کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
7782540 1500565 2018 42 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Regioselective chlorination of cellulose esters by methanesulfonyl chloride
ترجمه فارسی عنوان
کلرینگ ریلیزلی استرهای سلولز بوسیله متانسولفونیل کلراید
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی
Regioselective chlorination of cellulose is challenging due to its low reactivity, the small reactivity differences between cellulosic hydroxyl groups, and the high and diverse reactivity of most common chlorinating agents. Halogenation of cellulose affords useful precursors for subsequent nucleophilic substitution reactions, permitting incorporation of new functionality. Herein we report a simple and efficient pathway for preparation of 6-chloro-6-deoxycellulose esters and their derivatives. Cellulose acetate (degree of substitution (DS) 1.75, CA320S) can be chlorinated by essentially quantitative reaction of the primary alcohol groups with methanesulfonyl chloride (MsCl), yielding 6-chloro-6-deoxy cellulose acetate. Characterization methods including 1H NMR, 13C NMR, FT-IR spectroscopy, and elemental analysis, demonstrated chemo- and regioselective C-6 chlorination. We also demonstrate that chlorinated cellulose acetate is a useful intermediate for displacement reactions with nucleophiles including sodium azide, amines, and thiols to prepare functional cellulose ester derivatives.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Polymers - Volume 193, 1 August 2018, Pages 108-118
نویسندگان
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