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

H O H O

R N + C R catalyst H2O
R N C R +

H HO

Carboxylic
amine amide
Acid

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
H O H O

R N + C R R N C R + HCl

H Cl

amine 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 O
H O
+ + OH C
C N C
R Cl R Cl
R' H R Cl N
N R' H
R' H
H

C H
R N

R'
 SYNTHESIS OF NYLON 6,10
H H O O

N CH2CH2CH2CH2CH2CH2 N C CH2CH2CH2CH2CH2CH2CH2CH2 C

Sebacoyl
H H Cl Cl
Hexamethylene
diamine chloride

 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

H O O
H

N CH2CH2CH2CH2CH2CH2 N + C CH2CH2CH2CH2CH2CH2CH2CH2 C

H H Cl Cl

Hexamethylene Sebacoyl
diamine chloride

O O

H H H H
N CH2CH2CH2CH2CH2CH2 N C CH2CH2CH2CH2CH2CH2CH2CH2 C N CH2CH2CH2CH2CH2CH2 N + HCl

O O

H H
Nylon 6,10 = N (CH2)6 N C (CH2)8 C
n n
 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 (p) 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!