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Author: Subject: Phorone
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[*] posted on 13-11-2002 at 16:01


what the fuck.....did anyone try to import photos yet?

....u can still paste the urls....sorry
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[*] posted on 13-11-2002 at 18:07


I think it's clear that the addition of the sodium bicarbonate initiates a more complex chemical change than an acid-base reaction.



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[*] posted on 13-11-2002 at 18:11


Whoops, I meant to say sodium carbonate.

I forgot to ask: was there fizzling upon addition of the sodium carbonate to the yellowish solution prepared by heating acetone and HCl together?




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[*] posted on 14-11-2002 at 10:58


Yes, there was fizzling.....it was (as expected) a very vigorous reaction.
The addition had to be done very slowly.
I did NOT add an excess(stopped the addition at ph7-8) and immediately washed the precipitate with large amounts of water.
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[*] posted on 27-11-2002 at 12:31


I`ve found a pic of phorone crystals in my archive. :)

isophorone.jpg - 2kB




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[*] posted on 13-8-2003 at 13:36


This is an older thread..sorry for dredging it up. Recently, I attempted Phorone with 33.25 ml HCl and 42.73 ml Acetone. I did my mixing with room temperature chemicals. I added the acid fairly rapidly, in around 4 steps, whilst stirring vigorously. After the addition of the acid, the temperature was quite high. For some reason, I decided to cool it down. Before placing in the freezer, it was slightly foggy, but otherwise colorless water. It was placed in a -5 degree celcius freezer for one hour. After one hour, the liquid was clear, losing the bit of fogginess within. I set the flask in room temperature darkness and promptly forgot about it. About 18 hours later, the liquid within the flask has turned a yellow a bit darker than urine. I let it set back. 6 hours later, the solution is barely darker and with a slight tinge of orange. I tried to add a bit of sodium carbonate. I expected to see fizzing and bubbles as the acid is neutralized. The bit of crystals simply sunk to the bottom. After much swirling, only a slight bit of the mass on the bottom has dissolved, and the amount put in was the ever scientific 'half of a pinch'. The sodium carbonate isn't forming any bubbles at all. Also, the solution smells similar to acetone, with a strange twang to it. I am letting it set some more, seeing if it will turn to a darker red.
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[*] posted on 18-7-2004 at 23:13


I am bringing this thread up from the depths of at least the sixth page in the organic chemistry section, I hope thats okay.

I found this reaction in "Textbook Of organic chemistry" Noller, 1958.
"Under more vigorous conditions of catalysis and dehydration, higher condensation products are formed
3CH3COCH3--->phorone+ 2H20"
The conditions that were above the arrow are dry HCl, ZnCl2 or AlCl3.
Since dry HCl is required I assume that the acetone should be dry as well.
Also, since "vigorous... dehydration" was stated, it may be necessary to remove the water formed in the reaction. However, since concentrated sulfuric acid will not work for drying out the reaction in this case(production of mesitylene), a more suitable drying agent must be found. Ideas?

I would try this but my acetone is not anhydrous.:(
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[*] posted on 19-7-2004 at 02:53


As a drying agent I think anhydrous Sodium sulphate could be used. It is highly unreactive, and I suppose slightly soluble in anhydrous acetone.

Edit: Btw, anhydrous Na2SO4 can also be used to remove the water in the azeotropic acetone/water mixture.

[Edited on 19-7-2004 by Esplosivo]




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[*] posted on 19-7-2004 at 13:23


An old method of producing metisyl oxide and phorone Ive mentioend before. Saturate acetone with dry HCl and leave for a day or two until it aquires a yellow colour. Neutralise with alcoholic potassium carbonate. Adding water to the product should produce an insoluable oil which is a mixture of phorone and metisyl oxide. These are seperated by distillation.

Replacing the neutralising agent with CaCO3 seems like a good move as mentioned earlier.

Having said this, it isnt clear if phorone peroxide can actually be made from phorone. I'm not aware double bonds usually peroxide easily with hydrogen peroxide.
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[*] posted on 27-12-2004 at 19:12
new route to phorone?


First off, I will not pretend to know the chemistry behind an Aldol condensation reaction. I will, however, share my thoughts and observations on the matter. I'm sorry for digging up an old thread, but it's probably better than starting a new one.

Now, lets put on our thinking caps. Acetone and H2SO4 condense primarily to mesitylene, along with some other aromatic and possibly straight chain crap. HCl will condense acetone to phorone. Or dichlorophorone, or pentachlorophorone...depends who you ask. Either way, you get A phorone from HCl. BaOH supposedly consenses acetone to Mesityl Oxide.

Many acids and bases have been seen to provide different condensation products. I believe, though, that good old lye may be the answer. Yesterday, I put a small jar of aqueous NaOH (unsure of concentration, but probably around 20% by weight) and acetone, equal volumes, on a hotplate at around 65 C for roughtly 6 hours. Over time, the upper acetone layer took on a pale yellow color. Unfortunately, the lye phase and acetone phase were immiscible, leaving a very small reaction zone.

Today, I separated and evaporated the acetone phase. I was left with a few grams of a non-crystaline yellow mass. It was definitely a lachrymator, but did not smell of acetone. By its physical properties, I have ruled out the possibility of it being Mesitylene, Mesityl Oxide, Isophorone, and Diacetone Alcohol. Unfortunately, I still can't figure out exactly what I have. If anyone could field a more educated guess than mine, it would be greatly appreciated.

Currently, I have a jar of 300ml of each of ~25% NaOH soln. and acetone, with the acetone floating atop the lye. Over the past 2 hours, at room temp., the acetone has taken on a very light yellow hue, suspiciously charectaristic of the acetone coloration described in the HCL/acetone procedure for phorone. I plan to leave this overnight, and will update everyone on its progress sometime tomorrow.




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[*] posted on 29-12-2004 at 10:14


My above mentioned lye/acetone mix has now been reacting for about 36 hours at room temperature. The acetone layer has taken a bright, translucent yellow hue, while the lye layer is completely clear. If anyone is interested, I will post a picture...I just need to install my digicam software on my laptop, but I'm a lazy lazy man.

I plan to let the mix react until no further color change is seen. I've been shaking it a few times a day to achieve an emulsion, but the emulsion breaks quickly. If anyone knows of an inert emulsifier that I could use to keep the mix emulsified and hopefully speed up the reaction, I would be greatly appreciative.




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[*] posted on 25-8-2006 at 11:03


I made some phorone with solid NaOH and acetone and heat it up (not boiling) overnight. All was left was a black solid-goo (contains NaOH and phorone). The mixture smelled strongly of some kind of wood (I presume that it is camphor-like).

Dissolve this in as little acetone as possible.

Then dilute it with water until phorone precipitates. There should be a red goo floating on top. This red good is responsible for the red black color and can be easily removed with a toothpick.

Now evaporate the water and redissolve in some acetone to remove NaOH. (Solution should be a bright yellow color only)

Evaporate the acetone to have almost pure phorone.


[Edited on 8/25/2006 by guy]

[Edited on 8/25/2006 by guy]




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[*] posted on 27-8-2006 at 23:12


What makes you believe that what you obtained is phorone? What kind of analysis did you perform?

Somehow I doub't you can evaporate a water solution of phorone (for that little that is soluble) without steam disstiling off any potential phorone. Anyway, NaOH and acetone gives diacetone alcohol (4-Hydroxy-4-methyl-2-pentanone).




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[*] posted on 29-8-2006 at 20:48


I don't know for sure but it smells like phorone and looks like phorone. Phorone is slightly soluble in water and has a much higher boiling point than water (around 200). NaOH and acetone does give diacetone alcohol, which will dehydrate to form mesityl oxide, isophorone, phorone, and some other stuff. Phorone is the only solid at room temperature.



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