2-Ethylhexanol

2-Ethylhexanol
Skeletal formula of 2-ethylhexanol
2-Ethylhexanol molecule
Names
Preferred IUPAC name
2-Ethylhexan-1-ol[1]
Other names
isooctyl alcohol, 2-ethylhexanol
Identifiers
3D model (JSmol)
1719280
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.941 Edit this at Wikidata
EC Number
  • 203-234-3
KEGG
MeSH 2-ethylhexanol
UNII
  • InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 checkY
    Key: YIWUKEYIRIRTPP-UHFFFAOYSA-N checkY
  • CCCCC(CC)CO
Properties
CH3CH2CH2CH2CH(CH2CH3)CH2OH
Molar mass 130.231 g·mol−1
Appearance Colourless liquid
Density 833 mg/mL
Melting point −76 °C (−105 °F; 197 K)
Boiling point 180 to 186 °C; 356 to 367 °F; 453 to 459 K
log P 2.721
Vapor pressure 30 Pa (at 20 °C)
1.431
Thermochemistry
317.5 J/(K·mol)
347.0 J/(K·mol)
−433.67–−432.09 kJ/mol
−5.28857–−5.28699 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Mildly toxic
GHS labelling:
GHS07: Exclamation mark
Danger
H302, H312, H315, H318, H335
P261, P280, P305+P351+P338
Flash point 81 °C (178 °F; 354 K)
290 °C (554 °F; 563 K)
Explosive limits 0.88–9.7%
Lethal dose or concentration (LD, LC):
  • 1.97 g/kg (dermal, rabbit)
  • 3.73 g/kg (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 50 ppm (270 mg/m3) (skin)[2]
IDLH (Immediate danger)
 N.D.[2]
Related compounds
Related alkanol
 Propylheptyl alcohol
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH. It 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 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.[3] It is encountered in plants, fruits, and wines.[4][5] 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.[6][7]

Properties and applications

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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 plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a fatty alcohol, its esters have emollient properties. Representative is the diester bis(2-ethylhexyl) phthalate (DEHP), commonly used in 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 coatings, adhesives and sealants applications. It can be used in the development of photos, production of rubber and extraction of oil and gas.[8]

Industrial production

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2-Ethylhexanol is produced industrially by the hydrogenation 2-ethylhexanal. About 2,500,000 tons are prepared in this way annually.[9][10]

Synthesis of 2-Ethylhexanol

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. Alcohols prepared in this way are sometimes referred to as oxo alcohols. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.[11]

Health effects

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2-Ethylhexanol exhibits low toxicity in animal models, with LD50 ranging from 2-3 g/kg (rat).[3] 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 PVC flooring installed on concrete that had not been dried properly.[12][13]

2-Ethylhexanol has been linked to developmental toxicity (increased incidence of skeletal malformations in fetuses).[14] This is thought to be a result of metabolism of 2-ethylhexanol into 2-ethylhexanoic acid via oxidation of the primary alcohol.[15][16] The teratogenicity of 2-ethylhexanoic acid, as well as similar substances such as valproic acid, has been well established.[17][18][19][20][21]

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, IUPAC naming conventions[22] 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

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References

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  1. ^ "2-ethylhexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2005. Identification and Related Records. Retrieved 29 January 2012.
  2. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0354". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b Helmut Bahrmann; Heinz-Dieter Hahn; Dieter Mayer (2005). "2-Ethylhexanol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_137. ISBN 978-3-527-30673-2.
  4. ^ Fan, Wenlai; Qian, Michael C. (2006). "Characterization of Aroma Compounds of Chinese "Wuliangye" and "Jiannanchun" Liquors by Aroma Extract Dilution Analysis". Journal of Agricultural and Food Chemistry. 54 (7): 2695–2704. doi:10.1021/jf052635t. PMID 16569063.
  5. ^ Mayuoni-Kirshinbaum, Lina; Tietel, Zipora; Porat, Ron; Ulrich, Detlef (2012). "Identification of aroma-active compounds in 'wonderful' pomegranate fruit using solvent-assisted flavour evaporation and headspace solid-phase micro-extraction methods". European Food Research and Technology. 235 (2): 277–283. doi:10.1007/s00217-012-1757-0. S2CID 97102092.
  6. ^ Klaus Rettinger; Christian Burschka; Peter Scheeben; Heike Fuchs; Armin Mosandl (1991). "Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation" (PDF). Tetrahedron: Asymmetry. 2 (10): 965–968. doi:10.1016/S0957-4166(00)86137-6.
  7. ^ McGinty, D.; Scognamiglio, J.; Letizia, C.S.; Api, A.M. (2010). "Fragrance material review on 2-ethyl-1-hexanol". Food and Chemical Toxicology. 48: S115–S129. doi:10.1016/j.fct.2010.05.042. PMID 20659633.
  8. ^ "Product Spotlight: 2-Ethylhexanol". December 12, 2019.
  9. ^ C. Kohlpaintner; M. Schulte; J. Falbe; P. Lappe; J. Weber (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3-527-30673-2.
  10. ^ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-4181.
  11. ^ Miller, Robert; Bennett, George (January 1961). "Producing 2-Ethylhexanol by the Guerbet Reaction". Industrial & Engineering Chemistry. 53 (1): 33–36. doi:10.1021/ie50613a027.
  12. ^ Ernstgård, L.; Norbäck, D. (2010). "Acute effects of exposure to 1 mg/m(3) of vaporized 2-ethyl-1-hexanol in humans". Indoor Air. 20 (2): 168–75. doi:10.1111/j.1600-0668.2009.00638.x. PMID 20409194.
  13. ^ Hildenbrand, S.; Wodarz, R. (2009). "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". International Journal of Hygiene and Environmental Health. 212 (6): 679–84. doi:10.1016/j.ijheh.2009.06.003. PMID 19615938.
  14. ^ "2-Ethylhexanol: Provisional Peer-Reviewed Toxicity Values (PPRTVs)". cfpub.epa.gov. US EPA: National Center for Environmental Assessment. Retrieved 2021-04-09.
  15. ^ Deisinger PJ, Boatman RJ, Guest D (2009-03-15). "Metabolism of 2-ethylhexanol administered orally and dermally to the female Fischer-344 rat". hero.epa.gov. Archived from the original on 2021-11-22. Retrieved 2021-04-09.
  16. ^ Eastman Kodak Company, Eastman Kodak (2009-03-15). "Pharmacokinetic studies with 2-ethylhexanol in the female fischer 344 rat (final report) with attachments and cover letter dated 050791". hero.epa.gov. Archived from the original on 2021-11-22. Retrieved 2021-04-09.
  17. ^ Pennanen, Sirpa; Tuovinen, Kai; Huuskonen, Hannele; Komulainen, Hannu (1992). "The developmental toxicity of 2-ethylhexanoic acid in Wistar rats". Fundamental and Applied Toxicology. 19 (4): 505–511. doi:10.1016/0272-0590(92)90088-Y. PMID 1426708 – via Elsevier.
  18. ^ "2-Ethylhexanoic acid". ACGIH. Archived from the original on 2021-11-22. Retrieved 2021-04-09.
  19. ^ "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". European Chemicals Agency. 2020. Retrieved 2021-04-09.
  20. ^ "Valproic Acid". The American Society of Health-System Pharmacists. Archived from the original on 2017-07-31. Retrieved Oct 23, 2015.
  21. ^ "Valproate banned without the pregnancy prevention programme". GOV.UK. Archived from the original on 2018-04-24. Retrieved 26 April 2018.
  22. ^ "Rule A-2. Saturated Branched-chain Compounds and Univalent Radicals (ACYCLIC HYDROCARBONS)". acdlabs.com.
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