The Reactivity of Some Epoxides toward Cellulose

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Abstract
The reactivity of 25 mono- and diepoxides towards cellulose under hot, anhydrous, acidic conditions has been investigated using a small scale procedure which permits the study of reagents available only in small amounts. The epoxides were emulsified in aqueous solutions of zinc perchlorate catalyst and applied to cellulose in the form of a small piece of cotton fabric. The impregnated sample was then heated at an elevated temperature. The extent of reaction was followed by changes in the density of the cellulose fibers, in their solubility in cuprammonium hydroxide, and in the crease re covery of the fabric. The latter two criteria were important only with difunctional reagents. The compounds tested were principally aliphatic and alicyclic epoxides in the mole cular weight range of 70 to 300. The results suggest that to be able to react with cel lulose under these conditions, the epoxide must be non-volatile, water-soluble to some degree, and free from steric hindrance of certain sorts.