Triacetone-triperoxide

The nine-membered ring of the TATP molecule forms a twist boat chair conformation (Fig. 10.5). The crystal packing (Fig. 10.6) consists of stacks around the molecular threefold axis with no apparent C—H --0 interactions [13]. Theoretical studies of other possible conformations have been published by Yavari et al. [41]. 

Triacetone triperoxide forms colorless crystals which appear white when finely ground (Fig. 10.7). Its crystal density is 1.272 g cm (X-ray) [13, 42] melting point is reported in the range 95-98.8 °C and decomposition above 150-160 °C [17, 39, 43-46]. The heat of formation of TATP is 90.8 kJ mol [47]. Triacetone triperoxide is nonhygroscopic and very volatile [17]. 

It spontaneously recrystallizes at room or even at subambient temperatures (0 °C) into nicely formed cubes as can be seen in Fig. 10.8. The detail of the surface of the crystal during recrystallization is presented in Fig. 10.9. The storage temperature and the type of acid used for TATP preparation both have significant impacts on the rate of TATP recrystallization. The process is much faster for TATP 

The type of acid used during TATP preparation has a significant impact on its long-term stability. TATP prepared using sulfuric or perchloric acid decomposes and lose weight more quickly than pure TATP (by recrystalhzation). The loss of weight of TATP prepared using hydrochloric or nitric acid is much slower and about the same as observed for pure TATP and is related to sublimation rather than decomposition [48]. 

Reany et al. recently published that TATP forms at least six different polymorphic crystals. The type of acid used as a catalyst for TATP preparation and the solvent used for TATP crystallization have an impact on the crystal morphology of the product. 

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The requirement for an explosive train, that is, a primary explosive to initiate the secondary explosive, is a safety feature. In the past, people wishing to illegally use explosives usually had to steal the detonators (e.g., Timothy McVey). Consequently, the effective control of access to detonators has been widely regarded as a key pubhc safety measure by many governments and law enforcement agencies. However, recently, triacetone triperoxide (TATP) has been used as the primary explosive (e.g., Richard Reid s shoe bomb) and TATP is readily, although hazardously, synthesized from acetone, hydrogen peroxide, and acid. 

AN, ammonium nitrate HMTD, hexamethylene triperoxide diamine HMX, C4H8N8O8 NG, nitroglycerin PETN, pentaerythritol tetranitrate RDX, CsHgNgOg TATP, triacetone triperoxide ... 

J.C. Oxley, J.L. Smith, J. Moran, K. Shinde, Determination of the vapour density of triacetone triperoxide (TATP) using a gas chromatography headspace technique . Propellants Explos. Pyrotech. 127—130. 

Triacetone triperoxide (TATP) is a powerful explosive manufactured in clandestine laboratories and used by terrorists. As TATP subHmes easily, analysis was performed by SPME trapping of its vapor, using polydimethylsiloxane/divinyl benzene (PDMS/DVB) fiber, followed by desorption into a GC/MS injector [10]. Figure 6 shows the TIC, mass chromatogram and the El mass spectmm of headspace from a debris sample containing TATP [11]. The El mass spectmm contains a molecular ion at m/z 222 and several fragment ions. In the chemical ionization mass spectmm of TATP [12], the m or ions were at m/z 223 (100%), 222 (20%), 133 (20%), 117 (40%), 115 (20%), 103 (75%) and 100 (50%). 

Figure 6 TIC, mass chromatogram and El mass spectrum of a debris sample containing triacetone triperoxide (TATP) (Reproduced from T. Tamiri et al., Proc. 6th Int. Symp. on Analysis and Detection of Explosives, Prague, Czech Republic, 1998. With permission).

Figure 13 LC/MS/MS mass spectrum of triacetone triperoxide (TATP) [Reproduced from L. Widmer et al.. Analyst, 127 (2002) 1627. With permission from the Royal Society of Chemistry].

G.A. Buttigieg, A.K. Knight, S. Denson, C. Pommier and M.B. Denton, Characterization of the explosive triacetone triperoxide and detection by ion mobility spectrometry. Forensic Science International 135(1) (2003) 53-59. 

Some ketone-derived peroxides have explosive properties, of which the most interesting are obtained from acetone. Four acetone-derived peroxides have been synthesized. Acetone peroxide dimer (48) is obtained in 94 % yield by treating acetone with a slight excess of 86 % hydrogen peroxide in acetonitrile in the presence of concentrated sulfuric acid at subambient temperature. The reaction of acetone with potassium persulfate in dilute sulfuric acid also yields acetone peroxide dimer (48). Acetone peroxide trimer (49), also known as triacetone triperoxide (TATP), has been obtained as a by-product of these reactions or by the addition of... 

These are common abbreviations for the following TNT 2,4,6-trinitrotoluene AN ammonium nitrate PETN pentaerythritol tetranitrate HMX octahydro-l,3,5,7,-tetranitro-l,3,4,5-tetrazocine RDX hexahydro-l,3,5-trinitro-s-triazine HMTD hexamethylene triperoxide diamine TATP triacetone triperoxide. 

Oxley, J. C., J. L. Smith, and H. Chen. Decomposition of multi-peroxidic compound Triacetone triperoxides (TATP). Propellants, Explosives Pyrotechnics 27, 209-216 (2002). 

Two forms of acetone peroxides are known to exist a dimer called diacetone diperoxide (DADP) and a trimer called triacetone triperoxide (TATP). Figure 3.4 displays the chemical structures of each. 

Peroxide explosives are potent explosives that can be made starting from common and easy to obtain raw materials. The analysis of triacetone triperoxide (TATP) and hexamethylenetriper-oxidediamine (HMTD) was successfully carried out by HPLC-APCI-MS in a powder sample as well as in post-blast extracts originating from a forensic case [134]. After RP separation on a C18 column using a methanohwater (75 25 v/v) mobile phase containing ammonium acetate (2.5mM) at a 0.4mL/min flow rate, detection was carried out in positive ion mode. MS-MS analysis of [TATPh-NH4]+ and [HMTD - H]+ as precursor ions was necessary in order to achieve the required sensitivity in the analysis of postblast extracts (LOD 0.8 and 0.08 ng on column, respectively). 

Inspired by the effective post-column photochemical conversion of hydroperoxides and peroxides to H2O2 just described, a method was developed for trace analysis of peroxide explosives, such as triacetone triperoxide (251) and hexamethylene triperoxide diamine (252). These are powerful explosives with no commercial or military applications because... 

Transport of dangerous goods (TDG), 745-6 Trauma, plasma oxidation level, 631 Triacetone triperoxide explosive, 707-8 Triacylglycerides, mass spectrometry, 689 Triarylgermyl hydroperoxide, formation, 822 Triarylphosphine, hydroperoxide determination, 679... 

Triamino-2,4,6-trinitrobenzene Triacetone triperoxide Triacetone triperoxide 4,4,4-Trinitrobutry aldehyde Trichlorotrinitrobenzene Tetranitro aniline Tetranitro aniline Isocyanogen tetraazide... 

Acetoneperoxide, Trimeric or Triacetone Triperoxide (Acetonetriperoxide, Trimeric Acetoneperoxide, Acetonetrimer Peroxide, Cyclotri ace tone Peroxide, or Tricycloacetone Peroxide)(CalIed by Wolfenstein Tricyclo-aceton-superoxyd and by Rohrlich and Sauer-milch Trizycloazetonperoxyd),... 

Acetone peroxides 1 A41—A45 diacetone diperoxide 1 A41—A42 triacetone triperoxide 1 A42—A45... 

Triacetin. See under Acetins A31-R Triacetone Triperoxide. See under Acetone Peroxides A42-R Trialkyls of Aluminum A144-R... 

Both X-ray crystallography and electronic structure calculations using the cc-pVDZ basis set at the DFT B3LYP level have been employed to study the explosive properties of triacetone triperoxide (TATP) and diacetone diperoxide (DADP).32 The thermal decomposition pathway of TATP has been investigated by a series of calculations that identified transition states, intermediates, and the final products. Calculations predict that the explosion of TATP is not a thermochemically highly favoured event. It rather involves entropy burst, which is the result of formation of one ozone and three acetone molecules from every molecule of TATP in the solid state. 

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