I was wondering what the viability of a synthesis of furan and tetrahydrofuran from sucrose was. My idea was to first convert sucrose to
chloromethylfurfural (http://www.orgsyn.org/demo.aspx?prep=CV2P0393) followed by oxidation to furandicarboxylic acid with nitric acid (Fenton 1909), decarboxylation,
and hydrogenation to tetrahydrofuran.
[Edited on 5-26-2016 by DFliyerz]
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UC235 - 26-5-2016 at 08:42
On anything but plant scale, this idea is hopelessly useless. (and straight hydrogenation to 2,5-dimethyltetrahydrofuran would be a better use of it,
or conversion to 2-MeTHF). The orgsyn prep uses a 12L flask, 6L of hydrochloric acid, and 600g of stannous chloride and produces 63-70g of
methylfurfural.
If you got 65g and the subsequent transformations all had 100 percent yield (which they wont. also, ignoring the cost of nitric acid, Pd/C, and
hydrogen), you'd get 48ml of THF. More realistically, you'd be lucky to get 20ml. Aldrich sells 2L for $165.
You'd be much better trying to isolate it from PVC pipe cement.DFliyerz - 26-5-2016 at 10:03
There are some other methods of synthesizing chloromethylfurfural, which have recorded yields of up to 40%. I'll research those further and post my
findings here.DFliyerz - 26-5-2016 at 10:18
Two more documents describing conversion of cellulose, sucrose, and other similar carbohydrates to chloromethylfurfural in high yields:
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Texium - 26-5-2016 at 19:41
Ok, but that's step one. Compound that with the next three steps and your yield drops more and more each time. I agree with UC235 that it would be
better to buy it or make it a different, less lengthy way. Also, the suggestion of instead making 2-methyl THF is a good point as it can be used for
most things that THF can be used for. However, this still would not be an economical way of making it either.blogfast25 - 27-5-2016 at 05:36
Two more documents describing conversion of cellulose, sucrose, and other similar carbohydrates to chloromethylfurfural (CMF) in high yields:
In that second paper, the reported yields for conversion of cellulose, glucose and sucrose to CMF sound extremely high: 84.0; 82.3 and 91.4 %
respectively.
At these yields it would be worth doing.
Quick question: in the orgsyn method does the SnCl2 play the part of catalyst? Or is it oxidised to SnCl4?
[Edited on 27-5-2016 by blogfast25]DFliyerz - 27-5-2016 at 07:56
I'm trying to figure out a decent way to make 1,2-dichloroethane from ethylene glycol, preferably using a catalyst and HCl to chlorinate.
Actually I'll probably just make 1,2-dibromoethane instead. Shouldn't affect the reaction since it's just acting as a solvent.
