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.
This
study describes the synthesis and characterization of two
biobased polyamides, PA (DMOD-PXDA) and PA (DMOD-DETA), from dimethyl
9-octadecenedioate and p-xylylenediamine or diethylenetriamine.
The effect of traditional (TH) and microwave heating (MH) on
synthesis conditions, thermal properties, and crystalline structures
of the polyamides was compared. Furthermore, thermomechanical and
mechanical properties of polyamide films were studied. Solid-state
carbon nuclear magnetic resonance spectroscopy and attenuated total
reflectance Fourier transform infrared spectroscopy were used to characterize
the polyamides. All polyamides showed a melting point of around 190
°C with higher melting points for the traditionally polycondensed
ones. Wide-angle X-ray scattering indicated γ-crystals as the
primary crystalline forms produced under microwave heating, whereas
amorphous and α-crystal phases were mainly produced under traditional
heating. Dynamic mechanical analysis showed the highest glass transition
temperature for TH-PA (DMOD-PXDA) at 78 °C. PA (DMOD-PXDA) films
exhibited comparable tensile strengths, but the percent elongation
at break of the TH-PA (DMOD-PXDA) film was higher than
that of the MH-PA (DMOD-PXDA) film. Higher values for tensile
strength and percent elongation at break were also observed for TH-PA
(DMOD-DETA) and MH-PA (DMOD-DETA) films, respectively. These biobased
polyamides have a great potential to be used in different applications
as substitutes for petroleum-based polyamides.
In this study, a new strategy for making biopolyethers from plant oil derived monomer (α-olefin) was developed using microwave irradiation, conditions were optimized and compared with a conventional method.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.