Изворни код странице Aceton peroksid

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|  Name = Aceton peroksid
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|  IUPACName = [[Dimethyldioxirane|3,3-Dimethyl-1,2-dioxacyclopropane]] ''(monomer)''<br />3,3,6,6-Tetramethyl-1,2,4,5-tetraoxane ''(dimer)''<br />3,3,6,6,9,9-Hexamethyl-<wbr />1,2,4,5,7,8-hexaoxacyclononane ''(trimer)''<br />3,3,6,6,9,9,12,12-Octamethyl-<wbr />1,2,4,5,7,8,10,11-octaoxacyclododecane ''(tetramer)''
|  IUPACName_hidden = yes
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|  OtherNames = Triaceton triperoksid<br />Peroksiaceton<br />Majka Satane
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|  Abbreviations = 
|  CASNo = 17088-37-8
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|  SMILES = CC1(C)OOC(C)(C)OOC(C)(C)OO1
|  SMILES1_Comment = dimer
|  SMILES2 = CC1(C)OOC(C)(C)OOC(C)(C)OO1
|  SMILES2_Comment = trimer
|  InChI = 1/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3
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|C=9 |H=18 |O=6 
|  MolarMass = 222,236
|  Appearance = Bela kristalna čvrsta supstanca
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|  MeltingPt = 131.5 do 133&nbsp;°C (dimer)<ref>Federoff, Basil T. et al., ''Encyclopedia of Explosives and Related Items'' (Springfield, Virginia: National Technical Information Service, 1960), vol. 1, [https://archive.org/stream/Ullmans/01%20Ullmans-U-S-ARMY-Encyclopedia-of-Explosives-and-Related-Items-Vol-01#page/n147/mode/2up p. A41.]</ref> <br /> 91&nbsp;°C (trimer)
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| ShockSens = Visoko/Visoko kada je mokro
| FrictionSens = Visok/umeren kada je mokar
| DetonationV = 5300 [[metre per second|m/s]] pri maksimalnoj gustini (1.18 g/cm<sup>3</sup>), oko 2500–3000 m/s blizu 0.5 g/cm<sup>3</sup><br />17,384 ft/s<br />3.29 mmilja u sekundi
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Aceton peroksid ({{IPAc-en|æ|s|ə|'|t|ə|ʊ|n|_|p|ɛr|ˈ|ɒ|k|s|aɪ|d|audio=En-uk-Acetone peroxide.ogg}} koji se takođe naziva APEKS i majka Satane) je organski peroksid i primarni eksploziv i takođe je [[organsko jedinjenje]], koje sadrži 9 [[atom]]a [[ugljenik]]a i ima [[Молекулска маса|molekulsku masu]] od 222,236 [[Јединица атомске масе|-{''Da''}-]]. Proizveden je reakcijom [[aceton]]a i [[vodonik peroksid]]a da bi se dobila smeša linearnog monomera i cikličnog dimera, trimera i tetrameraforme. Dimer je poznat kao [[diaceton diperoksid]] (DADP). Trimer je poznat kao [[triaceton triperoksid]] (TATP) ili triciklični aceton peroksid (TCAP). '''Aceton peroksid''' ima oblik belog kristalnog praha sa karakterističnim mirisom nalik na izbeljivač (kada je nečist) ili mirisom nalik voću kada je čist, i može snažno da eksplodira ako je podvrgnut toploti, trenju, statičkom elektricitetu, koncentrovanoj [[Сумпорна киселина|sumpornoj kiselini]], jakom UV zračenje ili udaru. Otprilike do 2015. detektori eksploziva nisu bili podešeni da otkrivaju eksplozive bez [[azot]]a, jer je većina [[eksploziv]]a korišćenih pre 2015. bila zasnovana na [[azot]]u. '''TATP''', pošto ne sadrži [[azot]], korišćen je kao [[eksploziv]] izbora u nekoliko terorističkih bombaških napada od 2001.

== Istorija ==

'''Aceton peroksid''' (konkretno, triaceton triperoksid) je 1895. godine otkrio nemački hemičar [[Ričard Volfenštajn]].<ref>{{cite journal| first=R| last=Wolffenstein | title=Über die Einwirkung von Wasserstoffsuperoxyd auf Aceton und Mesityloxyd | trans-title = On the effect of hydrogen peroxide on acetone and mesityl oxide | language = de | journal = Berichte der Deutschen Chemischen Gesellschaft | volume=28 | issue=2 | pages= 2265–2269 | year=1895 | url = https://babel.hathitrust.org/cgi/pt?id=mdp.39015026352040;view=1up;seq=1001 | doi = 10.1002/cber.189502802208}}  Wolffenstein determined that acetone peroxide formed a trimer, and he proposed a structural formula for it.  From pp. 2266–2267:  ''"Die physikalischen Eigenschaften des Superoxyds, der feste Aggregatzustand, die Unlöslichkeit in Wasser etc. sprachen dafür, dass das Molekulargewicht desselben ein grösseres wäre, als dem einfachen Atomverhältnisse entsprach.  … Es lag also ein trimolekulares Acetonsuperoxyd vor, das aus dem monomolekularen entstehen kann, indem sich die Bindungen zwischen je zwei Sauerstoffatomen lösen und zur Verknüpfung mit den Sauerstoffatomen eines benachbarten Moleküls dienen.  Man gelangt so zur folgenden Constitutionsformel:  ''[diagram of proposed molecular structure of the trimer of acetone peroxide]'' .  Diese eigenthümliche ringförmig constituirte Verbindung soll Tri-Cycloacetonsuperoxyd genannt werden."'' (The physical properties of the peroxide, its solid state of aggregation, its insolubility in water, etc., suggested that its molecular weight would be a greater [one] than corresponded to its simple empirical formula. … Thus [the result of the molecular weight determination showed that] there was present a tri-molecular acetone peroxide, which can arise from the monomer by the bonds between each pair of oxygen atoms [on one molecule of acetone peroxide] breaking and serving as links to the oxygen atoms of a neighboring molecule.  One thus arrives at the following structural formula:  [diagram of proposed molecular structure of the trimer of acetone peroxide] .  This strange ring-shaped compound shall be named "tri-cycloacetone peroxide".)</ref><ref>Wolfenstein R (1895) Deutsches Reichspatent 84,953</ref><ref>{{cite book | last1 = Matyáš | first1 = Robert | last2 = Pachman | first2 = Jiří | title = Primary Explosives | date = 2013 | publisher = Springer | location = Berlin | isbn = 978-3-642-28436-6 | page = 262 | url = https://books.google.com/books?id=wfJHAAAAQBAJ&pg=PA262 }}</ref>  Volfenštajn je kombinovao [[aceton]] i [[vodonik peroksid]], a zatim je ostavio smešu da odstoji nedelju dana na sobnoj temperaturi, za koje vreme se istaložila mala količina kristala, koji su imali tačku topljenja od {{convert|97|C|F K}}. {{sfn|Wolffenstein|1895|p=2266}}

Godine 1899. [[Адолф фон Бајер|Adolf von Baeier]] i [[Viktor Viliger]] opisali su prvu sintezu dimera i opisali upotrebu kiselina za sintezu oba peroksida.<ref>{{cite journal |last1=Baeyer |first1=Adolf |last2=Villiger |first2=Victor |date=1899 |url=https://babel.hathitrust.org/cgi/pt?id=uc1.b3481889;view=1up;seq=1107 |title=Einwirkung des Caro'schen Reagens auf Ketone |trans-title=Effect of Caro's reagent on ketones [part 1] |journal=Berichte der Deutschen Chemischen Gesellschaft |volume=32  |issue=3 |pages=3625–3633|doi=10.1002/cber.189903203151 }} [https://babel.hathitrust.org/cgi/pt?id=uc1.b3481889;view=1up;seq=1114 see p. 3632.]</ref><ref>{{cite journal | last1 = Baeyer | first1 = Adolf | last2 = Villiger | first2 = Victor | year = 1900a | title = Über die Einwirkung des Caro'schen Reagens auf Ketone |trans-title=On the effect of Caro's reagent on ketones [part 3] | url = https://babel.hathitrust.org/cgi/pt?id=hvd.cl1i1y;view=1up;seq=868 | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 33 | issue = 1 | pages = 858–864 | doi = 10.1002/cber.190003301153 }}</ref><ref>{{cite journal | last1 = Baeyer | first1 = Adolf | last2 = Villiger | first2 = Victor | year = 1900b | title = Über die Nomenclatur der Superoxyde und die Superoxyde der Aldehyde |trans-title=On the nomenclature of peroxides and the peroxide of aldehydes | url = https://babel.hathitrust.org/cgi/pt?id=uc1.b3481891;view=1up;seq=1079 | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 33 | issue = 2| pages = 2479–2487 | doi = 10.1002/cber.190003302185 }}</ref><ref>Federoff, Basil T.  et al., ''Encyclopedia of Explosives and Related Items'' (Springfield, Virginia:  National Technical Information Service, 1960), vol. 1, [https://archive.org/stream/Ullmans/01%20Ullmans-U-S-ARMY-Encyclopedia-of-Explosives-and-Related-Items-Vol-01#page/n147/mode/2up p. A41.]</ref><ref>Matyáš, Robert and Pachman, Jirí, ed.s, ''Primary Explosives'' (Berlin, Germany:  Springer, 2013), p. 257.</ref> Bajer i Viliger su pripremili dimer kombinovanjem [[kalijum persulfat]]a u dietil etru sa [[aceton]]om, uz hlađenje. Nakon odvajanja etarskog sloja, proizvod je prečišćen i utvrđeno je da se topi na {{convert|132-133|C|F K}}. {{sfn|Baeyer|Villiger|1899|p=3632}} Otkrili su da se trimer može pripremiti dodavanjem hlorovodonične kiseline u ohlađenu smešu [[aceton]]a i [[vodonik peroksid]]a. {{sfn|Baeyer|Villiger|1900a|p=859}} Korišćenjem smanjenje tačaka smrzavanja da bi se odredile molekulske težine jedinjenja, takođe su utvrdili da je oblik '''aceton peroksida''' koji su pripremili preko [[kalijum persulfat]]a bio dimer, dok je '''aceton peroksid''' koji je pripremljen preko [[Хлороводонична киселина|hlorovodonične kiseline]] bio trimer, kao Volfenštajn složeni.<ref>{{harvnb|Baeyer|Villiger|1900a|p=859}} {{lang|de|"Das mit dem Caro'schen Reagens dargestellte, bei 132–133° schmelzende Superoxyd gab bei der Molekulargewichtsbestimmung nach der Gefrierpunktsmethode Resultate, welche zeigen, dass es dimolekular ist.  Um zu sehen, ob das mit Salzsäure dargestellte Superoxyd vom Schmp. 90–94° mit dem Wolffenstein'schen identisch ist, wurde davon ebenfalls eine Molekulargewichtsbestimmung gemacht, welche auf Zahlen führte, die für ein trimolekulares Superoxyd stimmen."}} [The peroxide that was prepared with Caro's reagent and that melted at {{convert|132|C|F}} to {{convert|133|C|F}} gave – according to a determination of molecular weight via the freezing point method – results which show that it is dimolecular.  In order to see whether the peroxide that was prepared with hydrochloric acid and that has a melting point of {{convert|90-94|C|F}} is identical to Wolffenstein's, a molecular weight determination of it was likewise made, which led to numbers that are correct for a trimolecular peroxide.]</ref>

Rad na ovoj metodologiji i na raznim dobijenim proizvodima, sredinom 20. veka dalje su istraživali Milas i Golubović.<ref name = MilasGolubovic59>{{cite journal | title = Studies in Organic Peroxides. XXVI. Organic Peroxides Derived from Acetone and Hydrogen Peroxide | vauthors = Milas NA, Golubović A | journal = [[Journal of the American Chemical Society]] | year = 1959 | volume = 81 | issue = 24 | pages = 6461–6462 | doi = 10.1021/ja01533a033 }}</ref>

== Osobine ==

{| class="wikitable sortable"
|-
! Osobina !! Vrednost
|-
| [[Водонична веза|Broj akceptora vodonika]] || 6
|-
| [[Водонична веза|Broj donora vodonika]] || 0
|-
| [[Геометрија молекула|Broj rotacionih veza]] || 0
|-
| [[Particioni koeficijent]]<ref>{{cite doi/10.1021/jp980230o|noedit}}</ref> (-{''ALogP'')}- || -0,6
|-
| [[Rastvorljivost]]<ref>{{cite pmid|11749573|noedit}}</ref> (-{''logS'', log(''mol/L''}-)) || -1,0
|-
| [[Polarna površina molekula|Polarna površina]]<ref>{{cite pmid|11020286|noedit}}</ref> (-{''PSA''}-, [[Ангстрем (јединица)|''Å''<sup>2</sup>]]) || 55,4 
|}

== Hemija ==

Hemijski naziv, '''aceton peroksid''' se najčešće koristi za označavanje cikličnog trimera, produkta reakcije između dva prekursora, [[vodonik-peroksid]]a i [[aceton]]a, u nukleofilnom dodatku katalizovanom kiselinom, iako su mogući različiti dalji monomerni i dimerni oblici.

[[File:Acetone Peroxide Synthesis V.2.svg|thumb|center|300px|Sinteza tricikličnog aceton peroksida.]]

Konkretno, dva dimera, jedan ciklični (C<sub>6</sub>H<sub>12</sub>O<sub>4</sub>) i jedan otvoreni lanac (C<sub>6</sub>H<sub>14</sub>O<sub>4</sub>), kao i otvoreni dihidroperoksid monomer (C<sub>3</sub>H<sub>8</sub>O<sub>4</sub>),<ref>This is not the [[DMDO]] monomer referred to in the Chembox, but rather the open chain, dihydro monomer described by Milas & Goluboviç, op. cit.</ref> se takođe može formirati; pod određenim skupom uslova koncentracije reagensa i kiselog katalizatora, ciklični trimer je primarni proizvod.<ref name = MilasGolubovic59/> Tetramerni oblik je takođe opisan, međutim, pod različitim katalitičkim uslovima,<ref name=jiang>{{cite journal | vauthors = Jiang H, Chu G, Gong H, Qiao Q | s2cid = 95733839 | title = Tin Chloride Catalysed Oxidation of Acetone with Hydrogen Peroxide to Tetrameric Acetone Peroxide | journal = Journal of Chemical Research| volume =28 | pages = 288–289 | year =1999 | doi =10.1039/a809955c | issue = 4}}</ref> sinteza tetramernog aceton peroksida je sporna.<ref>Primary Explosives - Robert Matyáš, Jiří Pachman (auth.), p.275</ref><ref name="Pachman, J. 2010">{{cite journal| last1=Matyáš| first1=R.| last2=Pachman| first2=J.| title=Study of TATP: Influence of reaction conditions on product composition.| journal=Propellants, Explosives, Pyrotechnics| volume=35| issue=1| pages=31–37| date=8 February 2010| access-date=30 August 2021| doi=10.1002/prep.200800044| url=https://onlinelibrary.wiley.com/doi/10.1002/prep.200800044| url-access=subscription}}</ref> Pod neutralnim uslovima, prijavljeno je da reakcija proizvodi monomerni organski peroksid .<ref name = MilasGolubovic59/>

Najčešći put za skoro čist TATP je H<sub>2</sub>O<sub>2</sub>/aceton/HCl u molarnim odnosima 1:1:0,25, koristeći 30% [[vodonik peroksid]]. Ovaj proizvod sadrži vrlo malo ili nimalo DADP-a sa vrlo malim tragovima hlorisanih jedinjenja. Proizvod koji sadrži veliku frakciju DADP može se dobiti od 50% H<sub>2</sub>O<sub>2</sub> korišćenjem velikih količina koncentrovane sumporne kiseline kao katalizatora ili alternativno sa 30% H<sub>2</sub>O<sub>2</sub> i ogromne količine HCl kao katalizator.<ref name="Pachman, J. 2010"/>

Proizvod napravljen korišćenjem hlorovodonične kiseline smatra se stabilnijim od onog napravljenog korišćenjem sumporne kiseline. Poznato je da tragovi [[Сумпорна киселина|sumporne kiseline]] zarobljeni unutar formiranih kristala [[aceton peroksid]]a dovode do nestabilnosti. U stvari, zarobljena [[sumporna kiselina]] može izazvati detonaciju na temperaturama od čak {{convert|50|C|F}}. Ovo je najverovatniji mehanizam iza slučajnih eksplozija [[aceton peroksid]]a koje se javljaju tokom sušenja na zagrejanim površinama.<ref>{{Cite journal|last1=Matyas|first1=Robert|last2=Pachman|first2=Jiri |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>

[[Triaceton triperoksid]] se formira u 2-propanolu nakon dugog stajanja u prisustvu vazduha.<ref>{{Cite journal|last1=Pye|first1=Cory|date=10 June 2020|title=Chemical Safety: TATP Formation in 2-Propanol| doi=10.1021/acs.chas.0c00061|journal=ACS Chemical Health & Safety|volume=27|issue=5|pages=279|s2cid=225762474}}</ref>

[[File:Tetrameric Acetone Peroxide 01.JPG|thumb|Tetramerni aceton peroksid]]

Organski peroksidi su generalno osetljivi, opasni [[eksploziv]]i, a svi oblici [[aceton peroksid]]a su osetljivi na iniciranje. '''TATP''' se eksplozivno razgrađuje; ispitivanje eksplozivnog raspadanja '''TATP-a''' na samoj ivici fronta detonacije predviđa „formiranje [[aceton]]a i [[ozon]]a kao glavnih proizvoda raspadanja, a ne intuitivno očekivanih produkata oksidacije“.<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> Veoma malo toplote stvara se eksplozivnim razlaganjem '''TATP-a''' na samoj ivici fronta detonacije; prethodna kompjuterska analiza sugeriše da je razgradnja '''TATP-a''' entropijska eksplozija.<ref name=pmid15669854/> Međutim, ova hipoteza je osporena jer nije u skladu sa stvarnim merenjima.<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> Tvrdnja o entropijskoj eksploziji vezana je za događaje odmah iza fronta detonacije. Autori iz 2004. Dubnikova et al. studije potvrđuju da se konačna redoks reakcija (sagorevanje) [[ozona]], [[kiseonik]]a i reaktivnih vrsta u vodu, različite okside i [[ugljovodonik]]e odvija u roku od oko 180 ps nakon početne reakcije - unutar oko mikrona detonacionog talasa. Detonirajući kristali '''TATP-a''' na kraju dostižu temperaturu od {{convert|2.030|C|K F}}  i pritisak od 80 kbara.<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 }}</ref> Konačna energija detonacije je oko 2800 kJ/kg (mereno u helijumu) – dovoljno da se ukratko podigne temperatura gasovitih proizvoda na {{convert|2.000|C|K F}}. Zapremina gasova kod STP je 855 L/kg za '''TATP''' i 713 L/kg za [[DADP]] (mereno u helijumu).<ref name="j.tca.2014"/>

Tetramerni oblik [[aceton peroksid]]a, pripremljen u neutralnim uslovima korišćenjem kalajnog katalizatora u prisustvu helatora ili opšteg inhibitora radikalne hemije, je navodno hemijski stabilniji, iako je i dalje veoma opasan primarni [[eksploziv]].<ref name=jiang/> NJegova sinteza je osporavana.<ref name="Pachman, J. 2010"/>

I T'''ATP''' i [[DADP]] su skloni gubitku mase sublimacijom. [[DADP]] ima nižu molekulsku težinu i veći pritisak pare. To znači da je [[DADP]] skloniji sublimaciji nego '''TATP'''.

Nekoliko metoda se može koristiti za analizu tragova '''TATP-a''',<ref>{{cite journal | vauthors = Schulte-Ladbeck R, Vogel M, Karst U | title = Recent methods for the determination of peroxide-based explosives | journal = [[Analytical and Bioanalytical Chemistry]] | volume = 386 | issue = 3 | pages = 559–65 | date = Oct 2006 | pmid = 16862379 | doi = 10.1007/s00216-006-0579-y | s2cid = 38737572 }}</ref> uključujući gasnu hromatografiju/masenu spektrometriju (GC/MS),<ref>{{cite journal | vauthors = Muller D, Levy A, Shelef R, Abramovich-Bar S, Sonenfeld D, Tamiri T | title = Improved method for the detection of TATP after explosion | url = https://archive.org/details/sim_journal-of-forensic-sciences_2004-09_49_5/page/935 | journal = [[Journal of Forensic Sciences]] | volume = 49 | issue = 5 | pages = 935–8 | date = Sep 2004 | doi = 10.1520/JFS2003003 | pmid = 15461093 }}</ref><ref>{{cite journal | vauthors = Stambouli A, El Bouri A, Bouayoun T, Bellimam MA | title = Headspace-GC/MS detection of TATP traces in post-explosion debris | journal = [[Forensic Science International]] | volume = 146 Suppl | pages = S191–4 | date = Dec 2004 | pmid = 15639574 | doi = 10.1016/j.forsciint.2004.09.060 }}</ref><ref>{{cite journal|doi=10.1002/prep.200400094|title=Determination of the Vapor Density of Triacetone Triperoxide (TATP) Using a Gas Chromatography Headspace Technique|journal=Propellants, Explosives, Pyrotechnics|volume=30|issue=2|pages=127|year=2005|last1=Oxley|first1=Jimmie C.|last2=Smith|first2=James L.|last3=Shinde|first3=Kajal|last4=Moran|first4=Jesse }}</ref><ref>{{cite journal | vauthors = Sigman ME, Clark CD, Fidler R, Geiger CL, Clausen CA | title = Analysis of triacetone triperoxide by gas chromatography/mass spectrometry and gas chromatography/tandem mass spectrometry by electron and chemical ionization | journal = [[Rapid Communications in Mass Spectrometry]] | volume = 20 | issue = 19 | pages = 2851–7 | year = 2006 | pmid = 16941533 | doi = 10.1002/rcm.2678 | bibcode = 2006RCMS...20.2851S }}</ref><ref>{{cite journal | vauthors = Romolo FS, Cassioli L, Grossi S, Cinelli G, Russo MV | title = Surface-sampling and analysis of TATP by swabbing and gas chromatography/mass spectrometry | journal = Forensic Science International | volume = 224 | issue = 1–3 | pages = 96–100 | date = Jan 2013 | pmid = 23219697 | doi = 10.1016/j.forsciint.2012.11.005 }}</ref> tečnu hromatografiju visokih performansi /masenu spektrometriju (HPLC) /MS),<ref>{{cite journal | vauthors = Widmer L, Watson S, Schlatter K, Crowson A | title = Development of an LC/MS method for the trace analysis of triacetone triperoxide (TATP) | journal = [[Analyst&nbsp;(journal)|The Analyst]] | volume = 127 | issue = 12 | pages = 1627–32 | date = Dec 2002 | pmid = 12537371 | doi = 10.1039/B208350G | bibcode = 2002Ana...127.1627W }}</ref><ref>{{cite journal | vauthors = Xu X, van de Craats AM, Kok EM, de Bruyn PC | title = Trace analysis of peroxide explosives by high performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry (HPLC-APCI-MS/MS) for forensic applications | url = https://archive.org/details/sim_journal-of-forensic-sciences_2004-11_49_6/page/1230 | journal = Journal of Forensic Sciences | volume = 49 | issue = 6 | pages = 1230–6 | date = Nov 2004 | pmid = 15568694 }}</ref><ref>{{cite journal | vauthors = Cotte-Rodríguez I, Hernandez-Soto H, Chen H, Cooks RG | title = In situ trace detection of peroxide explosives by desorption electrospray ionization and desorption atmospheric pressure chemical ionization | journal = Analytical Chemistry | volume = 80 | issue = 5 | pages = 1512–9 | date = Mar 2008 | pmid = 18247583 | doi = 10.1021/ac7020085 }}</ref><ref>{{cite journal | vauthors = Sigman ME, Clark CD, Caiano T, Mullen R | title = Analysis of triacetone triperoxide (TATP) and TATP synthetic intermediates by electrospray ionization mass spectrometry | journal = Rapid Communications in Mass Spectrometry | volume = 22 | issue = 2 | pages = 84–90 | year = 2008 | pmid = 18058960 | doi = 10.1002/rcm.3335 | bibcode = 2008RCMS...22...84S }}</ref><ref>{{cite journal | vauthors = Sigman ME, Clark CD, Painter K, Milton C, Simatos E, Frisch JL, McCormick M, Bitter JL | title = Analysis of oligomeric peroxides in synthetic triacetone triperoxide samples by tandem mass spectrometry | journal = Rapid Communications in Mass Spectrometry | volume = 23 | issue = 3 | pages = 349–56 | date = Feb 2009 | pmid = 19125413 | doi = 10.1002/rcm.3879 | bibcode = 2009RCMS...23..349S }}</ref>  i HPLC sa derivitizacijom nakon kolone.<ref name = KarstTraceAnalPerox>{{cite journal | vauthors = Schulte-Ladbeck R, Kolla P, Karst U | title = Trace analysis of peroxide-based explosives | journal = Analytical Chemistry | volume = 75 | issue = 4 | pages = 731–5 | date = Feb 2003 | pmid = 12622359 | doi = 10.1021/ac020392n }}</ref>

'''Aceton peroksid''' je rastvorljiv u [[toluen]]u, [[hloroform]]u, [[aceton]]u, [[dihlorometan]]u i [[metanol]]u.<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> Rekristalizacija primarnih [[eksploziv]]a može dati velike kristale koji spontano detoniraju usled unutrašnjeg naprezanja.<ref>Primary Explosives - page 278, {{ISBN|9783642284359}}</ref>

== Hemijska svojstva ==

Kada se zagreva sa razblaženom sumpornom kiselinom, aceton peroksid se kvantitativno hidrolizuje sa stvaranjem acetona i vodonik peroksida: {{sfn|Багал|1975}}

: <math>\mathsf{C_6H_{12}O_4 + 2H_2O \rightarrow 2C_3H_6O + 2H_2O_2}.</math>

Miligramske količine [[aceton diperoksid]]a i [[triperoksid]]a se razlažu u roku od 15 minuta jakim kiselinama (kao što su [[sumporna kiselina]] ili metansulfonska kiselina). Pošto je reakcija egzotermna, dejstvo jakih kiselina na gramske količine izaziva detonaciju. Takođe, [[aceton triperoksid]] efikasno uništava [[kalaj(II) hlorid]].<ref>{{статья|автор=Oxley J. C., Smith J. L., Huang J., Luo W.|заглавие=Destruction of Peroxide Explosives|ссылка=https://archive.org/details/sim_journal-of-forensic-sciences_2009-09_54_5/page/1029|язык=en|издание=Journal of Forensic Sciences|год=2009|том=54|номер=5|страницы=1029—1033|doi=10.1111/j.1556-4029.2009.01130.x|pmid=19737243}}</ref>

Kada se priprema korišćenjem metansulfonske kiseline, perhlorne kiseline ili [[sumporna kiselina|sumporne kiseline]], [[aceton triperoksid]] se spontano pretvara u [[aceton diperoksid]]. Međutim, kada se koristi [[kalaj(IV) hlorid]], hlorovodonična ili [[azotna kiselina]], ostaje stabilan.<ref>{{статья|автор=Matyas R., Pachman J., Ang H.-G.|заглавие=Study of TATP: Spontaneous Transformation of TATP to DADP|язык=en|издание=Propellants, Explosives, Pyrotechnics|год=2008|том=33|номер=2|страницы=89—91|doi=10.1002/prep.200700247}}</ref>.

== Fizička svojstva ==

[[Aceton triperoksid]] se lako sublimira:

* na temperaturama od {{convert|+14|C|K F}} gubi oko 6,5% mase za 24 sata;
* na {{convert|25|C|K F}} - 68% mase za 14 dana;
* na {{convert|50|C|K F}} - 1,5% mase za 2 sata;
* na {{convert|100|C|K F}} sublimiše veoma brzo.

Rastvorljiv je u etanolu (0,15 g/100 g na {{convert|17|C|K F}}), dietil etru (5,5), petrol etru (7,35), [[aceton]]u (9,15), [[ugljen-disulfid]]u (9,97), piridinu (15,4), benzenu (18,0), trihloretilen (22.7), [[ugljen-tetrahlorid]] (24.8), [[hloroform]] (42.5), ali nerastvorljiv u vodi.

== Industrijska upotreba ==

Keton peroksidi, uključujući '''aceton peroksid''' i [[metil etil keton peroksid]], nalaze primenu kao inicijatori za reakcije polimerizacije, npr. silikonske ili poliesterske smole u izradi kompozita ojačanih [[fiberglas]]om. Za ove upotrebe, peroksidi su tipično u obliku razblaženog rastvora u organskom rastvaraču; [[metil etil keton peroksid]] je češći za ovu svrhu, jer je stabilan u skladištenju.

'''Aceton peroksid''' se koristi kao sredstvo za izbeljivanje.<ref>{{cite journal | vauthors = Ferrari CG, Higashiuchi K, Podliska JA | title = Flour Maturing and Bleaching with Acyclic Acetone Peroxides | journal = Cereal Chemistry | year = 1963 | volume = 40 | pages = 89–100 | url = http://www.aaccnet.org/publications/cc/backissues/1963/Documents/chem40_89.pdf | access-date = 25 March 2016 | archive-date = 20 February 2017 | archive-url = https://web.archive.org/web/20170220170905/http://www.aaccnet.org/publications/cc/backissues/1963/Documents/chem40_89.pdf | url-status = dead }}</ref>

'''Aceton peroksidi''' su neželjeni nusproizvodi nekih reakcija oksidacije kao što su one koje se koriste u sintezi [[fenol]]a.<ref name=Costantini>{{cite patent |country=US |number=5003109 |status= |title=Destruction of acetone peroxide |pubdate=1991-03-26 |gdate= |fdate= |pridate= |inventor=Costantini, Michel |invent1= |invent2=}}</ref> Zbog njihove eksplozivne prirode, njihovo prisustvo u hemijskim procesima i hemijskim uzorcima stvara potencijalno opasne situacije. Moguća je slučajna pojava u ilegalnim MDMA laboratorijama.<ref>{{Cite book|title=Counter-Terrorism for Emergency Responders, Second Edition|isbn=9781138747623|pages=213|last1=Burke|first1=Robert A.|date=25 July 2006}}</ref> Brojne metode se koriste za smanjenje njihovog izgleda, uključujući pomeranje pH na više alkalni, podešavanje temperature reakcije ili dodavanje inhibitora njihove proizvodnje.<ref name=Costantini/> Na primer, [[triaceton peroksid]] je glavni zagađivač koji se nalazi u diizopropil etru kao rezultat fotohemijskih oksidacija na vazduhu.<ref>{{cite journal | doi = 10.1021/ja01248a501| title = Trimolecular Acetone Peroxide in Isopropyl Ether| journal = Journal of the American Chemical Society| volume = 65| issue = 8| pages = 1652| year = 1943| vauthors = Acree F, Haller HL }}</ref>

== Koristi se kao dodatak ishrani ==

'''Aceton peroksid''' je aditiv za hranu sa oznakom E929. Poboljšava kvalitet proizvoda od brašna. Međutim, od 2017. godine, '''aceton peroksid''' se praktično ne koristi u ove svrhe, već se koriste drugi poboljšivači.

== Upotreba improvizovanih eksplozivnih naprava u terorističkim akcijama ==

'''TATP''' je korišćen u bombaškim i samoubilačkim napadima i u improvizovanim eksplozivnim napravama, uključujući [[Напади у Лондону 7. јула 2005.|bombaške napade u Londonu 7. jula 2005. godine]], gde su četiri bombaša samoubice ubila 52 osobe i ranila više od 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 |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 | date = 15 July 2005 | website = New Scientist }}</ref> bio je jedan od [[eksploziv]]a koji je koristio „bombaš cipela“ [[Ričard Rid]]<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|access-date=04. 08. 2023|archive-date=28. 06. 2024|archive-url=https://web.archive.org/web/20240628025301/https://edition.cnn.com/2001/US/12/28/inv.reid/|url-status=}}</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" /> u svom neuspešnom pokušaju bombe u cipelama 2001. godine i koristili su ga bombaši samoubice u [[Напади у Паризу 13. новембра 2015.|napadima u Parizu novembra 2015.]]<ref name="nyt-isis">{{cite news | first1 =  Rukmini | last1 = Callimachi | first2 = Alissa J. | last2 = Rubin | first3 = Laure | last3 = Fourquet | 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> bombaški napadi u Briselu 2016.,<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> [[Бомбашки напад у Манчестер арени 2017.|Bombaški napad u Mančester Areni]], napad u Briselu juna 2017,<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 |date=25 May 2017|work=The Guardian|access-date=16 September 2017|language=en-GB}}</ref> Bombaški napad na Parsons Green,<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> bombaški napad u Surabaji,<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> i uskršnji bombaški napad na Šri Lanku 2019.<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> Policija Hong Konga tvrdi da je pronašla {{convert|2|kg|lb}} '''TATP-a''' među oružjem i protestnim materijalom u julu 2019, kada su se održavali masovni protesti protiv predloženog zakona koji dozvoljava ekstradiciju kontinentalnoj [[Kina|Kini]].<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>

Nadpritisak udarnog talasa '''TATP-a''' je 70% od onog za [[TNT (eksploziv)|TNT]], pozitivni fazni impuls je 55% od [[TNT ekvivalent]]a. '''TATP''' na 0,4 g/cm³ ima oko jednu trećinu brizantnosti [[TNT (eksploziv)|TNT-a]] (1,2 g/cm³) merene [[Hesov test|Hesovim testom]].<ref>{{Cite journal |doi = 10.1007/s00193-014-0497-4|bibcode = 2014ShWav..24..439P|title = Study of TATP: Blast characteristics and TNT equivalency of small charges|journal = Shock Waves|volume = 24|issue = 4|pages = 439|last1 = Pachman|first1 = J|last2 = Matyáš|first2 = R|last3 = Künzel|first3 = M|year = 2014|s2cid = 122101166}}</ref>

'''TATP''' je privlačan teroristima jer se lako priprema od lako dostupnih maloprodajnih sastojaka, kao što su izbeljivač za kosu i sredstvo za uklanjanje laka za nokte.<ref name="nyt-isis" /> Takođe je bio u stanju da izbegne detekciju jer je jedan od retkih visokih eksploziva koji ne sadrže [[azot]],<ref name="mother of satan" />  i stoga je mogao neotkriveno da prođe kroz standardne skenere za [[Detekcija eksploziva|detekciju eksploziva]], koji su do sada bili dizajnirani za otkrivanje azotnih eksploziva.<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> Do 2016. detektori eksploziva su modifikovani da bi mogli da otkriju '''TATP''', a razvijeni su i novi tipovi.<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/>

U [[Европска унија|Evropskoj uniji]] donete su zakonske mere za ograničavanje prodaje [[vodonik peroksid]]a koncentrisanog na 12% ili više %.<ref>{{Cite web|url=https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX%3A02019R1148-20190711|title=Regulation (EU) No 2019/1148 of the European Parliament and of the Council of 20 June 2019 on the marketing and use of explosives precursors}}</ref>

Ključni nedostatak je velika podložnost '''TATP-a''' slučajnoj detonaciji, uzrokujući povrede i smrt među ilegalnim proizvođačima bombi, što je dovelo do toga da se TATP naziva "Majka satane". [<ref name=satan>{{cite web|last1  = Genuth | first1 = Iddo  | last2 = Fresco-Cohen | first2 = Lucille |title = TATP: Countering the Mother of Satan |publisher = The Future of Things |date = 6 November 2006 |url = http://thefutureofthings.com/articles/35/tatp-countering-the-mother-of-satan.html |quote = The tremendous devastative force of TATP, together with the relative ease of making it, as well as the difficulty in detecting it, made TATP one of the weapons of choice for terrorists |access-date = 24 September 2009}}</ref><ref name="mother of satan">{{cite web | last = Glas | first = Kristin | title = TATP: Countering the Mother of Satan | publisher = The Future of Things | date = 2006-11-06 | url =http://thefutureofthings.com/3035-tatp-countering-the-mother-of-satan/ | quote = The tremendous devastative force of TATP, together with the relative ease of making it, as well as the difficulty in detecting it, made TATP one of the weapons of choice for terrorists | access-date =24 September 2009}}</ref> TATP je pronađen u slučajnoj eksploziji koja je prethodila terorističkim napadima 2017. u Barseloni i okolnim područjima.<ref name="GDNBarcelonaTATP">{{Cite news|url=https://www.theguardian.com/world/2017/aug/20/spain-attacks-king-joins-public-at-mass-for-victims-in-barcelona | title=Police extend hunt for Barcelona attack suspect across Europe|last1=Watts |first1=Jonathan |last2=Burgen |first2=Stephen |date=21 August 2017|work=The Guardian|access-date=16 September 2017 }}</ref>

Sintezu '''TATP-a''' velikih razmera često izneveravaju preterani mirisi poput izbeljivača ili voća. Ovaj miris može čak da prodre u odeću i kosu u količinama koje su prilično primetne, to je zabeleženo u bombaškim napadima u Briselu 2016.<ref>{{cite news|author=Andrew Higgins|author2=Kimiko de Freytas-Tamura|title=In Brussels Bombing Plot, a Trail of Dots Not Connected|url=https://www.nytimes.com/2016/03/27/world/europe/in-brussels-bombing-plot-a-trail-of-dots-not-connected.html|access-date=28 March 2016|newspaper=The New York Times|date=26 March 2016}}</ref>

== Reference ==
{{reflist|2}}

== Literatura ==

{{Литература}}
* {{Clayden1st}}
* {{March6th}}
* {{Katritzky2nd}}
{{Литература крај}}

== Spoljašnje veze ==

{{Portal-lat|Hemija}}
{{Commonscat-lat|Acetone peroxide}}
* {{PubChemInCheKey|ZTLXICJMNFREPA-UHFFFAOYSA-N|Acetone peroxide}}
* [http://chemsub.online.fr/name/triacetone_triperoxide.html ChemSub Online: Acetone peroxide – Triacetone triperoxide.]

{{normativna kontrola}}

[[Категорија:Пероксиди]] 
[[Категорија:Органски пероксиди]]
[[Категорија:Експлозивне хемикалије]]