Pentaerythritol tetranitrate
Names | |
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Preferred IUPAC name
2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate | |
Other names
[3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
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Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.000.987 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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Pentaerythritol tetranitrate (PETN), also known as PENT, pentyl, PENTA (ПЕНТА, primarily in Russian), TEN (tetraeritrit nitrate), corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an
PETN is also used as a vasodilator drug to treat certain heart conditions, such as for management of angina.[4][5]
History
Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturer Rheinisch-Westfälische Sprengstoff A.G. of Cologne, 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 in World War I.[10][11] It was also used in the MG FF/M autocannons and many other weapon systems of the Luftwaffe in World War II.
Properties
PETN is practically
The
In the environment, PETN undergoes biodegradation. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded.[14] PETN has low volatility and low solubility in water, and therefore has low bioavailability for most organisms. Its toxicity is relatively low, and its transdermal absorption also seems to be low.[1] It poses a threat for aquatic organisms. It can be degraded to pentaerythritol by iron.[15]
Production
Production is by the reaction of pentaerythritol with concentrated nitric acid to form a precipitate which can be recrystallized from acetone to give processable crystals.[16]
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.
PETN is manufactured by numerous manufacturers as a powder, or together with nitrocellulose and plasticizer as thin plasticized sheets (e.g. Primasheet 1000 or Detasheet). PETN residues are easily detectable in hair of people handling it.[17] The highest residue retention is on black hair; some residues remain even after washing.[18][19]
Explosive use
The most common use of PETN is as an explosive with high
It is rarely used alone in military operations due to its lower stability, but primarily used in main charges of plastic explosives such as
During
Its basic explosion characteristics are:
- Explosion energy: 5810 kJ/kg (1390 kcal/kg), so 1 kg of PETN has the energy of 1.24 kg TNT.
- Detonation velocity: 8350 m/s (1.73 g/cm3), 7910 m/s (1.62 g/cm3), 7420 m/s (1.5 g/cm3), 8500 m/s (pressed in a steel tube)
- Volume of gases produced: 790 dm3/kg (other value: 768 dm3/kg)
- Explosion temperature: 4230 °C
- Oxygen balance: −6.31 atom -g/kg
- Melting point: 141.3 °C (pure), 140–141 °C (technical)
- Trauzl lead block test: 523 cm3 (other values: 500 cm3 when sealed with sand, or 560 cm3 when sealed with water)
- Critical diameter (minimal diameter of a rod that can sustain detonation propagation): 0.9 mm for PETN at 1 g/cm3, smaller for higher densities (other value: 1.5 mm)
In mixtures
PETN is used in a number of compositions. It is a major ingredient of the
PETN can be initiated by a laser.[26] A pulse with duration of 25 nanoseconds and 0.5–4.2 joules of energy from a Q-switched ruby 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 by RDX, which is thermally more stable and has a longer shelf life.[27] PETN can be used in some ram accelerator types.[28] Replacement of the central carbon atom with silicon produces Si-PETN, which is extremely sensitive.[29][30]
Terrorist use
Ten kilograms of PETN was used in the 1980 Paris synagogue bombing.
In 1983, 307 people were killed after a truck bomb filled with PETN was detonated at the Beirut 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 terrorist Johannes Weinrich.[31]
In 1999, Alfred Heinz Reumayr used PETN as the main charge for his fourteen improvised explosive devices that he constructed in a thwarted attempt to damage the Trans-Alaska Pipeline System.
In 2001,
In 2009, PETN was used in an attempt by
On 25 December 2009, PETN was found in the underwear of Umar Farouk Abdulmutallab, the "Underwear bomber", a Nigerian with links to al-Qaeda in the Arabian Peninsula.[36] According to US law enforcement officials,[37] he had attempted to blow up Northwest Airlines Flight 253 while approaching Detroit from Amsterdam.[38] Abdulmutallab had tried, unsuccessfully, to detonate approximately 80 grams (2.8 oz) of PETN sewn into his underwear by adding liquid from a syringe;[39] however, only a small fire resulted.[20]
In the al-Qaeda in the Arabian Peninsula October
On 12 July 2017, 150 grams of PETN was found in the Assembly of Uttar Pradesh,[44][45] India's most populous state.[46][47]
Detection
In the wake of terrorist PETN bomb plots, an article in Scientific American noted PETN is difficult to detect because it does not readily vaporize into the surrounding air.[40] The Los Angeles Times noted in November 2010 that PETN's low vapor pressure makes it difficult for bomb-sniffing dogs to detect.[19]
Many technologies can be used to detect PETN, including chemical sensors, X-rays, infrared, microwaves[48] and terahertz,[49] 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 common nitrate-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-frequency
Both parcels in the 2010 cargo plane bomb plot were x-rayed without the bombs being spotted.
Medical use
Like
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 using
See also
- Erythritol tetranitrate
- RE factor
References
- ^ a b "Wildlife Toxicity Assessment for pentaerythritol tetranitrate" (PDF). U.S. Army Center for Health Promotion and Preventive Medicine. November 2001. Archived (PDF) from the original on October 9, 2022.
{{cite journal}}
: Cite journal requires|journal=
(help)[permanent dead link] - ^ "PETN (Pentaerythritol tetranitrate)". Retrieved March 29, 2010.
- ISBN 978-0-631-16848-5.
- ^ PMID 20325960.
- ^ ISBN 978-0-8493-9683-0.
- ^ Deutsches Reichspatent 81,664 (1894)
- ^ Thieme, Bruno "Process of making nitropentaerythrit," Archived July 11, 2021, at the Wayback Machine U.S. patent no. 541,899 (filed: November 13, 1894; issued: July 2, 1895).
- ^ Krehl, Peter O. K. (2009) History of Shock Waves, Explosions and Impact. Berlin, Germany: Springer-Verlag. p. 405.
- ^ Urbański, Tadeusz; Ornaf, Władysław and Laverton, Sylvia (1965) Chemistry and Technology of Explosives, vol. 2 (Oxford, England: Permagon Press. p. 175.
- ^ German Patent 265,025 (1912)
- ^ Stettbacher, Alfred (1933). Die Schiess- und Sprengstoffe (2. völlig umgearb. Aufl. ed.). Leipzig: Barth. p. 459.
- OSTI 966904. LLNL-TR-415057. Retrieved May 14, 2023.
- ^ German, V.N. et al. Thermal decomposition of PENT and HMX over a wide temperature range Archived April 10, 2020, at the Wayback Machine. Institute of Physics of Explosion, RFNC-VNIIEF, Sarov, Russia
- PMID 22647196.
- PMID 18605582.
- ^ ISBN 978-3527306732.
- ^ Winslow, Ron. (December 29, 2009) A Primer in PETN – WSJ.com. The Wall Street Journal. Retrieved 2010-02-08.
- PMID 16078483.
- ^ a b c d Bennett, Brian (November 24, 2010). "PETN: The explosive that airport security is targeting". Los Angeles Times. Tribune Washington Bureau. Retrieved July 19, 2015.
- ^ a b c Chang, Kenneth (December 27, 2009). "Explosive on Flight 253 Is Among Most Powerful". The New York Times.
- ^ "Primacord Technical Information" (PDF). Dyno Nobel. Archived from the original (PDF) on July 10, 2011. Retrieved April 22, 2009.
- PMID 33225129.
- ^ PETN (chemical compound). Encyclopædia Britannica. Retrieved February 8, 2010.
- ISBN 978-0-521-54117-6.
- OSTI 650196. SAND-97-8684C. Retrieved May 14, 2023.
- S2CID 98083192.
- ^ US Army – Encyclopedia of Explosives and Related Items, vol.8
- ^ Simulation of ram accelerator with PETN layer, Arkadiusz Kobiera and Piotr Wolanski, XXI ICTAM, August 15–21, 2004, Warsaw, Poland
- PMID 19489634. Archived from the original(PDF) on March 21, 2018. Retrieved January 3, 2010.
- ^ Computational Organic Chemistry » Si-PETN sensitivity explained. Comporgchem.com (July 20, 2009). Retrieved 2010-02-08.
- ^ "Article detailing attack on Maison de France in Berlin (German)". Der Spiegel. December 13, 1999. Retrieved November 4, 2010.
- ^ "'Shoe bomb suspect 'did not act alone'". BBC News. January 25, 2002. Retrieved April 22, 2009.
- ^ "Saudi suicide bomber hid IED in his anal cavity". Homeland Security Newswire. September 9, 2009. Archived from the original on December 31, 2009. Retrieved December 28, 2009.
- ^ England, Andrew (November 1, 2010). "Bomb clues point to Yemeni terrorists". Financial Times. Archived from the original on December 10, 2022.
- ^ "Saudi Bombmaker Key Suspect in Yemen Plot". CBS News. November 1, 2010. Archived from the original on November 2, 2012. Retrieved November 2, 2010.
- ^ "Al Qaeda Claims Responsibility for Attempted Bombing of U.S. Plane". FOX News Network. December 28, 2009. Retrieved December 29, 2009.
- The Huffington Post. Archived(PDF) from the original on October 9, 2022. Retrieved November 4, 2010.
- ^ "Investigators: Northwest Bomb Plot Planned by al Qaeda in Yemen". ABC News. December 26, 2009. Retrieved December 26, 2009.
- ^ Explosive in Detroit terror case could have blown hole in airplane, sources say The Washington Post. Retrieved February 8, 2010.
- ^ a b Greenemeier, Larry. "Exposing the Weakest Link: As Airline Passenger Security Tightens, Bombers Target Cargo Holds". Scientific American. Retrieved November 3, 2010.
- ^ a b Shane, Scott; Worth, Robert F. (November 1, 2010). "Early Parcels Sent to U.S. Were Eyed as Dry Run". The New York Times.
- ^ "Parcel bombs could rip 50 planes in half". India Today. Retrieved November 3, 2010.
- ^ "'Underwear Bomber' Could not have Blown Up Plane". Discovery. March 10, 2010. Archived from the original on October 13, 2010. Retrieved November 16, 2010.
- ^ "What is PETN explosive device found in Uttar Pradesh Assembly?". July 15, 2017.
- ^ "Highly explosive PETN found in Uttar Pradesh Assembly: Yogi Adityanath demands NIA probe". July 14, 2017.
- ^ "Population and decadal change by residence : 2011 (PERSONS)" (PDF). Office of the Registrar General & Census Commissioner, India. p. 2. Archived (PDF) from the original on October 9, 2022.
- ^ "Statistical Year Book 2015" (PDF). telangana.gov.in. Directorate of Economics and Statistics, Government of Telangana. Archived (PDF) from the original on October 9, 2022. Retrieved March 4, 2019.
- ^ Committee on the Review of Existing and Potential Standoff Explosives Detection Techniques, National Research Council (2004) Existing and Potential Standoff Explosives Detection Techniques, National Academies Press, Washington, D.C. p. 77.
- S2CID 137950290.
- ^ "Equipment to detect explosives is available". The Washington Post. Retrieved February 8, 2010.
- ^ a b "Foiled Parcel Plot: World Scrambles to Tighten Air Cargo Security". Der Spiegel. Retrieved November 2, 2010.
- ^ "Q&A: Air freight bomb plot". BBC News. October 30, 2010. Retrieved November 3, 2010.
- ^ "Passenger jets carried Dubai bomb". Al Jazeera. October 31, 2010.
- S2CID 30975527.
- ISBN 0962652369.
Further reading
- Cooper, Paul (1997). Explosives Engineering. Weinheim: Wiley-VCH. ISBN 978-0-471-18636-6.