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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Centralite (empirical formula: C17H20N2O) is a gunshot residue also known as ethyl centralite. Its IUPAC name is 1,3-diethyl-1,3-diphenylurea. Ethyl centralite is insoluble in water, but is soluble in acetone, ethanol and benzene. It is mainly used as a burning rate moderator and stabilizer for smokeless powder, and also a plasticizer for celluloid. [2]

Contents

History

In the 19th century chemists identified that nitrocellulose can destroy itself by action 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. [3]

Naming

The term "Centralite" was originally applied to dimethyldiphenylurea developed about 1906 at the German Central War Laboratory Zentralstelle für wissenschaftlich-technische Untersuchungen 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. [4] [5]

Comparison with analogs

Its reaction history is considerably more complicated than that of diphenylurea. Ending up with nitrated anilines, the methyl analog centralite-2 or sym-dimethyldiphenylurea is also known and is used somewhat abroad. The centralite are considered to be somewhat less effective as stabilizers than 2-nitrodiphenylamine, but they are also quite good plasticizers. When found in propellants they are frequently used at higher fractions than the diphenylamines to take advantage of their plasticizing properties.

Related Research Articles

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<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.

<span class="mw-page-title-main">Nitrocellulose</span> Highly flammable compound

Nitrocellulose is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and sulfuric acid. One of its first major uses was as guncotton, a replacement for gunpowder as propellant in firearms. It was also used to replace gunpowder as a low-order explosive in mining and other applications. In the form of collodion it was also a critical component in an early photographic emulsion, the use of which revolutionized photography in the 1860s.

<span class="mw-page-title-main">Thymine</span> Chemical compound of DNA

Thymine is one of the four nucleobases in the nucleic acid of DNA that are represented by the letters G–C–A–T. The others are adenine, guanine, and cytosine. Thymine is also known as 5-methyluracil, a pyrimidine nucleobase. In RNA, thymine is replaced by the nucleobase uracil. Thymine was first isolated in 1893 by Albrecht Kossel and Albert Neumann from calf thymus glands, hence its name.

Celluloids are a class of materials produced by mixing nitrocellulose and camphor, often with added dyes and other agents. Once much more common for its use as photographic film before the advent of safer methods, celluloid's common present-day uses are for manufacturing table tennis balls, musical instruments, combs, office equipment, fountain pen bodies, and guitar picks.

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

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">Hydrogen peroxide - urea</span> Chemical compound

Hydrogen peroxide - urea is a white crystalline solid chemical compound composed of equal amounts of hydrogen peroxide and urea. It contains solid and water-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an oxidizing agent. Often called carbamide peroxide in dentistry, it is used as a source of hydrogen peroxide when dissolved in water for bleaching, disinfection and oxidation.

<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.

Ballistite is a smokeless propellant made from two high explosives, nitrocellulose and nitroglycerine. It was developed and patented by Alfred Nobel in the late 19th century.

Poudre B was the first practical smokeless gunpowder created in 1884. It was perfected between 1882 and 1884 at "Laboratoire Central des Poudres et Salpêtres" in Paris, France. Originally called "Poudre V" from the name of the inventor, Paul Vieille, it was arbitrarily renamed "Poudre B" to distract German espionage. "Poudre B" is made from 68.2% insoluble nitrocellulose, 29.8% soluble nitrocellulose gelatinized with ether and 2% paraffin. "Poudre B" is made up of very small paper-thin flakes that are not white but dark greenish grey in colour. "Poudre B" was first used to load the 8mm Lebel cartridges issued in 1886 for the Lebel rifle.

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">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

<span class="mw-page-title-main">Xanthate</span> Salt that is a metal-thioate/O-esters of dithiocarbonate

A xanthate is a salt or ester of a xanthic acid. The formula of the salt of xanthic acid is [R−O−CS2]M+. Xanthate also refers to the anion [R−O−CS2]. The formula of a xanthic acid is R−O−C(=S)−S−H, such as ethyl xanthic acid, while the formula of an ester of a xanthic acid is R−O−C(=S)−S−R', where R and R' are organyl groups. The salts of xanthates are also called O-organyl dithioates. The esters of xanthic acid are also called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek ξανθός (xanthos) meaning 'yellowish' or 'golden', and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain sulphide bearing ores. They are also versatile intermediates in organic synthesis.

<span class="mw-page-title-main">Methyl isobutyl ketone</span> Chemical compound

Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the condensed chemical formula (CH3)2CHCH2C(O)CH3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

<span class="mw-page-title-main">2-Nitrodiphenylamine</span> Chemical compound

2-Nitrodiphenylamine is an organic chemical with the formula C6H5NHC6H4NO2. It is a nitrated derivative of diphenylamine. It is a red solid, usually found in form of flakes or powder. It is polar but hydrophobic.

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">Ethylene carbonate</span> Chemical compound

Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the cyclic carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a transparent crystalline solid, practically odorless and colorless, and somewhat soluble in water. In the liquid state (m.p. 34-37 °C) it is a colorless odorless liquid.

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

Oxamide is the organic compound with the formula (CONH2)2. This white crystalline solid is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. Oxamide is the diamide derived from oxalic acid, and the hydrate of cyanogen.

<span class="mw-page-title-main">Hodgdon Powder Company</span>

The Hodgdon Powder Company began in 1952 as B.E. Hodgdon, Inc., and has become a major distributor of smokeless powder for the ammunition industry, as well as for individuals who load their own ammunition by hand. The company's corporate office and manufacturing facilities are located in Kansas, United States. Hodgdon acquired IMR Powder Company in 2003. Winchester branded reloading powders have been distributed in the United States by Hodgdon since March 2006.

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. "Ethyl centralite / Centralite I, CAS: 85-98-3 - Synthesia". organics.synthesia.eu. Retrieved 2023-11-02.
  3. https://archive.org/details/explosives02mars/page/641/mode/1up
  4. 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.
  5. Davis, William C. Jr. (1981). Handloading . National Rifle Association of America. p.  130. ISBN   0-935998-34-9.