PRODUCTS

N-ETHYLETHANAMINE

N-Ethylethanamine is an organic compound with the formula (CH3CH2)2NH.
N-Ethylethanamine is a secondary amine.

CAS Number: 109-89-7
EC Number: 203-716-3
IUPAC Name: N-Ethylethanamine
Chemical Formula: C4H11N

Other names: DIETHYLAMINE, 109-89-7, N-Ethylethanamine, N,N-Diethylamine, Diethamine, Ethanamine, N-ethyl-, Diaethylamin, Dietilamina, Dwuetyloamina, Diethylamine, Diethyl-amine, Et2NH, CCRIS 4792, HSDB 524, (C2H5)2NH, EINECS 203-716-3, UNII-B035PIS86W, B035PIS86W, DTXSID6021909, CHEBI:85259, AI3-24215, MFCD00009032, DTXCID501909, EC 203-716-3, ethane, ethylamino-, Diethylamin, N-Ethyl-Ethanamine, Diaethylamin [German], Dietilamina [Italian], Dwuetyloamina [Polish], MELPHALAN IMPURITY K (EP IMPURITY), MELPHALAN IMPURITY K [EP IMPURITY], UN1154, dietylamine, di-ethylamine, N,N-Diethylamine, ethanamine, N-ethyl, Diethylamine, 98%, Diethylamine, BioXtra, HNEt2, DIETHYLAMINE [MI], DIETHYLAMINE [HSDB], Diethylamine, >=99.5%, CHEMBL1189, Diethylamine, LR, >=99%, (CH3CH2)2 NH, Diethylamine, p.a., 99.0%, Analytical Reagent,>99.0%(GC), STR00027, Tox21_202506, STL197470, Diethylamine, for synthesis, 99.0%, AKOS000269031, Diethylamine 2000 microg/mL in Water, UN 1154, Diethylamine, purum, >=99.0% (GC), NCGC00090709-01, NCGC00090709-02, NCGC00260055-01, CAS-109-89-7, Diethylamine, SAJ first grade, >=98.0%, D0462, Diethylamine [UN1154] [Flammable liquid], Diethylamine, SAJ special grade, >=99.0%, NS00002245, D89660, Diethylamine, puriss. p.a., >=99.5% (GC), Diethylamine, purified by redistillation, 99.5%, Q414196, J-002340, J-520311, InChI=1/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H, 5-Oxo-L-prolyl-L-glutaminyl-L-alpha-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamideN-ethylethanamine (1/1)

N-Ethylethanamine is a flammable, weakly alkaline liquid that is miscible with most solvents.
N-Ethylethanamine is a colorless liquid, but commercial samples often appear brown due to impurities.
N-Ethylethanamine has a strong ammonia-like odor.

Physical Description
N-Ethylethanamine appears as a clear colorless liquid with an ammonia-like odor.
Density 5.9 lb / gal.
Flash point -15°F. A respiratory irritant.
Corrosive to the eyes and skin. Vapors heavier than air.
Toxic oxides of nitrogen produced during combustion.

Physical properties
Colorless liquid with a fishy, ammonia-like odor.
Experimentally determined detection and recognition odor threshold concentrations were 60 μg/m3 (20 ppbv) and 180 μg/m3 (60 ppbv), respectively (Hellman and Small, 1974).
N-Ethylethanamine is a very strong base in aqueous solution (pKb = 3.0).
Its chemistry is governed by the unshared electron pair on the nitrogen, thus it tends to react with acids to form salts.

Description
N-Ethylethanamine is a colourless, strongly alkaline, fish odour liquid, and highly inflammable.
N-Ethylethanamine has an ammonia-like odour and is completely soluble in water.
On burning, N-Ethylethanamine releases ammonia, carbon monoxide, carbon dioxide, and nitrogen oxides.
N-Ethylethanamine is incompatible with several chemical substances such as strong oxidisers, acids, cellulose nitrate, some metals, and dicyanofuroxan.
N-nitrosamines, many of which are known to be potent carcinogens, may be formed when N-Ethylethanamine comes in contact with nitrous acid, nitrates, or atmospheres with high nitrous oxide concentrations.
The applications of N-Ethylethanamine are numerous.

N-Ethylethanamine is used in the production of pesticides.
N-Ethylethanamine is used in a mixture for the production of DEET which goes into the repellents that are found readily in supermarkets for general use.
N-Ethylethanamine is also mixed with other chemicals to form Diethylaminoethanole, which is used mainly as a corrosion inhibitor in water treatment facilities as well as production of dyes, rubber, resins, and pharmaceuticals. N-Ethylethanamine is also used in manufacture of basic chemicals and pharmaceuticals.

Occurrence
N-Ethylethanamine occurs in low concentrations in food and other biological materials.
Concentrations (in p.p.m.) in fresh products include: spinach (15), apples (3), butterbeans (2.4), shelled peas (0.1), bean salad (1.5) and red cabbage (2.4) (HSDB 1989).
Pickled vegetables contain 0-3.2 p.p.m. N-Ethylethanamine while concentrations (in p.p.m.) in other materials include herring (0-5.2), barley (5.7), hops (3.1), boiled beef (2), tobacco leaf (0.1-35) and cigarette smoke concentrate (0-0.4).
Interest in the occurrence of N-Ethylethanamine in foods arises in part because of its possible formation of a carcinogenic N-nitroso derivative (Neurath et al 1977).
N-Ethylethanamine has been reported in the exhaust from a gasoline engine (Hampton et al 1982).

Structure
N-Ethylethanamine is the smallest and simplest molecule that features a supramolecular helix as its lowest energy aggregate.
Other similarly sized hydrogen-bonding molecules favor cyclic structures.

Air & Water Reactions
Highly flammable.
Soluble in water.
Sensitive to heat.
May be sensitive to prolonged exposure to air.

Molecular Weight: 73.14
XLogP3: 0.6
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 2
Exact Mass: 73.089149355
Monoisotopic Mass: 73.089149355
Topological Polar Surface Area: 12 Å²
Heavy Atom Count: 5
Complexity: 11.1
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Uses
In flotation agents, resins, dyes, resins, pesticides, rubber chemicals, and pharmaceuticals; selective solvent; polymerization and corrosion inhibitors; petroleum chemicals; electroplating; organic synthesis.

N-Ethylethanamine is manufactured by heating ethyl chloride and alcoholic ammonia under pressure or by hydrogenation of aziridines in the presence of catalysts.
DEA is used as a solvent, as a rubber accelerator, in the organic synthesis of resins, dyes, pesticides, and pharmaceuticals, in electroplating, and as a polymerization inhibitor.
Other applications include uses as a corrosion inhibitor.
It was reported noneffective as a skin depigmentator.

In the rubber and petroleum industry; in flotation agents; in resins, dyes, pharmaceuticals

N-Ethylethanamine, like many of the other short chain aliphatic amines, has achieved widespread industrial use as an intermediate in the manufacture of a number of commercial products.
Among these are included insecticides, pharmaceuticals, textile finishing agents, and corrosion inhibitors (Hawley 1981; Schweizer et al 1978).
It is used as a polymerization inhibitor and/or catalyst in the polymer industry and in the manufacture of surfactants and rubber processing accelerators.
This amine also is useful as a depilatory agent for animal skins, as a selective solvent for the removal of impurities from oils, fats, and waxes, and as a flotation agent in the petroleum industry (NIOSH/OSHA 1981; HSDB 1989).

Production Methods
N-Ethylethanamine is produced using the three methods also used for the manufacture of ethylamine with very slight modification.
The most widely used method is the passing of ammonia and ethanol over a catalyst such as alumina or silica (Schweizer et al 1978).
N-Ethylethanamine can be separated from the mixture by selective distillations and extractions.
This secondary amine can also be produced by the other two methods which involve: 1) passing ammonia, ethanol, and hydrogen over a dehydrogenation catalyst; and 2) passing ammonia and an aldehyde or ketone and hydrogen over a hydrogenation catalyst.
U.S. production in 1984 is estimated at 19.7 million pounds (HSDB 1989).

Sampling Procedures
Analyte: N-Ethylethanamine; matrix: air; procedure: adsorption on silica gel, desorption with 0.2 N sulfuric acid in 10% methanol.
Analyte: aliphatic amines; matrix: air; procedure: adsorption on silica gel; elution with acid.
A sampling and analytical procedure for methyl-, dimethyl-, ethyl-, and N-Ethylethanamine was developed in order to avoid problems typically encountered in the sampling and analysis of low molecular weight aliphatic amines.
Samples are collected with adsorbent tubes containing Amberlite XAD-7 resin coated with the derivatizing reagent, NBD chloride (7-chloro-4-nitrobenzo-2-oxa-1,3-diazole).

Analysis is performed by HPLC with the use of a fluorescence and/or UV/visible detector.
All four amines can be monitored simultaneously, and neither collection nor storage is affected by humidity.
Samples are stable at room temperature for at least two weeks.
The methodology has been tested for each amine at sample loadings equivalent to air concn ranges of 0.5 to 30 ppm for a sample volume of 10 liters.
The method shows promise for determining other airborne primary and secondary low molecular weight aliphatic amines.