Carbohydrate

Carbohydrates

Structurally, carbohydrates are polyfunctional compounds. They contain two types of functional
groups, the hydroxyl group, and the carbonyl group. They are polyhydroxy aldehydes or
polyhydroxy ketones or compounds which are converted to these on hydrolysis. carbohydrates
have the empirical formula (CH2O)n. the formation of carbohydrates in nature occurs in green
plants by a process called photosynthesis. Plants contain the green pigment chlorophyll, which
catalysis the conversion of CO2 and H2O into sugar.

CO2 + H OH + Solar Energy C6(H2O)6 + 6O2

Classification of Carbohydrates

There are three major classes of carbohydrates:

1. Monosaccharides

Monosaccharides, or simple sugars, consist of a single polyhydroxy aldehyde or ketone unit.

These polyhydroxy aldehydes or ketones cannot be decomposed by hydrolysis to give simpler
carbohydrates. Example: glucose and fructose, both having similar molecular formula C6H12O6.
+
H
C6H12O6 + 6H2O No reaction

2. Oligosaccharides

Oligosaccharides are carbohydrates, which yield a definite number (2-9) of monosaccharide

molecules on hydrolysis. They include

a. Disaccharides, which yields two monosaccharide molecules upon hydrolysis. Example:

sucrose, maltose (C12H22O11)
+
H
C12H22O11 + H2O C6H12O6 + C6H12O6

Sucrose Glucose Fructose

+
H
C12H22O11 + H2O 2 C6H12O6

Maltose Glucose

b. Trisaccharides, which yield three monosaccharide molecules upon hydrolysis. Example:

raffinose (C18H32O16)
 +
H
C18H32O16 + 2 H2O C6H12O6 + C6H12O6 + C6H12O6

Raffinose Glucose Fructose Galactose

c. Tetrasaccharides etc.

3. Polysaccharides

The polysaccharides are sugar polymers containing more than 20 or so monosaccharide units,
and some have hundreds or thousands of units. Example: starch and cellulose (C6H12O6)n.
+
H
(C6H10O5)n + n H2O C6H12O6

Starch or Glucose
Cellulose

In general, the monosaccharides and oligosaccharides are crystalline solids, soluble in water, and
sweet in taste. They are collectively known as sugars. Polysaccharides, on the other hand, are
amorphous, insoluble in water, and tasteless. They are called non-sugars.

The carbohydrates may also be classified as either

1. reducing sugar
2. non-reducing sugars.

All those carbohydrates which have the ability to reduce Fehling’s solution and Tollen’s
reagent are referred to as reducing sugars, while others are non-reducing sugars. All
monosaccharides and disaccharides other than sucrose are reducing sugar.

MONOSACCHARIDES
The monosaccharides are the basis of carbohydrate chemistry since all carbohydrates are either
monosaccharides or are converted into monosaccharides on hydrolysis. The monosaccharides
are polyhydroxy aldehydes or polyhydroxy ketones. There are, therefore, two main classes of
monosaccharides

1. The Aldoses, which contain an aldehyde group ( )

2. The Ketoses, which contain a ketone group ( )

The aldoses and ketones may be represented by the following general formula
 D-Glucose
Occurrence: Glucose occurs naturally both in combined and free state. In the free state, it
is present in most sweet fruits and in honey. Ripe grapes often contain as much as 20 to
30% of glucose, and for this reason, it is sometimes called Grape Sugar. Small quantities
of glucose are also present in human blood and urine, but the urine of sufferers of
diabetes may contain as much as 8 to 10% of glucose. In the combined state, it forms a
major component of many disaccharides and polysaccharides.

Preparation:

1. From Sucrose (Cane Sugar): Glucose can be prepared in the laboratory by boiling
sucrose (cane sugar) with dilute hydrochloric acid or sulphuric acid for about two
hours. This hydrolyses sucrose to glucose and fructose. In order to separate
 glucose from fructose, alcohol is added during cooling. Glucose is almost insoluble
in alcohol. it crystallizes out first, while fructose is more soluble. It remains in the
solution. The solution is filtered to obtain the crystals of glucose.

C12H22O11 + H2O C6H12O6 + C6H12O6

2. From Starch: Commercially, glucose is obtained by the hydrolysis of starch by

heating with very dilute H2SO4 (0.5%) at 120°C under a pressure of 2 to 3
atmospheres.

(C6H12O6) + nH2O nC6H12O6

Limitation of Fischer projection of D-glucose

1. Glucose does not show carbonyl (-CO-) absorption peaks in FTIR analysis
2. Glucose does not give Schiff’s test for aldehydes
3. Glucose does not react with 2,4 dinitro phenyl hydrazine (2,4 DNP)
4. Glucose does not react with Tollens and Fehling reagents.
5. Glucose does not form an addition product with sodium bisulphite
6. Glucose does not react with hydroxylamine
7. Glucose does not react with Grignard reagent

All of these observations suggest the absence of a free aldehyde group in D-glucose.
 Sucrose
Sources of sugar
Sugar cane, sugar beet and fruits
Sugar cane composition
Water = 70%
Fibrous materials = 10-16%
Sucrose = 10-16%
Gummy materials = 0.5-2%
Manufacturing process steps
The conventional method for the production of sugar from sugar cane consists of the
following steps:
1. Extraction of the juice (crushing or milling);
2. Purification of juice (clarification);
3. Concentration and crystallization; and
4. Separation and drying of the crystals.
Manufacturing process
1. Extraction of the juice: In the conventional method, the cane prepared in the
manner described below is passed through a series of three-roller mills,
numbering from four to seven units.

2. Purification of juice (clarification): The mixed juice or raw juice contains 15-20
percent of sucrose and much impurity. The impurity commonly includes organic
acids (oxalic acid, citric acid, amino acids), mineral phosphates, proteins, and
colloidal coloring matter. The raw juice is slightly acidic and are purified or
clarified by the following operations
a. Defecation: The raw juice is transferred into tanks where it is heated by
steam and treated with 2-3% lime (CaO). The operation called defecation
removes the organic acids and phosphates as insoluble calcium salts. The
 proteins and colloidal coloring matter are also thrown out of the solution as
thick scum appears on the surface. The precipitated calcium salts and the
scum are removed by filtration.
b. Carbonation: The juice after the defecation process contains an excess of
lime and soluble calcium sucrosate. Carbon dioxide is then passed through
it. The process is known as carbonation removes the excess of lime and
decomposes calcium sucrosate to give back sugar and calcium carbonate.
Calcium carbonate is removed by simple filtration.

C11H21O11CaOH + CO2 C11H21O11 + CaCO3

c. Sulphitation: The juice after carbonation is treated with sulphur dioxide.

This operation is known as sulphitation completes the neutralization of the
lime and the decomposite calcium sucrosate. In addition, the color of the
juice is bleached. The clarified juice is then filtered to remove precipitate
calcium sulphite.

3. Concentration and crystallization of the juice: The clarified juice is then

concentrated by boiling under reduced pressure in multiple-effect evaporators. In
these, the steam produced in the first evaporator is used to boil the juice in the
second evaporator at lower pressure. The steam produced in the second is used to
boil the juice in the third maintained at a lower pressure and so on.
The concentrated juice is finally passed to the vacuum pans where further
evaporation reduces the water content from 6-8%. Here, partial separation of sugar
crystals takes place. The contents of the pan, known as massecuite are discharged
into a take where crystals grow in size and from a thick crop.

4. Separation and drying of crystals: The massecuite are then charged into
centrifugal machines by means of which sugar crystals are separated from the
mother liquor. The crystals are here sprinkled with a little water to wash away any
impurities sticking to their surface. The crystals are finally dried by dropping
through a removal cylinder where they meet a current flow of hot air. The sugar
thus obtained is about 96% pure.
Figure: Process flow diagram of Sucrose production from sugar cane.