Acidic Metal-Based Functional Ionic Liquids Catalyze the Synthesis of Bio-Based PEF Polyester

Qiao Zhou; Yuanyuan Zhao; Yafei Shi; Rongrong Zheng; Liying Guo

doi:10.3390/polym16010103

journal article Open Access Dec 29, 2023

Acidic Metal-Based Functional Ionic Liquids Catalyze the Synthesis of Bio-Based PEF Polyester

Qiao Zhou Yuanyuan Zhao

Yafei Shi Rongrong Zheng

Liying Guo

Polymers Vol. 16 No. 1 pp. 103 · MDPI AG

View at Publisher Save 10.3390/polym16010103

Abstract

Utilizing triethylenediamine (DA), 1,3-propanesultone (PS), whose ring opens during the formation of the dizwiterion-intermediate DA-2PS, and the metal chlorides XCly, where X = Sn(IV), Zn(II),Al(III), Fe(III) and Mn(II), are used for the synthesis of five kinds of acidic metal-based functionalized ionic liquid catalysts ([DA-2PS][XCly]2). Their chemical structures, thermal stability and dual acidic active site were analyzed. We investigated the performance of [DA-2PS][XCly]2 in catalyzing the esterification reaction between 2,5-furandicarboxylic acid (FDCA) and ethylene glycol (EG) to synthesize poly (ethylene 2,5-furandicarboxylate)(PEF). Among the catalysts tested, [DA-2PS][SnCl5]2 exhibited the best catalytic performance under identical process parameters, and the optimal catalyst dosage was determined to be 0.05 mol% based on FDCA. The optimal conditions for the reaction were predicted using response surface methodology: a feed ratio of EG:FDCA = 1.96:1, an esterification temperature of 219.86 °C, a polycondensation temperature of 240.04 °C and a polycondensation time of 6.3 h, with a intrinsic viscosity of 0.67 dL·g−1. The resulting PEF was experimentally verified to exhibit an intrinsic viscosity of 0.68 dL·g−1 and a number average molecular weight of 28,820 g·mol−1. Finally, the structure and thermal properties of PEF were characterized. The results confirmed that PEF possessed the correct structure, exhibited high thermal stability and demonstrated excellent thermal properties.

Topics

No keywords indexed for this article. Browse by subject →

References

36

[1]

Mendieta "Bio-polyethylene furanoate (Bio-PEF) from lignocellulosic biomass adapted to the circular bioeconomy" BioResources (2022) 10.15376/biores.17.4.mendieta

[2]

Sousa "Renewable-based poly ((ether) ester)s from 2,5-furandicarboxylic acid" Polymer (2016) 10.1016/j.polymer.2016.06.015

[3]

Post "Biobased 2,5-Bis (hydroxymethyl) furan as a Versatile Building Block for Sustainable Polymeric Materials" ACS Omega (2023) 10.1021/acsomega.2c07629

[4]

Burgess "Carbon dioxide sorption and transport in amorphous poly (ethylene furanoate)" Macromolecules (2015) 10.1021/acs.macromol.5b00333

[5]

Guigo "Isothermal crystallization kinetics of poly (ethylene 2,5-furandicarboxylate). Macromol" Mater. Eng. (2015)

[6]

Wu "DBU-catalyzed biobased poly(ethylene 2,5-furandicarboxylate) polyester with rapid melt crystallization: Synthesis, crystallization kinetics and melting behavior" RSC Adv. (2017) 10.1039/c7ra90035j

[7]

Knoop "High molecular weight poly(ethylene-2,5-furanoate); Critical aspects in synthesis and mechanical property determination" J. Polym. Sci. Polym. Chem. (2013) 10.1002/pola.26833

[8]

Jiang "A series of furan-aromatic polyesters synthesized via direct esterification method based on renewable resources" J. Polym. Sci. Polym. Chem. (2012) 10.1002/pola.25859

[9]

Hill "Studies of Polymerization and Ring Formation. XX. Many-Membered Cyclic Esters" J. Am. Chem. Soc. (1933) 10.1021/ja01339a055

[10]

deIlarduya "Poly (alkylene 2,5-furandicarboxylate) s (PEF and PBF) by ring opening polymerization" Polymer (2016) 10.1016/j.polymer.2016.02.003

[11]

Moore "Polyesters derived from furan and tetrahydrofuran nuclei" Macromolecules (1978) 10.1021/ma60063a028

[12]

Gandini "Materials from renewable resources based on furan monomers and furan chemistry: Work in progress" J. Mater. Chem. (2009) 10.1039/b909377j

[13]

Gomes "Synthesis and characterization of poly (2,5-furan dicarboxylate) s based on a variety of diols" J. Polym. Sci. Pol. Chem. (2011) 10.1002/pola.24812

[14]

Jiang "Enzymatic synthesis of biobased polyesters using 2,5-bis (hydroxymethyl) furan as the building block" Biomacromolecules (2014) 10.1021/bm500340w

[15]

Hong "High molecular weight bio furan-based co-polyesters for food packaging applications: Synthesis, characterization and solid-state polymerization" Green Chem. (2016) 10.1039/c6gc01060a

[16]

Terzopoulou "Effect of catalyst type on recyclability and decomposition mechanism of poly (ethylene furanoate) biobased polyester" J. Anal. Appl. Pyrolysis. (2017) 10.1016/j.jaap.2017.05.010

[17]

Gruter "Accelerating research into bio-based FDCA-polyesters by using small scale parallel film reactors" Comb. Chem. High Throughput Screen. (2012) 10.2174/138620712798868374

[18]

Martino "Influence of organically modified montmorillonite and sepiolite clays on the physical properties of bio-based poly (ethylene 2,5-furandicarboxylate)" Compos. Part B Eng. (2017) 10.1016/j.compositesb.2016.11.008

[19]

Joshi "Role of enhanced solubility in esterification of 2,5-furandicarboxylic acid with ethylene glycol at reduced temperatures: Energy efficient synthesis of poly (ethylene 2, 5-furandicarboxylate)" React. Chem. Eng. (2018) 10.1039/c8re00086g

[20]

Gopalakrishnan "Synthesis and characterization of bio-based furanic polyesters" J. Polym. Res. (2014) 10.1007/s10965-013-0340-0

[21]

Gubbels "Linear and branched polyester resins based on dimethyl-2, 5-furandicarboxylate for coating applications" Eur. Polym. J. (2013) 10.1016/j.eurpolymj.2013.06.019

[22]

Wang, J., Liu, X., Zhu, J., and Jiang, Y. (2017). Copolyesters based on 2, 5-furandicarboxylic acid (FDCA): Effect of 2, 2, 4, 4-tetramethyl-1, 3-cyclobutanediol units on their properties. Polymers, 9. 10.3390/polym9090305

[23]

Wang "Modification of poly (ethylene 2, 5-furandicarboxylate) with 1, 4-cyclohexanedimethylene: Influence of composition on mechanical and barrier properties" Polymer (2016) 10.1016/j.polymer.2016.09.030

[24]

Wu "Semi-Aromatic Polyesters Based on a Carbohydrate-Derived Rigid Diol for Engineering Plastics" ChemSusChem (2015) 10.1002/cssc.201402935

[25]

Miao "Ionic liquids for supercapacitive energy storage: A mini-review" Energy Fuels. (2021) 10.1021/acs.energyfuels.1c00321

[26]

Yan "Recent advances in ionic liquid-mediated SO2 capture" Ind. Eng. Chem. Res. (2019) 10.1021/acs.iecr.9b01959

[27]

Li "Biodiesel production from Camptotheca acuminata seed oil catalyzed by novel Brönsted–Lewis acidic ionic liquid" Appl. Energy (2014) 10.1016/j.apenergy.2013.10.025

[28]

Gupta "Low-viscosity ionic liquid-doped solid polymer electrolytes: Electrical, dielectric, and ion transport studies" High Perform. Polym. (2018) 10.1177/0954008318778763

[29]

Zhao "Preparation of Keggin-type monosubstituted polyoxometalate ionic liquid catalysts and their application in catalyzing the coupling reaction of ethylene carbonate and dimethyl succinate to synthesize poly (ethylene succinate)" N. J. Chem. (2022) 10.1039/d2nj03094b

[30]

Ma "Tailoring molecular weight of bioderived polycarbonates via bifunctional ionic liquids catalysts under metal-free conditions" ACS Sustain. Chem. Eng. (2018) 10.1021/acssuschemeng.7b04284

[31]

Zhang "Synthesis of high-molecular weight isosorbide-based polycarbonates through efficient activation of endo-hydroxyl groups by an ionic liquid" Green Chem. (2019) 10.1039/c9gc01500k

[32]

Peng "Direct polycondensation of l-lactic acid in hydrophobic bis (trifluoromethanesulfonyl) imide-anionic ionic liquids: A kinetic study" Eur. Polym. J. (2021) 10.1016/j.eurpolymj.2021.110692

[33]

Zhao "Preparation of biacidic tin-based ionic liquid catalysts and their application in catalyzing coupling reaction between ethylene carbonate and dimethyl succinate to synthesize poly (ethylene succinate)" N. J. Chem. (2022) 10.1039/d2nj03225b

[34]

Qu "A Brønsted Acidic Ionic Liquid as an Efficient and Selective Catalyst System for Bioderived High Molecular Weight Poly (ethylene 2, 5-furandicarboxylate)" ChemSusChem (2019) 10.1002/cssc.201902020

[35]

(1989). Determination of Limiting Viscosity Number of Polyacrylamide (Standard No. GB/T 12005.1-1989).

[36]

Xie "Biobased poly(ethylene-co-hexamethylene 2,5- furandicarboxylate) (PEHF) copolyesters with superior tensile properties" Ind. Eng. Chem. Res. (2018) 10.1021/acs.iecr.8b03204

Metrics

8

Citations

36

References

Details

Published: Dec 29, 2023
Vol/Issue: 16(1)
Pages: 103
License: View

Authors

Q

Qiao Zhou