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Fatty amines – a commercial overview
The document discusses the production of fatty amines, focusing on the different types of amines (primary, secondary, and tertiary) and their applications such as corrosion inhibitors and fabric softeners. It details the reaction conditions, catalyst choices, and specific temperature and pressure ranges for each type of amine production. The document outlines chemical processes involved in forming these amines, including reactions with ammonia and other compounds.
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Fatty amines – a commercial overview
- 1. Gerard B. Hawkins ManagingDirector
- 2. Most uses dependon the cationic nature of the amine Fatty Amines Corrosion Inhibitors Fabric Softeners Lubricant Additive Organoclays Sanitizing Agents H H NR
- 3.
- 4. Which amines areproduced depends on: reaction conditions ◦ NH3 pressure ◦ Temperature Catalyst choice ◦ Raney Ni ◦ Supported Ni powders
- 5. Fatty nitriles FattyacidsAl2O3 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 slurryphase 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 + NH3R-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 Firstreaction step
- 9. R-CH=NH + H2 imine Primaryamine formation R-CH2NH2
- 10. Secondary amine formation R-CH=NH+ R-CH2NH2imine R-CH-NH-CH2-R NH2 1-aminodialkylamine
- 11.
- 12. Secondary amine formation R-CH2-NH-CH2-R secondaryamine R-CH=N-CH2-R imine +H2
- 13. Secondary amine formationvia hydrogenolysis R-CH-NH-CH2-R NH2 1-aminodialkylamine R-CH2-NH-CH2-R - NH3 secondary amine +H2
- 14. Tertiary amine formation proceedsvia the same route as with the secondary amine formation. However, secondary amine condenses with imine to yield tertiary intermediates.
- 15. Amine Catalyst Saturated PrimaryAmine 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