Efficient synthesis of high-density aviation biofuel via solvent-free aldol condensation of cyclic ketones and furanic aldehydes

Deng, Qiang; Xu, Jisheng; Han, Peijuan; Pan, Lun; Wang, Li; Zhang, Xiangwen; Zou, Ji‐Jun

doi:10.1016/j.fuproc.2016.03.016

Cited by 113 publications

(89 citation statements)

References 36 publications

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“…[18][19][20] After separation from the reaction mixture,t his solid product was dissolvedi ne xcessive benzene and analyzed by GC-MS whichp roved that it consisted mainly of F 2 CH. This choice was dictated by the formation of ay ellow solid product in experiments with high furfural content.…”

Section: Aldol Condensation Of Furfural and Cyclohexanonementioning

confidence: 99%

“…[31,32] Furthermore, some biomass-derived compounds,s uch as terpenes, have cyclic aliphatic rings and can be directly used as high-density biofuel additives. tion of cyclic ketones with furanics in presence of NaOH as a basic catalysti ns olvent-free [18] or aqueous solutions [19] followed by hydrogenation of produced compounds [18] have been recently shown to be ap romising way to obtain alkylated naphthenic compounds.N aOH was demonstrated [18] to be av ery good catalysti ns olvent-free condensation of cyclopentanone/cyclohexanone andf urfural/5-hydroxymethyl-furfural, whereas Mg(OH) 2 ,C a(OH) 2 ,a nd Na 2 CO 3 weren early inactive (with conversion < 2.0 %). [27] Aldol condensa-This study presentsr esults on aldol condensation of furfural and cyclohexanone in presence of Mg-Al hydrotalcite-derived materials as solid basic catalysts at reaction temperatures from 25 to 90 8Ca nd ac yclohexanonet of urfural molar ratio of 1-10.…”

Section: Introductionmentioning

confidence: 99%

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Using Mg‐Al Mixed Oxide and Reconstructed Hydrotalcite as Basic Catalysts for Aldol Condensation of Furfural and Cyclohexanone

et al. 2018

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This study presents results on aldol condensation of furfural and cyclohexanone in presence of Mg‐Al hydrotalcite‐derived materials as solid basic catalysts at reaction temperatures from 25 to 90 °C and a cyclohexanone to furfural molar ratio of 1–10. Mg‐Al mixed oxide exhibited reasonable activity with furfural conversion of ca. 50 % after 180 min of the reaction at T=90 °C. The activity of reconstructed hydrotalcite was much higher with furfural conversion close to 100 % at short reaction times. In comparison with Mg‐Al mixed oxide, the initial reaction rate has increased 30–50 times. Under similar reaction conditions, cyclohexanone self‐condensation on HTC‐derived catalysts could not compete with aldol condensation because the former reaction was inhibited by produced water. The change in CH/F molar ratio influenced both furfural conversion and product selectivity; higher furfural content in the reaction mixture favored the second condensation step.

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Section: Aldol Condensation Of Furfural and Cyclohexanonementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Using Mg‐Al Mixed Oxide and Reconstructed Hydrotalcite as Basic Catalysts for Aldol Condensation of Furfural and Cyclohexanone

et al. 2018

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“…Cyclohexanone is another potential biofuel of interest derived from lignin. [25,26] Compared to CPO, CXO can produce hydrocarbons with higher energy densities through a hydroxyalkylation/alkylation process with 2-methylfuran, such as pentylcyclohexane and naphthene. [27] It can also be converted to bi-cyclic fuels, like bi-cyclohexane, through self-aldol condensation followed by hydrodeoxygenation.…”

Section: Introductionmentioning

confidence: 99%

Absolute photoionization cross sections of two cyclic ketones: cyclopentanone and cyclohexanone

2017

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Absolute photoionization cross sections for cyclopentanone and cyclohexanone, as well as partial ionization cross sections for the dissociative ionized fragments, are presented in this investigation. Experiments are performed via a multiplexed photoionization mass spectrometer utilizing vacuum ultraviolet (VUV) synchrotron radiation supplied by the Advanced Light Source of Lawrence Berkeley National Laboratory. These results allow the quantification of these species that is relevant to investigate the kinetics and combustion reactions of potential biofuels. The CBS-QB3 calculated values for the adiabatic ionization energies agree well with the experimental values, and the identification of possible dissociative fragments is discussed for both systems. Copyright © 2017 John Wiley & Sons, Ltd.

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“…Deng et al . reported selectivities higher than 85% (in solid phase) after 2 h but working in solvent‐free condensation and using NaOH as catalyst …”

Section: Introductionmentioning

confidence: 99%

“…Hronec et al studied this reaction using homogeneous catalyst (NaOH), with more than 95% of the second adduct yield (C15) in less than 2 h. 13 Deng et al reported selectivities higher than 85% (in solid phase) after 2 h but working in solvent-free condensation and using NaOH as catalyst. 14 In spite of the well-known disadvantages of using homogeneous catalysts, 15 and the wide use of solid base catalysts for these reactions 7,16,17 there are few works dealing with the heterogeneously catalyzed cyclopentanone-furfural condensation. 18 In our previous work, preliminary results using Mg-Zr mixed oxide as catalyst were reported, combining mild conditions (303-323 K) and aqueous media.…”

Section: Introductionmentioning

confidence: 99%

Enhancement of furfural–cyclopentanone aldol condensation using binary water–ethanol mixtures as solvent

Cueto

Faba

Dı́az

et al. 2018

J of Chemical Tech & Biotech

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BACKGROUND Cyclopentanone (CPO) – furfural (FFL) aldol condensation is a very interesting reaction for upgrading the furfural obtained in the depolymerization – dehydration reaction of cellulosic materials. Reaction is faster with cyclopentanone than with other ketones, and resulting condensation adducts are attractive for manufacturing drop‐in fuels. However, the most important problem is that these adducts present low water solubility. RESULTS Binary systems combining water (needed to promote aldol condensation) and ethanol (for enhancing the condensation adducts solubility) at different ratios have been tested. Operation parameters, such as water/ethanol ratio, temperature and reaction time, were optimized for this reaction. Best results (global yield to condensation adducts higher than 36%) were achieved using 1:2 water/ethanol ratio, and working at 303 K. Higher water ratios lead to the precipitation of condensation products, whereas higher ethanol concentrations hinder the catalyst performance. A reaction mechanism, considering a first‐order kinetic model on cyclopentanone concentration, was proposed. Kinetic constants have been empirically correlated with ethanol concentration in the reaction medium. CONCLUSIONS The use of binary ethanol–water binary mixtures with controlled solvent ratios can avoid the precipitation of condensation adducts. This precipitation leads to important operation problems in the reactor as well as to catalyst deactivation. The negative effect of the presence of ethanol on the reaction kinetics can be overcome by increasing reaction temperature. © 2017 Society of Chemical Industry

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Efficient synthesis of high-density aviation biofuel via solvent-free aldol condensation of cyclic ketones and furanic aldehydes

Cited by 113 publications

References 36 publications

Using Mg‐Al Mixed Oxide and Reconstructed Hydrotalcite as Basic Catalysts for Aldol Condensation of Furfural and Cyclohexanone

Using Mg‐Al Mixed Oxide and Reconstructed Hydrotalcite as Basic Catalysts for Aldol Condensation of Furfural and Cyclohexanone

Absolute photoionization cross sections of two cyclic ketones: cyclopentanone and cyclohexanone

Enhancement of furfural–cyclopentanone aldol condensation using binary water–ethanol mixtures as solvent

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