skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Synthesis of aviation fuel from bio-derived isophorone


Using photochemical [2 + 2] cycloaddition, a cyclobutane dione was generated from isophorone, a condensate of bio-acetone.

 [1]; ORCiD logo [1];  [2];  [2]; ORCiD logo [1];  [3]; ORCiD logo [3];  [3]; ORCiD logo [1]
  1. Chemistry Division, Los Alamos National Laboratory, Los Alamos, USA
  2. Material Physics and Applications Division, Los Alamos National Laboratory, Los Alamos, USA
  3. Department of Chemical and Environmental Engineering, Yale University, New Haven, USA
Publication Date:
Sponsoring Org.:
OSTI Identifier:
Grant/Contract Number:  
89233218CNA000001; EE0007983
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Sustainable Energy & Fuels
Additional Journal Information:
Journal Name: Sustainable Energy & Fuels Journal Volume: 4 Journal Issue: 3; Journal ID: ISSN 2398-4902
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom

Citation Formats

Ryan, Courtney Ford, Moore, Cameron M., Leal, Juan H., Semelsberger, Troy A., Banh, Jenny K., Zhu, Junqing, McEnally, Charles S., Pfefferle, Lisa D., and Sutton, Andrew D. Synthesis of aviation fuel from bio-derived isophorone. United Kingdom: N. p., 2020. Web. doi:10.1039/C9SE01014A.
Ryan, Courtney Ford, Moore, Cameron M., Leal, Juan H., Semelsberger, Troy A., Banh, Jenny K., Zhu, Junqing, McEnally, Charles S., Pfefferle, Lisa D., & Sutton, Andrew D. Synthesis of aviation fuel from bio-derived isophorone. United Kingdom. doi:
Ryan, Courtney Ford, Moore, Cameron M., Leal, Juan H., Semelsberger, Troy A., Banh, Jenny K., Zhu, Junqing, McEnally, Charles S., Pfefferle, Lisa D., and Sutton, Andrew D. Tue . "Synthesis of aviation fuel from bio-derived isophorone". United Kingdom. doi:
title = {Synthesis of aviation fuel from bio-derived isophorone},
author = {Ryan, Courtney Ford and Moore, Cameron M. and Leal, Juan H. and Semelsberger, Troy A. and Banh, Jenny K. and Zhu, Junqing and McEnally, Charles S. and Pfefferle, Lisa D. and Sutton, Andrew D.},
abstractNote = {Using photochemical [2 + 2] cycloaddition, a cyclobutane dione was generated from isophorone, a condensate of bio-acetone.},
doi = {10.1039/C9SE01014A},
journal = {Sustainable Energy & Fuels},
number = 3,
volume = 4,
place = {United Kingdom},
year = {2020},
month = {3}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 2 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Calcium‐Based Sustainable Chemical Technologies for Total Carbon Recycling
journal, April 2019

  • Rodygin, Konstantin S.; Vikenteva, Yulia A.; Ananikov, Valentine P.
  • ChemSusChem, Vol. 12, Issue 8
  • DOI: 10.1002/cssc.201802412

Experiment studies on the effect of altitude on Jet A's flash point: EFFECT OF ALTITUDE ON JET A'S FLASH POINT
journal, July 2012

  • Tang, Yanfei; Niu, Yi; Yin, Lei
  • Fire and Materials, Vol. 37, Issue 6
  • DOI: 10.1002/fam.2141

Sooting tendencies of co-optima test gasolines and their surrogates
journal, January 2019

  • McEnally, Charles S.; Xuan, Yuan; St. John, Peter C.
  • Proceedings of the Combustion Institute, Vol. 37, Issue 1
  • DOI: 10.1016/j.proci.2018.05.071

Sooting characteristics of surrogates for jet fuels
journal, June 2010

Acetone-butanol fermentation revisited.
journal, January 1986

Chemical and photechemical reactivity in micellar media and microemulsions IV: concentration effects on isophorone dimerization
journal, January 1982

  • Sakellariou-Fargues, Reine; Maurette, Marie-Thérèse; Oliveros, Esther
  • Journal of Photochemistry, Vol. 18, Issue 2
  • DOI: 10.1016/0047-2670(82)80012-9

Comparison of PM Emissions from a Commercial Jet Engine Burning Conventional, Biomass, and Fischer–Tropsch Fuels
journal, December 2011

  • Lobo, Prem; Hagen, Donald E.; Whitefield, Philip D.
  • Environmental Science & Technology, Vol. 45, Issue 24
  • DOI: 10.1021/es201902e

Overview of the National Jet Fuels Combustion Program
journal, April 2017

  • Colket, Meredith; Heyne, Joshua; Rumizen, Mark
  • AIAA Journal, Vol. 55, Issue 4
  • DOI: 10.2514/1.J055361

Photocycloaddition Reactions of 5,5-Dimethyl-3-(3-methylbut-3-en-1-ynyl)cyclohex-2-en-1-one
journal, March 2008

  • Inhülsen, Inga; Kopf, Jürgen; Margaretha, Paul
  • Helvetica Chimica Acta, Vol. 91, Issue 3
  • DOI: 10.1002/hlca.200890044

Sooting behavior in temperature-controlled laminar diffusion flames
journal, October 1984

Biofuel blending reduces particle emissions from aircraft engines at cruise conditions
journal, March 2017

  • Moore, Richard H.; Thornhill, Kenneth L.; Weinzierl, Bernadett
  • Nature, Vol. 543, Issue 7645
  • DOI: 10.1038/nature21420

How do liquid fuel physical properties affect liquid jet development in atomisers?
journal, October 2016

  • Charalampous, Georgios; Hardalupas, Yannis
  • Physics of Fluids, Vol. 28, Issue 10
  • DOI: 10.1063/1.4965447

Novel pathways for fuels and lubricants from biomass optimized using life-cycle greenhouse gas assessment
journal, June 2015

  • Balakrishnan, Madhesan; Sacia, Eric R.; Sreekumar, Sanil
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 25
  • DOI: 10.1073/pnas.1508274112

One hundred years of clostridial butanol fermentation
journal, January 2016

High‐Performance Jet Fuels Derived from Bio‐Based Alkenes by Iron‐Catalyzed [2+2] Cycloaddition
journal, March 2019

  • Morris, David M.; Quintana, Roxanne L.; Harvey, Benjamin G.
  • ChemSusChem, Vol. 12, Issue 8
  • DOI: 10.1002/cssc.201802588

Supramolecularity and Photodimerization of Isophorone:  FTIR and Molecular Mechanics Studies
journal, February 1998

  • Gonçalves, Huguette; Robinet, Germaine; Barthelat, Michèle
  • The Journal of Physical Chemistry A, Vol. 102, Issue 8
  • DOI: 10.1021/jp9729270

Study on the Pressure Dependence of Boiling Point, Flashpoint, and Lower Flammability Limit at Low Ambient Pressure
journal, February 2015

  • Ding, Chao; He, Yaping; Yin, Jiusheng
  • Industrial & Engineering Chemistry Research, Vol. 54, Issue 6
  • DOI: 10.1021/ie503383a

The Path Forward for Biofuels and Biomaterials
journal, January 2006

  • Ragauskas, Arthur J.; Williams, Charlotte K.; Davison, Brian H.
  • Science, Vol. 311, Issue 5760, p. 484-489
  • DOI: 10.1126/science.1114736

Synthesis of jet fuel rang cycloalkane from isophorone with glycerol as a renewable hydrogen source
journal, December 2017

Review on synthesis and properties of high-energy-density liquid fuels: Hydrocarbons, nanofluids and energetic ionic liquids
journal, April 2018

Production of an acetone-butanol-ethanol mixture from Clostridium acetobutylicum and its conversion to high-value biofuels
journal, February 2015

  • Sreekumar, Sanil; Baer, Zachary C.; Pazhamalai, Anbarasan
  • Nature Protocols, Vol. 10, Issue 3
  • DOI: 10.1038/nprot.2015.029

Performance Assessment of Some Isomers of Saturated Polycyclic Hydrocarbons for Use as Jet Fuels
journal, July 2014

  • Keshavarz, Mohammad Hossein; Monjezi, Khadijeh Hosseini; Esmailpour, Karim
  • Propellants, Explosives, Pyrotechnics, Vol. 40, Issue 2
  • DOI: 10.1002/prep.201400079

Advanced Technology Paths to Global Climate Stability: Energy for a Greenhouse Planet
journal, November 2002

Integration of chemical catalysis with extractive fermentation to produce fuels
journal, November 2012

  • Anbarasan, Pazhamalai; Baer, Zachary C.; Sreekumar, Sanil
  • Nature, Vol. 491, Issue 7423, p. 235-239
  • DOI: 10.1038/nature11594

Heterogeneous Ketone Hydrodeoxygenation for the Production of Fuels and Feedstocks from Biomass
journal, April 2017

  • Jenkins, Rhodri W.; Moore, Cameron M.; Semelsberger, Troy A.
  • ChemCatChem, Vol. 9, Issue 14
  • DOI: 10.1002/cctc.201601678

Photodimerization of isophorone in supercritical trifluoromethane and carbon dioxide
journal, March 1989

  • Hrnjez, Bruce J.; Mehta, Anil J.; Fox, Marye Anne
  • Journal of the American Chemical Society, Vol. 111, Issue 7
  • DOI: 10.1021/ja00189a047

CO2 fixation by anaerobic non-photosynthetic mixotrophy for improved carbon conversion
journal, September 2016

  • Jones, Shawn W.; Fast, Alan G.; Carlson, Ellinor D.
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms12800

Efficient Catalysis of Calcium Carbide for the Synthesis of Isophorone from Acetone
journal, April 2016

  • Li, Yingjie; Meng, Hong; Lu, Yingzhou
  • Industrial & Engineering Chemistry Research, Vol. 55, Issue 18
  • DOI: 10.1021/acs.iecr.6b00484

Synthesis of renewable high-density fuel with isophorone
journal, July 2017

Synthesis of Acetone-Derived C 6 , C 9 , and C 12 Carbon Scaffolds for Chemical and Fuel Applications
journal, December 2016

  • Moore, Cameron M.; Jenkins, Rhodri W.; Janicke, Michael T.
  • ChemSusChem, Vol. 9, Issue 24
  • DOI: 10.1002/cssc.201600936

Formulation of a Surrogate for the Simulation of jet fuel pool Fires
journal, April 2005

  • Eddings, Eric G.; Yan, Shihong; Ciro, William
  • Combustion Science and Technology, Vol. 177, Issue 4
  • DOI: 10.1080/00102200590917248

Evaluating Missile Fuels
journal, October 2006

  • Osmont, Antoine; Gökalp, Iskender; Catoire, Laurent
  • Propellants, Explosives, Pyrotechnics, Vol. 31, Issue 5
  • DOI: 10.1002/prep.200600043

High-Density Renewable Fuels Based on the Selective Dimerization of Pinenes
journal, January 2010

  • Harvey, Benjamin G.; Wright, Michael E.; Quintana, Roxanne L.
  • Energy & Fuels, Vol. 24, Issue 1
  • DOI: 10.1021/ef900799c

Effect of copper(I) on cyclic enone photodimerizations
journal, December 1985

  • Fox, Marye Anne; Cardona, Raul; Ranade, Arvind C.
  • The Journal of Organic Chemistry, Vol. 50, Issue 25
  • DOI: 10.1021/jo00225a002

Photoinduced cycloaddition of biomass derivatives to obtain high-performance spiro-fuel
journal, January 2019

  • Xie, Junjian; Pan, Lun; Nie, Genkuo
  • Green Chemistry, Vol. 21, Issue 21
  • DOI: 10.1039/C9GC02790D

Sooting Tendencies of Oxygenated Hydrocarbons in Laboratory-Scale Flames
journal, March 2011

  • McEnally, Charles S.; Pfefferle, Lisa D.
  • Environmental Science & Technology, Vol. 45, Issue 6
  • DOI: 10.1021/es103733q

Synthesis of high-density and low-freezing-point jet fuel using lignocellulose-derived isophorone and furanic aldehydes
journal, January 2018

  • Xie, Jiawei; Zhang, Lei; Zhang, Xiangwen
  • Sustainable Energy & Fuels, Vol. 2, Issue 8
  • DOI: 10.1039/C8SE00197A

Hydrothermal Decarboxylation and Hydrogenation of Fatty Acids over Pt/C
journal, January 2011