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Hydroxylamine
Hydroxylamine
Hydroxylamine
IUPAC namehydroxylamine
Identifiers
CAS number[7803-49-8]
PubChem787
SMILESNO
Properties
Molecular formulaNH2OH
Molar mass33. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 0298 g/mol
Appearancewhite needles or flakes
Density1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 21 g cm−3
Melting point

33 °C

Boiling point

110 °C

Solubility in watersoluble in cold water,
decomposes in hot water
Structure
Dipole moment0. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 67553 debye
Thermochemistry
Std enthalpy of
formation ΔfHo298		−39. The standard enthalpy of formation or "standard heat of formation" of a compound is the change of Enthalpy that accompanies the formation of 1 mole of a 9 kJ/mol
Standard molar
entropy So298		 ? J K−1 mol−1
Hazards
EU classificationXn, N
NFPA 704
3
3
1
 
R-phrasesR5, R22, R37/38, R41, R43, R48/22, R50
S-phrases(S2), S22, S26, S36/37/39, S61
Related compounds
Related compoundsHydroxylamine hydrochloride

Hydroxylamine sulfate

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Hydroxylamine is a reactive chemical with formula NH2OH. In Chemistry, the standard molar entropy is the Entropy content of one mole of substance under standard conditions (not standard temperature and pressure Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws regulations and administrative provisions relating to the classification packaging and labelling Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes It can be considered a hybrid of ammonia and water due to parallels it shares with each. Ammonia is a compound with the formula N[[hydrogen H3]] It is normally encountered as a Gas with a characteristic pungent Odor Water is a common Chemical substance that is essential for the survival of all known forms of Life. At room temperature pure NH2OH is ordinarily a white, unstable crystalline, hygroscopic compound;[1] however it is almost always encountered as an aqueous solution. In Materials science, a crystal is a Solid in which the constituent Atoms Molecules or Ions are packed in a regularly ordered repeating Hygroscopy is the ability of a substance to attract Water Molecules from the surrounding environment through either absorption or Adsorption

Hydroxylamine tends to be explosive, and the nature of the hazard is not entirely understood. An explosive material is a material that either is chemically or otherwise Energetically unstable or produces a sudden expansion of the material usually accompanied At least two factories dealing in hydroxylamine have been destroyed since 1999 with loss of life. [2] It is known, however, that ferrous and ferric iron salts accelerate the decomposition of 50% NH2OH solutions. Iron (ˈаɪɚn is a Chemical element with the symbol Fe (ferrum and Atomic number 26 Hydroxylamine and its derivatives are more safely handled in the form of salts. Salt is a Dietary mineral composed primarily of Sodium chloride that is essential for Animal life but toxic to most land plants

NH2OH is an intermediate in biological nitrification. Nitrification is the biological oxidation of Ammonia with oxygen into Nitrite followed by the oxidation of these nitrites into Nitrates Degradation The oxidation of NH3 is mediated by hydroxylamine oxidoreductase (HAO).

Contents

Production

NH2OH can be synthesized via several routes:

Raschig synthesis: Aqueous ammonium nitrite is reduced by HSO4−/SO2 at 0°C to yield a hydroxylamido-N,N-disulfate anion, which can be hydrolyzed to give (NH3OH)2SO4. Ammonium nitrite, NH4NO2 is a Salt which contains Ammonium and Nitrite ions

NH4NO2 + 2SO2 + NH3 + H2O → [NH4]2[N(OH)(OSO2)2]
[NH4]+2[N(OH)(OSO2)2]2− + H2O → [NH4][NH(OH)(OSO2)] + [NH4][HSO4]
2[NH4]+[NH(OH)(OSO2)]− + 2H2O → [NH3(OH)]2[SO4] + [NH4]2[SO4]

Solid NH2OH can be collected by treatment with liquid ammonia. Ammonium sulfate is insoluble in liquid ammonia and is removed by filtration; the liquid ammonia is evaporated to give the desired product. Ammonium sulfate, (NH42SO4 is an inorganic chemical compound commonly used as a fertilizer Ammonia is a compound with the formula N[[hydrogen H3]] It is normally encountered as a Gas with a characteristic pungent Odor [1]

Another method of synthesis is to make hydroxylammonium salts which can then be converted to hydroxylamine.

[NH3(OH)]Cl + NaOBu → NH2OH + NaCl + BuOH[1]

The reduction of nitrous acid or potassium nitrate with bisulfite:

HNO2 + 2 HSO3− → [N(OH)(OSO2)2]2− + H2O → [NH(OH)(OSO2)]− + [HSO4]−
[NH(OH)(OSO2)]− + H3O+ (100 °C/1 h) → [NH3(OH)]+ + [HSO4]−

Reactions

Hydroxylamine reacts with electrophiles, such as an alkylating agents, which can attach at either the O or N position. Nitrous acid (molecular formula H[[Nitrogen N]] O 2 is a weak and monobasic Acid known only in Solution and in the form of Nitrite Potassium nitrate is a Chemical compound with the Chemical formula K[[Nitrogen N]] O 3 Bisulfite ion ( IUPAC -recommended nomenclature hydrogen sulfite) is the ion HSO3− In Chemistry, an electrophile (literally electron-lover) is a Reagent attracted to Electrons that participates in a chemical reaction by accepting Alkylation is the transfer of an Alkyl group from one Molecule to another

R-X + NH2OH → R-ONH2 + HX
R-X + NH2OH → R-NHOH + HX

The reaction of NH2OH with an aldyhyde or ketone produces an oxime. oxime is one in a class of Chemical compounds with the general formula R1R2 C[[nitrogen N]] O[[hydrogen H]] where R1 is an

R2C=O + NH2OH∙HCl , NaOH → R2C=NOH + NaCl + H2O

This reaction is useful in the purification of ketones and aldehydes, Oximes also are employed as ligands, e. oxime is one in a class of Chemical compounds with the general formula R1R2 C[[nitrogen N]] O[[hydrogen H]] where R1 is an In Chemistry, a ligand is either an Atom, Ion, or Molecule (see also Functional group) that bonds to a central metal generally g. dimethylglyoxime. Dimethylglyoxime is a Chemical compound described by the formula CH3C(NOHC(NOHCH3

NH2OH reacts with chlorosulfuric acid to give hydroxylamine-O-sulfonic acid, a useful reagent for the synthesis of caprolactam. Caprolactam is an Organic compound which is a Lactam of 6-aminohexanoic acid (ε-aminohexanoic acid Aminocaproic acid)

HOSO2Cl + NH2OH → NH2OS2OH + HCl

The hydroxylamine-O-sulfonic acid, which should be stored at 0 °C, can be checked by iodometric titration.

Hydroxylamine (NH2OH), or hydroxylamines (R-NHOH) can be reduced to amines. Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. [3]

NH2OH (Zn/HCl) → NH3
R-NHOH (Zn/HCl) → R-NH2

Uses

Hydroxylamine and its salts are commonly used as reducing agents in a myriad of organic and inorganic reactions. They can also act as antioxidants for fatty acids. Some non-chemical uses include removal of hair from animal hides and photography developing solutions. [4]

The nitrate salt, hydroxylammonium nitrate, is being researched as a rocket propellant, both in water solution as a monopropellant and in its solid form as a solid propellant. Hydroxylammonium nitrate or hydroxylamine nitrate (HAN is an energetic chemical with the chemical formula NH3OHNO3 Monopropellants are Propellants composed of chemicals or mixtures of chemicals which can be stored in a single container with some degree of safety A solid rocket or a solid-fuel rocket is a Rocket with a motor that uses solid propellants ( Fuel / Oxidizer)

This has also been used in the past by biologists to introduce random mutations by switching base pairs from A to G, or from C to T. This is to probe functional areas of genes to elucidate what happens if their functions are broken. Nowadays other mutagens are used. Hydroxylamine can also be used to highly selectively cleave asparaginyl-glycine peptide bonds in peptides and proteins. Asparagine (abbreviated as Asn or N; Asx or B represent either asparagine or Aspartic acid) is one of the 20 most common natural Glycine (abbreviated as Gly or G) is the Organic compound with the formula NH2CH2COOH It also bonds to and permanently disables (poisons) heme-containing enzymes. A hemoprotein (also haemoprotein) or Heme Protein, is a Metalloprotein containing a heme Prosthetic group, either covalently It is used as an irreversible inhibitor of the oxygen-evolving complex of photosynthesis on account of its similar structure to water. The oxygen evolving complex, (OEC also known as the water-splitting complex is a water oxidizing enzyme involved in the photooxidation of water during the Light reactions

In the semiconductor industry, hydroxylamine is often a component in the "resist stripper" which removes photoresist after lithography.

Safety

Hydroxylamine may explode on heating. It is an irritant to the respiratory tract, skin, eyes, and other mucous membranes. It may be absorbed through the skin, is harmful if swallowed, and is a possible mutagen. [5]

See also

References

  1. ^ a b c Greenwood and Earnshaw. Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. Chemistry of the Elements. 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431-432. 1997.
  2. ^ Japan Science and Technology Agency Failure Knowledge Database.
  3. ^ Smith, Michael and Jerry March. March's advanced organic chemistry : reactions, mechanisms, and structure. New York. Wiley. p. 1554. 2001.
  4. ^ Patnaik, Pradyot. Handbook of Inorganic Chemicals. McGraw Hill. pp. 385-386. 2003.
  5. ^ MSDS Sigma-Aldrich

External links

Dictionary

hydroxylamine

-noun

  1. (inorganic chemistry) An explosive inorganic derivative of ammonia, NH2OH, used as a reducing agent, and in organic synthesis.
  2. (organic chemistry) Any organic derivative of this compound.
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