Centralite

Last updated
Centralite [1]
Centralite.svg
Names
Preferred IUPAC name
N,N′-Diethyl-N,N′-diphenylurea
Other names
Centralite 1
Carbamite
Ethyl centralite
N,N′-Diethylcarbanilide
Bis(N-ethyl-N-phenyl)urea
1,3-Diethyl-1,3-diphenylurea
sym-Diethyldiphenylurea
USAF EK-1047
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.496 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C17H20N2O/c1-3-18(15-11-7-5-8-12-15)17(20)19(4-2)16-13-9-6-10-14-16/h5-14H,3-4H2,1-2H3 X mark.svgN
    Key: PZIMIYVOZBTARW-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C17H20N2O/c1-3-18(15-11-7-5-8-12-15)17(20)19(4-2)16-13-9-6-10-14-16/h5-14H,3-4H2,1-2H3
    Key: PZIMIYVOZBTARW-UHFFFAOYAC
  • O=C(N(c1ccccc1)CC)N(c2ccccc2)CC
Properties
C17H20N2O
Molar mass 268.360 g·mol−1
AppearanceWhite to light grey crystalline powder
Density 0.8 g/cm3
Insoluble
Solubility in Acetone, ethanol and benzeneSoluble
-134.05·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethyl centralite is an organic compound. Its chemical name is 1,3-diethyl-1,3-diphenylurea. The molecular formula of ethyl centralite is C17H20N2O. This compound has important uses in industry and forensics. The structure of ethyl centralite includes two phenyl groups (aromatic rings) attached to a central urea group. There are also ethyl groups (–C₂H₅) bound to the nitrogen atoms of the urea. This structure gives ethyl centralite its special chemical properties. [2] Ethyl centralite is an important part of gunshot residue (GSR). When a gun is fired, the chemical reactions from the burning of the propellant leave behind tiny particles called gunshot residue. Ethyl centralite is one of the compounds found in GSR. It serves as an indicator in forensic investigations. Ethyl centralite helps determine if a firearm was recently fired. Ethyl centralite is widely used in various industries. Its main use is in the production of smokeless powder. In this use, it acts as a burning rate moderator and stabilizer. These functions are important for the controlled and consistent ignition of propellants. This is essential for the safety and effectiveness of ammunition. Ethyl centralite is also used as a plasticizer in the manufacturing of celluloid and enhances the flexibility and durability of the material. [2] [3]

Contents

History

In the 19th century chemists identified that nitrocellulose can destroy itself with the help of nitrogen oxides separating from it at storage, and tried to find bases which might capture those oxides. Urea has been used for stabilizing celluloid in the 19th century (and even in early American military powders), but like other water-soluble bases, it also attacks nitrocellulose, so German chemists substituted hydrogen atoms with nonpolar organic radicals to diminish this effect. [4]

Naming

The term "Centralite" was originally applied to dimethyldiphenylurea developed about 1906 at the German private military-industrial laboratory Zentralstelle für wissenschaftlich-technische Untersuchungen  [ de ] (Center for Scientific-Technical Research) in Neubabelsberg as a deterrent coating for smokeless powder in military rifle cartridges. Thereafter, all hydrocarbon-substituted symmetrical diphenyl urea compounds used as smokeless powder deterrents (or moderants) were called centralites after the laboratory. The preferred ethyl centralite became known as Centralite No. 1 and the original methyl centralite was identified as Centralite No. 2. Butyl centralite was also used as a celluloid plasticizer. [5] [6]

Comparison with analogs

Compared to diphenylurea, it has a far more convoluted reaction history. Finally, nitrated anilines are produced. Centralite-2, also known as sym-dimethyldiphenylurea, is a methyl analog that is moderately utilized overseas. Though they are likewise excellent plasticizers, centralites are thought to be a little less effective stabilizer than 2-nitrodiphenylamine. To benefit from their plasticizing qualities, they are commonly employed in propellants at higher fractions than diphenylamines.

Synthesis

Ethyl centralite is also known as 1,3-diethyl-1,3-diphenylurea. It is synthesized through a chemical reaction. This reaction involves the condensation of aniline (C₆H₅NH₂) with ethyl isocyanate (C₂H₅NCO). The reaction typically occurs under controlled conditions. In this reaction, aniline reacts with ethyl isocyanate. This forms ethyl centralite through the formation of urea linkages.

The general reaction can be represented as follows:

2 C6H5NH2 + 2 C2H5NCO → C6H5NHCONHC6H5(C2H5)2 + 2 CO2

In this reaction, aniline (C6H5NH2) serves as the aromatic amine and ethyl isocyanate (C2H5NCO) is the isocyanate compound that reacts with the amine groups.

The reaction produces ethyl centralite. It also produces carbon dioxide (CO₂) as a byproduct. The process is usually done in a solvent, such as an alcohol. The solvent helps dissolve the reactants. It also helps control the reaction temperature. After the reaction is finished, the ethyl centralite is purified. This is done through recrystallization or other purification methods. The goal is to obtain a pure product. [7] [8]

Applications

Smokeless powder

Forensic science

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">Gunpowder</span> Explosive once used in firearms

Gunpowder, also commonly known as black powder to distinguish it from modern smokeless powder, is the earliest known chemical explosive. It consists of a mixture of sulfur, charcoal, and potassium nitrate (saltpeter). The sulfur and charcoal act as fuels while the saltpeter is an oxidizer. Gunpowder has been widely used as a propellant in firearms, artillery, rocketry, and pyrotechnics, including use as a blasting agent for explosives in quarrying, mining, building pipelines, tunnels, and roads.

<span class="mw-page-title-main">Cordite</span> Smokeless propellant, used to replace gunpowder

Cordite is a family of smokeless propellants developed and produced in Britain since 1889 to replace black powder as a military firearm propellant. Like modern gunpowder, cordite is classified as a low explosive because of its slow burning rates and consequently low brisance. These produce a subsonic deflagration wave rather than the supersonic detonation wave produced by brisants, or high explosives. The hot gases produced by burning gunpowder or cordite generate sufficient pressure to propel a bullet or shell to its target, but not so quickly as to routinely destroy the barrel of the gun.

A propellant is a mass that is expelled or expanded in such a way as to create a thrust or another motive force in accordance with Newton's third law of motion, and "propel" a vehicle, projectile, or fluid payload. In vehicles, the engine that expels the propellant is called a reaction engine. Although technically a propellant is the reaction mass used to create thrust, the term "propellant" is often used to describe a substance which contains both the reaction mass and the fuel that holds the energy used to accelerate the reaction mass. For example, the term "propellant" is often used in chemical rocket design to describe a combined fuel/propellant, although the propellants should not be confused with the fuel that is used by an engine to produce the energy that expels the propellant. Even though the byproducts of substances used as fuel are also often used as a reaction mass to create the thrust, such as with a chemical rocket engine, propellant and fuel are two distinct concepts.

<span class="mw-page-title-main">Solid fuel</span> Solid material that can be burnt to release energy

Solid fuel refers to various forms of solid material that can be burnt to release energy, providing heat and light through the process of combustion. Solid fuels can be contrasted with liquid fuels and gaseous fuels. Common examples of solid fuels include wood, charcoal, peat, coal, hexamine fuel tablets, dry dung, wood pellets, corn, wheat, rice, rye, and other grains. Solid fuels are extensively used in rocketry as solid propellants. Solid fuels have been used throughout human history to create fire and solid fuel is still in widespread use throughout the world in the present day.

<span class="mw-page-title-main">Carbamate</span> Chemical group (>N–C(=O)–O–)

In organic chemistry, a carbamate is a category of organic compounds with the general formula R2NC(O)OR and structure >N−C(=O)−O−, which are formally derived from carbamic acid. The term includes organic compounds, formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion H2NCOO.

Internal ballistics, a subfield of ballistics, is the study of the propulsion of a projectile.

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

Smokeless powder is a type of propellant used in firearms and artillery that produces less smoke and less fouling when fired compared to black powder. Because of their similar use, both the original black powder formulation and the smokeless propellant which replaced it are commonly described as gunpowder. The combustion products of smokeless powder 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.

Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to groups or a class of compounds with the same ring structure as the parent compound. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.

<span class="mw-page-title-main">Gunshot residue</span> Particles expelled from the muzzle of a gun

Gunshot residue (GSR), also known as cartridge discharge residue (CDR), gunfire residue (GFR), or firearm discharge residue (FDR), consists of all of the particles that are expelled from the muzzle of a gun following the discharge of a bullet. It is principally composed of burnt and unburnt particles from the explosive primer, the propellant (gunpowder), stabilisers and other additives. The act of firing a bullet incites a highly pressurised, explosive reaction that is contained within the barrel of the firearm, which expels the bullet. This can cause the bullet, the barrel, or the cartridge to become damaged, meaning gunshot residue may also include metallic particles from the cartridge casing, the bullet jacket, as well as any other dirt or residue contained within the barrel that could have become dislodged.

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

Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.

<span class="mw-page-title-main">Contact shot</span> Type of gunshot wound

A contact shot is a gunshot wound incurred while the muzzle of the firearm is in direct contact with the body at the moment of discharge. Contact shots are often the result of close-range gunfights, suicide, or execution.

Brown powder or prismatic powder, sometimes referred as "cocoa powder" due to its color, was a propellant used in large artillery and ship's guns from the 1870s to the 1890s. While similar to black powder, it was chemically formulated and formed hydraulically into a specific grain shape to provide slower burn rates with neutral or progressive burning, as opposed to the faster and regressive burn typical of randomly shaped grains of black powder produced by crushing and screening powder formed into sheets in a press box, as was typical for cannon powder previously.

A pyrotechnic composition is a substance or mixture of substances designed to produce an effect by heat, light, sound, gas/smoke or a combination of these, as a result of non-detonative self-sustaining exothermic chemical reactions. Pyrotechnic substances do not rely on oxygen from external sources to sustain the reaction.

<span class="mw-page-title-main">Black powder substitute</span> Substitute for black powder

A black powder substitute is a replacement for black powder (gunpowder), primarily used in muzzleloading firearms. Substitutes may have slightly different properties from gunpowder such as: reduced sensitivity as an explosive, increased efficiency as a propellant powder, different density, and/or reduced ignition efficiency. This also means that substitutes are subject to different restrictions than gunpowder.

The following are terms related to firearms and ammunition topics.

<span class="mw-page-title-main">1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide</span> Chemical compound

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide is a water-soluble carbodiimide usually handled as the hydrochloride.

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

Firearm propellants are a specialized type of propellant used to discharge a projectile through the barrel of a firearm. Mixtures of different chemical substances are often used to control the rate of gas release, or prevent decomposition of the propellant prior to use. Short-barrel firearms such as handguns necessitate faster-burning propellants to obtain sufficient muzzle energy, while long guns typically use slower-burning propellants. The pressure relationships between propellant chemical reactions and bullet response are described as internal ballistics.

<span class="mw-page-title-main">Primer (firearms)</span> Component of the firearm cartridge for initiating propellant combustion

In firearms and artillery, the primer is the chemical and/or device responsible for initiating the propellant combustion that will propel the projectiles out of the gun barrel.

<span class="mw-page-title-main">Ball propellant</span> Form of nitrocellulose used in small arms cartridges

Ball propellant is a form of nitrocellulose used in small arms cartridges. Ball propellant can be manufactured more rapidly with greater safety and less expense than extruded propellants.

References

  1. CID 6828 from PubChem
  2. 1 2 "Ethyl centralite / Centralite I, CAS: 85-98-3 - Synthesia". organics.synthesia.eu. Retrieved 2023-11-02.
  3. "Typical Product Specifications & Properties - Ethyl Centralite" (PDF).
  4. "Explosives". Philadelphia, P. Blakiston. 1917.
  5. Davis, Tenney L. (1943). The Chemistry of Powder & Explosives (Angriff Press [1992] ed.). John Wiley & Sons Inc. pp. 317–320. ISBN   0-913022-00-4.
  6. Davis, William C. Jr. (1981). Handloading . National Rifle Association of America. p.  130. ISBN   0-935998-34-9.
  7. "The Preparation Method of Centralite-II".
  8. "Syntheses and Characterisations of Derivatives of Ethyl Centralite".
  9. "SHOOTERS WORLD RELOADING GUIDE" (PDF).
  10. 1 2 3 "Exploring the Versatile Applications and Synthesis of 1,3-Dimethyl-1,3-diphenylurea in Modern Chemistry".
  11. "A stabilizer of explosives: Centralite ll".