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Selective synthesis of a valuable unsaturated fatty alcohol via catalytic and non-catalytic liquid-phase methyl oleate reduction
  • Alejandro Vallejo Orrego,
  • Cristian Ferretti,
  • Verónica Díez
Alejandro Vallejo Orrego

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Cristian Ferretti
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Verónica Díez
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The upgrading of oleyl alcohol synthesis via methyl oleate reduction using NaBH4 without H2 supply was investigated. It was possible to synthesize selectively the valuable unsaturated fatty alcohol with high yields. Non-catalytic and catalytic experiments were developed trying to improve the low final oleyl alcohol yield previously obtained. The effect of reaction temperature, methyl oleate/NaBH4 molar ratio and properties of different catalysts on final oleyl alcohol yield was analyzed. Thus, alumina-supported metal (M) catalysts (M = Fe, Ce, Mo) were synthesized by impregnation at incipient wetness. The M/Al2O3 catalysts were characterized in their chemical, textural, structural and acid-base properties using ICP, N2 physisorption, XRD and NH3 and CO2 TPD. During non-catalytic methyl oleate reduction final methyl oleate conversion and oleyl alcohol yield of 94% were obtained using a methyl oleate/NaBH4 molar ratio of 0.11 at 333 K. Catalytic activity of M/Al2O3 solids did not correlate with basic site number but increased as acid site number and ionic potential of M cations increase. This suggests that cations with high acid site number and polarizing power are the ones that promote the polarization of the ester C=O and anion [BH4]- bonds favoring de methyl oleate conversion. In addition, the reaction mechanism for fatty acid methyl ester reduction was investigated from a theoretical approach using Density Functional Theory method at B3LYP/6-31++G(d,p) computational level. Results obtained during theoretical calculations confirmed that the formation of reducing alcoxyborohydride species is energetically favored and allowed to understand the events at microscopic level involved in the reaction mechanism.
28 Jul 2022Submitted to Journal of the American Oil Chemists' Society
28 Jul 2022Submission Checks Completed
28 Jul 2022Assigned to Editor
11 Aug 2022Reviewer(s) Assigned
05 Sep 2022Review(s) Completed, Editorial Evaluation Pending
12 Sep 2022Editorial Decision: Revise Major
25 Oct 20221st Revision Received
25 Oct 2022Submission Checks Completed
25 Oct 2022Assigned to Editor
25 Oct 2022Review(s) Completed, Editorial Evaluation Pending
28 Oct 2022Reviewer(s) Assigned
14 Nov 2022Editorial Decision: Revise Major
27 Dec 20222nd Revision Received
02 Jan 2023Submission Checks Completed
02 Jan 2023Assigned to Editor
02 Jan 2023Review(s) Completed, Editorial Evaluation Pending
03 Jan 2023Reviewer(s) Assigned
16 Jan 2023Editorial Decision: Revise Minor
30 Jan 20233rd Revision Received
30 Jan 2023Assigned to Editor
30 Jan 2023Submission Checks Completed
30 Jan 2023Review(s) Completed, Editorial Evaluation Pending
30 Jan 2023Reviewer(s) Assigned
06 Feb 2023Editorial Decision: Revise Major
09 Feb 20234th Revision Received
09 Feb 2023Submission Checks Completed
09 Feb 2023Assigned to Editor
09 Feb 2023Review(s) Completed, Editorial Evaluation Pending
09 Feb 2023Editorial Decision: Accept