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

What is octanamide used for?


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).

  • $\begingroup$ 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
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    $\begingroup$ 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

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