Synthesis of Jet Fuel Range Cycloalkanes with Cyclopentanone and Furfural

Abstract

In this work, high-density jet fuel range cycloalkanes were synthesized in high yields (∼80%) by solvent-free aldol condensation of cyclopentanone and furfural followed by hydrodeoxygenation (HDO). Sodium-promoted magnesium−aluminum mixed oxides (Na−MgAlO) exhibited a high catalytic activity in the aldol condensation of cyclopentanone and furfural under a solvent-free condition. Furfural conversion of 99.4% with almost 100% selectivity for 2-(2-furylmethylidene) cyclopentanone and 2,5-bis(2-furylmethylidene) cyclopentanone were obtained over the 5.7%Na−MgAlO catalyst under mild conditions (80 °C, 2 h). The Na−MgAlO catalysts were characterized by multiple technologies, such as N 2 physisorption, powder X-ray diffraction, Fourier transform infrared spectra, and CO 2 temperature-programmed desorption, and so on. It was found that the high catalytic activity for aldol condensation of cyclopentanone and furfural was clearly related to the amount and strength of basicity of Na−MgAlO catalysts. Finally, the condensation products were converted to jet fuel range cycloalkanes by HDO over Pd/C and HZSM-5 catalysts. The density, heating value, and freezing point of the HDO liquid products were 0.83 g/cm 3 , 43.1 MJ/Kg, and −27.7 °C, respectively. The results suggest that these cycloalkanes are promising as blending components for jet fuel.

Green Carbon Science: Efficient Carbon Resource Processing, Utilization, and Recycling towards Carbon Neutrality

“…[165] Besides these routes,s ome other protocols have been also developed for the conversion of furfural. Fore xample, furfurylamine, [166] cyclopentanone/cyclopentanol, [167] and fuel or fuel precursors, [168] have been successfully synthesized from furfural through different routes.Anattractive approach has been developed to convert furfural into renewable metaxylylenediamine through aD iels-Alder/aromatization sequence. [169] Very recently,u tilization of furfural to synthesize pyrrole and D-proline has been realized, which is an emerging route for furfural conversion.…”

Biomass-derived 2-methyltetrahydrofuran platform: a focus on precious and non-precious metal-based catalysts for the biorefinery

“…As a vital biomass platform chemical, furfural serves as the central substrate for the formation of various chemicals and fuels. [88][89][90] Hydrogenation and successive hydrogenation of furfural produce furfuryl alcohol and tetrahydrofurfuryl alcohol, respectively. MTHF is formed by the dehydration of furfuryl alcohol to form 2-MF, followed by hydrogenation.…”

Selective production of bicyclic alkanes as high-density fuel additives by coupling lignocellulose-derived furanics and phenolics

“…3,7 Production of biobased fuels from biomass has been widely investigated over the past decades. [8][9][10][11][12][13] Among the production processes, extending the carbon chain number of C5/C6 carbohydrate derivatives is a crucial step in producing high-quality liquid fuels. Aldol condensation, hydroalkylation/alkylation, oligomerization, ketonization, Diels-Alder reaction, Guerbet reaction, and acylation are feasible methods to increase the length of carbon chains or the number of carbon atoms.…”