ShadowWarrior4444
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2,5-Dimethylfuran (Gasoline Replacement)
I am particularly surprised that there has not been thread on this very useful compound before!
The issue of using 2,5-Dimethylfuran as a gasoline alternative is one that may play a large role in the future energy economy. Recent advances have
allowed its efficient production from glucose and fructose using an acid catalyzed method.
Notable qualities:
Immiscible with water
All current internal combustion engines can use it without modification
40% higher energy density compared to ethanol
Will require +/- no modifications to the current petrol infrastructure
The only issue that seems to be blocking its use is that its toxicity has not been completely evaluated--there are some concerns that in its capacity
as a metabolite of hexane, it plays a role in the neurotoxicity of said compound.
Note: http://en.wikipedia.org/wiki/Dimethylfuran
A practical lab synth of DMF would be appreciated; my cursory digging around has not yielded much in the way of a concrete procedure. Patent searches
have yielded +/- nothing as well.
Salient References:
Haibo Zhao, Johnathan E. Holladay, Heather Brown, Z. Conrad Zhang (June 15). "Metal Chlorides in Ionic Liquid Solvents Convert Sugars to
5-Hydroxymethylfurfural". Science 316 (5831): 1597 - 1600. doi:10.1126/science.1141199
http://www.news.wisc.edu/13881
Yuriy Román-Leshkov, Christopher J. Barrett, Zhen Y. Liu & James A. Dumesic (2007). "Production of dimethylfuran for liquid fuels from
biomass-derived carbohydrates". Nature 447 (7147): 982. doi:10.1038/nature05923
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leu
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Dimethyl furan patents
| Quote: | | Patent searches have yielded +/- nothing as well. |
There's at least one patent concerning dimethyl furan synthesis 
Attachment: GB1021708A.pdf (322kB)
This file has been downloaded 1458 times
Chemistry is our Covalent Bond
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chemrox
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I am *very* interested in this and am appalled that I missed it until tonight. Thank you very much! The wiki article cites some good refs to
follow-up with. The above patent looks pretty brutal. I'm sure PNW labs has a better (bio) route..
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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ShadowWarrior4444
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| Quote: | Originally posted by chemrox
I am *very* interested in this and am appalled that I missed it until tonight. Thank you very much! The wiki article cites some good refs to
follow-up with. The above patent looks pretty brutal. I'm sure PNW labs has a better (bio) route.. |
After reading through the patent, it doesn’t seem all that intensive-- a simplified synth seems to be condensing Acetone with H2SO4 to Mesityl
Oxide, then passing SO2 or O2 through it in the presence of WO2 at 300-700C. This is perhaps the most simplistic embodiment of the patent, though the
only thing that seems to be particularly variable in the entire process is the composition of the catalyst. What did bother me slightly about this
patent is one line:
"The mechanism by which either oxygen of sulfur dioxide works in the catalytic mesityl oxide conversion to dimethyl furan is not certain at this
time, but it is believed that the product obtained is 2,5-dimethyl furan."
This annoyed me for a few reasons, predominantly that they used the word 'believed,' indicating they are not sure that it is
2,5-Dimethylfuran. This alone was troubling, however coupled with the fact that there are other Dimethylfurans, that they are unaware of the mechanism
by which the process works, and that these compounds may or may not be neurotoxic...
My main interest in this compound is the synth from sugars, which it was mentioned takes place via a Hydroxymethylfurfural intermediary. I recall an
article that seemed to indicate that the main difficulty in mass production of DMF from fructose was the intermediary (HMF) could not be easily
converted to DMF. Though the article seemed to indicate that this problem had been somewhat overcome.
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Axt
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Attaching the 100 most relevant abstracts regarding the preparation of dimethylfuran, from scifinder.
Attachment: dimethylfuran preparation scifinder.pdf (218kB)
This file has been downloaded 5841 times
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Klute
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Very interesting topic!
The Dimethylfuran could be used as an additive more than a pur compound, lessening it's (possible) toxicity if mixed with, say vegetable oil or
bioethanol. It would still be more efficient than theses alone I suppose.
Just as a saide note, I would avoid using the acronym "DMF" which usally stands for "Dimethylformamide", a common aprotic polar solvant. We have
enough confusion with acronyms already 
\"You can battle with a demon, you can embrace a demon; what the hell can you do with a fucking spiritual computer?\"
-Alice Parr
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Nicodem
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A related patent: WO2007146636
Attached is the review paper cited by ShadowWarrior4444:
Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates.
Roman-Leshkov, Yuriy; Barrett, Christopher J.; Liu, Zhen Y.; Dumesic, James A.
Nature, 447 (2007) 982-985. DOI: 10.1038/nature05923
[Edited on 10/5/2008 by Nicodem]
Attachment: Production of dimethylfuran for liquid fuels.pdf (294kB)
This file has been downloaded 1842 times
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