Hydrazine - Wikipedia, The Free Encyclopedia

7/23/2019 Hydrazine - Wikipedia, The Free Encyclopedia

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Hydrazine

Hydrazine hydrate

Names

Systematic IUPAC name

Hydrazine[2]

Other names

Diamine[1]

Diazane[2]

Identifiers

CAS RegistryNumber

302-01-2

3DMet B00770

BeilsteinReference

878137

HydrazineFrom Wikipedia, the free encyclopedia

Hydrazine(systematically nameddiazaneortetrahydridodinitrogen(NN)) isan inorganic compound with the

chemical formula H2NNH2(also

written N2H4). It is a colourlessflammable liquid with an ammonia-like odor. Hydrazine is highly toxicand dangerously unstable unlesshandled in solution. As of 2000,approximately 120,000 tons ofhydrazine hydrate (correspondingto a 64% solution of hydrazine in

water by weight) weremanufactured worldwide per

ear.[8]Hydrazine is mainlyused asa foaming agent in preparing

polymer foams, but significantapplications also include its uses asa precursor to polymerizationcatalysts and pharmaceuticals.Additionally, hydrazine is used invarious rocket fuels and to preparethe gas precursors used in air bags.Hydrazine is used within bothnuclear and conventionalelectrical

power plant steam cycles as anoxygen scavenger to controlconcentrations of dissolved oxygenin an effort to reduce corrosion.

Contents1 Molecular structure and

properties2 Synthesis and production

2.1 Oxidation bychloroamine fromhypochlorite onammonia2.2 Oxidation of urea
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ChEBI CHEBI:15571

ChEMBL ChEMBL1237174

ChemSpider 8960

EC number 206-114-9

Gmelin Reference 190

Jmol-3D images Image (http://chemapps.stolaf.edu/jmol/jmol.php?

model=NN)

KEGG C05361

MeSH Hydrazine

PubChem 9321

RTECS number MU7175000

UNII27RFH0GB4R

UN number 2029

Properties

Chemical formula N2H4

Molar mass 32.0452 g mol1

Appearance Colourless, fuming, oily liquid[3]

Odor ammonia-like[3]

Density 1.021 g cm3

Melting point 2 C 35 F 275 K

Boiling point 114 C 237 F 387 K

Solubility in watermiscible[3]

log P 0.67

Vapor pressure 1 kP (at 30.7 C)

Acidity (pKa) 8.10[4]

Basicity (pKb) 5.90

Refractive index(nD)

1.46044 (at 22 C)

Viscosity 0.876 cP

Structure

Molecular shape Triangular pyramidal at N

Dipole moment 1.85 D[5]

Thermochemistry

Std molar 121.52 J K1mol1

by hypochlorite2.3 Oxidation bychloroamine fromhypochlorite onammonia in presenceof acetone2.4 Oxidation byoxaziridine from

peroxide onammonia3 Applications

3.1 Precursor topesticides andpharmaceuticals

4 Hydrazine in biology5 Organic chemistry

5.1 Hydrazoneformation5.2 Wolff-Kishner

reduction5.3 Heterocyclicchemistry5.4 Sulfonation5.5 Deprotection of

phthalimides5.6 Reducing agent5.7 Hydraziniumsalts

6 Other industrial uses

6.1 Rocket fuel6.2 Fuel cells6.3 Gun propellant

7 Hazards8 History9 See also10 References11 External links

Molecular structureand properties

Hydrazine forms a monohydrate

that is denser (1.032 g/cm3) thanthe anhydrous material.

Hydrazine can arise via coupling apair of ammonia molecules byremoval of one hydrogen per

InChI

SMILES
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entropy (So298)

Std enthalpy offormation

(fHo

298)

50.63 kJ mol1

Hazards

Safety data sheet ICSC 0281

(http://www.inchem.org/documents/icsc/icsc/eics0281.htm

GHS pictograms

GHS signal word DANGER

GHS hazardstatements

H226, H301, H311, H314, H317, H331, H350, H410

GHSprecautionarystatements

P201, P261, P273, P280, P301+310, P305+351+338

EU Index 007-008-00-3

EU classificationT+

N

[6]

R-phrases R45, R10, R23/24/25, R34, R43, R50/53

S-phrases S53, S45, S60, S61

NFPA 704

Flash point 52 C (126 F 325 K)

Autoignitiontemperature

24 to 270 C (75 to 518 F 297 to 543 K)

Explosive limits 1.899.99%

Lethal dose or concentration (LD,LC):

LD50 (Median

dose)

5960 mg/kg (oral in rats, mice)[7]

US health exposure limits (NIOSH):

PEL(Permissible)

TWA 1 ppm (1.3 mg/m3) [skin][3]

REL(Recommended)

Ca C 0.03 ppm (0.04 mg/m3) [2-hour][3]

IDLH(Immediatedanger

Ca [50 ppm][3]

Related compounds

Other anions tetrafluorohydrazine

hydrogen peroxide

molecule. Each H2N-N subunit is

pyramidal in shape. The N-N singlebonddistance is 1.45 (145 pm),and the molecule adopts a gauche

conformation.[9]The rotationalbarrier is twice that of ethane.These structural properties

resemble those of gaseoushydrogen peroxide, which adopts a"skewed" anticlinal conformation,and also experiences a strongrotational barrier.

Hydrazine has basic (alkali)chemical properties comparable tothose of ammonia:

N2H4+ H2O [N2H5]+

+OH

with the values:[10]

Kb= 1.3 x 106

pKa= 8.1

(for ammoniaKb= 1.78 x 105)

Hydrazine is difficult to

diprotonate:[11]

[N2H5]++ H2O [N2H6]

2+

+ OHKb= 8.4 x 1016

The heat of combustion ofhydrazine in oxygen (air) is 1.941 x

107J/kg (9345 BTU/lb).[12]

Synthesis and

production

Different routes have been

developed over the years:[8]the keystep is the creation of the nitrogen-nitrogen single bond. In the OlinRaschig process, chlorine-based

44 3
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diphosphane

diphosphorus tetraiodide

Other cations organic hydrazines

Related Binaryazanes

Ammonia

triazane

Related

compounds

diazene

triazene

tetrazene

diphosphene

Except where otherwise noted, data are given for materials in their standardstate (at 25 C [77 F], 100 kPa).

verify (what is: / ?)

Infobox references

oxidants oxidizes ammonia withoutthe presence of ketone. In the

peroxide process, hydrogenperoxide oxidizes ammonia in thepresence of ketone. Instead ofcarbon-nitrogen double bond inimine, urea provides amine groups

bonded to carbonyl for oxidation.

Oxidation by chloroamine

from hypochlorite on

ammonia

Hydrazine is produced in the OlinRaschig process from sodiumhypochlorite (the active ingredientin many bleaches) and ammonia, a

process announced in 1907. This method relies on the reaction of chloramine with ammonia to create thenitrogen-nitrogen single bond as well as a hydrogen chloride byproduct:[13]

NH2Cl + NH3 H2N-NH2+ HCl

Oxidation of urea by hypochlorite

Related to the Rasching process, urea can be oxidized instead of ammonia. Again sodium hypochlorite

serves as the oxidant. The net reaction is shown:[14]

(H2N)2C=O + NaOCl + 2 NaOH N2H4+ H2O + NaCl + Na2CO3

The process generates significant byproducts and is mainly practiced in Asia.[8]

Oxidation by chloroamine from hypochlorite on ammonia in presence of acetone

The Bayer Ketazine Process is the predecessor to the peroxide process. It employs sodium hypochlorite asoxidant instead of hydrogen peroxide. Like all hypochlorite-based routes, this method suffers from the fact

that it produces an equivalent of salt for each equivalent of hydrazine.[8]

Oxidation by oxaziridine from peroxide on ammonia

Hydrazine can be synthesized from ammonia and hydrogen peroxide in the peroxide process (sometimes

called Pechiney-Ugine-Kuhlmann process, the AtofinaPCUK cycle, or ketazine process).[8]The net

reaction follows:[15]

2 NH3+ H2O2 H2N-NH2+ 2 H2O
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In this route, hydrazine is produced in several steps from ammonia, hydrogen peroxide, and a ketone suchas acetone or methylethyl ketone. The ketone and ammonia first condense to give the imine, which isoxidised by hydrogen peroxide to the oxaziridine, a three-membered ring containing carbon, oxygen, andnitrogen. Next, the oxaziridine gives the hydrazone by treatment with ammonia, a process creating thenitrogen-nitrogen single bond. This hydrazone condenses with one more equivalent of ketone the resultingazine is hydrolyzed to give hydrazine and regenerate the ketone. Unlike the Olin Raschig Process, this

approach does not produce a salt as a by-product.[16]

Applications

The majority use of hydrazine is as a precursor to blowing agents. Specific compounds includeazodicarbonamide and azobisisobutyronitrile, which yield 100-200 mL of gas per gram of precursor. In arelated application, sodium azide, the gas-forming agent in air bags, is produced from hydrazine by reactio

with sodium nitrite.[8]

Hydrazine is also used as a propellant on board space vehicles, and to both reduce the concentration ofdissolved oxygen in and control pH of water used in large industrial boilers. The F-16 fighter jet uses

hydrazine to fuel the aircraft's emergency power unit.

Precursor to pesticides and pharmaceuticals

Hydrazine is a useful building block in organic synthesis of pharmaceuticals and pesticides. One example 3-amino-1,2,4-triazole and another is maleic hydrazide. The antitubercular drug isoniazid is prepared fromhydrazine.

Hydrazine in biology

Hydrazine is the intermediate in the anaerobic oxidation of ammonia (anammox) process.[17]It is produce

by some yeasts and the open ocean bacterium anammox (Brocadia anammoxidans).[18]The false morelproduces the poison gyromitrin which is an organic derivative of hydrazine that is converted tomonomethylhydrazine 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.[19][20]

Organic chemistry

Hydrazines are part of many organic syntheses, often those of practical significance in pharmaceuticals,such as the antituberculosis medication isoniazid and the antifungal fluconazole, as well as in textile dyes

and in photography.[8]

Hydrazone formation

Illustrative of the condensation of hydrazine with a simple carbonyl is its reaction with propanone to givethe diisopropylidene hydrazine (acetone azine). The latter reacts further with hydrazine to yield the

hydrazone:[21]
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2 (CH3)2CO + N2H4 2 H2O + [(CH3)2C=N]2[(CH3)2C=N]2+ N2H4 2 (CH3)2C=NNH2

The propanone azine is an intermediate in the Atofina-PCUK process. Direct alkylation of hydrazines withalkyl halides in the presence of base yields alkyl-substituted hydrazines, but the reaction is typicallyinefficient due to poor control on level of substitution (same as in ordinary amines). The reduction ofhydrazones 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 beconverted using 1,2-diketones into triazines.

Wolff-Kishner reduction

Hydrazine is used in the Wolff-Kishner reduction, a reaction that transforms the carbonyl group of a ketoninto a methylene bridge (or an aldehyde into a methyl group) via a hydrazone intermediate. The productionof the highly stable dinitrogen 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 manyheterocyclic compounds via condensation with a range of difunctional electrophiles. With 2,4-

pentanedione, it condenses to give the 3,5-dimethylpyrazole.[22]In the Einhorn-Brunner reaction hydrazinereact with imides to give triazoles.

Sulfonation

Being a good nucleophile, N2H4can attack sulfonyl halides and acyl halides.[23]The tosylhydrazine also

forms hydrazones upon treatment with carbonyls.

Deprotection of phthalimides

Hydrazine is used to cleaveN-alkylated phthalimide derivatives. This scission reaction allows phthalimide

anion to be used as amine precursor in the Gabriel synthesis.[24]

Reducing agent

Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. Thus, itis used as an antioxidant, an oxygen scavenger, and a corrosion inhibitor in water boilers and heatingsystems. 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 weaksolution 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.[25]

Hydrazinium salts
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Hydrazine is converted to solid salts by treatment with mineral acids. A common salt is hydrazine sulfate,

[N2H5]HSO4, called hydrazinium sulfate.[26]Hydrazine sulfate was investigated as a treatment of cancer-

induced cachexia, but proved ineffective.[27]

Hydrazine azide (N5H5), the salt of hydrazine and hydrazoic acid, was of scientific interest, because of its

high nitrogen content and explosive properties. Structurally, it is [N2H5]+

[N3]

. It decomposes explosively

into hydrazine, ammonia and nitrogen gas:[28]

12 N5H5 3 N2H4+ 16 NH3+ 19 N2

Reaction of N5H5with sulfuric acid gives quantitative yields of pure hydrazine sulfate and hydrazoic

acid.[29]

Other industrial uses

Hydrazine is used in many processes including: production of spandex fibers, as a polymerization catalystin fuel cells, solder fluxes and photographic developers, as a chain extender in urethane polymerizations,and heat stabilizers. In addition, a semiconductor deposition technique using hydrazine has recently beendemonstrated, with possible application to the manufacture of thin-film transistors used in liquid crystaldisplays. Hydrazine in a 70% hydrazine, 30% water solution is used to power the EPU (emergency powerunit) on the Lockheed F-16 Fighting Falcon fighter plane. The explosive Astrolite is made by combininghydrazine with ammonium nitrate.

Hydrazine is often used as an oxygen scavenger and corrosion inhibitor in boiler water treatment. Howevedue to the toxicity and certain undesired effects this practice is discouraged.

Rocket fuel

Hydrazine was first used as a rocket fuel during World War II for the Messerschmitt Me 163B (the firstrocket-powered fighter plane), under the code name B-Stoff(hydrazine hydrate). When mixed with

methanol (M-Stoff) and water it was called C-Stoff.[30]

Hydrazine is also used as a low-power monopropellant for the maneuvering thrusters of spacecraft, and waused 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 onMars 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) or carbon nanofibers,[31]or more recently

molybdenum nitride on alumina,[32]which causes it to decompose into ammonia, nitrogen gas, and

hydrogen gas according to the following reactions:[33]

1. 3 N2H4 4 NH3+ N2
https://en.wikipedia.org/wiki/Ammoniahttps://en.wikipedia.org/wiki/Messerschmitt_Me_163#Me_163_Bhttps://en.wikipedia.org/wiki/Hydratehttps://en.wikipedia.org/wiki/Rocket_fuelhttps://en.wikipedia.org/wiki/Corrosion_inhibitorhttps://en.wikipedia.org/wiki/Astrolitehttps://en.wikipedia.org/wiki/Fuel_cellhttps://en.wikipedia.org/wiki/M-Stoffhttps://en.wikipedia.org/wiki/Phoenix_(spacecraft)https://en.wikipedia.org/wiki/F-16_Fighting_Falconhttps://en.wikipedia.org/wiki/World_War_IIhttps://en.wikipedia.org/wiki/Hydrazoic_acidhttps://en.wikipedia.org/wiki/Ammonium_nitratehttps://en.wikipedia.org/wiki/Methanolhttps://en.wikipedia.org/wiki/Curiosity_roverhttps://en.wikipedia.org/w/index.php?title=Molybdenum_nitride&action=edit&redlink=1https://en.wikipedia.org/wiki/Polymerizationhttps://en.wikipedia.org/wiki/Viking_programhttps://en.wikipedia.org/wiki/Solderhttps://en.wikipedia.org/w/index.php?title=Chain_extender&action=edit&redlink=1https://en.wikipedia.org/wiki/Monopropellanthttps://en.wikipedia.org/wiki/Emergency_power_unithttps://en.wikipedia.org/wiki/Lockheed_Corporationhttps://en.wikipedia.org/wiki/Hydrazine_sulfatehttps://en.wikipedia.org/wiki/Thin-film_transistorhttps://en.wikipedia.org/wiki/Aluminahttps://en.wikipedia.org/wiki/Spandexhttps://en.wikipedia.org/wiki/Carbon_nanofiberhttps://en.wikipedia.org/wiki/Flux_(metallurgy)https://en.wikipedia.org/wiki/Iridiumhttps://en.wikipedia.org/wiki/Photographic_developerhttps://en.wikipedia.org/wiki/C-Stoffhttps://en.wikipedia.org/wiki/Catalysthttps://en.wikipedia.org/wiki/Cachexiahttps://en.wikipedia.org/wiki/Liquid_crystal_displayhttps://en.wikipedia.org/wiki/Polyurethanehttps://en.wikipedia.org/wiki/Space_Shuttlehttps://en.wikipedia.org/wiki/Catalyst


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Anhydrous hydrazine being loaded

into theMESSENGERspace probe.

Note the safety suit the technician iswearing

2. N2H4 N2+ 2 H23. 4 NH3+ N2H4 3 N2+ 8 H2

Reactions 1 and 2 are extremely exothermic (the catalyst chamber can reach 800 C in a matter of

milliseconds,[31]) and they produce large volumes of hot gas from a small volume of liquid,[32]making

hydrazine a fairly efficient thruster propellant with a vacuum specific impulse of about 220 seconds.[34]

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 NH3that is dissociated in Reactio3 a higher temperature is desirable for rocket thrusters, while more molecules are desirable when thereactions 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 nitrogen tetroxide, N2O4,

sometimes known as dinitrogen tetroxide. These reactions are extremely exothermic, and the burning is alshypergolic, which means that it starts without any external ignition

source.[35]

There are ongoing efforts to replace hydrazine along with otherhighly toxic substances from the aerospace industry. Promisingalternatives include hydroxylammonium nitrate, 2-

Dimethylaminoethylazide (DMAZ)[36]and energetic ionic

liquids.[37]

Fuel cells

The Italian catalyst manufacturer Acta has proposed using hydrazineas an alternative to hydrogen in fuel cells. The chief benefit of using

hydrazine is that it can produce over 200 mW/cm2more than asimilar hydrogen cell without the need to use expensive platinum

catalysts.[38]As the fuel is liquid at room temperature, it can behandled and stored more easily than hydrogen. By storing thehydrazine in a tank full of a double-bonded carbon-oxygencarbonyl, the fuel reacts and forms a safe solid called hydrazone. Bythen flushing the tank with warm water, the liquid hydrazine hydrate

is released. Hydrazine has a higher electromotive force of 1.56 Vcompared to 1.23 V for hydrogen. Hydrazine breaks down in thecell to form nitrogen and hydrogen which bonds with oxygen,

releasing water.[38]Hydrazine was used in fuel cells manufactured by Allis-Chalmers Corp., including somthat provided electric power in space satellites in the 1960s.

Gun propellant
https://en.wikipedia.org/wiki/Watthttps://en.wikipedia.org/wiki/File:Hypergolic_Fuel_for_MESSENGER.jpghttps://en.wikipedia.org/wiki/Hypergolichttps://en.wikipedia.org/wiki/Fuel_cellhttps://en.wikipedia.org/wiki/Hydrogenhttps://en.wikipedia.org/wiki/Platinumhttps://en.wikipedia.org/wiki/Hydroxylammonium_nitratehttps://en.wikipedia.org/wiki/MESSENGERhttps://en.wikipedia.org/wiki/Catalysthttps://en.wikipedia.org/wiki/Allis-Chalmershttps://en.wikipedia.org/wiki/Unsymmetrical_dimethylhydrazinehttps://en.wikipedia.org/wiki/Exothermichttps://en.wikipedia.org/wiki/2-Dimethylaminoethylazidehttps://en.wikipedia.org/wiki/Carbonylhttps://en.wikipedia.org/wiki/Specific_impulsehttps://en.wikipedia.org/wiki/Nitrogenhttps://en.wikipedia.org/wiki/Monomethylhydrazinehttps://en.wikipedia.org/wiki/Electromotive_forcehttps://en.wikipedia.org/w/index.php?title=Acta_(chemical_company)&action=edit&redlink=1https://en.wikipedia.org/wiki/Volthttps://en.wikipedia.org/wiki/Hydrazonehttps://en.wikipedia.org/wiki/Endothermichttps://en.wikipedia.org/wiki/Carbonhttps://en.wikipedia.org/wiki/Nitrogen_tetroxidehttps://en.wikipedia.org/wiki/Dinitrogen_tetroxidehttps://en.wikipedia.org/wiki/Hydrogenhttps://en.wikipedia.org/wiki/Oxygen


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A mixture of 63% hydrazine, 32% hydrazine nitrate and 5% water is a standard propellant for experimentabulk-loaded liquid propellant artillery. The propellant mixture above is one of the most predictable andstable, with a flat pressure profile during firing. Misfires are usually caused by inadequate ignition. Themovement of the shell after a misignition causes a large bubble with a larger ignition surface area, and thegreater rate of gas production causes very high pressure, sometimes including catastrophic tube failures (i.

explosions).[39]

Hazards

Hydrazine is highly toxic, and dangerously unstable in the anhydrous form. According to the U.S.Environmental Protection Agency:

Symptoms of acute (short-term) exposure to high levels of hydrazine may include irritation ofthe eyes, nose, and throat, dizziness, headache, nausea, pulmonary edema, seizures, coma inhumans. Acute exposure can also damage the liver, kidneys, and central nervous system. Theliquid is corrosive and may produce dermatitis from skin contact in humans and animals.

Effects to the lungs, liver, spleen, and thyroid have been reported in animals chronicallyexposed to hydrazine via inhalation. Increased incidences of lung, nasal cavity, and liver

tumors have been observed in rodents exposed to hydrazine.[40]

Limit tests for hydrazine in pharmaceuticals suggest that it should be in the low ppm range.[41]Hydrazine

may also cause steatosis.[42]At least one human is known to have died after 6 months of sublethal exposur

to hydrazine hydrate.[43]

On February 21, 2008, the United States government destroyed the disabled spy satellite USA 193 with a

sea-launched missile, reportedly due to the potential danger of a hydrazine release if it re-entered the Earthatmosphere intact.[44]

History

The name "hydrazine" was coined by Emil Fischer in 1875 he was trying to produce organic compounds

that consisted of mono-substituted hydrazine.[45]By 1887, Theodor Curtius had produced hydrazine sulfatby treating organic diazides with dilute sulfuric acid however, he was unable to obtain pure hydrazine,

despite repeated efforts.[46]Pure anhydrous hydrazine was first prepared by the Dutch chemist Lobry de

Bruyn in 1895.[47]

See also

DiazeneHydrazine sulfateList of Stoffs

Nitrous oxide fuel blendUSA 193
https://en.wikipedia.org/wiki/Anhydroushttps://en.wikipedia.org/wiki/Seizureshttps://en.wikipedia.org/wiki/Theodor_Curtiushttps://en.wikipedia.org/wiki/Steatosishttps://en.wikipedia.org/wiki/Nitrous_oxide_fuel_blendhttps://en.wikipedia.org/wiki/Diazenehttps://en.wikipedia.org/wiki/Comahttps://en.wikipedia.org/wiki/List_of_Stoffshttps://en.wikipedia.org/wiki/Pulmonary_edemahttps://en.wikipedia.org/wiki/Corrosivehttps://en.wikipedia.org/wiki/Kidneyshttps://en.wikipedia.org/wiki/U.S._Environmental_Protection_Agencyhttps://en.wikipedia.org/wiki/Lungshttps://en.wikipedia.org/wiki/Thyroidhttps://en.wikipedia.org/wiki/Hydrazine_sulfatehttps://en.wikipedia.org/wiki/Liverhttps://en.wikipedia.org/wiki/Cornelis_Adriaan_Lobry_van_Troostenburg_de_Bruynhttps://en.wikipedia.org/wiki/Bulk_loaded_liquid_propellantshttps://en.wikipedia.org/wiki/Hermann_Emil_Fischerhttps://en.wikipedia.org/wiki/Dermatitishttps://en.wikipedia.org/wiki/Central_nervous_systemhttps://en.wikipedia.org/wiki/Spleenhttps://en.wikipedia.org/wiki/USA_193https://en.wikipedia.org/wiki/USA_193


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2. "hydrazine - PubChem Public Chemical Database" (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9321). The PubChem Project. USA: National Center for Biotechnology Information.

3. "NIOSH Pocket Guide to Chemical Hazards #0329" (http://www.cdc.gov/niosh/npg/npgd0329.html). National

Institute for Occupational Safety and Health (NIOSH).4. Hall H.K. (1957).J. Am. Chem. Soc.79: 5441. doi:10.1021/ja01577a030

(https://dx.doi.org/10.1021%2Fja01577a030). Missing or empty |title=(help)5. Greenwood, Norman N. Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann

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Synth. Coll. Vol.1, p. 30914. "Hydrazine: Chemical product info" (http://chemindustry.ru/Hydrazine.php). chemindustry.ru. Retrieved

2007-01-08.15. Chemistry of Petrochemical Processes, 2nd edition, Gulf Publishing Company, 1994-2000, Page 14816. Riegel, Emil Raymond (1992). "Riegel's Handbook of Industrial Chemistry". p. 192. |chapter=ignored (help).

17. Strous, M., and Jetten, M.S.M. (2004) Anaerobic oxidation of methane and ammonium. Ann Rev Microbiol 5899117.18. Brian Handwerk (9 November 2005). "Bacteria Eat Human Sewage, Produce Rocket Fuel"

(http://news.nationalgeographic.com/news/2005/11/1109_051109_rocketfuel.html). National Geographic.Retrieved 2007-11-12.

19. Hashida C, Hayashi K, Jie L, Haga S, Sakurai M, Shimizu H (June 1990). "[Quantities of agaritine inmushrooms (Agaricus bisporus) and the carcinogenicity of mushroom methanol extracts on the mouse bladderepithelium]". Nippon Koshu Eisei Zasshi(in Japanese) 37(6): 4005. PMID 2132000(https://www.ncbi.nlm.nih.gov/pubmed/2132000).

20. Sieger AA (ed.) (1998-01-01). "Spore Prints #338" (http://www.psms.org/sporeprints/sp338.html).Bulletin ofthe Puget Sound Mycological Society. Retrieved 2008-10-13.

21. Day, A. C. Whiting, M. C. "Acetone Hydrazone" (http://www.orgsyn.org/demo.aspx?prep=cv6p0010). Org.Synth. Coll. Vol.6, p. 10

22. Wiley, R. H. Hexner, P. E. "3,5-Dimethylpyrazole" (http://www.orgsyn.org/demo.aspx?prep=cv4p0351). Org.Synth. Coll. Vol.4, p. 351

23. Friedman, L Litle, R. L. Reichle, W. R. "p-Toluenesulfonyl Hydrazide" (http://www.orgsyn.org/demo.aspx?prep=cv5p1055). Org. Synth. Coll. Vol.5, p. 1055

24. Weinshenker, N. M. Shen, C. M. Wong, J. Y. (1988). "Polymeric carbodiimide"(http://www.orgsyn.org/demo.aspx?prep=cv6p0951). Org. Synth. Coll. Vol.6, p. 951

25. Stankovich et al., Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide,Carbon, 45, (2007) 15581565

26. Safety Data Sheet Mallinckrodt (http://hazard.com/msds/mf/baker/baker/files/h3633.htm)27. Gagnon B, Bruera E (May 1998). "A review of the drug treatment of cachexia associated with cancer".Drugs5
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: . o : . - - ps: x. o .org . - -00005). PMID 9585863 (https://www.ncbi.nlm.nih.gov/pubmed/9585863).

28. G. B. Manelis (2003). Thermal decomposition and combustion of explosives and propellants(http://books.google.com/books?id=_Xz7_o23J_0C&pg=PA235). CRC Press. p. 235. ISBN 0-415-29984-5.

29. Klaptke, T. Peter S. White Inis C. Tornieporth-Oetting (1996). "Reaction of hydrazinium azide with sulfuric

acid: the X-ray structure of [N2H6][SO4]".Polyhedron15(15): 25792582. doi:10.1016/0277-5387(95)00527-7(https://dx.doi.org/10.1016%2F0277-5387%2895%2900527-7).

30. Clark, John D. (1972).Ignition! An Informal History of Liquid Rocket Propellants(http://library.sciencemadness.org/library/books/ignition.pdf) (PDF). New Brunswick, New Jersey: RutgersUniversity Press. p. 13. ISBN 0-8135-0725-1.

31. Vieira, R. C. Pham-Huu N. Keller M. J. Ledoux (2002). "New carbon nanofiber/graphite felt composite for uas a catalyst support for hydrazine catalytic decomposition". Chemical Communications(9): 954955.doi:10.1039/b202032g (https://dx.doi.org/10.1039%2Fb202032g).

32. Chen, Xiaowei et al. (April 2002). "Catalytic Decomposition of Hydrazine over Supported Molybdenum NitrideCatalysts in a Monopropellant Thruster". Catalysis Letters79: 2125. doi:10.1023/A:1015343922044(https://dx.doi.org/10.1023%2FA%3A1015343922044).

33. Haws, J .L. Harden, D.G. (1965). "Thermodynamic Properties of Hydrazine,".Journal of Spacecraft and Rocke2 (6): 972974. doi:10.2514/3.28327 (https://dx.doi.org/10.2514%2F3.28327).

34. Monopropellant Hydrazine Thrusters(http://cs.astrium.eads.net/sp/SpacecraftPropulsion/MonopropellantThrusters.html)

35. Mitchell, Martha et al. (2007). "Thermodynamic analysis of equations of state for the monopropellant hydrazineJOURNAL OF THERMOPHYSICS AND HEAT TRANSFER21: 243247. doi:10.2514/1.22798(https://dx.doi.org/10.2514%2F1.22798).

36. "Rocket Propellant Development Efforts at Purdue University - PowerPoint PPT Presentation"(http://www.powershow.com/view/11713f-M2E0O/Rocket_Propellant_Development_Efforts_at_Purdue_University_powerpoint_ppt_presentation).Retrieved 21 April 2013.

37. Fahrat, Kamal Batonneau, Yann Brahmi, Rachid Kappenstein, Charles (September 22, 2011). "Chapter 21:Application of Ionic Liquids to Space Propulsion". In Handy, Scott.Applications of Ionic Liquids in Science anTechnology (http://www.intechopen.com/books/applications-of-ionic-liquids-inscience-%20and-technology/application-of-ionic-liquids-to-space-propulsion). InTech. doi:10.5772/23807

(https://dx.doi.org/10.5772%2F23807). ISBN 978-953-307-605-8. Retrieved 2013-07-20.38. "Liquid asset" (http://www.theengineer.co.uk/Articles/303939/Liquid+asset.htm). The Engineer. 2008-01-15.

Retrieved 2015-01-09.39. Knapton, John, Stobie, Irvin, Elmore, Les ARl-TR-81 A review of the Bulk-Loaded Liquid Propellant Gun

Program for Possible Relevance to the Electrothermal Chemical Propulsion Program, Army Research LaboratorMarch 1993 At Accessed (http://www.dtic.mil/cgi-bin/GetTRDoc?Location=U2&doc=GetTRDoc.pdf&AD=ADA263143) 2011-7-23

40. United States Environmental Protection Agency.Hydrazine Hazard Summary-Created in April 1992 Revised inJanuary 2000[1] (http://www.epa.gov/ttn/atw/hlthef/hydrazin.html). Retrieved on February 21, 2008.

41. European Pharmacopeia Scientific Notes. Acceptance criteria for levels of hydrazine in substances forpharmaceutical use and analytical methods for its determination[2]

(http://www.ncbi.nlm.nih.gov/sites/entrez/17691211). Retrieved on April 22, 2008.42. PHM 450 Course, Spring 2009, Michigan State University43. International Programme on Chemical Safety,Environmental Health Criteria for Hydrazine

(http://www.inchem.org/documents/ehc/ehc/ehc68.htm), Section 9.2.1, dated 1987. Retrieved on February 21,2008.

44. "IEEE Spectrum Online. U.S. Satellite Shootdown" (http://spectrum.ieee.org/aug08/6533). Retrieved 2008-08-045. Emil Fischer (1875) "Ueber aromatische Hydrazinverbindungen"

(http://gallica.bnf.fr/ark:/12148/bpt6k90680z/f596.image.langEN) (On aromatic hydrazine compounds),Berichteder Deutschen chemischen Gesellschaft zu Berlin, 8: 589-594.

46. See:Theodor Curtius (1887) "Ueber das Diamid (Hydrazin)"

(htt :// allica.bnf.fr/ark:/12148/b t6k907102/f818.ima e.lan EN) (On diamide (h drazine)),Berichte der
https://dx.doi.org/10.1039%2Fb202032ghttp://cs.astrium.eads.net/sp/SpacecraftPropulsion/MonopropellantThrusters.htmlhttp://spectrum.ieee.org/aug08/6533https://en.wikipedia.org/wiki/Digital_object_identifierhttp://www.theengineer.co.uk/Articles/303939/Liquid+asset.htmhttps://dx.doi.org/10.2514%2F3.28327https://dx.doi.org/10.1016%2F0277-5387%2895%2900527-7https://en.wikipedia.org/wiki/Special:BookSources/978-953-307-605-8https://en.wikipedia.org/wiki/Digital_object_identifierhttp://gallica.bnf.fr/ark:/12148/bpt6k907102/f818.image.langENhttps://dx.doi.org/10.2165%2F00003495-199855050-00005https://en.wikipedia.org/wiki/Special:BookSources/0-415-29984-5https://en.wikipedia.org/w/index.php?title=Journal_of_Spacecraft_and_Rockets&action=edit&redlink=1https://en.wikipedia.org/wiki/International_Standard_Book_Numberhttp://www.ncbi.nlm.nih.gov/sites/entrez/17691211http://www.dtic.mil/cgi-bin/GetTRDoc?Location=U2&doc=GetTRDoc.pdf&AD=ADA263143https://en.wikipedia.org/w/index.php?title=JOURNAL_OF_THERMOPHYSICS_AND_HEAT_TRANSFER&action=edit&redlink=1http://books.google.com/books?id=_Xz7_o23J_0C&pg=PA235https://en.wikipedia.org/wiki/Special:BookSources/0-8135-0725-1https://en.wikipedia.org/wiki/Digital_object_identifierhttp://www.powershow.com/view/11713f-M2E0O/Rocket_Propellant_Development_Efforts_at_Purdue_University_powerpoint_ppt_presentationhttps://en.wikipedia.org/wiki/Digital_object_identifierhttps://dx.doi.org/10.5772%2F23807http://www.epa.gov/ttn/atw/hlthef/hydrazin.htmlhttp://www.inchem.org/documents/ehc/ehc/ehc68.htmhttps://dx.doi.org/10.1023%2FA%3A1015343922044https://en.wikipedia.org/wiki/United_States_Environmental_Protection_Agencyhttps://en.wikipedia.org/w/index.php?title=European_Pharmacopeia_Scientific_Notes&action=edit&redlink=1https://en.wikipedia.org/wiki/International_Standard_Book_Numberhttps://en.wikipedia.org/wiki/Digital_object_identifierhttps://en.wikipedia.org/wiki/International_Standard_Book_Numberhttps://www.ncbi.nlm.nih.gov/pubmed/9585863https://dx.doi.org/10.2514%2F1.22798https://en.wikipedia.org/wiki/Digital_object_identifierhttps://en.wikipedia.org/wiki/PubMed_Identifierhttps://en.wikipedia.org/wiki/Digital_object_identifierhttp://library.sciencemadness.org/library/books/ignition.pdfhttp://www.intechopen.com/books/applications-of-ionic-liquids-inscience-%20and-technology/application-of-ionic-liquids-to-space-propulsionhttps://en.wikipedia.org/wiki/Chemical_Communicationshttp://gallica.bnf.fr/ark:/12148/bpt6k90680z/f596.image.langENhttps://en.wikipedia.org/wiki/Catalysis_Letters


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Look up hydrazineinWiktionary, the freedictionary.

External links

The Late Show with Rob! Tonights Special Guest: Hydrazine(PDF)

(http://www.princeton.edu/~orggroup/supergroup_pdf/rmatunasAGM5hydrazine.pdf) RobertMatunasHydrazine - chemical product info: properties, production, applications.(http://chemindustry.ru/Hydrazine.php)Hydrazine toxicity (http://www.gasdetection.com/TECH/hydrazine.html)CDC - NIOSH Pocket Guide to Chemical Hazards (http://www.cdc.gov/niosh/npg/npgd0329.html)

Retrieved from "https://en.wikipedia.org/w/index.php?title=Hydrazine&oldid=668880269"

Categories: Hydrazines Bases Hazardous air pollutants Rocket fuels Monopropellants

Corrosion inhibitors Monoamine oxidase inhibitors Reducing agents Nitrogen hydridesIARC Group 2B carcinogens

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Deutschen chemischen Gesellschaft zu Berlin, 20: 1632-1634.Theodor Curtius and Rudolf Jay (1889) "Diazo- und Azoverbindungen der Fettreihe. IV. Abhandlung.Ueber das Hydrazin" (http://books.google.com/books?id=GHYMAAAAYAAJ&pg=PA27#v=onepage&q&f=false) (Diazo- and azo- compounds of alkanes.Fourth treatise. On hydrazine.), Journal fr praktische Chemie, 147: 27-58.Th. Curtius (1889) "Diazo- und Azoverbindungen der Fettreihe. V. Abhandlung. Ueber die Constitutionder fetten Diazo- und Azokrper und ber die Bildung des Diamids und seiner Derivate"(http://books.google.com/books?id=GHYMAAAAYAAJ&pg=PA107#v=onepage&q&f=false) (Diazo- anazo- compounds of alkanes. Fifth treatise. On the constitution of alkane diazo- and azo- substances and onthe formation of diamides and their derivatives),Journal fr praktische Chemie, 147: 107-139. On p. 12Curtius admits: "Das freie Diamid NH2-NH2ist noch nicht analysirt worden." (Free hydrazine hasn't beeanalyzed yet.)Th. Curtius and H. Schulz (1890) "Ueber Hydrazinehydrat und die Halogenverbindungen desDiammoniums" (http://gallica.bnf.fr/ark:/12148/bpt6k90790j/f527.image.langEN) (On hydrazine hydrateand the halogen compounds of diammonium),Journal fr praktische Chemie, 150: 521-549.

47. See:C. A. Lobry de Bruyn (1894) "Sur l'hydrazine (diamide) libre" (On free hydrazine (diamide)), Recueil deTravaux Chimiques des Pays-Bas, 13(8) : 433-440.C. A. Lobry de Bruyn (1895) "Sur l'hydrate d'hydrazine" (On the hydrate of hydrazine), Recueil desTravaux Chimiques des Pays-Bas, 14(3) : 85-88.C. A. Lobry de Bruyn (1896) "L'hydrazine libre I" (Free hydrazine, Part 1),Recueil des TravauxChimiques des Pays-Bas, 15(6) : 174-184.
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