Synthesis of renewable diesel with hydroxyacetone and 2-methyl-furan

Li, Guangyi; Li, Ning; Li, Shanshan; Wang, Aiqin; Ye, Cong; Wang, Xiaodong; Zhang, Tao

doi:10.1039/c3cc42296h

Cited by 124 publications

(79 citation statements)

References 25 publications

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“…Then, the glucoses must be further dehydrated or isomerized to a wide spectrum of platform chemicals, 8,[13][14][15][16] among which 2-methylfuran (2MF) and butanal have recently attracted interests. [17][18][19] Recent research by Corma et al has demonstrated a promising multi-step technique for producing long-chain hydrocarbons from 2-methylfuran (2MF) and butanal with high activity. 20 First, Amberlyst-15 is used as an acid catalyst in a liquid-phase batch reaction to hydroalkylate 2MF with butanal into 1,1-bisylvylalkanes, which are then separated from 2MF, butanal and water (side product).…”

Section: -3mentioning

confidence: 99%

One-step production of long-chain hydrocarbons from waste-biomass-derived chemicals using bi-functional heterogeneous catalysts

Wen

Barrow

Hattrick‐Simpers

et al. 2014

Phys. Chem. Chem. Phys.

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In this study, we demonstrate the production of long-chain hydrocarbons (C 8+ ) from 2-methylfuran (2MF) and butanal in a single step reactive process by utilizing a bi-functional catalyst with both acid and metallic sites. Our approach utilizes a solid acid for the hydroalkylation function and as a support as well as a transition metal as hydrodeoxygenation catalyst. A series of solid acids was screened, among which MCM-41 demonstrated the best combination of activity and stability. Platinum nanoparticles were then incorporated into the MCM-41. The Pt/MCM-41 catalyst showed 96% yield for C 8+ hydrocarbons and the catalytic performance was stable over four reaction cycles of 20 hour each. The reaction pathways for the production of long-chain hydrocarbons is probed with a combination of infrared spectroscopy and steady-state reaction experiments. It is proposed that 2MF and butanal go through hydroalkylation first on the acid site followed by hydrodeoxygenation to produce the hydrocarbon fuels.

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Section: -3mentioning

confidence: 99%

One-step production of long-chain hydrocarbons from waste-biomass-derived chemicals using bi-functional heterogeneous catalysts

Wen

Barrow

Hattrick‐Simpers

et al. 2014

Phys. Chem. Chem. Phys.

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“…Among these base catalysts, KOH showed superior performance in this process by obtaining the highest condensation product yield of 56%. Meanwhile, using Na 2 CO 3 , Ca(OH) 2 and Ba(OH) 2 as the catalysts, both of the EL and FA conversion, and the yield of condensation product yield were significantly reduced. The sequence of activities for the base catalysts decreased in the order of KOH>NaOH>LiOH>Ca(OH) 2 >Ba(OH) 2 >Na 2 CO 3 .…”

Section: Synthesis Of Renewable Jet Fuel Precursors From C-c Bond Conmentioning

confidence: 98%

“…Materials FA (≥99.5%, analytical reagent) was purchased from Tianjin Damao Chemical Reagents Factory. EL (≥99.5%, analytical reagent) and 5%Pd/C catalysts were purchased from Aladdin industrial Co. Ltd. Methanol (≥99.5%, analytical reagent) was purchased from Tianjin Fuyu Fine Chemical Co. Ltd. KOH, NaOH, LiOH, Ba(OH) 2 , Ca(OH) 2 and Na 2 CO 3 were purchased from Tianjin Fuchen Chemical Reagents Factory. All of these materials were used as received.…”

Section: Methodsmentioning

confidence: 99%

“…With continuous depletion of fossil resources and environmental problems of increasing concern, the production of clean and renewable hydrocarbon fuels has drawn considerable attention [1][2][3]. Jet fuel composed of branched long chain alkanes is an important part of today's energy chart, but its production is mainly dependent on nonrenewable fossil energy.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Renewable Jet Fuel Precursors from C-C Bond Condensation of Furfural and Ethyl Levulinate in Water

Cai¹,

Liu²,

Tan³

et al. 2016

Korean Chemical Engineering Research

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− Biomass derived jet fuel is proven as a potential alternative for the currently used fossil oriented energy. The efficient production of jet fuel precursor with special molecular structure is prerequisite in producing biomass derived jet fuel. We synthesized a new jet fuel precursor containing branched C 15 framework by aldol condensation of furfural (FA) and ethyl levulinate (EL), where the latter of two could be easily produced from lignocellulose by acid catalyzed processes. The highest yield of 56% for target jet fuel precursor could be obtained at the optimal reaction condition (molar ratio of FA/EL of 2, 323 K, 50 min) by using KOH as catalyst. The chemical structure of C 15 precursor was specified as (3E, 5E)-6-(furan-2-yl)-3-(furan-2-ylmethylene)-4-oxohex-5-enoic acid (F 2 E). For stabilization, this yellowish solid precursor was hydrogenated at low temperature to obtain C=C bonds saturated product, and the chemical structure was proposed as 4-oxo-6-(tetrahydrofuran-2-yl)-3-(tetrahydrofuran-2-yl)-methyl hexanoic acid (H-F 2 E). The successful synthesis of the new jet fuel precursors showed the significance that branched jet fuel could be potentially produced from biomass derived FA and EL via fewer steps.

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“…11 Aldol condensations of FF/HMF and/or their derivatives with carbonyl groups like acetone, [12][13][14][15][16] hydroxyacetone, 17 butaldehyde, 18 2-butanone, 19 methyl isobutyl ketone, 20 levulinic acid 11,21,22 and angelica lactone 23 have commonly been conducted to obtain the C 9 -C 16 fuel precursors, but these carbonyl compounds originate from fossil resources or are produced from biomass by multi-step reactions, leading to low efficiency and high cost for the entire synthesis. As an alternative, hydroxyalkylation-alkylation of FF and 2-methylfuran obtained by hydrodeoxygenation of FF was reported to produce C 15 fuel precursors with a branched carbon framework.…”

Section: -4mentioning

confidence: 99%

Production of renewable long-chained cycloalkanes from biomass-derived furfurals and cyclic ketones

et al. 2018

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a Developing renewable long-chain cycloalkanes from lignocellulosic biomass is of significance because it offers huge resource storage, wide applications in aviation/diesel fuels and mitigation of CO 2 emissions.In this paper, cycloalkanes with carbon chain lengths of 13-18 were produced from biomass-derived furfural species (furfural and 5-hydroxymethylfurfural) and cyclic ketones (cyclopentanone and cyclohexanone) via aldol condensation, followed by hydrogenation to saturate the C]C and C]O bonds, and hydrodeoxygenation to remove oxygen atoms. The aldol condensation of the furfural species with cyclic ketones was catalyzed by NaOH and the target condensation intermediates were obtained in yields of more than 90% at room temperature (30 C) with a short reaction time (40 min). By using amorphous zirconium phosphate combined with Pd/C as the catalyst, liquid cycloalkanes were produced at the optimal conditions with a yield of 76%. When the combined solid catalyst was reused, the target products reduced after the second run but the initial yield could be largely recovered by recalcination of the spent zirconium phosphate. Considering that cyclopentanone and cyclohexanone can be easily produced from furfural (originating from hemicellulose) and phenol (originating from lignin), respectively, this condensation has the potential to achieve the integrated conversion of biomassderived cellulose, hemicellulose and lignin to jet fuel and/or diesel additives.

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Synthesis of renewable diesel with hydroxyacetone and 2-methyl-furan

Cited by 124 publications

References 25 publications

One-step production of long-chain hydrocarbons from waste-biomass-derived chemicals using bi-functional heterogeneous catalysts

One-step production of long-chain hydrocarbons from waste-biomass-derived chemicals using bi-functional heterogeneous catalysts

Synthesis of Renewable Jet Fuel Precursors from C-C Bond Condensation of Furfural and Ethyl Levulinate in Water

Production of renewable long-chained cycloalkanes from biomass-derived furfurals and cyclic ketones

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