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Topic: Phosphoric acid for organic nitrite synthesis  (Read 3616 times)

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Offline XIXTRUMP

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Phosphoric acid for organic nitrite synthesis
« on: December 12, 2010, 02:32:24 PM »
I'm working on synthesis of organic nitrites, commonly used as special reagents for other syntheses.

The common reference of a organic nitrite synthesis is given in: Organic Syntheses, Vol. 16, p. 7 (1936); Coll. Vol. 2, p.108 (1943). This procedure is generally used with long-chain alcohols to produce the corresponding nitrite.

Sulphuric acid raises Tº from 0 to 70º C in less of 3 minutes, and this synthesis must be keep cold, due the decomposition of nitrous acid formed in situ and the competition of the elimination reaction. Cause of that, addition of acid must be very  slow.

However, I accidentally used phosphoric acid in this reaction (due to a mistake of the chem store), obtaining the nitrite, but with higher yields that expected in less time.


Offline MissPhosgene

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Re: Phosphoric acid for organic nitrite synthesis
« Reply #1 on: December 12, 2010, 03:49:14 PM »
That sounds pretty good. I don't really know what the question is...
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline Hybrid

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Re: Phosphoric acid for organic nitrite synthesis
« Reply #2 on: December 13, 2010, 03:12:26 AM »
if u sure that is the pdt is the desired nitrite with good purity so H3PO4 is useful for organonitrite synthesis as H2SO4

Offline XIXTRUMP

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Re: Phosphoric acid for organic nitrite synthesis
« Reply #3 on: December 19, 2010, 10:28:05 PM »
Oh, I forgot the question...

Well, I'm trying to describe the reaction mechanism, I supossed It is SN2, but would it be possible a sterification mechanism?

New experiments about yields of reaction with phosphoric acid has shown that If I don't take care about Tº (5ºC or more) I got higher yields, and with sulphuric acid the opposite happens, but I need someone who makes the experiment to compare results.

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