Chemical Properties
Diallylamine is a clear colourless to yellow flammable liquid. Diallylamine can be detected, but it is not unpleasant at 2-9 ppm and is not intolerable at 70 ppm.
Uses
Diallylamine is manufactured from allyl chloride and ammonia. It is used as a solvent and in organic syntheses. Diallylamine is used to produce N,N-diallyl-2,2- dichloroacetamide, which is used as a safener (a safener prevents objectionable changes in mixtures of two or more substances that would otherwise be incompatible) in the preemergence herbicide EPTC (S-ethyl di-N,N-propylthiocarbamate; EPTAM(R)) (Sine, 1991; SRI Int., 1997).
Application
Diallylamine can be used:
(1) as a copper hole filling additive in printed circuit board (PCB) stacking technology. The adsorption behaviour of Diallylamine levelers agent was probed by adding it to copper sulphate electroplating solution. And the relationship between alkalinity and electrodeposition was investigated by changing the length and functional groups of the side chains.
(2) A weak base poly(diallylamine) resin was prepared for gold extraction. The resin showed high adsorption capacity (up to 5 mmol/g dry resin) and good gold selectivity for most pH ranges and many different types of solutions, including contaminated wastewater. However, the slow dissolution of the uncrosslinked polymer chains in the resin matrix limits the gold adsorption properties at low gold concentrations (less than 5 mg/dm3).
Preparation
Diallylamine is synthesized by hydrolysis of diallyl cyanamide. The hydrolysis reaction was carried out in a sulfuric acid medium, and the reflux was moderated for 6h. Yield 80-88%.
Diallylamine has been prepared by treating allylamine with allyl bromide or allyl chloride or by refluxing diallylcyanamide with diluted sulfuric acid.
A mixture of monoallylamine, diallylamine, and triallylamine is produced commercially by a reaction of allyl alcohol and ammonia with palladium acetylacetonate at 110°C for 4 hours, using 1,2-bis(diphenylphosphono)propane as the catalyst and propylene glycol as the solvent. Reaction of allyl alcohol with acetylacetone at 85°C for 3 hours gives 70% monoallylamine and 26% diallylamine (Schweizer et al., 1978).
General Description
A liquid with a disagreeable odor. Less dense than water. Flash point 70°F. May be toxic by inhalation and skin absorption. Irritates skin and eyes. Used to make other chemicals.
Air & Water Reactions
Highly flammable. Soluble in water.
Reactivity Profile
Diallylamine(124-02-7) neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Health Hazard
May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard
Diallylamine is a flammable liquid and a dangerous fire hazard when exposed to heat or flame. Vapors may travel to a source of ignition and flash back, while containers may explode in the heat of a fire. The compound may present a vapor explosion hazard indoors, outdoors, or in sewers. When heated to decomposition, diallylamine emits toxic fumes of NOx (Lewis, 1992).
Toxicology
Diallylamine can cause myocardial degeneration as well as damage to the kidneys and liver. This has been observed in rats and rabbits. Allylamines cause a severe primary fibrosis of the myocardium, The oral application of allylamine in the drinking water over 81–104 days caused a dose-dependent myocardial degeneration in rats.
Synthesis
Diallylamine is synthesized by refluxing diallylcyanamide with diluted sulfuric acid. It has also been synthesized by treating allylamine with allyl bromide or allyl chloride.
Purification Methods
Keep the amine over KOH pellets overnight, decant and distil it from a few pellets of KOH at atmospheric pressure (b 108-111o), then fractionate through a Vigreux column (p 11). [Vliet J Am Chem Soc 46 1307 1924, Org Synth Coll Vol 1 201 1941.] The hydrochloride has m 164-165o (from Me2CO/EtOH). [Butler & Angels J Am Chem Soc 79 3128 1957.]
