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Author: Subject: 2,5-Dimethylfuran (Gasoline Replacement)
ShadowWarrior4444
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[*] posted on 9-5-2008 at 15:59
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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[*] posted on 9-5-2008 at 17:25
Dimethyl furan patents


Quote:
Patent searches have yielded +/- nothing as well.


There's at least one patent concerning dimethyl furan synthesis :P

Attachment: GB1021708A.pdf (322kB)
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chemrox
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[*] posted on 9-5-2008 at 23:03


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..



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ShadowWarrior4444
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[*] posted on 9-5-2008 at 23:40


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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[*] posted on 9-5-2008 at 23:56


Attaching the 100 most relevant abstracts regarding the preparation of dimethylfuran, from scifinder.

Attachment: dimethylfuran preparation scifinder.pdf (218kB)
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[*] posted on 10-5-2008 at 01:50


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 :)




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[*] posted on 10-5-2008 at 05:03


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)
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