Enrichment of nervonic acid in Acer truncatum Bunge oil by combination of two-stage molecular distillation, one-stage urea complexation and five-stage solvent crystallization

doi:10.1016/j.cjche.2022.10.007

中国化学工程学报 ›› 2023, Vol. 59 ›› Issue (7): 61-71.DOI: 10.1016/j.cjche.2022.10.007

• Full Length Article • 上一篇下一篇

Enrichment of nervonic acid in Acer truncatum Bunge oil by combination of two-stage molecular distillation, one-stage urea complexation and five-stage solvent crystallization

Yingxi Gao, Jiayi Shi, Jie Wang, Fan Zhang, Shichao Tian, Zhiyong Zhou, Zhongqi Ren

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China

收稿日期:2022-07-23 修回日期:2022-10-18 出版日期:2023-07-28 发布日期:2023-10-14
通讯作者: Zhiyong Zhou,E-mail:zhouzy@mail.buct.edu.cn;Zhongqi Ren,E-mail:renzq@mail.buct.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (22125802 and 22078010), Beijing Natural Science Foundation (2222017) and Big Science Project from BUCT (XK180301). The authors gratefully acknowledge these grants.

Enrichment of nervonic acid in Acer truncatum Bunge oil by combination of two-stage molecular distillation, one-stage urea complexation and five-stage solvent crystallization

Yingxi Gao, Jiayi Shi, Jie Wang, Fan Zhang, Shichao Tian, Zhiyong Zhou, Zhongqi Ren

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China

Received:2022-07-23 Revised:2022-10-18 Online:2023-07-28 Published:2023-10-14
Contact: Zhiyong Zhou,E-mail:zhouzy@mail.buct.edu.cn;Zhongqi Ren,E-mail:renzq@mail.buct.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (22125802 and 22078010), Beijing Natural Science Foundation (2222017) and Big Science Project from BUCT (XK180301). The authors gratefully acknowledge these grants.

摘要/Abstract

摘要： Nervonic acid is the world's first and only potent substance that can repair damaged nerve fibers and promote nerve cell regeneration with high nutritional value. The wide variety of fatty acids in plant oils and fats with similar structures makes the large-scale separation and purification of high-purity nervonic acid very difficult. A new combined process of molecular distillation, urea inclusion and solvent crystallization was established to prepare high-purity nervonic acid with the mixed fatty acids obtained after saponification and acidification of Acer truncatum Bunge oil as raw materials. First, according to the difference in the mean free path of fatty acids, molecular distillation was used to separate and remove C16 saturated fatty acid of palmitic acid and four C18-C20 fatty acids of stearic, oleic, linoleic, and linolenic acids. The content of C16-C20 fatty acids decreased from 72.92% to 19.22% after two-stage molecular distillation processes, in which the contents of saturated fatty acid of palmitic acid decreased to about 0.5%. Then, according to the difference in carbon chain length and saturation of fatty acid, the contents of C22-C24 saturated fatty acids of tetracosanoic and docosanoic acids decreased to 0.21% and 0.07% by urea inclusion with urea/free fatty acid preparation by saponification (SPOMFs) ratio as 0.6. In addition, all saturated fatty acids were basically separated. Finally, according to the difference in the solubility of fatty acids in solvents, the C18-C20 unsaturated fatty acids of oleic, linoleic, and linolenic acids and C22 unsaturated fatty acid of erucic acid were removed by solvent crystallization. The content of C18-C20 unsaturated fatty acids decreased to less than 5% with pentanol as the solvent after the first stage solvent crystallization. The content of erucic acid decreased to 3.47% with anhydrous ethanol as the solvent after the second to fifth stage solvent crystallization. The combined process of molecular distillation, urea inclusion and low temperature crystallization innovatively adopted an efficient, simple and easy-to-industrial solvent crystallization method to separate erucic and nervonic acids, obtaining nervonic acid with purity of 96.53% and final yield of 47.99%.

关键词: Nervonic acid, Acer truncatum Bunge, Molecular distillation, Urea complexation, Solvent crystallization

Abstract: Nervonic acid is the world's first and only potent substance that can repair damaged nerve fibers and promote nerve cell regeneration with high nutritional value. The wide variety of fatty acids in plant oils and fats with similar structures makes the large-scale separation and purification of high-purity nervonic acid very difficult. A new combined process of molecular distillation, urea inclusion and solvent crystallization was established to prepare high-purity nervonic acid with the mixed fatty acids obtained after saponification and acidification of Acer truncatum Bunge oil as raw materials. First, according to the difference in the mean free path of fatty acids, molecular distillation was used to separate and remove C16 saturated fatty acid of palmitic acid and four C18-C20 fatty acids of stearic, oleic, linoleic, and linolenic acids. The content of C16-C20 fatty acids decreased from 72.92% to 19.22% after two-stage molecular distillation processes, in which the contents of saturated fatty acid of palmitic acid decreased to about 0.5%. Then, according to the difference in carbon chain length and saturation of fatty acid, the contents of C22-C24 saturated fatty acids of tetracosanoic and docosanoic acids decreased to 0.21% and 0.07% by urea inclusion with urea/free fatty acid preparation by saponification (SPOMFs) ratio as 0.6. In addition, all saturated fatty acids were basically separated. Finally, according to the difference in the solubility of fatty acids in solvents, the C18-C20 unsaturated fatty acids of oleic, linoleic, and linolenic acids and C22 unsaturated fatty acid of erucic acid were removed by solvent crystallization. The content of C18-C20 unsaturated fatty acids decreased to less than 5% with pentanol as the solvent after the first stage solvent crystallization. The content of erucic acid decreased to 3.47% with anhydrous ethanol as the solvent after the second to fifth stage solvent crystallization. The combined process of molecular distillation, urea inclusion and low temperature crystallization innovatively adopted an efficient, simple and easy-to-industrial solvent crystallization method to separate erucic and nervonic acids, obtaining nervonic acid with purity of 96.53% and final yield of 47.99%.

Key words: Nervonic acid, Acer truncatum Bunge, Molecular distillation, Urea complexation, Solvent crystallization

Yingxi Gao, Jiayi Shi, Jie Wang, Fan Zhang, Shichao Tian, Zhiyong Zhou, Zhongqi Ren. Enrichment of nervonic acid in Acer truncatum Bunge oil by combination of two-stage molecular distillation, one-stage urea complexation and five-stage solvent crystallization[J]. 中国化学工程学报, 2023, 59(7): 61-71.

参考文献

[1] T.Q. Yang, Q. Yu, W. Xu, D.Z. Li, F. Chen, A.Z. Liu, Transcriptome analysis reveals crucial genes involved in the biosynthesis of nervonic acid in woody Malania oleifera oilseeds, BMC Plant Biol. 18 (1) (2018) 247.
[2] R.K. Wang, J.S. Fan, P. Chang, L. Zhu, M.R. Zhao, L.L. Li, Genome survey sequencing of Acer truncatum Bunge to identify genomic information, simple sequence repeat (SSR) markers and complete chloroplast genome, Forests 10(2) (2019) 87.
[3] J.R. Sargent, K. Coupland, R. Wilson, Nervonic acid and demyelinating disease, Med. Hypotheses 42 (4) (1994) 237-242.
[4] J. Farquharson, E.C. Jamieson, R.W. Logan, W.J.A. Patrick, A.G. Howatson, F. Cockburn, Docosahexaenoic and nervonic acids in term and preterm infant cerebral white matter, Prenat. Neonat. Med. 42 (1996) 234-240.
[5] Y. Yamazaki, K. Kondo, R. Maeba, M. Nishimukai, T. Nezu, H. Hara, The proportion of nervonic acid in serum lipids is associated with serum plasmalogen levels and metabolic syndrome, J. Oleo Sci. 5(63) (2014) 527-537.
[6] D.D. Hu, Y.J. Cui, J. Zhang, Nervonic acid ameliorates motor disorder in mice with Parkinson's disease, Neurochem. J. 15 (3) (2021) 317-324.
[7] K. Tanaka, T. Shimizu, Y. Ohtsuka, Y. Yamashiro, K. Oshida, Early dietary treatments with Lorenzo’s oil and docosahexaenoic acid for neurological development in a case with Zellweger syndrome, Brain Dev. 29 (9) (2007) 586-589.
[8] E. Chivandi, B.C. Davidson, K.H. Erlwanger, A comparison of the lipid and fatty acid profiles from the kernels of the fruit (nuts) of Ximenia caffra and Ricinodendron rautanenii from Zimbabwe, Ind. Crops. Prod. 27(1) (2008) 29-32.
[9] C.C. Akoh, C.O. Moussata, Characterization and oxidative stability of enzymatically produced fish and canola oil-based structured lipids, J. Am. Oil Chem. Soc. 78 (1) (2001) 25-30.
[10] W.J. Bettger, M.L. McCorquodale, C.B. Blackadar, The effect of a Tropaeolum speciosum oil supplement on the nervonic acid content of sphingomyelin in rat tissues, J. Nutr. Biochem. 12 (8) (2001) 492-496.
[11] D.A. Evans, D.A. Bennett, R.S. Wilson, J.L. Bienias, M.C. Morris, P.A. Scherr, Incidence of Alzheimer disease in a biracial urban community: Relation to apolipoprotein E allele status, Arch. Neurol. 60 (2003) 185-189.
[12] M. Austin, A. Lindesy, W. Rosaline, Hippocampal metabolites with neuroimaging outcomes in the piglet, FASEB J. 10 (29) (2015) 754-755.
[13] Q. Li, J. Chen, X.Z. Yu, J.M. Gao, A mini review of nervonic acid: Source, production, and biological functions, Food Chem. 301 (2019) 125286.
[14] M. Tsujimoto, New fatty acids in shark-liver oil, J. Am. Oil Chem. Soc. 46 (1926) 385-388.
[15] Z. Klenk, A new cerebroside from the brain, Physiol. Chem. 145 (1925) 244-260.
[16] T.F. Tang, X.M. Liu, M. Ling, F. Lai, L. Zhang, Y.H. Zhou, R.R. Sun, Constituents of the essential oil and fatty acid from Malania oleifera, Ind. Crops. Prod. 43 (2013) 1-5.
[17] V. Katavic, E. Mietkiewska, D.C. Taylor, Y.M. Guo, J.M. Brost, Lunaria annua, Cardamine graeca and Teesdalia nudicaulis FAE genes and their use in producing nervonic and eicosenoic acids in seed oils, Patent Application Publication, United States Pat., 8269062 (2010).
[18] D.X. Huai, Y.Y. Zhang, C.Y. Zhang, E.B. Cahoon, Y.M. Zhou, Combinatorial effects of fatty acid elongase enzymes on nervonic acid production in Camelina sativa, PloS One 10(6) (2015) e0131755.
[19] P. Hu, X.B. Xu, L.L. Yu, Physicochemical properties of Acer truncatum seed oil extracted using supercritical carbon dioxide, J. Am. Oil Chem. Soc. 94 (6) (2017) 779-786.
[20] Q. Qiao, X. Wang, H.J. Ren, K. An, Z. Feng, T.T. Cheng, Z.K. Sun, Oil content and nervonic acid content of Acer truncatum seeds from 14 regions in China, Hortic. Plant J. 5 (1) (2019) 24-30.
[21] F.L. Chen, Q. Zhang, S.M. Fei, H.Y. Gu, L. Yang, Optimization of ultrasonic circulating extraction of samara oil from Acer saccharum using combination of Plackett-Burman design and Box-Behnken design, Ultrason. Sonochem. 35 (Pt A) (2017) 161-175.
[22] Y. Zhang, X.L. Hou, Separation and purification of ethyl neurate in Acer truncatum Bunge oil, China Oil 35(1) (2010) 28-31 (in Chinese).
[23] S.S. Liu, Extraction and purification of nervonic acid and effect on the repair of myelin sheath injury in mice with encephalomyelitis, Tianjin University of Science and Technology, China, 2020 (in Chinese).
[24] L. Vázquez, C.C. Akoh, Enrichment of stearidonic acid in modified soybean oil by low temperature crystallisation, Food Chem. 130 (1) (2012) 147-155.
[25] X.Y. Cheng, Y.Q. Huang, Z.Z. Yang, T. Wang, X.S. Wang, Enrichment of palmitoleic acid by a combination of two-step solvent crystallization and molecular distillation, J. Oleo Sci. 70(5) (2021) 599-606.
[26] Á.G. Solaesa, M.T. Sanz, M. Falkeborg, S. Beltrán, Z. Guo, Production and concentration of monoacylglycerols rich in omega-3 polyunsaturated fatty acids by enzymatic glycerolysis and molecular distillation, Food Chem. 190 (2016) 960-967.
[27] Y. Zhang, X.S. Wang, D. Xie, S. Zou, Q.Z. Jin, X.G. Wang, Synthesis and concentration of 2-monoacylglycerols rich in polyunsaturated fatty acids, Food Chem. 250 (2018) 60-66.
[28] Y. Miyagawa, M. Yoshida, Y. Chizawa, S.J. Adachi, Induction periods for lipid crystallization of various vegetable oils, J. Oleo Sci. 68(1) (2019) 45-52.
[29] J. Cheng, L.J. Liu, L.X. Huang, C.H. Zhang, P.J. Xie, Y.J. Deng, K.H. Tang, Mass transfer modeling of α-eleostearic acid from tung oil concentration by low-temperature crystallization, ChemistrySelect 5 (15) (2020) 4715-4721.
[30] D.Y. Xiong, X.M. Liu, W.G. Li, M.J. Liu, Study on solvent selection for separation of nervous acids from alli fructus oil by crystallization, J. Guangxi Univ. 29(1) (2004) 87-88 (in Chinese).
[31] Q.F. Zhou, Study on the preparation technology of nervonic acid from the seeds of garlic head, Zhejiang University, China, 2017 (in Chinese).

Enrichment of nervonic acid in Acer truncatum Bunge oil by combination of two-stage molecular distillation, one-stage urea complexation and five-stage solvent crystallization

Enrichment of nervonic acid in Acer truncatum Bunge oil by combination of two-stage molecular distillation, one-stage urea complexation and five-stage solvent crystallization

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 3

编辑推荐

Metrics

本文评价

[1]	Cui-Ping Ye, Ya-Fei Qiao, Rui-Nan Wang, Wen-Ying Li. Purification of carbazole by solvent crystallization under two forced cooling modes[J]. 中国化学工程学报, 2021, 35(7): 173-179.
[2]	Jiang Yu, Xigang Yuan, Aiwu Zeng. A novel purification process for dodecanedioic acid by molecular distillation[J]. , 2015, 23(3): 499-504.
[3]	黄科林, 吴睿, 曹妍, 李会泉, 王金淑. Recycling and Reuse of Ionic Liquid in Homogeneous Cellulose Acetylation[J]. Chinese Journal of Chemical Engineering, 2013, 21(5): 577-584.