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 code Health (blue): no hazard code Reactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerin Special 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 YesYN ?)
Infobox references

Acetone peroxide is an organic peroxide and a primary high explosive. It is produced by the oxidation of acetone 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] Under neutral conditions, the reaction is reported to produce the monomeric organic peroxide.[8]

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.[11]

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 unstability. In fact, the trapped sulfuric acid can induce detonation at temperatures as low as 50°C, this is the most likely mechanism behid accidental explosions of acetone peroxide that occur during drying on heated surfaces.[12]

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."[13] 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.[13] However, this hypothesis has been challenged as not conforming to actual measurements.[14] The claim of entropic explosion has been tied 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.[15] 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 nad 713 l/kg for DADP (measured in helium).[16]

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 strongy recommended against. The nature of deflagration to detonation transition (DDT) is probabilistic and even extremely small, unconfined samples may immediately detonate! At 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]

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,[17] including gas chromatography/mass spectrometry (GC/MS),[18][19][20][21][22] high performance liquid chromatography/mass spectrometry (HPLC/MS),[23][24][25][26][27] and HPLC with post-column derivitization.[28]

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.[29]

Acetone peroxides are unwanted by-products of some oxidation reactions such as those used in phenol syntheses.[30] 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.[31] Numerous methods are used to reduce their appearance, including shifting pH to more alkaline, adjusting reaction temperature, or adding inhibitors of their production.[30] For example, triacetone peroxide is the major contaminant found in diisopropyl ether as a result of photochemical oxidation in air.[32]


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.[33] 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 it's 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.[34] [35]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.[36]

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.

Use in improvised explosive devices[edit]

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.[37][38][39][40] It was one of the explosives used by the "shoe bomber" Richard Reid[41][42][40] in his 2001 failed shoe bomb attempt and was used by the suicide bombers in the November 2015 Paris attacks,[43] 2016 Brussels bombings,[44] Manchester Arena bombing, June 2017 Brussels attack[45], Parsons Green bombing[46] and the Surabaya bombings.[47]

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.[48] The ballistic mortar test gives 62 % of TNT. The Trauzl lead block test gives above 250 cm3/10g, that is 80 % of TNT.[49] This means that TATP is a moderately powerful explosive.

One can easily calculate moderately precise lethality distances for the resulting shockwave using Bass or Bowen equation.[50] 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). A crowded enviroment 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 enviroment. To scale.

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.

TATP is attractive to terrorists because it is easily prepared from readily available retail ingredients, such as hair bleach and nail polish remover.[43] It is also able to evade detection because it is one of the few high explosives that do not contain nitrogen[51]—and can therefore pass undetected through traditional explosive detection scanners designed to detect nitrogenous explosives.[52] Several detection devices for TATP have however now been developed.[53][42]

Legislative measures to limit the sale of concentrated hydrogen peroxide (above 12 % conc.) have been made in the EU and in Canada.[54]

A key disadvantage is its high susceptibility to accidental detonation (and resulting "workplace accidents" in bomb-making shops), which has led to TATP being referred to as the "Mother of Satan."[55][51] TATP was found in the accidental explosion that preceded the 2017 terrorist attacks in Barcelona and surrounding areas.[56]

Large scale TATP synthesis is often betryed 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 2016 Brussels bombings and in 2018 Beaver Dam incident. [57]


TATP is a common source of injury among amateur chemists, particularly finger amputations. There is on the order of 100 amputations in the US and EU each year, with many such inexperienced chemists visiting this page just prior the accident.[58] 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 (grams) are generally not powerful enough to amputate fingers from distances larger than 5 - 10 cm.[59] Experienced amateurs handle TATP in such a manner as to avoid any close contact between fingers and the explosive itself, from synthesis to final detonation. Such measures, for example, include using multiple filter papers during the filtration step that are exchanged as not to have more than 0.2 g of TATP on a single filter paper, pre-bent papers with cotton wrapped wooden rods for manipulation and blast mitigation devices for final filling. Any finished blasting cap should have 5 - 10 cm of "dumb" space (at the upper end) filled with e.g. cotton wool, in order to create place for safe handling. Common practices in synthetic laboratories include the use of combined leather/kevlar/steel wire gloves, ear muffs/plugs and bulletproof glasses/glass panels. These are designed to protect against noise and flying fragments - not the blast itself.[60] It is important to note that some proportion of these accidents is not directly tied to the properties of acetone peroxide. The drivers behind these type of accidents are improper handling of pyrotechnic fuses or electric ignition systems. For example, a spark from a burning fuse can enter improperly sealed blasting cap immediately after ignition or it can ignite the distant end of the exposed fuse. Faulty fuses with extremely short, long or variable times of burning are possible. Electric ignition systems are liable to prematurely detonate because of static discharges at unshortened wire leads or due to close proximity of devices emiting RF energy (cell phones, walkie-talkies, HV electricity transmissions or stray lightning bolts from distant storms). Pulling the wire or fuse with force can induce inner friction inside the blasting cap, which can lead to detonation. Pushing the blasting cap into the charge with force can result in severe bending/total breakage of the blasting cap with catastrophic results. A thorough training is needed to properly employ both of these ignition methods.

Handling a TATP simulant via a paper wrapped wooden stick on paper, note that the lower left cotains 3× the recommended amount for a single paper. The second image shows a 5 l pot full of gypsum and flour (only middle sized and larger particles are allowed, very fine flour is flammable and not allowed). Such a pot can absorb the explosion of 1 - 2 g of TATP. There is a buried, inverted and gypsum filled plastic cup serving as a floor, approximately 10 cm below the surface. The cavity intended for filling, plastic funnel and surface cover papers (books) are absent. Image 3: a TATP blasting cap simulant made out of plastic, filled with 1 g of powder and an electric match. Note the lack of seals at the lower end and the paper stuffing with glue at the upper end. Only the upper end is safe enough to touch with fingers.
This is an example of typical blast mittigation device used in the filling of blasting caps and small firecrackers. The second image is an example of a typical amateur made blasting cap. A string may be attached to the outside - to pull out the blasting cap out of the charge in case of misfire.


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  2. ^ See:
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    • Wolfenstein R (1895) Deutsches Reichspatent 84,953
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  6. ^ (Baeyer and Villiger, 1900), p. 859.
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