Researches on Cellulose, 1895-1900Cross, C. F. (Charles Frederick)
Science
Researches on Cellulose, 1895-1900
Cross, C. F. (Charles Frederick)
Cellulose
We ourselves have contributed a link in this chain of evidence
connecting the furfuroids of the plant with levulose or other
keto-hexose. We have shown that the hydroxyfurfurals are constituents of
the lignocelluloses. The proportion present in the free state is small,
and it is not difficult to show that they are products of breakdown of
the lignone groups. If we assume that such groups are derived ultimately
from levulose, we have to account for the detachment of the methyl
group. This, however, is not difficult, and we need only call to mind
that the lignocelluloses are characterised by the presence of methoxy
groups and a residue which is directly and easily hydrolysed to acetic
acid. Moreover, the condensation need not be assumed to be a simple
dehydration with attendant rearrangement; it may very well be
accompanied or preceded by fixation of oxygen. Leaving out the
hypothetical discussion of minor variations, there is a marked
convergence of the evidence as to the main facts which establish the
general relationships of the furfuroid group. This group includes both
saturated and unsaturated or condensed compounds. The former are
constituents of celluloses, the latter of the lignone complex of the
lignocelluloses.
The actual production of furfural by boiling with condensing acids is a
quantitative measure of only a portion, i.e. certain members of the
group. The hydroxyfurfurals, not being volatile, are not measured in
this way. By secondary reactions they may yield some furfural, but as
they are highly reactive compounds, and most readily condensed, they are
for the most part converted into complex 'tarry' products. Hence we have
no means, as yet, of estimating those tissue constituents which yield
hydroxyfurfurals; also we have no measure of the furfurane-rings
existing performed in such a condensed complex as lignone. But, chemists
having added in the last few years a large number of facts and
well-defined probabilities, it is clear that the further investigation
of the furfuroid group will take its stand upon a much more adequate
basis than heretofore. On the view of 'furfural-yielding' being
co-extensive with 'pentose or pentosane,' not only were a number of
important facts obscured or misinterpreted, but there was a barrenness
of suggestion of genetic relationships. As the group has been widened
very much beyond these limits, it is clear that if any group term or
designation is to be retained that of 'furfuroid' is 'neutral' in
character, and equally applicable to saturated substances of such widely
divergent chemical character as pentoses, hexosones, glycuronic acid,
and perhaps, most important of all, levulose itself, all of which are
susceptible of condensation to furfural or furfurane derivatives, as
well as to those unsaturated compounds, constituents of plant tissues
which are already furfurane derivatives.
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