PrimoPyro (Hive Prodigy)
07-20-02 00:01
No 334768
      Preparing 2-halopropionic esters from acryl esters  Bookmark   

I wrote this last night but my phone line went kaput before I could actually post it, so here it is:

Preparing 2-halopropionic esters from acryl esters

The idea is simple and I simple ask if this would work:

Take an acrylic ester of the formula: CH2=CH-(C=O)-O-R and add a hydrohalogen of the formula HX across the double bond to form a 2-halopropionic ester of the formula CH3-CH(X)-(C=O)-O-R.

This would work would it not? The specific reaction desired would be ethyl acrylate and hydrogen chloride, as either the dry gas if necessary, or preferably as concentrated hydrochloric acid with PTC if needed.

I know the reaction works in theory, at least for the dry HX gas anyway. Water's presence would likely saponify the ester, making a mess. What I'm wondering about is the practicality of such a reaction, if a decent (above microscale) quantity of 2-chloroprionic ester is desired to be manufactured, say as an alternative to nitroethane and butylamine.

Just wonderin'


Error 629: The port was disconnected by the remote machine.
07-20-02 09:50
No 334981
      Chem supplier  Bookmark   

Nothing mentioning about the possible succes or failure of your theorem, SWiM like to add that CH3-CHCl-COOH can be obtained from chem suppliers, and it isn't expensive at all (at least not in the catalogue SWiM checked). I think it would be easier to make an ester of this compound then working with HX gas. Just my thought anyway... SWiM doesn't like to work with gas.

-[ A Friend With W33D Is A Friend Indeed ]-
(Stoni's sexual toy)
07-22-02 11:38
No 335730
      I haven't looked into it, but there's always the ...  Bookmark   

I haven't looked into it, but there's always the possibility that you induce an anionic polymerisation which will turn your acrylate into a worthless polymer instead of the desired halopropionic acid.

I'm not fat just horizontally disproportionate.