fatty amines – a commercial overview
DESCRIPTION
Fatty Amines - Uses Fatty Amines - Types Selectivity Reaction conditions NH3 pressure Temperature Catalyst choice Raney Ni Supported Ni powders Fatty amines productionTRANSCRIPT
Gerard B. Hawkins Managing Director
Most uses depend on the cationic nature of the amine
Fatty Amines
Corrosion Inhibitors
Fabric Softeners
Lubricant Additive
Organoclays
Sanitizing Agents
H
H N R
Primary amine
Secondary amine
Tertiary amine
Which amines are produced depends on: reaction conditions ◦ NH3 pressure ◦ Temperature
Catalyst choice ◦ Raney Ni ◦ Supported Ni powders
Fatty nitriles Fatty acids Al2O3 NH3
Unsaturated primary amine
Saturated primary amine
Saturated and unsaturated secondary
amines
Dialkyl monomethyl
tertiary amine
Ni(P)
Sponge
Ni(D)
Ni(D) Formaldehyde
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
R-COOH + NH3 R-COONH4
R-COONH4 R-CONH2 + H2O
ammonium salt
amide
R-CONH2 R-CN + H2O nitrile
R-CN + 2H2 FATTY AMINES
R-C≡N + H2
R-CH=NH imine
First reaction step
R-CH=NH + H2 imine
Primary amine formation
R-CH2NH2
Secondary amine formation
R-CH=NH + R-CH2NH2 imine
R-CH-NH-CH2-R
NH2 1-aminodialkylamine
Secondary amine formation
R-CH-NH-CH2-R
NH2 1-aminodialkylamine
R-CH=N-CH2-R
- NH3
imine
Secondary amine formation
R-CH2-NH-CH2-R secondary amine
R-CH=N-CH2-R imine
+H2
Secondary amine formation via hydrogenolysis
R-CH-NH-CH2-R
NH2 1-aminodialkylamine
R-CH2-NH-CH2-R
- NH3
secondary amine
+H2
Tertiary amine formation proceeds via the same route as with the secondary amine formation. However, secondary amine condenses with imine to yield tertiary intermediates.
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
