Study on the Synthesis of 6-Hydroxyhexyl 5-(Hydroxymethyl) Furan-2-Carboxylate from 5-Hydroxymethylfurfural (HMF) and Alkanediols
Main Article Content
Abstract
Nowadays, due to the fact that the term ‘sustainable development’ has caught everyone’s attention, chemists have been researching substances which obtainable via synthesizing biocompounds. Recently, scientists found out that 5-hydroxylmethylfurfural (HMF), which can be synthesized via dehydration reaction of common biocompounds like polysaccharides, has a great potential of forming novel derivatives to utilize in the biopolymer manufacturing field. HMF oxidative esterification is one of the notable reactions of which the outcome seems promising and applicable. In this research, the esterification of HMF and hexane-1,6-diol took place directly in DMSO or TEA solvent using Ru/C, Co3O4-N@C as catalysts, base K3PO4; with oxygen 1 bar as an oxidant. LC-MS/MS analysis was used to detect the presence of the ester products; however, due to the low conversion and selectivity, the content of desired product is not enough to isolate and confirm its structure.
Keywords
HMF, oxidative esterification, biopolymer
Article Details
References
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[4] L.M. de Espinosa, M.A. Meier, Plant oils: The perfect renewable resource for polymer science, European Polymer Journal, 47 (2011) 837-852.
[5] A.A. Rosatella, S.P. Simeonov, R.F. Frade, C.A. Afonso, 5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications, Green Chemistry, 13 (2011) 754-793. https://doi.org/10.1016/j.eurpolymj.2010.11.020
[6] Y. Su, H.M. Brown, X. Huang, X.-d. Zhou, J.E. Amonette, Z.C. Zhang, Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical, Applied Catalysis A: General, 361 (2009) 117-122. https://doi.org/10.1039/c0gc00401d
[7] Y. Mao, R.M. Kriegel, D.G. Bucknall, The crystal structure of poly (ethylene furanoate), Polymer, 102 (2016) 308-314. https://doi.org/10.1016/j.polymer.2016.08.052
[8] A. Codou, M. Moncel, J.G. van Berkel, N. Guigo, N. Sbirrazzuoli, Glass transition dynamics and cooperativity length of poly (ethylene 2, 5-furandicarboxylate) compared to poly (ethylene terephthalate), Physical Chemistry Chemical Physics, 18 (2016) 16647-16658. https://doi.org/10.1039/C6CP01227B
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[10] G.Z. Papageorgiou, V. Tsanaktsis, D.N. Bikiaris, Synthesis of poly (ethylene furandicarboxylate) polyester using monomers derived from renewable resources: thermal behavior comparison with PET and PEN, Physical Chemistry Chemical Physics, 16 (2014) 7946-7958. https://doi.org/10.1039/C4CP00518J
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[13] R.V. Jagadeesh, H. Junge, M.-M. Pohl, J.r. Radnik, A. Brückner, M. Beller, Selective oxidation of alcohols to esters using heterogeneous Co3O4-N@C catalysts under mild conditions, Journal of the American Chemical Society, 135 (2013) 10776-10782. https://doi.org/10.1021/ja403615c
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[15] A. Salazar, P. Hünemörder, J. Rabeah, A. Quade, R.V. Jagadeesh, E.J.A.S.C. Mejia, Engineering, synergetic bimetallic oxidative esterification of 5-hydroxymethylfurfural under mild conditions, 7 (2019) 12061-12068. https://doi.org/10.1021/acssuschemeng.9b00914
[16] M. Jiang, Q. Liu, Q. Zhang, C. Ye, G. Zhou, A series of furan‐aromatic polyesters synthesized via direct esterification method based on renewable resources, Journal of Polymer Science Part A: Polymer Chemistry, 50 (2012) 1026-1036. https://doi.org/10.1002/pola.25859
[17] J. Zhu, J. Cai, W. Xie, P.-H. Chen, M. Gazzano, M. Scandola, R.A. Gross, Poly (butylene 2, 5-furan dicarboxylate), a biobased alternative to PBT: synthesis, physical properties, and crystal structure, Macromolecules, 46 (2013) 796-804. https://doi.org/10.1021/ma3023298
[18] G. An, H. Ahn, K.A. De Castro, H. Rhee, Pd/C and NaBH4 in basic aqueous alcohol: an efficient system for an environmentally benign oxidation of alcohols, Synthesis, 2010 (3) 477-485. https://doi.org/10.1055/s-0029-1217115
[19] S.E. Davis, M.S. Ide, R.J. Davis, Selective oxidation of alcohols and aldehydes over supported metal nanoparticles, Green Chemistry, 15 (2013) 17-45. https://doi.org/10.1039/C2GC36441G