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Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN.^[1] 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 homemade explosive compound to the amateur experimenter.

Like many nitrate esters, ETN acts as a vasodilator, and was the active ingredient in the original "sustained release" tablets, made under a process patent in the early 1950s, called "nitroglyn". 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/s 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.

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.

2 C₄H₆N₄O₁₂ → 8 CO₂ + 6 H₂O + 4 N₂ + 1 O₂

Whereas PETN decomposes to:

2 C₅H₈N₄O₁₂ → 6 CO₂ + 8 H₂O + 4 N₂ + 4 CO

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 and act as a catalyst from the resulting esterification, driving the reaction.

References

^ Erythritol tetranitrate was first synthesized by British chemist John Stenhouse (1809-1880) in 1849. He extracted the simple sugar erythritol (which he called "erythroglucin") from lichen and then studied its chemistry. See: John Stenhouse (1 January 1849) "Examination of the proximate principles of some of the lichens. Part II," Philosophical Transactions of the Royal Society (London), vol. 139, pages 393-401. Reprinted in German as: John von Stenhouse (1849) "Über die näheren Bestandtheile einige Flechten," Justus Liebigs Annalen der Chemie und Pharmacie, vol. 70, no. 2, pages 218-228. Condensed version (in German): John Stenhouse (12 Sept. 1849) "Über die näheren Bestandtheile einige Flechten," Pharmaceutisches Centralblatt, vol. 20, no. 40, pages 625-628.

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English Journal

NO donors. Part 18: Bioactive metabolites of GTN and PETN--synthesis and vasorelaxant properties.

Lange K1, Koenig A, Roegler C, Seeling A, Lehmann J.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2009 Jun 1;19(11):3141-4. doi: 10.1016/j.bmcl.2008.04.057. Epub 2008 Apr 26.
The vasodilators glyceryl trinitrate (GTN) and pentaerythrityl tetranitrate (PETN) are supposed to be degraded in vivo to the lower nitrates PETriN, PEDN, PEMN, 1,2-GDN, 1,3-GDN, 1-GMN, and 2-GMN. We synthesized these bioactive metabolites as reference compounds for pharmacokinetic studies. The use
PMID 19406636

Nitric oxide modulation of the growth hormone-releasing activity of Hexarelin in young and old dogs.

Rigamonti AE1, Cella SG, Marazzi N, Müller EE.
Metabolism: clinical and experimental.Metabolism.1999 Feb;48(2):176-82.
The growth hormone (GH)-releasing activity of Hexarelin, a potent GH-releasing peptide (GHRP) analog, was evaluated in eight young (aged 1 to 6 years) and five old (10 to 16 years) beagle dogs pretreated with erythrityl tetranitrate, a liposoluble nitric oxide (NO) donor, and/or indomethacin, an inh
PMID 10024078

Pentaerithrityl tetranitrate and its phase I metabolites are potent activators of cellular cyclic GMP accumulation.

Hinz B1, Kuntze U, Schröder H.
Biochemical and biophysical research communications.Biochem Biophys Res Commun.1998 Dec 30;253(3):658-61.
Using pig kidney epithelial cells (LLC-PK1), the present study assesses the cyclic GMP stimulatory effect of pentaerithrityl tetranitrate and its metabolites in comparison to other therapeutically used nitric oxide donors. Pentaerithrityl tetranitrate was found to be the most potent activator of cyc
PMID 9918783

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リンク元	「eritrityl tetranitrate」「四硝酸エリスリチル」

「eritrityl tetranitrate」

Erythritol tetranitrate
Names
	IUPAC name [(2R,3R)-1,3,4-Trinitrooxybutan-2-yl] nitrate
Identifiers
CAS Number	7297-25-8
ChEBI	CHEBI:60072
ChemSpider	4447608
Jmol 3D model	Interactive image
PubChem	5284553
UNII	35X333P19D
	InChI InChI=1S/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+ Key: SNFOERUNNSHUGP-ZXZARUISSA-N ; InChI=1/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+ Key: SNFOERUNNSHUGP-ZXZARUISBH ;
	SMILES C(C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-] ;
Properties
Chemical formula	C4H6N4O12
Molar mass	302.11 g/mol
Melting point	61 °C (142 °F; 334 K)
Boiling point	Decomposes at 160 °C
Explosive data
Shock sensitivity	Medium (2.0 Nm)
Friction sensitivity	Medium
Detonation velocity	8000-8100 m/s
RE factor	1.60
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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四硝酸エリスリチル、四硝酸エリトリチル

関: erythrityl tetranitrate

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英: erythrityl tetranitrate、eritrityl tetranitrate
関: 四硝酸エリトリチル

[1] Erythritol tetranitrate was first synthesized by British chemist John Stenhouse (1809-1880) in 1849. He extracted the simple sugar erythritol (which he called "erythroglucin") from lichen and then studied its chemistry. See: John Stenhouse (1 January 1849) "Examination of the proximate principles of some of the lichens. Part II," Philosophical Transactions of the Royal Society (London), vol. 139, pages 393-401. Reprinted in German as: John von Stenhouse (1849) "Über die näheren Bestandtheile einige Flechten," Justus Liebigs Annalen der Chemie und Pharmacie, vol. 70, no. 2, pages 218-228. Condensed version (in German): John Stenhouse (12 Sept. 1849) "Über die näheren Bestandtheile einige Flechten," Pharmaceutisches Centralblatt, vol. 20, no. 40, pages 625-628.

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erythrityl tetranitrate