Unsaturated Polyester Resins and Fiber-Reinforced Polymer Composites from Plant Biomass

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We are the first to report the synthesis of maleic acid in quantitative yield by oxidation of 5-hydroxymethyl furfural with hydrogen peroxide in the presence of sodium bicarbonate in an aqueous medium under ambient conditions without the using of toxic catalysts and solvents. 5-hydroxymethyl furfural and 2,5-furandicarboxylic acid have been prepared from hexose plant biomass. Based on maleic anhydride and 2,5-furandicarboxylic acid, unsaturated polyesters were synthesized for the first time from renewable raw materials only. A fiber-reinforced polymer composite based on these polyester resins have been prepared. Strength properties of carbon and glass fiber-reinforced polymer composites are 1.5 times superior to the strength of similar phthalic acid based composites.

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169-174

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October 2020

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© 2020 Trans Tech Publications Ltd. All Rights Reserved

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[1] M. Matos, A.F. Sousa, A.C. Fonseca, C.S.R. Freire, J.F.J. Coelho, A.J.D. Silvestre, A new generation of furanic copolyesters with enhanced degradability: poly(ethylene 2,5-furandicarboxylate)-co-poly(lactic acid) copolyesters, Macromol. Chem. Phys. 215 (2014) 2175-2184.

DOI: 10.1002/macp.201400175

Google Scholar

[2] C. Vilela, A.F. Sousa, A.C. Fonseca, A.C. Serra, J.F.J. Coelho, C.S.R. Freire, A.J.D. Silvestre, The quest for sustainable polyesters – insights into the future, Polym.Chem. 5 (2014) 3119-3141.

DOI: 10.1039/c3py01213a

Google Scholar

[3] F.H. Isikgor, C.R. Becer, Lignocellulosic Biomass: a sustainable platform for production of bio-based chemicals and polymers, Polym. Chem. 6 (2015) 4497-4559.

DOI: 10.1039/c5py00263j

Google Scholar

[4] D. Juais, A.F. Naves, C. Li, R. Gross, L.H. Catalani, Isosorbide Polyesters from Enzymatic Catalysis, Macromolecules. 43 (2010) 10315-10319.

DOI: 10.1021/ma1013176

Google Scholar

[5] F. Pion, A.F. Reano, P.-H. Ducrot, F. Allais, Chemo-enzymatic preparation of new bio-based bis- and trisphenols: new versatile building blocks for polymer chemistry, RSC Adv. 3 (2013) 8988.

DOI: 10.1039/c3ra41247d

Google Scholar

[6] J.J. Bozell, G.R. Petersen, Technology development for the production of biobased products from biorefinery carbohydrates the US Department of Energy's Top 10, revisited, Green Chem. 12 (2010) 539-554.

DOI: 10.1039/b922014c

Google Scholar

[7] V.A. Klushin, K.I. Galkin, V.P. Kashparova, et al., Technological aspects of fructose conversion to high-purity 5-hydroxymethylfurfural, a versatile platform chemical, Russ. J. Org. Chem. 52 (2016) 767-771.

DOI: 10.1134/s1070428016060014

Google Scholar

[8] D. Chernysheva, V. Klushin, A. Zubenko, et al., Base-free aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Pt/C catalysts synthesized by pulse alternating current technique, Mend. Commun. 28 (2018) 431-433.

DOI: 10.1016/j.mencom.2018.07.031

Google Scholar

[9] A. F. Sousa, C. Vilela, A. C. Fonseca, M. Matos, C. S. R. Freire, G.-J. M. Gruter, , J. F. J. Coelho, A. J. D. Silvestre, Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency, Polym. Chem. 6 (2015) 5961–5983.

DOI: 10.1039/c5py00686d

Google Scholar

[10] A. Gandini, A.J.D. Silvestre, C.P. Neto, A.F. Sousa, M. Gomes, The furan counterpart of poly(ethylene terephthalate): An alternative material based on renewable resources, J. Polym. Sci. Polym. Chem. 47 (2009) 295-298.

DOI: 10.1002/pola.23130

Google Scholar

[11] T. Werpy, G. Petersen, Top Value Added Chemicals from Biomass. Volume I Results of Screening for Potential Candidates from Sugars and Synthesis Gas, Pacific Northwest National Laboratory, (2004).

DOI: 10.2172/15008859

Google Scholar

[12] A.F. Sousa, M. Matos, C.S.R. Freire, A.J.D. Silvestre, J.F.J. Coelho, New copolyesters derived from terephthalic and 2,5-furandicarboxylic acids: A step forward in the development of biobased polyesters, Polymer. 54 (2013) 513-519.

DOI: 10.1016/j.polymer.2012.11.081

Google Scholar

[13] C.H.R.M. Wilsens, N.J.M. Wullems, E. Gubbels, Y. Yao, S. Rastogi, B.A.J. Noordover, Synthesis, kinetics, and characterization of bio-based thermosets obtained through polymerization of a 2,5-furandicarboxylic acid-based bis(2-oxazoline) with sebacic acid, Polym. Chem. 6 (2015) 2707-2716.

DOI: 10.1039/c4py01609b

Google Scholar

[14] J.K. Fink, Reactive Polymers Fundamentals and Applications, William Andrew Publishing, New York, (2013).

Google Scholar

[15] X. Li, Y. Zhang, The conversion of 5-hydroxymethyl furfural (HMF) to maleic anhydride with vanadium-based heterogeneous catalysts, Green Chemistry. 18 (2016) 643-647.

DOI: 10.1039/c5gc01794g

Google Scholar

[16] Z. Du, et al., Oxidation of 5-hydroxymethylfurfural to maleic anhydride with molecular oxygen, Green Chemistry. 13 (2011) 554-557.

Google Scholar

[17] H. Guo, G. Yin, Catalytic aerobic oxidation of renewable furfural with phosphomolybdic acid catalyst: an alternative route to maleic acid, The Journal of Physical Chemistry C. 115 (2011) 17516-17522.

DOI: 10.1021/jp2054712

Google Scholar

[18] J. Lan, et al., Transformation of 5-hydroxymethylfurfural (HMF) to maleic anhydride by aerobic oxidation with heteropolyacid catalysts, ACS Catalysis. 5 (2015) 2035-2041.

DOI: 10.1021/cs501776n

Google Scholar

[19] M. Rezaei, et al., Furfural oxidation to maleic acid with H2O2 by using vanadyl pyrophosphate and zirconium pyrophosphate supported on well-ordered mesoporous KIT-6, Journal of Environmental Chemical Engineering. 7 (2019) 102855.

DOI: 10.1016/j.jece.2018.102855

Google Scholar

[20] X. Li, et al., Highly efficient formic acid-mediated oxidation of renewable furfural to maleic acid with H2O2, Green Chemistry. 19 (2017) 914-918.

DOI: 10.1039/c6gc03020c

Google Scholar