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Except where otherwise noted, data are given for materials in their (at 25 °C 77 °F, 100 kPa). N ( Y N?) Hydrazine is an with the N 2H 4 (also written H 2NNH 2), archaically called diamidogen. A simple, it is a colorless flammable liquid with an -like odour. Hydrazine is highly toxic and dangerously unstable unless handled in solution. As of 2000, approximately 120,000 tons of hydrazine hydrate (corresponding to a 64% solution of hydrazine in water by weight) were manufactured worldwide per year. Hydrazine is mainly used as a in preparing, but significant applications also include its uses as a to catalysts and.

Additionally, hydrazine is used in various and to prepare the gas precursors used in. Hydrazine is used within both nuclear and conventional electrical steam cycles as an oxygen scavenger to control concentrations of dissolved oxygen in an effort to reduce corrosion. Hydrazines refer to a class of organic substances derived by replacing one or more hydrogen atoms in hydrazine by an organic group. Synthesized using hydrazine, is an medication. Hydrazine is a precursor to several pharmaceuticals and pesticides.

Often these applications involve conversion of hydrazine to such as and. Examples of commercialized bioactive hydrazine derivatives include, and. Reactivity Acid-base behavior Hydrazine forms a that is more dense (1.032 g/cm 3) than the material. Hydrazine has chemical properties comparable to those of.

It is difficult to diprotonate: N 2H 5 + + H 2O → N 2H 6 2+ + OH − K b = 8.4 x 10 −16 with the values: K b = 1.3 x 10 −6 pK a = 8.1 (for ammonia K b = 1.78 x 10 −5) Redox reactions The heat of combustion of hydrazine in oxygen (air) is 1.941 x 10 7 J/kg (8345 BTU/lb). Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. Thus, it is used as an, an oxygen, and a in water boilers and heating systems. It is also used to reduce metal salts and oxides to the pure metals in plating and extraction from. Some colour photographic processes also use a weak solution of hydrazine as a stabilizing wash, as it scavenges and unreacted silver halides. Hydrazine is the most common and effective reducing agent used to convert graphene oxide (GO) to reduced graphene oxide (rGO) via hydrothermal treatment.

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Hydrazinium salts Hydrazine can be mono to form various solid salts of the cation (N 2H 5 +) by treatment with mineral acids. A common salt is, N 2H 5HSO 4, also called hydrazine sulfate. Hydrazine sulfate was investigated as a treatment of cancer-induced, but proved ineffective. Double protonation gives the azaniumylazanium (hydrazinediium) (H 3NNH 3 2+), of which various salts are known. Organic chemistry Hydrazines are part of many, often those of practical significance in (see applications section), as well as in textile and in photography.

Hydrazone formation Illustrative of the condensation of hydrazine with a simple carbonyl is its reaction with propanone to give the diisopropylidene hydrazine (acetone azine). The latter reacts further with hydrazine to yield the hydrazone: 2 (CH 3) 2CO + N 2H 4 → 2 H 2O + (CH 3) 2C=N 2 (CH 3) 2C=N 2 + N 2H 4 → 2 (CH 3) 2C=NNH 2 The propanone azine is an intermediate in the Atofina.

Direct of hydrazines with in the presence of base yields alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on level of substitution (same as in ordinary ). The reduction of to hydrazines present a clean way to produce 1,1-dialkylated hydrazines. In a related reaction, 2-cyanopyridines react with hydrazine to form amide hydrazides, which can be converted using into. Wolff-Kishner reduction Hydrazine is used in the, a reaction that transforms the group of a into a (or an into a ) via a intermediate. The production of the highly stable from the hydrazine derivative helps to drive the reaction.

Heterocyclic chemistry Being bifunctional, with two amines, hydrazine is a key building block for the preparation of many heterocyclic compounds via condensation with a range of difunctional. With, it condenses to give the.

In the hydrazines react with imides to give. Sulfonation Being a good nucleophile, N 2H 4 can attack sulfonyl halides and acyl halides. The also forms hydrazones upon treatment with carbonyls. Deprotection of phthalimides Hydrazine is used to cleave N-alkylated phthalimide derivatives. This scission reaction allows phthalimide anion to be used as amine precursor in the. Biochemistry Hydrazine is the intermediate in the anaerobic oxidation of ammonia process.

It is produced by some yeasts and the open ocean bacterium anammox ( ). The produces the poison which is an organic derivative of hydrazine that is converted to by metabolic processes. Even the most popular edible 'button' mushroom produces organic hydrazine derivatives, including, a hydrazine derivative of an amino acid, and. Hazards Hydrazine is highly toxic and dangerously unstable in the form. According to the: Symptoms of acute (short-term) exposure to high levels of hydrazine may include irritation of the eyes, nose, and throat, dizziness, headache, nausea, in humans. Acute exposure can also damage the, and.

The liquid is and may produce from skin contact in humans and animals. Effects to the, liver, and have been reported in animals chronically exposed to hydrazine via inhalation. Increased incidences of lung, nasal cavity, and liver tumors have been observed in rodents exposed to hydrazine.

'Few cases of pure hydrazine exposure have been reported in the medical literature.' The usual antidote is or the related. Limit tests for hydrazine in pharmaceuticals suggest that it should be in the low ppm range. At least one human is known to have died after 6 months of sublethal exposure to hydrazine hydrate. Has prepared a Skin Notation Profile evaluating and summarizing the literature regarding the hazard potential of hydrazine, and has developed criteria for a recommended standard for. History The name 'hydrazine' was coined by in 1875; he was trying to produce organic compounds that consisted of mono-substituted hydrazine.

By 1887, had produced hydrazine sulfate by treating organic diazides with dilute sulfuric acid; however, he was unable to obtain pure hydrazine, despite repeated efforts. Pure anhydrous hydrazine was first prepared by the Dutch chemist in 1895. Small-scale, niche, and research Rocket fuel.

Anhydrous hydrazine being loaded into the space probe. The technician is wearing a safety suit.

Hydrazine was first used as a component in during. A 30% mix by weight with 57% (named in the German ) and 13% water was called by the Germans.

The mixture was used to power the rocket-powered fighter plane. Hydrazine was also used as a propellant with the German oxidizer. Unmixed hydrazine was referred to as by the Germans, a designation also used later for the ethanol/water fuel for the. Hydrazine is used as a low-power for the maneuvering thrusters of spacecraft, and was used to power the 's auxiliary power units (APUs). In addition, monopropellant hydrazine-fueled rocket engines are often used in terminal descent of spacecraft. Such engines were used on the landers in the 1970s as well as the lander and which landed on Mars in May 2008 and August 2012, respectively.