Schotten‐baumann esterification of poly(vinyl alcohol). I.

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Abstract
The esterification of poly(vinyl alcohol) by SCHOTTEN‐BAUMANN reaction gave poly(vinyl cinnamate). The proposed method is that cinnamoyl chloride dissolved in the mixture of toluene and methyl ethyl ketone is added to the aqueous mixture of poly(vinyl alcohol) and sodium or potassium hydroxide at low temperatures. Produced poly(vinyl cinnamate) is dissolved in the organic layer. This reaction differs from other SCHOTTEN‐BAUMANN reactions such as the interfacial polycondensation and the production of phenyl benzoate in the point that weak alkalis, for example sodium or potassium carbonate and bicarbonate, etc., have no effects. This fact suggests that the ionization of the hydroxyl groups of poly(vinyl alcohol) plays an important role in the esterification. The addition of surface active agents lowers the yield of the product. The explanation is that the esterification of hemi‐esterified poly(vinyl alcohol) at the late period of the reaction proceeds in the organic solvent layer and the detergents aid only the hydrolysis of chloride.

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