| | Diethylamine Basic information |
| | Diethylamine Chemical Properties |
| Melting point | -50 °C (lit.) | | Boiling point | 55 °C (lit.) | | density | 0.707 g/mL at 25 °C (lit.) | | vapor density | 2.5 (vs air) | | vapor pressure | 14.14 psi ( 55 °C) | | refractive index | n20/D 1.385(lit.) | | Fp | −20 °F | | storage temp. | Store below +30°C. | | solubility | H2O: soluble1M at 20°C, clear, colorless | | pka | 11.02(at 40℃) | | form | Liquid | | color | Clear colorless | | Odor | Ammoniacal; sharp, fishy. | | Relative polarity | 0.145 | | PH | 13 (100g/l, H2O, 20℃) | | PH Range | Strong alkaline | | Odor Threshold | 0.048ppm | | Odor Type | ammoniacal | | explosive limit | 2.0-11.8%(V) | | Water Solubility | soluble | | Sensitive | Air Sensitive | | Merck | 14,3111 | | BRN | 605268 | | Henry's Law Constant | 2.56(x 10-5 atm?m3/mol) at 25 °C (Christie and Crisp, 1967) | | Exposure limits | NIOSH REL: TWA 10 ppm (30 mg/m3), STEL 25 ppm (75 mg/m3), IDLH 200
ppm; OSHA PEL: TWA 25 ppm; ACGIH TLV: TWA 5 ppm, STEL 15 ppm (adopted). | | Stability: | Stable. Highly flammable. Incompatible with strong oxidizing agents. | | InChIKey | HPNMFZURTQLUMO-UHFFFAOYSA-N | | LogP | 0.58 at 20℃ | | CAS DataBase Reference | 109-89-7(CAS DataBase Reference) | | NIST Chemistry Reference | Ethanamine, N-ethyl-(109-89-7) | | EPA Substance Registry System | Diethylamine (109-89-7) |
| | Diethylamine Usage And Synthesis |
| Description | Diethylamine is a colourless, strongly alkaline, fish odour liquid, and highly inflammable. It has an ammonia-like odour and is completely soluble in water. On burning, diethylamine releases ammonia, carbon monoxide, carbon dioxide, and nitrogen oxides. Diethylamine is used in the production of pesticides. It is used in a mixture for the production of DEET which goes into the repellents that are found readily in supermarkets for general use. | | 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). Diethylamine 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.
| | Occurrence | Diethylamine 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. diethylamine 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 diethylamine in foods arises in part because of its possible formation
of a carcinogenic N-nitroso derivative (Neurath et al 1977). Diethylamine has
been reported in the exhaust from a gasoline engine (Hampton et al 1982). | | Uses | Diethylamine 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. | | Production Methods | Diethylamine is produced using the three methods also used for the manufacture of ethylamine with very slight modification.
Diethylamine Synthesis
1. N,N-Diethyl-3-methylbenzamide + Ethylene Glycol + NaOH + Heat
2. Ethylchloride + Ammonia (forms diethylamine HCL)
3. Ethanol + Ammonia + Sulfuric Acid
The most widely used method is the passing of ammonia and ethanol over a catalyst such as alumina or silica (Schweizer et al 1978). Diethylamine can be separated from the mixture by selective distillations and extractions. | | Definition | ChEBI: Diethylamine is a secondary aliphatic amine where both N-substituents are ethyl. It is a conjugate base of a diethylammonium. | | General Description | 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. | | Air & Water Reactions | Highly flammable. Soluble in water. Sensitive to heat. May be sensitive to prolonged exposure to air. | | Reactivity Profile | It 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 diethylamine comes in contact with nitrous acid, nitrates, or atmospheres with high nitrous oxide concentrations. | | Health Hazard | Diethylamine can be harmful if it is inhaled, swallowed, or in contact with skin.
Vapors can irritate the eyes and cause irritation of the respiratory tract, leading to
coughing and chest pain. Liquid diethylamine can cause severe burns to the eyes
and skin. Vision became misty and halos appeared several hours after workmen
were exposed to the vapors of amines such as diethylamine (Grant 1986). The
edema of the corneal epithelium, which is principally responsible for the disturbances
in vision, clears after one or more days, depending on the severity of
exposure. Photophobia and discomfort from roughness of the corneal surface also
can occur after greater exposure to the amine. | | Flammability and Explosibility | Highlyflammable | | Chemical Reactivity | Reactivity with Water No reaction; Reactivity with Common Materials: No hazardous reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | | Industrial uses | Diethylamine, 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). | | Safety Profile | Moderately toxic by
ingestion, inhalation, and skin contact. A
skin and severe eye irritant. Exposure to
strong vapor can cause severe cough and
chest pains. Contact with liquid can damage
eyes, possibly permanently; contact with
skin causes necrosis and vesciculation. A
very dangerous fire hazard when exposed to
heat, flame, or oxidizers. To fight fire, use
alcohol foam, CO2, dry chemical. Explodes
on contact with dicyanofurazan. Violent
reaction with sulfuric acid. Ignites on
contact with cellulose nitrate of sufficiently
high surface area. When heated to
decomposition it emits toxic fumes of NOx.
See also MINES. | | Carcinogenicity | No evidence of mutagenicity was seen
in Ames bacterial assays.8 Diethylamine has
an ammonia-like odor that is detectable at
0.13ppm.
The 2003 ACGIH threshold limit valuetime-
weighted average (TLV-TWA) for
diethylamine is 5ppm (15mg/m3) with
a short-term excursion limit of 15ppm
(45mg/m3) and an A4-not classifiable as a
human carcinogen designation; there is a notation
for skin absorption. | | Environmental fate | Photolytic. Low et al. (1991) reported that the photooxidation of aqueous secondary amine
solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium
and nitrate ions.
Chemical/Physical. Diethylamine reacted with NOx in the dark forming diethylnitrosamine. In
an outdoor chamber, photooxidation by natural sunlight yielded the following products:
diethylnitramine, diethylformamide, diethylacetamide, ethylacetamide, ozone, acetaldehyde, and
peroxyacetyl nitrate (Pitts et al., 1978).
Reacts with mineral acids forming water-soluble salts (Morrison and Boyd, 1971). | | Metabolism | Little information is available regarding the metabolism of diethylamine. The
amine can be readily absorbed from the respiratory and gastrointestinal tract. It has
been reported that following oral administration of diethylamine hydrochloride to
humans, much of the amine was recovered in the urine (Beard and Noe 1978). This
suggests that it is not readily metabolized and, therefore, may not be a substrate for
monoamine oxidase. When administered intraperitoneally to rats, it was moderately
inhibitory with respect to liver monoamine oxidase (Valiev 1974). Diethylamine
may serve as a precursor for the formation of the reportedly carcinogenic
N-nitrosoamines and, indeed, when a diethylamine containing liquid was examined
for nitrosation reactions under simulated conditions of the human stomach,
N-nitrosodiethylamine was formed (Ziebarth 1985). | | storage | Diethylamine should be protected from physical damage. It should be kept stored in a
cool, dry, well-ventilated location, away from incompatible chemical substances and away
from fi re hazard and smoking areas. The containers should be bonded and grounded for
transfer to avoid static sparks. Storage and use areas should be no smoking areas. | | Purification Methods | Dry diethylamine with LiAlH4 or KOH pellets. Reflux with, and distil it from, BaO or KOH. Convert it to the p-toluenesulfonamide and crystallise to constant melting point from dry pet ether (b 90-120o), then hydrolyse with HCl, excess NaOH is added, and the amine is passed through a column of activated alumina. Redistil the amine and dry it with activated alumina before use [Swift J Am Chem Soc 64 115 1942]. [Beilstein 4 III 313.] § A polystyrene diethylaminomethyl supported version is commercially available. | | Precautions | Occupational workers and users should be very careful during the use and chemical management
of diethylamine. Workers should wear impervious protective clothing, including
boots, gloves, a laboratory coat, apron or coveralls, as appropriate, to prevent skin contact. The chemical is very hazardous, corrosive, and harmful, and is a very flammable liquid
and vapor. Exposures to vapor may cause fl ash fi re. It causes burns and adverse effects
to the cardiovascular system. Workers should use chemical safety goggles and a full-face
shield to avoid splashing of the chemical substance. An eye-wash fountain and quickdrench
facilities in the work area should be maintained by the chemical management unit. |
| | Diethylamine Preparation Products And Raw materials |
| Raw materials | Ethanol-->Ammonia-->Hydrogen-->2-Ethylaniline-->2-(Ethylamino)ethanol | | Preparation Products | 4-phenyl-1-(p-tolylsulphonyl)piperidine-4-carboxylic acid-->Montelukast-->4'-Iodoacetophenone-->4,6-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-AMINE-->2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE-->2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBONITRILE-->1,4,6-Trimethyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine ,97%-->7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINE-->Diethylcarbamyl chloride-->Benzyl cinnamate-->2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE-->2-AMINO-4,5-DIMETHYL-THIOPHENE-3-CARBONITRILE-->3-(DIETHYLAMINO)PROPANOIC ACID-->Benzyl salicylate-->5-AMINO-3-METHYL-THIOPHENE-2,4-DICARBOXYLIC ACID DIMETHYL ESTER-->(5-BROMO-PYRIMIDIN-2-YL)-DIETHYL-AMINE-->3-Cyano-4,6-dimethyl-2-hydroxypyridine-->DIETHYLCARBAMAZINE-->Fast Red ITR-->2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID-->Ethyl ziram-->Etamsylate-->2-Chloro-3-cyano-4,6-dimethylpyridine-->Lidocaine hydrochloride-->1,1-diethylguanidine hydrochloride-->N,N-Diethylcyanoacetamide-->Procaine hydrochloride-->BIS(DIETHYLAMINO)CHLOROPHOSPHINE-->Diethylamine hydrochloride-->DIETHYLCYANAMIDE-->ESFENVALERATE FREE ACID METABOLITE-->FAST RED SALT ITR-->3-Diethylaminopropylamine-->coating adhesive tiemao 102-->N,N-Diethyl-m-toluamide-->N,N-DIETHYLNICOTINAMIDE-->Disulfiram-->DIETHYLAMMONIUM DIETHYLDITHIOCARBAMATE-->N,N-Diethyl-2-chloropropionamide-->TRIS(DIETHYLAMINO)PHOSPHINE |
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