Acetone peroxide

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Acetone peroxide
Acetone peroxide.svg
Cyclic dimer and trimer examples
Acetone peroxide trimer
Acetone peroxide.jpg
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
Mother of Satan
3D model (JSmol)
E number E929 (glazing agents, ...)
C6H12O4 (dimer)
C9H18O6 (trimer)
C12H24O8 (tetramer)
Molar mass 148.157 g/mol (dimer)
222.24 g/mol (trimer)
Appearance White crystalline solid
Melting point 131.5 to 133 °C (dimer)[1]
91 °C (trimer)
Boiling point 97 to 160 °C (207 to 320 °F; 370 to 433 K)
GHS pictograms The exploding-bomb pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
NFPA 704
Flammability (red): no hazard codeHealth (blue): no hazard codeReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerinSpecial hazards (white): no codeNFPA 704 four-colored diamond
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 0.55–0.8, depends on measure
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

Acetone peroxide is an organic peroxide and a primary high 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 trimer is known as triacetone triperoxide (TATP) or tri-cyclic acetone peroxide (TCAP). The dimer is known as diacetone diperoxide (DADP). 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 if subjected to heat, friction, static electricity, concentrated sulfuric acid, strong UV radiation or shock. As a non-nitrogenous explosive, TATP has historically been more difficult to detect, and it has been used as an explosive in several terrorist attacks since 2001.


Acetone peroxide (specifically, triacetone triperoxide) was discovered in 1895 by Richard Wolffenstein.[2] 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.[3]

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.[4] 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.[5] They found that the trimer could be prepared by adding hydrochloric acid to a chilled mixture of acetone and hydrogen peroxide.[6] 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.[7]

Work on this methodology and on the various products obtained, was further investigated in the mid-20th century by Milas and Golubović.[8]


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 various further monomeric and dimeric forms are possible.[citation needed]

Synthesis of tri-cyclic acetone peroxide.
Probable reactions behind the formation of TATP and DADP

Specifically, two dimers, one cyclic (C6H12O4)[citation needed] and one open chain (C6H14O4)[citation needed], as well as an open chain monomer (C3H8O4),[9] can also be formed; under a particular set of conditions of reagent and acid catalyst concentration, the cyclic trimer is the primary product.[8] A tetrameric form has also been described, under different catalytic conditions.[10] The synthesis of tetrameric aceton peroxide has been disputed.[11][12] Under neutral conditions, the reaction is reported to produce the monomeric organic peroxide.[8]

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 high amounts of conc. sulfuric acid as catalyst or alternatively with 30% H2O2 and massive amounts of HCl as a catalyst.[13]

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, this is the most likely mechanism behind accidental explosions of acetone peroxide that occur during drying on heated surfaces.[14]

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."[15] 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 as an entropic explosion.[15] However, this hypothesis has been challenged as not conforming to actual measurements.[16] 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 2300 K and pressure of 80 kbar.[17] The final energy of detonation is about 2800 kJ/kg (measured in helium) - enough to -briefly- raise the temperature of gaseous products to 2000 °C. Volume of gases at STP is 855 l/kg for TATP and 713 l/kg for DADP (measured in helium).[18]

Detonation of TATP in inert gas gives:

C9H18O6 →1.30 CO2 + 2.44 CO + 2.61 CH4 + 0.63 C2H6 + 0.23CmHm + 0.47 H2 + 0.96 H2O + 0.47C

TATP/DADP, as well as HMTD, belongs to the mercury fulminate group of primary explosives. This means that small, unconfined, samples (less than 2 g) tend to quickly burn (deflagration), while larger and/or properly confined samples detonate. This is sometimes demonstrated in chemistry classes. The experimenter may pour a small amount of acetone peroxide on his/her hand and light it on fire. This is strongly recommended against. The nature of deflagration to detonation transition (DDT) is probabilistic and even extremely small, unconfined samples may immediately detonate! In any case, any direct contact of primary explosive with any part of the body breaks one of the cardinal safety rules for the safe handling of primary explosives!

Detonation velocity of HMTD and TATP
Detonation pressure of TATP as a function of sample density, rough estimate.

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.[10] It's synthesis has been disputed.[12]

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.

Several methods can be used for trace analysis of TATP,[19] including gas chromatography/mass spectrometry (GC/MS),[20][21][22][23][24] high performance liquid chromatography/mass spectrometry (HPLC/MS),[25][26][27][28][29] and HPLC with post-column derivitization.[30]

Acetone peroxide is soluble in toluene, chloroform, acetone, dichloromethane and methanol.[31] Recrystalization of primary explosives may yield large crystals that detonate spontaneously due to internal strain.[32]

Industrial uses[edit]

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 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.[33]

Acetone peroxides are unwanted by-products of some oxidation reactions such as those used in phenol syntheses.[34] Due to their explosive nature, their presence in chemical processes and chemical samples creates potential hazardous situations. Accidental occurrence at illicit MDMA laboratories is possible.[35] Numerous methods are used to reduce their appearance, including shifting pH to more alkaline, adjusting reaction temperature, or adding inhibitors of their production.[34] For example, triacetone peroxide is the major contaminant found in diisopropyl ether as a result of photochemical oxidation in air.[36]


TATP, when fresh, is about as sensitive as an average primary explosive. DADP, when fresh, is slightly less sensitive than the average primary explosive. Older samples may contain larger crystals due to re-sublimation and larger crystals are generally more sensitive. However the experimental evidence behind this effect is contradictory.[37] It is important to note that the variance of friction force between different surfaces (e.g. different kinds of paper) is often greater than the variance between the friction sensitivity of a given pair of primary explosives. This leads to different values for friction sensitivity measured at different laboratories. Wet acetone peroxide is several times less sensitive to friction than dry acetone peroxide yet its impact sensitivity is almost the same as in the case of dry sample. Mixes with synthetic oil like WD-40 are both less impact and friction sensitive than the dry sample. Water mixed with ethanol is even better.[38][39] Sensitivity of mixes can not be (naively) predicted. One can expect, for example, that a mixture of TATP and ammonium nitrate is going to be less sensitive than pure TATP. The opposite is true (at certain ratios) since the sensitivity is affected by complex, mutual crystal interplay and hardness.[40]

Sensitivity of TATP and DADP compared to other primary explosives and PETN.
Sensitivity of wet TATP and DADP to friction and impact.
Sensitivity of wet TATP, DADP and HMTD to friction.


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.[41][42][43][44] It was one of the explosives used by the "shoe bomber" Richard Reid[45][46][44] in his 2001 failed shoe bomb attempt and was used by the suicide bombers in the November 2015 Paris attacks,[47] 2016 Brussels bombings,[48] Manchester Arena bombing, June 2017 Brussels attack,[49] Parsons Green bombing[50] and the Surabaya bombings.[51]

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 1/3 of the brisance of TNT (1.2 g/cm3) measured by the Hess test. The plate dent test gives about 70% of the TNT eq. at the same densities.[52] The ballistic mortar test gives 62% of TNT. The Trauzl lead block test gives above 250 cm3/10g, that is 80% of TNT.[53] This means that TATP is a moderately powerful explosive. A 50 g charge detonated at a 3 m distance will generate a shockwave with an impulse of 9.65 (positive phase) and maximum peak pressure of 18 kPa - 20 kPa is regarder as a threshold for eardrum rapture[54] with about 50 % eardrum rapture rate at 104 kPa.[55] A 1.75 g TATP charge detonated at 4.2 cm will generate 0.396 (40.1 positive shockwave impulse with maximum overpessure of 28 atmospheres (2837 kPa) - that is about the minimum required for immediate amputation of a finger. Injuries that will lead to an amputation are possible at somewhat lower pressures. [56]

One can easily calculate moderately precise lethality distances for the resulting shockwave using Bass or Bowen equation.[57] 1 kg of TATP should produce 50% mortality at a distance of 1.2 m and near 99% mortality at a distance of about 0.9 m. 10 kg of TATP should produce 50% lethality at 3.2 m and 99% mortality at 2.5 m (distance between upper body and the center of explosion, person facing any direction). The lethality distances for a person that is directly facing the explosion are about 20 % higher. A crowded environment reduces these distances by about 1/3. This leads to about 700 g of TATP per 1 fatality for moderately crowded buses and trains from the shockwave effects alone.

Lethality of 10 kg of TATP due to shockwave effects alone. Uncrowded environment. To scale.
The direct blast effects of TATP aren't particullary impressive. Fragments, especially those with high cross-sectional density like 2 g+ steel balls, can be more dangerous. Even small amounts, on the order of 1 - 2 kg, can cause dozens of fatalities via fragmentation, especially when detonated above a large crowd.

The acceleration ability of loose TATP powder (0.3 - 0.5 g/cm3) is rather poor. The volume energy of 0.4 g/cm3 TATP is about 1120 J/cm3, while the same parameter for cast TNT is about 6800 J/cm3. This very roughly translates to typical fragment velocities of 0.5 – 1 km/s for loose 0.4 g/cm3 TATP charges and 1 – 2 km/s for charges made out of cast TNT. See Gourney equations. Such "low" velocity fragments need to have large cross-sectional density to reach vital organs (at least 2 g steel balls). The use of light, very low cross-sectional density fragments has been implicated as one of the factors behind the failure of the Novermber 2015 Paris attackers to generate large numbers of fatalities via the use of TATP suicide vests (only 1 person killed). Stories of mobile phones protecting their owners from fragments are not credible, as a low cross sectional density fragment is unlikely to penetrate the skull - evidenced by the failure to penetrate the phone. Optimized warhead designs employ about 3 kg of fragments per 1 kg of TATP.[58]

TATP, owning to it's low detonation pressure (~ 15 - 40 kbar at common densities) can not be efficiently employed to buckle or cut targets made out of steel - like steel columns. It's effect against concrete and stone is moderate.

TATP is attractive to terrorists because it is easily prepared from readily available retail ingredients, such as hair bleach and nail polish remover.[47] It is also able to evade detection because it is one of the few high explosives that do not contain nitrogen,[59] and can therefore pass undetected through traditional explosive detection scanners designed to detect nitrogenous explosives.[60] Several detection devices for TATP have however now been developed.[61][46]

Legislative measures to limit the sale of concentrated hydrogen peroxide (above 12% conc.) have been made in the EU and in Canada.[62] Pharmacy grade 3 % is still freely available over the counter (OTC) with no buyer identification needed. The resulting acetone peroxide yileds are quite poor with respect to the amount of acid and acetone needed. One would need at least 400 100 ml bottles of 3 % hydrogen peroxide, 12.5 l of acetone and 12.5 l of hydrochloric acid for the production of 1 kg of acetone peroxide making this route highly impractical. Other practical synthetic routes via OTC chemicals are still available but will remain undisclosed for security reasons.

A key disadvantage is its high susceptibility to accidental detonation (and resulting workplace accidents or "own goals" in bomb-making shops), which has led to TATP being referred to as the "Mother of Satan".[63][59] TATP was found in the accidental explosion that preceded the 2017 terrorist attacks in Barcelona and surrounding areas.[64] Complete drying of large amounts of TATP is one of the factors behind these incidents. Large amounts of TATP need no to be thoroughly dried at all, TATP with 15 - 20 % of water by mass is perfectly capable of detonating from a 2 g blasting cap or a 20 g booster made out of dry TATP. On the other hand, TATP with over 25 % of water by mass may not detonate at all even when hit by the explosion of 20 g dry TATP booster and it is highly unlikely that it will detonate when hit by flame in unconfined space. The use of very wet TATP has been implicated as a factor behind the failure of 2017 Parsons Green bombing.

Large scale TATP synthesis is often betrayed by excessive bleach-like or fruity smell. This smell can even penetrate into clothes and hair in amounts that are quite noticeable. Such a person "smells like chemicals". This has been reported in the 2016 Brussels bombings.[65]


TATP is a common source of injury among amateur chemists, particularly finger amputations. There is at least on the order of 3 and 10 recorded amputations in Slovakia and the US respectively, with possibly over 100 cases per year in Canada, Europe and the US combined.[66] Most of these injuries are caused by small amounts of TATP that inadvertently detonate (due to small, unexpected areas of high friction or static electricity sparks) in close proximity of fingers, since small amounts (1 - 3 grams) are generally not powerful enough to amputate fingers from distances larger than 5 – 10 cm.[67] Direct contact between fingers and TATP is to be avoided for this reason. Special, earthened, tools made out of special plastic materials or long wooden rods with cotton wool wrapping at the end are used for manipulation. Standard safety equipment includes ear plugs or ear muffs, face shields, two layers of leather + Kevlar/Dyneema/steel wire gloves, Kevlar sleeves and bullet resistant glass panels. Cavities filled with acetone peroxide tend not to be filled up to the top, the top 10 cm are rather filled with stuffing like cotton wool to create a spot for safe touching. [68]

Accidental detonation of 20 g of TATP. Large piles of TATP suffer from immediate DDT transition. Handling more than 2 g of TATP is a severe breach of the code for handling of primary explosives. Note that the desk has been shattered and the extinguished burner in background.
Filling a blasting cap (or a small firecracker) with TATP requires training, skill, extreme caution and protective equipment like two layers of gloves made out of Kevlar/Dyneema/Leather. A blast mitigtion device is needed.


  1. ^ Federoff, Basil T. et al., Encyclopedia of Explosives and Related Items (Springfield, Virginia: National Technical Information Service, 1960), vol. 1, p. A41.
  2. ^ See:
    • 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".)
    • Wolfenstein R (1895) Deutsches Reichspatent 84,953
    • Matyáš R, Pachman J (2013). Primary Explosives. Berlin: Springer. p. 262. ISBN 978-3-642-28436-6.
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  4. ^ See:
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  6. ^ (Baeyer and Villiger, 1900), p. 859.
  7. ^ (Baeyer and Villiger, 1900), p. 859. From 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 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 is identical to Wolffenstein's, a molecular weight determination of it was likewise made, which led to numbers that are correct for a trimolecular peroxide.)
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