Synthesis of alkyl polyglycosides using SO3H-functionalized ionic liquids as catalysts

Wenliang Wu; Hongshuai Gao; Bin Hai; Binqi Wang; Min Yu; Yi Nie

doi:10.1039/d1ra00337b

Synthesis of alkyl polyglycosides using SO₃H-functionalized ionic liquids as catalysts

RSC Adv. 2021 Apr 20;11(24):14710-14716. doi: 10.1039/d1ra00337b. eCollection 2021 Apr 15.

Authors

Wenliang Wu^{1

2}, Hongshuai Gao^{1

2}, Bin Hai², Binqi Wang², Min Yu², Yi Nie^{1

2}

Affiliations

¹ Beijing Key Laboratory of Ionic Liquids Clean Process, CAS Key Laboratory of Green Process and Engineering, State Key Laboratory of Multiphase Complex System, Institute of Process Engineering, Chinese Academy of Sciences 100190 Beijing China hsgao@ipe.ac.cn ynie@ipe.ac.cn +86-10-82544875 +86-10-82544875.
² Zhengzhou Institute of Emerging Industrial Technology 450046 Zhengzhou China.

Abstract

An effective process for synthesis of alkyl polyglycosides (APG) was developed using SO₃H-functionalized ionic liquids (SFILs) as catalysts. Four SFILs, [PSmim][HSO₄], [PSmim][pTSA], [PSPy][HSO₄] and [PSPy][pTSA], were designed and synthesized for APG synthesis. The results indicated that [PSmim][HSO₄] shows the best catalytic performance among these four SFILs, which has a great agreement with the order of their acidities. When the [PSmim][HSO₄] was used as catalyst, the reaction time could be decreased from 24 h to 8 h, and molar ration of n-octanol to glucose could be decreased from 5 : 1 to 3 : 1 under the optimization reaction conditions. In addition, the [PSmim][HSO₄] could be easily regenerated and recycled at least 5 times with slight decrease in catalytic activity. Moreover, the catalytic mechanism of [PSmim][HSO₄] was further investigated by molecular simulation. The high catalytic activity of [PSmim][HSO₄] is attributed to hydrogen bonds between [PSmim][HSO₄] and glucose and n-octanol, which could accelerate the protonation of glucose and removal of hydrogen ions from the hydroxyl in n-octanol.