Production of Jet Fuel Range Hydrocarbons as a Coproduct of Algal Biodiesel by Butenolysis of Long-Chain Alkenones
Abstract
Long-chain (35–40 carbons) alkenones are a unique class of lipids biosynthesized by certain species of algae including the industrially grown marine microalgae Isochrysis . Their structures are characterized by a very long linear carbon-chain with trans double bonds and a methyl or ethyl ketone. A method is presented for the isolation of pure alkenones from Isochrysis biomass in parallel with biodiesel production. Yields for the isolated alkenones and biodiesel relative to the starting dry Isochrysis biomass were routinely 3.5 and 12% (w/w), respectively. Alkenones were then converted to smaller hydrocarbon fragments (jet-fuel range) by cross-metathesis with 2-butene (butenolysis) using several commercial ruthenium-based metathesis initiators. Butenolysis with the second-generation Hoveyda-Grubbs catalyst occurred rapidly at 4 °C, yielding near quantitative conversion within 30 min to a mixture containing mostly 8-decen-2-one (C 10 ), 2,9-undecadiene (C 12 ), and 2-heptadecene (C 17 ) as both cis - and trans isomers based on analysis by comprehensive two-dimensional gas chromatography.
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Butenolysis of alkenones using 2-butene generated fuel jet range hydrocarbons principally 2,9-undecane (43%), 2-heptadecene (28%) and 8-decen-2-one (12%) as a mixture of cis and trans isomers.
“Subsequent butenolysis of the alkenones (using 2-butene) generated a range of fuel jet range hydrocarbons principally, 2,9-undecane (43%), 2-heptadecene (28%) and 8-decen-2-one (12%) as a mixture of cis and trans isomers (Figure 13) [80].”
From Key Targets for Improving Algal Biofuel Production (2021) · cites this paper as [80]
Alkenones can be separated from fatty acids by a saponification-based method.
“Alkenones can be separated from fatty acids by a saponificationbased method [80].”
From Key Targets for Improving Algal Biofuel Production (2021) · cites this paper as [80]
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da Costa, F., Le Grand, F., Quéré, C., Bougaran, G., Cadoret, J. P., Robert, R., & Soudant, P. (2017) · Algal Research · doi:10.1016/j.algal.2017.09.003 · Cited by 64 · see citing works
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- Authors
- O’Neil, G. W., Culler, A. R., Williams, J. R., Burlow, N. P., Gilbert, G. J., Carmichael, C. A., Nelson, R. K., Swarthout, R. F., & Reddy, C. M.
- Affiliations
- Western Washington University (US)
- Woods Hole Oceanographic Institution (US)
- Corresponding author
- O’Neil, Gregory W.
- ORCID
- Venue
- Energy & Fuels
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-01-21
- Volume
- 29
- Issue
- 2
- Pages
- 922-930
- ISSN
- 0887-0624 (ISSN-L)
- 1520-5029
- OpenAlex
- W2006247701
- Cited by
- 35
- References
- 62
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 3 · 2023: 1 · 2022: 2 · 2021: 4 · 2020: 2 · 2019: 4 · 2018: 6 · 2017: 3 · 2016: 7 · 2015: 1
- FWCI
- 1.68
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Energy & Fuels (publishedVersion)
- Funders
- Division of Chemistry (CHE-1151492)
- Topics
- Physical Sciences › Energy › Renewable Energy, Sustainability and the Environment › Algal biology and biofuel production
- Physical Sciences › Chemistry › Organic Chemistry › Synthetic Organic Chemistry Methods
- Physical Sciences › Engineering › Mechanical Engineering › Catalysis and Hydrodesulfurization Studies
- Keywords
- alkenones, jet fuel, algal biodiesel, Isochrysis, cross-metathesis, 2-butene, Hoveyda-Grubbs catalyst, marine microalgae
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