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oxygen1600
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[*] posted on 21-6-2010 at 18:20
nitroalkane synthesis


There have been some ongoing discussions in this website regarding the synthesis of various nitroalkanes. I happened to come across one publication, which gives a simple and relatively mild method for preparing various nitroalkanes using polymer assisted nitrites. Ive attached the pdf of this publication for those who are interested. If anyone has performed this reaction please share your experience.

Attachment: nitroalkane_polysynth.pdf (57kB)
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stateofhack
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[*] posted on 22-6-2010 at 00:42


Old.....
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Paddywhacker
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[*] posted on 22-6-2010 at 12:48


Yes, this has been seen before. But obviously not everybody knows about it, and it is an interesting paper, well within the abilities of amateurs, so bringing it to our attention again is appreciated.

The PVP polymer is widely used in industry, and ethyl iodide can be prepared by methods detailed in the prepublications forum, so making the quaternary PVP should be within the scope of any of us.

The nice thing about the polymer it is that that it can be recovered and regenerated.

When I first read this paper I wondered if a conventional anion exchange resin could be used instead of the quat. PVP, but I have not had the inclination to try it out. Maybe someone here could do that and let us know.

Solid-supported reagents are not just interesting subject, academically .... they lend themselves to very simple workups ... just filter off the resin.
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Anders Hoveland
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[*] posted on 22-6-2010 at 21:01


If anyone can provide a simple rough synthesis for a reaction involving making a nitrite substrate, and also a demonstrating reaction with the substrate, it would be appreciated. I would like an alternative to AgNO2, AgNO3, and AgClO4 precipitation reactions. In otherwords, can someone translate that paper into simple English and write a 2 Paragraph summary?
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peach
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[*] posted on 23-6-2010 at 16:09


I think you'll get some replies to that in English, but probably not very polite ones. :P

PVP is used for iodine scrub solutions in hospitals. I had a massive container of it from BASF at one point and was using it to get washed with. Germ free and a fake tan! :D
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AndersHoveland
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[*] posted on 19-4-2011 at 22:48


It is not completely impossible to directly nitrate alkanes into nitroalkanes at room temperature, the trick is to use a nitronium salt, not mixed acids:
http://www.pnas.org/content/94/22/11783.full

The vapor phase nitration of propane with nitric acid at 420degC produces various nitroalkanes in 40% yield.
The yield for nitromethane is only 4%, for nitroethane 10%, for 2-Nitropropane the yield is 16%.
The various nitroalkanes are then separated by distillation. Nitomethane boils off first at 101degC, then nitroethane at 114degC. 2-Nitropropane boils at 120degC. 1-Nitropropane boils at 131degC. 2-Nitropropane is a carcinogen, breathing of its vapor should be avoided. The vapor-phase nitration can alternatively be done with nitrogen dioxide, giving better yields.



[Edited on 20-4-2011 by AndersHoveland]
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spirocycle
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[*] posted on 21-4-2011 at 08:47


^werent you banned?
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Waffles SS
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[*] posted on 21-4-2011 at 20:46


Pvp isnt cheap polymer

Aldrich Pvp is 130$ per 10 gr(100-200 mesh, extent of labeling: ~6.5 mmol/g Cl resin loading, 2 % cross-linked with divinylbenzene)

Fluka Pvp is 143 per 50 gr
I think ethyl sulfate method is cheaper and easier.
If anyone know cheaper price please let us know


[Edited on 22-4-2011 by Waffles SS]
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UKnowNotWatUDo
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[*] posted on 21-4-2011 at 21:01


Isn't Anders always banned?
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