1,2,4-Butanetriol trinitrate

1,2,4-Butanetriol trinitrate
Identifiers
CAS Number	6659-60-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	455532 ;
ECHA InfoCard	100.026.998
EC Number	229-697-1;
PubChem CID	522216;
CompTox Dashboard (EPA)	DTXSID90863924 ;
	InChI InChI=1S/C4H7N3O9/c8-5(9)14-2-1-4(16-7(12)13)3-15-6(10)11/h4H,1-3H2 Key: RDLIBIDNLZPAQD-UHFFFAOYSA-N ; 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;
	SMILES O=[N+]([O-])OC(CCO[N+]([O-])=O)CO[N+](=O)[O-];
Properties
Chemical formula	C4H7N3O9
Molar mass	241.11 g/mol
Melting point	250k
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H200, H300, H310, H330, H373, H411
GHS precautionary statements	P201, P202, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+310, P302+350, P304+340, P310, P314, P320, P321, P322, P330, P361, P363, P372, P373, P380
	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

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]

References

Pisacane, Frank J. (1982). 1,2,4-Butanetriol: Analysis and Synthesis. PN.
"Bacteria help make missile fuel". 2004-02-02. Retrieved 2018-11-02.
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.
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.
Farncomb, Robert E.; Carr, Walter A. (1987-07-06). "Co-Nitration of 1,2,4-Butanetriol and Glycerin". Cite journal requires |journal= (help)
Sutton, George P.; Biblarz, Oscar (2016-11-30). Rocket Propulsion Elements. John Wiley & Sons. ISBN 978-1-118-75391-0.
Gouranlou, Farideh; Kohsary, Iraj (2010-06-01). "Synthesis and Characterization of 1,2,4-Butanetrioltrinitrate". Asian Journal of Chemistry. 22: 4221–4228.
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.

External links

WebBook page for 1,2,4-Butanetriol, trinitrate

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[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.

[:0-3] 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). "Co-Nitration of 1,2,4-Butanetriol and Glycerin". Cite journal requires |journal= (help)

[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.