Hang Song

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Organization: Sichuan University
Department: Department of Pharmaceutical and Biological Engineering, College of Chemical Engineering
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Co-reporter:Xiaoxia Huang, Haoran Wu, Zhixia Wang, Yingjie Luo, Hang Song
Journal of Chromatography A 2017 Volume 1479(Volume 1479) pp:
Publication Date(Web):6 January 2017
DOI:10.1016/j.chroma.2016.12.012
•A series of new dication imidazolium-based chiral ionic liquids were synthesized.•Novel solid-liquid two-phase systems based on the chiral ionic liquids were developed.•Excellent effect on enantiomeric separation of racemic phenylalanine was achieved with e.e. 99.2% and yield 85.2% for L-enantiomer in solid phase.•The separation process is characteristic of no organic solvent, simple operation and fast separation process.A novel solid-liquid two-phase system was developed for the chiral separation of racemic phenylalanine with new dication imidazolium-based chiral ionic liquids. Preliminary experiments showed distinct enantioselectivity in amino acid extraction with the novel solid-liquid two-phase system, more L-enantiomer of amino acid cooperatively interacted with ionic liquids and copper ions to be the solid phase. Various factors, including the alkyl chain length of cations of ionic liquids, the amount of copper acetate, the ratio of n(ILs)/n(Cu2+), the amount of water and racemic phenylalanine, the resolution time together with the resolution temperature, were systematically investigated for their influence on resolution efficiency. The results showed that, under a certain condition, the enantiomeric excess value and the yield of phenylalanine in liquid phase (mainly containing D-enantiomer) were 67.8% and 96.5%, the enantiomeric excess value and the yield of phenylalanine in solid phase (mainly containing L-enantiomer) were 99.2% and 85.2%. Finally, 2D NMR technology, infrared spectroscopy and molecular simulation method were used to study the interaction mechanism. The results indicated that L-enantiomer of phenylalanine interacts more strongly with chiral ILs and Cu2+. The novel system has characteristics of free-organic solvent, simple operation, fast separation process and very high resolution efficiency for racemic phenylalanine. This work could provide a new and alternative resolution approach for other chiral separations.
Co-reporter:Dao-Cai Wang, Shun Yao, Yu Cao, Tian Yao, Hang Song
The Journal of Chemical Thermodynamics 2016 Volume 92() pp:55-59
Publication Date(Web):January 2016
DOI:10.1016/j.jct.2015.08.015
•The customised apparatus was in a homogeneous steady heating within sampling continuously.•The saturated vapour pressures data of ZE-3-pentenenitrile are reported.•(Vapour + liquid) equilibrium (VLE) data for the binary system at P = (50 and 100) kPa were measured.•The activity coefficients and the reduced excess molar Gibbs energy were calculated by Margules equation.In this work, great efforts have been made to achieve the large-scale industrial separation of RS-4-vinyl-1-cyclohexene and ZE-3-pentenenitrile. Initially, the vapour pressures of ZE-3-pentenenitrile were determined. The experimental values were correlated by an Antoine-type equation, and the predicted results of vapour pressures showed that the average relative deviation from experimental values was 0.254% for ZE-3-pentenenitrile. Then the isobaric (vapour + liquid) equilibria data of RS-4-vinyl-1-cyclohexene and ZE-3-pentenenitrile were determined at (50.0 and 100.0) kPa. These experimental values were found to be thermodynamically consistent, by means of the point-to-point test and the direct test methods. Two liquid phase activity coefficient models (Wilson and NRTL) were used to correlate the (vapour + liquid) equilibria data of the binary system, and the model parameters were obtained. All models represent the experimental values quite well. The activity coefficients and the reduced excess molar Gibbs energy were calculated by Margules equation, which were found to be in satisfactory agreement with the experimental values.
Co-reporter:Chunmei Jia; Yu Cao; Tao Zuo; Rong Hu; Tian Yao
Journal of Chemical & Engineering Data 2015 Volume 60(Issue 4) pp:999-1005
Publication Date(Web):March 2, 2015
DOI:10.1021/je500762n
The solubility of benzothiazolium ionic liquids in water and in furfural was determined by static analytical and dynamic methods, respectively. The solid–liquid equilibrium data were correlated by using the nonrandom two-liquid (NRTL), Wilson, modified Apelblat, and λh models, respectively. Among the models, the modified Apelblat gave the best correlation results with the average relative deviation (ARD) of 2.02%. The effect of alkyl chain length on the solubility was discussed. The (liquid + liquid) phase equilibrium was observed in the system of benzothiazolium ionic liquids and water below the melting temperature of the ionic liquid. The solubility of benzothiazolium ionic liquids in furfural was much higher than in water, indicating the potential of application in extraction of furfural from aqueous solution.
Co-reporter:Dao-Cai Wang, Yong-Mei Xie, Chen Fan, Shun Yao, Hang Song
Chinese Chemical Letters 2014 Volume 25(Issue 7) pp:1011-1013
Publication Date(Web):July 2014
DOI:10.1016/j.cclet.2014.04.026
A series of novel 2-amino-4H-pyran derivatives have been synthesized via a three-component reaction of α, β-unsaturated ketone derivatives, malononitrile, aldehydes in excellent yields, using DBU as a catalyst and ethanol as a cheap, safe, and environmentally benign solvent under mild conditions. Their antitumor activity was evaluated in three human tumor cell lines, including human colon cancer (HCT116), human cervical cancer (Hela), and non-small cell lung cancer (H1975).A series of novel 2-amino-4H-pyran derivatives have been synthesized via a three-component reaction of α, β-unsaturated ketone derivatives, malononitrile, aldehydes in excellent yields, using DBU as a catalyst and ethanol as a cheap, safe, and environmentally benign solvent under mild conditions. Their antitumor activity was evaluated in three human tumor cell lines, including human colon cancer (HCT116), human cervical cancer (Hela), and non-small cell lung cancer (H1975).
Co-reporter:WeiXia Zhu;QuanYi Wang;KaiFeng Du;Shun Yao
Science Bulletin 2013 Volume 58( Issue 27) pp:3390-3397
Publication Date(Web):2013 September
DOI:10.1007/s11434-013-5782-6
Novel tentacle-type chiral adsorbent based on silica gels modified with β-cyclodextrin (β-CD) and polyvinyl alcohol(PVA) is synthesized by surface grafting technique. The adsorption behavior of chiral pharmaceuticals using the resulting adsorbents is investigated. In the study, FT-IR and thermogravimetric analysis (TGA) are employed to characterize the chemical and physical properties of the adsorbent; mandelic acid (MA) serves as model solute to evaluate the sorption capacity and selectivity of the adsorbent. The experimental results show that the novel tentacle-type adsorbent is possessed of larger equilibrium adsorption capacity and better selectivity over the conventional one and could be as potential chiral stationary phase (CSPs).
Co-reporter:Xinying Li;Shun Yao;Bin Tu;Xue Li;Chunmei Jia
Journal of Separation Science 2010 Volume 33( Issue 9) pp:1216-1223
Publication Date(Web):
DOI:10.1002/jssc.200900567

Abstract

The flavonoids and anthocyanins in Chinese sugarcane (Saccharum sinensis Roxb.) tips, stems, roots and leaves were separately analyzed by HPLC-UV diode array detector, respectively. The results indicated that the content of flavonoids in sugarcane leaves was considerably high in comparison with previous reports in Brazil sugarcane (S. officinarum L.) leaves. Moreover, the content of flavonoids in sugarcane tips and roots was also high in comparison with sugarcane stems. For another, the content of anthocyanins in sugarcane roots was higher than that in other parts of the sugarcane, such as leaves, tips and stems. In addition, two anthocyanins, named petunidin 3-O-(6″-succinyl)-rhamnoside and cyanidin-3-O-glucoside, were first identified from S. sinensis by HPLC-UV diode array detector and HPLC-MS/MS.

Co-reporter:Yongmei Xie, Yiwen Zhang, Wenli Zheng, Chao Fu, Hang Song
Tetrahedron: Asymmetry 2009 Volume 20(Issue 2) pp:175-178
Publication Date(Web):12 February 2009
DOI:10.1016/j.tetasy.2009.01.015
3-METHYL-1-[6-(3-METHYL-1,2-DIHYDROIMIDAZOL-1-IUM-1-YL)HEXYL]-1,2-DIHYDROIMIDAZOL-1-IUM;DIBROMIDE
Caspase-9
Mitogen-activated protein kinase
1H-Imidazolium, 1,1'-(1,3-propanediyl)bis[3-methyl-, dibromide
GENIPOSIDIC ACID
(+)-Genipin