| Revision as of 08:39, 6 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit |
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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 413109950 |
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| Watchedfields = changed |
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| Name = 2-Ethylhexanol |
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| verifiedrevid = 477213343 |
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| ImageFile = 2-ethylhexanol-Line-Structure.svg |
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| ImageFile = 2-Ethylhexanol 2D.svg |
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| ImageSize = 200px |
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| ImageSize = 180 |
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| ImageName = 2-Ethylhexanol |
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| ImageName = Skeletal formula of 2-ethylhexanol |
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| IUPACName = 2-Ethyl-1-hexanol |
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| ImageFile1 = 2-Ethylhexanol-3D-balls.png |
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| OtherNames = Isooctanol<br />Isooctyl alcohol<br />2-Ethylhexyl alcohol<br />Oxooctyl alcohol |
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| ImageSize1 = 180 |
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| ImageAlt1 = 2-Ethylhexanol molecule |
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| PIN = 2-Ethylhexan-1-ol<ref>{{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 |access-date=29 January 2012 |location=USA |date=16 September 2005 |at=Identification and Related Records}}</ref> |
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| OtherNames = isooctyl alcohol, 2-ethylhexanol |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 104-76-7 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 7720 |
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| PubChem1 = 6991979 |
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| PubChem1_Comment = (''R'' enantiomer) |
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| PubChem2 = 6991980 |
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| PubChem2_Comment = (''S'' enantiomer) |
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| ChemSpiderID = 7434 |
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| ChemSpiderID = 7434 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1 = 5360145 |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Comment = (''R'' enantiomer) |
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| ChemSpiderID2 = 5360146 |
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| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID2_Comment = (''S'' enantiomer) |
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| UNII = XZV7TAA77P |
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| UNII = XZV7TAA77P |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-234-3 |
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| KEGG = C02498 |
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| KEGG = C02498 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| InChI = 1/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 |
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| MeSHName = 2-ethylhexanol |
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| InChIKey = YIWUKEYIRIRTPP-UHFFFAOYAU |
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| ChEBI = 16011 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 31637 |
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| ChEMBL = 31637 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL1 = 1229918 |
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| ChEMBL1_Ref = {{ebicite|correct|EBI}} |
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| Beilstein = 1719280 |
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| SMILES = CCCCC(CC)CO |
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| StdInChI = 1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 |
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| StdInChI = 1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YIWUKEYIRIRTPP-UHFFFAOYSA-N |
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| StdInChIKey = YIWUKEYIRIRTPP-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo = 104-76-7 |
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| ChEBI = 16011 |
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| SMILES = OCC(CC)CCCC |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>18</sub>O |
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| Formula = {{chem2|CH3CH2CH2CH2CH(CH2CH3)CH2OH}} |
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| C = 8 |
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| MolarMass = 130.23 g/mol |
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| H = 18 |
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| Density = 0.833 g/cm³ |
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| MeltingPt = -76 °C |
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| O = 1 |
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| Appearance = Colourless liquid |
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| BoilingPt = 183-185 °C |
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| Density = 833 mg/mL |
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}} |
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| MeltingPtC = −76 |
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| BoilingPtK = 453 to 459 |
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| LogP = 2.721 |
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| VaporPressure = 30 Pa (at 20 °C) |
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| RefractIndex = 1.431 |
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}} |
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}} |
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| Section3 = {{Chembox Thermochemistry |
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| DeltaHf = −433.67–−432.09 kJ/mol |
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| DeltaHc = −5.28857–−5.28699 MJ/mol |
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| Entropy = 347.0 J/(K·mol) |
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| HeatCapacity = 317.5 J/(K·mol) |
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}} |
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| Section7 = {{Chembox Hazards |
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| MainHazards= Mildly toxic |
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| GHSPictograms = {{GHS exclamation mark}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|302|312|315|318|335}} |
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| PPhrases = {{P-phrases|261|280|305+351+338}} |
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| FlashPtC = 81 |
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| AutoignitionPtC = 290 |
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| ExploLimits = 0.88–9.7% |
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| LD50 = {{Unbulleted list|1.97 g/kg (dermal, rabbit)|3.73 g/kg (oral, rat)}} |
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| IDLH = N.D.<ref name=PGCH>{{PGCH|0354}}</ref> |
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| PEL = none<ref name=PGCH/> |
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| REL = TWA 50 ppm (270 mg/m<sup>3</sup>) (skin)<ref name=PGCH/> |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunction_label = alkanol |
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| OtherFunction = ] |
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| OtherCompounds = {{Unbulleted list|]|]|]|]|]|]|]}} |
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}} |
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}} |
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'''2-Ethylhexanol''' (abbreviated '''2-EH''') is an ] with the ] {{chem2|CH3CH2CH2CH2CH(CH2CH3)CH2OH|auto=1}}. It is a branched, eight-carbon ] ]. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is ]d on a large 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.<ref name=ROH/> It is encountered in plants, fruits, and wines.<ref>{{cite journal |doi=10.1021/jf052635t |title=Characterization of Aroma Compounds of Chinese "Wuliangye" and "Jiannanchun" Liquors by Aroma Extract Dilution Analysis |year=2006 |last1=Fan |first1=Wenlai |last2=Qian |first2=Michael C. |journal=Journal of Agricultural and Food Chemistry |volume=54 |issue=7 |pages=2695–2704 |pmid=16569063}}</ref><ref>{{cite journal |doi=10.1007/s00217-012-1757-0 |title=Identification of aroma-active compounds in 'wonderful' pomegranate fruit using solvent-assisted flavour evaporation and headspace solid-phase micro-extraction methods |year=2012 |last1=Mayuoni-Kirshinbaum |first1=Lina |last2=Tietel |first2=Zipora |last3=Porat |first3=Ron |last4=Ulrich |first4=Detlef |journal=European Food Research and Technology |volume=235 |issue=2 |pages=277–283 |s2cid=97102092}}</ref> The odor has been reported as "heavy, earthy, and slightly floral" for the R ] and "a light, sweet floral fragrance" for the S enantiomer.<ref>{{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 |url=https://opus.bibliothek.uni-wuerzburg.de/files/4494/Burschka_Esters.pdf}}</ref><ref>{{cite journal |doi=10.1016/j.fct.2010.05.042 |title=Fragrance material review on 2-ethyl-1-hexanol |year=2010 |last1=McGinty |first1=D. |last2=Scognamiglio |first2=J. |last3=Letizia |first3=C.S. |last4=Api |first4=A.M. |journal=Food and Chemical Toxicology |volume=48 |pages=S115–S129 |pmid=20659633}}</ref> |
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==Properties and applications== |
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'''2-Ethylhexanol''' (abbreviated 2-EH) is a ], an organic compound is a branched, eight-carbon ] ]. It is a colorless liquid that is nearly insoluble in water but soluble in most organic solvents. It is produced on a massive scale as a precursor to plasticizers, some of which are controversial as potential ]s. |
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The branching in 2-ethylhexanol inhibits crystallization. Esters of 2-ethylhexanol are similarly affected, which together with low volatility, is the basis of applications in the production of ]s and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a ], its ]s have ] properties. Representative is the ] ] (DEHP), commonly used in ]. The triester tris (2-Ethylhexyl) trimellitate (TOTM) is another common plasticizer produced via the ] of three 2-ethylhexanol per ]. |
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It is also commonly used as a low volatility ]. The ] of 2-Ethylhexanol is also used as a ] for ]. It also used to react with ] and ] to produce ] which is then used as an epoxy reactive diluent in various ]s, ]s and ]s applications. It can be used in the development of photos, production of rubber and extraction of oil and gas.<ref>{{cite web |url=https://berrymanchemical.com/blog/2-ethylhexanol/ |title=Product Spotlight: 2-Ethylhexanol |date=December 12, 2019}}</ref> |
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==Applications== |
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Almost all 2-ethylhexanol is converted into the di]s ] (DEHP), a ]. Because it is a ], its ]s tend to have ] properties. For example, the ] ] contains a 2-ethylhexyl ester for this purpose. It is also commonly used as a low volatility ]. |
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== Industrial production == |
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==Industrial production== |
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2-Ethylhexanol is produced industrially by the ] of ''n''-], followed by hydrogenation of the resulting hydroxyaldehyde. About 2,500,000 tons are prepared in this way annually.<ref name=aliphald>C. Kohlpaintner, M. Schulte, J. Falbe, P. Lappe, J. Weber, "Aldehydes, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2008, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a01_321.pub2}}.</ref><ref>Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-1</ref>. The ''n''-butyraldehyde is made by ] of ], either in a self-contained plant or as the first step in a fully-integrated facility. Most facilities make ''n''-butanol and ] in addition to 2-ethylhexanol. |
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2-Ethylhexanol is produced industrially by the ] ]. About 2,500,000 tons are prepared in this way annually.<ref name=aliphald>{{cite encyclopedia |author1=C. Kohlpaintner |author2=M. Schulte |author3=J. Falbe |author4=P. Lappe |author5=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=978-3-527-30673-2}}</ref><ref>Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-4181.</ref> |
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==Health effects== |
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2-Ethylhexanol exhibits low toxicity in animal models, with ] ranging from 2-3 g/kg (rat).<ref name=ROH>{{cite encyclopedia |author1=Helmut Bahrmann |author2=Heinz-Dieter Hahn |author3=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=978-3-527-30673-2}}</ref> 2-Ethylhexanol has been identified as a cause of ] related health problems, such as ] irritation, as a ]. 2-Ethylhexanol is emitted to air from a ] flooring installed on ] that had not been dried properly.<ref>{{cite journal |last1=Ernstgård |first1=L. |last2=Norbäck |first2=D. |date=2010 |title=Acute effects of exposure to 1 mg/m(3) of vaporized 2-ethyl-1-hexanol in humans |journal=Indoor Air |volume=20 |issue=2 |pages=168–75 |doi=10.1111/j.1600-0668.2009.00638.x |pmid=20409194|doi-access=free }}</ref><ref>{{cite journal |last1=Hildenbrand |first1=S. |last2=Wodarz |first2=R. |date=2009 |title=Biomonitoring of the di(2-ethylhexyl) phthalate metabolites mono(2-ethyl-5-hydroxyhexyl) phthalate and mono(2-ethyl-5-oxohexyl) phthalate in children and adults during the course of time and seasons. |journal=] |volume=212 |issue=6 |pages=679–84 |doi=10.1016/j.ijheh.2009.06.003 |pmid=19615938}}</ref> |
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2-Ethylhexanol has been linked to ] (increased incidence of skeletal malformations in fetuses).<ref>{{cite web |publisher=US EPA: National Center for Environmental Assessment |title=2-Ethylhexanol: Provisional Peer-Reviewed Toxicity Values (PPRTVs) |language=en |website=cfpub.epa.gov |url=https://cfpub.epa.gov/ncea/pprtv/chemicalLanding.cfm?pprtv_sub_id=2005 |access-date=2021-04-09}}</ref> This is thought to be a result of metabolism of 2-ethylhexanol into ] via oxidation of the primary alcohol.<ref>{{cite web |vauthors=Deisinger PJ, Boatman RJ, Guest D |date=2009-03-15 |title=Metabolism of 2-ethylhexanol administered orally and dermally to the female Fischer-344 rat |url=https://hero.epa.gov/index.cfm/reference/details/reference_id/3046161 |language=en |website=hero.epa.gov |access-date=2021-04-09 |url-status=live |archive-url=https://web.archive.org/web/20211122011424/https://hero.epa.gov/index.cfm/reference/details/reference_id/3046161 |archive-date=2021-11-22}}</ref><ref>{{cite web |last=Eastman Kodak Company |first=Eastman Kodak |date=2009-03-15 |title=Pharmacokinetic studies with 2-ethylhexanol in the female fischer 344 rat (final report) with attachments and cover letter dated 050791 |language=en |website=hero.epa.gov |url=https://hero.epa.gov/index.cfm/reference/details/reference_id/3006683 |access-date=2021-04-09 |url-status=live |archive-url=https://web.archive.org/web/20211122011435/https://hero.epa.gov/index.cfm/reference/details/reference_id/3006683 |archive-date=2021-11-22}}</ref> The ] of 2-ethylhexanoic acid, as well as similar substances such as ], has been well established.<ref>{{cite journal |last1=Pennanen |first1=Sirpa |last2=Tuovinen |first2=Kai |last3=Huuskonen |first3=Hannele |last4=Komulainen |first4=Hannu |year=1992 |title=The developmental toxicity of 2-ethylhexanoic acid in Wistar rats |url=https://www.sciencedirect.com/science/article/abs/pii/027205909290088Y |journal=Fundamental and Applied Toxicology |volume=19 |issue=4 |pages=505–511 |doi=10.1016/0272-0590(92)90088-Y |pmid=1426708 |via=Elsevier}}</ref><ref>{{cite web |title=2-Ethylhexanoic acid |publisher=ACGIH |url=https://haz-map.com/Agents/1405 |access-date=2021-04-09 |url-status=live |archive-url=https://web.archive.org/web/20211122002908/https://haz-map.com/Agents/1405 |archive-date=2021-11-22}}</ref><ref>{{cite web |title=Annex 1 Background Document to the Opinion proposing harmonised classification and labelling at EU level of 2-Ethylhexanoic acid and its salts, with the exception of those specified elsewhere in this Annex |date=2020 |url=https://echa.europa.eu/documents/10162/c58bf900-5d67-463f-3d45-1e09009a1e22 |access-date=2021-04-09 |publisher=European Chemicals Agency}}</ref><ref>{{cite web |title=Valproic Acid |publisher=The American Society of Health-System Pharmacists |url=https://www.drugs.com/monograph/valproic-acid.html |access-date=Oct 23, 2015 |url-status=live |archive-url=https://web.archive.org/web/20170731065623/https://www.drugs.com/monograph/valproic-acid.html |archive-date=2017-07-31}}</ref><ref>{{cite web |title=Valproate banned without the pregnancy prevention programme |website=GOV.UK |url=https://www.gov.uk/government/news/valproate-banned-without-the-pregnancy-prevention-programme |access-date=26 April 2018 |url-status=live |archive-url=https://web.archive.org/web/20180424123455/https://www.gov.uk/government/news/valproate-banned-without-the-pregnancy-prevention-programme |archive-date=2018-04-24}}</ref> |
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==Nomenclature== |
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==Nomenclature== |
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Although '''isooctanol''' (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives, ] naming conventions<ref>{{cite web |url=https://www.acdlabs.com/iupac/nomenclature/79/r79_36.htm |title=Rule A-2. Saturated Branched-chain Compounds and Univalent Radicals (ACYCLIC HYDROCARBONS) |website=acdlabs.com}}</ref> dictate that this name is properly applied to another ] of ], 6-methylheptan-1-ol. The ] likewise indexes isooctanol (CAS# 26952-21-6) as 6-methylheptan-1-ol. |
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Isooctanol and 2-ethylhexanol are not synonyms. According to the Chemical Abstracts Service, isooctanol (CAS# 26952-21-6) refers to a different ] of ], 6-methylheptan-1-ol. |
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==See also== |
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==See also== |
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==References== |
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==References== |
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{{Reflist}} |
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<references/> |
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==External links== |
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==External links== |
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* , National Institute for Occupational Safety and Health (NIOSH) |
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{{alcohols}} |
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{{DEFAULTSORT:Ethylhexanol, 2-}} |
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{{Authority control}}{{DEFAULTSORT:Ethylhexanol, 2-}} |
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