Synthesis of cellulose benzoates under homogeneous conditions in an ionic liquid |
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Authors: | Jinming Zhang Jin Wu Yan Cao Shengmei Sang Jun Zhang Jiasong He |
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Institution: | (1) Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Engineering Plastics (KLEP), Joint Laboratory of Polymer Science and Materials, Institute of Chemistry, Chinese Academy of Sciences (CAS), 100190 Beijing, China |
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Abstract: | The ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl) as a reaction medium was studied for the synthesis of cellulose
benzoates by homogeneous acylation of dissolved cellulose with benzoyl chlorides in the absence of any catalysts. Cellulose
benzoates with a degree of substitution (DS) in the range from about 1 to 3.0 were accessible under mild conditions. The DS
of cellulose derivatives increased with the increase of the molar ratio of benzoyl chloride/anhydroglucose unit (AGU) in cellulose,
reaction time, and reaction temperature. Benzoylation of cellulose with some 4-substituted benzoyl chlorides including 4-toluoyl
chloride, 4-chlorobenzoyl chloride and 4-nitrobenzoyl chloride was also readily carried out under mild conditions. Furthermore,
regioselectively substituted mixed cellulose esters were synthesized in this work. All products were characterized by means
of FT-IR, 1H-NMR, and 13C-NMR spectroscopy. In addition, at the end of benzoylation of cellulose, the ionic liquid AmimCl was easily recycled. When
the recycled AmimCl was used as the reaction media, the cellulose benzoate with a similar DS was obtained under comparable
reaction conditions. |
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Keywords: | Cellulose benzotates Chiral stationary phases Homogeneous acylation Ionic liquid Regioselectively substituted mixed cellulose esters |
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