An effective method for reducing free fatty acid content of high-acid rice bran oil by enzymatic amidation

Xiaosan Wang; Xingguo Wang; Tong Wang

Journal of Industrial and Engineering Chemistry, Vol.48, 119-124, April, 2017

DOI10.1016/j.jiec.2016.12.028 Export Citation

An effective method for reducing free fatty acid content of high-acid rice bran oil by enzymatic amidation

Xiaosan Wang, Xingguo Wang^†, and Tong Wang^{1, †}

State Key Laboratory of Food Science and Technology, Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu 214122, PR China
¹Department of Food Science and Human Nutrition, Iowa State University, 2312 Food Science Building, Ames, IA 50011, USA

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An improved method of deacidification of high-acid rice bran oil (HRBO) by an enzymatic amidation reaction between free fatty acids (FFA) and ethanolamine is described in this study. The reaction conditions were optimized to minimize the FFA content of HRBO. Under optimal reaction conditions (2% of Lipozyme 435, about 1:1 mass ratio of oil to solvent and at 76 °C), acid value of HRBO was reduced from 21.5 to 1.6 mg/g after 4 h reaction. The final oil product was rich in fatty acid ethanolamides (11.9 wt %) which are desirable bioactive lipids. Compared to esterification deacidification using glycerol or monoacylglycerols (MAG) as acyl acceptor, enzymatic deacidification by amidation can be completed in a much shorter time because amidation reaction is much more favorable than the esterification. This is the first time that ethanolamine is used as acyl acceptor to enzymatically deacidify a high-FFA oil. Such an enzymatic route is highly effective and environmentally desirable.

Keywords:Deacidification;Ethanolamine;Immobilized lipase;Amidation;Rice bran oil

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[Referenced By]

[1] Zullaikah S, Lai CC, Vali SR, Ju YH, Bioresour. Technol., 96(17), 1889 (2005)

[2] Rachapudi BN, Lipid Technol., 18, 275 (2006)

[3] Nicolosi RJ, Austrian LM, Hegsted DM, Atherosclerosis, 88, 133 (1991)

[4] Wilson TA, Nicolosi RJ, Woolfrey B, Kritchevsky D, J. Nutr. Biochem., 18, 105 (2007)

[5] Chou TW, Ma CY, Cheng HH, Chen YY, Lai MH, Clin J, J. Clin. Biochem. Nutr., 45, 29 (2009)

[6] Shih CK, Ho CJ, Li SC, Yang SH, Hou WC, Cheng HH, Food Chem., 126, 562 (2011)

[7] Zigoneanu IG, Wilhams L, Xu Z, Sabliov CM, Bioresour. Technol., 99(11), 4910 (2008)

[8] Sinha S, Agarwal AK, Garg S, Energy Conv. Manag., 49(5), 1248 (2008)

[9] Aryusuk KO, Puengtham JI, Lilitchan SU, Jeyashoke NA, Krisnangkura KA, J. Am. Oil Chem. Soc., 85, 475 (2008)

[10] Vaisali C, Charanyaa S, Belur PD, Regupathi I, Int. J. Food Sci. Technol., 50, 13 (2015)

[11] Gofferje G, Gebhardt M, Stabler A, Schweiggert-Weisz U, Floter E, Eur. J. Lipid Sci. Technol., 116, 185 (2014)

[12] Gofferje G, Gebhardt M, Stabler A, Schweiggert-Weisz U, Floter E, Eur. J. Lipid Sci. Technol., 116, 1421 (2014)

[13] Ghosh M, J. Am. Oil Chem. Soc., 84, 315 (2007)

[14] Song ZH, Liu YF, Jin QZ, Li L, Wang XG, Huang JH, Liu RJ, Appl. Biochem. Biotechnol., 168(2), 364 (2012)

[15] von der Haar D, Stabler A, Wichmann R, Schweiggert-Weisz U, Biotechnol. Lett., 37(1), 169 (2015)

[16] Haar D, Stabler A, Wichmann R, Schweiggert-Weisz U, Food Chem., 176, 263 (2015)

[17] De BK, Bhattacharyya DK, J. Am. Oil Chem. Soc., 76, 1243 (1999)

[18] Valerio A, Kruger RL, Ninow J, Corazza FC, Oliveira DD, Oliveira JV, et al., J. Agric. Food Chem., 57, 8350 (2009)

[19] Craft BD, Nagy K, Seefelder W, Dubois M, Destaillats F, Food Chem., 132, 73 (2012)

[20] Kuehl F, Jacob T, Ganley O, Ormond R, Meisinger M, J. Am. Oil Chem. Soc., 79, 5577 (1957)

[21] Wang X, Chen Y, Ma Y, Jin Q, Wang X, J. Mol. Catal. B-Enzym., 122, 233 (2015)

[22] Calignano A, Rana GL, Giuffrida A, Piomelli D, Nature, 394, 277 (1998)

[23] Astarita G, Giacomo BD, Gaetani S, Oveisi F, Compton TR, Rivara S, Tarzia G, Mor M, Piomelli D, J. Pharmacol. Exp. Ther., 318, 563 (2006)

[24] Lucanic M, Held JM, Vantipalli MC, Klang IM, Graham JB, Gibson BW, Lithgow GJ, Gill MS, Nature, 473(7346), 226 (2011)

[25] Tufvesson P, Annerling A, Hatti-Kaul R, Adlercreutz D, Biotechnol. Bioeng., 97(3), 447 (2007)

[26] Duan ZQ, Du W, Liu DH, Bioresour. Technol., 102(23), 11048 (2011)

[27] Wang X, Jin Q, Wang T, Huang J, Wang X, J. Mol. Catal. B-Enzym., 97, 130 (2013)

[28] Wang X, Wang X, Wang T, J. Agric. Food Chem., 60, 451 (2012)

[29] Kanerva LT, Kosonen M, Vanttinen E, Huuhtanen TT, Dahlqvist M, Acta Chem. Scand., 46, 1101 (1992)