Fatty Amines - Uses Fatty Amines - Types Selectivity Reaction conditions NH3 pressure Temperature Catalyst choice Raney Ni Supported Ni powders Fatty amines production

1. Gerard B. Hawkins
Managing Director

2. Most uses depend on the cationic nature of the amine
Fatty
Amines
Corrosion
Inhibitors
Fabric
Softeners
Lubricant
Additive
Organoclays
Sanitizing
Agents
H
H
NR

3. Primary amine
Secondary amine
Tertiary amine

4. Which amines are produced depends on:
 reaction conditions
◦ NH3 pressure
◦ Temperature
 Catalyst choice
◦ Raney Ni
◦ Supported Ni powders

5. Fatty nitriles Fatty acidsAl2O3
NH3
Unsaturated
primary amine
Saturated
primary amine
Saturated and
unsaturated
secondary
amines
Dialkyl
monomethyl
tertiary amine
Ni(P)
Sponge
Ni(D)
Ni(D) Formaldehyde

6.  Batch slurry phase most common
 Fixed bed or continuous slurry phase also used
Product Temp (C)
Pressure
(bar)
Catalysts Special Conditions
Primary 80-150 10-550
nickel, raney
nickel, cobalt
Ammonia added to feed to suppress
secondary and tertiary amine formation
Secondary 150-200 50-200 nickel, cobalt Ammonia removed by purging with hydrogen
Tertiary 160-230 7 - 14 nickel, cobalt
Secondary Amine used as feed; hydrogen
purge necessary to remove ammonia
Unsaturated
copper
chromite,
nickel
powder
similar to abovesimilar to above

7. R-COOH + NH3 R-COONH4
R-COONH4 R-CONH2 + H2O
ammonium salt
amide
R-CONH2 R-CN + H2O
nitrile
R-CN + 2H2 FATTY AMINES

8. R-C≡N + H2
R-CH=NH
imine
First reaction step

9. R-CH=NH + H2
imine
Primary amine formation
R-CH2NH2

10. Secondary amine formation
R-CH=NH + R-CH2NH2imine
R-CH-NH-CH2-R
NH2
1-aminodialkylamine

11. Secondary amine formation
R-CH-NH-CH2-R
NH2
1-aminodialkylamine
R-CH=N-CH2-R
- NH3
imine

12. Secondary amine formation
R-CH2-NH-CH2-R
secondary amine
R-CH=N-CH2-R
imine
+H2

13. Secondary amine formation via hydrogenolysis
R-CH-NH-CH2-R
NH2
1-aminodialkylamine
R-CH2-NH-CH2-R
- NH3
secondary amine
+H2

14. Tertiary amine formation
proceeds via the same route as
with the secondary amine
formation. However, secondary
amine condenses with imine to
yield tertiary intermediates.

15. Amine Catalyst
Saturated Primary Amine Sponge Ni type catalyst
Unsaturated Primary Amine Supported Ni powder catalysts, Supported Co tablet catalysts
Saturated Secondary Amines Supported Ni powder catalysts
Unsaturated Secondary Amines Supported Ni powder catalysts
Tertiary Amines Supported Ni powder catalysts