FUW TRENDS IN SCIENCE & TECHNOLOGY JOURNAL
(A Peer Review Journal)
e–ISSN: 2408–5162; p–ISSN: 2048–5170
keywords: Carbohydrate, 5-hydroxymethylfuran, 2,5-FDCA, polymers
2,5-furandicarboxylic acid (FDCA) and 2,5-bis-(hydroxymethyl)furan (BHMF) were synthesised as monomers from bio-based derived 5-Hydroxymethylfuran (5-HMF). The aldehyde group of 5-HMF was oxidized using potassium permanganate to FDCA with 80% yield and BHMF was synthesised from 5-HMF using sodium borohydride at 88% yield. Polymerization of FDCA with the following diols: 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol and BHMF via esterification reactions at 160-200oC using titanium (IV) n-butoxide catalyst. All these diols produced hydrophobic polymers under the same conditions with PBH-2,5-F more hydrophobic with a contact angle of 91o. The differences within this family of polymers are the number of carbon atoms in the linking diols and that BHMF had a different diol structure with a furan ring attached.
Alonso DM, Bond JQ & Dumesic JA 2010. Catalytic conversion of biomass to biofuels. Green Chemistry, 12: 1493-1513. Geboers JA, Van De Vyver S, Ooms R, Op De Beeck B, Jacobs PA & Sels BF 2011. Chemocatalytic conversion of cellulose: Opportunities, advances and pitfalls. Catalysis Science & Technology, 1: 714-726. Kobayashi H, Ohta H & Fukuoka A 2012. Conversion of lignocellulose into renewable chemicals by heterogeneous catalysis. Catalysis Sci. & Technology, 2: 869-883. Rosatella AA, Simeonov SP, Frade RFM & Afonso CAM 2011. 5-Hydroxymethylfurfural (Hmf) as a building block platform: Biological properties, synthesis and synthetic applications. Green Chemistry, 13: 754-793. Gandini A 2008. Polymers from renewable resources: A challenge for the future of macromolecular materials. Macromolecules, 41: 9491-9504. Cao Q, Guo XC, Yao SX, Guan J, Wang XY, Mu XD & Zhang DK 2011. Conversion of hexose into 5-hydroxymethylfurfural in imidazolium ionic liquids with and without a catalyst. Carbohydrate Research, 346: 956-959. Elliott DC, Beckman D, Bridgwater AV, Diebold JP, Gevert SB & Solantausta Y 1991. Developments in direct thermochemical liquefaction of biomass - 1983-1990. Energy & Fuels, 5: 399-410. Chen NY, Degnan TF & Koenig LR 1986. Liquid fuel from carbohydrates. Chemtech, 16: 506-511. Weisz PB, Haag WO & Rodewald PG 1979. Catalytic production of high-grade fuel (gasoline) from biomass compounds by shape-selective catalysis. Science, 206: 57-58. Katzen R & Tsao GT 2000. A view of the history of biochemical engineering. Advances in Biochemical Engineering/Biotechnology, 70: 77-91. Nasirudeen MB, Hailes HC & Evans JRG 2017. Preparation of 5-hydroxymethylfurfural from glucose and fructose in ionic liquids by reactive vacuum distillation over a solid catalyst. Current Organic Synthesis, 14: 596-603. D570-98, A 2010. Standard Test Method for Water Absorption of Plastics, pp. 1-4. Gandini A, Silvestre AJD, Neto CP, Sousa AF & Gomes M 2009a. The furan counterpart of poly(ethylene terephthalate): An alternative material based on renewable resources. J. Polymer Sci. Part a-Polymer Chem., 47: 295-298. Gandini A, Coelho D, Gomes M, Reis B & Silvestre A 2009b. Materials from renewable resources based on furan monomers and furan chemistry: Work in progress. J. Materials Chem., 19: 8656-8664. Silverstein R, Webster F & Kiemle D 2005. Spectrometric Identification of Organic Compounds. Hoboken: John Wiley & Sons Inc. Mohrig JR, Hammond CN & Schatz PF 2006. Techniques in Organic Chemistry. 2nd ed. New York: WH Freeman and Company. Mitiakoudis A & Gandini A 1991. Synthesis and characterization of furanic polyamides. Macromolecules, 24: 830-835. Rass HA, Essayem N & Besson M 2013. Selective aqueous phase oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Pt/C catalysts: Influence of the base and effect of bismuth promotion. Green Chemistry, 15: 2240-2251. Ma J, Pang Y, Wang M, Xu J, Ma H & Nie X 2012. The copolymerization reactivity of diols with 2,5-furandicarboxylic acid for furan-based copolyester materials. J. Materials Chem., 22: 3457-3461. Zhang L, Zhao N & Xu J 2014. Fabrication and application of superhydrophilic surfaces: A review. J. Adhesion Sci. & Techn., 28: 769-790. Yuan Y & Lee TR 2013. Contact angle and wetting properties. In: Bracco G & Holts B (eds.) Surface Science Techniques. 51 ed. Berlin Heidelberg: Springer-Verlag. Vogler EA 1998. Structure and reactivity of water at biomaterial surfaces. Advances in Colloid and Interface Science, 74: 69-117. Guo CW, Wang ST, Liu H, Feng L, Song YL & Jiang L 2008. Wettability alteration of polymer surfaces produced by scraping. J. Adhesion Sci. & Techn., 22: 395-402. Taylor M, Urquhart AJ, Zelzer M, Davies MC & Alexander MR 2007. Picoliter water contact angle measurement on polymers. Langmuir, 23: 6875-6878. Ruiz-Cabello FJM, Rodriguez-Valverde MA & Cabrerizo-Vilchez MA 2011. Comparison of the Relaxation of Sessile Drops Driven by Harmonic and Stochastic Mechanical Excitations. Langmuir, 27: 8748-8752.
