![]() | |
Names | |
---|---|
IUPAC name 1,2,3,4,5-Pentakis-nitrooxy-pentane | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
| |
| |
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: | |
![]() ![]() | |
167 °C (333 °F; 440 K) [3] | |
Lethal dose or concentration (LD, LC): | |
LC50 (median concentration) | 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). |
Xylitol pentanitrate (XPN) is a nitrated ester primary explosive [3] [4] first synthesized in 1891 by Gabriel Bertrand. [5] [6] 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. [7] [8]
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, a 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 static discharge to ETN and PETN. [3]
Xylitol pentanitrate is formed by nitration of xylitol pentaacetate. Nowadays, fuming nitric acid and glacial acetic acid is often used, [9] but Bertrand originally employed a cheaper nitrating agent, the mixture of nitric and sulfuric acids (he called it mélange nitrosulfurique, the common English name is "mixed acid"). [6]
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 such as TNT.
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.
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 colourless and odourless diatomic gas. N2 forms about 78% of Earth's atmosphere, making it the most abundant chemical species in air. Because of the volatility of nitrogen compounds, nitrogen is relatively rare in the solid parts of the Earth.
Nitrate is a polyatomic ion with the chemical formula NO−
3. Salts containing this ion are called nitrates. Nitrates are common components of fertilizers and explosives. Almost all inorganic nitrates are soluble in water. An example of an insoluble nitrate is bismuth oxynitrate.
Nitroglycerin (NG), also known as trinitroglycerol (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless or pale yellow, 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 a nitrate ester rather than a nitro compound, but the traditional name is retained. Discovered in 1846 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, used as a propellant in artillery and firearms since the 1880s.
Nitric acid is an 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%.
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.
Nitrogen dioxide is a chemical compound with the formula NO2. One of several nitrogen oxides, nitrogen dioxide is a reddish-brown gas. It is a paramagnetic, bent molecule with C2v point group symmetry. Industrially, NO2 is an intermediate in the synthesis of nitric acid, millions of tons of which are produced each year, primarily for the production of fertilizers.
Dinitrogen pentoxide is the chemical compound with the formula N2O5. It is one of the binary nitrogen oxides, a family of compounds that contain only nitrogen and oxygen. It exists as colourless crystals that sublime slightly above room temperature, yielding a colorless gas.
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.
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.
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.
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.
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.
Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact.
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.
Ammonium dinitramide (ADN) is an inorganic compound with the chemical formula [NH4][N(NO2)2]. It is the ammonium salt of dinitraminic acid HN(NO2)2. It consists of ammonium cations [NH4]+ and dinitramide anions −N(NO2)2. ADN decomposes under heat to leave only nitrogen, oxygen, and water.
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.
Cerium nitrate refers to a family of nitrates of cerium in the +3 or +4 oxidation state. Often these compounds contain water, hydroxide, or hydronium ions in addition to cerium and nitrate. Double nitrates of cerium also exist.
Thorium(IV) nitrate is a chemical compound, a salt of thorium and nitric acid with the formula Th(NO3)4. A white solid in its anhydrous form, it can form tetra- and pentahydrates. As a salt of thorium it is weakly radioactive.
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.