Phthalonitrile is an organic compound with the formula C6H4(CN)2, which is an off-white crystal solid at room temperature. It is a derivative of benzene, containing two adjacent nitrile groups. The compound has low solubility in water but is soluble in common organic solvents. The compound is used as a precursor to phthalocyanine and other pigments, fluorescent brighteners, and photographic sensitizers.
Phthalonitrile is produced industrially in a single-stage continuous process, by the ammoxidation of o-xylene at 480 °C. The reaction is catalyzed by vanadium oxide-antimony-oxide in a fluidized bed reactor.[2]
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-amidobenzonitrile hydrochloride, sodium nitrite, and hydrochloric acid.[3] The first intentional synthesis involved dehydration of phthalamide by boiling in acetic anhydride.[4] Another synthesis of historical interest is the Rosenmund von Braun reaction in which an ortho substituted dihalobenzene is treated with copper(I) cyanide, which results in the halide groups being replaced by cyano groups.[5]
Applicationsedit
Phthalonitrile is the precursor to phthalocyanine 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.[6]
Ammonolysis of phthalonitrile gives to diiminoisoindoline. This intermediate condensation with active methylene compounds to give commercially important pigment yellow 185 and pigment yellow 139.
^ abLorz, Peter M. "Phthalic Acid and Derivatives" in Ulmanns Encyclopedia of Industrial Chemistry. Wiley-VCH: Weinheim, 2002. doi:10.1002/14356007.a20_181.pub2.
^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
^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
^Karl M. Kadish, Kevin M. Smith, Roger Guilard. The Porphyrin Handbook. 2003.
phthalonitrile, organic, compound, with, formula, c6h4, which, white, crystal, solid, room, temperature, derivative, benzene, containing, adjacent, nitrile, groups, compound, solubility, water, soluble, common, organic, solvents, compound, used, precursor, pht. Phthalonitrile is an organic compound with the formula C6H4 CN 2 which is an off white crystal solid at room temperature It is a derivative of benzene containing two adjacent nitrile groups The compound has low solubility in water but is soluble in common organic solvents The compound is used as a precursor to phthalocyanine and other pigments fluorescent brighteners and photographic sensitizers Phthalonitrile Names Preferred IUPAC name Benzene 1 2 dicarbonitrile 1 Other names Phthalonitrile 1 Phthalodinitrile1 2 Benzenedicarbonitrile1 2 Dicyanobenzene Identifiers CAS Number 91 15 6 Y 3D model JSmol Interactive image ChemSpider 6775 Y ECHA InfoCard 100 001 859 PubChem CID 7042 UNII 978627YAJU Y CompTox Dashboard EPA DTXSID8029604 InChI InChI 1S C8H4N2 c9 5 7 3 1 2 4 8 7 6 10 h1 4H YKey XQZYPMVTSDWCCE UHFFFAOYSA N YInChI 1 C8H4N2 c9 5 7 3 1 2 4 8 7 6 10 h1 4HKey XQZYPMVTSDWCCE UHFFFAOYAX SMILES N Cc1ccccc1C N Properties Chemical formula C6H4 CN 2 Molar mass 128 13 g mol Appearance Off white crystals with lumps on the surface Odor Almond like Density 1 238 g cm3 2 Melting point 139 to 141 C 282 to 286 F 412 to 414 K Boiling point sublimes Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesSynthesis editPhthalonitrile is produced industrially in a single stage continuous process by the ammoxidation of o xylene at 480 C The reaction is catalyzed by vanadium oxide antimony oxide in a fluidized bed reactor 2 nbsp 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 amidobenzonitrile hydrochloride sodium nitrite and hydrochloric acid 3 The first intentional synthesis involved dehydration of phthalamide by boiling in acetic anhydride 4 Another synthesis of historical interest is the Rosenmund von Braun reaction in which an ortho substituted dihalobenzene is treated with copper I cyanide which results in the halide groups being replaced by cyano groups 5 Applications editPhthalonitrile is the precursor to phthalocyanine 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 6 nbsp Ammonolysis of phthalonitrile gives to diiminoisoindoline This intermediate condensation with active methylene compounds to give commercially important pigment yellow 185 and pigment yellow 139 References edit a b Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 Blue Book Cambridge The Royal Society of Chemistry 2014 p 902 doi 10 1039 9781849733069 FP001 ISBN 978 0 85404 182 4 a b Lorz Peter M Phthalic Acid and Derivatives in Ulmanns Encyclopedia of Industrial Chemistry Wiley VCH Weinheim 2002 doi 10 1002 14356007 a20 181 pub2 Pinnow Johannes Samann C Ueber Derivate des o Amidobenzonitrils Derivatives of Orthamidobenzonitrile Berichte der Deutschen Chemischen Gesellschaft 1896 volume 29 623 32 doi 10 1002 cber 189602901118 Braun A Tscherniac J Uber 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 Karl M Kadish Kevin M Smith Roger Guilard The Porphyrin Handbook 2003 Lobbert Gerd 2000 Phthalocyanines Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a20 213 ISBN 3527306730 Retrieved from https en wikipedia org w index php title Phthalonitrile amp oldid 1191682600, wikipedia, wiki, book, books, library,
