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Cellulose

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Efficient transesterification reaction of cellulose with vinyl esters in DBU/DMSO/CO2 solvent system at low temperature

  • Huaxin Chen
  • Fahui Yang
  • Jiehao Du
  • Haibo Xie
  • Lihua Zhang
  • Yuanlong Guo
  • Qinqin Xu
  • Qiang Zheng
  • Nanwen Li
  • Yu Liu
Original Paper
  • 48 Downloads

Abstract

The transesterification reaction between cellulose and vinyl esters is regarded as a clean and facile strategy for the tunable synthesis of cellulose esters. In this study, a series of cellulose esters with degrees of substitution from 0.58 to 3.0 have been prepared successfully under mild conditions without adding any external catalysts when cellulose was dissolved in the 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)/DMSO/CO2 solvent system and then followed by adding equimolar amounts of long chain fatty, aromatic, branched and steric vinyl esters. The optimization study of different reaction parameters like reaction time, temperature and amounts of substrates demonstrates that the reaction can proceed smoothly even at room temperature. This is evidenced by a cellulose benzoate with a DS of 2.6 obtained when the reaction is performed at 25 °C in 4 h. The as-prepared cellulose esters structure has been confirmed by 1H NMR, 13C NMR and FTIR, and material thermal properties were evaluated by DSC and TGA for an in-depth understanding the relationship between the cellulose esters structure and properties. It is believed that the DBU not only acts as a reagent for the CO2-derivative dissolution of cellulose in DMSO, but also acts as an in situ organocatalyst for the subsequent transesterification reaction.

Graphical abstract

Cellulose esters have been prepared successfully at low temperature using long chain fatty acids, aromatic, branched and steric vinyl esters as acyl donors in the DMSO/DBU/CO2 solvents system, and the DBU not only acts as reagents for the CO2-derivative dissolution of cellulose in DMSO, acts as an organocatalyst for the subsequent derivatisation.

Keywords

Cellulose dissolution Cellulose esters Vinyl ester Organocatalysis Transesterification 

Notes

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Grant No. 31270637 and 21574030); Science and Technology Department of Guizhou Province (Grant No. Natural Science Key Fund [2016]1402), (Grant No. Platform & Talents [2016]5652); Open research fund of Key Laboratory of Pulp and Paper Science & Technology of Ministry of Education of China (08031339); Foundation of State Key Laboratory of Coal Conversion (Grant No. J17-18-907); Excellent Scientific Innovative Talent Programme from Education Department of Guizhou Province (Grant No. KY[2015]479).

Compliance with ethical standards

Conflicts of interest

There are no conflicts to declare.

Supplementary material

10570_2018_2078_MOESM1_ESM.docx (1.8 mb)
Supplementary material 1 (DOCX 1836 kb)

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Huaxin Chen
    • 1
  • Fahui Yang
    • 1
  • Jiehao Du
    • 1
  • Haibo Xie
    • 1
  • Lihua Zhang
    • 1
  • Yuanlong Guo
    • 1
  • Qinqin Xu
    • 1
  • Qiang Zheng
    • 1
  • Nanwen Li
    • 2
  • Yu Liu
    • 3
  1. 1.Department of Polymer Materials and Engineering, College of Materials and MetullurgyGuizhou UniversityGuiyangChina
  2. 2.Key Laboratory of Pulp and Paper Science and Technology of Ministry of Education of ChinaQilu University of TechnologyJinanChina
  3. 3.State Key Laboratory of Coal Conversion, Institute of Coal ChemistryChinese Academy of SciencesTaiyuanChina

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