ChemicalBook > Product Catalog > Organic Chemistry > Amides > Acyclic polyamines and their derivatives > Diethylamine
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 n
- Flash point:−20 °F
- storage temp. Store below +30°C.
- solubility H2O: soluble1M at 20°C, clear, colorless
- pka11.02(at 40℃)
- form Liquid
- color Clear colorless
- Relative polarity0.145
- PH13 (100g/l, H2O, 20℃)
- PH RangeStrong alkaline
- OdorAmmoniacal; sharp, fishy.
- Odor Threshold0.048ppm
- explosive limit2.0-11.8%(V)
- Water Solubility soluble
- Sensitive Air Sensitive
- Merck 14,3111
- BRN 605268
- Henry's Law Constant2.56(x 10-5 atm?m3/mol) at 25 °C (Christie and Crisp, 1967)
- Exposure limitsNIOSH 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.
- CAS DataBase Reference109-89-7(CAS DataBase Reference)
- NIST Chemistry ReferenceEthanamine, N-ethyl-(109-89-7)
- EPA Substance Registry SystemDiethylamine (109-89-7)
- Hazard Codes F,C
- Risk Statements 11-20/21/22-35
- Safety Statements 16-26-29-36/37/39-45-3
- RIDADR UN 1154 3/PG 2
- WGK Germany 1
- RTECS HZ8750000
- F 10-23
- Autoignition Temperature594 °F
- TSCA Yes
- HazardClass 3
- PackingGroup II
- HS Code 29211990
- Hazardous Substances Data109-89-7(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 540 mg/kg (Smyth)
Diethylamine Usage And Synthesis
- DescriptionDiethylamine 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. 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. The applications of Diethylamine are numerous. 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. Diethylamine 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. Diethylamine is also used in manufacture of basic chemicals and pharmaceuticals.
- Physical propertiesColorless 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.
- OccurrenceDiethylamine 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).
- UsesIn flotation agents, resins, dyes, resins, pesticides, rubber chemicals, and pharmaceuticals; selective solvent; polymerization and corrosion inhibitors; petroleum chemicals; electroplating; organic synthesis.
- UsesDiethylamine 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.
- UsesIn the rubber and petroleum industry; in flotation agents; in resins, dyes, pharmaceuticals
- Production MethodsDiethylamine 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). Diethylamine 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).
- DefinitionChEBI: A secondary aliphatic amine where both N-substituents are ethyl.
- General DescriptionA 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 ReactionsHighly flammable. Soluble in water. Sensitive to heat. May be sensitive to prolonged exposure to air.
- Reactivity ProfileDiethylamine is a colourless, strongly alkaline, fish odour liquid, and highly inflammable. It has an ammonia-like odour and is completely soluble in water.Causes ignition on contact with cellulose nitrate. Explodes on contact with dicyanofurazan or dicyanofuroxan. Attacks some forms of plastics, rubber and coatings.
On burning, diethylamine releases ammonia, carbon monoxide, carbon dioxide, and nitrogen oxides. 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 HazardDiethylamine 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.
- Chemical ReactivityReactivity 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 usesDiethylamine, 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 ProfileModerately 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.
- CarcinogenicityNo evidence of mutagenicity was seen
in Ames bacterial assays.8 Diethylamine has
an ammonia-like odor that is detectable at
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 FatePhotolytic. 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).
- MetabolismLittle 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).
- storageDiethylamine 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 MethodsDry 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.
- PrecautionsOccupational 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
- Preparation Products4-phenyl-1-(p-tolylsulphonyl)piperidine-4-carboxylic acid Montelukast4'-Iodoacetophenone4,6-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-AMINE2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBONITRILE1,4,6-Trimethyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine ,97%7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINEDiethylcarbamyl chlorideBenzyl cinnamate2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE2-AMINO-4,5-DIMETHYL-THIOPHENE-3-CARBONITRILE3-(DIETHYLAMINO)PROPANOIC ACIDBenzyl salicylate5-AMINO-3-METHYL-THIOPHENE-2,4-DICARBOXYLIC ACID DIMETHYL ESTER(5-BROMO-PYRIMIDIN-2-YL)-DIETHYL-AMINE3-Cyano-4,6-dimethyl-2-hydroxypyridineN,N-DIETHYL-4-METHYL-1-PIPERAZINECARBOXAMIDEFast Red ITR2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACIDEthyl ziram Etamsylate2-Chloro-3-cyano-4,6-dimethylpyridineLidocaine hydrochloride1,1-diethylguanidine hydrochlorideN,N-DiethylcyanoacetamideProcaine hydrochlorideBIS(DIETHYLAMINO)CHLOROPHOSPHINEDiethylamine hydrochlorideDIETHYLCYANAMIDEESFENVALERATE FREE ACID METABOLITEFAST RED SALT ITR3-Diethylaminopropylaminecoating adhesive tiemao 102N,N-Diethyl-3-methylbenzamideN,N-DIETHYLNICOTINAMIDEDisulfiramDIETHYLAMMONIUM DIETHYLDITHIOCARBAMATEN,N-Diethyl-2-chloropropionamideTRIS(DIETHYLAMINO)PHOSPHINE
- Raw materialsEtanolAmmoniaHydrogen2-Ethylaniline2-(Ethylamino)ethanol
- N,N-DIETHYL-N-PROPYLAMINE [N-(N-PROPYL)DIETHYLAMINE],N,N-DIETHYL-N-PROPYLAMINE [N-(N-PROPYL)DIETHYLAMINE] 16A hydroxytestosterone--dea schedule*iii item N-(3-[1-BENZYL-2-(METHYLAMINO)ETHOXY]PROPYL)-N,N-DIETHYLAMINE,N-(3-[1-BENZYL-2-(METHYLAMINO)ETHOXY]PROPYL)-N,N-DIETHYLAMINE ecgonine hydrochloride--dea schedule*ii item ACROLEIN DEA N-[(5-bromo-1-benzothien-2-yl)methyl]-2-chloro-N-ethylethanamine N-(1-BENZOTHIEN-3-YLMETHYL)-2-CHLORO-N-ETHYLETHANAMINE STEARAMIDOETHYL DIETHYLAMINE 10G [R],STEARAMIDOETHYL DIETHYLAMINE 10G [R] N-([5-(AMINOMETHYL)-1,2,4-OXADIAZOL-3-YL]METHYL)-N-ETHYLETHANAMINE DIETHYLAMINE CHLORHYDRATE,DIETHYLAMINE CHLORHYDRATE 2-Ethylaniline N-Propylcyclopropanemethylamine N-(2-CHLOROETHYL)ACETAMIDE N,N-Diethylchloroacetamide N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) N-Chloroethyl-N-ethylaniline Perfluorotributylamine LABOTEST-BB LT00452529
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