Chinese Journal of Applied Chemistry

Chinese Journal of Applied Chemistry ›› 2011, Vol. 28 ›› Issue (11): 1269-1273.DOI: 10.3724/SP.J.1095.2011.00680

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Heterogeneous Synthesis of Mono 6-Deoxy-tosyl-β-cyclodextrin in Alkaline

WANG Yongliang1,2, FENG Rusen1,2*, GUO Yongjun1,2, LV Xin3   

  1. (1.School of Chemistry and Chemical Engineering,Southwest Petroleum University,Chengdu 610500;
    2.State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation,
    Southwest Petroleum University,Chengdu 610500;
    3.Technology Research Department,CNOOC Research Center,Beijing)
  • Received:2010-11-16 Revised:2011-01-18 Published:2011-11-10 Online:2011-11-10

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Abstract:

Employing heterogeneous reaction, 6-deoxy-tosyl-β-cyclodextrin(6-OTs-β-CD) was prepared by the reaction of β-CD with p-toluenesulfonyl chloride at low temperature in sodium hydroxide aqueous solution. The compound has been characterized by means of UV-Vis, IR, 1H NMR and 13C NMR spectroscopies. The mechanism of cyclodextrin mono tosylation was confirmed by 1H NMR. The effect of hydrolysis factors on product and the influence of reaction conditions on the yield were investigated. Under optimal reaction conditions molar ratio of reactant n(TsCl)∶n(CD)=4∶1, alkali concentration 0.75 mol/L, mass fraction of reactants 4.7%, reaction temperature 0 ℃ and reaction time 5 h, a yield of 43.4% can be obtained.

Key words: heterogeneous system, deoxy-tosyl-β-cyclodextrin,β-cyclodextrin,p-toluenesulfonyl chloride

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