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Hydroxylamine is the hydroxyl derivative of ammonia.
Hydroxylamine is used as a nucleophile in aromatic substitution reactions and as a reducing agent.
By the reaction with aldehydes, hydroxylamine forms oximes, which are intermediates in the commercial production of polyamide plastics.
CAS: 7803-49-8
MF: H3NO
MW: 33.03
EINECS: 232-259-2
Synonyms
hydroxylamine,freebase;hydroxylaminefree-base;NH2OH;Oxammonium;Oxyammonia;FH-50;FH-50TM;HYDROXYLAMINE
Some hydroxylamine converted oximes are used in smaller amounts as pharmaceuticals, pesticides, and varnishes to prevent formation of a skin.
With Hydroxylamine is reduction ability, hydroxylamine is used as an antioxidant in photographic developers, to stabilize polymerization monomers, and to reduce Cu2+ in the dyeing of acrylic fibers.
Hydroxylamine can be converted into hydroxylamine-O-sulphonic acid, which is a good aminating agent.
Hydroxylamine can also be used as an intermediate in nitrification.
Hydroxylamine is further used in semiconductor industry in the cleaning formations, such as for aluminum interconnect.
Hydroxylamine was first synthesized by Wilhem Clemens Lossen in 1865 in the laboratory of Wilhelm Heinrich Heintz while working in Halle.
The Lossen synthesis originally generated hydroxylamine in aqueous solution.
Anhydrous hydroxylamine was prepared later by Lobry de Bruyn and Crismer in 1891.
The free base is extremely volatile, and industrial-scale production has been fraught with problems, including large explosions at facilities in the United States and Japan.
Much of the hydroxylamine produced and transported is in salt form or as a dilute aqueous solution.
The simplest hydroxylamine, consisting of ammonia bearing a hydroxy substituent.
Hydroxylamine is an intermediate in the biological nitrification by microbes like bacteria.
A colourless solid,NH2OH, m.p. 33°C.
Hydroxylamine explodes onheating and may be employed as anoxidizing agent or reducing agent.
Hydroxylamine is made by the reduction of nitratesor nitrites, and is used in makingnylon.
With aldehydes and ketones itforms oximes.
Hydroxylamine is an organic compound with the formula NH2OH, characterized by the presence of both an amine and an alcohol functional group.
Hydroxylamine appears as a colorless, crystalline solid that is hygroscopic and soluble in water and alcohols.
Hydroxylamine is known for its reducing properties and is often used in organic synthesis, particularly in the formation of oximes from carbonyl compounds.
Hydroxylamine can also act as a nucleophile in various chemical reactions.
Hydroxylamine is relatively stable under normal conditions but can decompose under acidic or basic conditions, releasing nitrogen gas.
Hydroxylamine is also recognized for its role in biological systems, where it can participate in the metabolism of certain amino acids.
However, Hydroxylamine is important to handle hydroxylamine with care, as it can be hazardous; it is classified as a potential explosive when concentrated and can cause irritation upon contact with skin or eyes.
Proper safety measures should be taken when working with Hydroxylamine in laboratory settings.
Hydroxylamine is a selective Monoamine oxidase (MAO) inhibitor used for inhibiting of platelet aggregation.
Hydroxylamine is a intermediate of nitrogen cycle in aerobic ammonium oxidizers microorganisms, such as ammonium oxidizing bacteria (AOB), ammonium oxidizing archaea (AOA) and complete ammonium oxidizing bacteria (comammox).
Hydroxylamine impacts NO and N2O emissions by aerobic ammonium oxidizers microorganisms and inhibits nitrite oxidizing bacteria (NOB) activity.
Hydroxylamine solution, 50 wt. % in H2O, is a versatile chemical compound widely utilized in various industrial and research applications.
This aqueous solution of hydroxylamine is known for its reducing properties, making it an essential reagent in organic synthesis, particularly in the preparation of oximes from aldehydes and ketones.
Hydroxylamine's ability to act as a nucleophile allows it to participate in a range of chemical reactions, including the synthesis of pharmaceuticals, agrochemicals, and fine chemicals.
Researchers appreciate its role in the reduction of nitro compounds to amines, which is crucial in the development of numerous chemical products.
In addition to its synthetic applications, hydroxylamine solution is also employed in analytical chemistry for the determination of carbonyl compounds and as a stabilizer in the formulation of certain polymers.
Its unique properties make Hydroxylamine a valuable tool for chemists seeking efficient and effective solutions in their work.
With its high purity and concentration, this hydroxylamine solution is ideal for both laboratory and industrial use, providing reliable results and enhancing productivity in various chemical processes.
Hydroxylamine Chemical Properties
Melting point: 7°C
Boiling point: >100 °C
density: 1.078 g/mL at 25 °C
vapor pressure: 9 mm Hg ( 40 °C)
refractive index: n20/D 1.393
RTECS: NC2975000
storage temp.: Store below +30°C.
solubility: Water
form: white flakes or needles
pka: pK (20°) 7.97
color: white orthorhombic flakes or needles
PH: 10.6 (20°C in H2O)
Water Solubility: Miscible with water, liquid ammonia and methanol. Slightly miscible with ether, benzene, carbon disulfide and chloroform.
Merck: 13,4853
Stability: Stable. Incompatible with oxidizing agents, potassium dichromate, chromium trioxide, zinc, calcium, copper, sodium, ammonia, carbonyls, phosphorus halides, pyridine, hypochlorites.
InChI: 1S/H3NO/c1-2/h2H,1H2
InChIKey: AVXURJPOCDRRFD-UHFFFAOYSA-N
CAS DataBase Reference: 7803-49-8(CAS DataBase Reference)
NIST Chemistry Reference: Hydroxylamine(7803-49-8)
EPA Substance Registry System: Hydroxylamine (7803-49-8)
Physical properties
White crystalline solid; orthogonal plates or needles; unstable; density 1.21g/cm3at 20°C; melts at 33°C; vaporizes at 58°C; very soluble in water, liquidammonia and lower alcohols; sparingly soluble in most other organic solvents;decomposes in hot water; pKa5.94 at 25°C.
Uses
Reducing agent used in photographic processing, leather tanning, manufacturing of nylon and other polymers; as a stabilizer for natural rubber; to prevent the development of objectionable tastes and odors during the refining of fatty materials.
Hydroxylamine is used as a reducing agent in photography, in synthetic and analytical chemistry, as an antioxidant for fatty acids and soaps, and as a dehairing agent for hides.
In addition, hydroxylamine is used in the production of cyclohexanone oxime, an isomer of caprolactam, which is an intermediate in the production of nylon-6.
In the semiconductor industry, hydroxylamine can be a component of a solution that dissolves a photoresist following lithography.
Hydroxylamine can also be used to selectively cleave asparaginyl-glycine peptide bonds.
Preparation
Hydroxylamine is unstable as a free base.
Hydroxylamine is prepared from hydroxy-lamine hydrochloride, NH2OHHCl, which is obtained by electrolytic reduc-tion of ammonium chloride solution.
The hydrochloride undergoes alkalinedecomposition to hydroxylamine, which is collected by vacuum distillation.
Reactivity Profile
Hydroxylamine is a white solid, thermally unstable, decomposes rapidly at room temperature or when dissolved in hot water by internal oxidation-reduction.
Hydroxylamine should be stored below 10° C.
Explosive reaction with strong oxidizers (chromium trioxide, potassium dichromate) or powdered zinc upon heat.
Reaction with zinc or calcium produces explosive bishydroxylamides.
Hydroxylamine ignites on contact with cupric sulfate, alkali metals (sodium, potassium), oxidants (e.g., barium oxide, barium peroxide, lead dioxide, potassium permanganate, chlorine), phosphorus trichloride and pentachloride.
Hydroxylamine reacts vigorously with hypochlorites, pyridine, carbonyls.
On contact with organic materials in thin layer (e.g., crystals on filter paper), Hydroxylamine may ignite spontaneously in air.
Hydroxylamine explodes when heated above 70° C.
During a distillation process, an explosion occurred.
Potassium hydroxide is thought to be involved in the explosion.
Employees in the plant complained of chest pains and suffered chemical burns.
Five people were killed by the explosion.
