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 Gabriel Bertrand (born 17 May 1867 in Paris, died 20 June 1962 in Paris) was a French pharmacologist, biochemist and bacteriologist. Bertrand introduced into biochemistry both the term “ oxidase” and the concept of trace elements. The lacc ...

. 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 ...

(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 RDX (abbreviation of "Research Department eXplosive") or hexogen, among other names, is an organic compound with the formula (O2N2CH2)3. It is a white solid without smell or taste, widely used as an explosive. Chemically, it is classified as a ...

= 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 nitri ...

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 component ...

Complete oxidation

Much like ETN, XPN has a positive

oxygen balance Oxygen balance (OB, OB%, or Ω) is an expression that is used to indicate the degree to which an explosive can be oxidized. If an explosive molecule contains just enough oxygen to fully oxidize the other atoms in the explosive. For example, fully ...

, which means the

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

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 as wel ...

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 "Electron acceptor, accepts"/"receives" an electron from a (called the , , or ). In ot ...

being added. 4C5H7N5O15 ->

Delta Delta commonly refers to: * Delta (letter) (Δ or δ), a letter of the Greek alphabet * River delta, at a river mouth * D ( NATO phonetic alphabet: "Delta") * Delta Air Lines, US * Delta variant of SARS-CoV-2 that causes COVID-19 Delta may also ...

20CO2 + 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 Trinitrotoluene (), more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagen ...

Properties

Synthesis

Complete oxidation

See also

References