The use of tris (tetraphenylimidodiphosphinate) of praseodymium chemical shift reagent in proton NMR for the evaluation of the argan oil fatty acids autoxidation and the analysis of the argan pulp fatty acids

Authors

  • Souad Hamdouch Biomolecular and Organic Synthesis Laboratory, Faculty of Sciences Ben M'sik (FSBM), University Hassan II of Casablanca, Morocco
  • Latifa Barkaoui Laboratory of Physical Chemistry and Bioorganic Chemistry, URAC 22, Faculty of Science and Technology, University Hassan II of Casablanca, Morocco
  • Merriem Tarbaoui LIMAT-Thermostructural Materials and Polymers Team, Faculty of science Ben M’sik (FSBM), University Hassan II of Casablanca, Morocco
  • Amine Ouaket Biomolecular and Organic Synthesis Laboratory, Faculty of Sciences Ben M'sik (FSBM), University Hassan II of Casablanca, Morocco

DOI:

https://doi.org/10.13171/mjc8219042706sh

Abstract

Proton NMR is a method of molecular investigation that has its limitations when applied to complex molecules or molecules with many nearly equivalent sites. Previous studies have resorted to the use of paramagnetic chemical shift reagents, having as formula tris (tetraphenylimidodiphosphinate) of lanthanides ln((tpip.)3. The use of reagent Pr(tpip)3 in proton RMN has allowed us to evaluate the autoxidation of fatty acids mixture (stored 6 and 12 months after oil extraction) by the dosage of saturated and unsaturated acids on the one hand, and that of oleic and linoleic acids on the other. We note between 6 and 12 months of storage at 4°C a decrease in the percentage of unsaturated acids (76% to 63%) and an increase in the percentage of saturated acids (24% to 36%). The results show that the oleic acid maintained the same percentage (35%) as it is not easily oxidized whereas, for the linoleic acid, we observe a decrease in percentage from 22.5% to 18.5% (slow autoxidation at 4°C). We also used this NMR method for the analysis of the argan pulp fatty part. The GC analysis shows that it contains very few unsaturated fatty acids and that the main fatty acids are myristic (C14:0) and palmitic (C16:0) acids. The proton NMR with Pr(tpip)3 allowed us to confirm these results. This method that does not require derivation has proven to be interesting, simple and efficient.

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Published

2019-04-27

Issue

Section

Organic Chemistry