1,2,4-Butanetriol trinitrate

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477199687

| Name = 1,2,4-Butanetriol trinitrate

| ImageFile = 1,2,4-Butanetriol trinitrate.svg

| ImageFile1 = 1,2,4-Butanetriol-trinitrate-3D-balls.png

| ImageName1 = C=black, H=white, O=red, N=blue

| ImageAlt1 = 1,2,4-Butanetriol trinitrate molecule

| ImageSize1 = 220px

| ImageName =

| PIN = Butane-1,2,4-triyl trinitrate

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 455532

| PubChem = 522216

| EINECS = 229-697-1

| InChI = 1/C4H7N3O9/c8-5(9)14-2-1-4(16-7(12)13)3-15-6(10)11/h4H,1-3H2

| InChIKey = RDLIBIDNLZPAQD-UHFFFAOYAH

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H7N3O9/c8-5(9)14-2-1-4(16-7(12)13)3-15-6(10)11/h4H,1-3H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RDLIBIDNLZPAQD-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 6659-60-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ZV2U79W7V4

| SMILES = O=[N+]([O-])OC(CCO[N+]([O-])=O)CO[N+](=O)[O-]

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| Section2 = {{Chembox Properties

| Formula = C{{sub|4}}H{{sub|7}}N{{sub|3}}O{{sub|9}}

| MolarMass = 241.11 g/mol

| Density = 1.52 g/cm3

| MeltingPt =25 °C

| BoilingPt = 230 °C (446 °F; 503 K) (explosion temperature)

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| Section7 = {{Chembox Hazards

| GHSPictograms = {{GHS01}}{{GHS06}}{{GHS08}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|200|300|310|330|373|411}}

| PPhrases = {{P-phrases|201|202|260|262|264|270|271|273|280|281|284|301+310|302+350|304+340|310|314|320|321|322|330|361|363|372|373|380|391|401|403+233|405|501}}

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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.{{Cite book|url=https://www.amazon.com/1-2-4-Butanetriol-Analysis-Synthesis/dp/B00BVD8Q06|title=1,2,4-Butanetriol: Analysis and Synthesis|last=Pisacane|first=Frank J.|date=1982|publisher=PN}}

BTTN is used as a propellant in virtually all single-stage missiles used by the United States, including the Hellfire.{{Cite news|url=http://news.bbc.co.uk/2/hi/science/nature/3450853.stm|title=Bacteria help make missile fuel|date=2004-02-02|access-date=2018-11-02}} It is less volatile, less sensitive to shock, and more thermally stable than nitroglycerine,{{Cite book|url=https://books.google.com/books?id=_fmGDgAAQBAJ|title=The Chemistry and Technology of Solid Rocket Propellants (A Treatise on Solid Propellants)|last=Varghese|first=T. L.|last2=Krishnamurthy|first2=V. N.|date=2017-01-03|publisher=Allied Publishers|isbn=978-93-85926-33-4|pages=187}} for which it is a promising replacement.{{Cite journal|first=D.|last=Bhowmik|first2=V.S.|last2=Sadavarte|last3=Pande|first3=S.M.|last4=Saraswat|first4=B.S.|date=2015|title=An Energetic Binder for the Formulation of Advanced Solid Rocket Propellants|url=http://yadda.icm.edu.pl/baztech/element/bwmeta1.element.baztech-98bc795f-3fcd-4a08-9855-d57a0cdf95c3|journal=Central European Journal of Energetic Materials|volume=12|issue=1|pages=147}}

BTTN as a propellant is often used in a mixture with nitroglycerin. The mixture can be made by co-nitration of butanetriol and glycerol.{{Cite web|last=Farncomb|first=Robert E.|last2=Carr|first2=Walter A.|date=1987-07-06|title=Patent application: Co-Nitration of 1,2,4-Butanetriol and Glycerin |url=http://www.dtic.mil/docs/citations/ADD013053|archive-url=https://web.archive.org/web/20220601060916/http://www.dtic.mil/docs/citations/ADD013053|url-status=dead|archive-date=June 1, 2022}} BTTN is also used as a plasticizer in some nitrocellulose-based propellants.{{Cite book|url=https://books.google.com/books?id=uKihDQAAQBAJ|title=Rocket Propulsion Elements|last=Sutton|first=George P.|last2=Biblarz|first2=Oscar|date=2016-11-30|publisher=John Wiley & Sons|isbn=978-1-118-75391-0}}

BTTN is manufactured by nitration of 1,2,4-butanetriol.{{Cite journal|last=Gouranlou|first=Farideh|last2=Kohsary|first2=Iraj|date=2010-06-01|title=Synthesis and Characterization of 1,2,4-Butanetrioltrinitrate|url=https://www.researchgate.net/publication/287002330|journal=Asian Journal of Chemistry|volume=22|pages=4221–4228}} Biotechnological manufacture of butanetriol is under intensive research.{{Cite journal|last=Cao|first=Yujin|last2=Niu|first2=Wei|last3=Guo|first3=Jiantao|last4=Xian|first4=Mo|last5=Liu|first5=Huizhou|date=2015-12-16|title=Biotechnological production of 1,2,4-butanetriol: An efficient process to synthesize energetic material precursor from renewable biomass|journal=Scientific Reports|volume=5|issue=1|pages=18149|doi=10.1038/srep18149|pmid=26670289|issn=2045-2322|pmc=4680960|bibcode=2015NatSR...518149C}}