Acetone peroxide: Difference between revisions

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The product made by using hydrochloric acid is regarded as more stable than the one made using sulfuric acid. It is known that traces of sulfuric acid trapped inside the formed acetone peroxide crystals lead to instability. In fact, the trapped sulfuric acid can induce detonation at temperatures as low as {{cvt|50|°C}}. This is the most likely mechanism behind accidental explosions of acetone peroxide that occur during drying on heated surfaces.<ref>{{Cite journal|last1=Matyas|first1=Robert|last2=Pachman|first2=Jiri| name-list-style = vanc |date=2007-07-01|title=Thermal stability of triacetone triperoxide|url=https://www.researchgate.net/publication/279704800|journal=Science and Technology of Energetic Materials|volume=68|pages=111–116}}</ref>

 

Organic peroxides in general are sensitive, dangerous explosives, and all forms of acetone peroxide are sensitive to [[initiation (chemistry)|initiation]].{{citation needed|date=March 2016}} TATP decomposes explosively; examination of the explosive [[chemical decomposition|decomposition]] of TATP at the very edge of detonation front predicts "formation of [[acetone]] and [[ozone]] as the main decomposition products and not the intuitively expected oxidation products."<ref name=pmid15669854>{{cite journal |doi=10.1021/ja0464903 |pmid=15669854 |title=Decomposition of Triacetone Triperoxide is an Entropic Explosion |journal=Journal of the American Chemical Society |volume=127 |issue=4 |pages=1146–1159 |year=2005 |last1=Dubnikova |first1=Faina |last2=Kosloff |first2=Ronnie |last3=Almog |first3=Joseph |last4=Zeiri |first4=Yehuda |last5=Boese |first5=Roland |last6=Itzhaky |first6=Harel |last7=Alt |first7=Aaron |last8=Keinan |first8=Ehud }}</ref> Very little heat is created by the explosive decomposition of TATP at the very edge of the detonation front; the foregoing computational analysis suggests that TATP decomposition is an [[entropic explosion]].<ref name=pmid15669854/> However, this hypothesis has been challenged as not conforming to actual measurements.<ref name="j.tca.2014">{{cite journal | title = Thermochemistry of cyclic acetone peroxides | vauthors = Sinditskii VP, Koltsov VI, Egorshev, VY, Patrikeev DI, Dorofeeva OV | journal = Thermochimica Acta | year = 2014 | volume = 585 | pages = 10–15 | doi = 10.1016/j.tca.2014.03.046}}</ref> The claim of entropic explosion has been tied to the events just behind the detonation front. The authors of the 2004 Dubnikova et al. study confirm that a final redox reaction (combustion) of ozone, oxygen and reactive species into water, various oxides and hydrocarbons takes place within about 180{{nbs}}[[Picosecond|ps]] after the initial reaction - within about a micron of the detonation wave. Detonating crystals of TATP ultimately reach temperature of {{cvt|2300|K|C F}} and pressure of 80 kbar.<ref>{{cite journal | doi = 10.1021/ja052067y| pmid = 16076213| title = Atomistic-Scale Simulations of the Initial Chemical Events in the Thermal Initiation of Triacetonetriperoxide| journal = Journal of the American Chemical Society| volume = 127| issue = 31| pages = 11053–62| year = 2005| last1 = Van Duin| first1 = Adri C. T| last2 = Zeiri| first2 = Yehuda| last3 = Dubnikova| first3 = Faina| last4 = Kosloff| first4 = Ronnie| last5 = Goddard| first5 = William A | name-list-style = vanc }}</ref> The final energy of detonation is about 2800 kJ/kg (measured in helium), enough to briefly raise the temperature of gaseous products to {{cvt|2000|°C}}. Volume of gases at [[Standard temperature and pressure|STP]] is 855 L/kg for TATP and 713 L/kg for DADP (measured in helium).<ref name="j.tca.2014"/>

 

The tetrameric form of acetone peroxide, prepared under neutral conditions using a [[tin(IV) chloride|tin]] catalyst in the presence of a [[chelator]] or general inhibitor of [[Radical (chemistry)|radical chemistry]], is reported to be more chemically stable, although still a very dangerous [[primary explosive]].<ref name=jiang/> Its synthesis has been disputed.<ref name="Pachman, J. 2010"/>

Both TATP and DADP are prone to loss of mass via [[Sublimation (phase transition)|sublimation]]. DADP has lower [[Molecular mass|molecular weight]] and higher [[vapor pressure]]. This means that DADP is more prone to sublimation than TATP. This can lead to dangerous crystal growth when the vapors deposit if the crystals have been stored in a container with a threaded lid. This process of repeated sublimation and deposition also results in a change in crystal size via [[Ostwald ripening]].

 

 

Acetone peroxide is soluble in toluene, chloroform, acetone, dichloromethane and methanol.<ref>{{cite journal|last1 = Kende |first1 =Anikó |first2=Ferenc|last2= Lebics|first3= Zsuzsanna |last3 =Eke|first4 = Kornél|last4 = Torkos|journal = Microchimica Acta|volume = 163|pages = 335–338 |year =2008|title = Trace level triacetone-triperoxide identification with SPME–GC-MS in model systems|issue =3–4 |doi =10.1007/s00604-008-0001-x|s2cid =97978057 }}</ref> Recrystalization of primary explosives may yield large crystals that detonate spontaneously due to internal strain.<ref>Primary Explosives - page 278, {{ISBN|9783642284359}}</ref>

 

== Industrial uses ==

TATP has been used in bomb and suicide attacks and in improvised explosive devices, including the [[7 July 2005 London bombings|London bombings on 7 July 2005]], where four suicide bombers killed 52 people and injured more than 700.<ref>[https://www.theguardian.com/uk/2006/may/07/theobserver.uknews "The real story of 7/7"], ''[[The Observer]]'', 7 May 2006</ref><ref>[http://www.redorbit.com/news/general/197067/london_bombers_used_everyday_materialsus_police/index.html][[London]]<span> bombers used everyday materials—U.S. police</span>, Reuters, 4 August 2005</ref><ref>{{cite web|last=Naughton |first=Philippe |name-list-style=vanc |date=2005-07-15 |url=http://www.timesonline.co.uk/article/0,,22989-1695442,00.html |title=TATP is suicide bombers' weapon of choice |website=The Times (UK) |url-status=dead |archive-url=https://web.archive.org/web/20080210235200/http://www.timesonline.co.uk/article/0%2C%2C22989-1695442%2C00.html |archive-date=10 February 2008 }}</ref><ref name="Vince_2005">{{cite web | url = https://www.newscientist.com/article/dn7682-explosives-linked-to-london-bombings-identified/ | title = Explosives linked to London bombings identified | last = Vince | first = Gaia | name-list-style = vanc | date = 15 July 2005 | website = New Scientist }}</ref> It was one of the explosives used by the "shoe bomber" [[Richard Reid]]<ref name="CNN 12-28-01">{{cite news|url=http://edition.cnn.com/2001/US/12/28/inv.reid/|title=Judge denies bail to accused shoe bomber|date=28 December 2001|publisher=CNN}}</ref><ref name=det>{{cite web|url=http://officialconfusion.com/77/explosives/type/220705janestatp.html |title=Terrorist Use of TATP Explosive |website=officialconfusion.com |date=2005-07-25 }}</ref><ref name="Vince_2005" /> in his [[2001 failed shoe bomb attempt]] and was used by the suicide bombers in the [[November 2015 Paris attacks]],<ref name="nyt-isis">{{cite news | first1 = Rukmini | last1 = Callimachi | first2 = Alissa J. | last2 = Rubin | first3 = Laure | last3 = Fourquet | name-list-style = vanc | url = https://www.nytimes.com/2016/03/20/world/europe/a-view-of-isiss-evolution-in-new-details-of-paris-attacks.html | title = A View of ISIS's Evolution in New Details of Paris Attacks | date = 2016-03-19 | newspaper = The New York Times }}</ref> [[2016 Brussels bombings]],<ref name="url_LeVif.be">{{cite web | url = http://www.levif.be/actualite/belgique/la-mere-de-satan-ou-tatp-l-explosif-prefere-de-l-ei/article-normal-482065.html | title = 'La mère de Satan' ou TATP, l'explosif préféré de l'EI | trans-title = 'Mother of Satan' or TATP, the preferred explosive for IEDs| language = fr | website = LeVif.be Express | date = 2016-03-23 }}</ref> [[Manchester Arena bombing]], [[June 2017 Brussels attack]],<ref name="GuardianManTATP">{{Cite news|url=https://www.theguardian.com/uk-news/2017/may/25/manchester-bomb-same-explosive-paris-brussels-attacks-mike-mccaul | title=Manchester bomb used same explosive as Paris and Brussels attacks, says US lawmaker|last=Doherty|first=Ben | name-list-style = vanc |date=25 May 2017|work=The Guardian|access-date=16 September 2017|language=en-GB}}</ref> [[Parsons Green bombing]],<ref name="DeardenWarn">{{cite news|last1=Dearden|first1=Lizzie|title=London attack: Parsons Green bombers 'still out there' more than 24 hours after Tube blast, officials warn|url=https://www.independent.co.uk/news/uk/home-news/london-attack-parsons-green-bombing-tube-underground-isis-latest-suspects-still-out-there-manhunt-a7949951.html |archive-url=https://web.archive.org/web/20170917063929/http://www.independent.co.uk/news/uk/home-news/london-attack-parsons-green-bombing-tube-underground-isis-latest-suspects-still-out-there-manhunt-a7949951.html |archive-date=2017-09-17 |url-access=limited |url-status=live|access-date=5 November 2017|work=The Independent|date=16 September 2017}}</ref> the [[Surabaya bombings]],<ref>{{cite news|title='Mother of Satan' explosives used in Surabaya church bombings: Police|url=http://www.thejakartapost.com/news/2018/05/14/mother-of-satan-explosives-used-in-surabaya-church-bombings-police.html|access-date=15 May 2018|work=The Jakarta Post|date=14 May 2018}}</ref> and the [[2019 Sri Lanka Easter bombings]].<ref>{{Cite web|url=https://www.asiatimes.com/2019/04/article/mother-of-satan-explosive-used-in-sri-lanka-bombings/|title=Asia Times {{!}} 'Mother of Satan' explosive used in Sri Lanka bombings {{!}} Article |website=Asia Times|date=24 April 2019|language=en|access-date=2019-04-24}}</ref><ref>[https://www.newsfirst.lk/2019/04/23/tatp-explosive-used-in-easter-attacks-former-dig-nimal-lewke/ TATP explosive used in Easter attacks – Former DIG Nimal Lewke] News First (Sri Lanka), Retrieved on 23 April 2019.</ref> [[Hong Kong Police Force|Hong Kong police]] claim to have found {{cvt|2|kg}} of TATP among weapons and protest materials in July 2019, when mass protests were taking place against a proposed law [[2019–20 Hong Kong protests|allowing extradition to mainland China]].<ref>{{cite web |url=https://www.bbc.co.uk/news/world-asia-china-49055785 |title=Hong Kong protests: Police probe link of huge explosives haul |publisher=BBC News |author=<!--not stated--> |date= 20 July 2019}}</ref>

 

 

TATP is attractive to terrorists because it is easily prepared from readily available retail ingredients, such as hair bleach and nail polish remover.<ref name="nyt-isis" /> It was also able to evade detection because it is one of the few high explosives that do not contain [[nitrogen]],<ref name="mother of satan" /> and could therefore pass undetected through standard [[explosive detection]] scanners, which were hitherto designed to detect nitrogenous explosives.<ref>{{cite web|title=Feds are all wet on airport security |work=Star-Ledger |location=Newark, New Jersey |date=2006-08-24 |url=http://results.factiva.com/index/index.aspx?ref=NSL0000020060824e28o0001y |quote=At the moment, Watts said, the screening devices are set to detect nitrogen-based explosives, a category that doesn't include TATP |access-date=11 September 2009 }}{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> By 2016, explosives detectors had been modified to be able to detect TATP, and new types were developed.<ref>{{cite news |last1=Jacoby |first1=Mitch |title=Explosive used in Brussels isn't hard to detect |url=https://cen.acs.org/articles/94/web/2016/03/Explosive-used-Brussels-isnt-hard.html|access-date=28 January 2018|work=Chemical & Engineering News|date=29 March 2016}}</ref><ref name=satan/>