| 词条 | Cyclohexene |
| 释义 |
| Watchedfields = changed | verifiedrevid = 414090407 | ImageFileL1 = Olefine am Beispiel von Cycloalken-v2.svg | ImageFileR1 = Cyclohexene for highscool.svg | ImageFileL2 = Cyclohexene-conformation-2D-skeletal.png | ImageFileR2 = Cyclohexen.png | PIN = Cyclohexene | OtherNames = Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256 |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7788 | InChIKey = HGCIXCUEYOPUTN-UHFFFAOYAQ | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 16396 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HGCIXCUEYOPUTN-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 110-83-8 | EINECS = 203-807-8 | PubChem = 8079 | SMILES = C1CCC=CC1 | InChI = 1/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2 | RTECS = GW2500000 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 36404 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = |Section2={{Chembox Properties | Formula = C6H10 | MolarMass = 82.143 g/mol | Appearance = colorless liquid | Odor = sweet | Density = 0.8110 g/cm3 | MeltingPtC = -103.5 | BoilingPtC = 82.98 | Solubility = insoluble in water | SolubleOther = miscible with organic solvents | VaporPressure = 8.93 kPa (20 °C) 11.9 kPa (25 °C) | HenryConstant = 0.022 mol·kg−1·bar−1 | RefractIndex = 1.4465 | MagSus = -57.5·10−6 cm3/mol |Section3={{Chembox Hazards | ExternalSDS = External MSDS | MainHazards = | NFPA-H = 1 | NFPA-F = 3 | NFPA-R = 0 | NFPA-S = | RPhrases = {{R11}}, {{R19}}, {{R21/22}} | SPhrases = {{S16}}, {{S23}}, {{S24}}, {{S25}}, {{S33}} | FlashPtC = -12 | AutoignitionPtC = 244 | ExploLimits = 0.8–5 % | LD50 = 1946 mg/kg (oral, rat) | PEL = TWA 300 ppm (1015 mg/m3)[1] | IDLH = 2000 ppm[1] | REL = TWA 300 ppm (1015 mg/m3)[1] | LCLo = 13,196 ppm (mouse, 2 hr)[2] }} Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides. Production and usesCyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company.[3] It is converted to cyclohexanol, which is dehydrogenated to give cyclohexanone, a precursor to caprolactam.[4] Cyclohexene is also a precursor to adipic acid, maleic acid, dicyclohexyladipate, and cyclohexene oxide. Furthermore, it is used as a solvent. Laboratory experimentsSynthesisA common experiment for beginning organic chemistry students{{citation needed|date=May 2016}} is the acid-catalyzed dehydration of cyclohexanol with distillative removal of the resulting cyclohexene from the reaction mixture: Oxidative cleavageA green chemistry experiment is the oxidative cleavage of cyclohexene to form adipic acid. Hydrogen peroxide is used as the oxidant, in the presence of a tungsten catalyst.[5] StructureCyclohexene is most stable in a half-chair conformation,[6] unlike the preference for a chair form of cyclohexane. One basis for the cyclohexane conformational preference for a chair is that it allows each bond of the ring to adopt a staggered conformation. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond. See also
External links
References1. ^1 2 {{PGCH|0167}} {{cycloalkenes}}2. ^{{IDLH|110838|Cyclohexene}} 3. ^{{Citation|title=Cyclohexanol, method for producing cyclohexanol, and method for producing adipic acid|date=26 Sep 2017|url=http://www.google.com.au/patents/US9771313|inventor-last=Narisawa|inventor2-last=Tanaka|inventor-first=Naoki|inventor2-first=Katsutoshi|issue=US9771313 B2|accessdate=2017-12-04}} 4. ^Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.{{DOI|10.1002/14356007.a08_217}} 5. ^{{cite journal |title= Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid |first1= Scott M. |last1= Reed |first2= James E. |last2= Hutchison |journal= J. Chem. Educ. |year= 2000 |volume= 77 |issue= 12 |pages= 1627–1629 |doi= 10.1021/ed077p1627 }} 6. ^{{ cite journal |title= Conformational preferences and interconversion barriers in cyclohexene and derivatives |first1= Frederick R. |last1= Jensen |first2= C. Hackett |last2= Bushweller |journal= J. Am. Chem. Soc. |year= 1969 |volume= 91 |issue= 21 |pages= 5774–5782 |doi= 10.1021/ja01049a013 }} 2 : Cycloalkenes|Hydrocarbon solvents |
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