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Interesterification of Soybean Oil and Methyl Stearate Catalyzed by Guanidine-Functionalized SBA-15 Silica

  • Original Paper
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Journal of the American Oil Chemists' Society

Abstract

The main purpose of this study was to develop a heterogeneous interesterification catalyst for the modification of edible oils to enhance their physicochemical and functional performances. To achieve this, 1,3-dicyclohexyl-2-octylguanidine was covalently immobilized on the SBA-15 (Santa Barbara Amorphous 15) material and then used as solid catalysts for the interesterification between soybean oil and methyl stearate. The characterization of the guanidine-functionalized SBA-15 material included Fourier transform infrared spectra, scanning electron microscopy, elemental analysis, and nitrogen adsorption–desorption techniques. It was shown that the solid base catalyst could efficiently catalyze the interesterification reaction. After the interesterification, the fatty acid profiles and triacylglycerol compositions of interesterified products were substantially varied. The influence of interesterification parameters, such as the substrate ratio, reaction time, reaction temperature and catalyst loading, on the interesterification reaction was investigated regarding the percentage of stearic acid in interesterified triacylglycerols. The stearic acid percentage of 27.9 % was achieved at 100 °C within 4 h when the methyl stearate/soybean oil molar ratio of 6:1 was employed. The catalyst could be recovered easily by filtration and reused without significant loss of activity.

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Abbreviations

AOCS:

American Oil Chemists’ Society

BET:

Brunauer–Emmett–Teller

BJH:

Barrett–Joyner–Halenda

CIE:

Chemical interesterification

DCOD:

1,3-dicyclohexyl-2-octylguanidine

DMF:

N,N-dimethylformamide

ECN:

Equivalent carbon number

EIE:

Enzymatic interesterification

ELSD:

Evaporative light-scattering detector

FA:

Fatty acid

FAME:

Fatty acid methyl ester

FT-IR:

Fourier transform infrared

GC:

Gas chromatography

HPLC:

High-performance liquid chromatography

IV:

Iodine value

L:

Linoleic acid

Ln:

Linolenic acid

MeSt:

Methyl stearate

O:

Oleic acid

P:

Palmitic acid

SBA-15:

Santa Barbara Amorphous 15

SEM:

Scanning electron microscopy

SFA:

Sum of saturated fatty acid

SMP:

Slip melting point

SO:

Soybean oil

St:

Stearic acid

SUFA:

Sum of unsaturated fatty acid

TAG:

Triacylglycerol

TEOS:

Tetraethylorthosilicate

TLC:

Thin-layer chromatography

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Acknowledgments

This work was financially supported by research grants from the National Natural Science Foundation of China (Project No. 21276066, 21476062), the Plan for Scientific Innovation Talent of Henan Province (144200510006), the Program for Innovative Research Team in Universities of Henan Province in China (2012IRTSTHN009) and the Fundamental Research Funds for the Henan Provincial Colleges and Universities.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, 450001, People’s Republic of China

    Wenlei Xie, Xinli Yang & Xuezhen Zang

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  1. Wenlei Xie
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  2. Xinli Yang
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  3. Xuezhen Zang
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Correspondence to Wenlei Xie.

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Xie, W., Yang, X. & Zang, X. Interesterification of Soybean Oil and Methyl Stearate Catalyzed by Guanidine-Functionalized SBA-15 Silica. J Am Oil Chem Soc 92, 915–925 (2015). https://doi.org/10.1007/s11746-015-2651-2

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  • DOI: https://doi.org/10.1007/s11746-015-2651-2

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