Editing Pentaerythritol tetranitrate

{{Short description|Explosive chemical compound}}
{{redirect|PETN|the wind power station| Taiba N'Diaye Wind Power Station}}
{{Use mdy dates|date=November 2015}}
{{chembox
| Watchedfields  = changed
| verifiedrevid  = 477001336
| Name           = 
| ImageFile      = 
| ImageFile1     = PETN.svg
| ImageAlt1      = Skeletal formula
| ImageFile2     = PETN-from-xtal-2006-3D-balls-B.png
| ImageAlt2      = Ball-and-stick model
| ImageFile3     = Pentaerythritol tetranitrate 05.jpg
| ImageAlt3      = Pentaerythritol tetranitrate after crystalization from acetone
| ImageSize3     = 235px
| PIN            = 2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate
| SystematicName = 
| OtherNames     = [3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
| IUPACName      = 
| Section1       = {{Chembox Identifiers
 | CASNo = 78-11-5
 | CASNo_Ref = {{cascite|correct|CAS}}
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 10L39TRG1Z
 | PubChem = 6518
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 6271
 | ChEMBL_Ref = {{ebicite|correct|EBI}}
 | ChEMBL = 466659
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = TZRXHJWUDPFEEY-UHFFFAOYSA-N
 | SMILES = C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
 | InChI = InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
 }}
| Section2       = {{Chembox Properties
 | C=5 | H=8 | N=4 | O=12
 | Appearance = White crystalline solid<ref name=epa1>{{Cite web |url=https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf |archive-url=https://web.archive.org/web/20240801034435/https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf |archive-date=2024-08-01 |url-status=live|title=Provisional Peer-Reviewed Toxicity Values for Pentaerythritol Tetranitrate (PETN) (CASRN 78-11-5)|date=July 2021|publisher=United States Environmental Protection Agency}}</ref>
 | MolarMass = 316.137 g/mol
 | Density = 1.77 g/cm<sup>3</sup> at 20 °C
 | MeltingPtC = 141.3
 | BoilingPtC = 180
 | BoilingPt_notes = (decomposes above {{convert|150|C|F}})
 | Solubility =
 }}
| Section3       = {{Chembox Explosive
 | ShockSens = Medium
 | FrictionSens = Medium
 | DetonationV = 8400 m/s (density 1.7 g/cm<sup>3</sup>)
 | REFactor = 1.66}}
| Section4       = {{Chembox Hazards
 | GHSPictograms = {{GHS06}} {{GHS01}} {{GHS health hazard}}
 | GHSSignalWord = '''Danger'''
 | HPhrases = {{H-phrases|201|302|316|370|373|241}}
 | PPhrases = {{P-phrases|210|250|261|264|301+312|372|401|501|370+380}}
 | NFPA-F = 1
 | NFPA-H = 2
 | NFPA-R = 3
 | FlashPt =
 | AutoignitionPtC = 190
 }}
| Section5       = {{Chembox Pharmacology
 | ATCCode_prefix = C01
 | ATCCode_suffix = DA05
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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 [[explosive]] material. It is the [[nitrate ester]] of [[pentaerythritol]], and is structurally very similar to [[nitroglycerin]]. [[Penta-|Penta]] refers to the five [[carbon atom]]s of the [[neopentane]] skeleton. PETN is a very powerful explosive material with a [[relative effectiveness factor]] of 1.66.<ref name="urlPETN [Pentaerythritol tetranitrate]">{{cite web |url= http://www.globalsecurity.org/military/systems/munitions/explosives-nitrate-petn.htm |title=PETN (Pentaerythritol tetranitrate) |access-date=March 29, 2010}}</ref> When mixed with a [[plasticizer]], PETN forms a [[plastic explosive]].<ref>{{cite encyclopedia |title = Explosives |encyclopedia = A dictionary of military history and the art of war |last= Childs |first= John |url = https://books.google.com/books?id=nEQ7FUAdmc8C&pg=PA231 |format = [[Google Books]] extract |isbn = 978-0-631-16848-5 |year = 1994}}</ref> Along with [[RDX]] it is the main ingredient of [[Semtex]].

PETN is also used as a [[Vasodilation|vasodilator]] drug to treat certain heart conditions, such as for management of [[angina]].<ref name = newdrugs>{{cite journal |pmc = 1831125 |title = New Drugs |journal = [[Can Med Assoc J]] |year = 1959 |volume = 80 |pages = 997–998 |pmid=20325960 |issue=12}}</ref><ref name = ebadi>{{cite book |title = CRC desk reference of clinical pharmacology |page = 383 |author = Ebadi, Manuchair S. |year = 1998 |publisher = CRC Press |isbn = 978-0-8493-9683-0 |url = https://books.google.com/books?id=-EAxShTKfGAC&pg=PA383 |format = [[Google Books]] excerpt}}</ref>

==History==
Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturer {{Interlanguage link|RWS (company)|lt=Rheinisch-Westfälische Sprengstoff A.G.|de|RWS (Unternehmen)}} of [[Cologne|Cologne, Germany]].<ref>Deutsches Reichspatent 81,664 (1894)</ref><ref>Thieme, Bruno [http://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541,899.PN.%2526OS%3DPN%2F0541,899%2526RS%3DPN%2F0541,899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page "Process of making nitropentaerythrit,"] {{Webarchive|url=https://web.archive.org/web/20210711151323/https://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541%2C899.PN.%2526OS%3DPN%2F0541%2C899%2526RS%3DPN%2F0541%2C899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page |date=July 11, 2021 }} U.S. patent no. 541,899 (filed:  November 13, 1894; issued:  July 2, 1895).</ref><ref>Krehl, Peter O. K. (2009) ''History of Shock Waves, Explosions and Impact''. Berlin, Germany: Springer-Verlag. [https://books.google.com/books?id=PmuqCHDC3pwC&pg=PA405 p. 405].</ref><ref>Urbański, Tadeusz; Ornaf, Władysław and Laverton, Sylvia (1965) ''Chemistry and Technology of Explosives'', vol. 2 (Oxford, England:  Permagon Press. [https://archive.org/stream/ChemistryAndTechnologyOfExplosives-VolumeIi/ChemistryAndTechnologyOfExplosives-VolumeIi-TadeuszUrbanski#page/n183/mode/2up p. 175.]
</ref> 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 {{nowrap|[[World War I]]}}.<ref>German Patent 265,025 (1912)</ref><ref>{{cite book|title = Die Schiess- und Sprengstoffe|author = Stettbacher, Alfred |place = Leipzig |publisher= Barth|year = 1933| page= 459| edition = 2. völlig umgearb. Aufl. }}</ref> It was also used in the [[MG FF cannon|MG FF/M autocannons]] and many other weapon systems of the [[Luftwaffe]] in World War II.{{cn|date=September 2024}}

==Properties==
PETN is practically [[solubility|insoluble]] in water (0.01&nbsp;g/100&nbsp;mL at 50&nbsp;°C), weakly soluble in common nonpolar [[solvent]]s such as [[Aliphatic compound|aliphatic hydrocarbon]]s (like gasoline) or [[Carbon tetrachloride|tetrachloromethane]], but soluble in some other organic solvents, particularly in [[acetone]] (about 15&nbsp;g/100&nbsp;g of the solution at 20&nbsp;°C, 55&nbsp;g/100&nbsp;g at 60&nbsp;°C) and [[dimethylformamide]] (40&nbsp;g/100&nbsp;g of the solution at 40&nbsp;°C, 70&nbsp;g/100&nbsp;g at 70&nbsp;°C). It is a non-planar molecule that crystallizes in the space group ''P''{{overline|4}}2<sub>1</sub>''c''.<ref>{{cite journal|author=Zhurova, Elizabeth A.; Stash, Adam I.; Tsirelson, Vladimir G.; Zhurov, Vladimir V.; Bartashevich, Ekaterina V.; Potemkin, Vladimir A.; Pinkerton, A. Alan|year=2006|title=Atoms-in-Molecules Study of Intra- and Intermolecular Bonding in the Pentaerythritol Tetranitrate Crystal|journal=Journal of the American Chemical Society|volume=128|issue=45|pages=14728–14734|doi=10.1021/ja0658620|pmid=17090061 |bibcode=2006JAChS.12814728Z }}</ref> PETN forms [[eutectic system|eutectic]] mixtures with some liquid or molten [[aromaticity|aromatic]] [[nitro compound]]s, ''e.g.'' [[trinitrotoluene]] (TNT) or [[tetryl]]. Due to the steric hindrance of the adjacent neopentyl-like moiety, PETN is resistant to attack by many chemical [[reagent]]s; it does not [[hydrolysis|hydrolyze]] in water at room temperature or in weaker [[alkalinity|alkaline]] [[aqueous solution]]s. Water at 100&nbsp;°C or above causes [[hydrolysis]] to dinitrate; the presence of 0.1% [[nitric acid]] accelerates the reaction.

The [[chemical stability]] of PETN is of interest, because of the presence of PETN in aging weapons.<ref>{{Cite tech report | title = Aging of Pentaerythritol Tetranitrate (PETN) | url = https://www.osti.gov/servlets/purl/966904 | last = Foltz | first = M. F. | institution = [[Lawrence Livermore National Laboratory]] | date = July 27, 2009 | number = LLNL-TR-415057 | osti = 966904 | access-date = May 14, 2023 }}</ref> [[Neutron radiation]] degrades PETN, producing [[carbon dioxide]] and some pentaerythritol dinitrate and [[Nitrate|trinitrate]]. [[Gamma radiation]] increases the [[thermal decomposition]] sensitivity of PETN, lowers melting point by few degrees Celsius, and causes swelling of the samples. Like other nitrate esters, the primary [[Chemical decomposition|degradation]] mechanism is the loss of [[nitrogen dioxide]]; this reaction is [[autocatalytic]].{{Citation needed|date=November 2010}} Studies were performed on [[thermal decomposition]] of PETN.<ref>German, V.N. et al. [http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf Thermal decomposition of PENT and HMX over a wide temperature range] {{Webarchive|url=https://web.archive.org/web/20200410211224/http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf |date=April 10, 2020 }}. Institute of Physics of Explosion,  RFNC-VNIIEF, Sarov, Russia</ref>

In the environment, PETN undergoes [[biodegradation]]. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded.<ref>{{Cite journal|last1=Zhuang|first1=Li|last2=Gui|first2=Lai|last3=Gillham|first3=Robert W.|date=2012-10-01|title=Biodegradation of pentaerythritol tetranitrate (PETN) by anaerobic consortia from a contaminated site|url=http://www.sciencedirect.com/science/article/pii/S0045653512005942|journal=Chemosphere|language=en|volume=89|issue=7|pages=810–816|doi=10.1016/j.chemosphere.2012.04.062|pmid=22647196|bibcode=2012Chmsp..89..810Z|issn=0045-6535}}</ref> PETN has low [[Volatility (chemistry)|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. It poses a threat for aquatic [[organism]]s. It can be degraded to pentaerythritol by [[iron]].<ref>{{cite journal|doi=10.1021/es7029703|title=Degradation of Pentaerythritol Tetranitrate (PETN) by Granular Iron|journal=[[Environ. Sci. Technol.]]|year=2008|volume=42|pages=4534–9|pmid=18605582|issue=12|last1=Zhuang|first1=L|last2=Gui|first2=L|last3=Gillham|first3=R. W.|bibcode=2008EnST...42.4534Z}}</ref>

==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.<ref name = Ullmann>{{Ullmann | doi = 10.1002/14356007.a10_143.pub2 | title = Explosives | author = Boileau, Jacques | author2 = Fauquignon, Claude | author3 = Hueber, Bernard | author4 = Meyer, Hans H. | name-list-style=amp }}</ref>

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.{{cn|date=September 2024}}

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.<ref>Winslow, Ron. (December 29, 2009) [https://www.wsj.com/articles/SB126195987401406861 A Primer in PETN – WSJ.com]. ''The Wall Street Journal''. Retrieved 2010-02-08.</ref> The highest residue retention is on black hair; some residues remain even after washing.<ref>{{cite journal | last1 = Oxley | first1 = Jimmie C. | last2 = Smith | first2 = James L. | last3 = Kirschenbaum | first3 = Louis J. | last4 = Shinde | first4 = Kajal. P. | last5 = Marimganti | first5 = Suvarna | title = Accumulation of Explosives in Hair | journal = Journal of Forensic Sciences | volume = 50 | issue = 4 | year = 2005 | pages = 826–31 | doi = 10.1520/JFS2004545| pmid = 16078483 }}</ref><ref name="latimes.com">{{cite news| url=https://www.latimes.com/archives/la-xpm-2010-nov-24-la-na-petn-20101124-story.html |title= PETN: The explosive that airport security is targeting |last=Bennett |first=Brian |agency=Tribune Washington Bureau |date=November 24, 2010 |work=Los Angeles Times |access-date=July 19, 2015}}</ref>

==Explosive use==

[[File:Pentryt.jpg|thumbnail|Pentaerythritol tetranitrate before crystallization from acetone]]

The most common use of PETN is as an explosive with high [[brisance]]. It is a [[secondary explosive]], meaning it is more difficult to detonate than [[primary explosive]]s, so dropping or igniting it will typically not cause an explosion (at [[standard atmospheric pressure]] it is difficult to ignite and burns vigorously), but is more sensitive to shock and friction than other secondary explosives such as [[TNT]] or [[tetryl]].<ref name = Ullmann/><ref name=nyt>{{Cite news|url=https://www.nytimes.com/2009/12/28/us/28explosives.html?ref=us|title=Explosive on Flight 253 Is Among Most Powerful |newspaper=The New York Times|date=December 27, 2009|author=Chang, Kenneth }}</ref> Under certain conditions a [[deflagration to detonation transition]] can occur, just like that of [[ammonium 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 as [[C-4 (explosive)|C4]]) along with other explosives (especially [[RDX]]), [[explosive booster|booster]] and [[burst charge|bursting charges]] of small [[caliber]] [[ammunition]], in upper charges of [[detonator]]s in some [[land mine]]s and shells, as the explosive core of [[detonation cord]].<ref name="urlwww.dynonobel.com">{{cite web|url=http://www.dynonobel.com/files/2010/04/Primacord.pdf |title=Primacord Technical Information |publisher=Dyno Nobel |access-date=April 22, 2009 |url-status=dead |archive-url=https://web.archive.org/web/20110710160725/http://www.dynonobel.com/files/2010/04/Primacord.pdf |archive-date=July 10, 2011 }}</ref><ref>{{Cite journal |title=Explosive power of Pentaerythritol Tetranitrate |date=2020 |pmc=7675531 |last1=Zhang |first1=Y. |last2=Li |first2=Q. |last3=He |first3=Y. |journal=ACS Omega |volume=5 |issue=45 |pages=28984–28991 |doi=10.1021/acsomega.0c03133 |pmid=33225129 }}</ref> PETN is the least stable of the common military explosives, but can be stored without significant deterioration for longer than [[nitroglycerin]] or [[nitrocellulose]].<ref>[http://www.britannica.com/EBchecked/topic/454067/PETN PETN (chemical compound)]. ''Encyclopædia Britannica''. Retrieved February 8, 2010.</ref>

During [[World War II]], PETN was most importantly used in [[exploding-bridgewire detonator]]s for the atomic bombs. These exploding-bridgewire detonators gave more precise detonation compared to [[primacord]]. PETN was used for these detonators because it was safer than primary explosives like [[lead azide]]: while it was sensitive, it would not detonate below a threshold amount of energy.<ref>{{cite book | title = A Technical History of Los Alamos During the Oppenheimer Years, 1943–1945 |author1=Lillian Hoddeson |author2=Paul W. Henriksen |author3=Roger A. Meade |author4=Catherine L. Westfall |author5=Gordon Baym |author6=Richard Hewlett |author7=Alison Kerr |author8=Robert Penneman |author9=Leslie Redman |author10=Robert Seidel | year = 2004 | pages = 164–173 |publisher=Cambridge University Press | url = https://books.google.com/books?id=KoTve97yYB8C&pg=PA164 | format = [[Google Books]] excerpt | isbn = 978-0-521-54117-6}}</ref> 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 an [[electric spark]] ranges between 10–60 mJ.

Its basic explosion characteristics are:
* Explosion energy: 5810 kJ/kg (1390 kcal/kg), so 1&nbsp;kg of PETN has the energy of 1.24&nbsp;kg TNT.
* [[Detonation velocity]]: 8350&nbsp;m/s (1.73 g/cm<sup>3</sup>), 7910&nbsp;m/s (1.62 g/cm<sup>3</sup>), 7420&nbsp;m/s (1.5 g/cm<sup>3</sup>), 8500&nbsp;m/s (pressed in a steel tube)
* Volume of gases produced: 790 dm<sup>3</sup>/kg (other value: 768 dm<sup>3</sup>/kg)
* Explosion temperature: 4230&nbsp;°C
* [[Oxygen balance]]: −6.31 atom -g/kg
* [[Melting point]]: 141.3&nbsp;°C (pure), 140–141&nbsp;°C (technical)
* [[Trauzl lead block test]]: 523&nbsp;cm<sup>3</sup> (other values: 500&nbsp;cm<sup>3</sup> when sealed with sand, or 560&nbsp;cm<sup>3</sup> when sealed with water)
* Critical diameter (minimal diameter of a rod that can sustain detonation propagation): 0.9&nbsp;mm for PETN at 1 g/cm<sup>3</sup>, smaller for higher densities (other value: 1.5&nbsp;mm)

===In mixtures===
PETN is used in a number of compositions. It is a major ingredient of the [[Semtex]] [[plastic explosive]]. It is also used as a component of [[pentolite]], 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 the [[Drilling and blasting|blasting work]] (as in [[mining]]).<ref>{{Cite book |last=Kennedy |first=Bruce A. |url=https://books.google.com/books?id=qJJrYnpT2pYC&pg=PA547 |title=Surface Mining, Second Edition |date=1990 |publisher=SME |isbn=978-0-87335-102-7 |pages=547 |language=en}}</ref><ref>{{Cite book |last=Rustan |first=Agne |url=https://books.google.com/books?id=idsQOABCipMC&pg=PA33 |title=Rock Blasting Terms and Symbols: A Dictionary of Symbols and Terms in Rock Blasting and Related Areas like Drilling, Mining and Rock Mechanics |date=1998 |publisher=CRC Press |isbn=978-90-5410-441-4 |pages=33 |language=en}}</ref> The XTX8003 extrudable explosive, used in the [[W68]] and [[W76]] nuclear warheads, is a mixture of 80% PETN and 20% of Sylgard 182, a [[silicone rubber]].<ref>{{cite tech report |last1=Shepodd | first1=T | last2=Behrens | first2=R | last3=Anex | first3=D | last4=Miller | first4=D | last5=Anderson | first5=K |date=1997-07-01 |title= Degradation chemistry of PETN and its homologues |institution= Sandia National Laboratory |number= SAND-97-8684C | osti=650196 | url=https://www.osti.gov/servlets/purl/650196 | access-date= May 14, 2023}}</ref> It is often [[phlegmatized]] by addition of 5–40% of [[wax]], or by polymers (producing [[polymer-bonded explosive]]s); in this form it is used in some cannon shells up to [[30 mm caliber]], though it is unsuitable for higher calibers. <!-- why? --> It is also used as a component of some gun [[propellant]]s and [[solid rocket propellant]]s. Nonphlegmatized PETN is stored and handled with approximately 10% water content. PETN alone cannot be [[casting|cast]] as it explosively decomposes slightly above its melting point,{{citation needed|date=September 2016}}{{clarify|date=September 2016}} but it can be mixed with other explosives to form castable mixtures.

PETN can be initiated by a [[laser]].<ref>{{cite journal | last1 = Tarzhanov | first1 = V. I. | last2 = Zinchenko | first2 = A. D. | last3 = Sdobnov | first3 = V. I. | last4 = Tokarev | first4 = B. B. | last5 = Pogrebov | first5 = A. I. | last6 = Volkova | first6 = A. A. | title = Laser initiation of PETN | journal = Combustion, Explosion, and Shock Waves | volume = 32 | issue = 4 | page = 454 | year = 1996 | doi = 10.1007/BF01998499| bibcode = 1996CESW...32..454T | s2cid = 98083192 }}</ref> A pulse with duration of 25 nanoseconds and 0.5–4.2 joules of energy from a [[Q-switching|Q-switched]] [[ruby laser]] can initiate detonation of a PETN surface coated with a 100&nbsp;nm thick aluminium layer in less than half of a microsecond.{{Citation needed|date=November 2010}}

PETN has been replaced in many applications by [[RDX]], which is thermally more stable and has a longer [[shelf life]].<ref>US Army – Encyclopedia of Explosives and Related Items, vol.8</ref> PETN can be used in some [[ram accelerator]] types.<ref>[http://fluid.ippt.gov.pl/ictam04/CD_ICTAM04/FM3/12843/FM3_12843.pdf Simulation of ram accelerator with PETN layer], Arkadiusz Kobiera and Piotr Wolanski, XXI ICTAM, August 15–21, 2004, Warsaw, Poland</ref> Replacement of the central carbon atom with [[silicon]] produces Si-PETN, which is extremely sensitive.<ref>{{cite journal|url=http://www.wag.caltech.edu/publications/sup/pdf/806.pdf|title=Explanation of the Colossal Detonation Sensitivity of Silicon Pentaerythritol Tetranitrate (Si-PETN) Explosive|author=Wei-Guang Liu|journal=J. Am. Chem. Soc.|year=2009|volume=131|pages=7490–1|doi=10.1021/ja809725p|pmid=19489634|issue=22|bibcode=2009JAChS.131.7490L |display-authors=etal|access-date=January 3, 2010|archive-date=March 21, 2018|archive-url=https://web.archive.org/web/20180321192503/http://www.wag.caltech.edu/publications/sup/pdf/806.pdf|url-status=dead}}</ref><ref>[http://comporgchem.com/blog/?p=258 Computational Organic Chemistry » Si-PETN sensitivity explained]. Comporgchem.com (July 20, 2009). Retrieved 2010-02-08.</ref>

===Terrorist and Military use===
{{Main|Shoe Bomber|2009 Christmas Day bomb plot|2010 cargo plane bomb plot}}

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 [[1983 Beirut barracks bombings|Beirut barracks]].

In 1983, the "Maison de France" house in Berlin was brought to a near-total collapse by the detonation of {{convert|24|kg|lb}} of PETN by terrorist [[Johannes Weinrich]].<ref>{{cite news|url=http://www.spiegel.de/panorama/0,1518,56218,00.html |title=Article detailing attack on Maison de France in Berlin (German) |work=Der Spiegel |date=December 13, 1999 |access-date=November 4, 2010}}</ref>

In 1999, [[Alfred Heinz Reumayr]] used PETN as the main charge for his fourteen [[improvised explosive device]]s that he constructed in a thwarted attempt to damage the [[Trans-Alaska Pipeline System]].

In 2001, [[al-Qaeda]] member [[Richard Reid (shoe bomber)|Richard Reid]], the "Shoe Bomber", used PETN in the sole of his shoe in his unsuccessful attempt to blow up [[2001 American Airlines Flight 63 bombing attempt|American Airlines Flight 63]] from Paris to Miami.<ref name="latimes.com"/><ref name="urlBBC News|AMERICAS|Shoe bomb suspect did not act alone">{{cite news|url = http://news.bbc.co.uk/2/hi/americas/1783237.stm|title = 'Shoe bomb suspect 'did not act alone'|date = January 25, 2002|work = BBC News|access-date = April 22, 2009}}</ref> He had intended to use the solid [[triacetone triperoxide]] (TATP) as a detonator.<ref name=nyt/>

In 2009, PETN was used in an attempt by [[al-Qaeda in the Arabian Peninsula]] to assassinate the Saudi Arabian Deputy Minister of Interior Prince [[Muhammad bin Nayef]], by Saudi [[suicide bomber]] [[Abdullah Hassan Al Aseery|Abdullah Hassan al Asiri]]. The target survived and the bomber died in the blast. The PETN was hidden in the bomber's [[rectum]], which security experts described as a novel technique.<ref>{{cite web|url=http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity|title=Saudi suicide bomber hid IED in his anal cavity|date=September 9, 2009|work=Homeland Security Newswire|access-date=December 28, 2009|archive-url=https://web.archive.org/web/20091231030044/http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity|archive-date=December 31, 2009|url-status=dead}}</ref><ref>{{cite web|url=https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0 |archive-url=https://ghostarchive.org/archive/20221210/https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0 |archive-date=December 10, 2022 |url-status=live|author=England, Andrew |title= Bomb clues point to Yemeni terrorists |work=Financial Times |date=November 1, 2010 |url-access=subscription}}</ref><ref>{{cite news |url=https://www.cbsnews.com/news/saudi-bombmaker-key-suspect-in-yemen-plot/ |title=Saudi Bombmaker Key Suspect in Yemen Plot |publisher=CBS News |date=November 1, 2010 |access-date=November 2, 2010 |archive-date=November 2, 2012 |archive-url=https://web.archive.org/web/20121102214722/http://www.cbsnews.com/stories/2010/11/01/world/main7010288.shtml |url-status=live }}</ref>

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.<ref>
{{cite news
| url = http://www.foxnews.com/story/0,2933,581307,00.html
| archive-url = https://web.archive.org/web/20091231020948/http://www.foxnews.com/story/0,2933,581307,00.html
| url-status = dead
| archive-date = December 31, 2009
| title = Al Qaeda Claims Responsibility for Attempted Bombing of U.S. Plane
| date = December 28, 2009
| publisher = FOX News Network
| access-date = December 29, 2009}}</ref> According to US law enforcement officials,<ref>{{cite news|url=http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf |archive-url=https://ghostarchive.org/archive/20221009/http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf |archive-date=2022-10-09 |url-status=live |title=Criminal Complaint |access-date=November 4, 2010 |work=[[The Huffington Post]]}}</ref> he had attempted to blow up [[Northwest Airlines Flight 253]] while approaching Detroit from Amsterdam.<ref name="urlABC News|AMERICAS|Investigators: Northwest Bomb Plot Planned by Al-Qaeda in Yemen">{{cite web|url = https://abcnews.go.com/Blotter/northwest-bomb-plot-planned-al-qaeda-yemen/story?id=9426085&page=1|title = Investigators: Northwest Bomb Plot Planned by al Qaeda in Yemen|date = December 26, 2009|publisher = ABC News|access-date = December 26, 2009}}</ref> Abdulmutallab had tried, unsuccessfully, to detonate approximately {{convert|80|g}} of PETN sewn into his underwear by adding liquid from a syringe;<ref>[https://www.washingtonpost.com/wp-dyn/content/article/2009/12/28/AR2009122800582.html Explosive in Detroit terror case could have blown hole in airplane, sources say] ''The Washington Post''. Retrieved February 8, 2010.</ref> however, only a small fire resulted.<ref name=nyt/>

In the al-Qaeda in the Arabian Peninsula October [[2010 cargo plane bomb plot]], two PETN-filled printer cartridges were found at [[East Midlands Airport]] and in [[Dubai]] on flights bound for the US on an intelligence tip. Both packages contained sophisticated bombs concealed in computer [[Toner cartridge|printer cartridges]] filled with PETN.<ref name="scientificamerican1">{{cite web|last=Greenemeier |first=Larry |url=http://www.scientificamerican.com/article.cfm?id=aircraft-cargo-bomb-security |title=Exposing the Weakest Link: As Airline Passenger Security Tightens, Bombers Target Cargo Holds |work=Scientific American |access-date=November 3, 2010}}</ref><ref name="nytimes4">{{cite news| url=https://www.nytimes.com/2010/11/02/world/02terror.html?src=twrhp | work=The New York Times | first1=Scott | last1=Shane | first2=Robert F. | last2=Worth | title=Early Parcels Sent to U.S. Were Eyed as Dry Run | date=November 1, 2010}}</ref> The bomb found in England contained {{convert|400|g}} of PETN, and the one found in Dubai contained {{convert|300|g}} of PETN.<ref name="nytimes4"/> Hans Michels, professor of [[safety engineering]] at [[University College London]], told a newspaper that {{convert|6|g}} 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".<ref>{{cite news |url=http://indiatoday.intoday.in/site/Story/118746/World/parcel-bombs-could-rip-50-planes-in-half.html |title=Parcel bombs could rip 50 planes in half |work=[[India Today]] |access-date=November 3, 2010}}</ref> 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&nbsp;grams of PETN was not sufficient to materially damage the fuselage.<ref>{{cite web |url=http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html |title='Underwear Bomber' Could not have Blown Up Plane |publisher=[[Discovery Channel|Discovery]] |date=March 10, 2010 |access-date=November 16, 2010 |archive-date=October 13, 2010 |archive-url=https://web.archive.org/web/20101013011037/http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html |url-status=dead }}</ref>

On 12 July 2017, 150 grams of PETN was found in the [[Uttar Pradesh Legislative Assembly|Assembly of Uttar Pradesh]],<ref>{{Cite web|url=https://indianexpress.com/article/what-is/what-is-petn-explsoive-uttar-pradesh-assembly-yogi-adityanath-4750049/|title = What is PETN explosive device found in Uttar Pradesh Assembly?|date = July 15, 2017}}</ref><ref>{{Cite web|url=http://www.firstpost.com/india/highly-explosive-petn-found-in-uttar-pradesh-assembly-yogi-adityanath-chairs-high-level-meet-demands-nia-probe-3812119.html|title = Highly explosive PETN found in Uttar Pradesh Assembly: Yogi Adityanath demands NIA probe|date = July 14, 2017}}</ref> India's most populous state.<ref>{{cite web |title=Population and decadal change by residence : 2011 (PERSONS) |url=http://www.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf |archive-url=https://ghostarchive.org/archive/20221009/http://www.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf |archive-date=2022-10-09 |url-status=live |publisher=Office of the Registrar General & Census Commissioner, India |page=2}}</ref><ref>{{cite web |title=Statistical Year Book 2015 |url=https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf |archive-url=https://ghostarchive.org/archive/20221009/https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf |archive-date=2022-10-09 |url-status=live |website=telangana.gov.in |publisher=Directorate of Economics and Statistics, Government of Telangana |access-date=4 March 2019}}</ref>

PETN was used by Israel in the manufacturing of [[pager]]s provided to [[Hezbollah]]. On September 17, 2024, the pagers [[2024 Lebanon pager explosions|detonated]], killing 12 people and injuring thousands.<ref>{{Cite web |last1=Gebeily |first1=Maya |last2=Pearson |first2=James |last3=Gauthier-Villars |first3=David |date=October 16, 2024 |title=How Israel's bulky pager fooled Hezbollah |url=https://www.reuters.com/graphics/ISRAEL-PALESTINIANS/HEZBOLLAH-PAGERS/mopawkkwjpa/ |access-date=October 16, 2024 |publisher=[[Reuters]]}}</ref>

===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.<ref name="scientificamerican1"/> The ''[[Los Angeles Times]]'' noted in November 2010 that PETN's low [[vapor pressure]] makes it difficult for bomb-sniffing dogs to detect.<ref name="latimes.com"/>

Many technologies can be used to detect PETN, including chemical sensors, X-rays, infrared, microwaves<ref>Committee on the Review of Existing and Potential Standoff Explosives Detection Techniques, National Research Council (2004) [http://www.nap.edu/openbook.php?record_id=10998&page=1 Existing and Potential Standoff Explosives Detection Techniques], National Academies Press, Washington, D.C. p. 77.</ref> and terahertz,<ref>{{cite book|doi=10.1117/12.2197442|chapter=Discrimination and identification of RDX/PETN explosives by chemometrics applied to terahertz time-domain spectral imaging|title=Millimetre Wave and Terahertz Sensors and Technology VIII|volume=9651|pages=965109|year=2015|last1=Bou-Sleiman|first1=J.|last2=Perraud|first2=J.-B.|last3=Bousquet|first3=B.|last4=Guillet|first4=J.-P.|last5=Palka|first5=N.|last6=Mounaix|first6=P.|s2cid=137950290|editor1-last=Salmon|editor1-first=Neil A|editor2-last=Jacobs|editor2-first=Eddie L}}</ref> 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 [[Nitro compound|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 [[electromagnetic wave]]s, low-intensity [[X-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.<ref>[https://www.washingtonpost.com/wp-dyn/content/article/2009/12/27/AR2009122702021.html "Equipment to detect explosives is available"]. ''[[The Washington Post]]''. Retrieved February 8, 2010.</ref>

Both parcels in the 2010 cargo plane bomb plot were x-rayed without the bombs being spotted.<ref name="spiegel1"/> [[Qatar Airways]] said the PETN bomb "could not be detected by x-ray screening or trained [[sniffer dog]]s".<ref name="autogenerated1">{{cite news|url=https://www.bbc.co.uk/news/11658452 |title=Q&A: Air freight bomb plot |work=[[BBC News]] |date=October 30, 2010 |access-date=November 3, 2010}}</ref> The [[Federal Criminal Police Office (Germany)|Bundeskriminalamt]] received copies of the Dubai x-rays, and an investigator said German staff would not have identified the bomb either.<ref name="spiegel1">{{cite news |url=http://www.spiegel.de/international/world/0,1518,726746,00.html |title=Foiled Parcel Plot: World Scrambles to Tighten Air Cargo Security |work=[[Der Spiegel]] |access-date=November 2, 2010}}</ref><ref name="aljazeera1">{{cite web |url=http://english.aljazeera.net/news/middleeast/2010/10/20101031144429122829.html |title=Passenger jets carried Dubai bomb |publisher=[[Al Jazeera Media Network|Al Jazeera]] |date=October 31, 2010}}</ref> New airport security procedures followed in the U.S., largely to protect against PETN.<ref name="latimes.com"/>

==Medical use==
Like [[nitroglycerin]] (glyceryl trinitrate) and other [[nitrate (pharmacology)|nitrate]]s, PETN is also used medically as a [[vasodilator]] in the treatment of [[heart disease|heart conditions]].<ref name = newdrugs/><ref name=ebadi/> These drugs work by releasing the signaling gas [[nitric oxide]] in the body. The heart medicine ''Lentonitrat'' is nearly pure PETN.<ref>{{cite journal|title = The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate.|author = Russek H. I.| journal =American Journal of the Medical Sciences| volume = 252| issue = 1| pages = 9–20|year = 1966| pmid = 4957459|doi = 10.1097/00000441-196607000-00002|s2cid = 30975527}}</ref>

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 [[gas chromatography-mass spectrometry]].<ref>Baselt, R. (2008) ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA. pp. 1201–1203. {{ISBN|0962652369}}.</ref>

==See also==
* [[Erythritol tetranitrate]]
* [[RE factor]]

==References==
{{Reflist|30em}}

==Further reading==
{{Commons category|Pentaerythritol tetranitrate}}
* {{cite book|author = Cooper, Paul|title = Explosives Engineering|publisher = Wiley-VCH|location = Weinheim|year = 1997|isbn = 978-0-471-18636-6}}

{{Antianginals (nitrates)}}
{{Nitric oxide signaling}}

{{DEFAULTSORT:Pentaerythritol Tetranitrate}}
[[Category:Antianginals]]
[[Category:Explosive chemicals]]
[[Category:German inventions]]
[[Category:Nitrate esters]]