| 词条 | 2-Ethylhexanol |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477213343 | ImageFile = 2-Ethylhexanol 2D.svg | ImageSize = 180 | ImageName = Skeletal formula of 2-ethylhexanol | ImageFile1 = 2-Ethylhexanol-3D-balls.png | ImageSize1 = 180 | ImageAlt1 = 2-Ethylhexanol molecule | IUPACName = 2-Ethylhexan-1-ol[1] | Section1 = {{Chembox Identifiers | CASNo = 104-76-7 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 7720 | PubChem1 = 6991979 | PubChem1_Comment = R | PubChem2 = 6991980 | PubChem2_Comment = S | ChemSpiderID = 7434 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1 = 5360145 | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1_Comment = R | ChemSpiderID2 = 5360146 | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID2_Comment = S | UNII = XZV7TAA77P | UNII_Ref = {{fdacite|correct|FDA}} | EINECS = 203-234-3 | KEGG = C02498 | KEGG_Ref = {{keggcite|changed|kegg}} | MeSHName = 2-ethylhexanol | ChEBI = 16011 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEMBL = 31637 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL1 = 1229918 | ChEMBL1_Ref = {{ebicite|correct|EBI}} | Beilstein = 1719280 | SMILES = CCCCC(CC)CO | StdInChI = 1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YIWUKEYIRIRTPP-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} | Section2 = {{Chembox Properties | C = 8 | H = 18 | O = 1 | Appearance = Colourless liquid | Density = 833 mg mL−1 | MeltingPtC = −76 | BoilingPtK = 453 to 459 | LogP = 2.721 | VaporPressure = 30 Pa (at 20 °C) | RefractIndex = 1.431 }} | Section3 = {{Chembox Thermochemistry | DeltaHf = −433.67–−432.09 kJ mol−1 | DeltaHc = −5.28857–−5.28699 MJ mol−1 | Entropy = 347.0 J K−1 mol−1 | HeatCapacity = 317.5J K−1 mol−1 }} | Section4 = {{Chembox Hazards | GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}} | GHSSignalWord = DANGER | HPhrases = {{H-phrases|312|315|318|335}} | PPhrases = {{P-phrases|261|280|305+351+338}} | FlashPtC = 81 | AutoignitionPtC = 290 | ExploLimits = 0.88–9.7% | LD50 = {{Unbulleted list|1.97 g kg−1 (dermal, rabbit)|3.73 g kg−1 (oral, rat)}} | IDLH = N.D.[2] | PEL = none[2] | REL = TWA 50 ppm (270 mg/m3) [skin][2] }} | Section5 = {{Chembox Related | OtherFunction_label = alkanol | OtherFunction = Propylheptyl alcohol | OtherCompounds = {{Unbulleted list|2-Methylhexane|3-Methylhexane|Valnoctamide|2-Methylheptane|3-Methylheptane|Valpromide|2-Ethylhexanoic acid}} }} }}2-Ethylhexanol (abbreviated 2-EH) is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a massive scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers.[5] It is encountered in natural plant fragrances, and the odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.[3] Properties and applicationsThe branching in 2-ethylhexanol inhibits its crystallization due to packing disruption; this results in a very low freezing point. Esters of 2-ethylhexanol are similarly affected and it therefore finds application as a feedstock in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points. Almost all 2-ethylhexanol manufactured is used as a precursor for the synthesis of the diester bis(2-ethylhexyl) phthalate (DEHP), a plasticizer. Because it is a fatty alcohol, its esters tend to have emollient properties. It is also commonly used as a low volatility solvent. 2-Ethylhexanol can also be used as an octane booster when reacted with nitric acid. It also used to react with epichlorohydrin and sodium hydroxide to produce the glycidyl ether of the molecule which is used as an epoxy reactive diluent in various coatings, adhesives and sealants applications. Industrial production2-Ethylhexanol is produced industrially by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde. About 2,500,000 tons are prepared in this way annually.[4][5] The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility. Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.[6] Health effects2-Ethylhexanol exhibits low toxicity in animal models, with LD50 ranging from 2-3 g/kg (rat).[7] NomenclatureAlthough isooctanol (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives, IUPAC naming conventions[8] dictate that this name is properly applied to another isomer of octanol, 6-methylheptan-1-ol. The Chemical Abstracts Service likewise indexes isooctanol (CAS# 26952-21-6) as 6-methylheptan-1-ol. See also
References1. ^{{Cite web|title=2-ethylhexanol - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7720|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=29 January 2012|location=USA|date=16 September 2005|at=Identification and Related Records}} 2. ^1 2 {{PGCH|0354}} 3. ^{{cite journal|author1=Klaus Rettinger|author2=Christian Burschka|author3=Peter Scheeben|author4=Heike Fuchs|author5=Armin Mosandl|title=Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation|journal=Tetrahedron: Asymmetry|date=1991|volume=2|issue=10|pages=965–968|doi=10.1016/S0957-4166(00)86137-6}} 4. ^{{cite encyclopedia|authors=C. Kohlpaintner, M. Schulte, J. Falbe, P. Lappe, J. Weber|chapter=Aldehydes, Aliphatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2008|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a01_321.pub2|isbn=978-3527306732}} 5. ^Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-4181. 6. ^{{cite journal|last1=Miller|first1=Robert|last2=Bennett|first2=George|title=Producing 2-Ethylhexanol by the Guerbet Reaction|journal=Industrial & Engineering Chemistry|date=January 1961|volume=53|issue=1|pages=33–36|doi=10.1021/ie50613a027}} 7. ^1 {{cite encyclopedia|authors=Helmut Bahrmann, Heinz-Dieter Hahn, Dieter Mayer|chapter=2-Ethylhexanol|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a10_137|isbn=978-3527306732}} 8. ^IUPAC Blue Book, A2.25 External links
3 : Alcohol solvents|Primary alcohols|Alkanols |
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