Synthesis of allyl cellulose in NaOH/urea aqueous solutions and its thiol–ene click reactions†,Polymer Chemistry

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Synthesis of allyl cellulose in NaOH/urea aqueous solutions and its thiol–ene click reactions†
Polymer Chemistry ( IF 4.1 ) Pub Date : 2015-03-17 00:00:00 , DOI: 10.1039/c5py00301f
Haoze Hu _{1,

2,

3} , Jun You _{1,

2,

3} , Weiping Gan _{1,

2,

3} , Jinping Zhou _{1,

2,

3} , Lina Zhang _{1,

2,

3}

Affiliation

Allyl celluloses (ACs) were synthesized by the reaction of cellulose with allyl chloride in NaOH/urea aqueous solutions. The reaction started homogeneously and ended heterogeneously. The structure and properties of ACs were characterized with SEC-LLS, NMR and solubility testing. The results demonstrated that organo-soluble AC, with a degree of substitution of 0.98–1.65, could be obtained by adjusting the molar ratio of allyl chloride to the anhydroglucose unit of cellulose. A capability evaluation of the click reaction of AC was performed by selecting four thiol compounds. AC-click products were characterized with FT-IR, NMR and elemental analysis, and the results indicated few impurities or substructures resulting from side reactions. The click reaction displayed a high conversion rate, and all the AC-click products demonstrated high solubility in certain solvents. This work provides a facile method for the synthesis of AC in an aqueous system and shows a novel stage for the mild and diverse derivatization of cellulose.

中文翻译：

NaOH /脲水溶液中烯丙基纤维素的合成及其硫醇-烯点击反应†

通过纤维素与烯丙基氯在NaOH /脲水溶液中的反应合成烯丙基纤维素（ACs）。反应均匀地开始并且异质地结束。通过SEC-LLS，NMR和溶解度测试对AC的结构和性质进行了表征。结果表明，通过调节烯丙基氯与纤维素脱水葡萄糖单元的摩尔比，可以得到取代度为0.98–1.65的有机可溶性AC。通过选择四种硫醇化合物，对AC的点击反应进行了能力评估。AC-click产品通过FT-IR，NMR和元素分析进行了表征，结果表明副反应几乎没有杂质或亚结构。点击反应显示出较高的转化率，并且所有AC-click产品均显示出在某些溶剂中的高溶解度。这项工作提供了一种在水性体系中合成AC的简便方法，并显示了纤维素温和多样衍生化的新阶段。

更新日期：2015-03-17

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