1,2,4-Butanetriol trinitrate

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1,2,4-Butanetriol trinitrate
1,2,4-Butanetriol trinitrate.svg
1,2,4-Butanetriol-trinitrate-3D-balls.png
Names
Preferred IUPAC name
Butane-1,2,4-triyl trinitrate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.026.998 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 229-697-1
PubChem CID
UNII
  • InChI=1S/C4H7N3O9/c8-5(9)14-2-1-4(16-7(12)13)3-15-6(10)11/h4H,1-3H2 Yes check.svgY
    Key: RDLIBIDNLZPAQD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H7N3O9/c8-5(9)14-2-1-4(16-7(12)13)3-15-6(10)11/h4H,1-3H2
    Key: RDLIBIDNLZPAQD-UHFFFAOYAH
  • O=[N+]([O-])OC(CCO[N+]([O-])=O)CO[N+](=O)[O-]
Properties
C4H7N3O9
Molar mass 241.11 g/mol
Density 1.52 g/cm3
Melting point 25 °C
Boiling point 230 °C (446 °F; 503 K) (explosion temperature)
Hazards
GHS labelling:
GHS-pictogram-explos.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H200, H300, H310, H330, H373, H411
P201, P202, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P372, P373, P380, P391, P401, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,2,4-Butanetriol trinitrate (BTTN), also called butanetriol trinitrate, is an important military propellant. It is a colorless to brown explosive liquid. [1]

BTTN is used as a propellant in virtually all single-stage missiles used by the United States, including the Hellfire. [2] It is less volatile, less sensitive to shock, and more thermally stable than nitroglycerine, [3] for which it is a promising replacement. [4]

BTTN as a propellant is often used in a mixture with nitroglycerin. [3] The mixture can be made by co-nitration of butanetriol and glycerol. [5] BTTN is also used as a plasticizer in some nitrocellulose-based propellants. [6]

BTTN is manufactured by nitration of 1,2,4-butanetriol. [7] Biotechnological manufacture of butanetriol is under intensive research. [8]

Related Research Articles

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Explosive Substance that can explode

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Nitroglycerin Chemical compound

Nitroglycerin (NG), also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), Nobel Oil, or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Invented in 1847 by Ascanio Sobrero, nitroglycerin has been used ever since as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. Since the 1880s, it has been used by the military as an active ingredient and gelatinizer for nitrocellulose in some solid propellants such as cordite and ballistite. It is a major component in double-based smokeless propellants used by reloaders. Combined with nitrocellulose, hundreds of powder combinations are used by rifle, pistol, and shotgun reloaders.

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Epichlorohydrin Chemical compound

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1,2,4-Butanetriol Chemical compound

1,2,4-Butanetriol is a clear or slightly yellow, odorless, hygroscopic, flammable, viscous liquid. It is an alcohol with three hydrophilic alcoholic hydroxyl groups. It is similar to glycerol and erythritol. It is chiral, with two possible enantiomers.

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References

  1. Pisacane, Frank J. (1982). 1,2,4-Butanetriol: Analysis and Synthesis. PN.
  2. "Bacteria help make missile fuel". 2004-02-02. Retrieved 2018-11-02.
  3. 1 2 Varghese, T. L.; Krishnamurthy, V. N. (2017-01-03). The Chemistry and Technology of Solid Rocket Propellants (A Treatise on Solid Propellants). Allied Publishers. p. 187. ISBN   978-93-85926-33-4.
  4. Bhowmik, D.; Sadavarte, V.S.; Pande, S.M.; Saraswat, B.S. (2015). "An Energetic Binder for the Formulation of Advanced Solid Rocket Propellants". Central European Journal of Energetic Materials. 12 (1): 147.
  5. Farncomb, Robert E.; Carr, Walter A. (1987-07-06). "Patent application: Co-Nitration of 1,2,4-Butanetriol and Glycerin". Archived from the original on June 1, 2022.
  6. Sutton, George P.; Biblarz, Oscar (2016-11-30). Rocket Propulsion Elements. John Wiley & Sons. ISBN   978-1-118-75391-0.
  7. Gouranlou, Farideh; Kohsary, Iraj (2010-06-01). "Synthesis and Characterization of 1,2,4-Butanetrioltrinitrate". Asian Journal of Chemistry. 22: 4221–4228.
  8. Cao, Yujin; Niu, Wei; Guo, Jiantao; Xian, Mo; Liu, Huizhou (2015-12-16). "Biotechnological production of 1,2,4-butanetriol: An efficient process to synthesize energetic material precursor from renewable biomass". Scientific Reports. 5 (1): 18149. Bibcode:2015NatSR...518149C. doi:10.1038/srep18149. ISSN   2045-2322. PMC   4680960 . PMID   26670289.