Harmonising Production, Properties and Environmental Consequences of Liquid Transport Fuels from Biomass—2,5‐Dimethylfuran as a Case Study

Simmie, John M.; Würmel, Judith

doi:10.1002/cssc.201200738

Cited by 31 publications

(21 citation statements)

References 53 publications

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“…Indeed, DMF has been recognized as a promising fuel additive because of its higher energy density as compared to ethanol (40 % greater), high octane number, and very low solubility in water. The flexibility of the process definitely reinforces its attractiveness for industrial implementation 8…”

Section: Methodsmentioning

confidence: 97%

Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates

et al. 2014

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The one-pot production of industrially valuable diketone derivatives from carbohydrates is achieved through a bifunctional catalytic process. In particular, Pd/C-catalyzed hydrogenation of HMF in water and under CO2 affords 1-hydroxypentane-2,5-dione with up to 77% yield. The process is also eligible starting from fructose and inulin, affording 1-hydroxyhexane-2,5-dione with 36% and 15% yield, respectively. The key of the process is reversible in situ formation of carbonic acid, which is capable of assisting Pd/C during the hydrogenation reaction by promoting the dehydration of carbohydrates and the ring-opening of furanic intermediates. Interestingly, by changing the reaction medium from H2 O to a H2 O/THF mixture (1:9), it is possible to switch the selectivity of the reaction and to produce 2,5-hexanadione with 83% yield. Within the framework of sustainable chemistry, reactions presented in this report show 100% carbon economy, involve CO2 to generate acidity, require water as a solvent, and are conducted under rather low hydrogen pressures (10 bar).

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Section: Methodsmentioning

confidence: 97%

Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates

et al. 2014

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“…With a resurgent interest in the synthesis of platform chemicals and biofuels from nonedible biomass and since the properties and gas‐phase pyrolytic/oxidation chemistries of furans have been the subject of much recent work , we have undertaken a study of this compound.…”

Section: Introductionmentioning

confidence: 99%

A Quantum Chemical Study of the Abnormal Reactivity of 2‐Methoxyfuran

Simmie

Somers

Yasunaga

et al. 2013

Int J of Chemical Kinetics

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The gas-phase pyrolytic and oxidative chemistry of furans has received much attention recently because of their potential as platform chemicals and biofuels. Typically these compounds exhibit very strong ring carbon to H or CH 3 bonds. 2-Methoxyfuran had been reported to be exceptionally unstable in comparison to related substituted heterocycles in pyrolytic experiments. The origins of its reactivity are shown to be due to the very weak O-CH 3 , which at 189.5 ± 1.9 kJ mol −1 is some 200 kJ mol −1 weaker than C-H bonds in the molecule. We show that the reported reactivity is somewhat overestimated but that does not alter the fact that 2-methoxyfuran is exceptionally unstable. It may prove to be a useful alternative to azomethane as a thermal source of methyl radicals. C

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“…As a chemical that can be produced from biomass, 2,5-dimethylfuran (DMF) is suitable as a biofuel, with properties similar to those of gasoline (Roman-Leshkov et al, 2007;Simmie and Wurmel, 2013). Early studies on the thermal decomposition of furan series biofuels were reported by Grela et al (1985) and Lifshitz et al (1986Lifshitz et al ( , 1997Lifshitz et al ( , 1998.…”

Section: Introductionmentioning

confidence: 98%

Primary Combustion Intermediates in Low-Pressure Premixed Laminar 2,5-Dimethylfuran/Oxygen/Argon Flames

Wei

Tong

et al. 2014

Combustion Science and Technology

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Primary combustion intermediates in low-pressure premixed laminar 2,5-dimethylfuran (DMF)/oxygen (O 2 /argon (Ar) flames with equivalence ratios of 0.8 and 1.5 were investigated by using tunable synchrotron vacuum ultraviolet photoionization and molecular-beam mass spectrometry. DMF is a promising biofuel, with properties similar to those of gasoline. However, the combustion chemistry of DMF is not well-studied. Possible reaction pathways of DMF and its primary combustion derivatives were proposed based on the combustion intermediates identified in this work. Photoionization efficiency curves (PIEs) of the combustion intermediates in the DMF/O 2 /Ar flames were recorded. Ionization energies (IEs) were measured from the PIEs. The combustion intermediates were identified by the agreement of the measured IEs with those reported in the literatures or calculated at G3B3 level. H abstraction and the consecutive reaction products were identified, including 5-methylfurfural, (Z)-1-oxo-1,3,4-pentatriene, and 2-ethyl-5-methylfuran, etc. Furan was not observed in the low-pressure DMF flames. H and OH addition products were also identified, including 2-methylfuran, (2Z,3E)-1-oxo-1,3-pentadiene, and 2-oxo-2,3-dihydro-5-methylfuran. The extra methyl side chain may explain the lower laminar burning velocity of DMF relative to that of 2-methylfuran.

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Harmonising Production, Properties and Environmental Consequences of Liquid Transport Fuels from Biomass—2,5‐Dimethylfuran as a Case Study

Cited by 31 publications

References 53 publications

Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates

Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates

A Quantum Chemical Study of the Abnormal Reactivity of 2‐Methoxyfuran

Primary Combustion Intermediates in Low-Pressure Premixed Laminar 2,5-Dimethylfuran/Oxygen/Argon Flames

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