2-Ethylhexanol

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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)
Std enthalpy of
formation
(ΔfH⦵298)
 −433.67–−432.09 kJ/mol
Std enthalpy of
combustion
(ΔcH⦵298)
 −5.28857–−5.28699 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Mildly toxic
GHS labelling:
GHS02: Flammable 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).
☒N verify (what is checkY☒N ?)

2-Ethylhexanol (abbreviated 2-EH) is an

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

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

esterification of three 2-ethylhexanol per trimellitic acid
.

It is also commonly used as a low volatility solvent. 2-Ethylhexanol can also be used as a cetane improver when reacted with nitric acid. 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

2-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.[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

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

valproic acid, has been well established.[17][18][19][20][21]

Nomenclature

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

References

  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. ^
    ISBN 978-3-527-30673-2
    .
  4. PMID 16569063
    .
  5. S2CID 97102092
    .
  6. doi:10.1016/S0957-4166(00)86137-6
    .
  7. PMID 20659633
    .
  8. ^ "Product Spotlight: 2-Ethylhexanol". December 12, 2019.
  9. ISBN 978-3-527-30673-2
    .
  10. ^ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-4181.
  11. doi:10.1021/ie50613a027
    .
  12. PMID 20409194
    .
  13. 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. 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.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=2-Ethylhexanol&oldid=1219478100"