A NEW APPROACH TO SYNTHESIS METHACRYLIC MONOMERS N-ALKYLMETHACRYLAMIDE USING AN ECOLOGIC AND FRIENDLY CATALYST MAGHNITE H+
DOI:
https://doi.org/10.4314/jfas.v11i1.10Keywords:
Green chemistry; Montmorillonite clay; N-Alkylmethacrylamide; One-pot synthesis; Methacrylic anhydride.Abstract
In this paper, we have developed a novel procedure to synthesize four monomers formulated as 1,4-bis(Methacryloyl)Piperazine, N-Methacryloylmorpholine, N-Phenylmethacrylamide and N-Formyldimethacrylamide. N-Alkylmethacrylamide monomers are synthesized by the condensation of primary amine aniline and formamide or heterocyclic secondary amines such as piperazine and morpholine with methacrylic anhydride using an ecologic and friendly catalyst “Maghnite H+”, a proton exchanged montmorillonite clay by replacing a toxic reactant acryloyl chloride and triethylamine which are using in previously published studies. This new approach is even more interesting since this synthesis is carried out in bulk (without solvent) and at 0 °C for 2 hours, obtaining a better yield around 70% and selectivity to the product 100%. These monomers are characterized and confirmed by Infrared Spectroscopy (FTIR), 1H and 13C nuclear magnetic resonance (NMR) spectroscopy.
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References
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[2] Djamila CD, Meghabar R, Belbachir M. Piperazine Polymerization Catalyzed by Maghnite-H+. J. Envi. Anal. Chem. 2017, 4(3), 1000208.
[3] Medjdoub L, Rahmouni A, Belbachir M. New Approach for Synthesis of Hexa (Allylamino) Cyclotriphosphazene Catalysed by an Ecologic and Friendly Catalyst Layered Called Maghnite-H+(Algerian MMT). Glob. J. Sci. Front. Res: B. Chem. 2014, 14(2) ,1.
[4] Hachemaoui A, Belbachir M. Montmorillonite clay-catalysed synthesis of cyclic allylamines Mendeleev. Commun. 2005, 15(3), 124–125.
[5] Kaur N, Kishore D. Montmorillonite: An efficient, heterogeneous and green catalyst for organic synthesis. J. Chem. Pharm. Res. 2012, 4(2), 991-1015.
[6] Boonen J, Bronselaer A. Nielandt J. Veryser L, De Tré G., De Spiegeleer B. Alkamide database: Chemistry, occurrence and functionality of plant N-alkylamides. J.Ethnopharmacology. 2012, 142(3), 563–90.
[7] Jayasimha Reddy G., Venkata Naidu S., Rami Reddy A. V. Synthesis and Characterization of Poly (N-phenylmethacrylamide-co-methyl methacrylate) and Reactivity Ratios Determination J. Appl. Polym. Sci. 2003, 90, 2179 –2186.
[8] https://www.sigmaaldrich.com/materials-science/material-scienceproducts: Acrylic monomers (accessed on 21 April 2018).
[9] Ima K. Shundrina, Aleksandra D. Bukhtoyarova , Vladimlen V. Russkikh, Dmitry A. Parkhomenko, Vladimir V. Shelkovnikov. Synthesis and properties of novel random copolymers made from N-acryloylpiperazine-based monomers and fluoroalkylmethacrylate Polym. Bull. 2015, 72, 2783–2796.
[10] Julie L.N. Dubois, N Lavignac. Poly (amidoamine)s synthesis, characterization and interaction with BSA. Polym. Chem. 2013, DOI:10.1039/C3PY01121F.
[11] Boursier T., Georges S., Mosquet M., Rinaldi D., D’Agosto F. Synthesis of Poly(N-acryloylmorpholine) macromonomers using RAFT and their copolymerization with Methacrylic acid for the design of graft copolymer additives for concrete Polym. Chem. 2015, DOI: 10.1039/C5PY01730K.
[12] Gorman M, Chim Y. H, Hart A, Mathis O. Riehle, Andrew J. Urquhart. Poly (N-acryloylmorpholine): A simple hydrogel system for temporal and spatial control over cell adhesion. J. Biomed. Mater. Res. Part A . 2014,102, 1809-1815.
[13] Brooks A. Abel, Charles L. McCormick. Mechanistic insights into temperaturedependent trithiocarbonate chain-End degradation during the RAFT Polymerization of N-Arylmethacryamide. Macromol. 2016, 49, 465 – 474.
[14] Jayasimha Reddy G., Mohan Reddy M., Venkata Naidu S. Synthesis and characterization of functional acrylic copolymers of Acrylonitrile and N-Phenyl Mehacrylamide. Ind. J. Adv. Chem. Sci. 2014, 2(4), 264 - 270.
[15] Chytry V, Netopilik M, Bohdannecky M., Ulbrich K. Phase transition parameters of potential thermosensitive drug release systems based on polymers of N-alkylmethacrylamides. J. Biomater. Sci. Polymer. Edn. 1997, 8(11), 817-824.
DOI: 10.1163/ 156856297X00010.
[16] Hojabri F. J. Appl. Chem. Biotech., 1971, 21: 8.
[17] Belbachir, M. and Bensaoula. Composition and method for catalysis using bentonite. US Patent, 2003, 0069446A1
[18] Rahmouni A., Harrane A, Belbachir M. Structure and Physicochemical Properties of Polyaniline Synthesized in Presence of Maghnite clay Catalyst layered (Algerian Montmorillonite). Res. J. Mater. Sci. 2013, 1(3), 1-6.
[19] Belbachir M, Bensaoula A. Composition and method for catalysis using bentonite. U.S. Patent. 20016, 274,527 B1.
[20] Belbachir M, Bensaoula A. Composition and method for catalysis using bentonite. U.S. Patent. 2006, 7, 094,823 B2.
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Published
2018-12-06
How to Cite
DERKAOUI, S.; M. BELBACHIR, M. A NEW APPROACH TO SYNTHESIS METHACRYLIC MONOMERS N-ALKYLMETHACRYLAMIDE USING AN ECOLOGIC AND FRIENDLY CATALYST MAGHNITE H+. Journal of Fundamental and Applied Sciences, [S. l.], v. 11, n. 1, p. 142–153, 2018. DOI: 10.4314/jfas.v11i1.10. Disponível em: https://jfas.info/index.php/JFAS/article/view/54. Acesso em: 9 oct. 2025.
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