A Schotten-Baumann Condition for Protecting Water-Soluble Polysaccharides

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  • MATSUI Eiki
    Department of Chemistry and Biology, Fukui National College of Technology
  • YOSHIDA Ryuji
    Department of Chemistry and Biology, Fukui National College of Technology
  • UCHIDA Nobuyuki
    Department of Chemistry and Biology, Fukui National College of Technology

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Other Title
  • ショッテンバウマン反応による水溶性天然高分子変換法の開発
  • ショッテンバウマン ハンノウ ニ ヨル スイヨウセイ テンネン コウブンシ ヘンカンホウ ノ カイハツ

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Abstract

The use of biphasic aqueous basic conditions is often named Schotten-Baumann condition. As an example, the acylation of alcohols with carboxylic acid chlorides in aqueous base leads to the production of corresponding esters and salts. We apply the Schotten-Baumann condition to the hydroxy acylation reaction of water-soluble polysaccharides. The polysaccharides were easily converted to benzoyl compounds by reacting with hydroxyl groups and benzoyl chloride in saturated Na2CO3 aqueous solution. The benzoyl polysaccharide compounds were characterized by ATR-FT/IR and 13C NMR spectroscopy. The ATR-FT/IR and 13C NMR showed characteristic peaks for polysaccharides and benzoyl groups. These reactions can be achieved under waterborne conditions with simple handling and without using poisonous organic solvents.

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 72 (2), 71-75, 2015

    The Society of Polymer Science, Japan

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