer catalyst, Ionic liquid, Bone cement, polythioesters, cetrimide,
چکیده مقاله :
In this research, we develop and prepare some of the polymers based on polythioesters using cetrimide as an ionic liquid and phase transfer catalyst. All of the polymers were prepared through the reaction of 5,5'-methylenebis (1,3,4-oxadiazole-2-thiol) with five types of diacyl chloride derivatives in the presence of cetrimide as phase transfer catalyst in the mixture of water and chloroform at room temperature. The chemical structure of synthesized polymers was determined using 1H NMR and 13C NMR spectroscopy. The mechanical and thermal stability of the synthesized polymers were investigated. In addition, using DFT calculation, the chemical optimization of synthesized polymers was presented. Moreover, the catalytic activity of cetrimide was compared with four types of ionic liquid with phase transfer catalyst roles. Additionally, the application of synthesized polymers in bone cement was investigated.
[1] M. Wang, X. Jiang, Sulfur–sulfur bond construction, Sulfur Chemistry, (2019) 285-324.
[2] C. Liu, B. Wang, Z. Guo, J. Zhang, M. Xie, Metal-free cascade rearrangement/radical addition/oxidative C–H annulation of propargyl alcohols with sodium sulfinates: access to 2-sulfenylindenones, Organic Chemistry Frontiers, 6 (2019) 2796-2800.
[3] D. Cao, P. Pan, C.-J. Li, H. Zeng, Photo-induced transition-metal and photosensitizer free cross–coupling of aryl halides with disulfides, Green Synthesis and Catalysis, 2 (2021) 303-306.
[4] X. Cao, H. Wang, J. Yang, R. Wang, X. Hong, X. Zhang, J. Xu, H. Wang, Sulfur-substitution-enhanced crystallization and crystal structure of poly (trimethylene monothiocarbonate), Chin. Chem. Lett., 33 (2022) 1021-1024.
[5] C.G. Kim, M.J. Son, J.Y. Do, Cationic living polymerization of cyclic dithiocarbonates involving sulfide-migration, Eur. Polym. J., 156 (2021) 110611.
[6] J.Y. Do, S.B. Shin, S.M. Jeong, M.-y. Jung, Ring-opening polymerization of cyclic 1, 3-oxathiolane-2-thione promoted by neighboring sulfide group and ring contraction, Eur. Polym. J., 131 (2020) 109689.
[7] Y. Zhang, K.M. Konopka, R.S. Glass, K. Char, J. Pyun, Chalcogenide hybrid inorganic/organic polymers (CHIPs) via inverse vulcanization and dynamic covalent polymerizations, Polymer Chemistry, 8 (2017) 5167-5173.
[8] Y. Zhang, T.S. Kleine, K.J. Carothers, D.D. Phan, R.S. Glass, M.E. Mackay, K. Char, J. Pyun, Functionalized chalcogenide hybrid inorganic/organic polymers (CHIPs) via inverse vulcanization of elemental sulfur and vinylanilines, Polymer Chemistry, 9 (2018) 2290-2294.
[9] A. Kausar, S. Zulfiqar, M.I. Sarwar, Recent developments in sulfur-containing polymers, Polymer Reviews, 54 (2014) 185-267.
[10] L.V.S. Ceneviva, M. Mierzati, Y. Miyahara, C.T. Nomura, S. Taguchi, H. Abe, T. Tsuge, Poly (3-mercapto-2-methylpropionate), a Novel α-Methylated Bio-Polythioester with Rubber-like Elasticity, and Its Copolymer with 3-hydroxybutyrate: Biosynthesis and Characterization, Bioengineering, 9 (2022) 228.
[11] S.M. Guillaume, Sustainable and degradable plastics, Nat. Chem., 14 (2022) 245-246.
[12] X.-L. Chen, B. Wang, D.-P. Song, L. Pan, Y.-S. Li, One-Step Synthesis of Sequence-Controlled Polyester-block-Poly (ester-alt-thioester) by Chemoselective Multicomponent Polymerization, Macromolecules, 55 (2022) 1153-1164.
[13] M. Shin, H. Kim, G. Park, J. Park, H. Ahn, D.K. Yoon, E. Lee, M. Seo, Bilayer-folded lamellar mesophase induced by random polymer sequence, Nature communications, 13 (2022) 1-8.
[14] M. Frenkel-Pinter, M. Bouza, F.M. Fernández, L.J. Leman, L.D. Williams, N.V. Hud, A. Guzman-Martinez, Thioesters provide a plausible prebiotic path to proto-peptides, Nature communications, 13 (2022) 1-8.
[15] V.D. Nguyen, R. Trevino, S.G. Greco, H.D. Arman, O.V. Larionov, Tricomponent Decarboxysulfonylative Cross-coupling Facilitates Direct Construction of Aryl Sulfones and Reveals a Mechanistic Dualism in the Acridine/Copper Photocatalytic System, ACS Catal., 12 (2022) 8729-8739.
[16] C.S. Marvel, A. Kotch, Polythiolesters, J. Am. Chem. Soc., 73 (1951) 1100-1102.
[17] W. Podkoscielny, W. Charmas, Linear polythioesters. II. Products of interfacial polycondensation of 1, 4‐di (mercaptomethyl)‐naphthalene, 1, 5‐di (mercaptomethyl) naphthalene, and a mixture of 1, 4‐and 1, 5‐di (mercaptomethyl)‐naphthalene with terephthaloyl and isophthaloyl chlorides, Journal of Polymer Science: Polymer Chemistry Edition, 17 (1979) 2429-2438.
[18] W. Podkościelny, W. Charmas, Linear polythioesters. III. Products of interfacial polycondensation of 1, 4‐, 1, 5‐di (mercaptomethyl)‐naphthalene, and their mixture with adipoyl and sebacoyl chlorides, Journal of Polymer Science: Polymer Chemistry Edition, 17 (1979) 3811-3821.
[19] D. Abe, Y. Sasanuma, Molecular design, synthesis and characterization of aromatic polythioester and polydithioester, Polymer Chemistry, 3 (2012) 1576-1587.
[20] D. Abe, Y. Fukuda, Y. Sasanuma, Chemistry of aromatic polythioesters and polydithioesters, Polymer Chemistry, 6 (2015) 3131-3142.
[21] K.A. Stellmach, M.K. Paul, M. Xu, Y.-L. Su, L. Fu, A.R. Toland, H. Tran, L. Chen, R. Ramprasad, W.R. Gutekunst, Modulating polymerization thermodynamics of thiolactones through substituent and heteroatom incorporation, ACS Macro Letters, 11 (2022) 895-901.
[22] H. Wang, H. Lin, X. Li, R. Ren, J. Pu, H. Zhang, Y. Zheng, J. Zhao, S. Ng, H. Zhang, Application of Phase Transfer Catalysis in the Esterification of Organic Acids: The Primary Products from Ring Hydrocarbon Oxidation Processes, Catalysts, 9 (2019) 851.
[23] K. Maruoka, Practical aspects of recent asymmetric phase-transfer catalysis, Org. Process Res. Dev., 12 (2008) 679-697.
[24] N. Ohtani, T. Ohta, Y. Hosoda, T. Yamashita, Phase behavior and phase-transfer catalysis of tetrabutylammonium salts. Interface-mediated catalysis, Langmuir, 20 (2004) 409-415.
[25] Q. Han, Q. Wang, H. Wu, X. Ge, A. Gao, Y. Bai, S. Gao, G. Wang, X. Cao, Novel Naphthalimide‐Based Self‐Assembly Systems with Different Terminal Groups for Sensitive Detection of Thionyl Chloride and Oxalyl Chloride in Two Modes, ChemistrySelect, 7 (2022) e202200298.
[26] P.N. Nelson, W.H. Mulder, Thermodynamic and kinetic models for acid chloride formation: A computational and theoretical mechanistic study, J. Mol. Graphics Modell., 112 (2022) 108139.
[27] G. Taşkor Önel, N. Saygılı, Synthesis and Cyclooxygenase Enzyme Inhibitory Activity of Flurbiprofen Analogues: Simple Methodology of Their Nanoemulsion Systems, ChemistrySelect, 7 (2022) e202201654.
[28] P. Puthiaraj, Y.-R. Lee, S. Zhang, W.-S. Ahn, Triazine-based covalent organic polymers: design, synthesis and applications in heterogeneous catalysis, J. Mater. Chem. A, 4 (2016) 16288-16311.
[29] P. Fita, Toward understanding the mechanism of phase transfer catalysis with surface second harmonic generation, J. Physic. Chem. C, 118 (2014) 23147-23153.
[30] S. Baj, A. Siewniak, K. Bijak, Synthesis of peroxyesters in tri-liquid system using quaternary onium salts and polyethylene glycols as phase-transfer catalysts, Appl. Catal., A, 437 (2012) 184-189.
[31] S. Devaraju, P. Eswar, T. Gangadhar Reddy, K. Ravi Kumar, Metal salts used as an efficient catalyst to reduce the ring opening polymerization temperature of benzoxazines, Journal of Macromolecular Science, Part A, (2022) 1-7.
[32] S. Xiao, C. Akinyi, J. Longun, J.O. Iroh, Polyimide Copolymers and Nanocomposites: A Review of the Synergistic Effects of the Constituents on the Fire-Retardancy Behavior, Energies, 15 (2022) 4014.
[33] F.P. Marques, A.S. Colares, M.N. Cavalcante, J.S. Almeida, D. Lomonaco, L.M. Silva, M. de Freitas Rosa, R.C. Leitão, Optimization by Response Surface Methodology of Ethanosolv Lignin Recovery from Coconut Fiber, Oil Palm Mesocarp Fiber, and Sugarcane Bagasse, Indust. Eng. Chem. Res., 61 (2022) 4058-4067.
[34] K.-D. Kuehn, W. Ege, U. Gopp, Acrylic bone cements: mechanical and physical properties, Orthopedic Clinics, 36 (2005) 29-39.
[35] F. Pahlevanzadeh, H. Bakhsheshi-Rad, E. Hamzah, In-vitro biocompatibility, bioactivity, and mechanical strength of PMMA-PCL polymer containing fluorapatite and graphene oxide bone cements, Journal of the mechanical behavior of biomedical materials, 82 (2018) 257-267.
[36] C. Lee, The mechanical properties of PMMA bone cement, the well-cemented total hip arthroplasty, Springer2005, pp. 60-66.
[37] B. Świeczko-Żurek, A. Zieliński, D. Bociąga, K. Rosińska, G. Gajowiec, Influence of Different Nanometals Implemented in PMMA Bone Cement on Biological and Mechanical Properties, Nanomaterials, 12 (2022) 732.
[38] J. García-García, G. Azuara, O. Fraile-Martinez, C. García-Montero, M.A. Álvarez-Mon, S. Ruíz-Díez, M. Álvarez-Mon, J. Buján, N. García-Honduvilla, M.A. Ortega, Modification of the Polymer of a Bone Cement with Biodegradable Microspheres of PLGA and Loading with Daptomycin and Vancomycin Improve the Response to Bone Tissue Infection, Polymers, 14 (2022) 888.
