Names | |
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Preferred IUPAC name 3,4,8,9,12,13-Hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H12N2O6 | |
Molar mass | 208.17 g/mol |
Appearance | White crystalline solid |
Density | 1.57 g/cm3 |
Melting point | Decomposes at 75 °C Ignites spontaneously at 133 °C |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Explosive |
GHS labelling: | |
Danger | |
H202, H205, H241, H300, H315, H318, H335 | |
P102, P220, P243, P250, P261, P264, P280, P283, P370+P380, P372, P404 | |
NFPA 704 (fire diamond) | |
Explosive data | |
Shock sensitivity | High |
Friction sensitivity | Very High |
Detonation velocity | ~2800 m/s (at around 0.4 g/cm3) - 5100 m/s at around 1.1 g/cm3 |
RE factor | 0.74 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Hexamethylene triperoxide diamine (HMTD) is a high explosive organic compound. HMTD is an organic peroxide, a heterocyclic compound with a cage-like structure. It is a primary explosive. It has been considered as an initiating explosive for blasting caps in the early part of 20th century, mostly because of its high initiating power (higher than that of mercury fulminate) and its inexpensive production. As such, it was quickly taken up as a primary explosive in mining applications. [1] However, it has since been superseded by more (chemically) stable compounds such as dextrinated lead azide and DDNP (which contains no lead or mercury). HMTD is widely used in amateur-made blasting caps.
First synthesised in 1885 by the German chemist Ludwig Legler, [2] HMTD may be prepared by the reaction of an aqueous solution of hydrogen peroxide and hexamine in the presence of an acid catalyst, such as citric acid, acetic acid or dilute sulfuric acid. The hydrogen peroxide needs to be at least 12% w/w concentration, as lower concentrations lead to poor yields. Citric acid is overall superior to other acids, providing a yield of up to about 50%.
The molecule adopts a cage-like structure with the nitrogen atoms having an unusual trigonal planar geometry. [3]
Like other organic peroxides, such as acetone peroxide (TATP), HMTD is unstable and detonates upon shock, friction, static electricity discharges, concentrated sulfuric acid, strong UV radiation and heat. Cases of detonation caused by the simple act of screwing a lid on a jar containing HMTD have been reported. [4] Common static electricity discharges have been reported to cause detonation. [5] It is, however, less unstable than many other peroxides under normal conditions; exposure to ultraviolet light increases its sensitivity. It also reacts with most common metals, which can lead to detonation. HMTD is chemically very stable when pure (free of acids, bases, and metal ions) and does not quickly sublime like its acetone counterparts.
HMTD is a more powerful initiating explosive than mercury fulminate, but its poor thermal and chemical stability prevents its use in detonators. [6] Nevertheless, HMTD is one of the three most widely used primary explosives in improvised, amateur made blasting caps. The other being TATP and silver acetylide.
HMTD is a common source of injury among amateur chemists, particularly finger amputations. Most of these injuries are caused by small amounts of HMTD that inadvertently detonate in close proximity of fingers, since small amounts (grams) are generally not powerful enough to amputate fingers from distances larger than 5 – 10 cm. [7] Experienced amateurs handle HMTD 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 HMTD on a single filter paper, pre-bent papers with cotton wrapped wooden rods for manipulation and blast mitigation devices for final filling.
Calculated (Explo5) detonation pressure Pcj at crystal density 1.597 g/cm3 is 218 kbar with velocity of detonation VoD = 7777 m/s. Explosion temperature is 3141 K, energy of explosion is 5612 kJ/kg (or 3400 - 4000 kJ/kg per various sources) and volume of explosion gases at STP is calculated to be 826 L/kg. Loose powder has density close to 0.4 g/cm3, hence the common detonation velocities are closer to 3000 m/s and Pcj is closer to 15 kbar. [8]
HMTD is overall slightly more sensitive than fresh TATP and can be considered to be slightly more dangerous than an average primary explosive. 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.
Despite no longer being used in any military application, and despite its shock sensitivity, HMTD remains a common home-made explosive and has been used in a large number of suicide bombings and other attacks throughout the world. For example, it was one of the components in the explosives intended to bomb Los Angeles International Airport in the 2000 millennium attack plots [9] [10] and the 2016 New York and New Jersey bombings, [11] as well as one of the components of the explosives attempted to be made by the neo-Nazi terrorist organization Atomwaffen Division in the United States. [12]
Dynamite is an explosive made of nitroglycerin, sorbents, and stabilizers. It was invented by the Swedish chemist and engineer Alfred Nobel in Geesthacht, Northern Germany, and patented in 1867. It rapidly gained wide-scale use as a more robust alternative to black powder.
An explosive is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An explosive charge is a measured quantity of explosive material, which may either be composed solely of one ingredient or be a mixture containing at least two substances.
Nitroglycerin (NG), also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Invented in 1847 by Ascanio Sobrero, nitroglycerin has been used ever since as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. Since the 1880s, it has been used by militaries as an active ingredient and gelatinizer for nitrocellulose in some solid propellants such as cordite and ballistite. It is a major component in double-based smokeless propellants used by reloaders. Combined with nitrocellulose, hundreds of powder combinations are used by rifle, pistol, and shotgun reloaders.
Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, TEN, corpent, or penthrite, is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66. When mixed with a plasticizer, PETN forms a plastic explosive. Along with RDX it is the main ingredient of Semtex.
Mercury(II) fulminate, or Hg(CNO)2, is a primary explosive. It is highly sensitive to friction, heat and shock and is mainly used as a trigger for other explosives in percussion caps and detonators. Mercury(II) cyanate, though its chemical formula is identical, has a different atomic arrangement; the cyanate and fulminate anions are isomers.
Picric acid is an organic compound with the formula (O2N)3C6H2OH. Its IUPAC name is 2,4,6-trinitrophenol (TNP). The name "picric" comes from Greek: πικρός (pikros), meaning "bitter", due to its bitter taste. It is one of the most acidic phenols. Like other strongly nitrated organic compounds, picric acid is an explosive, which is its primary use. It has also been used as medicine (antiseptic, burn treatments) and as a dye.
Ahmed Ressam is an Algerian al-Qaeda member who lived for a time in Montreal, Quebec, Canada. He received extensive terrorist training in Afghanistan.
Lead styphnate (lead 2,4,6-trinitroresorcinate, C6HN3O8Pb ), whose name is derived from styphnic acid, is an explosive used as a component in primer and detonator mixtures for less sensitive secondary explosives. Lead styphnate is only slightly soluble in water and methanol. Samples of lead styphnate vary in color from yellow to gold, orange, reddish-brown, to brown. Lead styphnate is known in various polymorphs, hydrates, and basic salts. Normal lead styphnate monohydrate, monobasic lead styphnate, tribasic lead styphnate dihydrate, and pentabasic lead styphnate dehydrate as well as α, β polymorphs of lead styphnate exist.
Acetone peroxide is an organic peroxide and a primary explosive. It is produced by the reaction of acetone and hydrogen peroxide to yield a mixture of linear monomer and cyclic dimer, trimer, and tetramer forms. The dimer is known as diacetone diperoxide (DADP). The trimer is known as triacetone triperoxide (TATP) or tri-cyclic acetone peroxide (TCAP). Acetone peroxide takes the form of a white crystalline powder with a distinctive bleach-like odor or a fruit-like smell when pure, and can explode powerfully if subjected to heat, friction, static electricity, concentrated sulfuric acid, strong UV radiation or shock. Until about 2015, explosives detectors were not set to detect non-nitrogenous based explosives, as most explosives used preceding 2015 were nitrogen-based. TATP, being nitrogen-free, has been used as the explosive of choice in several terrorist bomb attacks since 2001.
Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.
The safety testing of explosives involves the determination of various properties of the different energetic materials that are used in commercial, mining, and military applications. It is highly desirable to measure the conditions under which explosives can be set off for several reasons, including: safety in handling, safety in storage, and safety in use.
Tannerite is a brand of binary explosive targets used for firearms practice and sold in kit form. The targets comprise a combination of oxidizers and a fuel, primarily aluminium powder, that is supplied as two separate components that are mixed by the user. The combination is relatively stable when subjected to forces less severe than a high-velocity bullet impact. A hammer blow, the product being dropped, or impact from a low-velocity bullet or shotgun blast will not initiate a reaction. It is also designed to be non-flammable, although its explosion can ignite flammable material.
The 2005 University of Oklahoma bombing occurred on October 1, 2005 at approximately 7:30 p.m. CDT, when a bomb went off near the George Lynn Cross Hall on Van Vleet Oval on the University of Oklahoma (OU) main campus. The blast took place less than 200 yards west of Oklahoma Memorial Stadium, where 84,501 spectators were attending a football game. The bomber, OU student Joel "Joe" Henry Hinrichs III, was killed in the explosion; no one else was killed.
A contact explosive is a chemical substance that explodes violently when it is exposed to a relatively small amount of energy. Though different contact explosives have varying amounts of energy sensitivity, they are all much more sensitive relative to other kinds of explosives. Contact explosives are a part of a group of explosives called primary explosives, which are also very sensitive to stimuli but not to the degree of contact explosives. The extreme sensitivity of contact explosives is due to either chemical composition, bond type, or structure.
A pyrotechnic composition is a substance or mixture of substances designed to produce an effect by heat, light, sound, gas/smoke or a combination of these, as a result of non-detonative self-sustaining exothermic chemical reactions. Pyrotechnic substances do not rely on oxygen from external sources to sustain the reaction.
Tetranitromethane or TNM is an organic oxidizer with chemical formula C(NO2)4. Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric acid.
Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact.
An explosion is a rapid expansion in volume associated with an extreme outward release of energy, usually with the generation of high temperatures and release of high-pressure gases. Supersonic explosions created by high explosives are known as detonations and travel through shock waves. Subsonic explosions are created by low explosives through a slower combustion process known as deflagration.
Tetrazene is an explosive material used for sensitization of priming compositions. It is a derivative of the compound with the IUPAC name tetrazene.
Nickel hydrazine nitrate (NHN), (chemical formula: [Ni(N2H4)3](NO3)2 is an energetic material having explosive properties in between that of primary explosive and a secondary explosive. It is a salt of a coordination compound of nickel with a reaction equation of 3N2H4·H2O + Ni(NO3)2 →〔Ni(N2H4)3〕(NO3)2 + 3H2O