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Issue 20, 2014
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High-density biosynthetic fuels: the intersection of heterogeneous catalysis and metabolic engineering

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Abstract

Biosynthetic valencene, premnaspirodiene, and natural caryophyllene were hydrogenated and evaluated as high performance fuels. The parent sesquiterpenes were then isomerized to complex mixtures of hydrocarbons with the heterogeneous acid catalyst Nafion SAC-13. High density fuels with net heats of combustion ranging from 133–141 000 Btu gal−1, or up to 13% higher than commercial jet fuel could be generated by this approach. The products of caryophyllene isomerization were primarily tricyclic hydrocarbons which after hydrogenation increased the fuel density by 6%. The isomerization of valencene and premnaspirodiene also generated a variety of sesquiterpenes, but in both cases the dominant product was δ-selinene. Ab initio calculations were conducted to determine the total electronic energies for the reactants and products. In all cases the results were in excellent agreement with the experimental distribution of isomers. The cetane numbers for the sesquiterpane fuels ranged from 20–32 and were highly dependent on the isomer distribution. Specific distillation cuts may have the potential to act as high density diesel fuels, while use of these hydrocarbons as additives to jet fuel will increase the range and/or time of flight of aircraft. In addition to the ability to generate high performance renewable fuels, the powerful combination of metabolic engineering and heterogeneous catalysis will allow for the preparation of a variety of sesquiterpenes with potential for pharmaceutical, flavor, and fragrance applications.

Graphical abstract: High-density biosynthetic fuels: the intersection of heterogeneous catalysis and metabolic engineering

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Supplementary files

Article information


Submitted
19 Dec 2013
Accepted
31 Mar 2014
First published
31 Mar 2014

Phys. Chem. Chem. Phys., 2014,16, 9448-9457
Article type
Paper
Author version available

High-density biosynthetic fuels: the intersection of heterogeneous catalysis and metabolic engineering

B. G. Harvey, H. A. Meylemans, R. V. Gough, R. L. Quintana, M. D. Garrison and T. J. Bruno, Phys. Chem. Chem. Phys., 2014, 16, 9448
DOI: 10.1039/C3CP55349C

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