| 词条 | Isophorone |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443979911 | Name = Isophorone | Reference =[1] | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Isophorone.png | ImageSize = 120px | ImageName = Isophorone | PIN = 3,5,5-Trimethylcyclohex-2-en-1-one | OtherNames = 3,5,5-Trimethyl-2-cyclohexene-1-one 1,1,3-Trimethyl-3-cyclohexene-5-one Isoforone Isoacetophorone IP |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6296 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C14743 | InChI = 1/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3 | InChIKey = HJOVHMDZYOCNQW-UHFFFAOYAC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HJOVHMDZYOCNQW-UHFFFAOYSA-N | CASNo = 78-59-1 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 6544 | SMILES = O=C1\\C=C(/CC(C)(C)C1)C | EINECS = 201-126-0 }} |Section2={{Chembox Properties | C=9 | H=14 | O=1 | Density = 0.9255 g/cm3 | Appearance = Colorless to white liquid | Odor = Peppermint-like[2] | MeltingPtC = -8.1 | BoilingPtC = 215.32 | Solubility = 1.2 g/100 mL | SolubleOther = ether, acetone, hexane, dichloromethane, benzene, toluene, alcohol | RefractIndex = 1.4766 | Viscosity = 2.62 cP | VaporPressure = 0.3 mmHg (20°C)[2] }} |Section4={{Chembox Thermochemistry | DeltaHf = 43.4 kJ/mol }} |Section7={{Chembox Hazards | FlashPtC = 84 | AutoignitionPtC = 460 | LD50 = 2280 mg/kg (rat, oral){{citation needed|date=July 2015}} 2330 mg/kg (rat, oral) 2690 mg/kg (mouse, oral)[4] | IDLH = 200 ppm[2] | REL = TWA 4 ppm (23 mg/m3)[2] | PEL = TWA 25 ppm (140 mg/m3)[2] | ExploLimits = 0.8%-3.8%[2] | LC50 = 4600 ppm (guinea pig, 8 hr)[3] | LCLo = 885 ppm (rat, 6 hr) 1840 ppm (rat, 4 hr)[3] }}Isophorone is an α,β-unsaturated cyclic ketone. It is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. Used as a solvent and as a precursor to polymers, it is produced on a large scale industrially.[4] Structure and reactivityIsophorone undergoes reactions characteristic of an α,β-unsaturated ketone. Hydrogenation gives the cyclohexanone derivative. Epoxidation with basic hydrogen peroxide affords the oxide.[5] Isophorone is degraded by attack of hydroxyl radicals.[6] PhotodimerizationWhen exposed to sunlight in aqueous solutions, isophorone undergoes 2+2 photocycloaddition to give three isomeric photodimers (Figure). These "diketomers" are cis-syn-cis, head to tail (HT), cys-anti-cys (HT), and head-head (HH). The formation of HH photodimers is favored over HT photodimers with increasing polarity of the medium.[7] SynthesisIsophorone is produced on a multi-thousand ton scale by the aldol condensation of acetone using KOH. Diacetone alcohol, mesityl oxide, and 3-hydroxy-3,5,5-trimethylcyclohexan-1-one are intermediates. A side product is beta-isophorone, where the C=C group is not conjugated with the ketone.[4] ApplicationsThe hydrogenated derivative trimethylcyclohexanone is used in production of polycarbonates. It condenses with phenol to give an analogue of bisphenol A. Polycarbonates produced by phosgenation of these two diols produces a polymer with improved thermal stability.[8] Trimethyladipic acid and 2,2,4-trimethylhexamethylenediamine are produced from trimethylcyclohexanone and trimethylcyclohexanol. They are used to make specialty polyamides. Hydrocyanation gives the nitrile followed by reductive amination gives isophorone diamine. This diamine is used to produce isophorone diisocyanate which has certain niche applications.[4] SafetyThe LD50 value of isophorone in rats and rabbits by oral exposure is around the 2.00 g/kg.[9] The safety aspects of isophorone have been subject to several studies.[10] HistoryThe use of isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which is a waste product of phenol synthesis by the Hock method.[11] See also
References1. ^Merck Index, 13th Edition, 5215. 2. ^1 2 3 4 5 {{PGCH|0355}} 3. ^1 2 {{IDLH|78591|Isophorone}} 4. ^1 2 {{cite encyclopedia|authors=Hardo Siegel, Manfred Eggersdorfer|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a15_077|isbn=9783527306732|chapter=Ketones}} 5. ^{{cite journal|title=Isophorone Oxide|authors=Richard L. Wasson, Herbert O. House|journal=Org. Synth.|year=1957|volume=37|page=58|doi= 10.15227/orgsyn.037.0058}} 6. ^{{Cite web|url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+78-59-1|title = TOXNET|website = toxnet.nlm.nih.gov|access-date = 2016-03-11}} 7. ^{{Cite journal|last=Gonçalves|first=Huguette|last2=Robinet|first2=Germaine|last3=Barthelat|first3=Michèle|last4=Lattes|first4=Armand|date=1998-01-28|title=Supramolecularity and Photodimerization of Isophorone: FTIR and Molecular Mechanics Studies|journal=The Journal of Physical Chemistry A|language=en|volume=102|issue=8|pages=1279–1287|doi=10.1021/jp9729270}} 8. ^{{cite encyclopedia|authors=Volker Serini|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2000|doi=10.1002/14356007.a21_207|isbn=978-3527306732|chapter=Polycarbonates}} 9. ^{{Cite web|url=http://tools.niehs.nih.gov/cebs3/ntpviews/index.cfm?action=testarticle.toxicity&cas_number=389-08-2|title=Toxicity Effects|website=tools.niehs.nih.gov|access-date=2016-03-11}} 10. ^{{Cite journal|last=W. Morton Grant, Joel S. Schuman M.D|date=11 February 2016|title=Toxicology of the Eye: Effects on the Eyes and Visual System from Chemicals, Drugs, Metals and Minerals, Plants, Toxins, and Venoms; Also, Systemic Side Effects from Eye|url=|journal=Med (2-Volume Set) 4th Edition, Page 863|doi=|pmid=|access-date=}} 11. ^Isophorone history at Degussa 3 : Ketones|Ketone solvents|Cyclohexenes |
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