| Revision as of 12:37, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 447622155 of page Tetrafluorohydrazine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:42, 23 December 2024 edit Trasheater Midir (talk | contribs)Extended confirmed users3,671 edits →Uses |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| verifiedrevid = 401623939 |
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| verifiedrevid = 470603940 |
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| ImageFile = Tetrafluorohydrazine-2D.png |
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| ImageFile = Tetrafluorohydrazine-2D.png |
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| ImageFile1 = Tetrafluorohydrazine-3D-balls.png |
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| ImageFile1 = Tetrafluorohydrazine-3D-vdW.png |
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| IUPACName = 1,1,2,2-tetrafluorohydrazine |
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| IUPACName = 1,1,2,2-tetrafluorohydrazine |
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| OtherNames = dinitrogen tetrafluoride, perfluorohydrazine, UN 1955 |
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| OtherNames = Tetrafluorohydrazine, perfluorohydrazine, UN 1955 |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| Abbreviations = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23228 |
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| ChemSpiderID = 23228 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GFADZIUESKAXAK-UHFFFAOYSA-N |
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| StdInChIKey = GFADZIUESKAXAK-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 10036-47-2 --> |
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| CASNo = 10036-47-2 |
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| EINECS = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = RR3J2QP9MG |
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| PubChem = 24845 |
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| PubChem = 24845 |
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| SMILES = FN(F)N(F)F |
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| SMILES = FN(F)N(F)F |
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| InChI = 1/F4N2/c1 |
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| InChI = 1/F4N2/c1 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = N<sub>2</sub>F<sub>4</sub> |
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| Formula = {{chem2|N2F4}} |
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| N=2|F=4 |
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| MolarMass = 104.01 g mol<sup>−1</sup> |
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| Appearance = |
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| Appearance = Colourless gas |
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| Density = |
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| MeltingPtC = −164.5 |
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| MeltingPt = −164.5 °C, 108.7 K<ref name="Greenwood&Earnshaw">{{Greenwood&Earnshaw}}</ref> |
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| MeltingPt_ref = <ref name="Greenwood&Earnshaw">{{Greenwood&Earnshaw}}</ref> |
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| BoilingPtC = −73 |
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| BoilingPt = −73 °C, 200 K<ref name="Greenwood&Earnshaw" /> |
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| BoilingPt_ref = <ref name="Greenwood&Earnshaw" />}} |
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| Section4 = {{Chembox Thermochemistry |
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| Section5 = {{Chembox Pharmacology |
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| Section7 = {{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| MainHazards = Explosion |
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| LD50 = 10 mL/kg (rat, intraperitoneal)<ref name="pubchem"/> |
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| LC50 = {{ubl|440 mg/m3 (mouse, inhalation)|900 ppm/1H (guinea pig, inhalation)}}<ref name="pubchem"/>}} |
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| Section8 = {{Chembox Related |
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'''Tetrafluorohydrazine''' or '''perfluorohydrazine''', {{chem2|N2F4|auto=1}}, is a colourless, nonflammable,<ref name="pubchem"/> reactive ] ]. It is a ] analog of ]. |
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==Synthesis== |
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Tetrafluorohydrazine was originally prepared from ] using a ] as a fluorine atom acceptor:<ref name=Ruff>{{cite journal |doi=10.1021/cr60250a004 |title=Derivatives of Nitrogen Fluorides |date=1967 |last1=Ruff |first1=John K. |journal=Chemical Reviews |volume=67 |issue=6 |pages=665–680 }}</ref> |
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:{{chem2|2NF3 + Cu -> N2F4 + CuF2}} |
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A number of F-atom acceptors can be used, including carbon, other metals, and ]. These reactions exploit the relatively weak N-F bond in NF<sub>3</sub>.<ref>{{cite book|page=82|title=Ignition!|first=John Drury|last=Clark|author-link=John Drury Clark|date=1972|publisher=Rutgers UP|location=New Brunswick, NJ|url=https://books.google.com/books?id=_JZcDwAAQBAJ|lccn=72-185390|isbn=0-8135-0725-1}}</ref> |
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== Properties == |
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Tetrafluorohydrazine is in equilibrium with its radical monomer ].<ref>{{cite book|last1=Jäger|first1=Susanne|url=https://books.google.com/books?id=rpfsCAAAQBAJ&pg=PA162|title=F Fluorine: Compounds with Oxygen and Nitrogen|last2=von Jouanne|first2=Jörn|last3=Keller-Rudek|first3=Hannelore|last4=Koschel|first4=Dieter|last5=Kuhn|first5=Peter|last6=Merlet|first6=Peter|last7=Rupecht|first7=Sigrid|last8=Vanecek|first8=Hans|last9=Wagner|first9=Joachim|date=1986|publisher=Springer|isbn=978-3-662-06341-5|editor1-last=Koschel|editor1-first=Dieter|series=Gmelin Handbook of Inorganic Chemistry|volume=4|location=Berlin|page=162|doi=10.1007/978-3-662-06339-2|access-date=29 August 2015|editor2-last=Kuhn|editor2-first=Peter|editor3-last=Merlet|editor3-first=Peter|editor4-last=Ruprecht|editor4-first=Sigrid|editor5-last=Wagner|editor5-first=Joachim}}</ref> |
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:{{chem2|N2F4 ⇌ 2 •NF2}} |
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At room temperature {{chem2|N2F4}} is mostly associated with only 0.7% in the form of {{chem2|NF2}} at 5mm Hg pressure. When the temperature rises to 225 °C, it mostly dissociates with 99% in the form of {{chem2|NF2}}.<ref name="bohn67">{{cite journal|last1=Bohn|first1=Robert K.|last2=Bauer|first2=Simon Harvey|date=February 1967|title=An electron diffraction study of the structures of NF<sub>2</sub> and N<sub>2</sub>F<sub>4</sub>|journal=Inorganic Chemistry|volume=6|issue=2|pages=304–309|doi=10.1021/ic50048a024}} molecule dimensions and angles</ref> |
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The energy needed to break the N−N bond in {{chem2|N2F4}} is 20.8 kcal/mol, with an entropy change of 38.6].<ref name="bohn67" /> For comparison, the dissociation energy of the N−N bond is {{convert|14.6|kcal/mol|abbr=on}} in ], {{convert|10.2|kcal/mol|abbr=on}} in ], and {{convert|60|kcal/mol|abbr=on}} in ]. The ] of {{chem2|N2F4}} (Δ<sub>f</sub>''H''°) is 34.421 kJ/mol.<ref>{{cite web|title=Nitrogen difluoride NF<sub>2</sub>(g)|url=http://www.chem.msu.su/rus/handbook/ivtan/100.html|website=www.chem.msu.su}}</ref> |
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==Uses== |
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Tetrafluorohydrazine is used in ] and some experimental ] formulations.<ref name="pubchem">{{cite web |title=Tetrafluorohydrazine |url=https://pubchem.ncbi.nlm.nih.gov/compound/Tetrafluorohydrazine |website=pubchem.ncbi.nlm.nih.gov |publisher=National Library of Medicine |access-date=26 March 2023 |language=en}}{{PD-notice}}</ref> It ] across ]s to give ] di(difluoroamine)s.{{sfn|Clark|1972|pp=167-168}} In ], as a precursor or a ]. It was considered for use as a high-energy liquid ] in some never-flown ] formulas in 1959.<ref> at DTIC.mil archived March 12, 2007</ref> |
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==Safety== |
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Tetrafluorohydrazine is a highly hazardous chemical that explodes in the presence of ] materials.<ref name="pubchem"/> |
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It is a toxic chemical which irritates skin, eyes and lungs. It is a ] and may cause ]. It may be fatal if inhaled or absorbed through skin. Vapors may be irritating and corrosive. It is a strong ]. Contact with this chemical may cause burns and severe injury. Fire produces irritating, corrosive and toxic gases. Vapors from ] are initially heavier than ] and spread across the ground.<ref name="pubchem"/> |
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Tetrafluorohydrazine explodes or ignites on contact with ] at ], including ], ], ], ], ], ], ], ], ]s, ], ], ] or powdered ]. Prolonged exposure of the container of tetrafluorohydrazine to high heat may cause it to rupture violently and rocket. Tetrafluorohydrazine itself can explode at high temperatures or with shock or blast when under pressure. When heated to decomposition in air, it emits highly toxic fumes of ] and ].<ref name="pubchem"/> |
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There is a fatal case in which during opening of valves to check the pressure, the cylinder exploded, killing one man and injuring another.<ref name="pubchem"/> |
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== References == |
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{{Reflist}} |
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{{fluorine compounds}} |
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{{Hydrazines}} |
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] |
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] |
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] |
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] |
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] |