Skip to main content
SpringerLink
Log in

An Innovative Deacidification Approach for Producing Partial Glycerides-Free Rice Bran Oil

  • Original Paper
  • Published:
Food and Bioprocess Technology Aims and scope Submit manuscript

Abstract

In the present study, an innovative deacidification approach has been established for producing partial glycerides-free rice bran oil (RBO). Partial glycerides (monoacylglycerol (MAG), diacylglycerol (DAG)) in high-acid RBO were firstly hydrolyzed to FAs by immobilized MAG and DAG lipase SMG1-F278N-catalyzed hydrolysis followed by deacidification by immobilized SMG1-F278N-catalyzed esterification. Deacidification efficiency as high as 99.79% was achieved under the optimal conditions. During deacidification, the immobilized SMG1-F278N exhibited excellent reusability. It could be used for 20 cycles without significant loss in activity. After purification by molecular distillation at lower temperature (120 °C), a final product with 99.86% TAG, 0.05% DAG, and 0.09% FAs was obtained. Compared with the previous methods, the new process could effectively remove almost all FAs and partial glycerides. Removal of partial glycerides would favor the downstream refining process and reduce the risk of formation of glycidyl esters during the following deodorization process. Moreover, the by-product (FA ethyl esters) produced during deacidification could be used as biodiesel or as intermediates for the synthesis of other lipids.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Bakhiya, N., Abraham, K., Gürtler, R., Appel, K. E., & Lampen, A. (2011). Toxicological assessment of 3-chloropropane-1,2-diol and glycidol fatty acid esters in food. Molecular Nutrition & Food Research, 55(4), 509–521.

    Article  CAS  Google Scholar 

  • Bayramoğlu, G., Kacar, Y., Denizli, A., & Arica, M. Y. (2002). Covalent immobilization of lipase onto hydrophobic group incorporated poly (2-hydroxyethyl methacrylate) based hydrophilic membrane matrix. Journal of Food Engineering, 52(4), 367–374.

    Article  Google Scholar 

  • Bradford, M. M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry, 72(1–2), 248–254.

    Article  CAS  Google Scholar 

  • Cao, Y., Wang, W., Xu, Y., Yang, B., & Wang, Y. (2013). Enzymatic synthesis of extremely pure triacylglycerols enriched in conjugated linoleic acids. Molecules, 18(8), 9704–9716.

    Article  CAS  Google Scholar 

  • Cheng, W., Liu, G., & Liu, X. (2016). Formation of glycidyl fatty acid esters both in real edible oils during laboratory-scale refining and in chemical model during high temperature exposure. Journal of Agricultural and Food Chemistry, 64(29), 5919–5927.

    Article  CAS  Google Scholar 

  • Craft, B. D., Nagy, K., Seefelder, W., Dubois, M., & Destaillats, F. (2012). Glycidyl esters in refined palm (Elaeis guineensis) oil and related fractions. Part II: Practical recommendations for effective mitigation. Food Chemistry, 132(1), 73–79.

    Article  CAS  Google Scholar 

  • Ghosh, M. (2007). Review on recent trends in rice bran oil processing. Journal of the American Oil Chemists’ Society, 84(4), 315–324.

    Article  CAS  Google Scholar 

  • Knezevic, Z., Milosavic, N., Bezbradica, D., Jakovljevic, Z., & Prodanovic, R. (2006). Immobilization of lipase from Candida rugosa on Eupergit® C supports by covalent attachment. Biochemical Engineering Journal, 30(3), 269–278.

    Article  CAS  Google Scholar 

  • Kosugi, Y., & Azuma, N. (1994). Continuous and consecutive conversion of free fatty acid in rice bran oil to triacylglycerol using immobilized lipase. Applied Microbiology and Biotechnology, 41(4), 407–412.

    Article  CAS  Google Scholar 

  • Lakshmanan, A., Rao, P. V., Jayaraman, K., & Lakshmanan, C. (1992). Lipase catalyzed deacidification of high free fatty acid rice bran oil. Biotechnology Techniques, 6(2), 169–172.

    Article  CAS  Google Scholar 

  • Li, D., Wang, W., Durrani, R., Li, X., Yang, B., & Wang, Y. (2016a). Simplified enzymatic upgrading of high-acid rice bran oil using ethanol as a novel acyl acceptor. Journal of Agricultural and Food Chemistry, 64(35), 6730–6737.

    Article  CAS  Google Scholar 

  • Li, D., Wang, W., Qin, X., Li, X., Yang, B., & Wang, Y. (2016b). A novel process for the synthesis of highly pure n-3 polyunsaturated fatty acid (PUFA)-enriched triglycerides by combined transesterification and ethanolysis. Journal of Agricultural and Food Chemistry, 64(34), 6533–6538.

    Article  CAS  Google Scholar 

  • Li, X., Li, D., Wang, W., Durrani, R., Yang, B., & Wang, Y. (2016c). Immobilization of SMG1-F278N lipase onto a novel epoxy resin: characterization and its application in synthesis of partial glycerides. Journal of Molecular Catalysis B: Enzymatic, 133, 154–160.

    Article  CAS  Google Scholar 

  • Matthäus, B. (2011). 3-MCPD and glycidyl fatty acid esters: what is the knowledge today? European Journal of Lipid Science and Technology, 113(3), 277–278.

    Article  Google Scholar 

  • Sheldon, R. A., & Pelt, P. V. (2013). Enzyme immobilization in biocatalysis: why, what and how. Chemical Society Reviews, 42, 6223–6335.

    Article  CAS  Google Scholar 

  • Van Hoed, V., Ayala, J. V., Czarnowska, M., De Greyt, W., & Verhé, R. (2010). Optimization of physical refining to produce rice bran oil with light color and high oryzanol content. Journal of the American Oil Chemists’ Society, 87(10), 1227–1234.

    Article  CAS  Google Scholar 

  • Wang, W. F., Li, T., Qin, X. L., Ning, Z. X., Yang, B., & Wang, Y. H. (2012). Production of lipase SMG1 and its application in synthesizing diacylglyecrol. Journal of Molecular Catalysis B: Enzymatic, 77, 87–91.

    Article  CAS  Google Scholar 

  • Wang, W. F., Xu, Y., Qin, X. L., Lan, D. M., Yang, B., & Wang, Y. H. (2014a). Immobilization of lipase SMG1 and its application in synthesis of partial glycerides. European Journal of Lipid Science and Technology, 116(8), 1063–1069.

    Article  CAS  Google Scholar 

  • Wang, F., Nie, T. T., Shao, L. L., & Cui, Z. G. (2014b). Comparison of physical and covalent immobilization of lipase from candida antarctica on polyamide microspheres of alkylamine matrix. Biocatalysis and Biotransformation, 32(5–6), 314–326.

    Article  Google Scholar 

  • Wang, W. C., Zhou, W. Q., Li, J., Hao, D. X., Su, Z. G., & Ma, G. H. (2015). Comparison of covalent and physical immobilization of lipase in gigaporous polymeric microspheres. Bioprocess and Biosystems Engineering, 38(11), 2107–2115.

    Article  CAS  Google Scholar 

  • Wang, X., Lu, J., Liu, H., Jin, Q., & Wang, X. (2016). Improved deacidification of high-acid rice bran oil by enzymatic esterification with phytosterol. Process Biochemistry, 51(10), 1496–1502.

    Article  CAS  Google Scholar 

  • Xu, D., Sun, L., Chen, H., Lan, D., Wang, Y., & Yang, B. (2012a). Enzymatic synthesis of diacylglycerols enriched with conjugated linoleic acid by a novel lipase from Malassezia globosa. Journal of the American Oil Chemists’ Society, 89(7), 1259–1266.

    CAS  Google Scholar 

  • Xu, T., Liu, L., Hou, S., Xu, J., Yang, B., Wang, Y., & Liu, J. (2012b). Crystal structure of a mono- and diacylglycerol lipase from Malassezia globosa reveals a novel lid conformation and insights into the substrate specificity. Journal of Structural Biology, 178(3), 363–369.

    Article  CAS  Google Scholar 

  • Yang, B., Yang, J. G., Wang, Y. H., Zeng, Y. P., & Lin, W. T. (2005). Enzymatic deacidification of rice bran oil by esterification [J]. China Oils and Fats, 7, 22–24 In Chinese.

    Google Scholar 

  • Yang, B., Wang, Y. H., & Yang, J. G. (2006). Optimization of enzymatic degumming process for rapeseed oil. Journal of the American Oil Chemists’ Society, 83(7), 653–658.

    Article  CAS  Google Scholar 

  • Yang, B., Zhou, R., Yang, J. G., Wang, Y. H., & Wang, W. F. (2008). Insight into the enzymatic degumming process of soybean oil. Journal of the American Oil Chemists’ Society, 85(5), 421–425.

    Article  CAS  Google Scholar 

  • Yuan, D. J., Wu, Z. D., & Wang, Y. H. (2016). Evolution of the diacylglycerol lipases. Progress in Lipid Research, 64, 85–97.

    Article  CAS  Google Scholar 

  • Zheng, P. Y., Xu, Y., Wang, W. F., Qin, X. L., Ning, Z. X., Wang, Y. H., & Yang, B. (2014). Production of diacylglycerol-mixture of regioisomers with high purity by two-step enzymatic reactions combined with molecular distillation. Journal of the American Oil Chemists’ Society, 91(2), 251–259.

    Article  CAS  Google Scholar 

  • Zheng, M., Zhu, J., Huang, F., Xiang, X., Shi, J., Deng, Q., Ma, F., & Feng, Y. (2015). Enzymatic deacidification of the rice bran oil and simultaneous preparation of phytosterol esters-enriched functional oil catalyzed by immobilized lipase arrays. RSC Advances, 5(86), 70073–70079.

    Article  CAS  Google Scholar 

  • Zigoneanu, I. G., Williams, L., Xu, Z., & Sabliov, C. M. (2008). Determination of antioxidant components in rice bran oil extracted by microwave-assisted method. Bioresource Technology, 99(11), 4910–4918.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National High Technology Research and Development Program of China (863 program, 2014AA093514, 2014AA093601) and Science and Technology Planning project of Guangdong province (2014B020204003, 2015B020231006).

Author information

Authors and Affiliations

  1. School of Food Science and Engineering, South China University of Technology, Guangzhou, 510640, People’s Republic of China

    Daoming Li, Pengzhan Liu & Yonghua Wang

  2. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, People’s Republic of China

    Weifei Wang

  3. School of Bioscience and Bioengineering, South China University of Technology, Guangzhou, 510006, People’s Republic of China

    Xiumei Wang & Bo Yang

Authors
  1. Daoming Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pengzhan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Weifei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiumei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bo Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yonghua Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yonghua Wang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, D., Liu, P., Wang, W. et al. An Innovative Deacidification Approach for Producing Partial Glycerides-Free Rice Bran Oil. Food Bioprocess Technol 10, 1154–1161 (2017). https://doi.org/10.1007/s11947-017-1896-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11947-017-1896-1

Keywords

Search

Navigation