Since Juul has a nice application for low-freezing heavy alkaneshttps://www.chemicalforums.com/index.php?topic=99108.0
maybe you chemists could give opinions, comments, remarks about farnesane obtained from caparrapi oil?
The tree, Ocotea caparrapi
or Nates Dugand Lauraceae, is an endangered species. Apparently no restriction on its oil, or rather resin. I hope a commercial use of living trees would help the species rather than threaten it.
The resin comprises mainly nerolidol and caparrapi oxide, plus a bit of diol and triol whose loss wouldn't be bad, plus a zillion minor compounds, and traces of caparratriene that can be lost. Image appended.
Caparrapi oxide might allegedly result from the cyclisation of nerolidol. Unless someone sees how to de-cyclise it to the proper skeleton, I'd remove it by distillation at low pressure. It may serve as a hydrogen source or a perfume.
1atm boiling points estimated (!) by Mpbpvp:
+256°C Caparrapi oxide
+292°C Nerolidol (measured +276°C)
I haven't seen how to remove the alcohols and saturate the double bonds at once. Two steps hence.
To remove the alcohols, I've found only dehydrations. They create a double bond whose random location is unimportant here. Tertiary alcohols are said not to make ethers. At least three usual ways:
- Concentrated phosphoric acid. But it takes sulphuric acid to regenerate anyway.
- Concentrated sulfuric acid. Regenerate by heat, is that correct?
- Alumina, safest. At reduced pressure, the reactants can be gaseous if this helps. Regenerate by heat I believe.
Nerolidol, diol and triol would provide caparratriene and isomers with the same skeleton. I suppose they are too difficult to separate from caparrapi oxide, which is hence distilled away before. Though, if for instance polymerisation of the allenes is likely during the dehydration, maybe the hydrogenation can be done first, and Caparrapi oxide or its products removed by cold and filtration? Or should the dehydration proceed with added hydrogen?
Hydrogenation of all double bonds is usually made by H2
and Pd/C, unless someone knows a better way. The resulting broad mix of right-left isomers contributes to the low melting point.