Decomposition of Triacetone Triperoxide Is an Entropic Explosion

Dubnikova, Faina; Kosloff, Ronnie; Almog, Joseph; Zeiri, Yehuda; Boese, Roland; Itzhaky, Harel; Alt, Aaron; Keinan, Ehud

doi:10.1021/ja0464903

Cited by 262 publications

(221 citation statements)

References 34 publications

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“…Properties of the pure material are reported in Table 1 along with standard military explosives for comparison. Literature procedures abound for TATP synthesis, from peer-reviewed journals and the internet, but all are similar [1,[4][5][6][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. Furthermore, an internet search provides a plethora of videos and forums of individuals who candidly show and speak about making TATP.…”

Section: Introductionmentioning

confidence: 99%

Factors Influencing Triacetone Triperoxide (TATP) and Diacetone Diperoxide (DADP) Formation: Part I

Oxley

Smith

Bowden

et al. 2013

Propellants Explo Pyrotec

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Conditions which result in the formation of triacetone triperoxide (TATP) or diacetone diperoxide (DADP) from acetone and hydrogen peroxide (HP) have been studied for the purposes of inhibiting the reaction. Reaction of HP with acetone precipitates either DADP or TATP, but the overall yield and amount of each was found to depend on (1) reaction temperature; (2) the molar ratio of acid to HP/acetone; (3) initial concentrations of reactants, and (4) length of reaction. Controlling molar ratios and concentrations of starting materials was complicated because both sulfuric acid and hydrogen peroxide were aqueous solutions.Temperature exercised great control over the reaction outcome. Holding all molar concentrations constant and raising the temperature from 5 to 25°C showed an increase of DADP over TATP formation and a decrease in overall yield. At 25°C a good yield of TATP was obtained if the HP to acetone ratio was kept between 0.5-to-1 and 2-to-1. At constant temperature and HP-toacetone held at one-to-one ratio, acid-to-HP molar ratios between 0.10:1 and 1.2:1 produced good yield of TATP. Plotting the molality of HP versus that of sulfuric acid revealed regions in which relatively pure DADP or pure TATP could be obtained. In addition to varying reaction conditions, adulterants placed into acetone were tested to inhibit the formation of TATP. 2Because there is much speculation of the relative stability, sensitivity, including solvent wetting of crystals, and performance of DADP and TATP, standard tests (i.e. DSC, drop weight impact, and SSED) were performed.

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Section: Introductionmentioning

confidence: 99%

Factors Influencing Triacetone Triperoxide (TATP) and Diacetone Diperoxide (DADP) Formation: Part I

Oxley

Smith

Bowden

et al. 2013

Propellants Explo Pyrotec

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“…First observed by Fleischmann and coworkers (5), and shown to be a highly enhanced form of Raman spectroscopy by Van Duyne (6), the SERS enhancement can be so great that analytes with femtomolar or lower concentrations can be detected (7), potentially making SERS a sensitive approach to detecting gaseous molecules emanating from explosive devices, toxic airborne compounds, or other atmospheric environmental contaminants (8).…”

Section: Chemical Detection ͉ Nanoparticle Aggregationmentioning

confidence: 99%

Free-surface microfluidic control of surface-enhanced Raman spectroscopy for the optimized detection of airborne molecules

Piorek

Lee²,

Santiago³

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

147

124

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We present a microfluidic technique for sensitive, real-time, optimized detection of airborne water-soluble molecules by surfaceenhanced Raman spectroscopy (SERS). The method is based on a free-surface fluidic device in which a pressure-driven liquid microchannel flow is constrained by surface tension. A colloidal suspension of silver nanoparticles flowing through the microchannel that is open to the atmosphere absorbs gas-phase 4-aminobenzenethiol (4-ABT) from the surrounding environment. As surface ions adsorbed on the colloid nanoparticles are substituted by 4-ABT, the colloid aggregates, forming SERS ''hot spots'' whose concentrations vary predictably along the microchannel flow. 4-ABT confined in these hot spots produces SERS spectra of very great intensity. An aggregation model is used to account quantitatively for the extent of colloid aggregation as determined from the variation of the SERS intensity measured as a function of the streamwise position along the microchannel, which also corresponds to nanoparticle exposure time. This allows us to monitor simultaneously the nanoparticle aggregation process and to determine the location at which the SERS signal is optimized. chemical detection ͉ nanoparticle aggregationA n important trend in modern chemical reaction engineering is the miniaturization of reactors and other devices to the micro and nano scale (1). Such lab-on-a-chip systems, first postulated in 1990, and based on small-scale physics, now complement traditional reaction design approaches (2). In this work, we describe a microfluidic stream in which the spanwise dimension is miniaturized to a sufficiently small size to cause the flowing liquid to be confined solely by surface tension. This architecture allows a small-scale chemical processing device to be fabricated that allows gas-phase or airborne species to enter the flowing microfluidic circuit directly from the ambient environment. Once absorbed, these chemical species can potentially be subjected to further chemical reactions and analysis. Here, we demonstrate the absorption of a gas-phase species at a low partial pressure into a silver colloid flow confined to the microchannel and the subsequent detection of the analyte by surface-enhanced Raman spectroscopy (SERS). In this device, reaction time scales proportionally with distance along the microchannel. This architecture allows the aggregation dynamics to be modeled and understood, making it possible to optimize the SERS signal intensity.SERS spectra contain vibrational information that allows molecular species to be detected and identified (3, 4). First observed by Fleischmann and coworkers (5), and shown to be a highly enhanced form of Raman spectroscopy by Van Duyne (6), the SERS enhancement can be so great that analytes with femtomolar or lower concentrations can be detected (7), potentially making SERS a sensitive approach to detecting gaseous molecules emanating from explosive devices, toxic airborne compounds, or other atmospheric environmental contaminants (8).The theory of SERS i...

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“…Additionally, different results related with new synthetic methods or alternative techniques that involve greater yields of peroxide compound in a shorter preparation time were reported. [1][2][3][4][5] Peroxides are shock sensitive and their overall decompositions are exothermic so that special handling precautions must be taken. Depending on the molecular group linked on the peroxide ring, their decomposition may be explosive in different degrees.…”

Section: Introductionmentioning

confidence: 99%

“…6 In this sense, triacetone triperoxide (3,3,6,6,9,9-hexamethyl--1,2,4,5,7,8-hexaoxacyclonane, TATP) is one of the most sensitive explosives known with a power close to that of TNT (a 10 g sample gave 250 cm 3 expansions in the Trauzl test as compared to 300 cm 3 for TNT), a property that allows its employment as both primary explosive and main charge. 4,5 Primary explosives form a group of compounds that are considered to be highly sensitive to some mechanical stimuli such as impact, friction, stab, heat, static electricity, flame, etc. Sensitivity of explosives to friction is one of the fundamental parameters to be considered, 5 attending to safety manipulation of this type of compounds.…”

Section: Introductionmentioning

confidence: 99%

Thermal decomposition reaction in ethanol solution of deuterated acetone cyclic diperoxide and acetone diperoxide. Secondary inverse isotopic effect

Nesprías¹,

Eyler²,

Cañizo³

et al. 2017

Quim. Nova

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The characterization by mass spectrometry and the kinetic study of the thermal decomposition reaction of deuterated acetone diperoxide (dACDP) was studied in ethanol in the 140-165 °C temperature range. The comparison with the non deuterated species (ACDP) was also made. The kinetic behavior observed for both compounds follows a pseudo first order kinetic law up to at least 86 % peroxide conversions. It could be observed that under the established experimental conditions, the dACDP decomposes ca. 1.2 times faster than the ACDP. The activation parameters were calculated for both peroxides and allowed to postulate a single process initial step, the unimolecular thermal decomposition through the O-O bond cleavage to form an intermediate biradical. The products of the acetone derived peroxides thermal decomposition support a radical-based decomposition mechanism. The changes in kinetic parameters between dACDP and ACDP were justified attending to differences in ring substituents sizes. A secondary inverse kinetic isotope effect is observed (k H /k D <1).

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Decomposition of Triacetone Triperoxide Is an Entropic Explosion

Cited by 262 publications

References 34 publications

Factors Influencing Triacetone Triperoxide (TATP) and Diacetone Diperoxide (DADP) Formation: Part I

Factors Influencing Triacetone Triperoxide (TATP) and Diacetone Diperoxide (DADP) Formation: Part I

Free-surface microfluidic control of surface-enhanced Raman spectroscopy for the optimized detection of airborne molecules

Thermal decomposition reaction in ethanol solution of deuterated acetone cyclic diperoxide and acetone diperoxide. Secondary inverse isotopic effect

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