Xylitol pentanitrate

Last updated
Xylitol pentanitrate
Xylitol pentanitrate.png
Names
IUPAC name
1,2,3,4,5-Pentakis-nitrooxy-pentane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C5H7N5O15/c11-6(12)21-1-3(23-8(15)16)5(25-10(19)20)4(24-9(17)18)2-22-7(13)14/h3-5H,1-2H2/t3-,4+,5+ X mark.svgN
    Key: STNMPEICBMBFAP-SCDXWVJYSA-N X mark.svgN
  • InChI=1/C5H7N5O15/c11-6(12)21-1-3(23-8(15)16)5(25-10(19)20)4(24-9(17)18)2-22-7(13)14/h3-5H,1-2H2/t3-,4+,5+
    Key: STNMPEICBMBFAP-SCDXWVJYBV
  • C([C@H]([C@@H]([C@H](CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
Properties
C5H7N5O15
Molar mass 377.131 g·mol−1
Density 1.852 g/cm3
Melting point 45.5 °C (114 °F; 318 K)
Boiling point 163-185 °C (346 - 358 °F; 436 - 458 K) (Decomposes)
Solubility Soluble in ethanol, toluene, chloroform, acetone [1]
log P 3.42 [2]
Structure
Monoclinic [3]
Explosive data
Shock sensitivity 4.5 J [3]
Friction sensitivity 18 N [3]
Detonation velocity 7,100 m/s
Hazards
GHS labelling:
GHS-pictogram-explos.svg GHS-pictogram-rondflam.svg
167 °C (333 °F; 440 K) [3]
Lethal dose or concentration (LD, LC):
148 (μM in splenocytes) [2]
Related compounds
Related compounds
Xylitol
Erythritol tetranitrate
Pentaerythritol tetranitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN (what is  Yes check.svgYX mark.svgN ?)

Xylitol pentanitrate (XPN) is a nitrated ester primary explosive [3] [4] first synthesized in 1891 by Gabriel Bertrand. [5] Law enforcement has taken an interest in XPN along with erythritol tetranitrate (ETN) and pentaerythritol tetranitrate (PETN) due to their ease of synthesis, which makes them accessible to amateur chemists and terrorists. [6] [7]

Contents

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. [3]

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. [3]

Synthesis

Xylitol pentanitrate is formed by reaction of xylitol pentaacetate with fuming nitric acid and glacial acetic acid. [5]

Complete oxidation

Much like ETN, XPN has a positive oxygen balance, which means the carbon and hydrogen in the molecule can be fully oxidized without another oxidizing agent being added.

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.

See also


Related Research Articles

<span class="mw-page-title-main">Explosive</span> Substance that can explode

An explosive 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 explosive charge is a measured quantity of explosive material, which may either be composed solely of one ingredient or be a mixture containing at least two substances.

<span class="mw-page-title-main">Nitrogen</span> Chemical element, symbol N and atomic number 7

Nitrogen is a chemical element; it has symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element bond to form N2, a colorless and odorless diatomic gas. N2 forms about 78% of Earth's atmosphere, making it the most abundant uncombined element in air. Because of the volatility of nitrogen compounds, nitrogen is relatively rare in the solid parts of the Earth.

<span class="mw-page-title-main">Nitroglycerin</span> Chemical compound

Nitroglycerin (NG), also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Discovered in 1847 by Ascanio Sobrero, nitroglycerin has been used as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. It is combined with nitrocellulose to form double-based smokeless powder, which has been used as a propellant in artillery and firearms since the 1880s.

<span class="mw-page-title-main">Nitric acid</span> Highly corrosive mineral acid

Nitric acid is the inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%.

<span class="mw-page-title-main">Pentaerythritol tetranitrate</span> Explosive chemical compound

Pentaerythritol tetranitrate (PETN), also known as PENT, pentyl, PENTA, TEN, corpent, or penthrite, is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66. When mixed with a plasticizer, PETN forms a plastic explosive. Along with RDX it is the main ingredient of Semtex and C4.

<span class="mw-page-title-main">Dinitrogen pentoxide</span> Chemical compound

Dinitrogen pentoxide is the chemical compound with the formula N2O5. It is one of the binary nitrogen oxides, a family of compounds that only contain nitrogen and oxygen. It exists as colourless crystals that sublime slightly above room temperature, yielding a colorless gas.

<span class="mw-page-title-main">Smokeless powder</span> Type of propellant

Smokeless powder, also referred to as gunpowder, is a type of propellant used in firearms and artillery that produces less smoke and less fouling when fired compared to black powder. The combustion products are mainly gaseous, compared to around 55% solid products for black powder. In addition, smokeless powder does not leave the thick, heavy fouling of hygroscopic material associated with black powder that causes rusting of the barrel.

<span class="mw-page-title-main">Mannitol hexanitrate</span> Chemical compound

Mannitol hexanitrate is a powerful explosive. Physically, it is a powdery solid at normal temperature ranges, with density of 1.73 g/cm3. The chemical name is hexanitromannitol and it is also known as nitromannite, MHN, and nitromannitol, and by the trademarks Nitranitol and Mannitrin. It is more stable than nitroglycerin, and it is used in detonators.

<span class="mw-page-title-main">Hydroxylammonium nitrate</span> Chemical compound

Hydroxylammonium nitrate or hydroxylamine nitrate (HAN) is an inorganic compound with the chemical formula [NH3OH]+[NO3]. It is a salt derived from hydroxylamine and nitric acid. In its pure form, it is a colourless hygroscopic solid. It has potential to be used as a rocket propellant either as a solution in monopropellants or bipropellants. Hydroxylammonium nitrate (HAN)-based propellants are a viable and effective solution for future green propellant-based missions, as it offers 50% higher performance for a given propellant tank compared to commercially used hydrazine.

<span class="mw-page-title-main">Ethylene glycol dinitrate</span> Chemical compound

Ethylene glycol dinitrate, abbreviated EGDN and NGC, also known as Nitroglycol, is a colorless, oily, explosive liquid obtained by nitrating ethylene glycol. It is similar to nitroglycerine in both manufacture and properties, though it is more volatile and less viscous. Unlike nitroglycerine, the chemical has a perfect oxygen balance, meaning that its ideal exothermic decomposition would completely convert it to low energy carbon dioxide, water, and nitrogen gas, with no excess unreacted substances, without needing to react with anything else.

<span class="mw-page-title-main">1,3,5-Triazido-2,4,6-trinitrobenzene</span> Chemical compound

1,3,5-Triazido-2,4,6-trinitrobenzene, also known as TATNB (triazidotrinitrobenzene) and TNTAZB (trinitrotriazidobenzene), is an aromatic high explosive composed of a benzene ring with three azido groups (-N3) and three nitro groups (-NO2) alternating around the ring, giving the chemical formula C6(N3)3(NO2)3. Its detonation velocity is 7,350 meters per second, which is comparable to TATB (triaminotrinitrobenzene).

The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most common oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also forms a part of nitric acid and nitrate salts. Nitrogen compounds also have an important role in organic chemistry, as nitrogen is part of proteins, amino acids and adenosine triphosphate.

Oxygen balance is an expression that is used to indicate the degree to which an explosive can be oxidized, to determine if an explosive molecule contains enough oxygen to fully oxidize the other atoms in the explosive. For example, fully oxidized carbon forms carbon dioxide, hydrogen forms water, sulfur forms sulfur dioxide, and metals form metal oxides. A molecule is said to have a positive oxygen balance if it contains more oxygen than is needed and a negative oxygen balance if it contains less oxygen than is needed.

Polyvinyl nitrate (abbreviated: PVN) is a high-energy polymer with the idealized formula of [CH2CH(ONO2)]. Polyvinyl nitrate is a long carbon chain (polymer) with nitrate groups bonded randomly along the chain. PVN is a white, fibrous solid, and is soluble in polar organic solvents such as acetone. PVN can be prepared by nitrating polyvinyl alcohol with an excess of nitric acid. Because PVN is also a nitrate ester such as nitroglycerin (a common explosive), it exhibits energetic properties and is commonly used in explosives and propellants.

<span class="mw-page-title-main">Diethylene glycol dinitrate</span> Chemical compound

Diethylene glycol dinitrate (DEGDN) is an explosive nitrated alcohol ester with the formula C4H8N2O7. While chemically similar to numerous other high explosives, pure diethylene glycol dinitrate is difficult to ignite or detonate. Ignition typically requires localized heating to the decomposition point unless the DEGDN is first atomized.

<span class="mw-page-title-main">Erythritol tetranitrate</span> Chemical compound

Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact.

<span class="mw-page-title-main">Hexanitroethane</span> Chemical compound

Hexanitroethane (HNE) is an organic compound with chemical formula C2N6O12 or (O2N)3C-C(NO2)3. It is a solid matter with a melting point of 135 °C.

<span class="mw-page-title-main">Tetranitratoxycarbon</span> Chemical compound

Tetranitratoxycarbon, systematic name tetra(nitrato-O,O,O-methyl)methane, is a hypothetical molecule that was proposed by Clara Lazen, a fifth-grader in Kansas City, Missouri, who conceived of its structure and built a model in 2012. She is credited as co-author of a scientific paper on the molecule, which uses computational chemistry to predict that the molecule could actually exist.

<span class="mw-page-title-main">Nitrate ester</span> Chemical group (–ONO2)

In organic chemistry, a nitrate ester is an organic functional group with the formula R−ONO2, where R stands for any organyl group. They are the esters of nitric acid and alcohols. A well-known example is nitroglycerin, which is not a nitro compound, despite its name.

<span class="mw-page-title-main">Dinitroglycoluril</span> Chemical compound

Dinitroglycoluril (DNGU) is a high explosive chemical compound with the formula C4H4N6O6. Dinitroglycoluril is of growing interest due to its stability, ability to mix with oxygen positive explosives to form composites, and it is a precursor to tetranitroglycoluril.

References

  1. Stark, Kelly-Anne S.; Gascooke, Jason R.; Gibson, Christopher T.; Lenehan, Claire E.; Bonnar, Callum; Fitzgerald, Mark; Kirkbride, K. Paul (November 2020). "Xylitol pentanitrate – Its characterization and analysis". Forensic Science International. 316: 110472. doi:10.1016/j.forsciint.2020.110472. PMID   32919164. S2CID   221643415.
  2. 1 2 Šarlauskas, Jonas; KrikŠtopaitis, Kastis; MiliukienĖ, Valė; ČĖnas, Narimantas; AnuseviČius, Žilvinas; ŠaikŪnas, Algirdas (2011). "Investigation on the Electrochemistry and Cytotoxicity of Organic Nitrates and Nitroamines". Central European Journal of Energetic Materials. 8: 15–24.
  3. 1 2 3 4 5 6 7 Stark, Kelly-Anne S.; Alvino, Jason F.; Kirkbride, K. Paul; Sumby, Christopher J.; Metha, Gregory F.; Lenehan, Claire E.; Fitzgerald, Mark; Wall, Craig; Mitchell, Mark; Prior, Chad (2019). "Crystal Structure, Sensitiveness and Theoretical Explosive Performance of Xylitol Pentanitrate (XPN)". Propellants, Explosives, Pyrotechnics. 44 (5): 541–549. doi:10.1002/prep.201800337. ISSN   0721-3115. S2CID   109872121.
  4. Klapötke, Thomas M. (2021-01-18). "X". O-Z. De Gruyter. pp. 2027–2030. doi:10.1515/9783110672558-019. ISBN   978-3-11-067255-8.
  5. 1 2 Wright, I. G.; Hayward, L. D. (1960). "The Pentitol Pentanitrates". Canadian Journal of Chemistry. 38 (2): 316–319. doi:10.1139/v60-045. ISSN   0008-4042.
  6. Yan, Qi-Long; Künzel, Martin; Zeman, Svatopluk; Svoboda, Roman; Bartošková, Monika (2013). "The effect of molecular structure on thermal stability, decomposition kinetics and reaction models of nitric esters". Thermochimica Acta. 566: 137–148. doi:10.1016/j.tca.2013.05.032.
  7. Dong, Jun; Yan, Qi-Long; Liu, Pei-Jin; He, Wei; Qi, Xiao-Fei; Zeman, Svatopluk (2018). "The correlations among detonation velocity, heat of combustion, thermal stability and decomposition kinetics of nitric esters". Journal of Thermal Analysis and Calorimetry. 131 (2): 1391–1403. doi:10.1007/s10973-017-6706-5. ISSN   1388-6150. S2CID   102678177.