Experiment 25:

ORGANIC POLYMERS:
THE SYNTHESIS OF NYLON

Objectives:

To synthesize Nylon 6,10 from

hexamethylene diamine and sebacoyl
chloride.
To determine the length of the Nylon
formed using a simple mathematical
calculation.

SYNTHESIS OF AN AMIDE
O

H
R

N
H

amine

catalyst

H2O

HO

Carboxylic
Acid

amide

Reacting a carboxylic acid with an amine

yields an amide. Water is a by-product,
and this reaction is slow without a
catalyst.

SYNTHESIS OF AN AMIDE
O

H
R

N
H

amine

HCl

Cl

Acid chloride

amide

By using a carboxylic acid chloride, a

more reactive carboxylic acid derivative,
the rate of reaction can be increased. In
this reaction, HCl is the by-product.

MECHANISM
O
R

H
+
Cl

R'

O
H

R
R'

C
N
H

+ OH
Cl
H

R
R'

C
N

Cl
H

O
R

N
R'

SYNTHESIS OF NYLON 6,10

H

H
N
H

CH2CH2CH2CH2CH2CH2 N

Hexamethylene
diamine

O
C

Cl

CH2CH2CH2CH2CH2CH2CH2CH2 C

Sebacoyl
chloride

Cl

In order to make a polyamide, such as Nylon 6,10,

the amine molecule must have a NH2 group at each
end, and the acid chloride must have a COCl group
at each end.

The diamine and the diacid chloride bond together,

end-on-end, to form very long chains.

Nylon 6,10 is made from hexamethylene diamine

(the diamine) and sebacoyl chloride (the diacid
chloride).

SYNTHESIS OF NYLON 6,10

O

H
N

CH2CH2CH2CH2CH2CH2 N

O
CH2CH2CH2CH2CH2CH2CH2CH2 C

Cl

Cl

Hexamethylene
diamine

Sebacoyl
chloride

O
H
N

CH2CH2CH2CH2CH2CH2

H
N

Nylon 6,10 =

O
CH2CH2CH2CH2CH2CH2CH2CH2

H
N

H
(CH2)6 N

H
N

CH2CH2CH2CH2CH2CH2

(CH2)8 C

H
N

HCl

CLASSIFICATIONS OF
SYNTHETIC POLYMERS

Synthetic polymers are classified by their

method of synthesis.
Synthetic Method

Chain-growth

Step-growth

polystyrene

Polyamides (nylon)

NATURAL ORGANIC POLYMERS

Proteins

hair, skin, tissue

Polysaccharides

cellulose, starch

Polynucleotides

DNA, RNA

SYNTHETIC ORGANIC POLYMERS

Nylons
Polyesters
Acrylics
Polyvinyls
Plastic sheeting and plumbing
materials
Polystyrenes
Insulating materials

EXPERIMENTAL PROCEDURE
(Synthesis)

Pour diamine solution and diacid

chloride in separate beakers.
Using forceps, grasp the film that
forms at the interface of the two
liquids.
Pull up slowly and wrap end of nylon
string around a test tube.
Rotate the tube and count the
number of revolutions made before
no more nylon can be produced.

EXPERIMENTAL PROCEDURE
(Analysis)

Calculate the length of the nylon string

produced (in meters) using the following
equation:

Nylon produced (m) =

(test tube diameter (m)) X () X (# test tube revolutions )

Table 25.1
Test tube diameter (mm)

# of test tube revolutions

Length of nylon (m)

SAFETY CONCERNS

CAUTION:
All chemicals are hazardous to
the skin and eyes. Safety
goggles and gloves are required
during the experiment!!!

WASTE MANAGEMENT

Pour all waste from synthesis and

solubility tests into container labeled
ORGANIC WASTE (Polymers)

CLEANING

Clean all glassware with soap, water,

brush, and rinse with wash acetone
before returning to lab drawer!
DO NOT return any glassware to lab
drawer dirty or wet!