| Revision as of 13:00, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463864355 of page Phthalonitrile for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:11, 9 October 2024 edit 193.62.199.211 (talk) ChEBI ID added to CHEMBOX identifiers |
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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 = 402529527 |
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| verifiedrevid = 464205947 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFile = 1,2-Dicyanobenzene.svg |
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| ImageFileL1 = 1,2-Dicyanobenzene.svg |
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| ImageSize = 140px |
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| ImageSizeL1 = 115 |
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| IUPACName = 1,2-dicyanobenzene, phthalonitrile |
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| ImageAltL1 = Skeletal formula |
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| OtherNames = phthalodinitrile, 1,2-benzenedicarbonitrile |
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| ImageFileR1 = Phthalonitrile-3D-spacefill.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSizeR1 = 125 |
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| ImageAltR1 = Space-filling model |
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| PIN = Benzene-1,2-dicarbonitrile<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 902 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| OtherNames = Phthalonitrile<ref name=iupac2013 /><br />Phthalodinitrile<br />1,2-Benzenedicarbonitrile<br />1,2-Dicyanobenzene |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6775 |
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| ChemSpiderID = 6775 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 91-15-6 |
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| CASNo = 91-15-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 978627YAJU |
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| PubChem = 7042 |
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| PubChem = 7042 |
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| ChEBI = 232056 |
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| SMILES = N#Cc1ccccc1C#N |
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| SMILES = N#Cc1ccccc1C#N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>4</sub>(CN)<sub>2</sub> |
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| Formula = C<sub>6</sub>H<sub>4</sub>(CN)<sub>2</sub> |
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| MolarMass = 128.13 g/mol |
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| MolarMass = 128.13 g/mol |
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| Appearance = Off-white crystals with lumps on the surface. |
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| Appearance = Off-white crystals with lumps on the surface. |
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| Density = |
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| Odor = Almond-like |
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| Density = 1.238 g/cm<sup>3</sup><ref name="ullmann"/> |
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| MeltingPt = 139 - 141 °C |
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| MeltingPtC = 139 to 141 |
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| BoilingPt = sublimes |
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'''Phthalonitrile''' is an organic compound with the formula C<sub>6</sub>H<sub>4</sub>(CN)<sub>2</sub>, which is an off-white crystal solid at room temperature. It is a derivative of ], containing two adjacent ] groups. The compound has low solubility in water but is soluble in common organic solvents. The compound is used as a precursor to ] and other pigments, fluorescent brighteners, and photographic sensitizers. |
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== Synthesis == |
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Phthalonitrile is produced industrially in a single-stage continuous process, by the ] of ] at 480 °C. The reaction is catalyzed by vanadium oxide-antimony-oxide in a ].<ref name="ullmann">Lorz, Peter M. "Phthalic Acid and Derivatives" in Ulmanns Encyclopedia of Industrial Chemistry. Wiley-VCH: Weinheim, 2002. {{doi|10.1002/14356007.a20_181.pub2}}.</ref> |
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Phthalonitrile was first described in 1896 by Johannes Pinnow. It was noted as a byproduct of the synthesis of ortho-dicyanodiazoamidobenzene via the reaction of ortho-amido] hydrochloride, ], and ].<ref>Pinnow, Johannes; Sämann, C. "Ueber Derivate des o-Amidobenzonitrils (Derivatives of Orthamidobenzonitrile)" Berichte der Deutschen Chemischen Gesellschaft 1896, volume 29 623-32. {{doi|10.1002/cber.189602901118}}</ref> The first intentional synthesis involved dehydration of phthalamide by boiling in ].<ref>Braun, A.; Tscherniac, J. "Über die Produkte der Einwirkung von Acetanhydrid auf Phthalamid (Products of the Action of Acetic Anhydride on Phthalamide)" Berichte der Deutschen Chemischen Gesellschaft 1907, volume 40, pp. 2709-14. {{doi|10.1002/cber.190704002202}}</ref> Another synthesis of historical interest is the ] in which an ortho substituted dihalobenzene is treated with copper(I) cyanide, which results in the halide groups being replaced by cyano groups.<ref>Karl M. Kadish, Kevin M. Smith, ]. The Porphyrin Handbook. 2003.</ref> |
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== Applications == |
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Phthalonitrile is the precursor to ] pigments, a very common organic pigment. Such pigments are generated through the reaction of phthalonitrile with various metal precursors. The reaction is carried out in a solvent at around 180 °C.<ref>{{cite encyclopedia|author=Löbbert, Gerd|chapter=Phthalocyanines|encyclopedia=Ullmann’s Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2000|doi=10.1002/14356007.a20_213|isbn=3527306730}}.</ref> |
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Ammonolysis of phthalonitrile gives to diimino]. This intermediate condensation with active methylene compounds to give commercially important ] and ]. |
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==References== |
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<references/> |
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{{Authority control}} |
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