Novel method of synthesizing 5,6-celluloseen and the preparation of new cellulose derivatives by reaction with its double bonds

Abstract

Listen

Translate article

A LARGE number of methods of modifying cellulose have recently been developed, but there is not one which would enable certain functional groups to be introduced directly into the pyran ring of the cellulose maeromolecule. However it is quite probable that the introduction of the same 'functional groups into the side chain (synthesis of graft copolymers of cellulose) or directly into the ring may variously affect the properties of the resulting cellulose derivative. At the present stage the introduction of new functional groups into the pyran ring and the preparation of new types of cellulose derivatives, in this way, e.g. derivatives with four acetyl groups in the pyran ring can be effected only by using modified cellulose compounds containing a double bond in the pyran ring, i.e. the so-called celluloseen compounds. This product (celluloseen) was used by us as the starting material for the synthesis of new types of cellulose derivatives. There is information in the literature [1-3] describing a method of synthesizing unsaturated cellulose derivatives containing a double bond between 5 and 6 carbon atoms of the elementary unit (5,6-celluloseen); this involves the treatment of cellulose iodotosylate with absolute piperidine to obtain 5,6-celluloseen compounds containing a considerable number of chemically bound piperidine radicals. There is information in the literature regarding certain reactions for converting the double bond in the 5,6-celluloseen molecule: hydration [1-2], and the addition of CHCla, CC14, PC13, HSiG13 [3] and CHaCOOH [4]. More widespread use of celluloseen for various chemical conversions could be made provided that there was a new and more convenient method of synthesizing this product which does not contain chemically bound nitrogen containing groups. The initial products used for the synthesis of 5,6-celluloseen were cellulose iodotosylate obtained by tosylating cotton fluff [5] with subsequent iodization in the usual manner [1], and also cellulose iodonitrate obtained by iodizing