Dunnite: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 439264983

| ImageFile =Ammoniumpicrate.png

| ImageSize =150px

| IUPACName =Ammonium 2,4,6-trinitrophenolate

| OtherNames =Ammonium picrate; Picratol; 2,4,6-Trinitrophenol ammonium salt; Ammonium picronitrate; Explosive D

| CASNo_Ref = {{cascite|correct|??}}

| CASNo =131-74-8

| EINECS = 205-038-3

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

| UNII = 4N99515C3Z

| PubChem =8577

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8259

| InChI = 1/C6H3N3O7.H3N/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16;/h1-2,10H;1H3

| InChIKey = PADMMUFPGNGRGI-UHFFFAOYAZ

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C6H3N3O7.H3N/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16;/h1-2,10H;1H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = PADMMUFPGNGRGI-UHFFFAOYSA-N

| SMILES =C1=C(C=C(C(=C1[N+](=O)[O-])[O-])[N+](=O)[O-])[N+](=O)[O-].[NH4+]

| C=6 | H=6 | N=4 | O=7

| Appearance =

| Density =1.719 g/cm³<ref name="GESTIS">{{GESTIS|ZVG=570068|CAS=131-74-8|Name=Ammoniumpikrat|Date=24. Nov. 2007}}</ref>

| MeltingPtC = 265

| MeltingPt_ref = <ref name="GESTIS"/>

| BoilingPt =

| Solubility =10&nbsp;g/L (20&nbsp;°C)

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHSPictograms = {{GHS01}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|201|315|317|319}}

| PPhrases = {{P-phrases|210|230|240|250|261|264|272|280|302+352|305+351+338|321|332+313|333+313|337+313|362|363|370+380|372|373|401|501}}

'''Dunnite''', also known as '''Explosive D''' or systematically as '''ammonium picrate''', is an [[explosive]] developed in 1906 by US Army Major Beverly W. Dunn, who later served as chief inspector of the Bureau of Transportation Explosives.<ref>{{citation |author=War Records Committee of the Alumni Association |date=1920 |title=Technology's War Record: An Interpretation of the Contribution Made by the Massachusetts Institute of Technology, Its Staff, Its Former Students and Its Undergraduates to the Cause of the United States and the Allied Powers in the Great War, 1914–1919 |location=Cambridge, MA |publisher=Massachusetts Institute of Technology |page=364}}</ref><ref>[https://timesmachine.nytimes.com/timesmachine/1907/08/18/104992996.pdf "Dunnite Smashes Strongest Armor"], ''[[The New York Times]]'', August 18, 1907</ref> Ammonium picrate is a [[salt (chemistry)|salt]] formed by reacting [[picric acid]] and [[ammonia]]. It is chemically related to the more stable explosive [[trinitrotoluene]] (TNT).

== History ==

Ammonium picrate was proposed for use as a component in gunpowder by Brugère and Abel as early as 1869: the former proposed to mix 54% of it with 46% of saltpetre while the latter, 60% with 40%.<ref>{{Cite book |last=Guttmann |first=Oscar |url=https://books.google.com/books?id=ZMcJAAAAIAAJ&pg=PA160 |title=The Manufacture of Explosives: A Theoretical and Practical Treatise on the History, the Physical and Chemical Properties, and the Manufacture of Explosives |date=1895 |publisher=Whittaker and Company |language=en}}</ref> Their compositions gave less smoke and were more energetic than black powder but neither was adopted by any military, even though in the 1890s "semi-smokeless" powder compositions featuring ammonium picrates were sold commercially in the US.<ref name=":0">{{Cite book |last1=Gelder |first1=Arthur Pine Van |url=https://books.google.com/books?id=7SUaAQAAMAAJ |title=History of the Explosives Industry in America |last2=Schlatter |first2=Hugo |date=1927 |publisher=Columbia University Press |isbn=978-0-231-91436-9 |language=en}}</ref> It also was a minor component of the Peyton powder made by the [[California Powder Works]] which was procured by the US military in the same period.<ref name=":0" />

It was the first explosive used in an aerial bombing operation in military history, performed by Italian pilots in [[Libya]] in 1911.<ref>[https://piste.blogspot.com/2011/03/ultime-notizie-bombardiamo-la-libia.html], [[La Stampa]], November 2, 1911</ref>

It was used extensively by the [[United States Navy]] during [[World War I]].<ref>[https://www.firstworldwar.com/atoz/dunnite.htm Dunnite], Firstworldwar.com</ref>

Though Dunnite was generally considered an insensitive substance, by 1911 the [[United States Army]] had abandoned its use in favor of other alternatives.<ref>[https:https://timesmachine.nytimes.com/timesmachine/1911/08/08/104873365.pdf Ridicule Spy Story: Army Abandoned the Use of Dunnite Years Ago, Officers Say], ''[[The New York Times]]'', August 8, 1911</ref> The [[United States Navy|Navy]], however, used it in [[armor-piercing shot and shell|armor-piercing artillery shells]] and projectiles, and in coastal defense.

By the end of WWI a pound of ammonium picrate cost US government 64 cents, while TNT cost 26.5 c/lb, ammonium nitrate used in [[amatol]] only 17.5 c/'b and black powder about 25 c/lb.<ref>{{Cite book |last=Department |first=United States War |url=https://books.google.com/books?id=l4wsAAAAIAAJ&pg=PA114 |title=America's Munitions 1917-1918: Report of Benedict Crowell, the Assistant Secretary of War, Director of Munitions |date=1919 |publisher=U.S. Government Printing Office |language=en}}</ref>

Dunnite typically did not detonate on striking heavy armor. Rather, the encasing shell would penetrate the armor, after which the charge would be triggered by a base [[fuze]].

During [[WWII]], it was gradually replaced by [[RDX]]-based Composition A-3.<ref>{{Cite book |last=Rowland |first=Buford |url=https://books.google.com/books?id=EqNZ5hjPOVMC&pg=PA208 |title=U.S. Navy Bureau of Ordnance in World War II |date=1953 |publisher=Bureau of Ordnance, Department of the Navy |language=en}}</ref>

In 2008 caches of discarded Dunnite in remote locations were mistaken for rusty rocks at [[Cape Porcupine, Labrador|Cape Porcupine]], [[Newfoundland and Labrador]], Canada.<ref>{{cite news |url=https:https://www.theglobeandmail.com/news/national/family-makes-explosive-discovery-on-labrador-shore/article955359/1 |title=Family makes explosive discovery on Labrador shore |first=Oliver |last=Moore |work=The Globe and Mail |date=2008-09-11 |archive-url=https://web.archive.org/web/20170109024149/https://www.theglobeandmail.com/news/national/family-makes-explosive-discovery-on-labrador-shore/article955359/1/ |archive-date=2017-01-09}}</ref><ref>{{cite news | url=https://www.cbc.ca/news/canada/newfoundland-labrador/beachcombing-labrador-family-carries-home-wartime-explosive-1.757030 | title=Beachcombing Labrador family carries home wartime explosive | publisher=[[Canadian Broadcasting Corporation]] | date=2008-09-10 | accessdate=2017-01-07}}</ref>

Dunnite can be used as a precursor to the highly stable explosive [[TATB]] (1,3,5-triamino-2,4,6-trinitrobenzene), by first dehydrating it to form [[picramide]] (attaching the ammonia as an amine group instead of an ion) and then further aminating it, using [[1,1,1-trimethylhydrazinium iodide]] (TMHI) made from [[unsymmetrical dimethylhydrazine]] rocket fuel and [[methyl iodide]]. Thus, surplus materials that would have to be destroyed when no longer needed are converted into a high value explosive.<ref>{{cite tech report|last1=Mitchell |first1=Alexander R.|first2=P. F. |last2=Pagoria|first3=R D. |last3=Schmidt|title=Conversion of the Rocket Propellant UDMH to a Reagent Useful in Vicarious Nucleophilic Substitution Reactions|url=https://digital.library.unt.edu/ark:/67531/metadc670413/m2/1/high_res_d/226422.pdf|publisher=Lawrence Livermore National Laboratory|number=UCRL-JC-122489|date=10 November 1995|s2cid=54794595}}</ref><ref>{{cite journal|doi=10.1016/S0040-6031(01)00806-1 |title=Advances in the chemical conversion of surplus energetic materials to higher value products |year=2002 |last1=Mitchell |first1=Alexander R. |last2=Coburn |first2=Michael D. |last3=Schmidt |first3=Robert D. |last4=Pagoria |first4=Philip F. |last5=Lee |first5=Gregory S. |journal=Thermochimica Acta |volume=384 |issue=1–2 |pages=205–217 |bibcode=2002TcAc..384..205M }}</ref>

{{Reflist|30em}}

{{Ammonium salts}}

[[Category:Ammonium compounds]]

[[Category:Naval artillery]]