Hydrazine is an inorganic compound with the chemical formula N
4 (also written H
2), called diamidogen, archaically. It is a simple pnictogen hydride, and is a colorless and flammable liquid with an ammonia-like odour.
Hydrazine is highly toxic and dangerously unstable unless handled in solution as e.g., hydrazine hydrate (NH
2 · xH
2O). As of 2015, the world hydrazine hydrate market amounted to $350 million. Hydrazine is mainly used as a foaming agent in preparing polymer foams, but significant applications also include its uses as a precursor to polymerization catalysts, pharmaceuticals, and agrochemicals.
About two million tons of hydrazine hydrate were used in foam blowing agents in 2015. Additionally, hydrazine is used in various rocket fuels and to prepare the gas precursors used in air bags. Hydrazine is used within both nuclear and conventional electrical power plant 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.
|Systematic IUPAC name
3D model (JSmol)
|Molar mass||32.0452 g mol−1|
|Appearance||Colorless, fuming, oily liquid|
|Density||1.021 g cm−3|
|Melting point||2 °C; 35 °F; 275 K|
|Boiling point||114 °C; 237 °F; 387 K|
|Vapor pressure||1 kP (at 30.7 °C)|
|Acidity (pKa)||8.10 (N2H5+)|
Refractive index (nD)
|1.46044 (at 22 °C)|
|Triangular pyramidal at N|
|121.52 J K−1 mol−1|
Std enthalpy of
|50.63 kJ mol−1|
|Safety data sheet||ICSC 0281|
|GHS signal word||DANGER|
|H226, H301, H311, H314, H317, H331, H350, H410|
|P201, P261, P273, P280, P301+310, P305+351+338|
|Flash point||52 °C (126 °F; 325 K)|
|24 to 270 °C (75 to 518 °F; 297 to 543 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|59–60 mg/kg (oral in rats, mice)|
LC50 (median concentration)
|260 ppm (rat, 4 hr)|
630 ppm (rat, 1 hr)
570 ppm (rat, 4 hr)
252 ppm (mouse, 4 hr)
|US health exposure limits (NIOSH):|
|TWA 1 ppm (1.3 mg/m3) [skin]|
|Ca C 0.03 ppm (0.04 mg/m3) [2-hour]|
IDLH (Immediate danger)
|Ca [50 ppm]|
Related Binary azanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Each H2N−N subunit is pyramidal. The N−N single bond distance is 1.45 Å (145 pm), and the molecule adopts a gauche conformation. The rotational barrier is twice that of ethane. These structural properties resemble those of gaseous hydrogen peroxide, which adopts a "skewed" anticlinal conformation, and also experiences a strong rotational barrier.
Diverse routes have been developed. The key step is the creation of the nitrogen–nitrogen single bond. The many routes can be divided into those that use chlorine oxidants (and generate salt) and those that do not.
Hydrazine can be synthesized from ammonia and hydrogen peroxide in the Peroxide process (sometimes called Pechiney-Ugine-Kuhlmann process, the Atofina–PCUK cycle, or ketazine process). The net reaction follows:
In this route, the ketone and ammonia first condense to give the imine, which is oxidised by hydrogen peroxide to the oxaziridine, a three-membered ring containing carbon, oxygen, and nitrogen. Next, the oxaziridine gives the hydrazone by treatment with ammonia, which process creates the nitrogen-nitrogen single bond. This hydrazone condenses with one more equivalent of ketone.
Unlike most other processes, this approach does not produce a salt as a by-product.
Hydrazine is produced in the Olin-Raschig process from sodium hypochlorite (the active ingredient in many bleaches) and ammonia, a process announced in 1907. This method relies on the reaction of chloramine with ammonia to create the nitrogen–nitrogen single bond as well as a hydrogen chloride byproduct:
The process generates significant byproducts and is mainly practised in Asia.
The Bayer Ketazine Process is the predecessor to the peroxide process. It employs sodium hypochlorite as oxidant instead of hydrogen peroxide. Like all hypochlorite-based routes, this method produces an equivalent of salt for each equivalent of hydrazine.
Hydrazine forms a monohydrate that is more dense (1.032 g/cm3) than the anhydrous material. Hydrazine has basic (alkali) chemical properties comparable to those of ammonia. It is difficult to diprotonate:
with the values:
(for ammonia )
The heat of combustion of hydrazine in oxygen (air) is 1.941 × 107 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 antioxidant, an oxygen scavenger, and a corrosion inhibitor in water boilers and heating systems. It is also used to reduce metal salts and oxides to the pure metals in electroless nickel plating and plutonium extraction from nuclear reactor waste. Some colour photographic processes also use a weak solution of hydrazine as a stabilizing wash, as it scavenges dye coupler 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.
Hydrazine can be monoprotonated to form various solid salts of the hydrazinium cation (N2H5+) by treatment with mineral acids. A common salt is hydrazinium sulfate, [N2H5]HSO4, also called hydrazine sulfate. Hydrazine sulfate was investigated as a treatment of cancer-induced cachexia, but proved ineffective.
Hydrazine is used in the Wolff-Kishner reduction, a reaction that transforms the carbonyl group of a ketone into a methylene bridge (or an aldehyde into a methyl group) via a hydrazone intermediate. The production of the highly stable dinitrogen from the hydrazine derivative helps to drive the reaction.
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 electrophiles. With 2,4-pentanedione, it condenses to give the 3,5-dimethylpyrazole. In the Einhorn-Brunner reaction hydrazines react with imides to give triazoles.
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:
The propanone azine is an intermediate in the Atofina-PCUK process. Direct alkylation of hydrazines with alkyl halides 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 amines). The reduction of hydrazones to hydrazines present a clean way to produce 1,1-dialkylated hydrazines.
Hydrazine is the intermediate in the anaerobic oxidation of ammonia (anammox) process. It is produced by some yeasts and the open ocean bacterium anammox (Brocadia anammoxidans). The false morel produces the poison gyromitrin which is an organic derivative of hydrazine that is converted to monomethylhydrazine by metabolic processes. Even the most popular edible "button" mushroom Agaricus bisporus produces organic hydrazine derivatives, including agaritine, a hydrazine derivative of an amino acid, and gyromitrin.
The majority use of hydrazine is as a precursor to blowing agents. Specific compounds include azodicarbonamide and azobisisobutyronitrile, which yield 100–200 mL of gas per gram of precursor. In a related application, sodium azide, the gas-forming agent in air bags, is produced from hydrazine by reaction with sodium nitrite.
Hydrazine is also used as a propellant onboard space vehicles, such as the NASA Dawn probe to Ceres and Vesta, and to both reduce the concentration of dissolved oxygen in and control pH of water used in large industrial boilers. The F-16 fighter jet, NASA Space Shuttle, and U-2 Spy Plane use hydrazine to fuel their emergency power units.
Hydrazine is a precursor to several pharmaceuticals and pesticides. Often these applications involve conversion of hydrazine to heterocyclic rings such as pyrazoles and pyridazines. Examples of commercialized bioactive hydrazine derivatives include cefazolin, rizatriptan, anastrozole, fluconazole, metazachlor, metamitron, metribuzin, paclobutrazol, diclobutrazole, propiconazole, hydrazine sulfate, diimide, triadimefon, and dibenzoylhydrazine.
Hydrazine compounds can be effective as active ingredients in admixture with or in combination with other agricultural chemicals such as insecticides, miticides, nematicides, fungicides, antiviral agents, attractants, herbicides or plant growth regulators.
The Italian catalyst manufacturer Acta (chemical company) has proposed using hydrazine as an alternative to hydrogen in fuel cells. The chief benefit of using hydrazine is that it can produce over 200 mW/cm2 more than a similar hydrogen cell without the need to use expensive platinum catalysts. As the fuel is liquid at room temperature, it can be handled and stored more easily than hydrogen. By storing the hydrazine in a tank full of a double-bonded carbon-oxygen carbonyl, the fuel reacts and forms a safe solid called hydrazone. By then flushing the tank with warm water, the liquid hydrazine hydrate is released. Hydrazine has a higher electromotive force of 1.56 V compared to 1.23 V for hydrogen. Hydrazine breaks down in the cell to form nitrogen and hydrogen which bonds with oxygen, releasing water. Hydrazine was used in fuel cells manufactured by Allis-Chalmers Corp., including some that provided electric power in space satellites in the 1960s.
A mixture of 63% hydrazine, 32% hydrazine nitrate and 5% water is a standard propellant for experimental bulk-loaded liquid propellant artillery. The propellant mixture above is one of the most predictable and stable, with a flat pressure profile during firing. Misfires are usually caused by inadequate ignition. The movement of the shell after a misignition causes a large bubble with a larger ignition surface area, and the greater rate of gas production causes very high pressure, sometimes including catastrophic tube failures (i.e. explosions). From January–June 1991, the U.S. Army Research Laboratory conducted a review of early bulk-loaded liquid propellant gun programs for possible relevance to the electrothermal chemical propulsion program.
The United States Air Force (USAF) regularly uses H-70, a 70% hydrazine 30% water mixture, in operations employing the General Dynamics F-16 “Fighting Falcon” fighter aircraft and the Lockheed U-2 “Dragon Lady” reconnaissance aircraft. The single jet engine F-16 utilizes hydrazine to power its Emergency Power Unit (EPU), which provides emergency electrical and hydraulic power in the event of an engine flame out. The EPU activates automatically, or manually by pilot control, in the event of loss of hydraulic pressure or electrical power in order to provide emergency flight controls. The single jet engine U-2 utilizes hydrazine to power its Emergency Starting System (ESS), which provides a highly reliable method to restart the engine in flight in the event of a stall.
Hydrazine was first used as a component in rocket fuels during World War II. A 30% mix by weight with 57% methanol (named M-Stoff in the German Luftwaffe) and 13% water was called C-Stoff by the Germans. The mixture was used to power the Messerschmitt Me 163B rocket-powered fighter plane. Hydrazine was also used as a propellant with the German high test peroxide T-Stoff oxidizer. Unmixed hydrazine was referred to as B-Stoff by the Germans, a designation also used later for the ethanol/water fuel for the V-2 missile.
Hydrazine is used as a low-power monopropellant for the maneuvering thrusters of spacecraft, and was used to power the Space Shuttle'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 Viking program landers in the 1970s as well as the Phoenix lander and Curiosity rover which landed on Mars in May 2008 and August 2012, respectively.
In all hydrazine monopropellant engines, the hydrazine is passed by a catalyst such as iridium metal supported by high-surface-area alumina (aluminium oxide), which causes it to decompose into ammonia, nitrogen gas, and hydrogen gas according to the following reactions:
Reactions 1 and 2 are extremely exothermic (the catalyst chamber can reach 800 °C in a matter of milliseconds,) and they produce large volumes of hot gas from a small volume of liquid, making hydrazine a fairly efficient thruster propellant with a vacuum specific impulse of about 220 seconds. Reaction 3 is endothermic and so reduces the temperature of the products, but also produces a greater number of molecules. The catalyst structure affects the proportion of the NH3 that is dissociated in Reaction 3; a higher temperature is desirable for rocket thrusters, while more molecules are desirable when the reactions are intended to produce greater quantities of gas.
Other variants of hydrazine that are used as rocket fuel are monomethylhydrazine, (CH3)NH(NH2) (also known as MMH), and unsymmetrical dimethylhydrazine, (CH3)2N(NH2) (also known as UDMH). These derivatives are used in two-component rocket fuels, often together with dinitrogen tetroxide, N2O4. These reactions are extremely exothermic, and the burning is also hypergolic (it starts burning without any external ignition).
There are ongoing efforts in the aerospace industry to replace hydrazine and other highly toxic substances. Promising alternatives include hydroxylammonium nitrate, 2-dimethylaminoethylazide (DMAZ) and energetic ionic liquids.
Potential routes of hydrazine exposure include dermal, ocular, inhalation and ingestion.
Hydrazine exposure can cause skin irritation/contact dermatitis and burning, irritation to the eyes/nose/throat, nausea/vomiting, shortness of breath, pulmonary edema, headache, dizziness, central nervous system depression, lethargy, temporary blindness, seizures and coma. Exposure can also cause organ damage to the liver, kidneys and central nervous system. Hydrazine is documented as a strong skin sensitizer with potential for cross-sensitization to hydrazine derivatives following initial exposure. In addition to occupational uses reviewed above, exposure to hydrazine is also possible in small amounts from tobacco smoke.
The official U.S. guidance on hydrazine as a carcinogen is mixed but generally there is recognition of potential cancer-causing effects. The National Institute for Occupational Safety and Health (NIOSH) lists it as a “potential occupational carcinogen”. The National Toxicology Program (NTP) finds it is "reasonably anticipated to be a human carcinogen". The American Conference of Governmental Industrial Hygienists (ACGIH) grades hydrazine as "A3—confirmed animal carcinogen with unknown relevance to humans". The U.S. Environmental Protection Agency (EPA) grades it as "B2—a probable human carcinogen based on animal study evidence".
The International Agency for Research on Cancer (IARC) rates hydrazine as "2A—probably carcinogenic to humans" with a positive association observed between hydrazine exposure and lung cancer. Based on cohort and cross-sectional studies of occupational hydrazine exposure, a committee from the National Academies of Sciences, Engineering and Medicine concluded that there is suggestive evidence of an association between hydrazine exposure and lung cancer, with insufficient evidence of association with cancer at other sites. The European Commission’s Scientific Committee on Occupational Exposure Limits (SCOEL) places hydrazine in carcinogen “group B—a genotoxic carcinogen”. The genotoxic mechanism the committee cited references hydrazine’s reaction with endogenous formaldehyde and formation of a DNA-methylating agent.
In the event of a hydrazine exposure-related emergency, NIOSH recommends removing contaminated clothing immediately, washing skin with soap and water, and for eye exposure removing contact lenses and flushing eyes with water for at least 15 minutes. NIOSH also recommends anyone with potential hydrazine exposure to seek medical attention as soon as possible. There are no specific post-exposure laboratory or medical imaging recommendations, and the medical work-up may depend on the type and severity of symptoms. The World Health Organization (WHO) recommends potential exposures be treated symptomatically with special attention given to potential lung and liver damage. Past cases of hydrazine exposure have documented success with Pyridoxine (Vitamin B6) treatment.
The odor threshold for hydrazine is 3.7 ppm, thus if a worker is able to smell an ammonia-like odor then they are likely over the exposure limit. However, this odor threshold varies greatly and should not be used to determine potentially hazardous exposures.
For aerospace personnel, the USAF uses an emergency exposure guideline, developed by the National Academy of Science Committee on Toxicology, which is utilized for non-routine exposures of the general public and is called the Short-Term Public Emergency Exposure Guideline (SPEGL). The SPEGL, which does not apply to occupational exposures, is defined as the acceptable peak concentration for unpredicted, single, short-term emergency exposures of the general public and represents rare exposures in a worker’s lifetime. For hydrazine the 1-hour SPEGL is 2 ppm, with a 24-hour SPEGL of 0.08 ppm.
A complete surveillance program for hydrazine should include systematic analysis of biologic monitoring, medical screening and morbidity/mortality information. The CDC recommends surveillance summaries and education be provided for supervisors and workers. Pre-placement and periodic medical screening should be conducted with specific focus on potential effects of hydrazine upon functioning of the eyes, skin, liver, kidneys, hematopoietic, nervous and respiratory systems.
Common controls used for hydrazine include process enclosure, local exhaust ventilation and personal protective equipment (PPE). Guidelines for hydrazine PPE include non-permeable gloves and clothing, indirect-vent splash resistant goggles, face shield and in some cases a respirator. The use of respirators for the handling of hydrazine should be the last resort as a method of controlling worker exposure. In cases where respirators are needed, proper respirator selection and a complete respiratory protection program consistent with OSHA guidelines should be implemented.
For USAF personnel, Air Force Occupational Safety and Health (AFOSH) Standard 48-8, Attachment 8 reviews the considerations for occupational exposure to hydrazine in missile, aircraft and spacecraft systems. Specific guidance for exposure response includes mandatory emergency shower and eyewash stations and a process for decontaminating protective clothing. The guidance also assigns responsibilities and requirements for proper PPE, employee training, medical surveillance and emergency response. USAF bases requiring the use of hydrazine generally have specific base regulations governing local requirements for safe hydrazine use and emergency response.
The name "hydrazine" was coined by Emil Fischer in 1875; he was trying to produce organic compounds that consisted of mono-substituted hydrazine. By 1887, Theodor Curtius had produced hydrazine sulfate by treating organic diazides with dilute sulfuric acid; however, he was unable to obtain pure hydrazine, despite repeated efforts.:27–58;107–139 Pure anhydrous hydrazine was first prepared by the Dutch chemist Lobry de Bruyn in 1895.
1,2-Dimethylhydrazine, or symmetrical dimethylhydrazine, is the organic compound with the formula (CH3NH)2. It is one of the two isomers of dimethylhydrazine. Both isomers are colorless liquids at room temperature, with properties similar to those of methylamines. 1,2-Dimethylhydrazine is a potent carcinogen that acts as a DNA methylating agent. The compound has no commercial value, in contrast to its isomer, which is used as a rocket fuel.It is used to induce colon tumors in experimental animals - particularly mice and feline cell samples.Aerozine 50
Aerozine 50 is a 50:50 mix by weight of hydrazine and unsymmetrical dimethylhydrazine (UDMH), originally developed in the late 1950s by Aerojet General Corporation as a storable, high-energy, hypergolic fuel for the Titan II ICBM rocket engines. Aerozine continues in wide use as a rocket fuel, typically with dinitrogen tetroxide as the oxidizer, with which it is hypergolic. Aerozine 50 is more stable than hydrazine alone, and has a higher density and boiling point than UDMH alone.
By cutting straight hydrazine with UDMH, hydrazine's inconveniently high freezing point of 2 °C is lowered through freezing point depression. In addition, UDMH is a more stable molecule; this reduces the chances of straight hydrazine decomposing unexpectedly, increasing safety and allowing the blend to be used as a coolant in regeneratively cooled engines.
Hydrazine may also be mixed with monomethyl hydrazine (MMH). Because MMH is slightly denser, net performance is increased slightly.
This type of fuel is mainly used for interplanetary probes and spacecraft propulsion. Unlike other more common propellants like liquid oxygen or liquid hydrogen, Aerozine 50 is liquid at room temperature and can be stored in liquid state without significant boil off, thus making it a storable propellant better suited for long-term interplanetary missions. Aerozine 50 was largely used in ICBMs and in their derivative launchers such as the core stages of the Titan-II/III/IV rocket because an ICBM requires long term storage and launch on short notice; the rocket must be stored already fueled. This fuel was also used in ICBM derived upper stages, such as the Delta II rocket. It was also used by the Apollo Lunar Module and the Service Propulsion System engine in the Apollo CSM. The Ariane 1 through Ariane 4 family used a related fuel, a mixture of 75% UDMH and
25% hydrazine hydrate called UH 25.
Aerozine is not used as a monopropellant. The extra stability conferred by the methyl groups affects reactivity and thrust.
In 1980, a leakage of Aerozine 50 resulted in the 1980 Damascus Titan missile explosion. The leak occurred due to puncture of the first-stage Titan fuel tank by a dropped tool. The initial explosion removed the 740-ton silo door and ejected the second stage and warhead out of the silo. The Titan's second stage exploded and the W53 warhead landed 30 meters from the silo portal without detonating or leaking fissile material.Atlas I
The Atlas I was an American expendable launch system, used in the 1990s to launch a variety of different satellites. The "I" in "Atlas I" can cause confusion, as all previous Atlas rockets were designated using letters, ending with the Atlas H, however subsequent rockets were designated using Roman numerals, starting with the Atlas II. Officially, the "I" is the Roman numeral "1". Eleven launches took place, with three failures.
Though the Atlas I was marketed as a new rocket, it was more just a re-brand of the Atlas G/H for commercial payloads, while the Atlas G and H were mostly private.
Atlas I was the last use of the classic Atlas design with three engines, jettisonable booster section, and two vernier engines, as Atlas II, while retaining most of those features, replaced the verniers with a hydrazine roll control system.Benmoxin
Benmoxin (trade names Neuralex, Nerusil), also known as mebamoxine, is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine class. It was synthesized in 1967 and was subsequently used as an antidepressant in Europe, but is now no longer marketed.Green Propellant Infusion Mission
The Green Propellant Infusion Mission (GPIM) is a planned NASA technology demonstrator project that will test a less toxic and higher performance/efficiency chemical propellant for next-generation launch vehicles and spacecraft. When compared to the present high-thrust and high-performance industry standard for orbital maneuvering systems, which for decades, have exclusively been reliant upon toxic hydrazine based propellant formulations, the "greener" hydroxylammonium nitrate(HAN) monopropellant may offer many advantages for future satellites, including longer mission durations, additional maneuverability, increased payload space and simplified launch processing.
The GPIM is managed by NASA's Marshall Space Flight Center in Huntsville, Alabama, and is part of NASA's Technology Demonstration Mission Program within the Space Technology Mission Directorate.
The Green Propellant Infusion Mission is scheduled to launch aboard a SpaceX Falcon Heavy rocket in 2019, on a test mission called Space Test Program 2 (STP-2). The cost of the program is projected to be approximately $45 million.Hydrazine (antidepressant)
The hydrazine antidepressants are a group of non-selective, irreversible monoamine oxidase inhibitors (MAOIs) which were discovered and initially marketed in the 1950s and 1960s. Most have been withdrawn due to toxicity, namely hepatotoxicity, but a few still remain in clinical use.
Tranylcypromine, a structurally unrelated MAOI introduced around the same time as the hydrazines, was originally advertised as non-hydrazine as a result of its diminished propensity for causing hepatotoxicity.Hydrazine sulfate
Hydrazine sulfate, more properly hydrazonium hydrogensulfate, is a salt of the cation hydrazinium and the anion bisulfate (hydrogensulfate), with the formula [N2H+5] [HSO−4] or N2H6SO4. It is a white, water-soluble solid at room temperature.
Hydrazine sulfate has a number of uses in chemical laboratories and in the chemical industry, including analytical chemistry and the synthesis of organic compounds. In those uses it is usually preferred to pure hydrazine, because it is not volatile and is less susceptible to atmospheric oxidation on storage.
Hydrazine sulfate has been also advanced in the past as an alternative medical treatment, under the trade name Sehydrin.Hypergolic propellant
A hypergolic propellant combination used in a rocket engine is one whose components spontaneously ignite when they come into contact with each other.
The two propellant components usually consist of a fuel and an oxidizer. The main advantages of hypergolic propellants are that they can be stored as liquids at room temperature and that engines which are powered by them are easy to ignite reliably and repeatedly. Although commonly used, hypergolic propellants are difficult to handle due to their extreme toxicity and/or corrosiveness.
In contemporary usage, the terms "hypergol" or "hypergolic propellant" usually mean the most common such propellant combination, dinitrogen tetroxide plus hydrazine and/or its relatives monomethylhydrazine and unsymmetrical dimethylhydrazine.Iproniazid
Iproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until fairly recently.Monomethylhydrazine
Monomethylhydrazine (MMH) is a volatile hydrazine chemical with the chemical formula CH3(NH)NH2. It is used as a rocket propellant in bipropellant rocket engines because it is hypergolic with various oxidizers such as nitrogen tetroxide (N2O4) and nitric acid (HNO3). As a propellant, it is described in specification MIL-PRF-27404.MMH is a hydrazine derivative that was once used in the orbital maneuvering system (OMS) and reaction control system (RCS) engines of NASA's Space Shuttle, which used MMH and MON-3 (a mixture of nitrogen tetroxide with approximately 3% nitric oxide). This chemical is toxic and carcinogenic in small amounts, but it is easily stored in orbit providing moderate performance for very low fuel tank system weight. Recently the European Space Agency (ESA) has attempted to seek new options in terms of bipropellant rocket combinations to avoid poisonous chemicals such as this and its relatives.MMH and its chemical relative unsymmetrical dimethylhydrazine (UDMH) have a key advantage that they are stable enough to be used in regeneratively cooled rocket engines. The Apollo Lunar Modules used a one-to-one mixture of hydrazine and UDMH (called Aerozine 50, or A-50) as one part of the rocket fuel for lunar landings and takeoff: the rocket motors formed a hypergolic mixture of the hydrazines with liquid dinitrogen tetroxide as the usual oxidizer. (Otherwise, red fuming nitric acid works.) About three tons of mixed hydrazines and four and one half tons of the oxidizer were required for each landing, and about one-third of those amounts for the lunar take-off to orbit.Monomethylhydrazine is believed to be the main cause of the toxicity of mushrooms of genus Gyromitra, especially the false morel (Gyromitra esculenta). In these cases, MMH is formed by the hydrolysis of gyromitrin.Monomethylhydrazine is considered to be a possible occupational carcinogen, and the occupational exposure limits to MMH are set at protective levels to account for the possible carcinogenicity.A known use of MMH is in the synthesis of Suritozole.Octamoxin
Octamoxin (trade names Ximaol, Nimaol), also known as 2-octylhydrazine, is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant in the 1960s but is now no longer marketed.Pheniprazine
Pheniprazine (INN; also known as amphethydrazine and amphetamine hydrazide; brand names Catron and Cavodil) is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class that was used as an antidepressant in the 1960s. It was also used in the treatment of angina pectoris and schizophrenia. Pheniprazine has been largely discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis.Phenoxypropazine
Phenoxypropazine (trade name Drazine) is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine family. It was introduced as an antidepressant in 1961, but was subsequently withdrawn in 1966 due to hepatotoxicity concerns.Phenylhydrazine
Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. It is often abbreviated as PhNHNH2.Pivhydrazine
Pivhydrazine (trade name Tersavid), also known as pivalylbenzhydrazine and pivazide, is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine family. It was formerly used as an antidepressant in the 1960s, but has since been discontinued.Safrazine
Safrazine (Safra) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was introduced as an antidepressant in the 1960s, but has since been discontinued.Triazane
Triazane (also systematically named 1,1,2,3,3-pentahydrido-1,2,3-triazy-catena), or aminohydrazine is an inorganic compound with the chemical formula NH2NHNH2 (also written [H2NN(H)NH2] or [N3H5]). Triazane is the third simplest acyclic azane (the simplest are ammonia and hydrazine). It can be synthesised from hydrazine but is unstable and cannot be isolated in the free base form, only as salt forms such as triazanium sulfate. Attempts to convert triazanium salts to the free base release only diazene and ammonia.
Triazane was first synthesised as a ligand of the silver complex ion: tris(μ2-triazane-κ2N1,N3)disilver(2+).UH 25
UH 25 is a fuel mixture for rockets. It was developed for the European Ariane 2–4 launch vehicles.
UH 25 was developed after a disaster during flight 2 of the Ariane 1 rocket. During launch, one of the four Viking engines on the first stage developed a combustion instability which led to an engine fire, subsequent explosion and destruction of the vehicle. Following this event and starting with Ariane 2, the fuel was changed from pure UDMH to the mixture UH 25.UH 25 was used in Ariane rocket versions 2 through 4, and in the Indian GSLV Mk III
UH 25 is a mixture of 75% UDMH and 25% hydrazine hydrate. It is hypergolic with dinitrogen tetroxide as oxidizer, and both can be stored as liquids at room temperature.Unsymmetrical dimethylhydrazine
Unsymmetrical dimethylhydrazine (UDMH; 1,1-dimethylhydrazine) is a chemical compound with the formula H2NN(CH3)2. It is a colorless liquid, with a sharp, fishy, ammoniacal smell typical for organic amines. Samples turn yellowish on exposure to air and absorb oxygen and carbon dioxide. It mixes completely with water, ethanol, and kerosene. In concentration between 2.5% and 95% in air, its vapors are flammable. It is not sensitive to shock. 1,2-Dimethylhydrazine (CH3NHNHCH3) is also known but is not as useful.
|Alkali metal hydrides|
Lithium hydride, LiH
ionic metal hydride
Left (gas phase): BeH2
covalent metal hydride
Right: (BeH2)n (solid phase)
polymeric metal hydride
Borane and diborane
Left: BH3 (special conditions), covalent metalloid hydride
Right: B2H6 (standard conditions), dimeric metalloid hydride
covalent nonmetal hydride
covalent nonmetal hydride
covalent nonmetal hydride
Hydrogen fluoride, HF
covalent nonmetal hydride
|Alkaline earth hydrides|
|Group 13 hydrides|
|Group 14 hydrides|
|Transition metal hydrides|