Author Topic: CH2I2 via the finkelstein reaction of DCM under pressure with NaI in acetone.  (Read 95 times)

Carrion Fairy

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CH2I2 via the finkelstein reaction of DCM under pressure with NaI in acetone.
« on: March 14, 2009, 04:13:28 AM »
From rhodium: "Methylene chloride (30 grams) is mixed with sodium iodide (120 grams) and warm acetone (100 ml) and heated in a sodawater bottle for ten hours; the bottle is then re-corked and the heating continued for a further ten hours. After standing overnight, the acetone solution is decanted from the sodium chloride, the latter washed with acetone, and the acetone distilled off ; water is then added and the crude methylene iodide extracted with ether. The ethereal solution contains iodine and is washed with water containing sodium hydrogen sulphite, dried, and the ether distilled off. The residue is then fractionated under reduced pressure, when, after a little methylene chloro-iodide has passed over, methylene iodide distils at about 150°C at 300 mmHg, the yield being at least 60%. If the recovered acetone, containing methylene chloride, is employed in a subsequent operation, the yield is about 10% higher."

Has anyone ever performed this reaction?
Will it work if I use a 2L PET coke bottle? What temperature would one recommend? Would DMSO be a better solvent than acetone? I read on wikipedia it is often used for the finkelstein halide swap. I really need any assistance or thoughts you can provide with this, i want to be as prepared as possible. Thankingyouuuuuuu.

Vesp

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Re: CH2I2 via the finkelstein reaction of DCM under pressure with NaI in acetone.
« Reply #1 on: March 14, 2009, 04:48:21 AM »
I think the methylene chloride, and methylene iodide might have a tendancy to dissolve the PET, or at least soften it. I'd test this, or look into it before you do anything on a large scale.
As for the acetone vs DMSO question,  I don't know right now, I'll look into it when I have time.
This is a reaction that I am quite interested in as well.
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Carrion Fairy

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Re: CH2I2 via the finkelstein reaction of DCM under pressure with NaI in acetone.
« Reply #2 on: March 15, 2009, 06:08:49 PM »
Well I can confirm that PET is softened by DCM, I placed 20ml of paint stripper with high DCM content in a diet coke 2L bottle (PET) and in a few minutes the plastic was soft and flexible. This wasn't due to the methanol content, as i tried the same thing with methanol and no softening was observed. This means that 2L coke bottles are unsuitable vessels for this reaction.

I am going to try this reaction in a "pipe-bomb" style arrangement: A length of steel pipe with screw-on end caps, heated to different temperatures. I will try 60degC and 100degC.

I suspect, given that the report I quoted was from 1921, that what was used was in fact glass, like this: http://i3.iofferphoto.com/img/item/883/404/91/o_sD8i4yimwXwradU.jpg
They also speak of 'recorking', this seems fitting for a bottle of this nature.

Vesp

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Re: CH2I2 via the finkelstein reaction of DCM under pressure with NaI in acetone.
« Reply #3 on: March 15, 2009, 07:01:45 PM »
Makes sense.. You could always use one of those class coke bottles they sell today, but I like your pipe bomb idea much better. It obviously wouldn't come apart and the metal wouldn't interact while  the plastic or the cork may.

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