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

Xie, Jiawei; Zhang, Lei; Zhang, Xiangwen; Han, Peijuan; Xie, Junjian; Pan, Lun; Zou, De-Rong; Liu, Songhua; Zou, Ji‐Jun

doi:10.1039/c8se00197a

Cited by 43 publications

(13 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several reactions are catalyzed by homogeneous and heterogeneous bases, including aldol condensation [1][2][3][4] and transesterification for product of biodiesel [5]. Aldol condensation is used for synthesis of various products ranging from basic and specialty chemicals to fragrances, flavours and pharmaceuticals [1][2][3][4][5]. Conventionally aldol condensation is performed using homogeneous catalysts [6,7], such as sodium or potassium hydroxide or Ti(O-t-Bu) 4 as catalysts [7].…”

Section: List Of Symbolsmentioning

confidence: 99%

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

et al. 2019

View full text Add to dashboard Cite

Kinetics of the cross aldol condensation of valeraldehyde with cyclopentanone was investigated in a batch reactor under atmospheric pressure at 130 °C using heterogeneous metal modified oxides, such as CeO 2 -MgO, FeO-MgO, FeO-CaO as well as pristine CaO as catalysts. The catalysts were prepared either by evaporation impregnation or deposition precipitation methods and characterized by XRD, TEM, SEM, nitrogen adsorption, ammonia and CO 2 TPD. The results revealed that an optimum amount of strong basic sites gives the highest ratio between cross condensation and self-condensation products of valeraldehyde. The highest yield of the desired product 2-pentylidenecyclopentanone (66%) was obtained with FeO-MgO prepared by the deposition precipitation methods. Graphical AbstractCross-condensation of valeraldehyde with cyclopentanone was investigated over heterogeneous Fe-CaO, CeO-MgO, FeO-CaO and CaO catalysts at 130 °C using cyclopentanone as a solvent and reactant. The highest yield of the desired product, 2-pentylidene-cyclopentanone, finding applications as fragrances, flavours and pharmaceuticals, was 66% obtained over FeO-MgO catalyst exhibiting both acid and basic sites.

show abstract

Section: List Of Symbolsmentioning

confidence: 99%

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Among them, furfural is a key biomass platform chemically derived from hemicellulose . MO, MIBK, and isophorone can be obtained by the self-condensation/hydrogenation of acetone. ,,, Cyclohexanone can be produced from lignin-derived phenolic compounds by selective hydrogenation. − According to Table , the ball-milling method is active for all investigated condensation reactions. Compared with the magnetic stirring method using NaOH as a catalyst, a competitive yield of products was achieved using heterogeneous CaO as a catalyst under mild temperatures.…”

Section: Results and Discussionmentioning

confidence: 99%

“…25 MO, MIBK, and isophorone can be obtained by the selfcondensation/hydrogenation of acetone. 8,11,26,27 Cyclohexanone can be produced from lignin-derived phenolic compounds by selective hydrogenation. 28−30 According to Table 2, the ball-milling method is active for all investigated condensation reactions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Ball-Milling: A Productive, Economical, and Widely Applicable Method for Condensation of Biomass-Derived Aldehydes and Ketones at Mild Temperatures

Sheng

et al. 2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

For the first time, ball-milling was introduced as an efficient process for the condensation of biomass-derived cyclopentanone using commercial CaO as a catalyst. Compared with traditional magnetic stirring methods ("heat input" methods), ball-milling is an alternative "energy input" method. CaO dosage, rotation speed, and reaction time were investigated for optimal condition screening, and the ball-milling method could achieve a high yield (98.9%) and a high selectivity (99.2%) under lower energy demand conditions at mild temperature (∼40 °C). Moreover, the power hypothetically needed for dimer per mole (E 2 ) of the ball-milling method was comparable or even lower than that for the magnetic stirring method after our assessment. In addition, we also explored the applicability of the ball-milling method for the condensation of other biomass-derived aldehydes and ketones. Competitive yield was obtained using heterogeneous CaO as a catalyst. Due to the intense stirring in ball-milling, the CaO catalyst was mixed uniformly with reactants, and higher surface area was also obtained due to the decrease of the particle size during the ball-milling method, which may also benefit the reaction and increase the catalytic activity. This way would tally with the concept of green chemistry and economic efficiency, which has the potential for industrial applications.

show abstract

“…Xie et al. found that NaOH was an efficient catalyst for the aldol condensation of isophorone and furanic aldehydes [287] . Under solvent‐free, optimized conditions (9.45 mmol NaOH, 70 °C, 0.5 h) excellent conversions of furfural (99.6 %) and isophorone (76.5 %) were observed.…”

Section: Isophoronementioning

confidence: 99%

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Muldoon

Harvey

2020

ChemSusChem

View full text Add to dashboard Cite

David Glueck, with an emphasis on the synthesis of P-stereogenic phosphine ligands for asymmetric catalysis. He is currently a National Research Council (NRC) postdoctoral fellow with Dr. Benjamin Harvey at the Naval Air Warfare Center Weapons Division (NAWCWD) in China Lake, CA, USA. His research interests include the synthesis of small molecules with applications in fuels, materials, and catalysis. Benjamin G. Harvey received his Ph.D. in inorganic chemistry from the University of Utah, USA, in 2005, studying with Professor Richard D. Ernst. He is now a Senior Research Chemist at the Naval Air Warfare Center, Weapons Division located in China Lake, CA. His current research focuses on the utilization of bio-based substrates for the preparation of advanced materials and the development of hybrid synthetic routes that combine chemical catalysis with synthetic biology. Specific interests include advanced alternative fuels for jet, missile, and rocket propulsion, bio-based high-temperature thermosetting resins, biocomposites, lubricants, and green solvents.

show abstract

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

Abstract: Biofuels synthesized from lignocellulose-derived platform chemicals are very attractive for sustainable development.

Cited by 43 publications

References 40 publications

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

Aldol Condensation of Cyclopentanone with Valeraldehyde Over Metal Oxides

Ball-Milling: A Productive, Economical, and Widely Applicable Method for Condensation of Biomass-Derived Aldehydes and Ketones at Mild Temperatures

Bio‐Based Cycloalkanes: The Missing Link to High‐Performance Sustainable Jet Fuels

Contact Info

Product

Resources

About