Ethylene glycol dinitrate (dinitroethylene glycol , nitroglycol, abbreviated EGDN) is an organic compound of the formula C 2 H 4 O 6 N 2 ((CH 2 ONO 2 ) 2 ), an ester of nitric acid and ethylene glycol dihydric alcohol, is an oily liquid. EGDN is a powerful explosive (BB). Other names are rare: dinitroglycol, glycol dinitrate . Vapors are very toxic if inhaled, can penetrate intact skin. When ingested, it causes poisoning up to death. Very sensitive to shock, friction, heat. Flying.
| Ethylene glycol dinitrate | |
|---|---|
| Are common | |
| Systematic name | 1,2-dinitroxyethane |
| Abbreviations | EGDN, NGL |
| Traditional names | ethylene glycol dinitrate, nitroglycol |
| Chem. formula | C 2 H 4 N 2 O 6 |
| Physical properties | |
| condition | liquid |
| Molar mass | 152.063 ± 0.0041 g / mol |
| Density | 1.49 g / cm³ |
| Thermal properties | |
| T. melt. | -22.3 ° C |
| T. bale. | |
| T. decomp. | 114 ° C |
| T. aux. | |
| T. svpl. | 217 ° C |
| Steam pressure | |
| Chemical properties | |
| Solubility in water | 5.6 g / 100 ml |
| Optical properties | |
| Refractive index | 1,4452 |
| Classification | |
| Reg. CAS number | 628-96-6 |
| PubChem | |
| Reg. EINECS number | 211-063-0 |
| Smiles | |
| Inchi | |
| RTECS | |
| ChemSpider | |
| Security | |
| LD 50 | 540 mg / kg (mouse, oral), 460 mg / kg (rat, oral), 3800 mg / kg (rat, subcutaneous) |
| Toxicity | toxic especially by inhalation |
Content
Physico-chemical properties
Transparent oily rather volatile liquid . Density at 20 ° C 1.489 g / cm ³, solidification temperature −21.7 ° C. It is slightly hygroscopic, soluble in ethanol , methanol , diethyl ether, nitrobenzene , acetone and many other solvents. Solubility in water 0.5% at 25 ° C. Viscosity at 20 ° C - 0.421 s Pa * s . Volatility is significantly higher than that of nitroglycerin (2.2 mg / cm2 / h - 20 times more, (according to other sources - 8 times and 13 times according to Stetbacher). Colloxylin easily gelates at ordinary temperature and relatively quickly. While gelatinization of nitroglycerin requires heating. When heated with alkalis, EHD is saponified. It forms eutectic mixtures with nitroglycerin with a very low melting point.
Susceptibility to heat and external influences
t square –22.5 ° C. t bale. 197.5 ° C. In vacuum, EGDN boils without decomposition at 95 ° C and can easily be distilled with water vapor.
Attitude to heating: By carefully heating small amounts, EHD can be brought to evaporation without explosion or flash. Quickly heated on a metal plate flashes with a slight explosion. Heated to 150 ° C begins to produce yellow fumes - Nitrogen oxides . When heated to 170 ° C, in small quantities it quickly decomposes with a slight flash, in large quantities it explodes.
Chemical resistance: EGDN is much more stable than nitroglycerin. At a temperature of 72 ° C, it can withstand an Abel sample for an hour (NHC for 10-15 minutes). The seemingly lower initial resistance of EGDN is due to a slight dissociation of its vapor.
Sensitivity to shock: ~ 20 cm (according to other sources 7-10 cm) for a load of 2 kg (nitroglycerin - 4 cm, TEN - 17 cm).
Susceptibility to detonation: EGDN is much easier to detonate than nitroglycerin. Its expansion (with water blockage), in comparison with other homologous esters in the Trautzl bomb, is presented below:
| GR capsules | EGDN | Nitroglycerine | Methyl nitrate |
|---|---|---|---|
| No. 1 (0.3 g.) | 465 ml (71%) | 190 ml (32%) | 520 ml (84%) |
| No. 3 (0.54 g.) | - | 225 ml (38%) | - |
| No. 6 (1.0 g.) | - | 460 ml (78%) | - |
| No. 8 (2.0 g.) | 650 ml (100%) | 590 ml (100%) | 620 ml (100%) |
* In these experiments, the difference in the actions of the capsules themselves was not taken into account, because she is insignificant.
From the table you can see that EGDN detonates much more easily and completely even from the smallest capsule. Presumably this is a lower viscosity. A high detonation velocity is possible with a charge diameter of more than 2.7 mm.
Explosive properties
- Explosion heat: 6.8 MJ / kg.
- Heat of formation: -358.2 kcal / kg.
- Enthalpy of formation: -381.6 kcal / kg.
- Explosion temperature: 4503 K (approximately 4230 ° C).
- Knock speed: 7200 m / s. According to other sources, 8300 m / s - in a steel pipe with a diameter of 35 mm. It can detonate in low speed mode (1500-2000 m / s).
- Brisance: 129% (61.9 g of sand) of TNT (sand sample), according to Hess 115% (18.9 mm) of TNT.
- High explosiveness in the Pb block : EGDN has a very high working capacity: 620 ml with sand plugging (650 ml with water).
- Performance in a ballistic mortar: 127-137% of TNT.
- Volume of explosion products: 737 l / kg, ( NGC 713 l / kg, thickness 730 l / kg).
- Critical diameter: 2 mm, moreover, the detonation is low speed and extends to no more than 100 diameters (20 cm)
Getting
First obtained by Henry in 1870 . The main methods of obtaining:
- esterification of ethylene glycol
- ethylene nitration
To obtain nitroglycol, dynamite brand ethylene glycol is used, which is taken in 20 parts by weight per 100 parts by weight of nitrating mixture of 50% nitric acid with a strength of 90 ... 98% and 50% sulfuric acid with a strength of 90-98%.
Ethylene glycol nitration is carried out on equipment and by technology (temperature and other conditions) to obtain nitroglycerin (see).
The separation of nitroglycol is carried out in the same way as the separation of nitroglycerin with the difference that the separated nitroglycol is taken into a container with 2 times the amount of cold water, and due to the lower viscosity of nitroglycol compared to nitroglycerin, the separation is faster than that of nitroglycerin.
The washing of nitroglycol is carried out in the same way as nitroglycerin, with the difference that only cold washing liquids are used due to the high volatility of nitroglycol. The washing liquid for each washing is taken in an amount equal to the amount of nitroglycol by volume. The washed nitroglycol is filtered through a filter.
Obtaining nitroglycol is a great danger. But less than nitroglycerin production.
Application
Henry was first obtained in 1870. In 1914 it was applied in Germany as an antifreeze to dynamite. During the 2nd world. war due to lack of glycerin was used as a substitute for nitroglycerin in smokeless gunpowder. Nitroglycol gunpowder had a short shelf life due to the volatility of EGDN, however, in wartime conditions this was justified. Gunpowder on EGDN burn approximately 2 times slower than on nitroglycerin. It is used in mixtures with nitroglycerin in the production of non-freezing dynamites for use at low temperatures (usually in a ratio of 50:50). EXPLOSIVES using ethylene glycol dinitrate: GOMA 2 ECO ; It has also found widespread use in many nitroglycerin (nitroglycol) explosives: gelatin dynamites, explosive jelly, carbonites, detonites, as an additive in ASVV, etc. In January 2003, a terrorist attack occurred on the Raushskaya embankment near the building of the State Unitary Enterprise Mosgortrans.
Toxicity EGDN
In acute poisoning - headache , hypotension , tachycardia , nausea , vomiting . Described dozens of cases of sudden death of relatively young and healthy workers, long contact with EGDN and nitroglycerin in the production of explosives. EGDN is more volatile than nitroglycerin and is more rapidly absorbed through the skin ; therefore consider that he plays a major role. The death usually occurred 30-60 hours after the termination of work (Sunday or Monday morning) with the occurrence of angina pectoris and acute heart failure [2] .
A number of other neurological disorders were revealed in workers engaged in the manufacture of EGDN: insomnia , bradycardia , depression , fainting , independent of vascular insufficiency [2] . There is an opinion that under the influence of EGDN the synaptic transmission and metabolic processes in the brain are disrupted - in its intermediate section [3] .
EGDN easily penetrates the skin. Absorption through the skin contributes to the development of EHD poisoning in workers and is even its main cause. Workers using protective rubber gloves found 0.1-1 mg EGDN on the skin of their hands [4] . The minimum dose that causes pain in humans when applied to the skin is 1.8-3.5 ml of a 1% alcohol solution of EGDN [5] . MAC in the working area: 3 mg / m 3 .
If EGDN gets inside with food or drink, a severe headache, fainting, and after a few minutes death from cardiac arrest immediately occur.
MLD = 0.5 ml when taken orally.
Links
- http://chemistry-chemists.com/N2_2013/P1/pirosprawka2012.pdf
- https://exploders.info/articles/0/33.html
- https://exploders.info/books/14.html
- http://chemistry-chemists.com/N6_2011/P16/ChemistryAndChemists_6_2011-P16-5.html
- https://exploders.info/sprawka/90.html
- http://pirochem.net/index.php?id1=3&category=azgotov-prim-vv&author=shtetbaher-a&book=1936
- https://exploders.info/books/14.html
- https://exploders.info/books/18.html
Notes
- ↑ 1 2 3 http://www.cdc.gov/niosh/npg/npgd0273.html
- ↑ 1 2 Harmful substances in industry. Handbook for chemists, engineers and doctors / Ed. N.V. Lazareva and I.D. Gadaskina. - Ed. 7th, per. and additional .. - Leningrad: Chemistry, 1977. - T. Volume III. Inorganic and organoelemental compounds. - 608 p.
- ↑ Stýblová V. [The neurotoxic effects of explosives] (Czech) // Ceskoslovenska neurologie. - 1966. - Sv. 29 , č. 6 . - S. 378-381 . - PMID 5979126 .
- ↑ Einert C., Adams W., Crothersab R., Moorea H., Ottoboni F. Exposure to Mixtures of Nitroglycerin and Ethylene Glycol Dinitrate (Eng.) // American Industrial Hygiene Association Journal. - 1963. - Vol. 24 , no. 5 . - P. 435-447 . - DOI : 10.1080 / 00028896309343245 .
- ↑ Polson CJ, Tattersall RN Clinicals Toxicology. - English Universities Press, 1959. - P. 589.