Production of liquid hydrocarbon fuels with 3-pentanone and platform molecules derived from lignocellulose

Abstract

Diesel or jet fuel range C 10 -C 17 branched and cyclic alkanes were produced by reaction of 3-pentanone derived from lactic acid with bio-based aldehydes through aldol condensation followed by hydrodeoxygenation. DBU (1,8-diazabicycloundec-7-ene) was identified as an efficient catalyst for the aldol reaction of 3-pentanone with furan based aldehydes, and the selectivity of single or double aldol condensation product could be easily controlled by adjusting the reaction temperature. For the reaction with aromatic aldehydes, aluminium phosphate demonstrated a higher catalytic activity than DBU and mechanisms were proposed for the difference in the catalytic activity. The final hydrodeoxygenation step could be achieved by using a simple Pd/C + H-beta zeolite system, excellent selectivity was observed under the present system, the clean formation of hydrocarbons with a narrow distribution of alkanes occurred in most cases.Scheme 1 (a) Previous work versus (b) our new protocol for the synthesis of liquid alkanes using 3-pentanone as a bio-based synthon.This journal is

Production of cyclopentanone from furfural over Ru/C with Al11.6PO23.7 and application in the synthesis of diesel range alkanes

“…This process requires synergistic catalysis between the hydrogenation catalyst and solid acid. Encouraged by our previous work, [45][46][47] we found that the commercial catalyst Pd/C added zeolite (H-beta) had the best selectivity for alkanes. During this experiment, 5% equivalent Pd with 0.5 g H-beta (Si/ Al ¼ 40) to 5 mmol C-C coupling products was used as the catalyst and reacted at 473 K, and water as the solvent and 3 MPa hydrogen pressure were required simultaneously.…”

“…CPO and CPL are versatile chemical intermediates that are applied in various elds of daily life. Inspired by our previous work, [45][46][47] cyclopentanone can be used as a substrate to synthesize diesel range fuels due to its carbonyl group. This process consists of two steps.…”

“…In our previous reports, carbonyl compounds through the C-C coupling reaction consisting of aldol condensation or HAA (hydroxyalkylation and alkylation) reaction with furan-based derivatives were prepared as fuel precursors, which were applied to the synthesis of liquid hydrocarbon fuels through hydrodeoxygenation. [45][46][47] Here, we design a new route for the synthesis of cyclic alkanes for use in diesel range fuels from the hydrogenation product of furfural.…”

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

“…[175,176] EAOAc, was prepared from acetic acid and ethanolamine (a bio-based substrate from cellulose), and displayed the highest activity of the ionic liquids investigated. [177] According to literature reports, [178,179] the hydroxyl group in EAOAc promoted hydrogen bonding between the reactants and catalysts, enhancing the condensation reaction. Free ethanolamine catalyzed the reaction, but higher activity was obtained when the ionic liquid was used.…”

Efficient synthesis of C15fuel precursor by heterogeneously catalyzed aldol-condensation of furfural with cyclopentanone

“…20 Furthermore, methyl isobutyl ketone, 2-pentanone, 2-heptanone and 3-pentanone were successively applied to the aldol condensation with furfural, generating linear or singly branched alkanes aer the later hydrogenation/hydrodeoxygenation. [21][22][23][24] Aldol condensation plays an important role in this fuel synthesis strategy, by which the carbon-chain length of platform molecules can increase. In our view, the choice of the second reactant in the furfural aldol condensation is a crucial step, which almost determines the structure of nal products and fuel quality.…”