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Revision as of 14:35, 2 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit		Latest revision as of 16:11, 3 January 2025 edit undoTrasheater Midir (talk | contribs)Extended confirmed users3,638 edits →Small-scale, niche, and research: added picture, yes I know it would display in the arse end of article, under the infobox
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			{{Short description|Colorless flammable liquid with an ammonia-like odor}}
	{{for|the antidepressant|Hydrazine (antidepressant)}}
			{{cs1 config|name-list-style=vanc}}
			{{For|the class of antidepressants|hydrazine (antidepressant)}}
			{{Distinguish|hydralazine|hydroxyzine}}
			{{Use American English|date=July 2019}}<!-- This article uses American spelling.-->
	{{Chembox		{{Chembox
	| Verifiedfields = changed		|Verifiedfields = changed
	| Watchedfields = changed		|Watchedfields = changed
	| verifiedrevid = 398739305		|verifiedrevid = 458641690
	| ImageFileL1 = Hydrazin.svg		|ImageFileL1 = Hydrazin.svg
	| ImageFileL1_Ref = {{chemboximage|correct|??}}		|ImageFileL1_Ref = {{chemboximage|correct|??}}
			|ImageNameL1 = Skeletal formula of hydrazine with all explicit hydrogens added
	| ImageSizeL1 = 121
			|ImageFileR1 = Hydrazine-3D-vdW.png
	| ImageNameL1 = Skeletal formula of hydrazine with all explicit hydrogens added
			|ImageFileR1_Ref = {{chemboximage|correct|??}}
	| ImageFileR1 = Hydrazine-3D-vdW.png
			|ImageNameR1 = Spacefill model of hydrazine
	| ImageFileR1_Ref = {{chemboximage|correct|??}}
			|ImageFileL2 = Hydrazine-2D-A1.png
	| ImageSizeR1 = 121
			|ImageFileL2_Ref = {{chemboximage|correct|??}}
	| ImageNameR1 = Spacefill model of hydrazine
			|ImageNameL2 = Stereo, skeletal formula of hydrazine with all explicit hydrogens added
	| ImageFileL2 = Hydrazine-2D-A1.png
			|ImageFileR2 = Hydrazine-3D-balls.png
	| ImageFileL2_Ref = {{chemboximage|correct|??}}
			|ImageFileR2_Ref = {{chemboximage|correct|??}}
	| ImageSizeL2 = 121
	| ImageNameL2 = Stereo, skeletal formula of hydrazine with all explicit hydrogens added		|ImageNameR2 = Ball and stick model of hydrazine
	| ImageFileR2 = Hydrazine-3D-balls.png		|ImageFile3 = Anhydrous hydrazine.png
			|ImageCaption3 = Anhydrous hydrazine
	| ImageFileR2_Ref = {{chemboximage|correct|??}}
	| ImageSizeR2 = 121		| ImageSize3 = 180px
			|IUPACName = Hydrazine<ref name = "hydrazine - PubChem Public Chemical Database" >{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9321|title=hydrazine—PubChem Public Chemical Database|work=The PubChem Project|location=USA|publisher=National Center for Biotechnology Information}}</ref>
	| ImageNameR2 = Ball and stick model of hydrazine
	| SystematicName = Hydrazine<ref name = "hydrazine - PubChem Public Chemical Database" >{{Cite web|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9321|title = hydrazine - PubChem Public Chemical Database|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref>		|SystematicName = Diazane<ref name = "hydrazine - PubChem Public Chemical Database" />
			|OtherNames = Diamine<ref name=NIOSH>{{Cite web|title=NIOSH Guide—Hydrazine|url=https://www.cdc.gov/niosh/npg/npgd0329.html|publisher=Centers for Disease Control|access-date=16 Aug 2012}}</ref><br />Tetrahydridodinitrogen(''N''-''N'')<br />Diamidogen
	| OtherNames = Diamine{{Citation needed|date = July 2011}}<br />
			|Section1={{Chembox Identifiers
	Diazane<ref name = "hydrazine - PubChem Public Chemical Database" />
			|CASNo = 302-01-2
	| Section1 = {{Chembox Identifiers
			|CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 302-01-2
			|PubChem = 9321
	| CASNo_Ref = {{cascite|correct|CAS}}
			|ChemSpiderID = 8960
	| PubChem = 9321
	| PubChem_Ref = {{Pubchemcite|correct|pubchem}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|UNII = 27RFH0GB4R
	| ChemSpiderID = 8960
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|UNII_Ref = {{fdacite|correct|FDA}}
			|EINECS = 206-114-9
	| UNII = 27RFH0GB4R
			|UNNumber = 2029
	| UNII_Ref = {{fdacite|correct|FDA}}
			|KEGG = C05361
	| EINECS = 206-114-9
			|KEGG_Ref = {{keggcite|correct|kegg}}
	| UNNumber = 2029
			|MeSHName = Hydrazine
	| KEGG = C05361
	| KEGG_Ref = {{keggcite|changed|kegg}}		|ChEBI_Ref = {{ebicite|correct|EBI}}
			|ChEBI = 15571
	| MeSHName = Hydrazine
			|ChEMBL = 1237174
	| ChEBI_Ref = {{ebicite|changed|EBI}}
			|ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEBI = 15571
			|RTECS = MU7175000
	| ChEMBL = <!-- blanked - oldvalue: 1237174 -->
			|Beilstein = 878137
	| ChEMBL_Ref = {{ebicite|changed|EBI}}
			|Gmelin = 190
	| RTECS = MU7175000
			|3DMet = B00770
	| Beilstein = 878137
	| Gmelin = 190		|SMILES = NN
			|StdInChI = 1S/H4N2/c1-2/h1-2H2
	| 3DMet = B00770
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| SMILES = NN
	| StdInChI = 1S/H4N2/c1-2/h1-2H2		|InChI = 1/H4N2/c1-2/h1-2H2
			|StdInChIKey = OAKJQQAXSVQMHS-UHFFFAOYSA-N
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| InChI = 1/H4N2/c1-2/h1-2H2
	| StdInChIKey = OAKJQQAXSVQMHS-UHFFFAOYSA-N		|InChIKey = OAKJQQAXSVQMHS-UHFFFAOYAZ
			}}
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|Section2={{Chembox Properties
	| InChIKey = OAKJQQAXSVQMHS-UHFFFAOYAZ
			|Formula = {{Chem2|N2H4}}
			|MolarMass = 32.0452 g/mol
			|Appearance = Colorless, fuming, oily liquid<ref name=PGCH/>
			|Odor = ]-like<ref name=PGCH/>
			|Density = 1.021 g/cm<sup>3</sup>
			|MeltingPtK = 275
			|BoilingPtK = 387
			|LogP = 0.67
			|VaporPressure = 1 kPa (at 30.7 °C)
			|pKa = 8.10 ({{chem2|+}})<ref>{{Cite journal |display-authors=et al|vauthors=Hall HK|year=1957|title=Correlation of the Base Strengths of Amines1|journal=]|volume=79|issue=20|page=5441|doi=10.1021/ja01577a030}}</ref>
			|ConjugateAcid = ]
			|pKb = 5.90
			|RefractIndex = 1.46044 (at 22 °C)
			|Viscosity = 0.876 cP
			|Solubility = Miscible<ref name=PGCH/>
	}}		}}
	| Section2 = {{Chembox Properties		|Section3={{Chembox Structure
			|MolShape = Triangular pyramidal at N
	| Formula = {{Chem|N|2|H|4}}
			|Dipole = 1.85 D<ref name="Greenwood 1997">{{Greenwood&Earnshaw2nd}}</ref>
	| MolarMass = 32.0452 g mol<sup>-1</sup>
	| ExactMass = 32.037448138 g mol<sup>-1</sup>
	| Appearance = Colourless liquid
	| Density = 1.021 g cm<sup>-3</sup>
	| MeltingPtK = 275
	| BoilingPtK = 387
	| LogP = 0.67
	| VaporPressure = 1 kP (at 30.7 °C)
	| pKa = 8.10<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441.</ref>
	| pKb = 5.90
	| RefractIndex = 1.46044 (at 22 °C)
	| Viscosity = 0.876 cP
	}}		}}
	| Section3 = {{Chembox Structure		|Section4={{Chembox Thermochemistry
			|DeltaHf = 50.63 kJ/mol
	| MolShape = Triangular pyramidal at N
			|Entropy = 121.52 J/(K·mol)
	| Dipole = 1.85 D<ref name="Greenwood 1997">{{Greenwood&Earnshaw2nd}}</ref>
	}}		}}
	| Section4 = {{Chembox Thermochemistry		|Section5={{Chembox Hazards
			|ExternalSDS =
	| DeltaHf = 50.63 kJ mol<sup>-1</sup>
			|GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS health hazard}} {{GHS environment}}
	| Entropy = 121.52. J K<sup>-1</sup> mol<sup>-1</sup>
			|GHSSignalWord = '''DANGER'''
			|HPhrases = {{H-phrases|226|301|311|314|317|331|350|410}}
			|PPhrases = {{P-phrases|201|261|273|280|301+310|305+351+338}}
			|NFPA-F = 4
			|NFPA-H = 4
			|NFPA-R = 3
			|FlashPtC = 52
			|AutoignitionPtC = 24 to 270
			|ExploLimits = 1.8–100%
			|LD50 = 59–60 mg/kg (oral in rats, mice)<ref>{{Cite book |display-authors=et al|vauthors=Martel B, Cassidy K|title=Chemical Risk Analysis: A Practical Handbook|publisher=Butterworth–Heinemann |location=Amsterdam|year=2004|page=361|isbn=978-1-903996-65-2|oclc=939257974}}</ref>
			|PEL = TWA 1 ppm (1.3 mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0329}}</ref>
			|IDLH = Ca <ref name=PGCH/>
			|REL = Ca C 0.03 ppm (0.04 mg/m<sup>3</sup>) <ref name=PGCH/>
			|LC50 = 260 ppm (rat, 4 ])<br/>630 ppm (rat, 1 h)<br/>570 ppm (rat, 4 h)<br/>252 ppm (mouse, 4&nbsp;h)<ref name=IDLH>{{IDLH|302012|Hydrazine}}</ref>
	}}		}}
	| Section5 = {{Chembox Hazards		|Section6={{Chembox Related
			|OtherCations = ]
	| ExternalMSDS =
			|OtherAnions = ]<br/>]<br/>]<br/>]
	| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS health hazard}} {{GHS environment}}
			|OtherFunction_label = Binary ]s
	| GHSSignalWord = '''DANGER'''
			|OtherFunction = ]<br/>]
	| HPhrases = {{H-phrases|226|301|311|314|317|331|350|410}}
			|OtherCompounds = ]<br/>]<br/>]<br/>]
	| PPhrases = {{P-phrases|201|261|273|280|301+310|305+351+338}}
	| EUIndex = 007-008-00-3
	| EUClass = {{Hazchem T}} {{Hazchem N}}
	| RPhrases = {{R45}}, {{R10}}, {{R23/24/25}}, {{R34}}, {{R43}}, {{R50/53}}
	| SPhrases = {{S53}}, {{S45}}, {{S60}}, {{S61}}
	| NFPA-F = 4
	| NFPA-H = 4
	| NFPA-R = 3
	| FlashPt = 52 °C
	| Autoignition = 24–270 °C
	| ExploLimits = 1.8–99.99%
	| LD50 = 59–60 mg/kg (oral in rats, mice)<ref>{{cite book |author=Martel, B.; Cassidy, K. |title=Chemical Risk Analysis: A Practical Handbook |publisher=Butterworth–Heinemann |year=2004 |pages=361 |isbn=1903996651}}</ref>}}
	| Section6 = {{Chembox Related
	| OtherCpds = ]<br />
	]<br />
	]
	}}		}}
	}}		}}
			'''Hydrazine''' is an ] with the ] {{Chem2|N2H4|auto=yes}}. It is a simple ], and is a colourless flammable liquid with an ]-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydrazine hydrate ({{Chem2|N2H4*''x''H2O}}).
	'''Hydrazine''' is an ] with the ] N<sub>2</sub>H<sub>4</sub>. It is a colourless flammable liquid with an ]-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually.<ref name=Ullmann>Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. {{DOI|10.1002/14356007.a13_177}}.</ref> Hydrazine is mainly used as a ] in preparing ] ]s, but significant applications also include its uses as a ] to ] catalysts and ]s. Additionally, hydrazine is used in various ] and to prepare the gas precursors used in ]. Hydrazine is used within both nuclear and conventional electrical power plant steam cycles to control concentrations of dissolved oxygen in an effort to reduce corrosion.
			Hydrazine is mainly used as a ] in preparing ], but applications also include its uses as a ] to ]s and ]s, as well as a long-term ] for in-] spacecraft propulsion. 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 ] to control concentrations of dissolved oxygen in an effort to reduce corrosion.<ref>{{Cite journal |vauthors=Tsubakizaki S, Takada M, Gotou H, Mawatari K, Ishihara N, Kai R |date=2009 |title=Alternatives to Hydrazine in Water Treatment at Thermal Power Plants |url=https://www.mhi.co.jp/technology/review/pdf/e462/e462043.pdf |journal=Mitsubishi Heavy Industries Technical Review |volume=6 |issue=2 |pages=43–47}}</ref>
	==Molecular structure and properties==
			{{asof|2000}}, approximately 120,000 tons of hydrazine hydrate (corresponding to a 64% solution of hydrazine in water by weight) were manufactured worldwide per year.<ref name="Ullmann"/>
	Hydrazine forms a monohydrate that is more dense (1.032 g/cm<sup>3</sup>) than the anhydrous material.
			] are a class of organic substances derived by replacing one or more hydrogen atoms in hydrazine by an organic group.<ref name="Ullmann"/>
	Hydrazine can arise via coupling a pair of ] molecules by removal of one hydrogen per molecule. Each H<sub>2</sub>N-N subunit is pyramidal in shape. The N-N distance is 1.45 Å (145 ]), and the molecule adopts a ].<ref>Miessler, Gary L. and Tarr, Donald A. '' Inorganic Chemistry, Third Edition'' Pearson Prentice Hall (2004) ISBN 0-13-035471-6.</ref> The ] is twice that of ]. These structural properties resemble those of gaseous ], which adopts a "skewed" ] conformation, and also experiences a strong rotational barrier.
			==Etymology and history==
	Hydrazine has ] (]) chemical properties comparable to those of ]:
			The name "hydrazine" was coined by ] in 1875; he was trying to produce organic compounds that consisted of mono-substituted hydrazine.<ref>{{Cite journal |vauthors=Fischer E |date=1875 |title=Über aromatische Hydrazinverbindungen |trans-title=On aromatic hydrazine compounds |url=https://gallica.bnf.fr/ark:/12148/bpt6k90680z/f596.image.langEN |journal=] |volume=8 |pages=589–594 |doi=10.1002/cber.187500801178}}</ref> 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.<ref>{{Cite journal |vauthors=Curtius T |date=1887 |title=Über das Diamid (Hydrazin) |trans-title=On diamide (hydrazine) |url=https://gallica.bnf.fr/ark:/12148/bpt6k907102/f818.image.langEN |journal=] |volume=20 |pages=1632–1634 |doi=10.1002/cber.188702001368}}</ref><ref>{{Cite book |title=Journal für praktische Chemie |vauthors=Curtius T, Jay R |publisher=Verlag von Johann Ambrosius Barth |year=1889 |veditors=Erdmann OL |volume=147 |chapter=Diazo- und Azoverbindungen der Fettreihe. IV. Abhandlung. über das Hydrazin |trans-chapter=Diazo- and azo- compounds of alkanes. Fourth treatise. On hydrazine |chapter-url=https://books.google.com/books?id=GHYMAAAAYAAJ&pg=PA27}} On p. 129, Curtius admits: "{{lang|de|''Das freie Diamid'' NH<sub>2</sub>-NH<sub>2</sub> ''ist noch nicht analysiert worden''.|italic=unset}}" </ref><ref>{{Cite book |title=Journal für praktische Chemie |vauthors=Curtius T, Schulz H |year=1890 |volume=150 |pages=521–549 |chapter=''Über Hydrazinehydrat und die Halogenverbindungen des Diammoniums'' |trans-chapter=On hydrazine hydrate and the halogen compounds of diammonium |chapter-url=https://gallica.bnf.fr/ark:/12148/bpt6k90790j/f527.image.langEN?lang=EN}}</ref> Pure anhydrous hydrazine was first prepared by the Dutch chemist ] in 1895.<ref>{{Cite journal |vauthors=Lobry de Bruyn CA |year=1894 |title=Sur l'hydrazine (diamide) libre |trans-title=On free hydrazine (diamide) |journal=] |volume=13 |issue=8 |pages=433–440 |doi=10.1002/recl.18940130816}}</ref><ref>{{Cite journal |vauthors=Lobry de Bruyn CA |date=1895 |title=Sur l'hydrate d'hydrazine |trans-title=On the hydrate of hydrazine |journal=] |volume=14 |issue=3 |pages=85–88 |doi=10.1002/recl.18950140302}}</ref><ref>{{Cite journal |vauthors=Lobry de Bruyn CA |date=1896 |title=L'hydrazine libre I |trans-title=Free hydrazine, Part 1 |journal=] |language=en |volume=15 |issue=6 |pages=174–184 |doi=10.1002/recl.18960150606}}</ref>
	:N<sub>2</sub>H<sub>4</sub> + H<sub>2</sub>O → <sup>+</sup> + OH<sup>−</sup>
	with the values:<ref>Handbook of Chemistry and Physics", 83rd edition, CRC Press, 2002</ref>
	: ''K<sub>b</sub>'' = 1.3 x 10<sup>−6</sup>
	: ''pK<sub>a</sub>'' = 8.1
	(for ammonia ''K<sub>b</sub>'' = 1.78 x 10<sup>−5</sup>)
			The nomenclature is a bi-valent form, with prefix ''hydr-'' used to indicate the presence of ] atoms and suffix beginning with ''-az-'', from ''azote'', the French word for ].
	Hydrazine is difficult to diprotonate:<ref>Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.</ref>
	:<sup>+</sup> + H<sub>2</sub>O → <sup>2+</sup> + OH<sup>−</sup> ''K''<sub>b</sub> = 8.4 x 10<sup>−16</sup>
			==Applications==
	The heat of combustion of hydrazine in oxygen (air) is 194.1 x 10<sup>5</sup> J/kg (9345 BTU/lb).<ref></ref>
			===Gas producers and propellants===
			The largest use of hydrazine is as a precursor to ]s. Specific compounds include ] and ], which produce {{nowrap|100–200 mL}} of gas per gram of precursor. In a related application, ], the gas-forming agent in ], is produced from hydrazine by reaction with ].<ref name=Ullmann/>
			Hydrazine is also used as a long-term ] on board ] vehicles, such as the ] mission 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 ] fighter jet, ],<ref>{{Cite journal |title=A Summary of NASA and USAF Hypergolic Propellant Related Spills and Fires |url=https://ntrs.nasa.gov/api/citations/20100038321/downloads/20100038321.pdf |journal=Kennedy Space Center}}</ref> ], and ] spy plane use hydrazine to fuel their Emergency Start System in the event of an engine stall.<ref>{{Cite web |url=http://oai.dtic.mil/oai/oai?verb=getRecord&metadataPrefix=html&identifier=ADA065595 |title=Exhaust Gas Composition of the F-16 Emergency Power Unit |last1=Suggs |first1=HJ|last2=Luskus|first2=LJ|date=1979|publisher=]|type=technical report |id=SAM-TR-79-2|archive-url=https://web.archive.org/web/20160304084802/http://oai.dtic.mil/oai/oai?verb=getRecord&metadataPrefix=html&identifier=ADA065595 |archive-date=4 March 2016|access-date=23 Jan 2019 |last3=Kilian|first3=HJ|last4=Mokry|first4=JW}}</ref>
	==Synthesis and manufacture==
	] synthesized free hydrazine for the first time in 1889 via a ] route.<ref>Curtius, ''J. Prakt. Chem''. '''1889''', 39, 107-39.</ref>
			===Precursor to pesticides and pharmaceuticals===
	Hydrazine is produced in the ] from ] (the active ingredient in many bleaches) and ], a process announced in 1907. This method relies on the reaction of ] with ammonia:<ref>{{OrgSynth | author = Adams, R.; Brown, B. K. | title = Hydrazine Sulfate | collvol = 1 | collvolpages = 309 | year = 1941 | prep = cv1p0309}}</ref>
			], synthesized using hydrazine, is an ] medication.]]
	:NH<sub>2</sub>Cl + NH<sub>3</sub> → H<sub>2</sub>N-NH<sub>2</sub> + HCl
	Another route of hydrazine synthesis involves oxidation of ] with ]:<ref>{{cite web|url=http://chemindustry.ru/Hydrazine.php|title=Hydrazine: Chemical product info|publisher=chemindustry.ru|accessdate=2007-01-08}}</ref>
			Hydrazine is a precursor to several pharmaceuticals and pesticides. Often these applications involve conversion of hydrazine to ] such as ]s and ]s. Examples of commercialized bioactive ] include ], ], ], ], metazachlor, metamitron, ], ], diclobutrazole, ], ],<ref name="OrgSynth"/> ], ],<ref name="Ullmann"/> and the ] insecticides.
	:(H<sub>2</sub>N)<sub>2</sub>C=O + NaOCl + 2 NaOH → N<sub>2</sub>H<sub>4</sub> + H<sub>2</sub>O + NaCl + Na<sub>2</sub>CO<sub>3</sub>
			Hydrazine compounds can be effective as active ingredients in insecticides, miticides, ]s, fungicides, antiviral agents, attractants, herbicides, or plant growth regulators.<ref>{{Cite web|url=https://patents.google.com/patent/US5304657A/en|title=Hydrazine compounds useful as pesticides|last1=Toki|first1=T|last2=Koyanagi|first2=T|date=1994|type=US patent|others=Ishihara Sangyo Kaisha Ltd (original assignee)|id=US5304657A|last3=Yoshida|first3=K|last4=Yamamoto|first4=K|last5=Morita|first5=M}}</ref>
	Hydrazine can be synthesized from ] and ] in the ], according to the following formula:
			===Small-scale, niche, and research===
	:2NH<sub>3</sub> + H<sub>2</sub>O<sub>2</sub> → H<sub>2</sub>N-NH<sub>2</sub> + 2H<sub>2</sub>O <ref>Chemistry of Petrochemical Processes, 2nd edition, Gulf Publishing Company, 1994-2000, Page 148</ref>
			]]]
			The Italian ] manufacturer Acta (chemical company) has proposed using hydrazine as an alternative to ] in ]s. The chief benefit of using hydrazine is that it can produce over 200 m]/cm<sup>2</sup> more than a similar hydrogen cell without requiring (expensive) ] catalysts.<ref name=":0">{{Cite news|url=https://www.theengineer.co.uk/liquid-asset-3/|title=Liquid asset|date=15 Jan 2008|work=]|access-date=23 Jan 2019|publisher=Centaur Media plc}}</ref> Because 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 ]-] ], the fuel reacts and forms a safe solid called ]. By then flushing the tank with warm water, the liquid hydrazine hydrate is released. Hydrazine has a higher ] of 1.56 ] compared to 1.23 V for hydrogen. Hydrazine breaks down in the cell to form ] and ] which bonds with oxygen, releasing water.<ref name=":0" /> Hydrazine was used in fuel cells manufactured by ], including some that provided electric power in space satellites in the 1960s.
			A mixture of 63% hydrazine, 32% ] and 5% water is a standard propellant for experimental ]. 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 mis-ignition 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).<ref name=":1">{{Cite web|url=https://apps.dtic.mil/dtic/tr/fulltext/u2/a263143.pdf|archive-url=https://web.archive.org/web/20200307105240/https://apps.dtic.mil/dtic/tr/fulltext/u2/a263143.pdf|url-status=live|archive-date=March 7, 2020|title=A Review of the Bulk-Loaded Liquid Propellant Gun Program for Possible Relevance to the Electrothermal Chemical Propulsion Program|last1=Knapton|first1=JD|last2=Stobie|first2=IC|date=Mar 1993|publisher=Army Research Laboratory|id=|last3=Elmore|first3=L}}</ref> From January–June 1991, the ] conducted a review of early bulk-loaded liquid propellant gun programs for possible relevance to the electrothermal chemical propulsion program.<ref name=":1" />
	In the ], hydrazine is produced in several steps from ], ammonia, and hydrogen peroxide. Acetone and ammonia first react to give the ] followed by oxidation with ] to the ], a three-membered ring containing carbon, oxygen, and nitrogen, followed by ] to the ], a process that couples two nitrogen atoms. This hydrazone reacts with one more equivalent of acetone, and the resulting ] is hydrolyzed to give hydrazine, regenerating acetone. Unlike the Raschig process, this process does not produce salt. The PCUK stands for ], a French chemical manufacturer.<ref>{{Cite journal | last = Riegel | first = Emil Raymond | contribution = Hydrazine | title = Riegel's Handbook of Industrial Chemistry | page = 192 | year = 1992 | postscript = <!-- Bot inserted parameter. Either remove it; or change its value to "." for the cite to end in a ".", as necessary. -->}}.</ref>
			The ] (USAF) regularly uses H-70, a 70% hydrazine 30% water mixture, in operations employing the ] fighter aircraft and the ] reconnaissance aircraft. The single jet engine F-16 utilizes hydrazine to power its ] (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.<ref>{{Cite web|url=https://www.robins.af.mil/Portals/59/documents/technicalorders/00-25-172.pdf?ver=2016-08-22-142719-060|title=Ground Servicing of Aircraft and Static Grounding/Bonding|date=13 Mar 2017|website=]|type=technical manual|id=TO 00-25-172|access-date=23 Nov 2018}}</ref>
	Hydrazine can also be produced via the so-called ] and ]es.
			====Rocket fuel====
	==Hydrazine derivatives==
			] (pure, not in solution) hydrazine being loaded into the '']'' space probe (orbital reconnaissance mission of the planet ]). The technician is wearing a safety suit in overpressure with an external air supply.]]
	Many substituted hydrazines are known, and several occur naturally. Some examples include
			Hydrazine was first used as a component in ]s during ]. A 30% mix by weight with 57% ] (named ] in the German ]) and 13% water was called ] by the Germans.<ref name=Clark2018>{{cite book |isbn = 978-0-8135-9918-2 |title = Ignition!: An Informal History of Liquid Rocket Propellants |last1 = Clark |first1 = John Drury |author-link=John Drury Clark |date = 23 May 2018 |publisher = Rutgers University Press |url=https://books.google.com/books?id=BdU4DwAAQBAJ&q=C-Stoff |pages=302}}</ref> The mixture was used to power the ] rocket-powered fighter plane, in which the German ] '']'' was used as an oxidizer. Unmixed hydrazine was referred to as ] by the Germans, a designation also used later for the ethanol/water fuel for the ].<ref>{{cite report |author1=T. W. Price|author2=D. D. Evans|date= |title=Technical Report 32-7227 The Status of Monopropellant Hydrazine Technology| url=https://ntrs.nasa.gov/api/citations/19680006875/downloads/19680006875.pdf|publisher=National Aeronautics and Space Administration (NASA) |page=1|access-date=22 February 2022}}</ref>
	*], where one of the hydrogen atoms on the hydrazine molecule has been replaced with a methyl group (CH<sub>3</sub>). By the symmetry of the hydrazine molecule, it does not matter which hydrogen atom is replaced. It is sometimes used as a rocket fuel.
	*] (unsymmetrical dimethylhydrazine, UDMH) and ] (]) are hydrazines where two hydrogen atoms are replaced by ]s. UDMH is easier to manufacture than symmetrical dimethylhydrazine is, and UDMH is a fairly common rocket fuel.
	*] and ] are hydrazine derivatives found in the commercially produced mushroom species '']''. ] is metabolized into monomethyl hydrazine.
	*], ], ], and ] are ]s whose molecules contain hydrazine-like structures.
	*] (2,4-DNPH) is commonly used to test for ] and ] in ].
	*], C<sub>6</sub>H<sub>5</sub>NHNH<sub>2</sub>, the first hydrazine to be discovered.
			Hydrazine is used as a low-power ] for the maneuvering (RCS/Reaction control system) thrusters of spacecraft, and was used to power the ]'s auxiliary power units (APUs). In addition, mono-propellant 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 Mars landers '']'' (May 2008), '']'' (August 2012), and '']'' (February 2021).
	==Applications==
	The majority use of hydrazine is as a precursor to ]s. Specific compounds include ] and ], which yield 100-200 mL of gas per gram of precursor. In a related application, ], the gas-forming agent in ], is produced from hydrazine by reaction with ].<ref name=Ullmann/>
			During the ], ] (also discovered by Fischer in 1875) was used instead of hydrazine. Together with nitric oxidizers it became known as "]" due to its highly dangerous nature.<ref>{{Cite web|url=http://www.spacesafetymagazine.com/space-disasters/nedelin-catastrophe/historys-launch-padfailures-nedelin-disaster-part-1/|title=The Nedelin Catastrophe, Part 1|date=28 October 2014|archive-url=https://archive.today/20220215233340/http://www.spacesafetymagazine.com/space-disasters/nedelin-catastrophe/historys-launch-padfailures-nedelin-disaster-part-1/|access-date=15 February 2022|archive-date=15 February 2022|url-status=live}}</ref>
	Hydrazine is also used as a propellant on board space vehicles, and to both reduce the concentration of dissolved oxygen in and control pH of water used in large industrial boilers. The ] fighter jet uses hydrazine to fuel the aircraft's emergency power unit.
			In all hydrazine mono-propellant engines, the hydrazine is passed over a ] such as ] metal supported by high-surface-area ] (aluminium oxide), which causes it to decompose into ] ({{chem2|NH3}}), nitrogen gas ({{chem2|N2}}), and hydrogen ({{chem2|H2}}) gas according to the three following reactions:<ref name="Haws">{{cite journal|vauthors=Haws JL, Harden DG|date=1965|title=Thermodynamic Properties of Hydrazine|journal= Journal of Spacecraft and Rockets |volume=2|issue=6|pages=972–974|bibcode=1965JSpRo...2..972H|doi=10.2514/3.28327}}</ref>
	===Precursor to pesticides and pharmaceuticals===
	Hydrazine is a useful building block in ] of pharmaceuticals and pesticides. One example is ] and another is maleic hydrazide. The antitubercular drug ] is prepared from hydrazine.
			: Reaction 1:&emsp;{{chem2|N2H4 → N2 + 2 H2}}
	==Hydrazine in biology==
			: Reaction 2:&emsp;{{chem2|3 N2H4 → 4 NH3 + N2}}
	Hydrazine is the intermediate in the anaerobic oxidation of ammonia (anammox) process.<ref>Strous, M., and Jetten, M.S.M. (2004) Anaerobic oxidation of methane and ammonium. Ann Rev Microbiol 58: 99–117.</ref> It is produced by some yeasts and the open ocean bacterium anammox ('']'').<ref>{{cite news | author = Brian Handwerk | url = http://news.nationalgeographic.com/news/2005/11/1109_051109_rocketfuel.html | title = Bacteria Eat Human Sewage, Produce Rocket Fuel | publisher = ] |date=9 November 2005 | accessdate = 2007-11-12}}</ref>
			: Reaction 3:&emsp;{{chem2|4 NH3 + N2H4 → 3 N2 + 8 H2}}
			The first two reactions are extremely ] (the catalyst chamber can reach 800&nbsp;°C in a matter of milliseconds,<ref name="Vieira">{{cite journal|vauthors=Vieira R, Pham-Huu C, Kellera N, Ledouxa MJ|year=2002|title=New carbon nanofiber/graphite felt composite for use as a catalyst support for hydrazine catalytic decomposition|journal=]|volume=44|issue=9|pages=954–955|doi=10.1039/b202032g|pmid=12123065}}</ref>) and they produce large volumes of hot gas from a small volume of liquid,<ref name="Chen">{{cite journal|vauthors=Chen X, Zhang T, Xia L, Li T, Zheng M, Wu Z, Wang X, Wei Z, Xin Q, Li C|date=Apr 2002|title=Catalytic Decomposition of Hydrazine over Supported Molybdenum Nitride Catalysts in a Monopropellant Thruster|journal=]|volume=79|pages=21–25|doi=10.1023/A:1015343922044|s2cid=92094908}}</ref> making hydrazine a fairly efficient thruster propellant with a vacuum ] of about 220 seconds.<ref>{{Cite web|url=https://www.eso-io.com/my.logout.php3?errorcode=20|archive-url=https://web.archive.org/web/20080623224048/http://cs.astrium.eads.net/sp/SpacecraftPropulsion/MonopropellantThrusters.html|title=BIG-IP logout page|archive-date=June 23, 2008|website=www.eso-io.com|access-date=May 20, 2020}}</ref> Reaction 2 is the most exothermic, but produces a smaller number of molecules than that of reaction 1. Reaction 3 is ] and reverts the effect of reaction 2 back to the same effect as reaction 1 alone (lower temperature, greater number of molecules). The catalyst structure affects the proportion of the {{chem2|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.<ref>{{Cite journal |last1=Valera-Medina |first1=A |last2=Xiao |first2=H |last3=Owen-Jones |first3=M |last4=David |first4=W. I. F. |last5=Bowen |first5=P. J. |date=2018-11-01 |title=Ammonia for power |journal=Progress in Energy and Combustion Science |language=en|volume=69 |pages=63–102 |doi=10.1016/j.pecs.2018.07.001 |s2cid=106214840 |issn=0360-1285|doi-access=free|bibcode=2018PECS...69...63V }}</ref>
	==Organic chemistry==
	Hydrazines are part of many ], often those of practical significance in ]s, such as the antituberculosis medication ] and the antifungal ], as well as in textile ]s and in photography.<ref name=Ullmann/>
			Since hydrazine is a solid below 2&nbsp;°C, it is not suitable as a general purpose rocket propellant for military applications. Other ] that are used as rocket fuel are ], {{chem2|CH3NHNH2}}, also known as MMH (melting point −52&nbsp;°C), and ], {{chem2|(CH3)2NNH2}}, also known as UDMH (melting point −57&nbsp;°C). These derivatives are used in two-component rocket fuels, often together with ], {{chem2|N2O4}}. A 50:50 mixture by weight of hydrazine and UDMH was used in the engine of the service propulsion system of the ], both the ascent and descent engines of the ] and ] ] and is known as ].<ref name=Clark2018/> These reactions are extremely exothermic, and the burning is also ] (it starts burning without any external ignition).<ref name="Mitchell">{{cite journal |vauthors=Mitchell MC, Rakoff RW, Jobe TO, Sanchez DL, Wilson B |date=2007 |title=Thermodynamic analysis of equations of state for the monopropellant hydrazine |journal= Journal of Thermophysics and Heat Transfer |volume=21 |issue=1 |pages=243–246 |doi=10.2514/1.22798}}</ref>
	===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 afford the hydrazone:<ref>{{OrgSynth | author = Day, A. C.; Whiting, M. C. | title = Acetone Hydrazone | collvol = 6 | collvolpages = 10 | prep = cv6p0010}}</ref>
	:2 (CH<sub>3</sub>)<sub>2</sub>CO + N<sub>2</sub>H<sub>4</sub> → 2 H<sub>2</sub>O + <sub>2</sub>
	:<sub>2</sub> + N<sub>2</sub>H<sub>4</sub> → 2 (CH<sub>3</sub>)<sub>2</sub>C=NNH<sub>2</sub>
	The propanone azine is an intermediate in the Atofina-PCUK synthesis. Direct ] of hydrazines with ] in the presence of base affords alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on level of substitution (same as in ordinary ]s). The reduction of ]s to hydrazines present a clean way to produce 1,1-dialkylated hydrazines.
			There are ongoing efforts in the aerospace industry to find a replacement for hydrazine, given its potential ban across the European Union.<ref>{{Cite web |date=2017-10-25 |title=Hydrazine ban could cost Europe's space industry billions |url=https://spacenews.com/hydrazine-ban-could-cost-europes-space-industry-billions/ |access-date=2022-08-19 |website=SpaceNews |language=en-US}}</ref><ref>{{Cite web |title=International research projects {{!}} Ministry of Business, Innovation & Employment |url=https://www.mbie.govt.nz/science-and-technology/space/nzspacetalk/international-research-projects/ |access-date=2022-08-19 |website=www.mbie.govt.nz}}</ref><ref>{{Cite web |last=Urban |first=Viktoria |date=2022-07-15 |title=Dawn Aerospace granted €1.4 million by EU for green propulsion technology |url=https://spacewatch.global/2022/07/dawn-aerospace-granted-e1-4-million-by-eu-for-green-propulsion-technology/ |access-date=2022-08-19 |website=SpaceWatch.Global |language=en-US}}</ref> Promising alternatives include ]-based propellant combinations, with development being led by commercial companies ], ],<ref>{{Cite web |last=Berger |first=Eric |date=2022-07-19 |title=Two companies join SpaceX in the race to Mars, with a launch possible in 2024 |url=https://arstechnica.com/science/2022/07/relativity-and-impulse-space-say-theyre-flying-to-mars-in-late-2024/ |access-date=2022-08-19 |website=Ars Technica |language=en-us}}</ref> and ].<ref>{{Cite web |date=2021-06-15 |title=Launcher to develop orbital transfer vehicle |url=https://spacenews.com/launcher-to-develop-orbital-transfer-vehicle/ |access-date=2022-08-19 |website=SpaceNews |language=en-US}}</ref> The first nitrous oxide-based system ever flown in space was by ] onboard their ] in 2021, using six Dawn Aerospace B20 thrusters.<ref>{{Cite web |title=Dawn Aerospace validates B20 Thrusters in space – Bits&Chips |date=6 May 2021 |url=https://bits-chips.nl/artikel/dawn-aerospace-validates-b20-thrusters-in-space/ |access-date=2022-08-19 |language=en-US}}</ref><ref>{{Cite web |title=Dawn B20 Thrusters Proven In Space |url=https://www.dawnaerospace.com/latest-news/b20-thrusters-proven-in-space |access-date=2022-08-19 |website=Dawn Aerospace |language=en-US}}</ref>
	In a related reaction, 2-cyano]s react with hydrazine to form amide hydrazides, which can be converted using 1,2-diketones into ].
			== Occupational hazards ==
	===Wolff-Kishner reduction===
			=== Health effects ===
	Hydrazine is used in the ], a reaction that transforms the ] group of a ] or ] into a ] (or ]) group via a ] intermediate. The production of the highly stable ] from the hydrazine derivative helps to drive the reaction.
			Potential routes of hydrazine exposure include dermal, ocular, inhalation and ingestion.<ref name=":3">{{Cite web |url=https://www.cdc.gov/niosh/docs/81-123/pdfs/0329.pdf |title=Occupational Safety and Health Guideline for Hydrazine—Potential Human Carcinogen |date=1988 |website=]|access-date=23 Nov 2018}}</ref>
			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.<ref name=":3" /><ref name=":2">{{Cite web |url=https://www.epa.gov/sites/production/files/2016-09/documents/hydrazine.pdf |title=Hydrazine 302-01-2 |website=] |access-date=23 Nov 2018}}</ref> Hydrazine is documented as a strong skin sensitizer with potential for cross-sensitization to hydrazine derivatives following initial exposure.<ref name=":4">{{Cite web |url=http://www.inchem.org/documents/hsg/hsg/hsg056.htm |title=International Programme on Chemical Safety—Health and Safety Guide No. 56—Hydrazine |date=1991 |website=IPCS INCHEM |publisher=] |location=Geneva |access-date=24 Nov 2018}}</ref> In addition to occupational uses reviewed above, exposure to hydrazine is also possible in small amounts from tobacco smoke.<ref name=":2" />
	===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 ].<ref>{{OrgSynth | author = Wiley, R. H.; Hexner, P. E. | title = 3,5-Dimethylpyrazole | collvol = 4 | collvolpages = 351 | prep = cv4p0351}}</ref> In the ] hydrazines react with imides to give ]s.
			The official U.S. guidance on hydrazine as a carcinogen is mixed but generally there is recognition of potential cancer-causing effects. The ] lists it as a "potential occupational carcinogen". The National Toxicology Program (NTP) finds it is "reasonably anticipated to be a human carcinogen". The ] 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".<ref name=":5">{{Cite web |url=https://www.osha.gov/chemicaldata/chemResult.html?recNo=347 |title=Occupational Chemical Database—Hydrazine |website=www.osha.gov |publisher=] |access-date=24 Nov 2018}}</ref>
	===Sulfonation===
	Being a good nucleophile, N<sub>2</sub>H<sub>4</sub> can attack sulfonyl halides and acyl halides.<ref>{{OrgSynth | author = Friedman, L; Litle, R. L.; Reichle, W. R. | title = ''p''-Toluenesulfonyl Hydrazide | collvol = 5 | collvolpages = 1055 | prep = cv5p1055}}</ref> The ]hydrazine also forms hydrazones upon treatment with carbonyls.
			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.<ref name=":03">{{Cite web |url=https://monographs.iarc.fr/wp-content/uploads/2018/06/mono115-06.pdf |title=Hydrazine |date=Jun 2018 |publisher=] |access-date=23 Nov 2018 |archive-date=26 November 2020 |archive-url=https://web.archive.org/web/20201126130626/https://monographs.iarc.fr/wp-content/uploads/2018/06/mono115-06.pdf }}</ref> Based on cohort and cross-sectional studies of occupational hydrazine exposure, a committee from the ], 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.<ref>{{Cite book |title=Gulf War and Health: Fuels, Combustion Products, and Propellants |last=Institute of Medicine |publisher=The National Academies Press |year=2005 |isbn=978-0-309-09527-3 |volume=3 |location=Washington, DC |page=347 |chapter=Ch. 9: Hydrazines and Nitric Acid |doi=10.17226/11180 |s2cid=228274601 }}</ref> The ]'s ] (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.<ref>{{Cite web |url=http://ec.europa.eu/social/BlobServlet?docId=6516&langId=en |title=Recommendation from the Scientific Committee on Occupational Exposure Limits for Hydrazine |date=Aug 2010 |website=European Commission |format=PDF|access-date=23 Nov 2018}}</ref>
	===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 ].<ref>{{OrgSynth | author = Weinshenker, N. M.; Shen, C. M.; Wong, J. Y. | title = Polymeric carbodiimide | collvol = 6 | collvolpages = 951 | year = 1988 | prep = cv6p0951}}</ref>
			In the event of a hydrazine exposure-related emergency, ] 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. ] also recommends anyone with potential hydrazine exposure to seek medical attention as soon as possible.<ref name=":3" /> 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 ] (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 (]) treatment.<ref name=":4" />
	===Reducing agent===
	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.
			=== Occupational exposure limits ===
	===Hydrazinium salts===
			* ] Recommended Exposure Limit (REL): 0.03 ] (0.04&nbsp;mg/m<sup>3</sup>) 2-hour ceiling<ref name=":5" />
	Hydrazine is converted to solid salts by treatment with mineral acids. A common salt is ], HSO<sub>4</sub>, called hydrazinium sulfate.<ref></ref> Hydrazine sulfate was investigated as a treatment of cancer-induced ], but proved ineffective.<ref>{{cite journal |doi=10.2165/00003495-199855050-00005 |author=Gagnon B, Bruera E |title=A review of the drug treatment of cachexia associated with cancer |journal=Drugs |volume=55 |issue=5 |pages=675–88 |year=1998 |month=May |pmid=9585863}}</ref>
			* ] Permissible Exposure Limit (PEL): 1 ppm (1.3&nbsp;mg/m<sup>3</sup>) 8-hour Time Weighted Average<ref name=":5" />
			* ] Threshold Limit Value (TLV): 0.01 ppm (0.013&nbsp;mg/m<sup>3</sup>) 8-hour Time Weighted Average<ref name=":5" />
			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.<ref name=":12">{{Cite web |url=https://nj.gov/health/eoh/rtkweb/documents/fs/1006.pdf |title=Hazardous Substance Fact Sheet—Hydrazine |date=Nov 2009 |website=New Jersey Department of Public Health |access-date=23 Nov 2018}}</ref>
	Hydrazine azide (N<sub>5</sub>H<sub>5</sub>), the salt of hydrazine and ], was of scientific interest, because of its high nitrogen content and explosive properties. Structurally, it is {{chem||+||-}}. It decomposes explosively into hydrazine, ammonia and nitrogen gas:<ref>{{cite book
	| title = Thermal decomposition and combustion of explosives and propellants
	| author = G. B. Manelis
	| publisher = CRC Press
	| year = 2003
	| isbn = 0415299845
	| page = 235
	}}</ref>
			For aerospace personnel, the ] uses an emergency exposure guideline, developed by the ] 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.<ref name=":6">{{Cite web |url=https://webapp1.dlib.indiana.edu/virtual_disk_library/index.cgi/821003/FID177/pubs/af/48/afoshstd48-8/afoshstd48-8.pdf |title=Air Force Occupational Safety and Health (AFOSH) Standard 48-8 |date=1 Sep 1997 |website=] |access-date=23 Nov 2018}}</ref>
	:12 {{chem|N|5|H|5}} &rarr; 3 {{chem|N|2|H|4}} + 16 {{chem|NH|3}} + 19 {{chem|N|2}}
			=== Handling and medical surveillance ===
	Reaction of {{chem|N|5|H|5}} with sulfuric acid gives quantitative yields of pure hydrazine sulfate and hydrazoic acid.<ref>{{cite doi|10.1016/0277-5387(95)00527-7}}</ref>
			A complete surveillance programme for hydrazine should include systematic analysis of biologic monitoring, medical screening and morbidity/mortality information. The ] 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.<ref name=":3" />
			Common controls used for hydrazine include process enclosure, local exhaust ventilation and ] (PPE).<ref name=":3" /> Guidelines for hydrazine PPE include non-permeable gloves and clothing, indirect-vent splash resistant goggles, face shield and in some cases a respirator.<ref name=":12" /> 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 ] guidelines should be implemented.<ref name=":3"/>
	==Other industrial uses==
	Hydrazine is used in many processes including: production of ] fibers, as a ] ]; in ]s, ] ]; and ]s, as a ] in ] polymerizations, and heat stabilizers. In addition, a semiconductor deposition technique using hydrazine has recently been demonstrated, with possible application to the manufacture of ]s used in ]s. Hydrazine in a 70% hydrazine, 30% water solution is used to power the EPU (]) on the ] ] fighter plane. The explosive ] is made by combining hydrazine with ].
			For ] 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.<ref name=":6" /> USAF bases requiring the use of hydrazine generally have specific base regulations governing local requirements for safe hydrazine use and emergency response.
	Hydrazine is often used as an oxygen scavenger and ] in boiler water treatment. However due to the toxicity and certain undesired effects, namely increased rates of ] (FAC){{Citation needed|date=March 2010}}, this practice is discouraged.
	===Rocket fuel===		==Molecular structure==
			Hydrazine, {{chem2|H2N\sNH2}}, contains two amine groups {{chem2|NH2}} connected by a single bond between the two nitrogen atoms. Each {{chem2|N\sNH2}} subunit is pyramidal. The structure of the free molecules was determined by ] and ]. The N–N single bond length is 1.447(2) ] (144.7(2) ]), the N-H distance is 1.015(2) ], the N-N-H angles are 106(2)° and 112(2)°, the H-N-H angle is 107°.<ref>{{Cite journal |last1=Kohata |first1=Kunio |last2=Fukuyama |first2=Tsutomu |last3=Kuchitsu |first3=Kozo |date=March 1982 |title=Molecular structure of hydrazine as studied by gas electron diffraction |journal=The Journal of Physical Chemistry |volume=86 |issue=5 |pages=602–606 |doi=10.1021/j100394a005 |issn=0022-3654}}</ref> The molecule adopts a ] with a torsion angle of 91(2)° (dihedral angle between the planes containing the N-N bond and the bisectors of the H-N-H angles). The ] is twice that of ]. These structural properties resemble those of gaseous ], which adopts a "skewed" ] conformation, and also experiences a strong rotational barrier.
	Hydrazine was first used as a ] during ] for the ] (the first rocket-powered fighter plane), under the code name '''B-Stoff''' (hydrazine ]). When mixed with ] (]) and water it was called ].
			The structure of solid hydrazine was determined by X-ray diffraction. In this phase the N-N bond has a length of 1.46 ] and the nearest non-bonded distances are 3.19, 3.25 and 3.30 ].<ref>{{Cite journal |last1=Collin |first1=R. L. |last2=Lipscomb |first2=W. N. |date=1951-01-01 |title=The crystal structure of hydrazine |journal=Acta Crystallographica |volume=4 |issue=1 |pages=10–14 |doi=10.1107/s0365110x51000027 |issn=0365-110X|doi-access=free |bibcode=1951AcCry...4...10C }}</ref>
	Hydrazine is also used as a low-power ] for the maneuvering thrusters of spacecraft, and the ]'s auxiliary power units (APUs). In addition, monopropellant hydrazine-fueled rocket engines are often used in terminal descent of spacecraft. A collection of such engines was used in both ] landers as well as the ] lander launched in August 2007.
			==Synthesis and production==
	In all hydrazine monopropellant engines, the hydrazine is passed by a ] such as ] metal supported by high-surface-area ] (aluminium oxide) or ]s,<ref name="Vieira">{{cite journal | last = Vieira | first = R. | coauthors = C. Pham-Huu, N. Keller and M. J. Ledoux | year = 2002 | title = New carbon nanofiber/graphite felt composite for use as a catalyst support for hydrazine catalytic decomposition | journal = ] | issue = 9 | pages = 954–955 | doi = 10.1039/b202032g}}</ref> or more recently ] on alumina,<ref name="Chen">{{cite journal | last = Chen | first = Xiaowei | coauthors = ''et al.'' | year = 2002 | month = April | title = Catalytic Decomposition of Hydrazine over Supported Molybdenum Nitride Catalysts in a Monopropellant Thruster | journal = ] | volume = 79 | pages = 21&ndash;25 | doi = 10.1023/A:1015343922044 }}</ref> which causes it to decompose into ], nitrogen gas, and hydrogen gas according to the following reactions:
			Diverse synthetic pathways for hydrazine production have been developed.<ref name="Ullmann">{{Ullmann|doi=10.1002/14356007.a13_177 |title=Hydrazine |year=2001 |last1=Schirmann |first1=Jean-Pierre |last2=Bourdauducq |first2=Paul |isbn=3-527-30673-0}}</ref> The key step is the creation of the ]–N single bond. The many routes can be divided into those that use chlorine oxidants (and generate salt) and those that do not.
			===Oxidation of ammonia via oxaziridines from peroxide===
	#3 N<sub>2</sub>H<sub>4</sub> → 4 NH<sub>3</sub> + N<sub>2</sub>
			Hydrazine can be synthesized from ammonia and hydrogen peroxide with a ketone catalyst, in a procedure called the ] (sometimes called Pechiney-Ugine-Kuhlmann process, the Atofina–PCUK cycle, or ketazine process).<ref name="Ullmann"/> The net reaction is:<ref>{{Cite book |url=https://www.elsevier.com/books/chemistry-of-petrochemical-processes/matar-ph-d/978-0-88415-315-3 |title=Chemistry of Petrochemical Processes |last1=Matar |first1=Sami |last2=Hatch |first2=Lewis F. |date=2001 |publisher=Gulf Professional Publishing |isbn=978-1-4933-0346-5 |edition=2nd |location=Burlington |page=148 |oclc=990470096 |via=Elsevier}}</ref>
	#N<sub>2</sub>H<sub>4</sub> → N<sub>2</sub> + 2 H<sub>2</sub>
	#4 NH<sub>3</sub> + N<sub>2</sub>H<sub>4</sub> → 3 N<sub>2</sub> + 8 H<sub>2</sub>
			:{{chem2|2 NH3 + H2O2 → N2H4 + 2 H2O}}
	These reactions are extremely ] (the catalyst chamber can reach 800 °C in a matter of milliseconds,<ref name="Vieira" />) and they produce large volumes of hot gas from a small volume of liquid hydrazine,<ref name="Chen" /> making it a fairly efficient thruster propellant with a vacuum ] of about 220 seconds.<ref></ref>
			In this route, the ketone and ammonia first condense to give the ], which is oxidised by hydrogen peroxide to the ], a three-membered ring containing carbon, oxygen, and nitrogen. Next, the oxaziridine gives the ] by ], which process creates the nitrogen-nitrogen single bond. This hydrazone condenses with one more equivalent of ketone.
	Hydrazine is also used in ] aircraft to power the EPU (emergency power unit). It is a small generator that supplies emergency hydraulic or electric power in the event that main power is lost in the aircraft.
			:]
			The resulting ] is hydrolyzed to give hydrazine and regenerate the ketone, ]:
			:{{chem2|](])C\dN\sN\dC(Et)Me + 2 H2O → 2 Me(Et)C\dO + N2H4}}
			Unlike most other processes, this approach does not produce a salt as a by-product.<ref>{{Cite book |chapter-url=https://www.academia.edu/9511336 |title=Riegel's handbook of industrial chemistry |last1=Riegel |first1=Emil Raymond |last2=Kent |first2=James Albert |date=2003 |publisher=Springer Science & Business Media |isbn=978-0-306-47411-8 |edition=10th |location=New York |page=192 |chapter=Hydrazine |oclc=55023601 }}</ref>
	Other variants of hydrazine that are used as rocket fuel are ], (CH<sub>3</sub>)NH(NH<sub>2</sub>) (also known as MMH) and ], (CH<sub>3</sub>)<sub>2</sub>N(NH<sub>2</sub>) (also known as UDMH). These derivatives are used in two-component rocket fuels, often together with ], N<sub>2</sub>O<sub>4</sub>, sometimes known as ]. This reaction is extremely exothermic, as a rocket fuel must be, and the burning is also ], which means that the burning starts without any external ignition source.
	===Fuel cells===		===Chlorine-based oxidations===
			The ], first announced in 1907, produces hydrazine from ] (the active ingredient in many ]es) and ammonia without the use of a ketone catalyst. This method relies on the reaction of ] with ] to create the ]–N ] as well as a ] byproduct:<ref name="OrgSynth">{{cite journal |vauthors=Adams R, Brown BK |year=1922 |title=Hydrazine Sulfate |journal=] |volume=2 |page=37 |doi=10.15227/orgsyn.002.0037 |s2cid=221547391 }}</ref>
	The Italian catalyst manufacturer ] has proposed using hydrazine as an alternative to ] in ]s. The chief benefit of using hydrazine is that it can produce over 200 m]/cm<sup>2</sup> more than a similar hydrogen cell without the need to use expensive ] 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 ]-] ], the fuel reacts and forms a safe solid called ]. By then flushing the tank with warm water, the liquid hydrazine hydrate is released. Hydrazine has a higher ] of 1.56 ] compared to 1.23 V for hydrogen. Hydrazine breaks down in the cell to form ] and ] which bonds with oxygen, releasing water.<ref name="The Engineer"></ref>
			:{{chem2|NH2Cl + NH3 → N2H4 + HCl}}
	Hydrazine was used in fuel cells manufactured by ], including some that provided electric power in space satellites in the 1960s.
			Related to the Raschig process, ] can be oxidized instead of ammonia. Again sodium hypochlorite serves as the oxidant. The net reaction is shown:<ref>{{cite web |url=http://chemindustry.ru/Hydrazine.php |title=Hydrazine: Chemical product info |website=chemindustry.ru |archive-url=https://web.archive.org/web/20180122212817/http://chemindustry.ru/Hydrazine.php |archive-date=22 January 2018 |access-date=8 Jan 2007}}</ref>
			:{{chem2|(NH2)2CO + NaOCl + 2 NaOH → N2H4 + H2O + NaCl + Na2CO3}}
			The process generates significant by-products and is mainly practised in Asia.<ref name="Ullmann"/>
	===Gun Propellant===
	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 notable for being one of the most predictable and stable, with a remarkably 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 pressures, sometimes including catastrophic tube failures (explosions).<ref>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 Laboratory, March 1993 At 2011-7-23</ref>
			The ] 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.<ref name="Ullmann"/>
	==Hazards==
	Hydrazine is highly toxic and dangerously unstable, especially in the ] form. According to the ]:<blockquote>
	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.<ref name="EPA">]. ''Hydrazine Hazard Summary-Created in April 1992; Revised in January 2000''. Retrieved on February 21, 2008.</ref>
	</blockquote>
			==Reactions==
	Limit tests for hydrazine in pharmaceuticals suggest that it should be in the low ppm range.<ref name="EuroP">]. ''Acceptance criteria for levels of hydrazine in substances for pharmaceutical use and analytical methods for its determination''. Retrieved on April 22, 2008.</ref>
			===Acid-base behavior===
	Hydrazine may also cause ].<ref>PHM 450 Course, Spring 2009, Michigan State University</ref>
			]
	At least one human is known to have died, after 6 months of sublethal exposure to hydrazine hydrate.<ref>International Programme on Chemical Safety, , Section 9.2.1, dated 1987. Retrieved on February 21, 2008.</ref>
			Hydrazine forms a ] {{chem2|N2H4*H2O}} that is denser (1.032 g/cm<sup>3</sup>) than the ] form {{chem2|N2H4}} (1.021 g/cm<sup>3</sup>). Hydrazine has ] (]) chemical properties comparable to those of ]:<ref>{{cite book |title = Handbook of Chemistry and Physics |edition = 83rd |publisher = CRC Press |date = 2002}}</ref>
			:{{chem2|N2H4 + H2O → + + OH-}}, ''K''<sub>b</sub> = 1.3 × 10<sup>−6</sup>, p''K''<sub>b</sub> = 5.9
			(for ammonia ''K''<sub>b</sub> = 1.78 × 10<sup>−5</sup>)
	On February 21, 2008, the United States government destroyed the disabled spy satellite ] with a sea-launched missile, reportedly due to the potential danger of a hydrazine release if it re-entered the Earth's atmosphere intact.<ref>{{cite web|url=http://spectrum.ieee.org/aug08/6533|title=IEEE Spectrum Online. U.S. Satellite Shootdown|accessdate=2008-08-08}}</ref>
			It is difficult to diprotonate:<ref>{{Cite book |title=Inorganic chemistry |vauthors=Holleman AF, Wiberg E, Wiberg N|date=2001 |publisher=Academic Press |isbn=978-0-12-352651-9 |edition=1st Eng. |location=San Diego |oclc=813400418}}</ref>
			:{{chem2|+ + H2O → (2+) + OH-}}, ''K''<sub>b</sub> = 8.4 × 10<sup>−16</sup>, p''K''<sub>b</sub> = 15
			Exposure to extremely strong bases or alkali metals generates deprotonated hydrazide salts. Most explode on exposure to air or moisture.<ref>{{Kirk-Othmer|title=Hydrazine and its derivatives|year=2004|author=Eugene&nbsp;F. Rothgery|doi=10.1002/0471238961.0825041819030809.a01.pub2}} </ref>
			===Redox reactions===
			Ideally, the combustion of hydrazine in oxygen produces nitrogen and water:
			:{{chem2|N2H4 + O2 → N2 + 2 H2O}}
			An excess of oxygen gives oxides of nitrogen, including ] and ]:
			:{{chem2|N2H4 + 2 O2 → 2 NO + 2 H2O}}
			:{{chem2|N2H4 + 3 O2 → 2 NO2 + 2 H2O}}
			The heat of combustion of hydrazine in oxygen (air) is 19.41 MJ/kg (8345 BTU/lb).<ref>{{cite web |url=http://cameochemicals.noaa.gov/chris/HDZ.pdf |title=Hydrazine—Chemical Hazard Properties Table |date=1999 |website=NOAA.gov}}</ref>
			Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. This property makes it useful as an ], an oxygen ], and a ] in water boilers and heating systems. It also directly reduces salts of less active metals (e.g., bismuth, arsenic, copper, mercury, silver, lead, platinum, and palladium) to the element.<ref>{{cite book|url=https://archive.org/details/cftri.2662nonaqueoussolven0000ludw/page/133/|page=133|title=Non-aqueous solvents|first1=Ludwig F.|last1=Audrieth|first2=Jacob|last2=Kleinberg|publisher=John Wiley & Sons|location=New York|year=1953|lccn=52-12057}}</ref> That property has commercial application in ] ] plating and ] extraction from ]. Some colour photographic processes also use a weak solution of hydrazine as a stabilising wash, as it scavenges ] and unreacted silver halides. Hydrazine is the most common and effective reducing agent used to convert ] (GO) to reduced graphene oxide (rGO) via hydrothermal treatment.<ref>{{cite journal |vauthors=Stankovich S, Dikin DA, Piner RD, Kohlhaas KA, Kleinhammes A, Jia Y, Wu Y, Nguyen ST, Ruoff RS |date=2007 |title=Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide |journal=] |volume=45 |issue=7 |pages=1558–1565 |doi=10.1016/j.carbon.2007.02.034|bibcode=2007Carbo..45.1558S |s2cid=14548921 }}</ref>
			===Hydrazinium salts===
			Hydrazine can be ] to form various solid salts of the ] cation {{chem2|+}}, by treatment with mineral acids. A common salt is ], {{chem2|+-}}.<ref>{{cite web |url=http://hazard.com/msds/mf/baker/baker/files/h3633.htm |title=HYDRAZINE SULFATE |website=hazard.com |access-date=22 Jan 2019}}</ref> Hydrazinium hydrogensulfate was investigated as a treatment of cancer-induced ], but proved ineffective.<ref>{{cite journal |vauthors=Gagnon B, Bruera E |date=May 1998 |title=A review of the drug treatment of cachexia associated with cancer |journal=] |volume=55 |issue=5 |pages=675–88 |doi=10.2165/00003495-199855050-00005 |pmid=9585863 |s2cid=22180434}}</ref>
			Double protonation gives the hydrazinium ] or hydrazinediium, {{chem2|(2+)}}, of which various salts are known.<ref>{{cite web |url=http://www.easychem.org/en/subst-ref/?id=3969 |title=Diazanediium |website=CharChem |access-date=22 Jan 2019}}</ref>
			===Organic chemistry===
			Hydrazines are part of many ], often those of practical significance in ]s (see applications section), as well as in textile ]s and in photography.<ref name=Ullmann/>
			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.
			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 ].<ref>{{Cite journal |vauthors=Wiley RH, Hexner PE |date=1951 |title=3,5-Dimethylpyrazole |journal=] |volume=31 |page=43 |doi=10.15227/orgsyn.031.0043}}</ref> In the ] hydrazines react with imides to give ]s.
			Being a good nucleophile, {{chem2|N2H4}} can attack sulfonyl halides and acyl halides.<ref>{{Cite journal |vauthors=Friedman L, Litle RL, Reichle WR |date=1960 |title=p-Toluenesulfonyl Hydrazide |journal=] |volume=40 |page=93 |doi=10.15227/orgsyn.040.0093}}</ref> The ]hydrazine also forms hydrazones upon treatment with carbonyls.
			Hydrazine is used to cleave ''N''-alkylated phthalimide derivatives. This scission reaction allows phthalimide anion to be used as amine precursor in the ].<ref>{{Cite journal |vauthors=Weinshenker NM, Shen CM, Wong JY |date=1977 |title=Polymeric Carbodiimide. Preparation |journal=] |volume=56 |page=95 |doi=10.15227/orgsyn.056.0095}}</ref>
			====Hydrazone formation====
			Illustrative of the condensation of hydrazine with a simple carbonyl is its reaction with acetone to give the ]. The latter reacts further with hydrazine to yield ]:<ref>{{Cite journal |vauthors=Day AC, Whiting MC |date=1970 |title=Acetone Hydrazone |journal=Organic Syntheses |volume=50 |page=3 |doi=10.15227/orgsyn.050.0003}}</ref>
			:{{chem2|2 (CH3)2CO + N2H4 → 2 H2O + ((CH3)2C\dN)2}}
			:{{chem2|((CH3)2C\dN)2 + N2H4 → 2 (CH3)2C\dNNH2}}
			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 ]s). The reduction of ]s 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 ]s.
			===Biochemistry===
			Hydrazine is the intermediate in the anaerobic oxidation of ammonia (]) process.<ref>{{cite journal |vauthors=Strous M, Jetten MS |date=2004 |title=Anaerobic Oxidation of Methane and Ammonium |journal=] |volume=58 |pages=99–117 |doi=10.1146/annurev.micro.58.030603.123605 |pmid=15487931|hdl=2066/60186 |hdl-access=free }}</ref> It is produced by some yeasts and the open ocean bacterium anammox ('']'').<ref>{{cite news |url=http://www.wildsingapore.com/news/20051112/051109-5.htm |title=Bacteria Eat Human Sewage, Produce Rocket Fuel |last=Handwerk |first=Brian |date=9 Nov 2005 |access-date=12 Nov 2007 |publisher=] |via=Wild Singapore}}</ref>
			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 ] of an amino acid, and ].<ref>{{cite journal |vauthors=Hashida C, Hayashi K, Jie L, Haga S, Sakurai M, Shimizu H |date=1990 |title= |journal=Nippon Koshu Eisei Zasshi |language=ja |volume=37 |issue=6 |pages=400–5 |pmid=2132000}}</ref><ref>{{cite web |url=http://www.psms.org/sporeprints/sp338.html |title=Spore Prints #338 |veditors=Sieger AA |date=1 Jan 1998 |work=Bulletin of the Puget Sound Mycological Society |access-date=13 Oct 2008}}</ref>
			==In popular culture==
			In the fictional book ] (also adapted to a ]) the titular character uses an ] catalyst to separate ] gas from surplus hydrazine fuel, which he then burns to generate water for survival.
	== See also ==		== See also ==
			*{{annotated link|Nitrous oxide fuel blend}}
	*]
			*{{annotated link|USA-193}}
	* ]
	* ]
	* ]
	* ]
	== References ==		== References ==
	{{Reflist|colwidth=35em}}		{{Reflist}}
			== Further reading ==
			*{{Cite book |last=Schmidt |first=Eckart W. |title=Hydrazine and its derivatives: preparation, properties, applications |date=1984 |publisher=J. Wiley |isbn=978-0-471-89170-3 |location=New York}}
			*{{Cite book |last=Schmidt |first=Eckart W. |title=Hydrazine and its derivatives: preparation, properties, applications |date=2001 |publisher=Wiley-Interscience |isbn=978-0-471-41553-4 |edition=2nd |location=New York}}
			*{{Cite encyclopedia |title=Hydrazine |encyclopedia=Encyclopedia of Liquid Fuels |volume=4|publisher=De Gruyter |last=Schmidt |first=Eckart W. |date=2022 |pages=2587–3395 |doi=10.1515/9783110750287-025 |isbn=978-3-11-075028-7}}
			*{{Cite encyclopedia |title=Hydrazine Monopropellants |encyclopedia=Encyclopedia of Monopropellants |volume=1|publisher=De Gruyter |last=Schmidt |first=Eckart W. |date=2023 |pages=229–596 |doi=10.1515/9783110751390-005 |isbn=978-3-11-075139-0}}
	== External links ==		== External links ==
	{{wiktionary}}		{{wiktionary}}
	* &nbsp;&mdash; Robert Matunas		* {{snd}}Robert Matunas
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	{{Hydrazines}}		{{Hydrazines}}
			{{Nitrogen compounds}}
			{{Authority control}}
			{{Hydrides by group}}
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