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Hydroxylamine

Hydroxylamine structure

Hydroxylamine 

structure
  • CAS No:

    7803-49-8

  • Formula:

    H3NO

  • Chemical Name:

    Hydroxylamine

  • Synonyms:

    Hydroxylamine;Hydroxyamine;Telclean 1200A;HDA;EKC 270T

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

slightly yellow liquid


Hydroxylamine is an odorless white crystalline solid. Sinks and mixes with water. (USCG, 1999)|Liquid|Solid|VERY HYGROSCOPIC WHITE NEEDLES OR FLAKES.


Hydroxylamine is an odorless white crystalline solid. Sinks and mixes with water. (USCG, 1999)|Hydroxylamine is the simplest hydroxylamine, consisting of ammonia bearing a hydroxy substituent. It is an intermediate in the biological nitrification by microbes like bacteria. It has a role as a nitric oxide donor, an EC 1.1.3.13 (alcohol oxidase) inhibitor, a nucleophilic reagent, an EC 4.2.1.22 (cystathionine beta-synthase) inhibitor, an EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor, a bacterial xenobiotic metabolite and an algal metabolite. It is a conjugate acid of a hydroxyazanide and an aminooxidanide. It derives from a hydride of an ammonia.|A colorless inorganic compound (HONH2) used in organic synthesis and as a reducing agent, due to its ability to donate nitric oxide.

Hydroxylamine Basic Attributes

33.03

33.03

232-259-2

2FP81O2L9Z

0661

2735

DTXSID7041043

Colorless cyrstals|Large white flakes or white needles

28251090

Characteristics

46.25000

-0.81

Hydroxylamine is an odorless white crystalline solid. Sinks and mixes with water. (USCG, 1999)

1.227 g/cm3

33 °C

70 °C @ Press: 60 Torr

265 °F (USCG, 1999)|explodes at 129 °C

1.395

Miscible with water, liquid ammonia and methanol. Slightly miscible with ether, benzene, carbon disulfide and chloroform.

Separate from oxidizing materials. store in a cool, dry, well-ventilated location. store away from heat, oxidizers, and sunlight. Outside or detached storage is preferred.

9 mm Hg ( 40 °C)

Relative vapor density (air = 1): 1.1

Celiac-rat LD50: 59 mg/kg; Celiac-mouse LD50: 60 mg/kg

Thermal decomposition of toxic nitrogen oxide fumes

pKa= 5.94 @ 25 °C

VERY HYGROSCOPIC; ALKALINE REACTION; DECOMP BY HOT WATER; HEAT OF FORMATION (SOLID): -27.60 KCAL/MOL AT 18 °C & 1 ATM; (LIQ): -25.5 KCAL/MOL AT 18 °C & 1 ATM|REDUCING AGENT IN ALKALINE, OXIDIZING AGENT IN ACID MEDIUM|COLORLESS MONOCLINIC CRYSTALS; BP: DECOMP; SLIGHTLY SOL IN ALC; SOL IN ETHER /SULFATE/|Decomposes in hot water|Monoclinic columnar crystals; slowly decomp when moist; density: 1.67 at 17 °C; mp: about 151 °C; pK of 0.2 molar aq soln 3.2; 1 g sol in 1 ml H2O, 19 ml alc, 8 ml methanol; sol in glycerol, propylene glycol; insol in cold ether /Hydroxylamine hydrochloride/

Decomposes rapidly at room temperature or when dissolved in hot water by internal oxidation-reduction. Reacts with water or steam to produce heat and corrosive liquids.

Bases, Strong

Explosive

HYDROXYLAMINE is a white solid, thermally unstable, decomposes rapidly at room temperature or when dissolved in hot water by internal oxidation-reduction. It should be stored below 10° C [Bailar, 1973, vol. 2, p. 272]. Explosive reaction with strong oxidizers (chromium trioxide, potassium dichromate) or powdered zinc upon heat. Reaction with zinc or calcium produces explosive bishydroxylamides. It 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. It reacts vigorously with hypochlorites, pyridine, carbonyls [Sax, 9th ed., 1996, p. 1875]. On contact with organic materials in thin layer (e.g., crystals on filter paper), it may ignite spontaneously in air. It explodes when heated above 70° C [Brauer, 1963, vol. 1, p. 502]. 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.

265 °F (USCG, 1999)

Safety Information

II

8

UN 3082 9/PG 3

3

5-22-37/38-41-43-48/22-50-40-21/22

23-26-36/37/39-47-61-22-46

NC2975000

Xn,N

Treasury is ventilated, low temperature and dry; stored separately from combustible materials

High temperature explosion

Stable. Incompatible with oxidizing agents, potassium dichromate, chromium trioxide, zinc, calcium, copper, sodium, ammonia, carbonyls, phosphorus halides, pyridine, hypochlorites.

P261-P273-P280-P305 + P351 + P338

H290-H302-H315-H317-H318-H335-H351-H373-H400

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Incompatible with carbonyls; pyridine. Vigorous reaction with hypochlorites.

A REVIEW WITH 304 REFERENCES ON CHEMICAL MECHANISMS INVOLVED IN MUTAGENESIS INDUCED BY HYDROXYLAMINE & ITS DERIVATIVES.[MARFEY P ET AL; GENETIC TOXICOLOGY OF HYDROXYLAMINES; MUTAT RES 86(2) 155 (1981)]

Special Hazards of Combustion Products: Nitrogen oxides - toxic fumes - react with water or steam to produce heat and corrosive liquids - can react violently with reducing materials. Behavior in Fire: May explode when exposed to heat or flame. Explodes at 265°F. (USCG, 1999)|Gives off irritating or toxic fumes (or gases) in a fire. Risk of explosion on heating. Risk of fire and explosion on contact with many substances. See Chemical Dangers.|Reactive - 3rd degree

|Danger|H200: Unstable Explosive [Danger Explosives]|P201, P202, P234, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P362, P363, P372, P373, P380, P390, P391, P401, P403+P233, P404, P405, and P501|H290: May be corrosive to metals [Warning Corrosive to Metals]|P201, P202, P234, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P362, P363, P390, P391, P403+P233, P404, P405, and P501|H200 (34.74%): Unstable Explosive [Danger Explosives]|Aggregated GHS information provided by 475 companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P260, P261, P264, P270, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P309+P311, P310, P312, P314, P321, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Neutralizing Agents for Acids and Caustics: Sodium bisulfate (USCG, 1999)

Wear protective clothing, cap, gloves, goggles - canister type mask recommended. (USCG, 1999)

Dangerous fire hazard when exposed to heat, flame, and oxidizers. May ignite spontaneously in air if a large surface area is exposed (e.g. precipitate on paper).|Ignites on contact with copper(II)sulfate; metals (e.g. sodium); oxidants (e.g. barium peroxide; barium oxide; lead dioxide/ potassium permanganate; chlorine); phosphorus chlorides (e.g. phosphorus trichloride; phosphorus pentachloride).

Noncombustible solid that explodes when heated to 265 °F (129 °C). ... It will decompose at high temperatures and, if confined at 284 °F (140 °C), will explode.|Explosive reaction with potassium dichromate; chromium trioxide; powdered zinc + heat. Forms the heat sensitive explosive bis(hydroxylamide) in reaction with zinc or calcium.

Not combustible. Extinguish fire using agent suitable for surrounding fire. Fight fire from protected location or maximum possible distance. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Explosive decomposition may occur under fire conditions.

Closed containers may rupture violently when heated.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|MATERIAL SHOULD BE HANDLED WITH CAUTION TO AVOID CONTACT & COMPLETE ELIMINATION OF MANUAL PROCESSES BY MECHANIZATION IS RECOMMENDED.

A corrosive irritant to the eye, skin, and mucous membranes.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered non-metallic containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Fireproof. Separated from incompatible materials. See Chemical Dangers. Cool. Dry. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is corrosive to the eyes. The substance is irritating to the skin and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in the formation of methaemoglobin and consequent anaemia. Tumours have been detected in experimental animals but may not be relevant to humans.

NO open flames, NO sparks and NO smoking. NO contact with hot surfaces.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.| 3 - Materials that in themselves are capable of detonation or explosive decomposition or explosive reaction but that require a strong initiating source or must be heated under confinement before initiation.

Toxicity

highly toxic

ARGININE...PROTECTS ANIMALS AGAINST DEATH BY HYDROXYLAMINE EVEN THOUGH THE METHEMOGLOBINEMIC RESPONSE IS UNCHANGED.

LD50 Rat ip 59 mg/kg|LD50 Rat sc 29 mg/kg|LD50 Mouse ip 60 mg/kg

Hydroxylamine's production and use as a reducing agent(1,2) and as an intermediate in the production of caprolactam(3) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 14(SRC), determined from a structure estimation method(2), indicates that hydroxylamine is expected to have very high mobility in soil(SRC). The pKa of hydroxylamine is 5.94(3) which indicates this compound will partially exist as a cation under acidic conditions, and cations have lower mobility in soil than neutral species(SRC). Volatilization of hydroxylamine from moist soil surfaces is not expected to be an important fate process since cations do not volatilize(SRC) and the neutral species has an estimated Henry's Law constant of 6.9X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of hydroxylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 53 mm Hg(5) at 32 °C.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 14(SRC), determined from a structure estimation method(2), indicates that hydroxylamine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 5.94(3) indicates hydroxylamine will partially exist as a cation in waters. Volatilization from water surfaces is not expected to be an important environmental fate process(SRC) since cations do not volatilize and the Henry's Law constant of the neutral species is 6.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 1.2(6,SRC) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hydroxylamine, which has a vapor pressure of 53 mm Hg at 32 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hydroxylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 18 hours(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of hydroxylamine with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A pKa value of 5.94(2) indicates that hydroxylamine will partially exist as a cation in moist soils and water(SRC). Abiotic degradation of hydroxylamine by photochemically produced peroxy radicals is an important environmental fate process in surface waters(3,SRC). The rate constant for this reaction has been measured as 1X10+5 L/mol-s at 30 °C(3). This corresponds to a half-life of about 2 hours for a solution concentration of 1X10-9 M of peroxy radicals(3).

An estimated BCF of 3 was calculated for hydroxylamine(SRC), using an estimated log Kow of -1.2(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for hydroxylamine can be estimated to be 14(SRC). According to a classification scheme(2), this estimated Koc value suggests that hydroxylamine is expected to have very high mobility in soil. A pKa of 5.94(3) indicates that hydroxylamine will partially exist in the protonated form in moist soils(SRC) and cations adsorb to soil stronger than neutral compounds.

The pKa for hydroxylamine is 5.94(1), which indicates this compound will partially exist in the protonated form(SRC). Volatilization from moist soils and water surfaces is not expected since cations don't volatilize and the estimated Henry's Law constant for the neutral species is 6.9X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(2). The potential for volatilization of hydroxylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 53 mm Hg(3).

...during production or in loading and unloading of crystallizers and centrifuges and in packaging of finished product.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 2,689 workers (1,481 of these are female) are potentially exposed to hydroxylamine in the US(1). Occupational exposure may occur through inhalation and dermal contact with this compound at workplaces where hydroxylamine is produced or used(SRC).

Drug Information

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG; BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). /HYDROXYLAMINE & SALTS/

INHALATION: Moderately toxic by inhalation and oral routes with the following symptoms possible: headache, vertigo, tinnitus, dyspnea, nausea and vomiting, cyanosis, proteinuria and hematuria, jaundice, restlessness, and convulsion. Methemoglobinemia has been reported. EYES: Corrosive - highly irritating. SKIN: Irritating or corrosive to skin. INGESTION: Moderately toxic by inhalation and oral routes with the following symptoms possible; headache, vertigo, tinnitus, dyspnea, nausea and vomiting, cyanosis, proteinuria and hematuria, jaundice, restlessness, and convulsion. Methemoglobinemia has been reported. (USCG, 1999)

Call a physician. EYES: Flush with water. SKIN: Wash with soap and water immediately. INGESTION: Remove by gastric lavage or emesis (vomiting) and catharsis. (USCG, 1999)


Fresh air, rest. Administration of oxygen may be needed. Refer immediately for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention .


Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

HYDROXYLAMINE & ITS SALTS ARE CORROSIVE TO SKIN & HIGHLY IRRITANT TO EYES & MUCOUS MEMBRANES. REPEATED EXPOSURE MAY ENHANCE ALLERGIC REACTION PARTICULARLY OF...HANDS & FOREARMS FROM 1-2 WK TO 2-5 YEARS AFTER COMMENCEMENT OF EXPOSURE & CASES OF ECZEMA...OBSERVED FOLLOWING PROLONGED CONTACT.|CORROSIVE TO SKIN. ... MAY CAUSE METHEMOGLOBINEMIA.|SOLN HAS CORROSIVE ACTION ON SKIN. /HYDROXYLAMINE SULFATE/|...IN WORKERS. ...INCREASES OF METHEMOGLOBIN CONTENT OF BLOOD BY UP TO 25% HAVE BEEN REPORTED AT THE END OF THE WORKING DAY.|For more Human Toxicity Excerpts (Complete) data for HYDROXYLAMINE (6 total), please visit the HSDB record page.

Hydroxylamine

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Cough. Sore throat. Dizziness. Headache. Blue lips, fingernails and skin. Shortness of breath. Weakness.


MAY BE ABSORBED! Redness. Pain. Further see Inhalation.


Redness. Pain. Severe burns.

Hydroxylamine Use and Manufacturing

Methods of Manufacturing

Add sodium ethoxide with hydroxylamine hydrochloride ethanol solution, quickly filter out the precipitated sodium hydroxide, and cool the filtrate to -18°C to crystallize and filter to obtain hydroxylamine. Hydroxylamine phosphate is heated and distilled (operated at 1.73kPa) to collect the 135-137°C distillate to obtain crude hydroxylamine.

Uses

Used as a reducing agent in organic synthesis.


Solvents (which become part of product formulation or mixture)


Metal products not covered elsewhere

All other chemical product and preparation manufacturing|Hydroxylamine: ACTIVE|World production capacity of hydroxylamine is 800,000 tons annually.

GC WITH ELECTRON DETECTION WAS USED FOR DETERMINATION OF HYDROXYLAMINE IN SEAWATER.|PULSE POLAROGRAPHY WAS USED FOR THE DETERMINATION OF HYDROXYLAMINE IN MODEL SOLUTIONS.

Food Additives -> FLOUR_TREATMENT_AGENT; -> JECFA Functional Classes|Fire Hazards -> Reactive - 3rd degree

Food Additives -> FLOUR_TREATMENT_AGENT;

Computed Properties

Molecular Weight:33.030
XLogP3:-1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:33.021463719
Monoisotopic Mass:33.021463719
Topological Polar Surface Area:46.2
Heavy Atom Count:2
Complexity:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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