Sciencemadness Discussion Board

Finally, a phorone preparation!

Polverone - 10-12-2003 at 20:39

I still have extreme doubts that DPPP can live up to the hype, but maybe now a few more people can try making it. This information was originally posted on the Hive by "ning":

"The preparation of Triacetone Hydrate"
JCS 1927, 2897

The following method was devised some years ago, but was not described at the time, since it was desired to investigate the other products of the reaction and to increase materially the yield of the base.
Into a mixture of 2.5 kg acetone and 800 g fused calcium chloride in a large (no kidding) round bottomed flask provided with an efficient condenser, ammonia is passed at intervals until the whole of the chloride has been converted into a liquid complex. After 3 days, the product is gently boiled on a water bath until the liquid calcium chloride-ammonia compound has decomposed and resolidified, ammonia being evolved. The dark, strongly smelling liquid is then decanted from the solid or pasty chloride, and distilled until a thermometer in the vapor registers 75 C; the distillate consists chiefly of acetone. The residue is placed in a freezing mixture of ice and hydrochloric acid and when the temperature has fallen to 1-2 C an amount of water is added, with vigorous stirring, corresponding to a yield of 28% of triacetoneamine calculated on the acetone used. i.e., the amount taken less that distilled off. Triacetoneamine hydrate separarates in a crystalline condition as the temperature falls; after being pressed between filter paper and recrystallized several times from undried ether, it is obtained in large, well-formed, slightly yellow crystals (yield, 20-26%, calculated on the acetone used).
The conversion of the hydrate into the nitrosotriacetoneamine is carried out in the usual manner and the yield is quantitative. The extreme ease with which this nitrosoamine is decomposed catalytically by alkalis, giving a nearly quantitative yield of phorone, renders this an elegant method for the preparation of this unsaturated ketone. (JCS 1912, 2358).

Marvin - 12-12-2003 at 05:38

I thought Id mentioned this before, but it might not have been this forum.

If you saturate acetone with dry HCl gas, leave for 2-3 days, neutralise with sodium carbonate and drown, you get a water insoluable oil that you can seperate by distillation into metysl oxide and phorone. I dont have a yeild for this process though.

KABOOOM(pyrojustforfun) - 13-12-2003 at 21:01

from Penguin Dictionary of Chemistry (translated it back)
triacetonamine or 2,2,6,6-tetramethyl-<font face=symbol>g</font>-piperidone
needle like colorless crystals, mp: 35°C, bp: 205°C. forms a monohydrate with mp of 58°C. is made from diacetoneamine and propanone or by passing ammonia gas through propanone containing calcium chloride. <font face="antigoni med">its decomposition produces phorone and ammonia</font> and its reduction tetramethyl 3-hydroxypiperidine. it is used for benzamine hydrochloride synthesis.
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