Diethylamine is a secondary amine , a derivative of ammonia , in the molecule of which two hydrogen atoms are replaced by ethyl radicals .
| Diethylamine | |
|---|---|
 | |
| Are common | |
| Systematic name | N-Ethylethanamine |
| Traditional names | diethylamine |
| Chem. formula | C 4 H 11 N |
| Rat formula | (C 2 H 5 ) 2 NH |
| Physical properties | |
| condition | colorless liquid |
| Molar mass | 73.14 g / mol |
| Density | 0.71 g / cm³ |
| Ionization energy | |
| Thermal properties | |
| T. melt. | -48 ° C |
| T. bale. | 56.3 ° C |
| T. aux. | -26 ° C |
| T. svpl. | 310 ° C |
| Etc. blast | 1.8-10.1% |
| Cr. pace. | 223.3 ° C |
| Cr. pressure | 36.6 atm |
| Like heat resistant. | 169.2 J / (mol · K) |
| Enthalpy of Education | -103.7 (w) kJ / mol |
| Steam pressure | |
| Chemical properties | |
| pK a | 1.17 * 10 -11 |
| Optical properties | |
| Refractive index | 1.3864 |
| Classification | |
| Reg. CAS number | 109-89-7 |
| PubChem | |
| Reg. EINECS number | 203-716-3 |
| Smiles | |
| Inchi | |
| RTECS | HZ8750000 |
| Chebi | |
| UN number | |
| ChemSpider | |
| Security | |
| LD 50 | 540 (rats, intragastrically) |
Content
Getting
In industry, they are prepared by reacting ethanol with ammonia (at 350–450 ° C and catalysis of Al 2 O 3 , SiO 2 ) or with ammonia in the presence of hydrogen (at 150–230 ° C and catalysis of Ni , Co , Cu , Re ). Diethylamine is also obtained by the interaction of diethyl ether with ammonia, reductive amination of acetaldehyde and ethylation of ammonia with ethyl chloride :
2C 2 H 5 Cl + 3NH 3 → (C 2 H 5 ) 2 NH + 2NH 4 Cl
In the laboratory, diethylamine is obtained by decomposition of 4-nitroso-N, N-diethylaniline with alkali [2] .
Physical Properties
Colorless liquid with a specific odor. Miscible with water, soluble in acetone , ethanol , diethyl ether .
At atmospheric pressure does not form azeotropic mixtures with water, methanol and ethanol.
Chemical Properties
Like other substituted amines, it has the basic properties - it reacts with acids to form diethylammonium salts:
(C 2 H 5 ) 2 NH + HCl → (C 2 H 5 ) 2 NH 2 Cl.
Nitrosated with nitrous acid to N-nitrosodiethylamine:
(C 2 H 5 ) 2 NH + HNO 2 → (C 2 H 5 ) 2 N-NO + H 2 O
Acylated by carboxylic acid chlorides and anhydrides to N, N-diethylamides.
Alkylated with alkyl halides, dimethyl sulfate .
With carbon disulfide in an alkaline medium gives N, N-diethyldithiocarbamates:
(C 2 H 5 ) 2 NH + CS 2 + KOH → (C 2 H 5 ) 2 NC (S) SK + H 2 O
When interacting with strong bases, cleaving the proton at the nitrogen atom, forms salts in the role of acid. For example, obtaining LDA by reaction with butyl lithium .
(C 2 H 5 ) 2 NH + LiC 4 H 9 → (C 2 H 5 ) 2 NLi + C 4 H 10
Application
For additives to motor fuels and oils, hardeners of epoxy resins, vulcanization accelerators, dyes, flotation reagents, repellents (e.g. diethyltoluamide ), pesticides, medicines (e.g. cordiamine , novocaine ), corrosion inhibitors (e.g. N, N-diethylurea, diethylammonium dinitrobenzoate). Also used to produce LSD-25 by mixing with lysergic acid to form d- lysergic acid diethylamide
Security
Toxicity
Irritating to mucous membranes of the upper respiratory tract and eyes. MPC 30 mg / m 3 .
Symptoms of poisoning in animals: irritation of the mucous membranes of the upper respiratory tract and eyes, excitation of the central nervous system with subsequent depression, tremor, convulsions, death with asphyxia. After 1 h of inhalation at 500-1000 mg / m 3 in rats, disturbances of conditioned and unconditioned reflexes lasted for a month, and at 300 mg / m 3 , short-term disturbances. Macroscopically: pulmonary edema, plethora of internal organs; histological: pronounced cell dystrophy and necrobiotic changes in the liver (Vasiliev).
Fire hazard
Combustible. Auto-ignition temperature 490 ° C. The concentration limits of ignition 2.2-14 volume%.
Notes
- ↑ 1 2 http://www.cdc.gov/niosh/npg/npgd0209.html
- ↑ Golodnikov G.V., Mandelstam T.V. Workshop on Organic Synthesis. - L .: ILU, 1976 p. 92-93
Literature
- Harmful chemicals: Nitrogen-containing organic compounds. - Under the general editorship of B. Kurlandsky, V. A. Filov - St. Petersburg: Chemistry, 1992. - P. 35
- Rabinovich V.A., Khavin Z. Ya. Brief chemical reference book. - L .: Chemistry, 1977 .-- S. 148
- Chemical encyclopedia. - T.5. - M .: Soviet Encyclopedia, 1999. - S. 493—494
See also
- Ethylamine
- Triethylamine