tert-Butylamine

Chemical properties

tert-Butylamine is a colorless liquid with a typical amine-like odor. It is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine. Butylamines are highly flammable, colorless liquids (n-turns yellow on standing) with ammoniacal or fishlike odors. tert-Butylamine is used in the preparation of insecticides, pharmaceuticals, oil additives, and rubber accelerators.

The Uses of tert-Butylamine

tert-butylamine is used as a precursor for the preparation of rubber accelerators, pharmaceuticals and dyes. It is employed in synthesis of N-tert-butyl-acetamide, isoquinolines, pyridines, decumbenine, sulfontes, sulfonamides and methyl beta-ketophosphonate. It is also used in the study the effect of amines in influencing atmospheric sulfuric acid - water nucleation, hydroamination of terminal alkynes and measuring the surface acidity of solid catalyst. It acts as an indicator molecule in the study of NMR -based pH determination method.

Definition

ChEBI: Tert-butylamine is a primary aliphatic amine that is ethylamine substituted by two methyl groups at position 1. It is a conjugate base of a tert-butylammonium.

Production Methods

tert-Butylamine is manufactured by reacting isobutylamine with sulfuric acid followed by cyanide to tert-butylformamide. Hydrolysis yields t-butylamine. It is used as a solvent and in organic syntheses.

Preparation

tert-Butylamine is produced commercially by direct amination of isobutylene using zeolite catalysts:
NH3 + CH2=C(CH3)2 → H2NC(CH3)3
The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste.
(CH3)2C=CH2 + HCN + H2O → (CH3)3CNHCHO
(CH3)3CNHCHO + H2O → (CH3)3CNH2 + HCO2H
In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide.

What are the applications of Application

Tert-Butylamine is also used for the production of herbicides, i.e., terbacil and the triazines terbutylazine, terbumeton, and terbutryn and insecticides (e.g., diafenthiuron). A derivative has also been proposed as stabilizer for cosmetics.

General Description

Tert-butylamine appears as a clear colorless liquid with an ammonia-like odor. Flash point 70°F. Less dense (at 6.2 lb / gal) than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.

Air & Water Reactions

Highly flammable. May be sensitive to air . Soluble in water.

Reactivity Profile

tert-Butylamine 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 is generated in combination with strong reducing agents, such as hydrides. Undergoes highly exothermic reaction with 2,2-dibromo-1,3-dimethylcyclopropanoic acid [J. Chem. Soc., 1, 1979, 2324].

Hazard

Skin irritant. Flammable, dangerous fire risk.

Health Hazard

Inhalation causes irritation of nose, mouth, and lungs. Ingestion causes irritation of mouth and stomach. Contact with liquid causes severe irritation of eyes and moderate irritation of skin.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.

Safety Profile

Poison by ingestion. Moderately toxic to humans by inhalation. A corrosive liquid. See also n-BUTYLAMINE and AMINES. Very dangerous fire hazard when exposed to heat or flame. Very exothermic reaction with 2,2-dibromo-l,3 dimethylcyclopropanoic acid. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

Alert: (n-isomer): Possible risk of forming tumors, suspected of causing genetic defects, suspected reprotoxic hazard, Primary irritant (w/o allergic reaction), (sec-isomer): Drug. n-Butylamine is used in pharmaceuticals; dyestuffs, rubber, chemicals, emulsifying agents; photography, desizing agents for textiles; pesticides, and synthetic agents. sec-Butylamine is used as a fungistate. tert-Butylamine is used as a chemical intermediate in the production of tert-Butylaminoethyl methacrylate (a lube oil additive); as an intermediate in the production of rubber and in rust preventatives and emulsion deterrents in petroleum products. It is used in the manufacture of several drugs

Shipping

UN1125 n-Butylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material. UN2014 Isobutylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material

Purification Methods

Dry it with KOH or LiAlH4, and/or distil it from CaH2 or BaO. [Beilstein 4 IV 657.]

Incompatibilities

May form explosive mixture with air. May accumulate static electrical charges, and may causeignition of its vapors. n-Butylamine is a weak base; reacts with strong oxidizers and acids, causing fire and explosion hazard. Incompatible with organic anhydrides; isocyanates, vinyl acetate; acrylates, substituted allyls; alkylene oxides; epichlorohydrin, ketones, aldehydes, alcohols, glycols, phenols, cresols, caprolactum solution. Attacks some metals in presence of moisture. The tert-isomer will attack some forms of plastics

Waste Disposal

Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner andscrubber. All federal, state, and local environmental regulations must be observed.