Sucrose chemistry reactivity

The purpose of this chapter is to provide an update on our understanding of the reactivity of sucrose and the selectivity of its transformations into functionalized derivatives that have become industrial realities because of their biodegradability or biocompatibility. It follows historical accounts on the topic books on sucrose and its chemistry,1 4 a series of books dealing with the use of carbohydrates (in general) as organic raw materials,5 8 and also chapters and review articles.9 24... 

Sucrochemistry is already more than 50 years old, and has become a field of carbohydrate chemistry on its own. Indeed, considerable progress has been achieved in the monitoring of the chemical reactivity of sucrose, with the efforts of many research teams who have built on the steps of a few pioneers. Many sucrose derivatives can now be prepared, and sophisticated synthons as well as simple substituted compounds have been reported. However, only a few examples have yet reached the level of the industrial development, and these are mainly in the field of food and cosmetic additives and surfactants. Various polymers, additives for materials, and some chemical intermediates have also been produced. Bioconversions are certainly a major avenue for using sucrose as a starting material, and ethanol production will increase as a consequence of high oil prices. Current awareness of the shortage of fossil resources emphasizes the potential for chemical transformations of sucrose in providing new uses of this abundant natural resource. 

Basic chemical research, best done in academic institutions or by contract research organizations, was needed first in order to obtain sucrochemicals of the nature envisioned by Dr. Hass. Thus, early work in sucrochemistry was funded by the Sugar Research Foundation in such research laboratories. An exploratory project oriented towards discovering the fundamental chemistry of sucrose and other carbohydrates had been supported previously at the Massachusetts Institute of Technology from 1943 to 1950. The main purpose of the project, however, was to train carbohydrate chemists and to apply classical carbohydrate chemistry more broadly to sucrose and its close relatives. None of the derivatives produced and studied were found to be of practical importance in later sucrochemical studies, although a number of patent applications were filed and patents issued. Some of these studies were continued in several other laboratories during the early 1950 s, and a number of additional studies were undertaken to elucidate the relative reactivities of the various reactive entities, determine reaction kinetics and to try to make new and possibly useful derivatives. An intensive search was undertaken to find mutual solvents for both hydrophilic sucrose and hydrophobic reactants. 

Beyond the use of ethyl alcohol as a beverage, solvent or transportation fuel, the alcoholic fermentation of sucrose opens a pathway to an alternative C2 chemistry starting from ethanol as a reactive chemical intermediate and building block" and applying technologies that are well-established unit operations in the chemical industry. 

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