Nitrogen trichloride

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Nitrogen trichloride
Structural formula of nitrogen trichloride NCl3 dimensions.svg
Structural formula of nitrogen trichloride
Space-filling model of nitrogen trichloride Nitrogen-trichloride-3D-vdW.png
Space-filling model of nitrogen trichloride
   Nitrogen, N
   Chlorine, Cl
Nitrogen trichloride Nitrogen trichloride.JPG
Nitrogen trichloride
Names
Other names
Trichloramine
Agene
Nitrogen(III) chloride
Trichloroazane
Trichlorine nitride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.030.029 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 233-045-1
1840
PubChem CID
RTECS number
  • QW974000
UNII
  • InChI=1S/Cl3N/c1-4(2)3 Yes check.svgY
    Key: QEHKBHWEUPXBCW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/Cl3N/c1-4(2)3
    Key: QEHKBHWEUPXBCW-UHFFFAOYAZ
  • ClN(Cl)Cl
Properties
NCl3
Molar mass 120.36 g·mol−1
Appearanceyellow oily liquid
Odor chlorine-like
Density 1.653 g/mL
Melting point −40 °C (−40 °F; 233 K)
Boiling point 71 °C (160 °F; 344 K)
immiscible
slowly decomposes
Solubility soluble in benzene, chloroform, CCl4, CS2, PCl3
Structure
orthorhombic (below −40 °C)
trigonal pyramidal
0.6 D
Thermochemistry
232 kJ/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazard OX: Oxidizer. E.g. potassium perchlorate
2
0
3
OX
93 °C (199 °F; 366 K)
Related compounds
Other anions
Nitrogen trifluoride
Nitrogen tribromide
Nitrogen triiodide
Other cations
Phosphorus trichloride
Arsenic trichloride
Related chloramines
Monochloramine
Dichloramine
Related compounds
Nitrosyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Nitrogen trichloride, also known as trichloramine, is the chemical compound with the formula NCl3. This yellow, oily, and explosive liquid is most commonly encountered as a product of chemical reactions between ammonia-derivatives and chlorine (for example, in swimming pools). Alongside monochloramine and dichloramine, trichloramine is responsible for the distinctive 'chlorine smell' associated with swimming pools, where the compound is readily formed as a product from hypochlorous acid reacting with ammonia and other nitrogenous substances in the water, such as urea from urine. [1]

Contents

Preparation and occurrence

The compound is generated by treatment of ammonium chloride with calcium hypochlorite. When prepared in an aqueous-dichloromethane mixture, the trichloramine is extracted into the nonaqueous phase. [2] Intermediates in this conversion include monochloramine and dichloramine, NH2Cl and NHCl2, respectively.

Nitrogen trichloride, trademarked as Agene, was at one time used to bleach flour, [3] but this practice was banned in the United States in 1949 due to safety concerns.

Structure and properties

Like ammonia, NCl3 is a pyramidal molecule. The N-Cl distances are 1.76 Å, and the Cl-N-Cl angles are 107°. [4]

Nitrogen trichloride can form in small amounts when public water supplies are disinfected with monochloramine, and in swimming pools by disinfecting chlorine reacting with urea in urine and sweat from bathers.

Reactions and uses

The chemistry of NCl3 has been well explored. [5] It is moderately polar with a dipole moment of 0.6 D. The nitrogen center is basic but much less so than ammonia. It is hydrolyzed by hot water to release ammonia and hypochlorous acid.

NCl3 + 3 H2O → NH3 + 3 HOCl

Concentrated samples of NCl3 can explode to give N2 and chlorine gas.[ citation needed ]

2 NCl3 → N2 + 3 Cl2

In the presence of aluminium trichloride, NCl3 react with some branch hydrocarbon to produce, after a hydrolysis step, amines. [2]

Safety

Nitrogen trichloride can irritate mucous membranesit is a lachrymatory agent, but has never been used as such. [6] [7] The compound (rarely encountered) is a dangerous explosive, being sensitive to light, heat, even moderate shock, and organic compounds. Pierre Louis Dulong first prepared it in 1812, and lost several fingers and an eye in two explosions. [8] In 1813, an NCl3 explosion blinded Sir Humphry Davy temporarily, inducing him to hire Michael Faraday as a co-worker. They were both injured in another NCl3 explosion shortly thereafter. [9]

See also

Related Research Articles

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite is an alkaline inorganic chemical compound with the formula NaOCl. It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of sodium cations and hypochlorite anions.

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

Nitrogen triiodide is an inorganic compound with the formula NI3. It is an extremely sensitive contact explosive: small quantities explode with a loud, sharp snap when touched even lightly, releasing a purple cloud of iodine vapor; it can even be detonated by alpha radiation. NI3 has a complex structural chemistry that is difficult to study because of the instability of the derivatives.

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

Hypochlorous acid is an inorganic compound with the chemical formula ClOH, also written as HClO, HOCl, or ClHO. Its structure is H−O−Cl. It is an acid that forms when chlorine dissolves in water, and itself partially dissociates, forming a hypochlorite anion, ClO. HClO and ClO are oxidizers, and the primary disinfection agents of chlorine solutions. HClO cannot be isolated from these solutions due to rapid equilibration with its precursor, chlorine.

<span class="mw-page-title-main">Hypochlorite</span> Anion

In chemistry, hypochlorite, or chloroxide is an anion with the chemical formula ClO. It combines with a number of cations to form hypochlorite salts. Common examples include sodium hypochlorite and calcium hypochlorite. The Cl-O distance in ClO is 1.69 Å.

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

Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides/oxychlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.

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

Dichlorine monoxide is an inorganic compound with the molecular formula Cl2O. It was first synthesised in 1834 by Antoine Jérôme Balard, who along with Gay-Lussac also determined its composition. In older literature it is often referred to as chlorine monoxide, which can be a source of confusion as that name now refers to the ClO radical.

Shock chlorination is a process used in many swimming pools, water wells, springs, and other water sources to reduce the bacterial and algal residue in the water. Shock chlorination is performed by mixing a large amount of sodium hypochlorite, which can be in the form of a powder or a liquid such as chlorine bleach, into the water. The common advice is that the amount added must raise the level of chlorine to 10X the level of chloramines present in the pool water; this is "shocking". A lesser ratio is termed superchlorinating. Water that is being shock chlorinated should not be swum in or drunk until the sodium hypochlorite count in the water goes down to three ppm or less which is generally more than 6 hours. Commercial sodium hypochlorite should not be mixed with commercial calcium hypochlorite, as there is a risk of explosion. Although a verb for superchlorination, "shock" is often misunderstood to be a unique type of product.

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

1-Bromo-3-chloro-5,5-dimethylhydantoin is a chemical structurally related to hydantoin. It is a white crystalline compound with a slight bromine and acetone odor and is insoluble in water, but soluble in acetone.

Monochloramine, often called chloramine, is the chemical compound with the formula NH2Cl. Together with dichloramine (NHCl2) and nitrogen trichloride (NCl3), it is one of the three chloramines of ammonia. It is a colorless liquid at its melting point of −66 °C (−87 °F), but it is usually handled as a dilute aqueous solution, in which form it is sometimes used as a disinfectant. Chloramine is too unstable to have its boiling point measured.

Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds. Two classes of compounds are considered: inorganic chloramines and organic chloramines. Chloramines are the most widely used members of the halamines.

<span class="mw-page-title-main">Gallium(III) chloride</span> Chemical compound

Gallium(III) chloride is an inorganic chemical compound with the formula GaCl3 which forms a monohydrate, GaCl3·H2O. Solid gallium(III) chloride is a deliquescent white solid and exists as a dimer with the formula Ga2Cl6. It is colourless and soluble in virtually all solvents, even alkanes, which is truly unusual for a metal halide. It is the main precursor to most derivatives of gallium and a reagent in organic synthesis.

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

Dichloramine is a reactive inorganic compound with the chemical formula NHCl2. It is one of the three chloramines of ammonia, the others being monochloramine and nitrogen trichloride. This yellow gas is unstable and reacts with many materials. It is formed by a reaction between ammonia and chlorine or sodium hypochlorite. It is a byproduct formed during the synthesis of monochloramine and nitrogen trichloride.

Nitrogen tribromide is a chemical compound with the formula NBr3. It is extremely explosive in its pure form, even at −100 °C, and was not isolated until 1975. It is a deep-red and volatile solid.

<span class="mw-page-title-main">Chlorine-releasing compounds</span> Pharmaceutical compound

Chlorine-releasing compounds, also known as chlorine base compounds, is jargon to describe certain chlorine-containing substances that are used as disinfectants and bleaches. They include the following chemicals: sodium hypochlorite, chloramine, halazone, and sodium dichloroisocyanurate. They are widely used to disinfect water and medical equipment, and surface areas as well as bleaching materials such as cloth. The presence of organic matter can make them less effective as disinfectants. They come as a liquid solution, or as a powder that is mixed with water before use.

Cobalt(III) chloride or cobaltic chloride is an unstable and elusive compound of cobalt and chlorine with formula CoCl
3
. In this compound, the cobalt atoms have a formal charge of +3.

<span class="mw-page-title-main">Europium(II) chloride</span> Chemical compound

Europium(II) chloride is an inorganic compound with a chemical formula EuCl2. When it is irradiated by ultraviolet light, it has bright blue fluorescence.

A chloride nitride is a mixed anion compound containing both chloride (Cl) and nitride ions (N3−). Another name is metallochloronitrides. They are a subclass of halide nitrides or pnictide halides.

Carbide chlorides are mixed anion compounds containing chloride anions and anions consisting entirely of carbon. In these compounds there is no bond between chlorine and carbon. But there is a bond between a metal and carbon. Many of these compounds are cluster compounds, in which metal atoms encase a carbon core, with chlorine atoms surrounding the cluster. The chlorine may be shared between clusters to form polymers or layers. Most carbide chloride compounds contain rare earth elements. Some are known from group 4 elements. The hexatungsten carbon cluster can be oxidised and reduced, and so have different numbers of chlorine atoms included.

Manganese(III) chloride is the hypothetical inorganic compound with the formula MnCl3.

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

Tetraselenium tetranitride is the inorganic compound with the formula Se4N4. Like the analogous tetrasulfur tetranitride S4N4, Se4N4 is an orange solid. It is however less soluble and more shock-sensitive than S4N4.

References

  1. "Chloramines: Understanding "Pool Smell"". American Chemistry Council . July 2006. Archived from the original on 17 December 2019. Retrieved 17 December 2019.
  2. 1 2 Kovacic, Peter; Chaudhary, Sohan S. (1968). "1-Amino-1-Methylcyclohexane". Organic Syntheses. 48: 4. doi:10.15227/orgsyn.048.0004.
  3. Hawthorn, J.; Todd, J. P. (1955). "Some effects of oxygen on the mixing of bread doughs". Journal of the Science of Food and Agriculture. 6 (9): 501–511. Bibcode:1955JSFA....6..501H. doi:10.1002/jsfa.2740060906.
  4. Holleman, A. F.; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press. ISBN   978-0-12-352651-9.
  5. Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN   978-0-08-037941-8.
  6. White, G. C. (1999). The Handbook of Chlorination and Alternative Disinfectants (4th ed.). Wiley. p. 322. ISBN   978-0-471-29207-4.
  7. "Health Hazard Evaluation Report: Investigation of Employee Symptoms at an Indoor Water Park" (PDF). NIOSH ENews. 6 (4). August 2008. HETA 2007-0163-3062.
  8. Thénard J. L.; Berthollet C. L. (1813). "Report on the work of Pierre Louis Dulong". Annales de Chimie et de Physique . 86 (6): 37–43.
  9. Thomas, J.M. (1991). Michael Faraday and The Royal Institution: The Genius of Man and Place (PBK). CRC Press. p. 17. ISBN   978-0-7503-0145-9.

Further reading