模拟移动床色谱分离二十碳五烯酸乙酯和二十二碳六烯酸乙酯

doi:10.3724/SP.J.1123.2018.04018

色谱 ›› 2018, Vol. 36 ›› Issue (9): 858-865.DOI: 10.3724/SP.J.1123.2018.04018

模拟移动床色谱分离二十碳五烯酸乙酯和二十二碳六烯酸乙酯

董青, 李敏, 杨亦文, 鲍宗必, 杨启炜, 张治国, 任其龙

浙江大学化学工程与生物工程学院, 生物质化工教育部重点实验室, 浙江杭州 310027

收稿日期:2018-04-17 出版日期:2018-09-08 发布日期:2014-08-05
通讯作者: 任其龙,Tel:(0571)87952773,E-mail:renql@zju.edu.cn
基金资助:
国家自然科学基金面上项目（21776240）；国家自然科学基金重点项目（21436010）；浙江省重点科技创新团队计划（2011R50002）.

Separation of eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester by simulated moving bed chromatography

DONG Qing, LI Min, YANG Yiwen, BAO Zongbi, YANG Qiwei, ZHANG Zhiguo, REN Qilong

Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China

Received:2018-04-17 Online:2018-09-08 Published:2014-08-05
Supported by:
National Natural Science Foundation of China (No. 21776240); National Natural Science Foundation of China (No. 21436010); Program for Zhejiang Province Leading Team of S&T Innovation Key (No. 2011R50002).

摘要/Abstract

摘要：

二十碳五烯酸和二十二碳六烯酸是两种非常重要的ω-3多不饱和脂肪酸，广泛用于膳食补充剂和药品，同时它们的生理作用并不完全相同，因此分离制备它们的高纯度单体十分必要。首先以聚苯乙烯/二乙烯基苯（PS/DVB）聚合物为固定相，在液相色谱上分离二十碳五烯酸乙酯（EPA-EE）和二十二碳六烯酸乙酯（DHA-EE），考察了流动相、填料粒径、温度对分离的影响。然后采用粒径20 μ m、孔径10 nm的PS/DVB填料装填了8根150 mm×10 mm的半制备色谱柱，测定了半制备柱装填的均一性。最后尝试在模拟移动床（SMB）色谱上分离EPA-EE和DHA-EE的混合物，探究了Ⅱ区和Ⅲ区的流量、进料流量、进料浓度对分离的影响，结果表明SMB制备的EPA-EE和DHA-EE的相对纯度分别为91.6%和93.6%，回收率分别为97.0%和91.6%，固定相生产率为5.97 g/（L\5h），溶剂消耗为1.52 L/g。SMB制备EPA-EE和DHA-EE具有较大的应用潜力。

关键词: 二十二碳六烯酸乙酯, 二十碳五烯酸乙酯, 分离, 模拟移动床色谱, 液相色谱

Abstract:

Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are important ω -3 polyunsaturated fatty acids. Their physiological effects on humans are not exactly the same; therefore, the production of products with high-purity EPA or DHA monomers is significant. In this work, EPA ethyl ester (EPA-EE) and DHA ethyl ester (DHA-EE) were first separated using HPLC with poly(styrene-co-divinylbenzene) (PS/DVB) as the stationary phase. The effects of the mobile phase, PS/DVB particle diameter, and column temperature were systematically evaluated. The results showed that methanol is a suitable mobile phase, having a resolution of 2.75. By comparing resolutions, a PS/DVB particle diameter of 10 μ m was chosen; however, when the pressure drop of PS/DVB is considered, PS/DVB with a particle diameter of 20 μ m is more favorable for large-scale preparations. A column temperature of 40℃ was found to be the most feasible for maintaining efficient separation. Second, eight semi-preparative columns (150 mm×10 mm) of PS/DVB polymer were prepared for the simulated moving bed (SMB) chromatography; the homogeneity of these columns was perfect, with a relative total column porosity error of less than 1%. Finally, an EPA-EE and DHA-EE mixture was separated using the SMB chromatography, and the contents of the extract and the raffinate were determined using GC-FID. The effects of the flow rate of Zone Ⅱ and Zone Ⅲ, the flow rate of the feed, and the feed concentration were investigated. Under optimal conditions, EPA-EE and DHA-EE with favorable purities of 91.6% and 93.6%, respectively, were achievable. The recovery of the EPA-EE was 97.0% and the recovery of the DHA-EE was 91.6%. The productivity and solvent requirements were 5.97 g/(L\5h) and 1.52 L/g, respectively. Therefore, SMB chromatography is an attractive technology for the production of high-value products.

Key words: docosahexaenoic acid ethyl ester (DHA-EE), eicosapentaenoic acid ethyl ester (EPA-EE), liquid chromatography (LC), separation, simulated moving bed (SMB) chromatography

中图分类号:

O658

董青, 李敏, 杨亦文, 鲍宗必, 杨启炜, 张治国, 任其龙. 模拟移动床色谱分离二十碳五烯酸乙酯和二十二碳六烯酸乙酯[J]. 色谱, 2018, 36(9): 858-865.

DONG Qing, LI Min, YANG Yiwen, BAO Zongbi, YANG Qiwei, ZHANG Zhiguo, REN Qilong. Separation of eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester by simulated moving bed chromatography[J]. Chinese Journal of Chromatography, 2018, 36(9): 858-865.

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模拟移动床色谱分离二十碳五烯酸乙酯和二十二碳六烯酸乙酯

Separation of eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester by simulated moving bed chromatography

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