EXPERIMENT 3
Object: Synthesis and characterization of Hexamine.
References: Rao GD, “ Practical medicinal chemistry” first edition-2007-08, Birla
publication pvt. Ltd Delhi, Page No. 34
Chemicals/ Reagents
Chemicals/ Reagents Qty. Prescribed for Qty. Prescribed Qty. Taken
method 1 for method 2
Formaldehyde 38% 473 g 6 ml
Ammonium Hydroxide 700 g
20 %
Ammonia As required 4 ml
Ethyl Alcohol As required
Glasswares/Apparatus: Weighing Balance, Round Bottom flask, glass rod, pipette,
measuring cylinder, funnel, beaker, Melting Point Apparatus, TLC Plate etc
Principle: Hexamethylenetetramine or methenamine is a heterocyclic organic
compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in
water and polar organic solvents. It has a cage-like structure similar to adamantane. It is
useful in the synthesis of other chemical compounds, e.g., plastics, pharmaceuticals, rubber
additives. It sublimes in vacuum at 280 °C. It is prepared industrially by
combining formaldehyde and ammonia.[4] The reaction can be conducted in gas phase and in
solution.
Reaction:
Procedure:
1. 473 g of 38% formaldehyde solution is treated with 700 g of 20 % ammonium
hydroxide solution, until the solution is slightly alkaline.
2. The mixture is allowed to stand for several hours and if necessary more ammonia
being added.
3. The solution is filtered and then evaporated in vacuum to a thick paste.
4. The hexamine crystals are filtered off, washed with ethyl alcohol and dried.
5. To obtained pure crystals of hexamine it is recrystallized from water or alcohol
6. Hexamine forms colorless, odorless crystals, which are soluble in water and 90%
alcohol.
7. It does not melt on heating, but sublime at a temperature of about 260 0c.
Characterization of compound
S.No. Characterization parameter Observation
1. State
2. Colour
3. Solubility
4. Melting Point
5. Practical yield 100 gm
6. Theoretical yield 140 gm
7. % yield
Calculations
Calculate the % yield of the compound as follows:
% yield = Practical Yield/theoretical yield *100
Result: Hexamine was synthesized with a % yield of …………….and Melting point of ……