Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Acetone peroxide: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 19:53, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470790171 of page Acetone_peroxide for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 21:40, 5 December 2024 edit Citation bot (talk | contribs)Bots5,424,097 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Dominic3203 | Linked from User:Mako001/sandbox | #UCB_webform_linked 236/3639 
Line 1: Line 1:
{{Redirect|TATP|Tahrir Alley Technology Park|The American University in Cairo|Telecommunication Application Transaction Processing benchmark|TATP Benchmark}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=September 2024}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 453998664
| Watchedfields = changed
| ImageFile = acetone peroxide.png
| verifiedrevid = 477239343
| ImageSize = 180px
| Name =
| ImageFileL2 = acetone-peroxide-trimer-3D-balls.png
| ImageFile =
| ImageSizeL2 = 180px
| ImageNameL2 = Acetone peroxide trimer | ImageFile1 = Acetone peroxide.svg
| ImageSize1 =
| ImageFileR2 = acetone peroxide.jpg
| ImageCaption1 = Cyclic dimer and trimer examples
| ImageSizeR2 = 180px
| ImageFileL2 = Acetone-peroxide-trimer-from-xtal-2009-3D-balls.png
| IUPACName = 3,3,6,6-Tetramethyl-1,2,4,5-tetraoxane<br>(dimer)<br>3,3,6,6,9,9-Hexamethyl-1,2,4,<br>5,7,8-hexaoxacyclononane<br>(trimer)
| ImageSizeL2 = 138px
| OtherNames =
| ImageNameL2 = Acetone peroxide trimer
| Section1 = {{Chembox Identifiers
| ImageFileR2 = acetone peroxide.jpg
| ImageSizeR2 = 180px
| IUPACName = ] ''(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)''
| OtherNames = Triacetone triperoxide<br />Peroxyacetone<br />Mother of Satan
| SystematicName =
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3582942 | ChemSpiderID = 3582942
| InChI = 1/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3 | InChI = 1/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3
| InChIKey = ZTLXICJMNFREPA-UHFFFAOYAS | InChIKey = ZTLXICJMNFREPA-UHFFFAOYAS
| SMILES1 = CC1(OOC(OOC(OO1)(C)C)(C)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3 | StdInChI = 1S/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZTLXICJMNFREPA-UHFFFAOYSA-N | StdInChIKey = ZTLXICJMNFREPA-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 17088-37-8 --> | CASNo = 1336-17-0
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 536100
| UNII = 62T938ZGDD
| SMILES = CC1(C)OOC(C)(C)OO1 (dimer)<br>CC1(C)OOC(C)(C)OOC(C)(C)OO1 (trimer)
| PubChem = 4380970
| SMILES1 = CC1(C)OOC(C)(C)OO1
| SMILES1_Comment = dimer
| SMILES2 = CC1(C)OOC(C)(C)OOC(C)(C)OO1
| SMILES2_Comment = trimer
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>12</sub>O<sub>4</sub> (dimer)<br>C<sub>9</sub>H<sub>18</sub>O<sub>6</sub> (trimer) | Formula = C<sub>6</sub>H<sub>12</sub>O<sub>4</sub> (dimer)<br />C<sub>9</sub>H<sub>18</sub>O<sub>6</sub> (trimer)<br />C<sub>12</sub>H<sub>24</sub>O<sub>8</sub> (tetramer)
| MolarMass = 148.157&nbsp;g/mol&nbsp;(dimer)<br>222.24&nbsp;g/mol (trimer) | MolarMass = 148.157&nbsp;g/mol&nbsp;(dimer)<br />222.24&nbsp;g/mol (trimer)<br/>296.296&nbsp;g/mol (tetramer)<ref>{{cite web | url=https://www.webqc.org/molecular-weight-of-C12H24O8.html | title=Molar mass C12H24O8 }}</ref>
| Appearance = White crystalline solid | Appearance = White crystalline solid
| Density = | Density =
| MeltingPt = 131.5 to 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, </ref> <br /> 91&nbsp;°C (trimer)
| MeltingPtC = 91
| BoilingPtC = 97 to 160
| BoilingPt = 97–160 °C
| BoilingPt_notes =
| Solubility = insoluble
| Solubility = Insoluble
}}
}}
| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
| MainHazards = Explosive
| GHSPictograms = {{GHS01}} {{GHS07}}
| NFPA-F = 4
| NFPA-H = 1
| NFPA-R = 4
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
| Section4 =
| Section6 = {{Chembox Explosive
| ShockSens = High / moderate when wet | Section5 =
| Section6 = {{Chembox Explosive
| FrictionSens = High / moderate when wet
| ShockSens = High/High when wet
| ExplosiveV = 5300 ]<br>17,384 ft/s<br>3.29 miles per second
| FrictionSens = High/moderate when wet
| REFactor = .83}}
| DetonationV = 5300 ] at maximum density (1.18 g/cm<sup>3</sup>), about 2500–3000 m/s near 0.5 g/cm<sup>3</sup><br />17,384 ft/s<br />3.29 miles per second
| REFactor = 0.80}}
}} }}

'''Acetone peroxide''' ({{IPAc-en|æ|s|ə|'|t|ə|ʊ|n|_|p|ɛr|ˈ|ɒ|k|s|aɪ|d|audio=En-uk-Acetone peroxide.ogg}} also called '''APEX''' and '''mother of Satan'''<ref>{{cite web|title=TATP: The Chemistry of 'Mother of Satan' Explosive|url=https://www.acsh.org/news/2018/11/14/tatp-chemistry-mother-satan-explosive-13601|publisher=American Council on Science and Health|first=Alex|last=Berezow|date=14 Nov 2018}}</ref><ref>{{cite news|url=https://news.yahoo.com/mother-satan-know-explosive-used-195300455.html|agency=Yahoo News|title=What Is 'Mother of Satan'? What You Should Know About Explosive Used in Brussels Attacks|first=Anna|last=Swartz|date=24 Mar 2016}}</ref>) is an ] and a ]. It is produced by the reaction of ] and ] to yield a mixture of linear ] and ] ], ], and ] forms. The monomer is ]. The dimer is known as '''diacetone diperoxide''' ('''DADP'''). The trimer is known as '''triacetone triperoxide''' ('''TATP''') or '''tri-cyclic acetone peroxide''' ('''TCAP'''). Acetone peroxide takes the form of a white crystalline powder with a distinctive ]-like odor when impure, or a fruit-like smell when pure, and can explode powerfully if subjected to heat, friction, static electricity, concentrated sulfuric acid, strong UV radiation, or ]. Until about 2015, explosives detectors were not set to detect non-nitrogenous explosives, as most explosives used preceding 2015 were nitrogen-based. TATP, being nitrogen-free, has been used as the explosive of choice in several ] bomb attacks since 2001.

== History ==
Acetone peroxide (specifically, triacetone triperoxide) was discovered in 1895 by the German chemist ].<ref>{{cite journal| first=R| last=Wolffenstein | name-list-style = vanc | 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: '''' . 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 than corresponded to its simple empirical formula. … Thus there was present a tri-molecular acetone peroxide, which can arise from the monomer by the bonds between each pair of oxygen atoms breaking and serving as links to the oxygen atoms of a neighboring molecule. One thus arrives at the following structural formula: . 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 | name-list-style = vanc | 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> Wolffenstein combined ] and ], and then he allowed the mixture to stand for a week at room temperature, during which time a small quantity of crystals precipitated, which had a melting point of {{cvt|97|°C}}.{{sfn|Wolffenstein|1895|p=2266}}

In 1899, ] and ] described the first synthesis of the dimer and described use of acids for the synthesis of both peroxides.<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 |journal=Berichte der Deutschen Chemischen Gesellschaft |volume=32 |issue=3 |pages=3625–3633|doi=10.1002/cber.189903203151 }} </ref><ref>{{cite journal | last1 = Baeyer | first1 = Adolf | last2 = Villiger | first2 = Victor | name-list-style = vanc | year = 1900a | title = Über die Einwirkung des Caro'schen Reagens auf Ketone |trans-title=On the effect of Caro's reagent on ketones | 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 | name-list-style= vanc | 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://zenodo.org/records/1425972/files/article.pdf | 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, </ref><ref>Matyáš, Robert and Pachman, Jirí, ed.s, ''Primary Explosives'' (Berlin, Germany: Springer, 2013), p. 257.</ref> Baeyer and Villiger prepared the dimer by combining ] in ] with acetone, under cooling. After separating the ether layer, the product was purified and found to melt at {{cvt|132–133|°C}}.{{sfn|Baeyer|Villiger|1899|p=3632}} They found that the trimer could be prepared by adding ] to a chilled mixture of acetone and hydrogen peroxide.{{sfn|Baeyer|Villiger|1900a|p=859}} By using the ] to determine the molecular weights of the compounds, they also determined that the form of acetone peroxide that they had prepared via potassium persulfate was a dimer, whereas the acetone peroxide that had been prepared via hydrochloric acid was a trimer, like Wolffenstein's compound.<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."}} </ref>

Work on this methodology and on the various products obtained, was further investigated in the mid-20th century by Milas and 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 = ] | year = 1959 | volume = 81 | issue = 24 | pages = 6461–6462 | doi = 10.1021/ja01533a033 | bibcode = 1959JAChS..81.6461M }}</ref>

== Chemistry ==
The chemical name ''acetone peroxide'' is most commonly used to refer to the cyclic trimer, the product of a reaction between two ], hydrogen peroxide and acetone, in an acid-] ], although monomeric and dimeric forms are also possible.<ref>{{Cite journal |last1=Fukuzumi |first1=Kazuo |last2=Miyakawa |first2=Takero |last3=Morohira |first3=Hidenori |date=1965 |title=Monomeric dihydroperoxide concentrates from autoxidized methyl docosahexaenoate |url=https://aocs.onlinelibrary.wiley.com/doi/10.1007/BF02540046 |journal=Journal of the American Oil Chemists' Society |language=en |volume=42 |issue=8 |pages=717–720 |doi=10.1007/BF02540046 |issn=0003-021X}}</ref><ref>{{Cite web |author-link=United States Department of Homeland Security |date=2013 |title=2013 Annual Report from the Center of Excellence for Explosive Detection, Mitigation and Response in the Department of Homeland Security |url=http://energetics.chm.uri.edu/system/files/2013AnnualReportComplete.pdf |access-date=17 February 2024 |language=en}}</ref>

]
Specifically, two dimers, one cyclic (C<sub>6</sub>H<sub>12</sub>O<sub>4</sub>) and one open chain (C<sub>6</sub>H<sub>14</sub>O<sub>4</sub>), as well as an open dihydroperoxide monomer (C<sub>3</sub>H<sub>8</sub>O<sub>4</sub>),<ref>This is not the ] monomer referred to in the Chembox, but rather the open chain, dihydro monomer described by Milas & Goluboviç, op. cit.</ref> can also be formed; under a particular set of conditions of reagent and acid catalyst concentration, the cyclic trimer is the primary product.<ref name = MilasGolubovic59/> Under neutral conditions, the reaction is reported to produce the ]ic ].<ref name = MilasGolubovic59/>

A tetrameric form has also been described, under different catalytic conditions,<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> albeit not without disputes and controversy.<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>

The most common route for nearly pure TATP is H<sub>2</sub>O<sub>2</sub>/acetone/HCl in 1:1:0.25 molar ratios, using 30% hydrogen peroxide. This product contains very little or none of DADP with some very small traces of chlorinated compounds. Product that contains large fraction of DADP can be obtained from 50% H<sub>2</sub>O<sub>2</sub> using large amounts of concentrated sulfuric acid as catalyst or alternatively with 30% H<sub>2</sub>O<sub>2</sub> and massive amounts of HCl as a catalyst.<ref name="Pachman, J. 2010"/>

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 ].{{citation needed|date=March 2016}} TATP decomposes explosively; examination of the explosive ] of TATP at the very edge of detonation front predicts "formation of ] and ] 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 |bibcode=2005JAChS.127.1146D }}</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 ].<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| bibcode = 2014TcAc..585...10S }}</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}}] 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 | bibcode = 2005JAChS.12711053V| 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 ] 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 ] catalyst in the presence of a ] or general inhibitor of ], is reported to be more chemically stable, although still a very dangerous ].<ref name=jiang/> Its synthesis has been disputed.<ref name="Pachman, J. 2010"/>

Both TATP and DADP are prone to loss of mass via ]. DADP has lower ] and higher ]. 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 ].

Several methods can be used for trace analysis of TATP,<ref>{{cite journal | vauthors = Schulte-Ladbeck R, Vogel M, Karst U | title = Recent methods for the determination of peroxide-based explosives | journal = ] | volume = 386 | issue = 3 | pages = 559–65 | date = Oct 2006 | pmid = 16862379 | doi = 10.1007/s00216-006-0579-y | s2cid = 38737572 }}</ref> including gas chromatography/mass spectrometry (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 | journal = ] | 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 = ] | 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 | name-list-style = vanc }}</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 = ] | 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> ]/mass spectrometry (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 = ] | 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 | 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 | doi-access = free }}</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> and HPLC with post-column derivitization.<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>

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'', p. 278, {{ISBN|9783642284359}}.</ref>

<gallery widths="200px" heights="200px">
File:Tetrameric Acetone Peroxide 01.JPG|Tetrameric acetone peroxide
File:Sublimed TATP.jpg|Crystal deposits of sublimed TATP.
</gallery>

== Industrial uses ==
] peroxides, including acetone peroxide and ], find application as ]s for ] reactions, e.g., ] or ] ]s, in the making of ]-reinforced composites.{{citation needed|date=March 2016}} For these uses, the peroxides are typically in the form of a dilute solution in an organic solvent; methyl ethyl ketone peroxide is more common for this purpose, as it is stable in storage.{{citation needed|date=March 2016}}

Acetone peroxide is used as a ] to bleach and "mature" flour.<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>

Acetone peroxides are unwanted by-products of some oxidation reactions such as those used in ] syntheses.<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> Due to their explosive nature, their presence in chemical processes and chemical samples creates potential hazardous situations. For example, triacetone peroxide is the major contaminant found in ] as a result of ] oxidation in air.<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 | bibcode = 1943JAChS..65.1652A}}</ref> Accidental occurrence at illicit ] laboratories is possible.<ref>{{Cite book|title=Counter-Terrorism for Emergency Responders, Second Edition|isbn=9781138747623|pages=213|last1=Burke|first1=Robert A.|date=25 July 2006|publisher=CRC Press LLC |quote=Acetone peroxide can also occur accidentally...It is also a hazardous by-product of isosafrole oxidation in acetone, a step in illicit synthesis of MDMA, the street drug ecstasy.}}</ref>

Numerous methods are used to reduce their appearance, including shifting ] to more alkaline, adjusting reaction temperature, or adding ]s of their production.<ref name=Costantini/>{{additional citation needed |reason=current reference only mentions in-situ removal with pH modification, storage isn't covered|date=February 2024}}

== Use in improvised explosive devices ==
{{See also|Improvised explosive device}}

TATP has been used in bomb and suicide attacks and in improvised explosive devices, including the ], where four suicide bombers killed 52 people and injured more than 700.<ref>, '']'', 7 May 2006</ref><ref>]<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" ]<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 ] and was used by the suicide bombers in the ],<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> ],<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> ], ],<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> ],<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 ],<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 ].<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> News First (Sri Lanka), Retrieved on 23 April 2019.</ref> ] 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 ].<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 ] overpressure is 70% of that for TNT, and the positive phase impulse is 55% of the ]. TATP at 0.4 g/cm<sup>3</sup> has about one-third of the ] of TNT (1.2 g/cm<sup>3</sup>) measured by the Hess test.<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 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 ],<ref name="mother of satan" /> and could therefore pass undetected through standard ] 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/>

Legislative measures to limit the sale of hydrogen peroxide concentrated to 12% or higher have been made in the European Union.<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>

A key disadvantage is the high susceptibility of TATP to accidental detonation, causing injuries and deaths among illegal bomb-makers, which has led to TATP being referred to as the "Mother of Satan".<ref name=satan>{{cite web|last1 = Genuth | first1 = Iddo | last2 = Fresco-Cohen | first2 = Lucille | name-list-style = vanc |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 | name-list-style = vanc | 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 was found in the accidental explosion that preceded the ].<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 | name-list-style = vanc |date=21 August 2017|work=The Guardian|access-date=16 September 2017 }}</ref>

Large-scale TATP synthesis is often betrayed by excessive bleach-like or fruity smells. This smell can even penetrate into clothes and hair in amounts that are quite noticeable; this was reported in the ].<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>

==References==
{{reflist}}

== External links ==
*{{Commons category-inline|Acetone peroxide}}

{{Authority control}}
{{Use British English|date=September 2024}}

{{DEFAULTSORT:Acetone Peroxide}}
]
]
]
]
]
]