Concentration of linoleic acid from cottonseed oil by starch complexation

doi:10.1016/j.cjche.2018.07.001

中国化学工程学报 ›› 2019, Vol. 27 ›› Issue (4): 845-849.DOI: 10.1016/j.cjche.2018.07.001

• Separation Science and Engineering • 上一篇下一篇

Concentration of linoleic acid from cottonseed oil by starch complexation

Dan Liang, Yufeng Hu, Weiting Ma, Zhengtang Zhao, Siqi Jiang, Yichuan Wang, Xianming Zhang

State Key Laboratory of Heavy Oil Processing, China University of Petroleum, Beijing 102249, China

收稿日期:2018-05-01 修回日期:2018-06-19 出版日期:2019-04-28 发布日期:2019-06-14
通讯作者: Yufeng Hu
基金资助:
Supported by the National Natural Science Foundation of China (21576285, 21776300 and 21276271), and Innovation Foundation of China University of Petroleum, Beijing (ZX20160004).

Concentration of linoleic acid from cottonseed oil by starch complexation

Dan Liang, Yufeng Hu, Weiting Ma, Zhengtang Zhao, Siqi Jiang, Yichuan Wang, Xianming Zhang

State Key Laboratory of Heavy Oil Processing, China University of Petroleum, Beijing 102249, China

Received:2018-05-01 Revised:2018-06-19 Online:2019-04-28 Published:2019-06-14
Contact: Yufeng Hu
Supported by:
Supported by the National Natural Science Foundation of China (21576285, 21776300 and 21276271), and Innovation Foundation of China University of Petroleum, Beijing (ZX20160004).

摘要/Abstract

摘要： The extraction of linoleic acid from fatty acids (FA) of the cottonseed oil using starch-FA complexes was developed for the first time. We showed that starch can form inclusion complexes of different strengths with FA and that the different strengths stem from the differences in chain length, degree of unsaturation, and position of double bonds of FA. The optimal separation conditions were determined as follows:The inclusion temperature is 69℃, the inclusion time is 30 min, the starch/FA mass ratio is 10:1, and the ratio of the volume of methanol-water solution and the mass of FA is 18:1. Compared to urea inclusion complexation, starch complexation has milder reaction temperature and shorter reaction time. Under these conditions, linoleic acid can be concentrated from 38.9% to 70.04% by one-off extraction. Moreover, the experimental results demonstrate the almost perfect reusability of starch. These results show that starch complexation is a promising method that can be used to obtain highly concentrated linoleic acid from cottonseed oil.

关键词: Starch, Linoleic acid, Starch complexation, Starch-FA complex, Cottonseed oil

Abstract: The extraction of linoleic acid from fatty acids (FA) of the cottonseed oil using starch-FA complexes was developed for the first time. We showed that starch can form inclusion complexes of different strengths with FA and that the different strengths stem from the differences in chain length, degree of unsaturation, and position of double bonds of FA. The optimal separation conditions were determined as follows:The inclusion temperature is 69℃, the inclusion time is 30 min, the starch/FA mass ratio is 10:1, and the ratio of the volume of methanol-water solution and the mass of FA is 18:1. Compared to urea inclusion complexation, starch complexation has milder reaction temperature and shorter reaction time. Under these conditions, linoleic acid can be concentrated from 38.9% to 70.04% by one-off extraction. Moreover, the experimental results demonstrate the almost perfect reusability of starch. These results show that starch complexation is a promising method that can be used to obtain highly concentrated linoleic acid from cottonseed oil.

Key words: Starch, Linoleic acid, Starch complexation, Starch-FA complex, Cottonseed oil

Dan Liang, Yufeng Hu, Weiting Ma, Zhengtang Zhao, Siqi Jiang, Yichuan Wang, Xianming Zhang. Concentration of linoleic acid from cottonseed oil by starch complexation[J]. 中国化学工程学报, 2019, 27(4): 845-849.

Dan Liang, Yufeng Hu, Weiting Ma, Zhengtang Zhao, Siqi Jiang, Yichuan Wang, Xianming Zhang. Concentration of linoleic acid from cottonseed oil by starch complexation[J]. Chinese Journal of Chemical Engineering, 2019, 27(4): 845-849.

参考文献

[1] B.J. Meyer, N.J. Mann, J.L. Lewis, G.C. Milligan, A.J. Sinclair, P.R. Howe, Dietary intakes and food sources of omega-6 and omega-3 polyunsaturated fatty acids, Lipids 38(4) (2003) 391-398.
[2] Z. Lei, W. Arlt, P. Wasserscheid, Separation of 1-hexene and n-hexane with ionic liquids, Fluid Phase Equilib. 241(1-2) (2006) 290-299.
[3] J. Gao, Y. Dai, W. Ma, H. Xu, C. Li, Efficient separation of phenol from oil by acid-base complexing adsorption, Chem. Eng. J. 281(2015) 749-758.
[4] H. Wang, B. Yang, J. Wu, Multi-fields synergy in the process of reactive distillation coupled with membrane separation, Chem. Eng. Process. Process Intensif. 44(11) (2005) 1207-1215.
[5] H.B. Gu, J. Wu, Q. Zhang, W. Yuan, Y. Chen, Concentration of α-linoleic acid of perilla oil by gradient cooling urea inclusion, Agric. Sci. China 8(6) (2009) 685-690.
[6] M.G. Sajilata, R.S. Singhal, M.Y. Kamat, Fractionation of lipids and purification of γ-linolenic acid (GLA) from Spirulinaplatensis, Food Chem. 109(3) (2008) 580-586.
[7] N. Gamez-Meza, J.A. Noriega-Rodrıguez, L.A. Medina-Juárez, J. Ortega-Garcıa, J. Monroy-Rivera, F.J. Toro-Vázquez, O. Angulo-Guerrero, Concentration of eicosapentaenoic acid and docosahexaenoic acid from fish oil by hydrolysis and urea complexation, Food Res. Int. 36(7) (2003) 721-727.
[8] J.B. Brown, Low-temperature crystallization of the fatty acids and glycerides, Chem. Rev. 29(2) (1941) 333-354.
[9] M. Teramoto, H. Matsuyama, N. Ohnishi, S. Uwagawa, K. Nakai, Extraction of ethyl and methyl esters of polyunsaturated fatty acids with aqueous silver nitrate solutions, Ind. Eng. Chem. Res. 33(2) (1994) 341-345.
[10] G.C. Burdge, P. Wright, A.E. Jones, S.A. Wootton, A method for separation of phosphatidylcholine, triacylglycerol, non-esterified fatty acids and cholesterol esters from plasma by solid-phase extraction, Br. J. Nutr. 84(5) (2000) 781-787.
[11] W.W. Christie, Silver ion chromatography using solid-phase extraction columns packed with a bonded-sulfonic acid phase, J. Lipid Res. 30(9) (1989) 1471-1473.
[12] R. Wood, T. Lee, High-performance liquid chromatography of fatty acids:Quantitative analysis of saturated, monoenoic, polyenoic and geometrical isomers, J. Chromatogr. A 254(1983) 237-246.
[13] X. Cao, Y. Ito, Supercritical fluid extraction of grape seed oil and subsequent separation of free fatty acids by high-speed counter-current chromatography, J. Chromatogr. A 1021(1) (2003) 117-124.
[14] C.K. Williams, M.A. Hillmyer, Polymers from renewable resources:A perspective for a special issue of polymer reviews, Polym. Rev. 48(1) (2008) 1-10.
[15] C. Li, X. Zhang, X. He, S. Zhang, Design of separation process of azeotropic mixtures based on the green chemical principles, J. Clean. Prod. 15(7) (2007) 690-698.
[16] H.F. Yang, Y.F. Hu, Separation of para-xylene and meta-xylene by extraction process using aqueous cyclodextrins solution, Chem. Eng. Process. Process Intensif. 116(2017) 114-120.
[17] M.C. Tang, L. Copeland, Analysis of complexes between lipids and wheat starch, Carbohydr. Polym. 67(1) (2007) 80-85.
[18] C.E. Snape, W.R. Morrison, M.M. Maroto-Valer, J. Karkalas, R.A. Pethrick, Solid state ¹³C NMR investigation of lipid ligands in V-amylose inclusion complexes, Carbohydr. Polym. 36(2-3) (1998) 225-237.
[19] F. Chang, X. He, Q. Huang, The physicochemical properties of swelled maize starch granules complexed with Lauric acid, Food Hydrocoll. 32(2) (2013) 365-372.
[20] I. Lalush, H. Bar, I. Zakaria, S. Eichler, E. Shimoni, Utilization of amylose-lipid complexes as molecular nanocapsules for conjugated linoleic acid, Biomacromolecules 6(1) (2005) 121-130.
[21] H.S. Guraya, R.S. Kadan, E.T. Champagne, Effect of rice starch-lipid complexes on in vitro digestibility, complexing index, and viscosity, Cereal Chem. 74(5) (1997) 561-565.
[22] J. Hasjim, S.O. Lee, S. Hendrich, S. Setiawan, Y. Ai, J.L. Jane, Characterization of a novel resistant-starch and its effects on postprandial plasma-glucose and insulin responses, Cereal Chem. 87(4) (2010) 257-262.
[23] M.C. Godet, B. Bouchet, P. Colonna, D.J. Gallant, A. Buleon, Crystalline amylose-fatty acid complexes:Morphology and crystal thickness, J. Food Sci. 61(6) (1996) 1196-1201.
[24] J. Karkalas, S. Ma, W.R. Morrison, R.A. Pethrick, Some factors determining the thermal properties of amylose inclusion complexes with fatty acids, Carbohydr. Res. 268(2) (1995) 233-247.
[25] J. Van Gerpen, Biodiesel processing and production, Fuel Process. Technol. 86(10) (2005) 1097-1107.
[26] W.S. Ratnayake, D.S. Jackson, A new insight into the gelatinization process of native starches, Carbohydr. Polym. 67(4) (2007) 511-529.
[27] A. Star, D.W. Steuerman, J.R. Heath, J.F. Stoddart, Starched carbon nanotubes, Angew. Chem. 41(14) (2002) 2508-2512.
[28] J. Nuessli, J.L. Putaux, P. Le Bail, A. Buléon, Crystal structure of amylose complexes with small ligands, Int. J. Biol. Macromol. 33(4) (2003) 227-234.
[29] M.A. Whittam, P.D. Orford, S.G. Ring, S.A. Clark, M.L. Parker, P. Cairns, M.J. Miles, Aqueous dissolution of crystalline and amorphous amylose-alcohol complexes, Int. J. Biol. Macromol. 11(6) (1989) 339-344.
[30] W. Banks, C.T. Greenwood, Amylose:A non-helical biopolymer in aqueous solution, Polymer 12(2) (1971) 141-145.
[31] W.T. Winter, A. Sarko, Crystal and molecular structure of V-anhydrous amylose, Biopolymers 13(7) (1974) 1447-1460.
[32] M.C. Godet, V. Tran, M.M. Delage, A. Buléon, Molecular modelling of the specific interactions involved in the amylose complexation by fatty acids, Int. J. Biol. Macromol. 15(1) (1993) 11-16.
[33] S. Raphaelides, J. Karkalas, Thermal dissociation of amylose-fatty acid complexes, Carbohydr. Res. 172(1) (1988) 65-82.
[34] J.R. Kanicky, D.O. Shah, Effect of degree, type, and position of unsaturation on the pKa of long-chain fatty acids, J. Colloid Interface Sci. 256(1) (2002) 201-207.
[35] Z. Zhou, K. Robards, S. Helliwell, C. Blanchard, Effect of the addition of fatty acids on rice starch properties, Food Res. Int. 40(2) (2007) 209-214.
[36] K. Kawai, S. Takato, T. Sasaki, K. Kajiwara, Complex formation, thermal properties, and in-vitro digestibility of gelatinized potato starch-fatty acid mixtures, Food Hydrocoll. 27(1) (2012) 228-234.

Concentration of linoleic acid from cottonseed oil by starch complexation

Concentration of linoleic acid from cottonseed oil by starch complexation

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