Citation: CHEN Tao, CHEN Xiange, XU Junye, FAN Jun, YU Ying, ZHANG Weiguang. Enantioseparation of metalaxyl racemate by simulated moving bed chromatography[J]. Chinese Journal of Chromatography, ;2016, 34(1): 68-73. doi: 10.3724/SP.J.1123.2015.10024 shu

Enantioseparation of metalaxyl racemate by simulated moving bed chromatography

CHEN Tao ¹ ,
CHEN Xiange ¹ ,
XU Junye ² ,
FAN Jun ^1,, ,
YU Ying ¹ ,
ZHANG Weiguang ^1,2,,

1.
1. School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China;
2.
2. Guangzhou Research & Creativity Biotechnology Co. Ltd., Guangzhou 510663, China

Corresponding author: FAN Jun, ZHANG Weiguang,
Received Date: 16 October 2015

Fund Project: 国家自然科学基金项目(21171059,21275056) (21171059,21275056)科技部中小型企业技术创新基金项目(13C26214404534) (13C26214404534)广东省科技计划项目(2014A010101145,2012B010900043) (2014A010101145,2012B010900043)广州市科技计划项目(2013J4400027,201508020093). (2013J4400027,201508020093)

Due to some advantages such as high precision, high efficiency and low consumption of organic solvents, chromatographic separation technique by simulated moving bed (SMB) has attracted considerable attention in the past decades. Herein, the enantioseparation of metalaxyl racemate on EnantioPak OD columns has been carried out by SMB chromatography with the mixture of hexane-ethanol (70 : 30, v/v). The elution order of two metalaxyl enantiomers under current chromatographic conditions was determined by HPLC with the optical rotation detector. Then, the influence of running parameters, such as the concentration, flow rate and switch time on the resolution of metalaxyl racemate has been studied in detail. In addition, the separation results from SMB and the preparative chromatography have been compared under the same concentrations. The results showed that the retention of S-(+)-metalaxyl was weaker than R-(-)-metalaxyl and S-(+)-metalaxyl was eluted first. Most importantly, metalaxyl racemate was well separated by SMB chromatography under linear or non-linear conditions, and the purity of each enantiomer product was over 99%. Furthermore, the amount separated by SMB was much more than by the preparative chromatography with racemate concentration of 15 mg/mL, and the mobile phase consumption was one-ninth of the latter. In brief, these results provide us important information for the future development of large-scale chromatographic separation of metalaxyl enantiomers.
- simulated moving bed (SMB) chromatography,
- elution volume approach,
- chiral separation,
- metalaxyl,
- elution order
1. [1]
  [1] Rajendran A, Paredes G, Mazzotti M. J Chromatogr A, 2009, 1216(4): 709
2. [2]
  [2] Ma Y, Chen L H, Lu X T, et al. Ecotox Environ Safety, 2009, 72(7): 1913
3. [3]
  [3] Ye J, Zhao M R, Liu J, et al. Environ Pollut, 2010, 158(7): 2371
4. [4]
  [4] Shen J, Okamoto Y. Chem Rev, 2015, DOI: 10.1021/acs. chemrev.5b00317
5. [5]
  [5] Shen J, Ikai T, Okamoto Y. J Chromatogr A, 2014, 1363: 51
6. [6]
  [6] Tu H S, Fan J, Tan Y, et al. Chinese Journal of Chromatography, 2014, 32(5): 452 涂鸿盛, 范军, 谭艺, 等. 色谱, 2014, 32(5): 452
7. [7]
  [7] Mazzotti M, Storti G, Morbidelli M. J Chromatogr A, 1997, 769(1): 3
8. [8]
  [8] Aniceto J P S, Silva C M. Sep Purif Rev, 2015, 44(1): 41
9. [9]
  [9] Migliorini C, Gentilini A, Mazzotti M, et al. Ind Eng Chem Res, 1999, 38(10): 2400
10. [10]
  [10] Pedeferri M, Zenoni G, Mazzotti M, et al. Chem Eng Sci, 1999, 54(17): 3735
11. [11]
  [11] Juza M, Mazzotti M, Morbidelli M. Trends Biotechnol, 2000, 18(3): 108
12. [12]
  [12] Langel C, Grossmann C, Jermann S, et al. Ind Eng Chem Res, 2010, 49(23): 11996
13. [13]
  [13] Cavoy E, Deltent M F, Lehoucq S, et al. J Chromatogr A, 1997, 769(1): 49
14. [14]
  [14] Fuereder M, Panke S, Bechtold M. J Chromatogr A, 2012, 1236: 123
15. [15]
  [15] Wang X, Ching C B. Chem Eng Sci, 2005, 60(5): 1337
16. [16]
  [16] Jermann S, Alberti A, Mazzotti M. J Chromatogr A, 2014, 1364: 107
17. [17]
  [17] C mara L D T. Chem Eng Technol, 2014, 37(2): 301
18. [18]
  [18] Li Y B, Dong F S, Liu X G, et al. Food Chem, 2013, 141(1): 10
19. [19]
  [19] Zadra C, Marucchini C, Zazzerini A. J Agric Food Chem, 2002, 50(19): 5373
20. [20]
  [20] Wei F, Li M, Huang F M, et al. J Chromatogr A, 2011, 1218(20): 2906
21. [21]
  [21] Wei F, Shen B, Chen M J, et al. Ind Eng Chem Res, 2012, 51(16): 5805
22. [22]
  [22] Soepriatna N, Wang N H L, Wankat P C. Adsorption, 2014, 20(1): 37
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