Acetone peroxide

Ball-and-stick model of the acetone peroxide trimer (TATP)

Acetone peroxide (triacetone triperoxide, peroxyacetone, TATP, TCAP) is an organic peroxide and a primary high explosive. It takes the form of a white crystalline powder with a distinctive acrid smell. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article does not cite its references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... BIC pen cap, about 1 gram. ... The mole (symbol: mol) is the SI base unit that measures an amount of substance. ... Shock sensitivity is a comparative measure of the sensitivity to sudden movement of a chemical compound, usually of an explosive. ... Friction Sensitivity This is an approximation of the amount of friction or rubbing a compound can withstand before prematurely exploding. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... djbdasjkhfohasoiflkasdfioalkjsfoijaoislkna wu9832u09q1b oai iu3y hq oi23u89q This page meets Wikipedias criteria for speedy deletion. ... Metre per second (U.S. spelling: meter per second) is an SI derived unit of both speed (scalar) and velocity (vector), defined by distance in metres divided by time in seconds. ... Relative effectiveness factor () is a measurement of an explosives power for military demolitions purposes. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... Celsius is, or relates to, the Celsius temperature scale (previously known as the centigrade scale). ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... A natural smile without teeth showing A natural smile with teeth showing In physiology, a smile is a facial expression formed by flexing muscles most notably near both ends of the mouth, but also around the eyes. ... Image File history File links Download high resolution version (1164x954, 962 KB) Acetone Peroxide crystals File links The following pages link to this file: Acetone peroxide ... Image File history File links Download high resolution version (1164x954, 962 KB) Acetone Peroxide crystals File links The following pages link to this file: Acetone peroxide ... Image File history File links Download high-resolution version (1013x1100, 203 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Acetone peroxide ... Image File history File links Download high-resolution version (1013x1100, 203 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Acetone peroxide ... armchair conformational isomerism of Cyclohexane. ... The general structure of an organic peroxide. ... This article is concerned solely with chemical explosives. ...

It is highly susceptible to heat, friction, and shock. For its instability, it has been called the "Mother of Satan".^[1] It has perhaps sprung into notoriety due to its alleged use in the July 2005 London bombings and has also been reported as the explosive favored by suspects arrested on August 10, 2006 who allegedly intended to destroy aeroplanes flying from the United Kingdom to the United States.^[2] In mechanics, a shock is a sudden acceleration or deceleration caused, for example, by impact or explosion. ... The following is a timeline of the 7 July 2005 London bombings and 21 July 2005 London bombings. ... August 10 is the 222nd day of the year (223rd in leap years) in the Gregorian calendar. ... For the Manfred Mann album, see 2006 (album). ... Police at the scene of one of the raids, on Forest Road, Walthamstow, London. ...

Acetone peroxide was discovered in 1895 by Richard Wolffenstein.^[3] He was the first chemist who used inorganic acids as a catalyst. He was also the first researcher who received a patent for using the peroxide as an explosive compound. In 1900 Bayer and Villiger described in some articles in the same journal the first synthesis of the dimer and used acids for the synthesis of both peroxides too. Information about it including the relative proportions of monomer, dimer, and trimer is also available an article of Milas and Golubović. ^[4] Other sources include crystal structure and 3d analysis in "The Chemistry of Peroxides" edited by Saul Patai (pp. 396–7), as well as the "Textbook of Practical Organic Chemistry" by Vogel. 1895 (MDCCCXCV) was a common year starting on Tuesday (see link for calendar) of the Gregorian calendar (or a common year starting on Thursday of the 12-day-slower Julian calendar). ... Postcard showing Nollendorfplatz c. ... Sucrose, or common table sugar, is composed of glucose and fructose. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... Sucrose, or common table sugar, is composed of glucose and fructose. ... Quartz crystal Synthetic bismuth crystal Insulin crystals Gallium, a metal that easily forms large single crystals A huge monocrystal of potassium dihydrogen phosphate grown from solution by Saint-Gobain for the megajoule laser of CEA. In chemistry and mineralogy, a crystal is a solid in which the constituent atoms, molecules...

Chemistry

Also known as "peroxyacetone", acetone peroxide most commonly refers to the cyclic trimer TCAP (tri-cyclic acetone peroxide, or tri-cyclo), also called triacetone triperoxide (TATP), obtained by a reaction between hydrogen peroxide and acetone in an acid-catalyzed nucleophilic addition.^[5] The cyclic dimer (C₆H₁₂O₄) and open monomer and dimer are also formed, but under proper conditions the cyclic trimer is the primary product. A tetrameric form was also described. ^[6] In mildly acidic or neutral conditions, the reaction is much slower and produces more monomeric organic peroxide than the reaction with a strong acid catalyst. Due to significant strain of the chemical bonds in the dimer and especially the monomer, they are even more unstable than the trimer.^[7] Cyclopropane is the smallest alicyclic compound. ... In chemistry a trimer is a reaction product of three identical molecules. ... Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. ... The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... It has been suggested that this article or section be merged into Catalysis. ... In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... Sucrose, or common table sugar, is composed of glucose and fructose. ... Trimer might refer to: trimer (chemistry), a reaction product composed of three identical molecules trimer (biochemistry), a compound of three macromolecules non-covalently bound This is a disambiguation page: a list of articles associated with the same title. ... In chemistry, an oligomer consists of a finite number of monomer units (oligo is Greek for a few), in contrast to a polymer which, at least in principle, consists of an infinite number of monomers. ... Acidity redirects here. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... The general structure of an organic peroxide. ... The presence of angle strain in a molecule indicates that in a specific chemical conformation there exists a bond angle that deviates from the bond angle required to archieve maximum bond strength. ... Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. ...

At room temperature, the trimeric form slowly sublimes, reforming as larger crystals of the same peroxide. Sublimation of an element or substance is a conversion between the solid and the gas phases with no intermediate liquid stage. ...

Acetone peroxide is notable as a high explosive not containing nitrogen. General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ...

TCAP generally burns when ignited, unconfined, in quantities less than about 2 grams. More than 2 grams will usually detonate when ignited; smaller quantities might detonate when even slightly confined. Completely dry TCAP is much more prone to detonation than the fresh product still wetted with water or acetone. The oxidation that occurs when burning is: Preparing C-4 explosive This article is concerned solely with chemical explosives. ... The most fundamental reactions in chemistry are the redox processes. ...

2 C₉H₁₈O₆ + 21 O₂ → 18 H₂O + 18 CO₂

Theoretical examination of the explosive decomposition of TCAP, in contrast, predicts in "formation of acetone and ozone as the main decomposition products and not the intuitively expected oxidation products."^[8] But even in 1943 German researcher described in the case of detonation of the trimer the formation of formaldehyde which is clearly a result of a fragmentation of primary formed oxyradicals^{[citation needed]}. This result is in good agreement with the results of 60 years of the study of controlled decompositions in various organic peroxides. It is the rapid creation of gas from a solid that creates the explosion. Very little heat is created by the explosive decomposition of TCAP. Recent research describes TCAP decomposition as an entropic explosion^{[citation needed]}. General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... Chemical decomposition or analysis is the fragmentation of a chemical compound into elements or smaller compounds. ... The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... For other uses, see Ozone (disambiguation). ... Triacetone triperoxide (TATP) decomposes in an entropic explosion. ...

The extreme shock, heat, and friction sensitivity are due to the instability of the molecule. Big crystals, found in older mixtures, are more dangerous, as they are easier to shatter — and initiate — than small ones. Instability in systems is generally characterized by some of the outputs or internal states growing without bounds. ... In science, a molecule is a group of atoms in a definite arrangement held together by chemical bonds. ...

Due to the cost and ease with which the precursors can be obtained, acetone peroxide is commonly manufactured by those without the resources needed to manufacture or buy more sophisticated explosives. When the reaction is carried out without proper equipment the risk of an accident is significant.

There is a common myth that the only "safe" acetone peroxide is the trimer, made at low temperatures:

"The mixture must be kept below 10 degrees Celsius. If the crystals form at this temperature, it forms the isomer called tricycloacetone peroxide, which is relatively stable and safe to handle. If the crystals form above this temperature, the dimerric form, called dicycloacetone peroxide. This isomer is much more unstable, and could go off at the touch, making it not safe enough to be considered a practical explosive. As long as the temperature is kept below 10 degrees Celsius, then there is little to worry about."^[9]

In reality, the acid-catalyzed peroxidation of acetone always produces a mixture of dimeric and trimeric forms.

The trimer is the more stable form, but not much more so than the dimer. All forms of acetone peroxide are very sensitive to initiation. Organic peroxides are sensitive, dangerous explosives. The military does not use them because there are many much better alternatives. Even for people who synthesize homemade explosives, there are many far safer alternatives. Even nitroglycerin is not nearly as sensitive as acetone peroxide.^{[citation needed]} In chemistry initiation is a chemical reaction that triggers one or more secondary reactions. ... This article is concerned solely with chemical explosives. ... Nitroglycerin (NG), also known as nitroglycerine, trinitroglycerin, and glyceryl trinitrate, is a chemical compound. ...

Industrial occurrence

Acetone peroxides are common and unwanted by-products of oxidation reactions, eg. those used in phenol syntheses. Due to their explosivity, they are hazardous. Numerous methods are used to reduce their production - shifting the pH to more alkaline, adjusting the reaction temperature, or adding a soluble copper(II) compound.^[10] A by-product is a secondary or incidental product deriving from a manufacturing process or chemical reaction, and is not the primary product or service being produced. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... The correct title of this article is . ... General Name, Symbol, Number copper, Cu, 29 Chemical series transition metals Group, Period, Block 11, 4, d Appearance metallic pinkish red Standard atomic weight 63. ...

Acetone peroxide and benzoyl peroxide are used as flour bleaching agents to bleach and "mature" flour. R-phrases , , S-phrases , , , Autoignition temperature 80°C RTECS number DM8575000 Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Tube of Basiron, a water-based 5% benzoyl peroxide preparation for the treatment of acne. ... Flour bleaching agent is a food additive added to flour in order to make it appear whiter (freshly milled flour is yellowish) and to oxidize the surfaces of the flour grains and help with developing of gluten. ... Commercial chlorine bleach To Bleach something, is to remove or lighten its color, sometimes as a preliminary step in the process of dyeing; a bleach is a chemical that produces these effects, often via oxidation. ... Look up flour in Wiktionary, the free dictionary. ...

Ketone peroxides, including acetone peroxide, methyl ethyl ketone peroxide, and benzoyl peroxide, find applications as initiators for polymerization reactions of eg. silicone or polyester resins, often encountered when making fiberglass. For these uses, the peroxides are typically in the form of a dilute solution in an organic solvent, however, even commercial products with higher concentrations of organic peroxides can form crystals around the lid when older, making the can shock-sensitive. Methyl ethyl ketone is more common for this purpose, however, as it is stable in storage. The general structure of an organic peroxide. ... Methyl ethyl ketone peroxide (MEKP) is an organic peroxide, a high explosive similar to acetone peroxide, and is quite dangerous to synthesize. ... R-phrases , , S-phrases , , , Autoignition temperature 80°C RTECS number DM8575000 Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Tube of Basiron, a water-based 5% benzoyl peroxide preparation for the treatment of acne. ... Another meaning of initiator is SCSI initiator. ... An example of alkene polymerisation, in which each Styrene monomer units double bond reforms as a single bond with another styrene monomer and forms polystyrene. ... Silicones (more accurately called polymerized siloxanes or polysiloxanes) are inorganic-organic polymers with the chemical formula [R2SiO]n, where R = organic groups such as methyl, ethyl, and phenyl. ... SEM picture of a bend in a high surface area polyester fiber with a seven-lobed cross section Polyester is a category of polymers, or, more specifically condensation polymers, which contain the ester functional group in their main chain. ... Insect trapped in resin. ... Bundle of fiberglass Fiberglass or glassfibre is material made from extremely fine fibers of glass. ...

Accidental byproduct

Acetone peroxide can also occur accidentally, when suitable chemicals are mixed together. For example, when methyl ethyl ketone peroxide is mixed with acetone when making fiberglass, and left to stand for some time, or when a mixture of peroxide and hydrochloric acid from printed circuit board etching (the FeCl₃ method is less smelly, more accurate, but slower) is mixed with waste acetone from cleaning the finished board and allowed to stand. While amounts obtained this way are typically much smaller than from intentional production, they are also less pure and prepared without cooling, and hence very unstable. Methyl ethyl ketone peroxide (MEKP) is an organic peroxide, a high explosive similar to acetone peroxide, and is quite dangerous to synthesize. ... Part of a 1983 Sinclair ZX Spectrum computer board. ... Iron(III) chloride, generically called ferric chloride, is an iron-based salt of chemical formula FeCl3. ...

It is also a hazardous by-product of isosafrole oxidation in acetone, a step in the synthesis of MDMA. Chemical structure of trans-isosafrole. ... ecstasy and religious ecstasy MDMA, most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the brain to rapidly secrete large amounts of serotonin, causing a general sense of openness, empathy, energy, euphoria, and well-being. ...

Clandestine usage

TATP has been identified in explosive devices in a number of cases involving terrorists. Richard Reid, who attempted to down American Airlines Flight 63 with a bomb concealed in his shoe, employed a device containing plastic explosive with a TATP trigger. It is also believed that acetone peroxide was used as the explosive in the 7 July 2005 London bombings.^[11] On September 5, 2006, homemade TATP was found during the arrest of seven suspected terrorists in Vollsmose, a neighborhood in the Danish city Odense. In addition, the participants in the 2006 transatlantic aircraft plot may have planned to use TATP as the liquid bombs, mixed in aeroplane lavatories, that would destroy U.S. airliners flying from London to the United States.^[12] Nevertheless, some reports suggest that such bombs would not have been very effective, due to the supplies needed, the smell mixing would create, and the time it would take to prepare without drawing suspicion from passengers and the flight crew.^[13] Richard Colvin Reid (born August 12, 1973), also known as the shoe bomber, is an individual convicted on charges of terrorism currently serving a life sentence in the United States. ... Matt Lauer with the crew of Flight 63, the Shoebomber flight. ... Locations of the bombings, overlaid onto a real-path map of the London Underground The 7 July 2005 London bombings were a series of coordinated terrorist bomb blasts that hit Londons public transport system during the morning rush hour. ... The Vollsmose terrorists are nine people arrested on charges of terrorism by the Danish police in the Vollsmose neighborhood of Odense on September 5th, 2006. ... Odense is the third largest city in Denmark with 145,554 inhabitants (Odense city January 1, 2004) and the capital of the island of Funen. ... Police at the scene of one of the raids, on Forest Road, Walthamstow, London. ...

References

1. ^ July 15, 2005 TimesOnline
2. ^ http://www.time.com/time/nation/article/0,8599,1225453,00.html
3. ^ Wolffenstein, R (1895). "Über die Einwirkung von Wasserstoffsuperoxyd auf Aceton und Mesityloxyd". Chemische Berichte 28: 2265. 
4. ^ Milas N. A., 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. 
5. ^ Megalomania's Method of Making Acetone Peroxide. Megalomania's Controversial Chem Lab (January 31, 2004).
6. ^ 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: 288-289. DOI:10.1039/a809955c. 
7. ^ Schulte-Ladbeck, R.; Kolla, P.; Karst, U. (2003). "Trace Analysis of Peroxide-Based Explosives". Analytical Chemistry 75 (4): 731-735. DOI:10.1021/ac020392n. 
8. ^ F. Dubnikova, R. Kosloff, J. Almog, Y. Zeiri, R. Boese, H. Itzhaky, A. Alt, E. Keinan (2003). "Decomposition of Triacetone Triperoxide Is an Entropic Explosion". Journal of the American Chemical Society 127 (4): 1146 - 1159. DOI:10.1021/ja0464903. 
9. ^ "Detailed description of the synthesis of Acetone Peroxide"
10. ^ Destruction of acetone peroxide patent
11. ^ "The real story of 7/7", The Observer, May 7, 2006
12. ^ "Terror plot sparks frenzied speculation about liquid explosives", Chemistry World, August 11, 2006
13. ^ "Mass murder in the skies: was the plot feasible?", The Register, August 17, 2006

The Journal of the American Chemical Society (usually abbreviated as , or JACS), is a peer-reviewed scientific journal, published since 1879 by the American Chemical Society. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Analytical chemistry is the analysis of material samples to gain an understanding of their chemical composition and structure. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... The Journal of the American Chemical Society (usually abbreviated as , or JACS), is a peer-reviewed scientific journal, published since 1879 by the American Chemical Society. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Wikipedia does not yet have an article with this exact name. ... Royal Society of Chemistry The Royal Society of Chemistry is a learned society (professional association) in the United Kingdom with the goal of advancing the chemical sciences. ... Current logo of The Register. ...

See also

• Methyl ethyl ketone peroxide
• Chemical Synthesis of Acetone peroxide on Wikibooks

Methyl ethyl ketone peroxide (MEKP) is an organic peroxide, a high explosive similar to acetone peroxide, and is quite dangerous to synthesize. ...

External links

• Links to external chemical sources
• TATP is Suicide bombers weapon of Choice The Times Online UK
• Thwarting the Airline Plot: Inside the Investigation TIME magazine
• Decomposition of Triacetone Triperoxide Is an Entropic Explosion (PDF-800KB), Journal of the American Chemical Society, January 5, 2005.
• Mass murder in the skies: was the TATP plot feasible?, The Register, August 17, 2006.
• Liquid explosives very difficult to make, WorkingForChange, August 22, 2006.
• TATP – Countering the Mother of Satan - Comprehensive article covering different aspects of TATP identifying it in the field.