Cellulose
Cellulose is an organic compound with the formula (C6H10O5)n
, a polysaccharide consisting of a linear chain of several hundred to many
thousands of β(1→4) linked D-glucose units. Cellulose is an important
structural component of the primary cell wall of green plants, many forms of
algae and the oomycetes. Some species of bacteria secrete it to form
biofilms. Cellulose is the most abundant organic polymer on Earth. The
cellulose content of cotton fiber is 90%, that of wood is 40–50% and that of
dried hemp is approximately 57%.
Cellulose is tasteless, odorless, hydrophilic insoluble in water and most
organic solvents, is chiral and is biodegradable. It m.p is 467 °C .I t can be
broken down chemically into its glucose units by treating it with
concentrated mineral acids at high temperature.
Structure
1. Its molecular formula may be represented by (C6H10O5)n
2. On acidic hydrolysis cellulose gives quantitative yield of crystalline D-
glucose which indicates that cellulose is made up of only glucose.
3. Cellulose on acetylation / nitration / methylation gives trisubstituted
derivatives which suggest that only three hydroxyl groups are free per
glucose unit.
4. Cellulose on methylation followed by hydrolysis gives 2,3,6-
trimethylglucose (86%) and 2,.3,4,6-tetramethylglucose (nearly 0.6%)
without any dimethylglucose. This set of reactions give following
indications:
a. Formation of 2,3,6-trimethylglucose indicate that in cellulose,
hydroxyl groups at position 2,3,6 are free. Therefore in cellulose
the two glucose units are linked through C-1 and C-5 (if glucose
units are present as furanose). But cellulose is not easily
hydrolysed hence glucose units must be in the form of
pyranose ring [Link] glucose units are linked via C-1 and C-
[Link] part structure of cellulose may be as follows:
b. Low yield (0.6%) of 2,3,4,6-tetramethylglucose indicated that
cellulose has a chain length of about 100-200 glucose units.
c. The failure to isolate any dimethyl D-glucose indicates that
cellulose is linear polymer.
5. Cellulose on acetolysis, i.e. simultaneous acetylation and hydrolysis
(this is carried out with a mixture of acetic anhydride and
concentrated sulphuric acid) forms cellobiose octaacetate. This
indicates that cellobiose unit is present in cellulose. In cellobiose
glucose unit are present in pyranose form i.e. C-5 is involved in ring
formation and hence glucose units are linked C-1 to C-4. Isolation of
cellobiose indicates that pairs of glucose units are joined by β-links.
The formation of cellobiose derivative does not indicate that links
between the glucose units are the same (all β) or alternate (,β).
6. Cellulose forms colloidal solution, property of high polymer, in the
solvents in which glucose is soluble which indicate that cellulose is
very large molecule.
7. Cellulose forms fibre, e.g. rayon which supports that cellulose
molecule is linear. The long length and linear structure of cellulose is
confirmed by X-ray analysis.
8. Thus on the basis of above structure of cellulose may be as follows:
