Interesterification of Soybean Oil with Propylene Glycol in Supercritical Carbon Dioxide and Analysis by NMR Spectroscopy

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The time course study of high monoester mixtures from soybean oil (HMMS) synthesis, as healthier alternatives to trans food products, in a supercritical CO2 (SCCO2) medium with and without enzyme, was investigated. Phosphorous nuclear magnetic resonance (31P-NMR) was used to quantify the absolute amount of partially esterified acylglycerols (PEGs). Carbon NMR was utilized to determine the type and position of the fatty acids (FAs) of HMMS. Enzyme and time significantly influenced the synthesis of 1-monoglycerides (1-MGs), 2-MGs, and 1,2-diglycerides (1,2-DGs) in this alcoholysis of soybean oil with 1,2-propanediol, based on high catalytic activity and operational stability of Novozym 435 in SCCO2 during short reaction time. Results suggest that 4 h is a suitable reaction time for this lipase-catalyzed interesterification (LIE) system for the synthesis of 2-MGs with a yield of 20%. The highest polyunsaturated fatty acid (PUFA) (65%) in the triglyceride (TG) of HMMS was produced after 4 h of reaction. After 6 h of reaction, a high level (20%) of saturated fatty acids (SFAs) was found in the TGs of HMMS, which were distributed between the sn-2 (5%) and sn-1, 3 (15%) positions.

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Analysis of variance


Chemical interesterification




Cardiovascular disease




Docosahexaenoic acid


Eicosapentaenoic acid


Fatty acids


Food and Drugs Administration-USA


Generally recognized as safe


High monoester mixtures from soybean oil


Lipase-catalyzed interesterification




Monounsaturated fatty acids


Partially esterified acylglycerols

31P-NMR :

Phosphorous nuclear magnetic resonance


Polyunsaturated fatty acid


Supercritical CO2


Saturated fatty acids


Structured lipids




Unsaturated fatty acids


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Correspondence to Martin G. Scanlon.

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Vafaei, N., Eskin, M.N.A., Rempel, C.B. et al. Interesterification of Soybean Oil with Propylene Glycol in Supercritical Carbon Dioxide and Analysis by NMR Spectroscopy. Appl Biochem Biotechnol (2020).

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  • Monoglycerides
  • Lipase-catalyzed interesterification
  • Supercritical CO2
  • Novozym 435
  • NMR