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Synthesis of Fully Biobased Polyesters from Plant Oil
journal contribution
posted on 2017-09-14, 00:00 authored by Liejiang Jin, Keyu Geng, Muhammad Arshad, Reza Ahmadi, Aman UllahSelf-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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Keywords
DMAdegradation temperatureHG 2microwave reactorchromatographyGPCGCFAMEacid methyl estersmicrowave irradiationgravimetric analysisFTIRnonrenewable polyesters337 kDaDSCheatinggeneration catalystscanning calorimetryBiobased Polyestersequilibrium mixturesolvent-free conditionsdiolSelf-metathesis productsdiesterNMRspectroscopyPlant Oil Self-metathesisTGACondensation polymerizationoleic aciddimethyl -9-octadecene
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