Erythritol tetranitrate

Erythritol tetranitrate

Chembox new
ImageFile = Erythritol tetranitrate.png ImageSize = 200px
IUPACName = [("2R,3S")-1,3,4-Trinitrooxybutan-2-yl] nitrate
OtherNames =
Section1 = Chembox Identifiers
CASNo = 7297-25-8
PubChem = 5284553
SMILES = C( [C@H] ( [C@H] (CO [N+] (=O) [O-] )O [N+] (=O) [O-] )O [N+] (=O) [O-] )O [N+] (=O) [O-]

Section2 = Chembox Properties
C = 4 | H = 6 | N = 4 | O = 12
MolarMass = 302.11 g/mol
Appearance =
Density =
MeltingPtC = 61
BoilingPt = Decomposes at 160 °C
Solubility =

Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =

Section6 = Chembox Explosive
ShockSens = Medium (2.0 Nm)
FrictionSens = Medium
ExplosiveV = 8000-8100 m/s
REFactor = 1.60

Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN. It is however thought to be 1/3 more sensitive to friction and impact. ETN is not well known, but in recent years has been used by amateur experimenters to replace PETN in improvised detonation cord or in boosters to initiate larger, less sensitive explosive charges. Due to the availability of erythritol as a natural sweetener and its relative ease of production in relation to PETN, ETN is a favoured home made explosive compound to the amateur experimenter.

Like many nitric esters, ETN acts as a vasodilator. Ingesting ETN or prolonged skin contact can lead to absorption and what is known as a "nitro headache".

Properties

ETN has a relatively high velocity of detonation of 8000-8100 m/sec at a density of 1.6 g/cm3. It is white in color and odorless. ETN is commonly cast into mixtures with other high explosives. It is somewhat sensitive to shock and friction, so care should be taken while handling. ETN dissolves readily in acetone and other ketone solvents though for the purpose of recrystallization, slow cooling of a saturated solution in ethanol from 55 °C gives much better results with purer and better formed crystals.

Much like PETN, ETN is known for having a very long shelf life. Studies that directly observed the crystalline structure saw no signs of decomposition after four years of storage at room temperature.

Oxygen balance

One quality this explosive has, that PETN does not, is a positive oxygen balance. Having a positive oxygen balance means that ETN possesses more than enough oxygen in its structure to fully oxidize all of its carbon and hydrogen upon detonation. This can be seen in the equation below.

:C4H6N4O12 → 4 CO2 + 3 H2O + 2 N2 + ½ O2

Whereas PETN decomposes to:

:C5H8N4O12 → 3 CO2 + 2 CO + 4 H2O + 2 N2

The carbon monoxide (CO) still requires oxygen to complete oxidation to carbon dioxide (CO2).

Thus for every mole of ETN that decomposes, 1/2 free mole of O2 is released. This could be used to oxidize an added metal dust or an oxygen deficient explosive such as TNT or PETN.

Manufacture

Like other nitrated polyols, ETN is made by nitrating erythritol through the mixing of concentrated sulfuric acid and a nitrate salt. Ammonium nitrate is commonly used for this type of reaction. The erythritol is added to the mixture to begin its nitration. Much better yields can be obtained by using concentrated nitric acid in place of the nitrate salt, in which case the sulfuric acid is used simply to absorb water from the resulting esterification, driving the reaction.

See also

* Mannitol hexanitrate
* Xylitol pentanitrate
* Erythritol tetranitrate
* Nitroglycerine, most properly Glycerol trinitrate
* Ethylene glycol dinitrate
* Nitromethane

References


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать курсовую

Look at other dictionaries:

  • erythritol — ə̇ˈrithrəˌtȯl, ōl noun ( s) Etymology: International Scientific Vocabulary erythr + itol : a sweet crystalline tetrahydroxy alcohol HOCH2(CHOH)2CH2OH obtained as the optically inactive meso form from lichens, algae, and yeasts or made by… …   Useful english dictionary

  • erythrityl tetranitrate — A vasodilator used in angina pectoris and hypertension. SYN: erythrol tetranitrate, tetranitrol. * * * eryth·ri·tyl tet·ra·ni·trate i rith rə .til .te trə nī .trāt n a salt of erythritol with nitric acid C4H10N4O12 that is used esp. as a… …   Medical dictionary

  • Mannitol hexanitrate — IUPAC name (2R,3R,4R,5R) Hexane 1,2,3,4,5,6 hexol 1,2,3,4,5,6 hexanitrate …   Wikipedia

  • Nitroglycerin — This article is about the chemical properties of nitroglycerin and its use as an explosive. For medical and pharmacological applications, see glyceryl trinitrate (pharmacology). Nitroglycerin …   Wikipedia

  • Ethylene glycol dinitrate — IUPAC name 1,2 dinitroxyethane …   Wikipedia

  • ETN — or ETN may refer to: * Erythritol tetranitrate, an explosive chemical compound * Exchange traded note, a synthetic financial derivative * Erie Times News, the daily newspaper in Erie, Pennsylvania …   Wikipedia

  • Xylitol pentanitrate — Chembox new ImageFile = Xylitol pentanitrate.png ImageSize = 200px IUPACName = 1,2,3,4,5 Pentakis nitrooxy pentane OtherNames = Section1 = Chembox Identifiers CASNo = 147 16 0 PubChem = SMILES = Section2 = Chembox Properties Formula = C5H7N5O15… …   Wikipedia

  • Facteur d'efficacité relative — Le facteur d efficacité relative est une mesure de puissance d un explosif destiné à des démolitions militaires. Il est utilisé pour comparer l efficacité massique d un explosif par rapport au TNT. Cela permet aux ingénieurs de substituer un… …   Wikipédia en Français

  • erythrol — SYN: erythritol. e. tetranitrate SYN: erythrityl tetranitrate. * * * er·y·throl er ə .thrȯl, i rith .rȯl, .rōl n 1) a liquid unsaturated dihydroxy alcohol C4H8O2 formed by decomposition of erythritol 2) ERYTHRITOL * * * er·yth·rol (erґith rol)… …   Medical dictionary

  • erythrol — ˈerəˌthrȯl, ə̇ˈriˌth , ōl noun ( s) Etymology: International Scientific Vocabulary erythr + ol 1. : a liquid unsaturated dihydroxy alcohol CH2 = CHCHOHCH2OH formed by decomposition of erythritol 2. : erythritol used especially in pharmacy …   Useful english dictionary

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”