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| Names | |
|---|---|
| Preferred IUPAC name 2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate | |
| Other names [3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.000.987 |
| UNII | |
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| Properties | |
| C5H8N4O12 | |
| Molar mass | 316.137 g/mol |
| Appearance | White crystalline solid[1] |
| Density | 1.77 g/cm3 at 20 °C |
| Melting point | 141.3 °C (286.3 °F; 414.4 K) |
| Boiling point | 180 °C (356 °F; 453 K) (decomposes above 150 °C (302 °F)) |
| Explosive data | |
| Shock sensitivity | Medium |
| Friction sensitivity | Medium |
| Detonation velocity | 8400 m/s (density 1.7 g/cm3) |
| RE factor | 1.66 |
| Hazards | |
| GHS labelling: | |
   | |
| Danger | |
| H201,H241,H302,H316,H370,H373 | |
| P210,P250,P261,P264,P301+P312,P370+P380,P372,P401,P501 | |
| NFPA 704 (fire diamond) | |
| 190 °C (374 °F; 463 K) | |
| Pharmacology | |
| C01DA05 (WHO) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Pentaerythritol tetranitrate (PETN), also known asPENT,pentyl,PENTA (ПЕНТА, primarily in Russian),TEN (tetraeritrit nitrate),corpent, orpenthrite (or, rarely and primarily in German, asnitropenta), is anexplosive material. It is thenitrate ester ofpentaerythritol, and is structurally very similar tonitroglycerin.Penta refers to the fivecarbon atoms of theneopentane skeleton. PETN is a very powerful explosive material with arelative effectiveness factor of 1.66.[2] When mixed with aplasticizer, PETN forms aplastic explosive.[3] Along withRDX it is the main ingredient ofSemtex.
PETN is also used as avasodilator drug to treat certain heart conditions, such as for management ofangina.[4][5]
Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturerRheinisch-Westfälische Sprengstoff A.G. [de] ofCologne, Germany.[6][7][8][9] The production of PETN started in 1912, when the improved method of production was patented by the German government. PETN was used by the German Military inWorld War I.[10][11] It was also used in theMG FF/M autocannons and many other weapon systems of theLuftwaffe in World War II.[citation needed]
PETN is practicallyinsoluble in water (0.01 g/100 mL at 50 °C), weakly soluble in common nonpolarsolvents such asaliphatic hydrocarbons (like gasoline) ortetrachloromethane, but soluble in some other organic solvents, particularly inacetone (about 15 g/100 g of the solution at 20 °C, 55 g/100 g at 60 °C) anddimethylformamide (40 g/100 g of the solution at 40 °C, 70 g/100 g at 70 °C). It is a non-planar molecule that crystallizes in the space groupP421c.[12] PETN formseutectic mixtures with some liquid or moltenaromaticnitro compounds,e.g.trinitrotoluene (TNT) ortetryl. Due to the steric hindrance of the adjacent neopentyl-like moiety, PETN is resistant to attack by many chemicalreagents; it does nothydrolyze in water at room temperature or in weakeralkalineaqueous solutions. Water at 100 °C or above causeshydrolysis to dinitrate; the presence of 0.1%nitric acid accelerates the reaction.
Thechemical stability of PETN is of interest, because of the presence of PETN in aging weapons.[13]Neutron radiation degrades PETN, producingcarbon dioxide and some pentaerythritol dinitrate andtrinitrate.Gamma radiation increases thethermal decomposition sensitivity of PETN, lowers melting point by few degrees Celsius, and causes swelling of the samples. Like other nitrate esters, the primarydegradation mechanism is the loss ofnitrogen dioxide; this reaction isautocatalytic.[citation needed] Studies were performed onthermal decomposition of PETN.[14]
In the environment, PETN undergoesbiodegradation. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded.[15] PETN has lowvolatility and low solubility in water, and therefore has lowbioavailability for most organisms. Itstoxicity is relatively low, and itstransdermal absorption also seems to be low. It poses a threat for aquaticorganisms. It can be degraded to pentaerythritol byiron.[16]
Production is by the reaction ofpentaerythritol with concentratednitric acid to form a precipitate which can be recrystallized from acetone to give processable crystals.[17]
Variations of a method first published in US Patent 2,370,437 by Acken and Vyverberg (1945 to Du Pont) form the basis of all current commercial production.[citation needed]
PETN is manufactured by numerous manufacturers as a powder, or together withnitrocellulose andplasticizer as thin plasticized sheets (e.g.Primasheet 1000 orDetasheet). PETN residues are easily detectable in hair of people handling it.[18] The highest residue retention is on black hair; some residues remain even after washing.[19][20]
The most common use of PETN is as an explosive with highbrisance. It is asecondary explosive, meaning it is more difficult to detonate thanprimary explosives, so dropping or igniting it will typically not cause an explosion (atstandard atmospheric pressure it is difficult to ignite and burns vigorously), but is more sensitive to shock and friction than other secondary explosives such asTNT ortetryl.[17][21] Under certain conditions adeflagration to detonation transition can occur, just like that ofammonium nitrate.
It is rarely used alone in military operations due to its lower stability, but is primarily used in the main charges of plastic explosives (such asC4) along with other explosives (especiallyRDX),booster andbursting charges of smallcaliberammunition, in upper charges ofdetonators in someland mines and shells, as the explosive core ofdetonation cord.[22][23] PETN is the least stable of the common military explosives, but can be stored without significant deterioration for longer thannitroglycerin ornitrocellulose.[24]
DuringWorld War II, PETN was most importantly used inexploding-bridgewire detonators for the atomic bombs. These exploding-bridgewire detonators gave more precise detonation compared toprimacord. PETN was used for these detonators because it was safer than primary explosives likelead azide: while it was sensitive, it would not detonate below a threshold amount of energy.[25] Exploding bridgewires containing PETN remain used in current nuclear weapons. In spark detonators, PETN is used to avoid the need for primary explosives; the energy needed for a successful direct initiation of PETN by anelectric spark ranges between 10–60 mJ.
Its basic explosion characteristics are:
PETN is used in a number of compositions. It is a major ingredient of theSemtexplastic explosive. It is also used as a component ofpentolite, a castable mixture with TNT (usually 50/50 but may contain more TNT), which is, along with pure PETN, a common explosive for boosters for theblasting work (as inmining).[26][27] The XTX8003 extrudable explosive, used in theW68 andW76 nuclear warheads, is a mixture of 80% PETN and 20% of Sylgard 182, asilicone rubber.[28] It is oftenphlegmatized by addition of 5–40% ofwax, or by polymers (producingpolymer-bonded explosives); in this form it is used in some cannon shells up to30 mm caliber, though it is unsuitable for higher calibers. It is also used as a component of some gunpropellants andsolid rocket propellants. Nonphlegmatized PETN is stored and handled with approximately 10% water content. PETN alone cannot becast as it explosively decomposes slightly above its melting point,[citation needed][clarification needed] but it can be mixed with other explosives to form castable mixtures.
PETN can be initiated by alaser.[29] A pulse with duration of 25 nanoseconds and 0.5–4.2 joules of energy from aQ-switchedruby laser can initiate detonation of a PETN surface coated with a 100 nm thick aluminium layer in less than half of a microsecond.[citation needed]
PETN has been replaced in many applications byRDX, which is thermally more stable and has a longershelf life.[30] PETN can be used in someram accelerator types.[31] Replacement of the central carbon atom withsilicon produces Si-PETN, which is extremely sensitive.[32][33]
Ten kilograms of PETN was used in the1980 Paris synagogue bombing.
In 1983, 307 people were killed after a truck bomb filled with PETN was detonated at theBeirut barracks.
In 1983, the "Maison de France" house in Berlin was brought to a near-total collapse by the detonation of 24 kilograms (53 lb) of PETN by terroristJohannes Weinrich.[34]
In 1999,Alfred Heinz Reumayr used PETN as the main charge for his fourteenimprovised explosive devices that he constructed in a thwarted attempt to damage theTrans-Alaska Pipeline System.
In 2001,al-Qaeda memberRichard Reid, the "Shoe Bomber", used PETN in the sole of his shoe in his unsuccessful attempt to blow upAmerican Airlines Flight 63 from Paris to Miami.[20][35] He had intended to use the solidtriacetone triperoxide (TATP) as a detonator.[21]
In 2009, PETN was used in an attempt byal-Qaeda in the Arabian Peninsula to assassinate the Saudi Arabian Deputy Minister of Interior PrinceMuhammad bin Nayef, by Saudisuicide bomberAbdullah Hassan al Asiri. The target survived and the bomber died in the blast. The PETN was hidden in the bomber'srectum, which security experts described as a novel technique.[36][37][38]
On 25 December 2009, PETN was found in the underwear ofUmar Farouk Abdulmutallab, the "Underwear bomber", a Nigerian with links to al-Qaeda in the Arabian Peninsula.[39] According to US law enforcement officials,[40] he had attempted to blow upNorthwest Airlines Flight 253 while approaching Detroit from Amsterdam.[41] Abdulmutallab had tried, unsuccessfully, to detonate approximately 80 grams (2.8 oz) of PETN sewn into his underwear by adding liquid from a syringe;[42] however, only a small fire resulted.[21]
In the al-Qaeda in the Arabian Peninsula October2010 cargo plane bomb plot, two PETN-filled printer cartridges were found atEast Midlands Airport and inDubai on flights bound for the US on an intelligence tip. Both packages contained sophisticated bombs concealed in computerprinter cartridges filled with PETN.[43][44] The bomb found in England contained 400 grams (14 oz) of PETN, and the one found in Dubai contained 300 grams (11 oz) of PETN.[44] Hans Michels, professor ofsafety engineering atUniversity College London, told a newspaper that 6 grams (0.21 oz) of PETN—"around 50 times less than was used—would be enough to blast a hole in a metal plate twice the thickness of an aircraft's skin".[45] In contrast, according to an experiment conducted by a BBC documentary team designed to simulate Abdulmutallab's Christmas Day bombing, using a Boeing 747 plane, even 80 grams of PETN was not sufficient to materially damage the fuselage.[46]
On 12 July 2017, 150 grams of PETN was found in theAssembly of Uttar Pradesh,[47][48] India's most populous state.[49][50]
PETN was used by Israel in the manufacturing ofpagers provided toHezbollah. On September 17, 2024, the pagersdetonated, killing 12 people and injuring thousands.[51]
In the wake of terrorist PETN bomb plots, an article inScientific American noted PETN is difficult to detect because it does not readily vaporize into the surrounding air.[43] TheLos Angeles Times noted in November 2010 that PETN's lowvapor pressure makes it difficult for bomb-sniffing dogs to detect.[20]
Many technologies can be used to detect PETN, including chemical sensors, X-rays, infrared, microwaves[52] and terahertz,[53] some of which have been implemented in public screening applications, primarily for air travel. PETN is one of the explosive chemicals typically of interest in that area, and it belongs to a family of commonnitrate-based explosive chemicals which can often be detected by the same tests.
One detection system in use at airports involves analysis of swab samples obtained from passengers and their baggage. Whole-body imaging scanners that use radio-frequencyelectromagnetic waves, low-intensityX-rays, or T-rays of terahertz frequency that can detect objects hidden under clothing are not widely used because of cost, concerns about the resulting traveler delays, and privacy concerns.[54]
Both parcels in the 2010 cargo plane bomb plot were x-rayed without the bombs being spotted.[55]Qatar Airways said the PETN bomb "could not be detected by x-ray screening or trainedsniffer dogs".[56] TheBundeskriminalamt received copies of the Dubai x-rays, and an investigator said German staff would not have identified the bomb either.[55][57] New airport security procedures followed in the U.S., largely to protect against PETN.[20]
Likenitroglycerin (glyceryl trinitrate) and othernitrates, PETN is also used medically as avasodilator in the treatment ofheart conditions.[4][5] These drugs work by releasing the signaling gasnitric oxide in the body. The heart medicineLentonitrat is nearly pure PETN.[58]
Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma usinggas chromatography-mass spectrometry.[59]
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