Difference between revisions of "Ethyl nitrate"
Diachrynic (Talk | contribs) |
|||
| Line 113: | Line 113: | ||
===Chemical=== | ===Chemical=== | ||
Ethyl nitrate burns in air releasing carbon dioxide, water vapors and nitrogen oxides. | Ethyl nitrate burns in air releasing carbon dioxide, water vapors and nitrogen oxides. | ||
| + | |||
| + | Reduction using [[tin(II) chloride]] in [[hydrochloric acid]] yields [[hydroxylammonium chloride]], but separation from the tin solution is somewhat difficult.<ref>O. F. v. Dumreicher, ''Monatshefte für Chemie'', '''1880''', 1, 724–754 [https://doi.org/10.1007/BF01517102 doi.org/10.1007/BF01517102]</ref> | ||
===Physical=== | ===Physical=== | ||
| Line 118: | Line 120: | ||
===Explosive=== | ===Explosive=== | ||
| − | Ethyl nitrate, like all low-weight nitrate esters is a sensitive explosive, especially to strong impact or exposure to very high temperatures, though less so than [[methyl nitrate]]. It has been claimed to explode during distillation, though the exact reason is not given. Ethyl nitrate has a detonation velocity of 6,010 m/s at a density of 1.11.<ref>https:// | + | Ethyl nitrate, like all low-weight nitrate esters is a sensitive explosive, especially to strong impact or exposure to very high temperatures, though less so than [[methyl nitrate]]. It has been claimed to explode during distillation, though the exact reason is not given. Ethyl nitrate has a detonation velocity of 6,010 m/s at a density of 1.11.<ref>G.D. Kozak, ''Combust Explos Shock Waves'', '''1998''', 34, 581–586, [https://doi.org/10.1007/BF02672682 doi.org/10.1007/BF02672682]</ref> It has an oxygen balance of -61.5%.<ref>Jiping Liu, 2015, ''Liquid Explosives''</ref> |
==Availability== | ==Availability== | ||
| Line 130: | Line 132: | ||
[[Silver chloride]]/[[silver iodide|iodide]] precipitates out of the solution, and the ethyl nitrate solution is filtered and purified. Although it's possible to remove the ethyl nitrate from the resulting solution, concentrating this compounds carries a risk of explosion. | [[Silver chloride]]/[[silver iodide|iodide]] precipitates out of the solution, and the ethyl nitrate solution is filtered and purified. Although it's possible to remove the ethyl nitrate from the resulting solution, concentrating this compounds carries a risk of explosion. | ||
| − | Ethyl nitrate can also be prepared by nitrating [[ethanol]] with | + | Ethyl nitrate can also be prepared by nitrating [[ethanol]] with [[nitric acid]], fuming nitric acid or a mixture of concentrated sulfuric and nitric acids, in the presence of [[urea]].<ref>https://www.prepchem.com/synthesis-of-ethyl-nitrate/</ref><ref>H. Biltz, W. Biltz, ''Laboratory Methods of Inorganic Chemistry'', 1st edition '''1909''', John Wiley and Sons, p. 206, [https://archive.org/details/laboratorymetho00biltgoog/page/n226/mode/1up fulltext here]</ref><ref> B. Picquet-Varrault et al., ''Phys. Chem. Chem. Phys.'', '''2001''', 3, 2595-2606, [https://doi.org/10.1039/B101704G doi.org/10.1039/B101704G]</ref> The urea serves to decompose any nitrous acid present which would present an explosion risk.<ref>W. M. Cumming, ''Systematic Organic Chemistry,'' 3rd edition '''1937''', D. Van Nostrat Company, p. 254, [https://archive.org/details/Cumming1937/page/n273/mode/1up fulltext here]</ref> Further purifying by distillation carries a serious risk of explosion, especially if done at atmospheric pressure. |
Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through [[ethanol]] at −10 °C.<ref>https://pubs.rsc.org/en/content/articlelanding/1954/JR/jr9540003512#!divAbstract</ref> | Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through [[ethanol]] at −10 °C.<ref>https://pubs.rsc.org/en/content/articlelanding/1954/JR/jr9540003512#!divAbstract</ref> | ||
Latest revision as of 10:47, 10 July 2022
| Names | |
|---|---|
| IUPAC name
Ethyl nitrate
| |
| Other names
Nitric acid ethyl ester
Nitric ether | |
| Properties | |
| C2H5NO3 | |
| Molar mass | 91.07 g/mol |
| Appearance | Colorless liquid |
| Odor | Sweet, pleasant |
| Density | 1.1084 g/cm3 (20 °C) |
| Melting point | −102 °C (−152 °F; 171 K) |
| Boiling point | 87.5 °C (189.5 °F; 360.6 K) |
| Slightly soluble | |
| Solubility | Miscible with diethyl ether, ethanol, methanol |
| Vapor pressure | 64.0 mm Hg at 25 °C |
| Thermochemistry | |
| Hazards | |
| Safety data sheet | None |
| Related compounds | |
| Related compounds
|
Methyl nitrate Ethylene glycol dinitrate Propyl nitrate Isopropyl nitrate |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Ethyl nitrate is an organic chemical compound, the ethyl ester of nitric acid. It has the chemical formula C2H5NO3.
Contents
Properties
Chemical
Ethyl nitrate burns in air releasing carbon dioxide, water vapors and nitrogen oxides.
Reduction using tin(II) chloride in hydrochloric acid yields hydroxylammonium chloride, but separation from the tin solution is somewhat difficult.[1]
Physical
Ethyl nitrate is a colorless liquid, with an odor and taste described as sweet, typical of organic nitrate esters.
Explosive
Ethyl nitrate, like all low-weight nitrate esters is a sensitive explosive, especially to strong impact or exposure to very high temperatures, though less so than methyl nitrate. It has been claimed to explode during distillation, though the exact reason is not given. Ethyl nitrate has a detonation velocity of 6,010 m/s at a density of 1.11.[2] It has an oxygen balance of -61.5%.[3]
Availability
Ethyl nitrate, like most organic nitrate esters is not sold by chemical suppliers, due to its hazards, and has to be prepared in situ.
Preparation
Ethyl nitrate has been prepared in high yield by reacting ethyl halide (like ethyl chloride or ethyl iodide) with silver nitrate in a solvent.
- C2H5X + AgNO3 → C2H5NO3 + AgX
Silver chloride/iodide precipitates out of the solution, and the ethyl nitrate solution is filtered and purified. Although it's possible to remove the ethyl nitrate from the resulting solution, concentrating this compounds carries a risk of explosion.
Ethyl nitrate can also be prepared by nitrating ethanol with nitric acid, fuming nitric acid or a mixture of concentrated sulfuric and nitric acids, in the presence of urea.[4][5][6] The urea serves to decompose any nitrous acid present which would present an explosion risk.[7] Further purifying by distillation carries a serious risk of explosion, especially if done at atmospheric pressure.
Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C.[8]
Projects
- Make blasting cap
- Vasodilator
Handling
Safety
Ethyl nitrate in its pure form is sensible to shock and may explode if struck. This property is greatly increased by its volatility. Contact with skin or inhaled, like in the case of nitroglycerin, will lead to severe headaches.
Storage
Do not store ethyl nitrate! Use it as quickly as possible.
Disposal
Small amounts of ethyl nitrate can be detonated in a safe area, or heavily diluted with a flammable solvent, like an alcohol and burned.
For a chemical, safer method, ethyl nitrate should be first diluted in an alcohol, then, very carefully and slowly, a diluted solution of NaOH in alcohol is added dropwise, while keeping the solution cooled at low temperature. This route should not be performed unless the person knows how the reaction will proceed!
References
- ↑ O. F. v. Dumreicher, Monatshefte für Chemie, 1880, 1, 724–754 doi.org/10.1007/BF01517102
- ↑ G.D. Kozak, Combust Explos Shock Waves, 1998, 34, 581–586, doi.org/10.1007/BF02672682
- ↑ Jiping Liu, 2015, Liquid Explosives
- ↑ https://www.prepchem.com/synthesis-of-ethyl-nitrate/
- ↑ H. Biltz, W. Biltz, Laboratory Methods of Inorganic Chemistry, 1st edition 1909, John Wiley and Sons, p. 206, fulltext here
- ↑ B. Picquet-Varrault et al., Phys. Chem. Chem. Phys., 2001, 3, 2595-2606, doi.org/10.1039/B101704G
- ↑ W. M. Cumming, Systematic Organic Chemistry, 3rd edition 1937, D. Van Nostrat Company, p. 254, fulltext here
- ↑ https://pubs.rsc.org/en/content/articlelanding/1954/JR/jr9540003512#!divAbstract
