Path A : Production of Primary Amine from Hard Tallow

In this pathway,the fatty amines are derived from fatty acid through nitrilation and
hydrogenation. The fatty acid is extracted from Hard tallow. The hard tallow contains 52.5%
steraic acid among all the other fatty acids. The steraic acid is extracted from the hard tallow
through fat splittinng process.Sulphuric acid is added to accelerate the splitting reaction to
produce the fatty acid and glycerol.
Then, the steraic acid reacts with ammonia to become aliphatic nitrile in the form of
octadecane nitrile and water as by-product.Zinc stearate is commonly used as a catalyst for
this reaction. This reaction happens at pressure 1atm .
Finally, the octadecane nitrile undergoes hydrogenation in the presence of hydrogen and rany
nickel catalyst to produce octadecane-1-amine or stearylamine which is known as primary
amine at the third stage.
Overall Equation :
CH3(CH2)16COOCH2 + H2O
CH3(CH2)16COOH + NH3
C18H35N + 2H2

CH3(CH2)16COOCH2 + NH3 + 2H2

1st Stage Condition :

Temperature : 250-330 c
Pressure : 50-60 atm
pH : 4-5.5
Solvent : Sulphuric Acid (H2SO4)
Catalyst : Nickel-Alumina (NiO/Al2O3)
Conversion : 50 %
Yield : 95 %
By-product : Glycerol

2nd Stage Condition :

CH3(CH2)16COOH + CH2OH
C18H35N + 2H2O
C18H39N

C18H39N + CH2OH + H2O

Temperature : 300-330 c
Pressure : 1 atm
Catalyst : zinc stearate
By-product : Water

3rd Stage Condition :

Temperature : 50-170 c
Pressure : 6.8-34 atm
Catalyst : Raney Nickel Catalyst
Conversion : 100 %
Yield : Primary Amine 94 %
Secondary Amine 6 %

Undesired By-Product : Secondary Amine

Advantages :

This process can handle various concentrated range of nitriles.

Produces the least undesired by-product which is the secondary amine.
The reactions by-products are mainly water which is non-toxic.
Low production cost.
High conversion and yield of primary amine.

Disadvantages :

Raney Nickel Catalyst is expensive

Low conversion of fatty acids (50 % conversion) as it has to be recycled and undergo
hydrolysis again to obtain stearic acid.
Sulphuric Acid as a solvent is corrosive to the interior of the metal reactors.

Component

Chemical Formula

Glyceryl Tristearate
Ammonia
Hydrogen
Steaylamine
Water
Glycerol

CH3(CH2)16COOCH2
NH3
H2
C18H39N
H2O
CH2OH

Molecular Weight
(lb/lb mol)
297
17
2
269
18
31

Value (USD/lb)
0.29
0.25
0.40
1.09
0
0.10

Gross profit table for the production of primary amine from Glyceryl Tristearate
Reaction

CH3(CH2)16COOCH2 + NH3 + 2H2

Mole (lbmol)
1
1
MW
297
17
(lb/lbmol)
Mass (lb)
297
17
Ratio (lb/lb
1.10409
0.06320
SA)
*SA = Stearylamine Monomer

C18H39N + CH2OH + H2O

2
2

1
269

1
31

1
18

4
0.01487

269
1

31
0.11524

18
0.06691

Gross Profit = [ 0.1 (0.11524) + 1.09 ] [ 0.29 (1.10409) + 0.25 (0.06320) + 0.40 (0.01487)
= $ 0.7596 / lb SA