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Author: Subject: Azobisisobutyronitrile (AIBN) Synthesis Options
Frankenshtein
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[*] posted on 19-9-2020 at 06:19
Azobisisobutyronitrile (AIBN) Synthesis Options


This compound requires hydrazine and acetone cyanohydrin, followed by Chlorine oxidization.

The beginner question is, can I use hydrazine sulfate? Hydrazine hydrate? Anything but free base hydrazine? I ask for the obvious reason of safety.

I know the water in the hydrate is a polar protic solvent and I assume it would have to be removed by heating or a nearby drying agent before attempting the chlorine oxidization.

I am only interested in <1 gram amounts.

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Frankenshtein
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[*] posted on 19-9-2020 at 06:57


On hydrazine hydrate:

From wikipedia: "The principal hazards of acetone cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic hydrogen cyanide."

https://patents.google.com/patent/JP5852183B2/en
Acetone cyanohydrin and hydrazine hydrate would form hydrazobisisobutyronitrile, a different compound.

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So the hydrate is not an option, but hydrazine sulfate?

On hydrazine sulfate:

Some luck was found but with a deuterated form that confuses me:
https://pubs.acs.org/doi/pdf/10.1021/ja00779a036
"AIBN-d, was prepared by the same method using acetone-d6 (99.6 atom Z, Stohler), hydrazine sulfate which had been ex- changed three times with D20 in a Soxhlet extractor, sodium cyanide dried over P2O5 under vacuum, and D20 solvent."

I found enough information, I believe. The similarities and likely irrelevant things like different names, radiation, or deuteration, between these three papers has me thinking they are good matching sources for the synthesis.

https://pubs.acs.org/doi/pdf/10.1021/ja01682a040

Picture from this source:
https://link.springer.com/article/10.1007/BF01167334


So potassium cyanide or sodium cyanide, with acetone or methyl ethyl ketone, and hydrazine sulfate. Oxidation could be done by chlorine or bromine. Not impossible for the amateur.

Sodium with potassium ferrocyanide -> purest NaCN



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[Edited on 19-9-2020 by Frankenshtein]
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njl
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[*] posted on 8-10-2020 at 06:26


IDK if you're still planning on doing this but the cyanohydrin is far more dangerous than freebase hydrazine.
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