Xylitol pentanitrate (XPN) is a nitrated ester

primary explosive An explosive (or explosive material) 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 ...

first synthesized in 1891 by Gabriel Bertrand. Law enforcement has taken an interest in XPN along with

erythritol tetranitrate Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact. Like many nitrate esters, ETN acts as a vasodilator, and was the active ingredient in th ...

(ETN) and

pentaerythritol tetranitrate Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, (ПЕНТА, primarily in Russian) TEN, corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an explosive material. It is the nitrate ester of pentaerythr ...

(PETN) due to their ease of synthesis, which makes them accessible to amateur chemists and

terrorists Terrorism, in its broadest sense, is the use of criminal violence to provoke a state of terror or fear, mostly with the intention to achieve political or religious aims. The term is used in this regard primarily to refer to intentional violen ...

.{{Cite journal, last1=Dong, first1=Jun, last2=Yan, first2=Qi-Long, last3=Liu, first3=Pei-Jin, last4=He, first4=Wei, last5=Qi, first5=Xiao-Fei, last6=Zeman, first6=Svatopluk, date=2018, title=The correlations among detonation velocity, heat of combustion, thermal stability and decomposition kinetics of nitric esters, url=http://link.springer.com/10.1007/s10973-017-6706-5, journal=Journal of Thermal Analysis and Calorimetry, language=en, volume=131, issue=2, pages=1391–1403, doi=10.1007/s10973-017-6706-5, s2cid=102678177 , issn=1388-6150

Properties

At room temperature XPN exists as a white crystalline solid. When heated to 163 °C, liquid xylitol pentanitrate begins to crackle and produce a dark vapour. When decomposed, every gram of XPN produces 200 mL of gas, which makes it a high performance explosive. Rotter impact analysis of XPN found a figure of insensitiveness of 25 ( RDX = 80). XPN displayed a similar sensitivity to electric static discharge to ETN and PETN.

Synthesis

Xylitol pentanitrate is formed by reaction of xylitol pentaacetate with fuming

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available ni ...

and glacial

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...

Complete oxidation

Much like ETN, XPN has a positive oxygen balance, which means the

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ...

and

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements ...

in the molecule can be fully oxidized without another

oxidizing agent An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxi ...

being added. 4C5H7N5O15 -> Delta20CO2 + 14H2O + 10N2 + 3O2 The decomposition of four molecules of XPN releases three O₂. The free oxygen molecules can be used to oxidize an added metal dust or negative oxygen balanced explosive like TNT.

Properties

Synthesis

Complete oxidation

See also

References