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Synthesis of Fully Biobased Polyesters from Plant Oil

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Department of Agricultural, Food and Nutritional Science, University of Alberta, 4-10 Agric/For Centre, Edmonton, Alberta T6G 2P5, Canada
Department of Polymer Science and Engineering, Zhejiang University, Zhe Da Road 38, Hangzhou 310027, China
*E-mail: [email protected]. Phone: +1 (780) 492-4845. Fax: +1 (780) 492-4265.
Cite this: ACS Sustainable Chem. Eng. 2017, 5, 11, 9793–9801
Publication Date (Web):September 14, 2017
https://doi.org/10.1021/acssuschemeng.7b01668
Copyright © 2017 American Chemical Society

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    Abstract

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    Self-metathesis of fatty acid methyl esters (FAMEs) from natural oils and commercial oleic acid was carried out using a microwave reactor in solvent-free conditions. Self-metathesis products were further identified and quantified by gas chromatography–mass spectroscopy (GC–MS) and gas chromatography–flame ionization detector (GC–FID). Conversion of ∼50% was achieved within a short span (∼2 min) in the presence of 0.05 mol % Hoveyda–Grubbs second generation catalyst (HG2) giving an equilibrium mixture of alkenes, α,ω-diester, and FAMEs. Highly pure dimethyl-9-octadecene-1,18-dioate (diester) was separated, and the desired quantity of it was reduced to 9-octadecene-1,18-diol (diol). Condensation polymerization of diester and diol as monomers was performed using conventional heating, microwave irradiation, and microwaves coupled with conventional heating. Characterization and analysis of synthesized biopolyesters were carried out using different techniques including nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), gel permeation chromatography (GPC), thermal gravimetric analysis (TGA), dynamic mechanical analysis (DMA), and tensile tests. Polyesters with the highest molecular weight of 337 kDa, ∼50 °C melting point, degradation temperature of about 400 °C, and the maximum strength of ∼5.5 MPa were obtained. These materials have great future potential to be used in different applications as a substitute of nonrenewable polyesters.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.7b01668.

    • Methodology for preparation of compounds, HRMS, 1H NMR, 13C NMR, GC–MS and GC–FID data, table of polyester data, polyester film images, GPC, DMA, and mechanical testing results (PDF)

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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 14 publications.

    1. Saadman Sakib Rahman, Muhammad Arshad, Ahmed Qureshi, Aman Ullah. Fabrication of a Self-Healing, 3D Printable, and Reprocessable Biobased Elastomer. ACS Applied Materials & Interfaces 2020, 12 (46) , 51927-51939. https://doi.org/10.1021/acsami.0c14220
    2. Reza Ahmadi, Aman Ullah. Synthesis and Characterization of Unsaturated Biobased-Polyamides from Plant Oil. ACS Sustainable Chemistry & Engineering 2020, 8 (21) , 8049-8058. https://doi.org/10.1021/acssuschemeng.0c02692
    3. Geeti Kaberi Dutta, Niranjan Karak. One-Pot Synthesis of Bio-Based Waterborne Polyester as UV-Resistant Biodegradable Sustainable Material with Controlled Release Attributes. ACS Omega 2018, 3 (12) , 16812-16822. https://doi.org/10.1021/acsomega.8b02790
    4. Duy Le, Chanatip Samart, Ken Tsutsumi, Kotohiro Nomura, Suwadee Kongparakul. Efficient Conversion of Renewable Unsaturated Fatty Acid Methyl Esters by Cross-Metathesis with Eugenol. ACS Omega 2018, 3 (9) , 11041-11049. https://doi.org/10.1021/acsomega.8b01695
    5. Pranabesh Sahu, Lav Sharma, Tim Dawsey, Ram K. Gupta. Insight into the synthesis and thermomechanical properties of “short‐long” type biobased aliphatic polyesters. Journal of Applied Polymer Science 2024, 141 (8) https://doi.org/10.1002/app.54972
    6. Xinhan Zhang, Pengfei Li, Jinsong Zeng, Jinpeng Li, Wenhua Gao, Bin Wang, Jun Xu, Kefu Chen. Acetylated cellulose nanofibers enhanced bio-based polyesters derived from 10-undecanoic acid toward recyclable and degradable plastics. Chemical Engineering Journal 2024, 479 , 147797. https://doi.org/10.1016/j.cej.2023.147797
    7. Huihui Gao, Xiankun Wu, Yaowen Hu, Mang Wu, Wei Liu, Zhongkai Wang. The conversion of woody oils into E-octadec-9-enedioic acid and multiple-shape memory polyamides. Industrial Crops and Products 2023, 191 , 115879. https://doi.org/10.1016/j.indcrop.2022.115879
    8. Muhammad Safder, Muhammad Arshad, Feral Temelli, Aman Ullah. Bio-composites from spent hen derived lipids grafted on CNC and reinforced with nanoclay. Carbohydrate Polymers 2022, 281 , 119082. https://doi.org/10.1016/j.carbpol.2021.119082
    9. Alessandro Gandini, Talita M. Lacerda. Polymers from Renewable Resources: Macromolecular Materials for the Twenty‐First Century?. 2022, 1-79. https://doi.org/10.1002/9783527815562.mme0019
    10. Qinan Zhang, Mengze Song, Yanyan Xu, Wencai Wang, Zhao Wang, Liqun Zhang. Bio-based polyesters: Recent progress and future prospects. Progress in Polymer Science 2021, 120 , 101430. https://doi.org/10.1016/j.progpolymsci.2021.101430
    11. Muhammad Zubair, Rehan Ali Pradhan, Muhammad Arshad, Aman Ullah. Recent Advances in Lipid Derived Bio‐Based Materials for Food Packaging Applications. Macromolecular Materials and Engineering 2021, 306 (7) https://doi.org/10.1002/mame.202000799
    12. . Biomass as a Source of Energy, Fuels and Chemicals. 2021, 589-741. https://doi.org/10.1039/BK9781788012058-00589
    13. Z. M. Zulfattah, N. W. M. Zulkifli, H. H. Masjuki, M. H. Harith, A. Z. Syahir, I. Norain, M. N. A. M. Yusoff, M. Jamshaid, A. Arslan. Friction and Wear Performance of Oleate-Based Esters With Two-, Three-, and Four-Branched Molecular Structure in Pure Form and Mixture. Journal of Tribology 2021, 143 (1) https://doi.org/10.1115/1.4047584
    14. James W. Herndon. The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2017. Coordination Chemistry Reviews 2018, 377 , 86-190. https://doi.org/10.1016/j.ccr.2018.08.007

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