Hydroxylamine

From Wikipedia, the free encyclopedia

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Hydroxylamine
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Names
IUPAC name
Azinous acid
Preferred IUPAC name
Hydroxylamine (only preselected[1])
Other names
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  • Aminol
  • Azanol
  • Hydroxyammonia
  • Hydroxyamine
  • Hydroxyazane
  • Hydroxylazane
  • Nitrinous acid
Identifiers
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3D model (JSmol)
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ChEBI Page Template:Plainlist/styles.css has no content.
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EC Number Page Template:Plainlist/styles.css has no content.
478
KEGG Page Template:Plainlist/styles.css has no content.
MeSH Hydroxylamine
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  • InChI=1S/H3NO/c1-2/h2H,1H2 checkY
    Key: AVXURJPOCDRRFD-UHFFFAOYSA-N checkY
  • InChI=1/H3NO/c1-2/h2H,1H2
    Key: AVXURJPOCDRRFD-UHFFFAOYAD
  • NO
Properties
Page Module:Chem2/styles.css has no content.NH2OH
Molar mass 33.030 g·mol−1
Appearance Vivid white, opaque crystals
Density 1.21 g cm−3 (at 20 °C)[2]
Melting point 33 °C (91 °F; 306 K)
Boiling point 58 °C (136 °F; 331 K) /22 mm Hg (decomposes)
Soluble
log P −0.758
Acidity (pKa) 6.03 (Page Module:Chem2/styles.css has no content.[NH3OH]+)
Basicity (pKb) 7.97
Structure
Tricoordinated at N, dicoordinated at O
Trigonal pyramidal at N, bent at O
0.67553 D
Thermochemistry
46.47 J/(K·mol)
236.18 J/(K·mol)
−39.9 kJ/mol
Hazards
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2
1
3
Flash point 129 °C (264 °F; 402 K)
265 °C (509 °F; 538 K)
Lethal dose or concentration (LD, LC):
408 mg/kg (oral, mouse); 59–70 mg/kg (intraperitoneal mouse, rat); 29 mg/kg (subcutaneous, rat)[3]
Safety data sheet (SDS) ICSC 0661
Related compounds
Related hydroxylammonium salts
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula Page Module:Chem2/styles.css has no content.NH2OH. The compound exists as hygroscopic colorless crystals.[4] Hydroxylamine is almost always provided and used as either an aqueous solution or, more often, as one of its salts, such as hydroxylammonium sulfate, a water-soluble solid.

Hydroxylamine and its salts are consumed almost exclusively to produce Nylon-6. The oxidation of Page Module:Chem2/styles.css has no content.NH3 to hydroxylamine is a step in biological nitrification.[5]

History

Hydroxylamine was first prepared as hydroxylammonium chloride in 1865 by the German chemist Wilhelm Clemens Lossen (1838-1906); he reacted tin and hydrochloric acid in the presence of ethyl nitrate.[6] It was first prepared in pure form in 1891 by the Dutch chemist Lobry de Bruyn and by the French chemist Léon Maurice Crismer (1858-1944).[7][8] The coordination complex Page Module:Chem2/styles.css has no content.ZnCl2(NH2OH)2 (zinc dichloride di(hydroxylamine)), known as Crismer's salt, releases hydroxylamine upon heating.[9]

Structure

Hydroxylamine and its N-substituted derivatives are pyramidal at nitrogen, with bond angles very similar to those of amines. The most stable conformation of hydroxylamine has the NOH anti to the lone pair on nitrogen, seeming to minimize the repulsion between the nitrogen and oxygen lone pairs.[10]

Production

Hydroxylamine or its salts (salts containing hydroxylammonium cations Page Module:Chem2/styles.css has no content.[NH3OH]+) can be produced via several routes but only two are commercially viable. It is also produced naturally as discussed in a section on biochemistry.

From nitric oxide

Page Module:Chem2/styles.css has no content.NH2OH is mainly produced as its sulfuric acid salt, hydroxylammonium sulfate (Page Module:Chem2/styles.css has no content.[NH3OH][SO4]), by the hydrogenation of nitric oxide over platinum catalysts in the presence of sulfuric acid.[11]

Page Module:Chem2/styles.css has no content.2 NO + 3 H2 + H2SO4 → [NH3OH]2[SO4]

Raschig process

Another route to Page Module:Chem2/styles.css has no content.NH2OH is the Raschig process: aqueous ammonium nitrite is reduced by Page Module:Chem2/styles.css has no content.HSO−3 and Page Module:Chem2/styles.css has no content.SO2 at 0 °C to yield a hydroxylamido-N,N-disulfonate anion:

Page Module:Chem2/styles.css has no content.[NH4]+[NO2]− + 2 SO2 + NH3 + H2O → [NH4]2[HON(SO3)2]

This ammonium hydroxylamine disulfonate anion is then hydrolyzed to give hydroxylammonium sulfate:

Page Module:Chem2/styles.css has no content.[NH4]2[HON(SO3)2] + 2 H2O → [HONH3]2SO4

Other methods

Julius Tafel discovered that hydroxylamine hydrochloride or sulfate salts can be produced by electrolytic reduction of nitric acid with HCl or Page Module:Chem2/styles.css has no content.H2SO4 respectively:[12][13]

Page Module:Chem2/styles.css has no content.HNO3 + 3 H2 → NH2OH + 2 H2O

Hydroxylamine can also be produced by the reduction of nitrous acid or potassium nitrite with bisulfite:

Page Module:Chem2/styles.css has no content.HNO2 + 2 HSO−3 → N(OH)(OSO−2)2 + H2O → NH(OH)(OSO−2) + HSO−4
Page Module:Chem2/styles.css has no content.NH(OH)(OSO−2) + [H3O]+ → [NH3OH]+ + HSO−4 (100 °C, 1 h)

Hydrochloric acid disproportionates nitromethane to hydroxylamine hydrochloride and carbon monoxide via the hydroxamic acid.[citation needed]

A direct lab synthesis of hydroxylamine from molecular nitrogen in water plasma was demonstrated in 2024.[14]

Isolation of hydroxylamine

Solid Page Module:Chem2/styles.css has no content.NH2OH can be collected by treatment with liquid ammonia. Ammonium sulfate, Page Module:Chem2/styles.css has no content.[NH4]2SO4, a side-product insoluble in liquid ammonia, is removed by filtration; the liquid ammonia is evaporated to give the desired product.[4] The net reaction is:

Page Module:Chem2/styles.css has no content.2 NO−2 + 4 SO2 + 6 H2O + 6 NH3 → 4 SO2−4 + 6 [NH4]+ + 2 NH2OH

Base, such as sodium butoxide, can be used to free the hydroxylamine from hydroxylammonium chloride:[4]

Page Module:Chem2/styles.css has no content.[NH3OH]Cl + NaO(CH2)3CH3 → NH2OH + NaCl + CH3(CH2)3OH

Reactions

Hydroxylamine is a base with a pKa of 6.03:

Page Module:Chem2/styles.css has no content.NH3OH+ ⇌ NH2OH + H+

Hydroxylamine reacts with alkylating agents usually at the nitrogen atom:

Page Module:Chem2/styles.css has no content.R−X + NH2OH → R−NH−OH + HX[citation needed]

The reaction of Page Module:Chem2/styles.css has no content.NH2OH with an aldehyde or ketone produces an oxime.

Page Module:Chem2/styles.css has no content.R2C=O + NH2OH → R2C=N−OH + H2O

This reaction can be useful in the purification of ketones and aldehydes: if hydroxylamine is added to an aldehyde or ketone in solution, an oxime forms, which generally precipitates from solution; heating the precipitate with aqueous acid then restores the original aldehyde or ketone.[15]

Page Module:Chem2/styles.css has no content.NH2OH reacts with chlorosulfonic acid to give hydroxylamine-O-sulfonic acid:[16]

Page Module:Chem2/styles.css has no content.HO−S(=O)2−Cl + NH2OH → NH2−O−S(=O)2−OH + HCl

In aqueous solution, hydroxylamine is predicted to coexist with a tautomer, the amine oxide Page Module:Chem2/styles.css has no content.H3N+−O− (ammonia oxide).[17] The solvated ammonia oxide form has variously been estimated to be less stable by 0.9–3.5 kcal·mol−1.[18] It is absent from the gas phase, where the predicted stability gap is 27.6 kcal·mol−1.[19]

Functional group

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File:Hydroxylamine-group-2D.png
Secondary N,N-hydroxylamine schema

Hydroxylamine derivatives substituted in place of the hydroxyl or amine hydrogen are (respectively) called O- or N‑hydroxyl­amines. In general N‑hydroxyl­amines are more common. Examples are N‑tert‑butyl­hydroxyl­amine or the glycosidic bond in calicheamicin. N,O‑Dimethyl­hydroxylamine is a precursor to Weinreb amides.

Similarly to amines, one can distinguish hydroxylamines by their degree of substitution: primary, secondary and tertiary. When stored exposed to air for weeks, secondary hydroxylamines degrade to nitrones.[20]

N‑organyl­hydroxyl­amines, Page Module:Chem2/styles.css has no content.R−NH−OH, where R is an organyl group, can be reduced to amines Page Module:Chem2/styles.css has no content.R−NH2:[21]

Page Module:Chem2/styles.css has no content.R−NH−OH (Zn, HCl) → R−NH2 + ZnO

Oximes such as dimethylglyoxime are also employed as ligands.

Synthesis

The hydrolysis of N-substituted oximes, hydroxamic acids, and nitrones easily provides hydroxylamines.

Alkylating of hydroxylamine or N-alkylhydroxylamines proceeds usually at nitrogen. One challenge is dialkylation when only monoalkylation is desired.

Page Module:Chem2/styles.css has no content.RNHOH + R'X → RR'NOH + HX

For O-alkylation of hydroxylamines, strong base such as sodium hydride is required to first deprotonate the OH group:[22]

Page Module:Chem2/styles.css has no content.RNHOH + NaH → RNHONa + H2
Page Module:Chem2/styles.css has no content.RNHONa + R'X → RNHOR' + NaX

Amine oxidation with benzoyl peroxide is a common method to synthesize hydroxylamines. Care must be taken to prevent over-oxidation to a nitrone. Other methods include:

Uses

File:Beckmann-rearangement (cropped).png
Conversion of cyclohexanone to caprolactam involving the Beckmann rearrangement.

Approximately 95% of hydroxylamine is used in the synthesis of cyclohexanone oxime, a precursor to Nylon 6.[11] The treatment of this oxime with acid induces the Beckmann rearrangement to give caprolactam.[23] The latter can then undergo a ring-opening polymerization to yield Nylon 6.[24]

File:Celanese synthesis of paracetamol.svg
Synthesis of paracetamol, with a Beckmann Rearrangement as the final step

An alternative industrial synthesis of paracetamol developed by Hoechst–Celanese involves the conversion of ketone to a ketoxime with hydroxylamine.

Some non-chemical uses include removal of hair from animal hides and photographic developing solutions.[2] In the semiconductor industry, hydroxylamine is often a component in the "resist stripper", which removes photoresist after lithography.

Laboratory uses

Hydroxylamine and its salts are commonly used as reducing agents in myriad organic and inorganic reactions. They can also act as antioxidants for fatty acids.

High concentrations of hydroxylamine are used by biologists to introduce mutations by acting as a DNA nucleobase amine-hydroxylating agent.[25] In is thought to mainly act via hydroxylation of cytidine to hydroxyaminocytidine, which is misread as thymidine, thereby inducing C:G to T:A transition mutations.[26] But high concentrations or over-reaction of hydroxylamine in vitro are seemingly able to modify other regions of the DNA & lead to other types of mutations.[26] This may be due to the ability of hydroxylamine to undergo uncontrolled free radical chemistry in the presence of trace metals and oxygen, in fact in the absence of its free radical effects Ernst Freese noted hydroxylamine was unable to induce reversion mutations of its C:G to T:A transition effect and even considered hydroxylamine to be the most specific mutagen known.[27] Practically, it has been largely surpassed by more potent mutagens such as EMS, ENU, or nitrosoguanidine, but being a very small mutagenic compound with high specificity, it found some specialized uses such as mutation of DNA packed within bacteriophage capsids,[28] and mutation of purified DNA in vitro.[29]

Hydroxylamine can also be used to better characterize the nature of a post-translational modification onto proteins. For example, poly(ADP-Ribose) chains are sensitive to hydroxylamine when attached to glutamic or aspartic acids but not sensitive when attached to serines.[30] Similarly, ubiquitin molecules bound to serines or threonines residues are sensitive to hydroxylamine, but those bound to lysine (isopeptide bond) are resistant.[31]

Biochemistry

In biological nitrification, the oxidation of Page Module:Chem2/styles.css has no content.NH3 to hydroxylamine is mediated by the ammonia monooxygenase (AMO).[5] Hydroxylamine oxidoreductase (HAO) further oxidizes hydroxylamine to nitrite.[32]

Cytochrome P460, an enzyme found in the ammonia-oxidizing bacteria Nitrosomonas europea, can convert hydroxylamine to nitrous oxide, a potent greenhouse gas.[33]

Hydroxylamine can also be used to highly selectively cleave asparaginyl-glycine peptide bonds in peptides and proteins.[34] It also bonds to and permanently disables (poisons) heme-containing enzymes. It is used as an irreversible inhibitor of the oxygen-evolving complex of photosynthesis on account of its similar structure to water.

Safety and environmental concerns

Hydroxylamine is a skin irritant but is of low toxicity.

A detonator can easily explode aqueous solutions concentrated above 80% by weight, and even 50% solution might prove detonable if tested in bulk.[35][36] In air, the combustion is rapid and complete:

Page Module:Chem2/styles.css has no content.4 NH2OH + O2 → 2 N2 + 6 H2O

Absent air, pure hydroxylamine requires stronger heating and the detonation does not compete combustion:

Page Module:Chem2/styles.css has no content.3 NH2OH → N2 + NH3 + 3 H2O

At least two factories dealing in hydroxylamine have been destroyed since 1999 with loss of life.[37] It is known, however, that ferrous and ferric iron salts accelerate the decomposition of 50% Page Module:Chem2/styles.css has no content.NH2OH solutions.[38] Hydroxylamine and its derivatives are more safely handled in the form of salts.

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.[39]

See also

References

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  39. ^ MSDS Sigma-Aldrich

Further reading

  • Hydroxylamine[permanent dead link]
  • Walters, Michael A. and Andrew B. Hoem. "Hydroxylamine." e-Encyclopedia of Reagents for Organic Synthesis. 2001.
  • Schupf Computational Chemistry Lab
  • M. W. Rathke A. A. Millard "Boranes in Functionalization of Olefins to Amines: 3-Pinanamine" Organic Syntheses, Coll. Vol. 6, p. 943; Vol. 58, p. 32. (preparation of hydroxylamine-O-sulfonic acid).

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