Editing Pentaerythritol tetranitrate (section)

==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>