Experiment No.

01

Objective:

To prepare phenol formaldehyde resin (Bakelite).

Apparatus:

i. Glass rod
ii. Beakers
iii. Funnel
iv. Measuring cylinder
v. Dropper
vi. Filter paper

Chemicals used:

i. Glacial acetic acid
ii. 40% formaldehyde solution
iii. Phenol
iv. Conc. HCl

Principle:

Phenol formaldehyde resins are condensation polymers and are obtained by condensing phenol
with formaldehyde in the presence of an acidic or alkaline catalyst.

Theory:

Resins - In polymer chemistry and materials science, resin is a "solid or highly viscous
substance," which is typically convertible into polymer. These are often mixture of organic
compounds.
Resins are may be of natural or synthetic origin. Naturally resins are obtained from plants (i.e.
glue etc.) while synthetic ones are prepared artificially by the polymerization reactions (e.g.
Bakelite).

Phenol - formaldehyde polymer - also called Bakelite or chemically “polyoxybenzyl methylene
glycol anhydride” and is the oldest synthetic polymer. It is the first synthetic plastic that was
formulated in the 'Age of Plastics'. Leo Baekeland is the chemist who developed it in the year
1907, in New York.

It is thermosetting plastic (a thermosetting plastic is a plastic that liquefies and is malleable
when heated. Then it becomes permanently hard and rigid when cooled. Thus, it can be used to
make a variety of items).

It is obtained by the condensation reaction of phenol with formaldehyde in the presence of
either an acid or a base catalyst. In the presence of acid catalyst, the reaction starts with the initial
formation of o-and/or p- hydroxy methyl phenol derivatives, which further react with phenol to
form compounds having rings joined to each other through –CH2 groups. The initial product
could be a linear product (NOVALAC – used in paints).

The chemical reactions are:

H+
Novalac on heating with formaldehyde undergoes cross linking to form infusible solid mass
called Bakelite.

H2C

Here, during the reaction, acidic medium is given by adding conc. HCl which catalyzes the
reaction. However, glacial acetic acid was added which acts as a solvent.

Glacial acetic acid - Anhydrous (water-free) acetic acid is sometimes called glacial acetic acid
because it solidifies just below room temperature, at 16.7°C. Acetic anhydride is an acetylation
agent. Glacial acetic acid is an excellent polar protic solvent. Acetic acid is often used as a
solvent for reactions involving carbocation, such as Friedel Crafts alkylation.
Mechanism of reaction:
Properties of Bakelite:

Chemical formula (C6H6O.CH2O)n

Molar mass Variable

Appearance Brown solid

Density 1.3 g/cm3

Thermal conductivity 0.2 W/(m.K)

Specific heat capacity 0.92 kJ/(kg.K)

Bakelite has a number of important properties. It can be molded very quickly. Moldings are
smooth, retain their shape and are resistant to heat, scratches, and destructive solvents. It is also
resistant to electricity, and prized for its low conductivity. It is not flexible. It is nonflammable.
The dielectric constant of Bakelite ranges from 4.4 to 5.4.

Phenolic resin products may swell slightly under conditions of extreme humidity or perpetual
dampness. When rubbed or burnt, Bakelite has a distinctive, acrid, sickly-sweet or fishy odor.

Applications:

i. Bakelite was used for its electrical non-conductivity and heat-resistant properties in
electrical insulators, radio and telephone casings, and such diverse products as
kitchenware, jewelry, pipe stems, children's toys, and firearms.
ii. Bakelite's availability and ease and speed of molding helped to lower the costs of
production and increase product availability so that both telephones and radios became
common household consumer goods.
iii. Due to high molding character, heat and electrical resistivity it was also very important to
the developing automobile industry.
iv. It was being used to make billiard balls.
v. Bakelite was sometimes used as a substitute for metal in the magazine, pistol grip, fore
grip, hand guard, and butt stock of firearms.
vi. The pure Bakelite resin was lovely amber, and it could take other colors as well.

Procedure:

i. Take a 500 ml beaker and add 50 ml of glacial acetic acid in it.
ii. Add 25 ml of 40% formaldehyde solution which contain 20 grams of phenol in it.
iii. Add 12 ml of conc. HCl in it.
iv. Gently heat the mixture; within 5 minutes a large mass of pinkish/brown color plastic is
formed.
v. The residue obtained is washed with distilled water and filtered product is then dried.

Precautions:

i. The reaction is exothermic and is sometimes vigorous and it is better to be a few feet
away from the beaker while adding the HCl and until the reaction is complete.
ii. Most phenols are harmful if inhaled, ingested or absorbed through skin. They cause
severe irritation or damage to skin and eyes. Some phenols are suspected carcinogen,
should
not inhale its dust or vapor, wear gloves and avoid contact.
iii. HCl is poisonous and corrosive. Contact or inhalation can cause severe damage to the
eyes, skin and respiratory tract. So wear gloves while handling and do not breathe vapors.

Observations & calculations:

Weight of filter paper = 2.54 g

Weight of filter paper + residue/cake = 116.56 g

Weight of residue/cake = 116.56 – 2.54
= 114.02 g

Results:

The phenol formaldehyde resin (Bakelite) was prepared in the laboratory.