garage chemist - 31-3-2007 at 21:54
I recently got about 300-500g of pure crystalline acrylamide (I know it is toxic). What would be interesting uses for it?
Could it be polymerized, in order to obtain a watersoluble polymer, maybe as a superadsorbent?
Or dehydrate it to acrylnitril using SOCl2, and then make PAN plastics or fibers?
Or simply acrylic acid, this already has a lot of uses...
matei - 1-4-2007 at 03:09
Acrilamide is not just toxic, it's carcinogenic. It can be polymerized and copolimerized with N,N'-methylene-bis-acrilamide to obtain gels used for
electrophoresis.
Nicodem - 1-4-2007 at 10:39
Well, a bunch of things are carcinogenic. Who cares except for the non-chemists?
Anyway, acrylamide is carcinogenic because it is electrophilic enough to alkylate various biologically crucial nucleophilic groups (like the amino
groups on nucleic bases in DNA). So, not particularly ironically but anyway, you could use its alkylating ability to make various compounds. For
example, you can alkylate different amines with it. If you alkylate ethylenediamine you get the "tetramide of EDTA",
(H2NCO-CH2)2N-CH2-CH2-N(CH2-CONH2)2. If you get it to alkylate ammonia you get N(CH2-CONH2)3 and so on. These are great starting materials for various
dendrimeric molecules if you would be able to reduce the amides to amines, alkylate them again with more acrylamide and repeat this a couple of times.
But, unfortunately, it is a bitch to reduce amides by any simple method.
garage chemist - 1-4-2007 at 22:39
Does this really yield EDTA-amide? Acrylamide is a C3 compound, EDTA has only C2-chains on the amine nitrogens.
Nicodem - 1-4-2007 at 23:28
Ups, sorry, I was not thinking much about what the product was. You are right and it should have additional methylenes and stand as
(H2NCO-CH2-CH2)2N-CH2-CH2-N(CH2-CH2-CONH2)2 (which is obviously not "tetramide of EDTA" but its homologue). And the alkylated ammonia should similarly
be N(CH2-CH2-CONH2)3. I'll check the literature when I'll have time.