Acetone in an 'HI RP E' reaction...

[BullwinkleMoose]

Acetone in an 'HI RP E ' reaction

this bee has recently screwed up and created the above situation: specifically 3-4 mL of Acetone remains in the mix

This bee's question is what effect might this have on the the reaction.

please don't flame too charred ( I mean too hard )


if nobody knows, we will all know by noon tomorrow



lol

[WizardX]

HI will react with the acetone to form 1-iodo-2-propanol, and then =[HI]=> 1,2-iodopropane =[2 HI]=> propane + 2 I2

1,2-iodopropane can also react with the methylamino group -NHCH3

[BullwinkleMoose]

so what sort of health risks are involved with the ingestion of said 1,2-iodopropane ?

and is isopropyl iodide a synonym for 1,2-iodopropane ?


and can 1,2-iodopropane be 'boiled off' from the end product ?

[Rhodium]

so what sort of health risks are involved with the ingestion of said 1,2-iodopropane ?

It is a known mutagen/carcinogen. Look up the MSDS for 1,2-diiodopropane, which is its proper name.

and is isopropyl iodide a synonym for 1,2-iodopropane ?

No, Isopropyl iodide is 2-iodopropane.

and can 1,2-iodopropane be 'boiled off' from the end product ?

No, it will very likely react with the end product before it has a chance to evaporate. Iodoalkanes, and especially diiodoalkanes are extremely reactive at elevated temperatures.

[Scottydog]

So freezing a gear saturated alcohol solution with an aerosol mixture consisting of isobutane and "propane" is not a very wise move?  

Or would this bee a different animal altogether?

Would hate to think that Swim adulterated his product with something harmful. Guinea Pig appears okay but ya never know.  

[Rhodium]

So freezing a gear saturated alcohol solution with an aerosol mixture consisting of isobutane and "propane" is not a very wise move? frown

Or would this bee a different animal altogether?

Very different. Iodine is unable to add to saturated alkanes like the ones you mention, so they won't form any iodoalkanes.

[Organikum]

Although the reaction of HI with acetone is outlined correctly by the Wiz I would believe that under the conditions given the acetone will undergo mainly self-condensation and form a nice polymere which probably will contain much of the pfed around as addition product or else.

But even more probably the acetone will be boiled away - with a boiling point of below 60°C..... (depends of course on the condensor etc.)
But I wouldnt bet my health on it.

[WizardX]

I should have also added this as a possible side-reaction. If the red phosphorus is of good quality (and not match box) the I2 produced during the reduction will be converted back to HI and the concentration of I2 will be minor to nil.

However, as the concentration of I2 increases so will the reaction between I2 and acetone forming iodoacetone.

I2 + CH3-C(=O)-CH3 ==[HI acid catalyst]==> I-CH2-C(=O)-CH3 + HI

[BullwinkleMoose]

the acetone inhibited a good reaction and  lots of pseudo remained in the post rxn work up... 

Not even anything looking like IODO-Pseudoephedrine

All was discarded and moose began again without beer.