It’s been a busy few months in the Chuck group, with masters students working hard for their M.Eng projects (Well done to all of them, by the way. We wish them all the luck in the future!). We’ve been so busy, that we forgot to let you know about our latest publications: one in the area of C10-12 platform chemical production from the enzymatic upgrading of biogenic furans (published in RSC Green Chemistry), and the other in the area of advanced biofuel (including fuel suitable for aviation) and chemical production via the cross-metathesis of microbial and waste lipids (published in ACS Sustainable Chemistry and Engineering).
Donnelly, J., Müller, C.R., Wiermans, L, Chuck, C.J., and de María, P.D., Upgrading biogenic furans: blended C10–C12 platform chemicals via lyase-catalyzed carboligations and formation of novel C12 – choline chloride-based deep-eutectic-solvents, Green Chemistry 2015,17, 2714-2718. (Link)
Benzaldehyde lyase (BAL) results in an efficient biocatalyst for the umpolung carboligation of furfural, HMF, and mixtures of them, leading to blended C10–C12 platform chemicals. Subsequently, the mixing and gentle heating (<100 °C) of the formed hydroxy-ketone with choline chloride leads to the formation of a novel biomass-derived deep-eutectic-solvent.
Jenkins, R.W., Sargeant, L.A., Whiffin, F.M., Santomauro, F., Kaloudis, D., Mozzanega, P., Bannister, C.D., Baena, S., and Chuck, C.J.*, Cross-Metathesis of Microbial Oils for the Production of Advanced Biofuels and Chemicals. ACS Sustainable Chemistry and Engineering 2015, Just Accepted Manuscript. (Link)
A range of microbial oils were cross-metathesized with ethene using Hoveyda–Grubbs second-generation catalyst. The products formed from the microbial oils were compared to alternative first- and second-generation oils. Upon separation, three separate fractions were produced: an alkene hydrocarbon fraction or aviation fuel fraction (AFF), a shorter-chain triglyceride fraction that upon transesterification was suitable as a road transport fuel (road transport fraction, RTF), and a volatile short-chain alkene fraction (gas phase fraction, GPF). The fuel fractions were purified through distillation and compared to the relevant fuel standards. Though there was variation for the RTF because of the presence of long-chain saturates, all the RTF produced fell within the ASTM standard for biodiesel. The AFF was found to be highly suitable for aviation, falling entirely within the DEF-STAN fuel standard. In addition, the AFF possessed an energy density higher than that of Jet A-1, whereas 1-decene was found to have an oxidative stability higher than that of jet fuel. Finally, the GPF was found to predominantly contain propene, butene, and pentadiene isomers, all of which have application in the polymer industry. With further development, this process could provide the basis for a microbial oil biorefinery for the production of sustainable biofuels and polymer precursors.