固定化磷酸盐选择性催化合成2-O-己二酸单乙烯基蔗糖酯

Regioselective Synthesis of 2-O-Vinyl Adipoyl Sucrose Ester Catalyzed by Immobilized Phosphates

因为蔗糖含有8个反应活性相近的羟基,蔗糖与脂肪酸酯的转酯化反应很难得到单一的产物,本研究以固定化磷酸盐作催化剂可以选择性地催化蔗糖和己二酸二乙烯酯(Divinyladipate,DVA)的转酯化反应。方法是在含有磷酸盐的丙酮中加入酸洗过的硅藻土,振荡1h,可制成固定化磷酸盐;取0.01mol蔗糖和0.02molDVA,加入固定化磷酸盐10g,以100mLDMF为溶剂,在50℃、220r·min-1的恒温摇床中连续反应1d,可以选择性地获得蔗糖单酯产品。转酯化反应的转化率和产率分别达到60.0%、54.8%。经过MS和13C-NMR鉴定,转酯化位置为蔗糖基的C-2位,合成产物为2-O-己二酸单乙烯基蔗糖酯。

Since the sucrose contains eight hydroxyls with similar chemical reactivity, the transesterification of sucrose and fatty acid esters can hardly get single pure product. In our research, the immobilized phosphate with celite as support was prepared by admixing the phosphate with the acid-washed celite in acetone and oscillating them for 1 h. The prepared immobilized phosphate can be used as catalyst to catalyze the transesterification of sucrose and divinyl adipate. Using 10 g prepared immobilized phosphate as catalyst with 100 mL DMF as solvent, the selective transesterification reaction between sucrose （0.01 mol） and divinyl adipate （0.02 mol） was carried out at 50℃ for 1 day in a constant temperature shaking incubator with vibration rate of 200 r·min^-1, and the sucrose monoester can be obtained with the conversion percentage of 60.0% and yield percentage of 54.8%. The above obtained product was characterized by MS and ^13C-NMR, and the results show that the hydroxyl bonded to C-2 of sucrose takes part in the transesterification, and the examined product is 2-O-vinyl adipoyl sucrose ester.