General Description
A clear colorless liquid with a strong ammonia to fish-like odor. Flash point 20°F. Vapors irritate the eyes and mucous membranes. Less dense (6.1 lb/gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen when burned.
Reactivity Profile
TRIETHYLAMINE(121-44-8) reacts violently with oxidizing agents. Reacts with Al and Zn. 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.
Air & Water Reactions
Highly flammable. Soluble in water.
Health Hazard
Vapors irritate nose, throat, and lungs, causing coughing, choking, and difficult breathing. Contact with eyes causes severe burns. Clothing wet with chemical causes skin burns.
Potential Exposure
Triethylamine is and aliphatic amine
used as a solvent; corrosion inhibitor; in chemical synthesis;
and accelerator activators; paint remover; base in methylene
chloride or other chlorinated solvents. TEA is used to solubilize
2,4,5-T in water and serves as a selective extractant in
the purification of antibiotics. It is used to manufacture quaternary
ammonia compounds and octadecyloxymethyltriethylammonium
chloride; an agent used in textile treatment.
Fire Hazard
Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical
attention. If victim is conscious, administer water, or
milk. Do not induce vomiting. Give large quantities of
water and induce vomiting. Do not make an unconscious
person vomit. Medical observation is recommended for
24-48 hours after breathing overexposure, as pulmonary
edema may be delayed. As first aid for pulmonary edema,
a doctor or authorized paramedic may consider administering
a drug or other inhalation therapy.
Shipping
UN1296 Triethylamine, Hazard Class: 3; Labels:
3-Flammable liquid, 8-Corrosive material.
Incompatibilities
A strong base. Violent reaction with
strong acids; halogenated compounds; and strong oxidizers.
Attacks some forms of plastics, rubber and coatings.
Corrosive to aluminum, zinc, copper, and their alloys in the
presence of moisture. Reaction with nitrosating agents
(e.g., nitrites, nitrous gases, and nitrous acid) capable of
releasing carcinogenic nitrosamines.
Chemical Properties
Colorless to yellowish liquid; fishy aroma.
Chemical Properties
Triethylamine is a colorless liquid. Strong
ammonia odor.
Waste Disposal
Controlled incineration
(incinerator equipped with a scrubber or thermal unit to
reduce nitrogen oxides emissions).
Physical properties
Clear, colorless to light yellow flammable liquid with a strong, penetrating, ammonia-like odor.
Experimentally determined detection and recognition odor threshold concentrations were <400
μg/m3 (<100 ppbv) and 1.1 mg/m3 (270 ppbv), respectively (Hellman and Small, 1974). An odor
threshold concentration of 0.032 ppbv was determined by a triangular odor bag method (Nagata
and Takeuchi, 1990).
Application
Triethylamine (TEA, Et3N) is an aliphatic amine. It is used to catalytic solvent in chemical synthesis; accelerator activators for rubber; wetting, penetrating, and waterproofing agents of quaternary ammonium types; curing and hardening of polymers (e.g., corebinding resins); corrosion inhibitor; propellant.
Triethylamine has been used during the synthesis of:
5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridine
3′-(2-cyanoethyl)diisopropylphosphoramidite-5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridine
polyethylenimine600-β-cyclodextrin (PEI600-β-CyD)
It may be used as a homogeneous catalyst for the preparation of glycerol dicarbonate, via transesterification reaction between glycerol and dimethyl carbonate (DMC).
Definition
ChEBI: A tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.
Production Methods
Triethylamine is prepared by a vapor phase reaction of ammonia with ethanol or reaction of N,N-diethylacetamide with lithium aluminum hydride (Windholz et al 1983). It may also be produced from ethyl chloride and ammonia under heat and pressure (Hawley 1981) or by vapor phase alkylation of ammonia with ethanol (HSDB 1988). U.S. production is estimated at greater than 22,000 tons in 1972 (HSDB 1988).
Aroma threshold values
High strength odor, fishy type; recommend smelling in a 0.01% solution or less.
Industrial uses
Triethylamine is used as an anti-livering agent for urea- and melamine-based enamels and in the recovery of gelled paint vehicles (HSDB 1988). It is also used as a catalyst for polyurethane foams, a flux for copper soldering, and as a catalytic solvent in chemical synthesis (Hawley 1981). Triethylamine is used in accelerating activators for rubber; as a corrosion inhibitor for polymers; a propellant; wetting, penetrating, and waterproofing agent of quaternary ammonium compounds; in curing and hardening of polymers (i.e. core-binding resins); and as a catalyst for epoxy resins (Hamilton and Hardy, 1974).
Biochem/physiol Actions
Triethylamine is known to drive polymerization reaction. It acts as a source of carbon and nitrogen for bacterial cultures. Triethylamine is used in pesticides. Triethylamine can serve as an organic solvent.
Carcinogenicity
TEA was not mutagenic in bacterial assays,
but it did cause aneuploidy and chromosome
aberrations in rats.
Environmental Fate
Photolytic. Low et al. (1991) reported that the photooxidation of aqueous tertiary amine
solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium
and nitrate ions.
Chemical/Physical. Triethylamine reacted with NOx in the dark to form diethylnitrosamine. In
an outdoor chamber, photooxidation by natural sunlight yielded the following products:
diethylnitramine, diethylformamide, diethylacetamide, ethylacetamide, diethylhydroxylamine,
ozone, acetaldehyde, and peroxyacetyl nitrate (Pitts et al., 1978).
Metabolism
There have been few studies on the metabolism of industrially important aliphatic amines such as triethylamine. It is generally assumed that amines not normally present in the body are metabolized by monoamine oxidase and diamine oxidase (histaminase).
Ultimately ammonia is formed and will be converted to urea. The hydrogen peroxide formed is acted upon by catalase and the aldehyde formed is thought to be converted to the corresponding carboxylic acid by the action of aldehyde oxidase (Beard and Noe 1981).
Purification Methods
Dry triethylamine with CaSO4, LiAlH4, Linde type 4A molecular sieves, CaH2, KOH, or K2CO3, then distil it, either alone or from BaO, sodium, P2O5 or CaH2. It has also been distilled from zinc dust, under nitrogen. To remove traces of primary and secondary amines, triethylamine has been refluxed with acetic anhydride, benzoic anhydride, phthalic anhydride, then distilled, refluxed with CaH2 (ammonia-free) or KOH (or dried with activated alumina), and again distilled. Another purification method involved refluxing for 2hours with p-toluenesulfonyl chloride, then distilling. Grovenstein and Williams [J Am Chem Soc 83 412 1961] treated triethylamine (500mL) with benzoyl chloride (30mL), filtered off the precipitate, and refluxed the liquid for 1hour with a further 30mL of benzoyl chloride. After cooling, the liquid was filtered, distilled, and allowed to stand for several hours with KOH pellets. It was then refluxed with, and distilled from, stirred molten potassium. Triethylamine has been converted to its hydrochloride (see brlow), crystallised from EtOH (to m 254o), then liberated with aqueous NaOH, dried with solid KOH and distilled from sodium under N2. [Beilstein 4 H 99, 4 I 348, 4 II 593, 4 III 194, 4 IV 322.]
;