Factors Influencing Destruction of Triacetone Triperoxide (TATP)

Oxley, Jimmie C.; Smith, James L.; Brady, Joseph E.; Steinkamp, Lucus

doi:10.1002/prep.201300063

Cited by 18 publications

(8 citation statements)

References 15 publications

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“…Cyclic peroxide breakdown intermediates under acidic conditions have been proposed to be peroxy/hydroperoxy oligomers or dimers. 2,7,13 It seems therefore, that the present reaction is fundamentally different to the broadly accepted mechanism of acidic degradation.…”

Section: Dalton Transactions Papermentioning

confidence: 78%

Rapid degradation of cyclic peroxides by titanium and antimony chlorides

et al. 2015

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First responders face extraordinary risks when dealing with organic peroxides such as TATP due to the extreme sensitivity of this class of explosives, and to a lack of a robust chemical means of safe and rapid neutralisation. The Lewis acids TiCl4 and SbCl3 have been found to demonstrate a novel degradation mechanism, with TiCl4 degrading a model cyclic peroxide in minutes when used in a two-fold excess, or ∼3 hours at half equivalence. The products cannot re-form peroxide compounds as is the case with acid degradation, suggesting the two mechanisms are fundamentally different. The Lewis acids mediate a rearrangement reaction in the cyclic peroxide backbone leading to relatively innocuous products through deactivation of oxidising O. Sub-stoichiometric TiCl4 reactions highlight a secondary reaction pathway that also leads to some oxidative chlorination products, possibly mediated by an unconfirmed titanium-oxychloride species. SbCl3 was found to exhibit similar reactivity to TiCl4, although at a slower rate. A mechanism is proposed, consistent with the observations for both stoichiometric and sub-stoichiometric quantities of TiCl4.

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Section: Dalton Transactions Papermentioning

confidence: 78%

Rapid degradation of cyclic peroxides by titanium and antimony chlorides

et al. 2015

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“…Triacetone triperoxide (TATP, 5 ) and diacetone diperoxide (DADP, 6 ) were prepared through acid-promoted condensations of acetone with hydrogen peroxide − Peroxide 7 was prepared from the corresponding tertiary bromide following a reported procedure; peroxide 8 was available through methylation of the known tertiary hydroperoxide …”

Section: Results and Discussionmentioning

confidence: 99%

“…Reduction of activated peroxides, for example, peroxyacetals, ozonides, or peresters, been accomplished using a variety of reagents . However, the reduction of unactivated dialkyl peroxides is more challenging. , Reduction of DADP and TATP, of particular interest due to their ready availability as well as their use in acts of terrorism, − has been achieved with SnCl 2 in boiling ethanol, with Cr 3+ or Co 2+ species, , or with alloyed bimetals or emulsified metals . Although Fe(II)-promoted activation of hindered dialkyl peroxides has been described, the reported reaction temperatures are often commensurate with peroxide thermolysis .…”

Section: Discussionmentioning

confidence: 99%

Reductive Cleavage of Organic Peroxides by Iron Salts and Thiols

et al. 2018

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Despite the low bond strength of the oxygen–oxygen bond, organic peroxides are often surprisingly resistant to cleavage by nucleophiles and reductants. As a result, achieving decomposition under mild conditions can be challenging. Herein, we explore the reactivity of a selection of peroxides toward thiolates, phenyl selenide, Fe(II) salts, and iron thiolates. Peroxides activated by conjugation, strain, or stereoelectronics are rapidly cleaved at room temperature by thiolate anions, phenylselenide, or Fe(II) salts. Under the same conditions, unhindered dialkyl peroxides are only marginally reactive; hindered peroxides, including triacetone triperoxide and diacetone diperoxide (DADP), are inert. In contrast, all but the most hindered of peroxides are rapidly (<1 min at concentrations down to ∼40 mM) cleaved by mixtures of thiols and iron salts. Our observations suggest the possible intermediacy of strongly reducing complexes that are readily regenerated in the presence of stoichiometric thiolate or hydride. In the case of DADP, an easily prepared explosive of significant societal concern, catalytic amounts of iron and thiol are capable of promoting rapid and complete disproportionation. The availability of inexpensive and readily available catalysts for the mild reductive degradation of all but the most hindered of peroxides could have significant applications for controlled remediation of explosives or unwanted radical initiators.

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“…Nevertheless, Lefebvre et al [38] have demonstrated that home-made TATP is a primary explosive and very sensitive to impact or friction, although the strength of explosion may strongly vary since the quality of the final product is very sensitive to the temperature during its synthesis. TATP is highly volatile and decomposes to form large number of gas phase molecules (entropic explosion) [39,40]. Acetone and ozone are predicted to be the main decomposition products, along with oxygen, methyl acetate, ethane, and carbon dioxide [41].…”

Section: [Insert Figure 2 Here]mentioning

confidence: 99%

Vulnerability of industrial facilities to attacks with improvised explosive devices aimed at triggering domino scenarios

Landucci

Reniers

Cozzani

et al. 2015

Reliability Engineering & System Safety

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Process- and chemical plants may constitute a critical target for a terrorist attack. In the present study, the analysis of industrial accidents induced by intentional acts of interference is carried out focusing on accident chains triggered by attacks with home-made (improvised) explosives. The effects of blast waves caused by improvised explosive devices are compared with those expected from a net equivalent charge of TNT by using a specific methodology for the assessment of stand-off distances. It is demonstrated that a home-made explosive device has a TNT efficiency comprised between 0.2 and 0.5. The model was applied to a case study, demonstrating the potentiality of improvised explosives in causing accident escalation sequences and severe effects on population and assets. The analysis of the case-study also allowed obtaining suggestions for an adequate security management

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Factors Influencing Destruction of Triacetone Triperoxide (TATP)

Abstract: Acid catalyzes the formation of triacetone triperoxide (TATP) from acetone and hydrogen peroxide, but acid also destroys TATP, and, under certain conditions, converts TATP to diacetone diperoxide (DADP

Cited by 18 publications

References 15 publications

Rapid degradation of cyclic peroxides by titanium and antimony chlorides

Rapid degradation of cyclic peroxides by titanium and antimony chlorides

Reductive Cleavage of Organic Peroxides by Iron Salts and Thiols

Vulnerability of industrial facilities to attacks with improvised explosive devices aimed at triggering domino scenarios

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