golfpro
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ETN chemistry question
Why is it the case that using Concentrated HNO3 in place of AN produces much greater yeilds of ETN (according to wikipedia)?
molar equivalent of NO3- of 60g AN is 35ml of PURE Nitric acid, less dehydration is needed w/ anhydrous nitric acid, so I'd use less sulfuric acid,
and while I'm at it double the ratios to:
70ml 92% HNO3
55ml 90% H2SO4
40g fine powdered erythritol
This would theoretically produce 96g of ETN or so.
How close to maximum would my yield be do you think?
I've tried multiple times w/ pure, dry AN could never get over a 20g yield. Plus I think using nitric acid, this synthesis could scale a bit better.
I would take RDX over ETN any day of the week but look: 1g of RDX = 7-8ml 99% HNO3.
10g ETN = that same amount of nitric acid, and when all I have is a retort....
Thoughts?
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Rosco Bodine
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http://en.wikipedia.org/wiki/Erythritol_tetranitrate
The wiki article cites no authority for its statement that a better yield is obtained by use of nitric acid for the nitration than is the yield
obtained by use of a nitrate and sulfuric acid, nor is it necessarily so that the statement is true.
So the premise of the question may be faulty.
A hint to the speculative nature is the statement that ammonium nitrate is commonly used for this type reaction, which is an overly broad and general
statement which ignores the operative catalytic effect of certain anions of nitrate salts and results in all nitrates not being equal in their ability
to nitrate a given material. Depending on the thing being nitrated one nitrate will work better than another. And it is also conceivable that in
some cases a nitrate may work as well or perhaps better than free nitric acid. Only the authority of comparative experiments cited for reference
would lend needed credibility to the assertion being made by that wiki article regarding the magical power of nitration attributed to the free nitric
acid.
Attached is a description of the nitration using mixed acid.
And a link to one of the several described nitrations using a nitrate and sulfuric acid.
http://www.sciencemadness.org/talk/viewthread.php?tid=1100&a...
[Edited on 30-9-2013 by Rosco Bodine]
Attachment: ETN Paper accepted PEP.pdf (806kB)
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Rosco Bodine
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Here attached is another authority for a mixed acid nitration of erythritol to provide a reported 89% yield
Attachment: ETN as sensitizer for NH4NO3 Kunzel.pdf (213kB)
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