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Author: Subject: Bis(2-Chloroethyl) Ether - an alternate route
DDTea
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[*] posted on 3-4-2003 at 15:24
Bis(2-Chloroethyl) Ether - an alternate route


OK, story time! Your friend Samosa just came back from the Pet Shop, with a brand new bottle of 37% Formaldehyde. If you are interested, the brand name is "Pond Care" and the name of the product is simply "Formalin." It was an 8 oz (240 ml) bottle, and set me back $10.49 . Anyhow, as I came home, I went on the computer to find a Material Safety Data Sheet for 37% Formaldehyde, so I can know the safest ways to handle it, and I came across this excerpt in the "Incompatabilities section."

Quote:

Reaction with hydrochloric acid may form bis-chloromethyl ether, an OSHA regulated carcinogen.


It is not the Carcinogen part that caught my attention, but the bis-chloromethyl ether, which is very poisonous! Even more interesting, this is very related to bis-chlorethyl ether, which is another poison. And, as you may have noticed, that is very close to bis-chloroethyl Thioether, or Mustard! And its inhaled toxicity is very close to that of mustard, although it has almost no skin action since it is unable to penetrate the skin.

Now, my conclusion: this provides a very easy way to get a mustard-type Compound. However, instead of using Formaldehyde, Acetaldehyde would be reated with Hydrochloric Acid to get bis-chloroethyl ether. This is much easier than the conventional method, which involves reacting Diethyl Ether with Phosphorus Pentachloride, a chemical that is not easy to come by.

Now the questions: Iodine in place of the Chlorines in this compound, as well as Mustard, makes the compound a bit more poisonous. Would you expect Hydriotic Acid to react the same way that Hydrochloric Acid would? And also, would you expect for Acetaldehyde to react the same way as Formaldehyde?

[Edited on 4-3-03 by Samosa]
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Blind Angel
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[*] posted on 3-4-2003 at 16:01


Doing reseach yield only Iodomethyl methyl ether (closest component i found)... maybe this component get reduced to that in HI or you will simply discover a new poison to test on rat :P
I think this is a great idea to try though, would be cool to try i with Thiodiglycol too




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DDTea
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[*] posted on 6-4-2003 at 19:41


After checking the Organic Synthesis Database, here is perhaps the best (as in easiest) procedure I have found for reacting HCl with Formaldehyde...

1. Formaldehyde or Paraformaldehyde are put in a mixture with Sulfuric Acid.

2. Place the mix in an ice bath.

3. Slowly add Ammonium Chloride and Chlorosulfonic Acid to the mixture, trying to avoid the loss of any HCl

The purpose of the NH4Cl and Chlorosulfonic Acid is clearly to simply produce HCl in situ, so instead of those difficult-to-come-by chemicals, I will simply substitute NaCl. Sulfuric Acid and Table Salt has never failed to produce HCl before! :D

After the actual reaction, the layer of bis(chloroethyl) ether is separated and then washed, distilled under vacuum, etc. However, my goal is not for a very pure product, but simply to see if I can make it. The purity will come later, when I actually have good equipment :P. I am NOT going to work with a Class-A Carcinogen in improvised labware.
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PHILOU Zrealone
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sad.gif posted on 7-4-2003 at 02:56


All reactants must be 100% anhydrous!

CH2=O(g) + HCl(g) <--> Cl-CH2-OH
Cl-CH2-OH + CH2=O (g) --> ClCH2-O-CH3 (g)

CH2=O + 2HI --> CH3-OH + I2 (possible owing to the reductive power of HI and owing to oxydising power of CH2=O)!

CH3-CH=O + HCl <--> CH3-CHCl-OH
CH3-CHCl-OH + CH3-CH=O --> CH3-CHCl-O-CH2-CH3

I don't see how you would get
ClCH2-O-CH2Cl
ClCH2-CH2-O-CH2-CH2Cl
CH3-CHCl-O-CHCl-CH3
???????????
Since all those halides are hydrolytically unstable!


:(:(:(




PH Z (PHILOU Zrealone)

"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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DDTea
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[*] posted on 7-4-2003 at 10:35


The reaction proceeds as follows:

2 CH2=O + 2 HCl --> (ClCH2)2O + H2O

However, ClCH2-O-CH2Cl is indeed unstable in water. It does dissolve in water, but is soon broken down to HCl and Formaldehyde, if I recall correctly.

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0101

This is the synthesis from the Organic Synthesis Database.
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