Synthesis and characterization of bio-based polymer derived from 2,5-furandicarboxylic acid and 1,4-butanediol
Main Article Content
Abstract
Nowadays, petroleum-based polymers are currently dominant in material industries, with wide scope applications. However, due to the finite supply of fossil fuels as well as the negative effects on the environment while utilizing them, the need of developing bio-based alternatives is dramatically increase. Recently, the biopolymers derived from 2,5-furandicarboxylic acid (FDCA) have been gradually investigated; however, some of their thermal and mechanical properties are not fully understood. Herein, we are conducting research about a FDCA-derived biopolymer – poly(butylene 2,5-furandicarboxylate) (PBF), which was synthesized from FDCA and butane-1,4-diol by the melting polycondensation. 1H NMR and IR spectrum confirmed the linear structure of this polyester, then TGA and DSC results were analyzed to indicate the melting point at 159 ºC and the thermal degradation at 357 ºC.
Keywords
poly(butylene 2,5-furandicarboxylate), FDCA, chemical structure of PBF, thermal properties
Article Details
References
[1] F.D. Pileidis, M.M. Titirici, Levulinic acid biorefineries: new challenges for efficient utilization of biomass, ChemSusChem, 9 (2016) 562-582.
[2] J. Duo, Z. Zhang, G. Yao, Z. Huo, F. Jin, Hydrothermal conversion of glucose into lactic acid with sodium silicate as a base catalyst, Catalysis Today, 263 (2016) 112-116.
[3] A.F. Sousa, J.F. Coelho, A.J. Silvestre, Renewable-based poly ((ether) ester) s from 2, 5-furandicarboxylic acid, Polymer, 98 (2016) 129-135.
[4] C. Rizescu, I. Podolean, J. Albero, V.I. Parvulescu, S.M. Coman, C. Bucur, M. Puche, H. Garcia, N-Doped graphene as a metal-free catalyst for glucose oxidation to succinic acid, Green Chemistry, 19 (2017) 1999-2005.
[5] K.D. Green, M.K. Turner, J.M. Woodley, Candida cloacae oxidation of long-chain fatty acids to dioic acids, Enzyme microbial technology, 27 (2000) 205-211.
[6] N. Li, Y. Zheng, L. Wei, H. Teng, J. Zhou, Metal nanoparticles supported on WO₃ nanosheets for highly selective hydrogenolysis of cellulose to ethylene glycol, Green Chemistry, 19 (2017) 682-691.
[7] 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.
[8] A. Gandini, A.J. Silvestre, C.P. Neto, A.F. Sousa, M. Gomes, The furan counterpart of poly (ethylene terephthalate): An alternative material based on renewable resources, Journal of Polymer Science Part A: Polymer Chemistry, 47 (2009) 295-298.
[9] 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.
[10] S.K. Burgess, J.E. Leisen, B.E. Kraftschik, C.R. Mubarak, R.M. Kriegel, W.J. Koros, Chain mobility, thermal, and mechanical properties of poly (ethylene furanoate) compared to poly (ethylene terephthalate), Macromolecules, 47 (2014) 1383-1391.
[11] S.K. Burgess, D.S. Mikkilineni, B.Y. Daniel, D.J. Kim, C.R. Mubarak, R.M. Kriegel, W.J. Koros, Water sorption in poly (ethylene furanoate) compared to poly (ethylene terephthalate). Part 2: Kinetic sorption, Polymer, 55 (2014) 6870-6882.
[12] S.K. Burgess, O. Karvan, J.R. Johnson, R.M. Kriegel, W.J. Koros, Oxygen sorption and transport in amorphous poly(ethylene furanoate), Polymer, 55 (2014) 4748-4756.
[13] W.L. Jenkins, G. Rhodes, M. Rule, Process to prepare high molecule weight polyester, Google Patents, 1992.
[14] J. Zhu, J. Cai, W. Xie, P.-H. Chen, M. Gazzano, M. Scandola, R.A. Gross, Poly (butylene 2, 5-furandicarboxylate), a biobased alternative to PBT: synthesis, physical properties, and crystal structure, Macromolecules, 46 (2013) 796-804.
[15] J. Ma, X. Yu, J. Xu, Y. Pang, Synthesis and crystallinity of poly (butylene 2, 5-furandicarboxylate), Polymer, 53 (2012) 4145-4151.
[16] N. Poulopoulou, G. Kantoutsis, D.N. Bikiaris, D.S. Achilias, M. Kapnisti, G.Z. Papageorgiou, Biobased engineering thermoplastics: poly (butylene 2, 5-furandicarboxylate) blends, Polymers, 11 (2019) 937.
[17] M. Gomez, M. Cozine, A. Tonelli, High-resolution solid-state carbon-13 NMR study of the α and β crystalline forms of poly (butylene terephthalate), Macromolecules, 21 (1988) 388-392.
[2] J. Duo, Z. Zhang, G. Yao, Z. Huo, F. Jin, Hydrothermal conversion of glucose into lactic acid with sodium silicate as a base catalyst, Catalysis Today, 263 (2016) 112-116.
[3] A.F. Sousa, J.F. Coelho, A.J. Silvestre, Renewable-based poly ((ether) ester) s from 2, 5-furandicarboxylic acid, Polymer, 98 (2016) 129-135.
[4] C. Rizescu, I. Podolean, J. Albero, V.I. Parvulescu, S.M. Coman, C. Bucur, M. Puche, H. Garcia, N-Doped graphene as a metal-free catalyst for glucose oxidation to succinic acid, Green Chemistry, 19 (2017) 1999-2005.
[5] K.D. Green, M.K. Turner, J.M. Woodley, Candida cloacae oxidation of long-chain fatty acids to dioic acids, Enzyme microbial technology, 27 (2000) 205-211.
[6] N. Li, Y. Zheng, L. Wei, H. Teng, J. Zhou, Metal nanoparticles supported on WO₃ nanosheets for highly selective hydrogenolysis of cellulose to ethylene glycol, Green Chemistry, 19 (2017) 682-691.
[7] 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.
[8] A. Gandini, A.J. Silvestre, C.P. Neto, A.F. Sousa, M. Gomes, The furan counterpart of poly (ethylene terephthalate): An alternative material based on renewable resources, Journal of Polymer Science Part A: Polymer Chemistry, 47 (2009) 295-298.
[9] 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.
[10] S.K. Burgess, J.E. Leisen, B.E. Kraftschik, C.R. Mubarak, R.M. Kriegel, W.J. Koros, Chain mobility, thermal, and mechanical properties of poly (ethylene furanoate) compared to poly (ethylene terephthalate), Macromolecules, 47 (2014) 1383-1391.
[11] S.K. Burgess, D.S. Mikkilineni, B.Y. Daniel, D.J. Kim, C.R. Mubarak, R.M. Kriegel, W.J. Koros, Water sorption in poly (ethylene furanoate) compared to poly (ethylene terephthalate). Part 2: Kinetic sorption, Polymer, 55 (2014) 6870-6882.
[12] S.K. Burgess, O. Karvan, J.R. Johnson, R.M. Kriegel, W.J. Koros, Oxygen sorption and transport in amorphous poly(ethylene furanoate), Polymer, 55 (2014) 4748-4756.
[13] W.L. Jenkins, G. Rhodes, M. Rule, Process to prepare high molecule weight polyester, Google Patents, 1992.
[14] J. Zhu, J. Cai, W. Xie, P.-H. Chen, M. Gazzano, M. Scandola, R.A. Gross, Poly (butylene 2, 5-furandicarboxylate), a biobased alternative to PBT: synthesis, physical properties, and crystal structure, Macromolecules, 46 (2013) 796-804.
[15] J. Ma, X. Yu, J. Xu, Y. Pang, Synthesis and crystallinity of poly (butylene 2, 5-furandicarboxylate), Polymer, 53 (2012) 4145-4151.
[16] N. Poulopoulou, G. Kantoutsis, D.N. Bikiaris, D.S. Achilias, M. Kapnisti, G.Z. Papageorgiou, Biobased engineering thermoplastics: poly (butylene 2, 5-furandicarboxylate) blends, Polymers, 11 (2019) 937.
[17] M. Gomez, M. Cozine, A. Tonelli, High-resolution solid-state carbon-13 NMR study of the α and β crystalline forms of poly (butylene terephthalate), Macromolecules, 21 (1988) 388-392.