Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-Ethylhexanol: Difference between pages

| Verifiedfields = changed

| verifiedrevid =

| ImageFile = 2-.svg

| ImageSize =

| ImageFile1 = 2-Ethylhexanol-3D-balls.png

| ImageSize1 = 180

| ImageAlt1 = 2-Ethylhexanol molecule

| 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>

| OtherNames = isooctyl alcohol, 2-ethylhexanol

| CASNo = 104-76-7

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 7720

| PubChem1 = 6991979

| PubChem1_Comment = (''R'' enantiomer)

| PubChem2 = 6991980

| PubChem2_Comment = (''S'' enantiomer)

| =

| = {{|correct|}}

| ChemSpiderID1 = 5360145

| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID1_Comment = (''R'' enantiomer)

| ChemSpiderID2 = 5360146

| = {{chemspidercite|correct|chemspider}}

| ChemSpiderID2_Comment = (''S'' enantiomer)

| UNII = XZV7TAA77P

| = {{|correct|}}

| EINECS = 203-234-3

| =

| = {{||}}

| MeSHName = 2-ethylhexanol

| ChEBI = 16011

| = {{|correct|}}

| ChEMBL = 31637

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL1 = 1229918

| ChEMBL1_Ref = {{ebicite|correct|EBI}}

| Beilstein = 1719280

| =

| 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}}

| Formula = {{chem2|CH3CH2CH2CH2CH(CH2CH3)CH2OH}}

| =

| =

| O = 1

| Appearance = Colourless liquid

| Density = 833 mg/mL

| MeltingPtC = −76

| = 453

| =

| VaporPressure = 30 Pa (at 20&nbsp;°C)

| RefractIndex = 1.431

| DeltaHf = −433.67–−432.09 kJmol

| DeltaHc = −5.28857–−5.28699 MJmol

| Entropy = 347.0 JKmol

| HeatCapacity = 317. Kmol

| = {{Chembox Hazards

| MainHazards= Mildly toxic

| GHSPictograms = {{GHS exclamation mark}}

| GHSSignalWord = '''DANGER'''

| = {{-phrases|||}}

| PPhrases = {{P-phrases|261|280|305+351+338}}

| FlashPtC = 81

| AutoignitionPtC = 290

| ExploLimits = 0.88–9.7%

| LD50 = {{Unbulleted list|1.97 g/kg (dermal, rabbit)|3.73 g/kg (oral, rat)}}

| IDLH = N.D.<ref name=PGCH>{{PGCH|0354}}</ref>

| PEL = none<ref name=PGCH/>

| REL = TWA 50 ppm (270 mg/m³) (skin)<ref name=PGCH/>

| = {{Chembox Related

| OtherFunction_label = alkanol

| = [[Propylheptyl alcohol]]

| OtherCompounds = {{Unbulleted list|[[2-Methylhexane]]|[[3-Methylhexane]]|[[Valnoctamide]]|[[2-Methylheptane]]|[[3-Methylheptane]]|[[Valpromide]]|[[2-Ethylhexanoic acid]]}}

'''2-Ethylhexanol''' (abbreviated '''2-EH''') is an [[organic compound]] with the [[chemical formula]] {{chem2|CH3CH2CH2CH2CH(CH2CH3)CH2OH|auto=1}}. It is a branched, eight-carbon [[chiral]] [[alcohol (chemistry)|alcohol]]. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is [[produce]]d on a large scale (>2,000,000,000&nbsp;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 [[enantiomer]] 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>

==Properties and applications==

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 [[plasticizer]]s and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a [[fatty alcohol]], its [[ester]]s have [[emollient]] properties. Representative is the [[ester|diester]] [[bis(2-ethylhexyl) phthalate]] (DEHP), commonly used in [[polyvinyl chloride|PVC]]. The triester tris (2-Ethylhexyl) trimellitate (TOTM) is another common plasticizer produced via the [[esterification]] of three 2-ethylhexanol per [[trimellitic acid]].

It is also commonly used as a low volatility [[solvent]]. The [[nitrate ester]] of 2-Ethylhexanol is also used as a [[cetane improver]] for [[diesel fuel]]. It also used to react with [[epichlorohydrin]] and [[sodium hydroxide]] to produce [[2-Ethylhexyl glycidyl ether]] which is then used as an epoxy reactive diluent in various [[coating]]s, [[adhesive]]s and [[sealant]]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>

==Industrial production==

2-Ethylhexanol is produced industrially by the [[hydrogenation]] [[2-Ethylhexanal|2-ethylhexanal]]. 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>

==Health effects==

2-Ethylhexanol exhibits low toxicity in animal models, with [[LD50]] 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 [[indoor air quality]] related health problems, such as [[respiratory system]] irritation, as a [[volatile organic compound]]. 2-Ethylhexanol is emitted to air from a [[polyvinyl chloride|PVC]] flooring installed on [[concrete]] 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=[[International Journal of Hygiene and Environmental Health]] |volume=212 |issue=6 |pages=679–84 |doi=10.1016/j.ijheh.2009.06.003 |pmid=19615938}}</ref>

2-Ethylhexanol has been linked to [[developmental toxicity]] (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 [[2-Ethylhexanoic acid|2-ethylhexanoic acid]] 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 [[teratogenicity]] of 2-ethylhexanoic acid, as well as similar substances such as [[valproic acid]], 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>

==Nomenclature==

Although '''isooctanol''' (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives, [[IUPAC]] 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 [[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==

*[[2-Ethylhexanoic acid]]

==References==

{{Reflist}}

==External links==

* [https://www.cdc.gov/niosh/npg/npgd0354.html Isooctyl alcohol], National Institute for Occupational Safety and Health (NIOSH)

{{alcohols}}

{{Authority control}}{{DEFAULTSORT:Ethylhexanol, 2-}}

[[Category:Alcohol solvents]]

[[Category:Alkanols]]

[[Category:Primary alcohols]]

[[Category:Ethyl compounds]]