Carbohydrazide

Last updated
Carbohydrazide
Carbohydrazide.png
OC(N2H3)2.png
Names
IUPAC name
1,3-Diaminourea
Other names
Carbohydrazine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.126 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-837-2
PubChem CID
UNII
  • InChI=1S/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6) Yes check.svgY
    Key: XEVRDFDBXJMZFG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6)
    Key: XEVRDFDBXJMZFG-UHFFFAOYAS
  • O=C(NN)NN
Properties
CH6N4O
Molar mass 90.09 g/mol
Density 1.341 g/cm3
Melting point 153–154 °C (307–309 °F; 426–427 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Carbohydrazide is the chemical compound with the formula OC(N2H3)2. It appears as a white solid that is soluble in water, [1] [2] but not in many organic solvents, such as ethanol, ether or benzene. It decomposes upon melting. [2] A number of carbazides are known where one or more N-H groups are replaced by other substituents. They occur widely in the drugs, herbicides, plant growth regulators, and dyestuffs.

Contents

Production

Industrially the compound is produced by treatment of urea with hydrazine: [3]

OC(NH2)2 + 2 N2H4 → OC(N2H3)2 + 2 NH3

It can also be prepared by reactions of other C1-precursors with hydrazine, such as carbonate esters. [2] It can be prepared from phosgene, but this route cogenerates the hydrazinium salt [N2H5]Cl and results in some diformylation. Carbazic acid is also a suitable precursor:

N2NH3CO2H + N2H4 → OC(N2H3)2 + H2O

Structure

The molecule is nonplanar. All nitrogen centers are at least somewhat pyramidal, indicative of weaker C-N pi-bonding. The C-N and C-O distances are about 1.36 and 1.25 Å, respectively. [4]

Industrial uses

Hazards

Heating carbohydrazide may result in an explosion. Carbohydrazide is harmful if swallowed, irritating to eyes, respiratory system, and skin. Carbohydrazide is toxic to aquatic organisms. [10]

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">Ammonium perchlorate</span> Chemical compound

Ammonium perchlorate ("AP") is an inorganic compound with the formula NH4ClO4. It is a colorless or white solid that is soluble in water. It is a powerful oxidizer. Combined with a fuel, it can be used as a rocket propellant called ammonium perchlorate composite propellant. Its instability has involved it in a number of accidents, such as the PEPCON disaster.

<span class="mw-page-title-main">Hydrazine</span> Colorless flammable liquid with an ammonia-like odor

Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydrazine hydrate.

Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula CH
3
NO
2
. It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent. As an intermediate in organic synthesis, it is used widely in the manufacture of pesticides, explosives, fibers, and coatings. Nitromethane is used as a fuel additive in various motorsports and hobbies, e.g. Top Fuel drag racing and miniature internal combustion engines in radio control, control line and free flight model aircraft.

In chemistry, azide is a linear, polyatomic anion with the formula N−3 and structure N=N+=N. It is the conjugate base of hydrazoic acid HN3. Organic azides are organic compounds with the formula RN3, containing the azide functional group. The dominant application of azides is as a propellant in air bags.

<span class="mw-page-title-main">Hydrazoic acid</span> Unstable and toxic chemical compound

Hydrazoic acid, also known as hydrogen azide, azic acid or azoimide, is a compound with the chemical formula HN3. It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. The oxidation state of the nitrogen atoms in hydrazoic acid is fractional and is -1/3. It was first isolated in 1890 by Theodor Curtius. The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes.

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

Lithium perchlorate is the inorganic compound with the formula LiClO4. This white or colourless crystalline salt is noteworthy for its high solubility in many solvents. It exists both in anhydrous form and as a trihydrate.

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

Pentanitroaniline, sometimes called hexyl, is an explosive organic compound. It is a relatively sensitive explosive that can be used as a base charge for detonators, although it is uncommon in this application.

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

Azines are a functional class of organic compounds with the connectivity RR'C=N-N=CRR'. These compounds are the product of the condensation of hydrazine with ketones and aldehydes, although in practice they are often made by alternative routes. Ketazines are azines derived from ketones. For example, acetone azine is the simplest ketazine. Aldazines are azines derived from aldehydes.

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

Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.

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.

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">Phthalimide</span> Organic Compound

Phthalimide is the organic compound with the formula C6H4(CO)2NH. It is the imide derivative of phthalic anhydride. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. It is used as a precursor to other organic compounds as a masked source of ammonia.

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

Xylitol pentanitrate (XPN) is a nitrated ester primary explosive first synthesized in 1891 by Gabriel Bertrand. 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.

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

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.

<span class="mw-page-title-main">Pentazenium</span> Polytomic cation (N–N–N–N–N)

In chemistry, the pentazenium cation is a positively-charged polyatomic ion with the chemical formula N+5 and structure N−N−N−N−N. Together with solid nitrogen polymers and the azide anion, it is one of only three poly-nitrogen species obtained in bulk quantities.

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

Calcium perchlorate is classified as a metal perchlorate salt with the molecular formula Ca(ClO4)2. It is an inorganic compound that is a yellow-white crystalline solid in appearance. As a strong oxidizing agent, it reacts with reducing agents when heated to generate heat and products that may be gaseous. Calcium perchlorate has been categorized as having explosive reactivity. Ca(ClO4)2 is a common chemical on the soil of planet Mars, counting for almost 1% of the Martian dust, by weight.

<span class="mw-page-title-main">Hydrazinium</span> Cation

Hydrazinium is the cation with the formula [N2H5]+. This cation has a methylamine-like structure. It can be derived from hydrazine by protonation. Hydrazinium is a weak acid with pKa = 8.1.

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

Nickel hydrazine nitrate (NHN), (chemical formula: [Ni(N2H4)3](NO3)2 is an energetic material having explosive properties in between that of primary explosive and a secondary explosive. It is a salt of a coordination compound of nickel with a reaction equation of 3N2H4·H2O + Ni(NO3)2 →〔Ni(N2H4)3〕(NO3)2 + 3H2O

Azidotetrazolate (CN7) is an anion which forms a highly explosive series of salts. The ion is made by removing a proton from 5-azido-1H-tetrazole. The molecular structure contains a five-membered ring with four nitrogen atoms, and an azido side chain connected to the carbon atom. Several salts exist, but they are unstable and spontaneously explode. Rubidium azidotetrazolate was so unstable that it explodes while crystallizing. The potassium and caesium salt also spontaneously explode when dry.

References

  1. Inorganic Syntheses Volume IV. McGraw-Hill Book Company, Inc. 1953. p. 35. ISBN   9780470132678.
  2. 1 2 3 4 5 6 Kurzer, Frederick; Michael Wilkinson (February 1970). "Chemistry of carbohydrazide and thiocarbohydrazide". Chemical Reviews. 70 (1): 111–149. doi:10.1021/cr60263a004. PMID   4391877.
  3. Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi : 10.1002/14356007.a13_177.
  4. Ottersen, T.; Hope, H. "The Structure and Electron Deformation Density Distribution of Carbonohydrazide (Carbohydrazide) at 85 K" Acta Crystallographica B 1979, volume 35, p373-p378. doi : 10.1107/S0567740879003575
  5. Buecker, Brad (1997). Power Plant Water Chemistry A Practical Guide. PennWell Publishing Company. pp. 13–16. ISBN   978-0-87814-619-2.
  6. "Patent US4269717" . Retrieved 8 October 2012.
  7. "Patent US2970899" . Retrieved 8 October 2012.
  8. Fischer, Niko; Klapötke, Thomas M.; Stierstorfer, Jörg (June 2011). "Explosives Based on Diaminourea". Propellants, Explosives, Pyrotechnics. 36 (3): 225–232. doi:10.1002/prep.201100001. S2CID   97871632.
  9. Joas, Manuel; Klapötke, Thomas M. (April 2015). "Laser Initiation of Tris(carbohydrazide)metal(II) Perchlorates and Bis(carbohydrazide)diperchloratocopper(II)". Propellants, Explosives, Pyrotechnics. 40 (2): 246–252. doi:10.1002/prep.201400142.
  10. "MSDS" . Retrieved 8 October 2012.