Acetone peroxide

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Acetone peroxide
Acetone peroxide.svg
Cyclic dimer and trimer examples
Acetone peroxide trimer Acetone-peroxide-trimer-from-xtal-2009-3D-balls.png
Acetone peroxide trimer
Acetone peroxide.jpg
Names
IUPAC names
3,3-Dimethyl-1,2-dioxacyclopropane (monomer)
3,3,6,6-Tetramethyl-1,2,4,5-tetraoxane (dimer)
3,3,6,6,9,9-Hexamethyl-1,2,4,5,7,8-hexaoxacyclononane (trimer)
3,3,6,6,9,9,12,12-Octamethyl-1,2,4,5,7,8,10,11-octaoxacyclododecane (tetramer)
Other names
Triacetone triperoxide
Peroxyacetone
Mother of Satan
Identifiers
3D model (JSmol)
ChemSpider
E number E929 (glazing agents, ...)
PubChem CID
UNII
  • InChI=1S/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3 Yes check.svgY
    Key: ZTLXICJMNFREPA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3
    Key: ZTLXICJMNFREPA-UHFFFAOYAS
  • dimer:CC1(C)OOC(C)(C)OO1
  • trimer:CC1(C)OOC(C)(C)OOC(C)(C)OO1
Properties
C6H12O4 (dimer)
C9H18O6 (trimer)
C12H24O8 (tetramer)
Molar mass 148.157 g/mol (dimer)
222.24 g/mol (trimer)
296.296 g/mol (tetramer) [1]
AppearanceWhite crystalline solid
Melting point 131.5 to 133 °C (dimer) [2]
91 °C (trimer)
Boiling point 97 to 160 °C (207 to 320 °F; 370 to 433 K)
Insoluble
Hazards
GHS labelling:
GHS-pictogram-explos.svg GHS-pictogram-exclam.svg
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
1
4
4
Explosive data
Shock sensitivity High/High when wet
Friction sensitivity High/moderate when wet
Detonation velocity 5300 m/s at maximum density (1.18 g/cm3), about 2500–3000 m/s near 0.5 g/cm3
17,384 ft/s
3.29 miles per second
RE factor 0.80
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Acetone peroxide ( /æsəˈtəʊnpɛrˈɒksaɪd/ ⓘ also called APEX and mother of Satan [3] [4] ) is an organic peroxide and a primary explosive. It is produced by the reaction of acetone and hydrogen peroxide to yield a mixture of linear monomer and cyclic dimer, trimer, and tetramer forms. The monomer is dimethyldioxirane. 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 bleach-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 shock. 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 terrorist bomb attacks since 2001.

History

Acetone peroxide (specifically, triacetone triperoxide) was discovered in 1895 by the German chemist Richard Wolffenstein. [5] [6] [7] Wolffenstein combined acetone and hydrogen peroxide, 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 97 °C (207 °F). [8]

In 1899, Adolf von Baeyer and Victor Villiger described the first synthesis of the dimer and described use of acids for the synthesis of both peroxides. [9] [10] [11] [12] [13] Baeyer and Villiger prepared the dimer by combining potassium persulfate in diethyl ether with acetone, under cooling. After separating the ether layer, the product was purified and found to melt at 132–133 °C (270–271 °F). [14] They found that the trimer could be prepared by adding hydrochloric acid to a chilled mixture of acetone and hydrogen peroxide. [15] By using the depression of freezing points 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. [16]

Work on this methodology and on the various products obtained, was further investigated in the mid-20th century by Milas and Golubović. [17]

Chemistry

The chemical name acetone peroxide is most commonly used to refer to the cyclic trimer, the product of a reaction between two precursors, hydrogen peroxide and acetone, in an acid-catalyzed nucleophilic addition, although monomeric and dimeric forms are also possible. [18] [19]

Synthesis of tri-cyclic acetone peroxide. Acetone Peroxide Synthesis V.2.svg
Synthesis of tri-cyclic acetone peroxide.

Specifically, two dimers, one cyclic (C6H12O4) and one open chain (C6H14O4), as well as an open dihydroperoxide monomer (C3H8O4), [20] can also be formed; under a particular set of conditions of reagent and acid catalyst concentration, the cyclic trimer is the primary product. [17] A tetrameric form has also been described, under different catalytic conditions, however. [21] the synthesis of tetrameric acetone peroxide has been disputed. [22] [23] Under neutral conditions, the reaction is reported to produce the monomeric organic peroxide. [17]

The most common route for nearly pure TATP is H2O2/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% H2O2 using large amounts of concentrated sulfuric acid as catalyst or alternatively with 30% H2O2 and massive amounts of HCl as a catalyst. [23]

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 50 °C (122 °F). This is the most likely mechanism behind accidental explosions of acetone peroxide that occur during drying on heated surfaces. [24]

Triacetone triperoxide forms in 2-propanol upon standing for long periods of time in the presence of air. [25]

Tetrameric acetone peroxide Tetrameric Acetone Peroxide 01.JPG
Tetrameric acetone peroxide

Organic peroxides in general are sensitive, dangerous explosives, and all forms of acetone peroxide are sensitive to initiation.[ citation needed ] TATP decomposes explosively; examination of the explosive decomposition of TATP at the very edge of detonation front predicts "formation of acetone and ozone as the main decomposition products and not the intuitively expected oxidation products." [26] 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 entropic explosion. [26] However, this hypothesis has been challenged as not conforming to actual measurements. [27] 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  ps after the initial reaction - within about a micron of the detonation wave. Detonating crystals of TATP ultimately reach temperature of 2,300 K (2,030 °C; 3,680 °F) and pressure of 80 kbar. [28] The final energy of detonation is about 2800 kJ/kg (measured in helium), enough to briefly raise the temperature of gaseous products to 2,000 °C (3,630 °F). Volume of gases at STP is 855 L/kg for TATP and 713 L/kg for DADP (measured in helium). [27]

The tetrameric form of acetone peroxide, prepared under neutral conditions using a tin catalyst in the presence of a chelator or general inhibitor of radical chemistry, is reported to be more chemically stable, although still a very dangerous primary explosive. [21] Its synthesis has been disputed. [23]

Crystal deposits of sublimed TATP. Sublimed TATP.jpg
Crystal deposits of sublimed TATP.

Both TATP and DADP are prone to loss of mass via sublimation. DADP has lower molecular weight and higher vapor pressure. 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 Ostwald ripening.

Several methods can be used for trace analysis of TATP, [29] including gas chromatography/mass spectrometry (GC/MS), [30] [31] [32] [33] [34] high performance liquid chromatography/mass spectrometry (HPLC/MS), [35] [36] [37] [38] [39] and HPLC with post-column derivitization. [40]

Acetone peroxide is soluble in toluene, chloroform, acetone, dichloromethane and methanol. [41] Recrystalization of primary explosives may yield large crystals that detonate spontaneously due to internal strain. [42]

Industrial uses

Ketone peroxides, including acetone peroxide and methyl ethyl ketone peroxide, find application as initiators for polymerization reactions, e.g., silicone or polyester resins, in the making of fiberglass-reinforced composites.[ citation needed ] 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 ]

Acetone peroxide is used as a flour bleaching agent to bleach and "mature" flour. [43]

Acetone peroxides are unwanted by-products of some oxidation reactions such as those used in phenol syntheses. [44] 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 diisopropyl ether as a result of photochemical oxidation in air. [45] Accidental occurrence at illicit MDMA laboratories is possible. [46]

Numerous methods are used to reduce their appearance, including shifting pH to more alkaline, adjusting reaction temperature, or adding inhibitors of their production. [44] [ additional citation(s) needed ]

Use in improvised explosive devices

TATP has been used in bomb and suicide attacks and in improvised explosive devices, including the London bombings on 7 July 2005, where four suicide bombers killed 52 people and injured more than 700. [47] [48] [49] [50] It was one of the explosives used by the "shoe bomber" Richard Reid [51] [52] [50] in his 2001 failed shoe bomb attempt and was used by the suicide bombers in the November 2015 Paris attacks, [53] 2016 Brussels bombings, [54] Manchester Arena bombing, June 2017 Brussels attack, [55] Parsons Green bombing, [56] the Surabaya bombings, [57] and the 2019 Sri Lanka Easter bombings. [58] [59] Hong Kong police claim to have found 2 kg (4.4 lb) of TATP among weapons and protest materials in July 2019, when mass protests were taking place against a proposed law allowing extradition to mainland China. [60]

TATP shockwave overpressure is 70% of that for TNT, the positive phase impulse is 55% of the TNT equivalent. TATP at 0.4 g/cm3 has about one-third of the brisance of TNT (1.2 g/cm3) measured by the Hess test. [61]

TATP is attractive to terrorists because it is easily prepared from readily available retail ingredients, such as hair bleach and nail polish remover. [53] It was also able to evade detection because it is one of the few high explosives that do not contain nitrogen, [62] and could therefore pass undetected through standard explosive detection scanners, which were hitherto designed to detect nitrogenous explosives. [63] By 2016, explosives detectors had been modified to be able to detect TATP, and new types were developed. [64] [65]

Legislative measures to limit the sale of hydrogen peroxide concentrated to 12% or higher have been made in the European Union. [66]

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". [65] [62] TATP was found in the accidental explosion that preceded the 2017 terrorist attacks in Barcelona and surrounding areas. [67]

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 2016 Brussels bombings. [68]

Related Research Articles

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Pentaerythritol tetranitrate</span> Explosive chemical compound

Pentaerythritol tetranitrate (PETN), also known as PENT, pentyl, PENTA, TEN, corpent, or penthrite, is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66. When mixed with a plasticizer, PETN forms a plastic explosive. Along with RDX it is the main ingredient of Semtex and C4.

<span class="mw-page-title-main">Cumene process</span> Industrial process

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), and independently by Heinrich Hock in 1944.

<span class="mw-page-title-main">Sodium percarbonate</span> Chemical compound

Sodium percarbonate, or sodium carbonate peroxide is a chemical substance with formula Na
2H
3CO
6. It is an adduct of sodium carbonate and hydrogen peroxide whose formula is more properly written as 2 Na
2CO
3 · 3 H
2O
2. It is a colorless, crystalline, hygroscopic and water-soluble solid. It is sometimes abbreviated as SPC. It contains 32.5% by weight of hydrogen peroxide.

Methyl ethyl ketone peroxide (MEKP) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.

<span class="mw-page-title-main">Hydrogen peroxide - urea</span> Chemical compound

Hydrogen peroxide - urea is a white crystalline solid chemical compound composed of equal amounts of hydrogen peroxide and urea. It contains solid and water-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an oxidizing agent. Often called carbamide peroxide in dentistry, it is used as a source of hydrogen peroxide when dissolved in water for bleaching, disinfection and oxidation.

An entropic explosion is an explosion in which the reactants undergo a large change in volume without releasing a large amount of heat. The chemical decomposition of triacetone triperoxide (TATP) may be an example of an entropic explosion. It is not a thermochemically highly favored event because little energy is generated in chemical bond formation in reaction products, but rather involves an entropy burst, which is the result of formation of one ozone and three acetone gas phase molecules from every molecule of TATP in the solid state.

<span class="mw-page-title-main">Hexafluoro-2-propanol</span> Chemical compound

Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF3)2CHOH. This fluoroalcohol finds use as solvent in organic chemistry. Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index. It is a colorless, volatile liquid with a pungent odor.

<span class="mw-page-title-main">Hexamethylene triperoxide diamine</span> Chemical compound

Hexamethylene triperoxide diamine (HMTD) is a high explosive organic compound. HMTD is an organic peroxide, a heterocyclic compound with a cage-like structure. It is a primary explosive. It has been considered as an initiating explosive for blasting caps in the early part of 20th century, mostly because of its high initiating power and its inexpensive production. As such, it was quickly taken up as a primary explosive in mining applications. However, it has since been superseded by more (chemically) stable compounds such as dextrinated lead azide and DDNP. HMTD is widely used in amateur-made blasting caps.

The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899.

<span class="mw-page-title-main">2005 University of Oklahoma bombing</span> Bombing near Oklahoma Memorial Stadium

The 2005 University of Oklahoma bombing occurred on October 1, 2005 at approximately 7:30 p.m. CDT, when a bomb went off near the George Lynn Cross Hall on Van Vleet Oval on the University of Oklahoma (OU) main campus. The blast took place less than 200 yards west of Oklahoma Memorial Stadium, where 84,501 spectators were attending a football game. The bomber, OU student Joel "Joe" Henry Hinrichs III, was killed in the explosion; no one else was killed.

Organoselenium chemistry is the science exploring the properties and reactivity of organoselenium compounds, chemical compounds containing carbon-to-selenium chemical bonds. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected. Organoselenium compounds are found at trace levels in ambient waters, soils and sediments.

<span class="mw-page-title-main">Azine</span> Chemical compound

Azines are a functional class of organic compounds with the connectivity RR'C=N-N=CRR'. These compounds are the product of the condensation of hydrazine with ketones and aldehydes, although in practice they are often made by alternative routes. Ketazines are azines derived from ketones. For example, acetone azine is the simplest ketazine. Aldazines are azines derived from aldehydes.

<span class="mw-page-title-main">Dakin oxidation</span> Organic redox reaction that converts hydroxyphenyl aldehydes or ketones into benzenediols

The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H2O2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.

<span class="mw-page-title-main">Erythritol tetranitrate</span> Chemical compound

Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact.

<span class="mw-page-title-main">Ammonium formate</span> Chemical compound

Ammonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.

<span class="mw-page-title-main">Seleninic acid</span> Class of chemical compounds

A seleninic acid is an organoselenium compound and an oxoacid with the general formula RSeO2H, where R ≠ H. Its structure is R−Se(=O)−OH. It is a member of the family of organoselenium oxoacids, which also includes selenenic acids and selenonic acids, which are R−Se−OH and R−Se(=O)2−OH, respectively. The parent member of this family of compounds is methaneseleninic acid, also known as methylseleninic acid or "MSA".

<span class="mw-page-title-main">Alkenyl peroxides</span> Organic compounds of the form R2C=C(R)OOR

In organic chemistry, alkenyl peroxides are organic peroxides bearing an alkene residue directly at the peroxide group, resulting in the general formula R2C=C(R)OOR. They have very weak O-O bonds and are thus generally unstable compounds.

<span class="mw-page-title-main">Trifluoroperacetic acid</span> Chemical compound

Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3COOOH. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.

<span class="mw-page-title-main">Bis(trimethylsilyl)peroxide</span> Chemical compound

Bis(trimethylsilyl)peroxide (sometimes abbreviated as BTSP) is an organosilicon compound with the formula ((CH3)3SiO)2. It is a colorless liquid that is soluble in organic solvents so long as they lack acidic groups. The compound represents an aprotic analogue of hydrogen peroxide and as such it is used for certain sensitive organic oxidations. Upon treatment with organolithium compounds, it affords the silyl ether.

References

  1. ↑ "Molar mass C12H24O8".
  2. ↑ Federoff, Basil T. et al., Encyclopedia of Explosives and Related Items (Springfield, Virginia: National Technical Information Service, 1960), vol. 1, p. A41.
  3. ↑ Berezow, Alex (14 November 2018). "TATP: The Chemistry of 'Mother of Satan' Explosive". American Council on Science and Health.
  4. ↑ Swartz, Anna (24 March 2016). "What Is 'Mother of Satan'? What You Should Know About Explosive Used in Brussels Attacks". Yahoo News.
  5. ↑ Wolffenstein R (1895). "Über die Einwirkung von Wasserstoffsuperoxyd auf Aceton und Mesityloxyd" [On the effect of hydrogen peroxide on acetone and mesityl oxide]. Berichte der Deutschen Chemischen Gesellschaft (in German). 28 (2): 2265–2269. 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: [diagram of proposed molecular structure of the trimer of acetone peroxide] . 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 [one] than corresponded to its simple empirical formula. … Thus [the result of the molecular weight determination showed that] there was present a tri-molecular acetone peroxide, which can arise from the monomer by the bonds between each pair of oxygen atoms [on one molecule of acetone peroxide] breaking and serving as links to the oxygen atoms of a neighboring molecule. One thus arrives at the following structural formula: [diagram of proposed molecular structure of the trimer of acetone peroxide] . This strange ring-shaped compound shall be named "tri-cycloacetone peroxide".)
  6. ↑ Wolfenstein R (1895) Deutsches Reichspatent 84,953
  7. ↑ Matyáš R, Pachman J (2013). Primary Explosives. Berlin: Springer. p. 262. ISBN   978-3-642-28436-6.
  8. ↑ Wolffenstein 1895, p. 2266.
  9. ↑ Baeyer, Adolf; Villiger, Victor (1899). "Einwirkung des Caro'schen Reagens auf Ketone" [Effect of Caro's reagent on ketones [part 1]]. Berichte der Deutschen Chemischen Gesellschaft. 32 (3): 3625–3633. doi:10.1002/cber.189903203151. see p. 3632.
  10. ↑ Baeyer A, Villiger V (1900a). "Über die Einwirkung des Caro'schen Reagens auf Ketone" [On the effect of Caro's reagent on ketones [part 3]]. Berichte der Deutschen Chemischen Gesellschaft. 33 (1): 858–864. doi:10.1002/cber.190003301153.
  11. ↑ Baeyer A, Villiger V (1900b). "Über die Nomenclatur der Superoxyde und die Superoxyde der Aldehyde" [On the nomenclature of peroxides and the peroxide of aldehydes](PDF). Berichte der Deutschen Chemischen Gesellschaft. 33 (2): 2479–2487. doi:10.1002/cber.190003302185.
  12. ↑ Federoff, Basil T. et al., Encyclopedia of Explosives and Related Items (Springfield, Virginia: National Technical Information Service, 1960), vol. 1, p. A41.
  13. ↑ Matyáš, Robert and Pachman, Jirí, ed.s, Primary Explosives (Berlin, Germany: Springer, 2013), p. 257.
  14. ↑ Baeyer & Villiger 1899, p. 3632.
  15. ↑ Baeyer & Villiger 1900a, p. 859.
  16. ↑ Baeyer & Villiger 1900a , p. 859"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." [The peroxide that was prepared with Caro's reagent and that melted at 132–133 °C (270–271 °F) gave – according to a determination of molecular weight via the freezing point method – results which show that it is dimolecular. In order to see whether the peroxide that was prepared with hydrochloric acid and that has a melting point of 90–94 °C (194–201 °F) is identical to Wolffenstein's, its molecular weight was likewise determined, which led to values that are correct for a trimolecular peroxide.]
  17. 1 2 3 Milas NA, Golubović A (1959). "Studies in Organic Peroxides. XXVI. Organic Peroxides Derived from Acetone and Hydrogen Peroxide". Journal of the American Chemical Society . 81 (24): 6461–6462. doi:10.1021/ja01533a033.
  18. ↑ Fukuzumi, Kazuo; Miyakawa, Takero; Morohira, Hidenori (1965). "Monomeric dihydroperoxide concentrates from autoxidized methyl docosahexaenoate". Journal of the American Oil Chemists' Society. 42 (8): 717–720. doi:10.1007/BF02540046. ISSN   0003-021X.
  19. ↑ "2013 Annual Report from the Center of Excellence for Explosive Detection, Mitigation and Response in the Department of Homeland Security" (PDF). 2013. Retrieved 17 February 2024.
  20. ↑ This is not the DMDO monomer referred to in the Chembox, but rather the open chain, dihydro monomer described by Milas & Goluboviç, op. cit.
  21. 1 2 Jiang H, Chu G, Gong H, Qiao Q (1999). "Tin Chloride Catalysed Oxidation of Acetone with Hydrogen Peroxide to Tetrameric Acetone Peroxide". Journal of Chemical Research. 28 (4): 288–289. doi:10.1039/a809955c. S2CID   95733839.
  22. ↑ Primary Explosives - Robert Matyáš, Jiří Pachman (auth.), p.275
  23. 1 2 3 Matyáš, R.; Pachman, J. (8 February 2010). "Study of TATP: Influence of reaction conditions on product composition" . Propellants, Explosives, Pyrotechnics. 35 (1): 31–37. doi:10.1002/prep.200800044 . Retrieved 30 August 2021.
  24. ↑ Matyas R, Pachman J (1 July 2007). "Thermal stability of triacetone triperoxide". Science and Technology of Energetic Materials. 68: 111–116.
  25. ↑ Pye, Cory (10 June 2020). "Chemical Safety: TATP Formation in 2-Propanol". ACS Chemical Health & Safety. 27 (5): 279. doi:10.1021/acs.chas.0c00061. S2CID   225762474.
  26. 1 2 Dubnikova, Faina; Kosloff, Ronnie; Almog, Joseph; Zeiri, Yehuda; Boese, Roland; Itzhaky, Harel; Alt, Aaron; Keinan, Ehud (2005). "Decomposition of Triacetone Triperoxide is an Entropic Explosion". Journal of the American Chemical Society. 127 (4): 1146–1159. doi:10.1021/ja0464903. PMID   15669854.
  27. 1 2 Sinditskii VP, Koltsov VI, Egorshev, VY, Patrikeev DI, Dorofeeva OV (2014). "Thermochemistry of cyclic acetone peroxides". Thermochimica Acta. 585: 10–15. doi:10.1016/j.tca.2014.03.046.
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  66. ↑ "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".
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