催化学报 ›› 2014, Vol. 35 ›› Issue (4): 590-598.DOI: 10.1016/S1872-2067(14)60056-5

• 研究论文 • 上一篇    下一篇

氢键的协同作用驱动水中苯甲醛的合成

杨祖金, 纪红兵   

  1. 中山大学化学与化学工程学院, 广东省低碳化学与过程节能实验室, 广东广州510275
  • 收稿日期:2013-11-23 修回日期:2014-01-03 出版日期:2014-03-20 发布日期:2014-03-21
  • 通讯作者: 纪红兵
  • 基金资助:

    国家自然科学基金(21376279,21176268,21036009);广东省重大科技专项(2012A080103005);广东省部产学研结合项目(2011B090400439).

Synergistic effect of hydrogen bonding mediated selective synthesis of benzaldehyde in water

Zujin Yang, Hongbing Ji   

  1. School of Chemistry and Chemical Engineering, Key Laboratory of Low-carbon Chemistry &Energy Conservation of Guangdong Province, Sun Yat-sen University, Guangzhou 510275, Guangdong, China
  • Received:2013-11-23 Revised:2014-01-03 Online:2014-03-20 Published:2014-03-21
  • Supported by:

    This work was supported by the the National Natural Science Foundation of China (21376279, 21176268, 21036009), the Science and Technology Major Program of Guangdong Province (2012A080103005), and Special Project on Integration of Production, Education And Research of Guangdong Province (2011B090400439).

摘要:

以环氧氯丙烷作为交联溶剂合成和表征了纤维素功能化的β-环糊精,考察了这种超分子聚合物作为一种多相催化剂用于苯甲醛的合成的催化性能. 结果表明,该催化剂在温和的反应条件下具有较高的催化活性和选择性,容易恢复和重新利用,且活性没有大的损失. 进一步研究指出,β-环糊精聚合物中的b-环糊精能通过非极性共价键与肉桂醛形成主客包结物,此外,β-环糊精和纤维素的功能基团能与肉桂醛通过O-H…O的氢键形成多重氢键的相互作用,这种氢键的协同作用明显提高了催化剂的性能.

关键词: 纤维素功能化β-环糊精, 氢键, 底物专一性, 肉桂醛氧化, 苯甲醛

Abstract:

β-cyclodextrin-functionalized cellulose was prepared from cellulose and β-cyclodextrin crosslinked with epichlorohydrin. The supramolecular polymer has been used as a heterogeneous catalyst for the synthesis of benzaldehyde under mild reaction conditions with high activity and yield. The catalyst was easily recovered and reused without significant activity loss. The β-cyclodextrin in the polymer formed host-guest complexes with cinnamaldehyde via noncovalent bonding. In addition, multiple interactions were observed between β-cyclodextrin and the substrate via intermolecular O-H…O hydrogen bonding. The significant promotion for the catalytic performance could be attributed to the synergistic effects of hydrogen bonding.

Key words: β-cyclodextrin-functionalized cellulose, Hydrogen bonding, Synergistic effect, Cinnamaldehyde oxidation, Benzaldehyde