中华医学超声杂志

应用化学 ›› 2011, Vol. 28 ›› Issue (11): 1269-1273.DOI: 10.3724/SP.J.1095.2011.00680

• 研究论文 • 上一篇    下一篇

碱性水溶液中单6-氧-对甲苯磺酰-β-环糊精酯的非均相合成

王用良1,2，冯茹森1,2*，郭拥军1,2，吕鑫3   

  1. (1.西南石油大学化学化工学院 成都 610500;2.油气藏地质及开发工程国家重点实验室 成都 610500;
    3.中海石油研究中心技术研究部 北京)
  • 收稿日期:2010-11-16 修回日期:2011-01-18 出版日期:2011-11-10 发布日期:2011-11-10
  • 通讯作者: 冯茹森，讲师; Tel/Fax:028-83037332; E-mail:gs_frs@163.com; 研究方向：提高采收率理论与技术研究
  • 基金资助:
    国家科技重大专项（2008ZX05024）资助项目

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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摘要：

不引入有机溶剂，低温下将对甲苯磺酰氯与β-环糊精在NaOH水溶液中进行非均相反应，得到了单6-氧-对甲苯磺酰β-环糊精酯（6-OTs-β-CD）。 借助1H NMR谱证实了环糊精单磺酰化机理。 考察了产物的水解因素，研究了反应条件对产率的影响。 实验结果表明，投料摩尔比n(CD)∶n(TsCl)=4∶1，碱液浓度0.75 mol/L，反应物质量分数4.7%，反应温度0 ℃，反应5 h时，6位单酯化收率为43.4%。

关键词: 非均相, 氧, 对甲苯磺酰基-β-环糊精, β-环糊精, 对甲苯磺酰氯

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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