2
$\begingroup$

I read a paper about enzyme-catalysed synthesis of octanamide.

What is octanamide used for?

$\endgroup$
4
$\begingroup$

Well, one thing is as plastics. Nylon is a linear polyamide; it's traditionally produced from alkyl-diamines and a dicarboxylic acid (to donate the acyl group of the amides, as well as a second alkyl chain joined directly to the carboxyl), and the typical product is a poly-hexanamide, but nylon-8,x variants are also possible, as are reactions involving a more direct route of welding the monomers together and arriving at the same place.

Some Google-fu turns up a number of possible end products for which octanamide aka caprylamide would be a useful intermediate. By itself, it's an emulsifier and common solvent in organic synthesis. Other alkyl amides including derivatives of octanamide, often with a few additional alkyl or amino groups welded on, are used in drugs, inks/dyes, fragrances, and skin care items. N,N-dimethyloctanamide and N,N-diethyloctanamide appear to be common ingredients in deodorants and sunblocks, though I'm not sure if they're an actual fragrance or a carrier/stabilizer (Edit: they seem to be emulsifiers and stabilizers for essential oils of the fragrances in water-based products).

$\endgroup$
  • $\begingroup$ Good overview, +1 if you can provide me with the reference for the imidazole synthesis from butanamide. $\endgroup$ – TMOTTM May 8 '13 at 9:56
  • $\begingroup$ Grr, I had it when I wrote it. The closest I can find now is that 2-aminobutanamide is an intermediate in the synthesis of Levetiracetam (Keppra, antiepileptic) but that's only a pyrrole compound and not put together from the intermediate the same way I saw the imidazole synthesis. $\endgroup$ – KeithS May 8 '13 at 15:10
  • $\begingroup$ This is the closest I can find: ccc.chem.pitt.edu/wipf/current%20literature/mike_2.pdf - page 12 shows the reaction of an amidine (which exchanges the oxygen of the carboxyl of the amide to an amine group) with a haloether to form imidazoles. Butyramidine is a possible candidate but it's not quite the same as butyramide (or octanamide FTM), and I can't find a procedure for synthesis of amidines directly from amides; most procedures will get you one or the other from the same starting material (often the carboxylic acid) depending on variations in workup. $\endgroup$ – KeithS May 8 '13 at 15:52
  • 1
    $\begingroup$ The first part on polyamides is plain nonsense, there is no polyamide from a monoamide. Second Nylon 6,6 is not produced any longer, all "6" polyamid is Nylon 6, called Perlon correctly. The switch was due to technoeconomic reasons. $\endgroup$ – Georg May 21 '13 at 18:27

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.