Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer.
Alternatively, another industrial route involves the reaction of cyclohexane with nitrosyl chloride, which is a free radical reaction. This method is advantageous as cyclohexane is much cheaper than cyclohexanone.
^ abJ. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. doi:10.15227/orgsyn.019.0020
^Corma, Avelino; Garcia, Hermenegildo "Organic reactions catalyzed over solid acids" Catalysis Today 1997, volume 38, pp. 257-308. doi:10.1016/S0920-5861(97)81500-1
^W. H. Lycan, S. V. Puntambeker, and C. S. Marvel "n-Heptylamine" Org. Synth. 1931, volume 11, pp. 58.doi:10.15227/orgsyn.011.0058
October 15, 2023
cyclohexanone, oxime, confused, with, caprolactam, organic, compound, containing, functional, group, oxime, this, colorless, solid, important, intermediate, production, nylon, widely, used, polymer, namespreferred, iupac, name, hydroxycyclohexanimineidentifier. Not to be confused with caprolactam Cyclohexanone oxime is an organic compound containing the functional group oxime This colorless solid is an important intermediate in the production of nylon 6 a widely used polymer Cyclohexanone oxime NamesPreferred IUPAC name N HydroxycyclohexanimineIdentifiersCAS Number 100 64 13D model JSmol Interactive imageChEMBL ChEMBL137035ChemSpider 7236ECHA InfoCard 100 002 613EC Number 202 874 0PubChem CID 7517UNII 2U60L00CGF YUN number 2811CompTox Dashboard EPA DTXSID4021842InChI InChI 1S C6H11NO c8 7 6 4 2 1 3 5 6 h8H 1 5H2Key VEZUQRBDRNJBJY UHFFFAOYSA NInChI 1 C6H11NO c8 7 6 4 2 1 3 5 6 h8H 1 5H2Key VEZUQRBDRNJBJY UHFFFAOYAHSMILES C1CCC NO CC1PropertiesChemical formula C6H11NOMolar mass 113 16 g molAppearance white solidMelting point 88 to 91 C 190 to 196 F 361 to 364 K Boiling point 204 to 206 C 399 to 403 F 477 to 479 K Solubility in water 16 g kg in water Magnetic susceptibility x 71 52 10 6 cm3 molHazardsGHS labelling PictogramsSignal word WarningHazard statements H228 H302 H319 H373 H412Precautionary statements P210 P240 P241 P260 P264 P270 P273 P280 P301 P312 P305 P351 P338 P314 P330 P337 P313 P370 P378 P501Flash point 110 C 230 F 383 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesPreparation EditCyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine 1 C5H10CO H2NOH C5H10C NOH H2OAlternatively another industrial route involves the reaction of cyclohexane with nitrosyl chloride which is a free radical reaction This method is advantageous as cyclohexane is much cheaper than cyclohexanone Reactions EditThe most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding e caprolactam nbsp This reaction is catalyzed by sulfuric acid 1 but industrial scale reactions use solid acids 2 Typical of oximes the compound can be reduced by sodium amalgam to produce cyclohexylamine 3 It can also be hydrolyzed with acetic acid to give back cyclohexanone References Edit a b J C Eck and C S Marvel e Benzoylaminocaproic Acid Org Synth 1939 volume 19 pp 20 doi 10 15227 orgsyn 019 0020 Corma Avelino Garcia Hermenegildo Organic reactions catalyzed over solid acids Catalysis Today 1997 volume 38 pp 257 308 doi 10 1016 S0920 5861 97 81500 1 W H Lycan S V Puntambeker and C S Marvel n Heptylamine Org Synth 1931 volume 11 pp 58 doi 10 15227 orgsyn 011 0058 Retrieved from https en wikipedia org w index php title Cyclohexanone oxime amp oldid 1118576901, wikipedia, wiki, book, books, library,
