| Identification | More | [Name]
Triethylamine | [CAS]
121-44-8 | [Synonyms]
AKOS BBS-00004381
N,N-DIETHYLETHANAMINE
TEA
TETN
TRIETHYLAMINE
(C2H5)3N
(Diethylamino)ethane
ai3-15425
Ethanamine, N,N-diethyl-
ethanamine,n,n-diethyl-
N,N,N-Triethylamine
N,N-Diethylethanamin
n,n-diethyl-ethanamin
TEN
Triaethylamin
Triethylamin
Trietilamina
Diethylethanamine
Triethylamine, Free Base (1.08217)
Trethylamine | [EINECS(EC#)]
204-469-4 | [Molecular Formula]
C6H15N | [MDL Number]
MFCD00009051 | [Molecular Weight]
101.19 | [MOL File]
121-44-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Triethylamine is a colorless liquid. Strong
ammonia odor. | [Melting point ]
-115 °C | [Boiling point ]
90 °C | [density ]
0.728 | [vapor density ]
3.5 (vs air)
| [vapor pressure ]
51.75 mm Hg ( 20 °C)
| [FEMA ]
4246 | [refractive index ]
n20/D 1.401(lit.)
| [Fp ]
20 °F
| [storage temp. ]
2-8°C
| [solubility ]
water: soluble112g/L at 20°C | [form ]
Liquid | [pka]
10.75(at 25℃) | [color ]
Clear | [Specific Gravity]
0.725 (20/4℃) | [Odor]
Strong ammonia-like odor | [PH]
12.7 (100g/l, H2O, 15℃)(IUCLID) | [Relative polarity]
1.8 | [Stability:]
Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point. Incompatible with strong oxidizing agents, strong acids, ketones, aldehydes, halogenated hydrocarbons. | [explosive limit]
1.2-9.3%(V) | [Odor Threshold]
0.0054ppm | [Odor Type]
fishy | [Water Solubility ]
133 g/L (20 ºC) | [JECFA Number]
1611 | [Merck ]
14,9666 | [BRN ]
1843166 | [Henry's Law Constant]
1.79 at 25 °C (Christie and Crisp, 1967) | [Dielectric constant]
5.0（Ambient） | [Exposure limits]
NIOSH REL: IDLH 200 ppm; OSHA PEL: TWA 25 ppm (100 mg/m3); ACGIH
TLV: TWA 1 ppm, STEL 3 ppm (adopted). | [InChIKey]
ZMANZCXQSJIPKH-UHFFFAOYSA-N | [LogP]
1.65 | [Uses]
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. | [CAS DataBase Reference]
121-44-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Triethylamine(121-44-8) | [EPA Substance Registry System]
121-44-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,C | [Risk Statements ]
R11:Highly Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R35:Causes severe burns. | [Safety Statements ]
S3:Keep in a cool place .
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S29:Do not empty into drains .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1296 3/PG 2
| [WGK Germany ]
1
| [RTECS ]
YE0175000
| [F ]
34 | [Autoignition Temperature]
593 °F | [Hazard Note ]
Highly Flammable/Corrosive | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29211910 | [Safety Profile]
Moderately toxic by
ingestion and skin contact. Mildly toxic by
inhalation. Human systemic effects: visual
field changes. Experimental reproductive
effects. Mutation data reported. A skin and
severe eye irritant. Can cause kidney and
liver damage. A very dangerous fire hazard
when exposed to heat, flame, or oxidizers.
Explosive in the form of vapor when
exposed to heat or flame. Complex with
dinitrogen tetraoxide explodes below 0°C
when undduted with solvent. Exothermic
reaction with maleic anhydride above 150°C.
Can react with oxidzing materials.
Incompatible with N2O4. To fight fire, use
CO2, dry chemical, alcohol foam. When
heated to decomposition it emits toxic
fumes of NOx. | [Hazardous Substances Data]
121-44-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 0.46 g/kg (Smyth) | [IDLA]
200 ppm |
| Hazard Information | Back Directory | [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.] |
| Questions And Answer | Back Directory | [Outline]
Triethylamine (formula: C6H15N), also known as N, N-diethylethanamine, is the most simple tri-substituted uniformly tertiary amine, having typical properties of tertiary amines, including salifying, oxidation, Hing Myers test (Hisberg reaction) for triethylamine does not respond. It is colorless to pale yellow transparent liquid, with a strong smell of ammonia, slightly fuming in the air. Boiling point: 89.5 ℃, relative density (water = 1): 0.70, the relative density (Air = 1): 3.48, slightly soluble in water, soluble in alcohol, ether. Aqueous solution is alkaline, flammable. Vapor and air can form explosive mixtures, the explosion limit is 1.2% to 8.0%. It is toxic, with a strong irritant.
| [Uses]
Triethylamine is a clear, colorless liquid with an Ammonia or fish-like odor. It is used in making waterproofing agents, and as a catalyst, corrosion inhibitor and propellant.
It is mainly used as base, catalyst, solvent and raw material in organic synthesis and is generally abbreviated as Et3N, NEt3 or TEA. It can be used to prepare phosgene polycarbonate catalyst, polymerization inhibitor of tetrafluoroethylene, rubber vulcanization accelerator, special solvent in paint remover, enamel anti-hardener, surfactant, antiseptic, wetting agent, bactericides, ion exchange resins, dyes, fragrances, pharmaceuticals, high-energy fuels, and liquid rocket propellants, as a curing and hardening agent for polymers and for the desalination of seawater.
Consumption Quota of in medical industry:
Medicine
Consumption Quota(Unit: t/t)
Oxygen piperazine penicillin
0.584
Fluorine organism acid
10.00
Berberine hydrochloride
0.030
Adjacent benzene acetic acid
0.010
| [Production]
It is produced by ethanol and ammonia in the presence of hydrogen, in containing Cu-Ni-clay catalyst reactor under heating conditions (190 ± 2 ℃ and 165 ± 2 ℃) reaction. The reaction also produces ethylamine and diethylamine, products were condensed and then absorption by ethanol spray to obtain crude triethylamine, through the final separation, dehydration and fractionation, pure triethylamine is obtained.
| [Reaction]
- It can be used to reduce the alkali in the reaction.
| [Health Effects]
Triethylamine is a flammable liquid and a dangerous fire hazard. It can affect you when inhaled and by passing through the skin. Contact can severely irritate and bum the skin and eyes with possible eye damage. Exposure can irritate the eyes, nose and throat. Inhaling can irritate the lungs. Higher exposures may cause a build-up of fluid in the lungs (pulmonary edema), a medical mergency. It may cause a skin allergy and affect the liver and kidneys. |
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