Difference between revisions of "Acetone peroxide"

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'''Acetone peroxide''', often referred to as '''TATP''' or '''Mother of Satan''', is an explosive organic peroxide with a vast, well earned reputation for maiming, terrorism, and 'kewlism'.  
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| Name = Acetone peroxide
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| Reference =
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| IUPACName = 3,3-Dimethyl-1,2-dioxacyclopropane<br>(monomer)<br>3,3,6,6-Tetramethyl-1,2,4,5-tetraoxane<br>(dimer)<br>3,3,6,6,9,9-Hexamethyl-1,2,4,<br>5,7,8-hexaoxacyclononane<br>(trimer)<br>3,3,6,6,9,9,12,12-Octamethyl-1,2,4,<br>5,7,8,10,11-octaoxacyclododecane<br>(tetramer)
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| PIN =
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| SystematicName =
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| OtherNames = Mother of Satan<br>Peroxyacetone<br>Triacetone triperoxide
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = White solid
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| BoilingPt =
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| BoilingPtC = 97 to 160
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| BoilingPt_ref =
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| BoilingPt_notes = (detonates)
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| Density = 1.22 g/cm<sup>3</sup> (trimer)<ref>O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1649</ref>
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| Formula = C<sub>6</sub>H<sub>12</sub>O<sub>4</sub> (dimer)<br>C<sub>9</sub>H<sub>18</sub>O<sub>6</sub> (trimer)<br>C<sub>12</sub>H<sub>24</sub>O<sub>8</sub> (tetramer)
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| HenryConstant =
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| LogP =
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| MolarMass = 148.157 g/mol (dimer)<br>222.24 g/mol (trimer)
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| MeltingPt =
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| MeltingPtC =
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| MeltingPt_ref = 131.5 to 133 °C (268.7 to 271.4 °F; 404.6 to 406.1 K) (dimer)<ref>Federoff, Basil T.  et al., ''Encyclopedia of Explosives and Related Items'' (Springfield, Virginia:  National Technical Information Service, 1960), vol. 1, [https://archive.org/stream/Ullmans/01%20Ullmans-U-S-ARMY-Encyclopedia-of-Explosives-and-Related-Items-Vol-01#page/n147/mode/2up p. A41.]</ref>
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| MeltingPt_notes = <hr>91 °C (195.8 °F; 364 K) (trimer)
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| Odor = Odorless
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| pKa =
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| pKb =
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| Solubility = Insoluble
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| SolubleOther = Soluble in [[acetone]], [[chloroform]], [[dichloromethane]], [[methanol]], [[toluene]]
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| ShockSens = High / moderate when wet
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| FrictionSens = High / moderate when wet
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| DetonationV = 5300 m/s
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| REFactor = 0.83
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| Section6 = {{Chembox Hazards
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| AutoignitionPt =
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| ExploLimits =
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| ExternalMSDS = [https://cameochemicals.noaa.gov/chemical/19283 CAMEO]
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| FlashPt =
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| MainHazards = Explosive
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| OtherCompounds = [[Dimethyldioxirane]]<br>[[Methyl ethyl ketone peroxide]]
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  }}
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'''Acetone peroxide''', often referred to as '''TATP''' or '''Mother of Satan''', is an explosive organic peroxide with a vast, well earned reputation for maiming, terrorism, and 'kewlism'. Because of this, it is probably [[Sciencemadness Discussion Board|Sciencemadness's]] least favourite non-drug chemical, and posts involving this are usually ignored or ridiculed.
  
−
Because of this, it is probably [[Sciencemadness Discussion Board|Sciencemadness's]] least favourite non-drug chemical, and posts involving this are usually ignored or ridiculed.
+
Acetone peroxide exists most commonly in the cyclic trimer form. Dimer and monomer forms also exist, as well as a more stable tetrameric form. The monomer form is known as [[dimethyldioxirane]] (or DMDO).
−
 
+
−
Acetone peroxide exists most commonly in the cyclic trimer form. Dimer and monomer forms also exist, as well as a more stable tetrameric form.
+
  
 
==Properties==
 
==Properties==
Line 10: Line 117:
  
 
Acetone peroxide burns very fast if unconfined (it still detonates even when unconfined in gram amounts however) with an orange flame, producing no smoke or ash. The explosion of TATP is primarily driven by entropy and generates relatively little heat.
 
Acetone peroxide burns very fast if unconfined (it still detonates even when unconfined in gram amounts however) with an orange flame, producing no smoke or ash. The explosion of TATP is primarily driven by entropy and generates relatively little heat.
 +
 +
Addition of conc. [[sulfuric acid]] (>80%) to solid acetone peroxide will result in detonation. If the AP is wetted with a solvent, the addition of sulfuric acid will not cause detonation, but instead a violent decomposition reaction occurs. Other acids, like methylsulfonic acid or HClO4 will alos lead to violent decomposition, as does the addition of boron trifluoride. Alkali bases do not react with the peroxide.<ref>http://energetics.chm.uri.edu/system/files/TATP%20III%20paper%202013.pdf</ref>
  
 
===Physical===
 
===Physical===
−
Acetone peroxide exists as a monomer, a dimer and a trimer. All of these are white solids, insoluble in water, but soluble in [[chloroform]] and [[toluene]].  
+
Acetone peroxide exists as a monomer, a dimer and a trimer. All of these are white solids, insoluble in water, but soluble in organic solvents, such as [[chloroform]] and [[toluene]].  
  
 +
===Explosive===
 
TATP explodes very easily, often too easily. It is static, friction, shock and heat sensitive and can easily detonate unconfined.
 
TATP explodes very easily, often too easily. It is static, friction, shock and heat sensitive and can easily detonate unconfined.
  
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==Availability==
 
==Availability==
−
TATP is not avaliable anywhere as it does not store at all well.  
+
TATP is not available anywhere as it does not store at all well.  
  
 
Organic peroxides have been used in numerous terrorism incidents, so producing or storing large amounts of this chemical is seen as intent to carry out such an act.
 
Organic peroxides have been used in numerous terrorism incidents, so producing or storing large amounts of this chemical is seen as intent to carry out such an act.
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TATP is unpredictable. Detonations from static shock, bumping a container or even with no apparent reason at all have been reported.  
 
TATP is unpredictable. Detonations from static shock, bumping a container or even with no apparent reason at all have been reported.  
  
−
If the synthesis is undertaken, the solution must be kept as cold as possible to limit the formation of the monomer and dimer which are even more chemically unstable (which is really, really saying something) than the trimer form.  
+
If the synthesis is undertaken, the solution must be kept as cold as possible to limit the formation of the monomer and dimer which are even more chemically unstable (which is really, really saying something) than the trimer form, and to prevent the formation of highly lachrymatory and toxic [[chloroacetone]].
  
 
==Handling==
 
==Handling==
 
===Safety===
 
===Safety===
−
As of yet, there is no riskless synthesis of acetone peroxide, and it is unlikely there will ever be one. Any single error or deviation from ideal conditions (which aren't even known entirely) in the synthesis can make the product formed drastically more sensitive and unpredictable, and this is often the case. A huge danger in the storage of acetone peroxide is from its ability to sublime. In a container, the solid will sublime forming very unstable crystals on the lid and walls. This can easily lead to an explosion the next time the container is open, obviously with dire consequences. Another issue in the production of TATP is the production of the monomeric or dimeric forms, which are even less stable and can trigger detonation of an entire sample.<ref>http://www0.bnl.gov/esh/cms/pdf/peroxides.pdf</ref>
+
As of yet, there is no riskless synthesis of acetone peroxide, and it is unlikely there will ever be one. Any single error or deviation from ideal conditions (which aren't even known entirely) in the synthesis can make the product formed either contain dangerous side products, or make it drastically more sensitive and unpredictable, and this is often the case. A huge danger in the storage of acetone peroxide is from its ability to sublime. In a container, the solid will sublime forming very unstable crystals on the lid and walls. This can easily lead to an explosion the next time the container is open, obviously with dire consequences. Another issue in the production of TATP is the production of the monomeric or dimeric forms, which are even less stable and can trigger detonation of an entire sample.<ref>http://www0.bnl.gov/esh/cms/pdf/peroxides.pdf</ref>
  
 
As it is formed from common lab chemicals, care should be taken to avoid forming this substance accidentally from discarded chemicals. Organic molecules should always be kept away from even mildly concentrated solutions of hydrogen peroxide until thorough research on possible reactions has been conducted, as there are many, many other highly dangerous peroxides.
 
As it is formed from common lab chemicals, care should be taken to avoid forming this substance accidentally from discarded chemicals. Organic molecules should always be kept away from even mildly concentrated solutions of hydrogen peroxide until thorough research on possible reactions has been conducted, as there are many, many other highly dangerous peroxides.
 +
 +
Due to its high friction sensitivity, grinding acetone peroxide in a mortar is a very bad idea.<ref>http://www.youtube.com/watch?v=tmnwkb4aFBQ</ref>
 +
 +
===Legal===
 +
The manufacture, possession or use of acetone peroxide and other organic peroxide explosives without a permit/license is a crime in most countries.
 +
 +
It is a federal offense to make, possess, or use TATP in the United States.
  
 
===Storage===
 
===Storage===
−
NEVER STORE ACETONE PEROXIDE EVER!
+
Acetone peroxide is a high explosive and cannot be safely stored in any amount.
 +
 
 +
One Sciencemadness user has discovered that a mixture of TATP/MEKP stored in sealed containers underground at low and constant temperatures, show practically no decomposition, even after 13 years.<ref>http://www.sciencemadness.org/talk/viewthread.php?tid=20&page=14#pid436596</ref><ref>http://www.sciencemadness.org/talk/viewthread.php?tid=10102#pid491902</ref>
  
 
===Disposal===
 
===Disposal===
−
Acetone peroxide can be rendered relative benign by dissolving it in [[toluene]]. Even if the solution is saturated, there is almost no risk of detonation. Although AP can be destroyed by burning diluted solutions of peroxides or via thermal degradation, this method is too risky. Many common reducing agents, such as acidified KI, [[iron(II) sulfate]], [[ammonium sulfate]]·[[iron(II) sulfate]] have shown to have little effect on peroxides. However, acetone peroxide can be reduced by refluxing it in ethanol or toluene for 1-2 hours or heated to 65°C for 6 hours, in the presence of an excess of [[tin(II) chloride]]. Another way to reduce acetone peroxide is by refluxing it in an organic solvent, such as benzene, in the presence of [[hydroquinone]].<ref>http://www.sciencemadness.org/talk/files.php?pid=36743&aid=569</ref>
+
Acetone peroxide can be rendered relatively benign by dissolving it in [[toluene]]. Even if the solution is saturated, there is almost no risk of detonation. Although AP can be destroyed by burning diluted solutions of peroxides or via thermal degradation, this method is too risky. Many common reducing agents, such as acidified KI, [[iron(II) sulfate]], [[ammonium sulfate]]·[[iron(II) sulfate]] have shown to have little effect on peroxides.
  
−
Acetone peroxide can also be destroyed by refluxing it in the presence of other reducing agents, such as [copper(II) acetate] (pH = 5.7).<ref>https://docs.google.com/viewer?url=patentimages.storage.googleapis.com/pdfs/US5003109.pdf</ref>
+
There are several ways to safely neutralize AP described in literature:
  
−
An even more accessible way is to reduce it with a suspension of ZnCl<sub>2</sub>/Zn, in either ethanol or water.
+
A safe and reliable way involves "wetting" the acetone peroxide with an alcohol (methanol, ethanol, etc.), followed by addition of HCl 36-37%, which hydrolyzes the peroxide. Primary alcohols have been shown to aid the decomposition of the peroxide more than secondary ones (i.e. isopropanol), thus these should be used.<ref>https://www.researchgate.net/publication/259541868_Factors_Influencing_Destruction_of_Triacetone_Triperoxide_TATP</ref><ref>http://energetics.chm.uri.edu/system/files/TATP%20III%20paper%202013.pdf</ref>
  
−
===Legal===
+
In one method, acetone peroxide can be reduced by refluxing it in ethanol or toluene for 1-2 hours or heated to 65°C for 6 hours, in the presence of an excess of [[tin(II) chloride]].
−
It is a federal offense to make, possess, or use TATP in the United States.
+
 
 +
Another way to reduce acetone peroxide is by refluxing it in an organic solvent, such as benzene, in the presence of [[hydroquinone]].<ref>http://www.sciencemadness.org/talk/files.php?pid=36743&aid=569</ref>
 +
 
 +
Acetone peroxide can also be destroyed by refluxing it in the presence of soluble copper salts, such as [copper(II) acetate] (pH = 5.7).<ref>https://docs.google.com/viewer?url=patentimages.storage.googleapis.com/pdfs/US5003109.pdf</ref>
 +
 
 +
An even more accessible way is to reduce it with a suspension of ZnCl<sub>2</sub>/Zn, in either ethanol or water.
  
 
==See also==
 
==See also==
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=8038 TATP--How sensitive is it?]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=8038 TATP--How sensitive is it?]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=13179 Cubic acetone peroxide crystals]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=13179 Cubic acetone peroxide crystals]
 +
*[http://http://www.sciencemadness.org/talk/viewthread.php?tid=65456 Explosive Peroxide Testing and Prevention]
  
 
[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
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[[Category:Things that can kill you very quickly]]
 
[[Category:Things that can kill you very quickly]]
 
[[Category:Things that should NOT be messed with except by professionals]]
 
[[Category:Things that should NOT be messed with except by professionals]]
 +
[[Category:Kewlism]]

Latest revision as of 09:11, 8 June 2024

Acetone peroxide
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
Mother of Satan
Peroxyacetone
Triacetone triperoxide
Properties
C6H12O4 (dimer)
C9H18O6 (trimer)
C12H24O8 (tetramer)
Molar mass 148.157 g/mol (dimer)
222.24 g/mol (trimer)
Appearance White solid
Odor Odorless
Density 1.22 g/cm3 (trimer)[1]
Melting point 131.5 to 133 °C (268.7 to 271.4 °F; 404.6 to 406.1 K) (dimer)[2]
91 °C (195.8 °F; 364 K) (trimer)
Boiling point 97 to 160 °C (207 to 320 °F; 370 to 433 K) (detonates)
Insoluble
Solubility Soluble in acetone, chloroform, dichloromethane, methanol, toluene
Hazards
Safety data sheet CAMEO
Related compounds
Related compounds
 Dimethyldioxirane
Methyl ethyl ketone peroxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetone peroxide, often referred to as TATP or Mother of Satan, is an explosive organic peroxide with a vast, well earned reputation for maiming, terrorism, and 'kewlism'. Because of this, it is probably Sciencemadness's least favourite non-drug chemical, and posts involving this are usually ignored or ridiculed.

Acetone peroxide exists most commonly in the cyclic trimer form. Dimer and monomer forms also exist, as well as a more stable tetrameric form. The monomer form is known as dimethyldioxirane (or DMDO).

Properties

Chemical

Chemistry with acetone peroxide is not done due to its low solubility and explosive properties.

Acetone peroxide burns very fast if unconfined (it still detonates even when unconfined in gram amounts however) with an orange flame, producing no smoke or ash. The explosion of TATP is primarily driven by entropy and generates relatively little heat.

Addition of conc. sulfuric acid (>80%) to solid acetone peroxide will result in detonation. If the AP is wetted with a solvent, the addition of sulfuric acid will not cause detonation, but instead a violent decomposition reaction occurs. Other acids, like methylsulfonic acid or HClO4 will alos lead to violent decomposition, as does the addition of boron trifluoride. Alkali bases do not react with the peroxide.[3]

Physical

Acetone peroxide exists as a monomer, a dimer and a trimer. All of these are white solids, insoluble in water, but soluble in organic solvents, such as chloroform and toluene.

Explosive

TATP explodes very easily, often too easily. It is static, friction, shock and heat sensitive and can easily detonate unconfined.

Like most explosives, TATP more sensitive when dry than wet. However, more so than other primary explosives, TATP sublimes very quickly, depositing large unstable crystals on inconvenient places which can detonate without warning.

Availability

TATP is not available anywhere as it does not store at all well.

Organic peroxides have been used in numerous terrorism incidents, so producing or storing large amounts of this chemical is seen as intent to carry out such an act.

Preparation

TATP is made by people who either don't know any better, or know exactly what they're doing. Because you're on this site, you know better, so don't make it. If your facilities only allow you to make this explosive, you shouldn't be making explosives. If you cannot figure out how to do this simple synthesis yourself, chances are you are not experienced enough to make it.

TATP is unpredictable. Detonations from static shock, bumping a container or even with no apparent reason at all have been reported.

If the synthesis is undertaken, the solution must be kept as cold as possible to limit the formation of the monomer and dimer which are even more chemically unstable (which is really, really saying something) than the trimer form, and to prevent the formation of highly lachrymatory and toxic chloroacetone.

Handling

Safety

As of yet, there is no riskless synthesis of acetone peroxide, and it is unlikely there will ever be one. Any single error or deviation from ideal conditions (which aren't even known entirely) in the synthesis can make the product formed either contain dangerous side products, or make it drastically more sensitive and unpredictable, and this is often the case. A huge danger in the storage of acetone peroxide is from its ability to sublime. In a container, the solid will sublime forming very unstable crystals on the lid and walls. This can easily lead to an explosion the next time the container is open, obviously with dire consequences. Another issue in the production of TATP is the production of the monomeric or dimeric forms, which are even less stable and can trigger detonation of an entire sample.[4]

As it is formed from common lab chemicals, care should be taken to avoid forming this substance accidentally from discarded chemicals. Organic molecules should always be kept away from even mildly concentrated solutions of hydrogen peroxide until thorough research on possible reactions has been conducted, as there are many, many other highly dangerous peroxides.

Due to its high friction sensitivity, grinding acetone peroxide in a mortar is a very bad idea.[5]

Legal

The manufacture, possession or use of acetone peroxide and other organic peroxide explosives without a permit/license is a crime in most countries.

It is a federal offense to make, possess, or use TATP in the United States.

Storage

Acetone peroxide is a high explosive and cannot be safely stored in any amount.

One Sciencemadness user has discovered that a mixture of TATP/MEKP stored in sealed containers underground at low and constant temperatures, show practically no decomposition, even after 13 years.[6][7]

Disposal

Acetone peroxide can be rendered relatively benign by dissolving it in toluene. Even if the solution is saturated, there is almost no risk of detonation. Although AP can be destroyed by burning diluted solutions of peroxides or via thermal degradation, this method is too risky. Many common reducing agents, such as acidified KI, iron(II) sulfate, ammonium sulfate·iron(II) sulfate have shown to have little effect on peroxides.

There are several ways to safely neutralize AP described in literature:

A safe and reliable way involves "wetting" the acetone peroxide with an alcohol (methanol, ethanol, etc.), followed by addition of HCl 36-37%, which hydrolyzes the peroxide. Primary alcohols have been shown to aid the decomposition of the peroxide more than secondary ones (i.e. isopropanol), thus these should be used.[8][9]

In one method, acetone peroxide can be reduced by refluxing it in ethanol or toluene for 1-2 hours or heated to 65°C for 6 hours, in the presence of an excess of tin(II) chloride.

Another way to reduce acetone peroxide is by refluxing it in an organic solvent, such as benzene, in the presence of hydroquinone.[10]

Acetone peroxide can also be destroyed by refluxing it in the presence of soluble copper salts, such as [copper(II) acetate] (pH = 5.7).[11]

An even more accessible way is to reduce it with a suspension of ZnCl2/Zn, in either ethanol or water.

See also

References

  1. ↑ O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1649
  2. ↑ Federoff, Basil T. et al., Encyclopedia of Explosives and Related Items (Springfield, Virginia: National Technical Information Service, 1960), vol. 1, p. A41.
  3. ↑ http://energetics.chm.uri.edu/system/files/TATP%20III%20paper%202013.pdf
  4. ↑ http://www0.bnl.gov/esh/cms/pdf/peroxides.pdf
  5. ↑ http://www.youtube.com/watch?v=tmnwkb4aFBQ
  6. ↑ http://www.sciencemadness.org/talk/viewthread.php?tid=20&page=14#pid436596
  7. ↑ http://www.sciencemadness.org/talk/viewthread.php?tid=10102#pid491902
  8. ↑ https://www.researchgate.net/publication/259541868_Factors_Influencing_Destruction_of_Triacetone_Triperoxide_TATP
  9. ↑ http://energetics.chm.uri.edu/system/files/TATP%20III%20paper%202013.pdf
  10. ↑ http://www.sciencemadness.org/talk/files.php?pid=36743&aid=569
  11. ↑ https://docs.google.com/viewer?url=patentimages.storage.googleapis.com/pdfs/US5003109.pdf

Relevant Sciencemadness threads

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