Acetone peroxide: Difference between revisions

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== Chemistry ==
 
The chemical name ''acetone peroxide'' is most commonly used to refer to the cyclic trimer, the product of a reaction between two [[Precursor (chemistry)|precursors]], hydrogen peroxide and acetone, in an acid-[[catalyst|catalyzed]] [[nucleophilic addition]], although various further monomeric and dimeric forms are also possible.<ref>{{citationCite journal |last=Fukuzumi |first=Kazuo |last2=Miyakawa |first2=Takero |last3=Morohira |first3=Hidenori needed|date=March1965 2016|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=February 17, 2024 |language=en}}</ref>
 
[[File:Acetone Peroxide Synthesis V.2.svg|thumb|center|300px|Synthesis of tri-cyclic acetone peroxide.]]
Specifically, two dimers, one cyclic (C<sub>6</sub>H<sub>12</sub>O<sub>4</sub>){{citation needed|date=March 2016}} 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 [[DMDO]] 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/> A tetrameric form has also been described, under different catalytic conditions, however.<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> the synthesis of tetrameric acetone peroxide has been disputed.<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> Under neutral conditions, the reaction is reported to produce the [[monomer]]ic [[organic peroxide]].<ref name = MilasGolubovic59/>
 
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"/>