2-Ethylhexanol

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2-Ethylhexanol
2-Ethylhexanol 2D.svg
2-Ethylhexanol-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-234-3
KEGG
MeSH 2-ethylhexanol
PubChem CID
UNII
  • InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 Yes check.svgY
    Key: YIWUKEYIRIRTPP-UHFFFAOYSA-N Yes check.svgY
  • CCCCC(CC)CO
Properties
CH3CH2CH2CH2CH(CH2CH3)CH2OH
Molar mass 130.231 g·mol−1
AppearanceColourless 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)
Std molar
entropy (S⦵298)
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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula C H 3CH2CH2CH2CH(CH2CH3)CH2 OH. 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]

Contents

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 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. 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]

2-Ethylhexanol Synthese.png

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 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

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

Related Research Articles

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">Phthalates</span> Any ester derived from phthalic acid

Phthalates, or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften polyvinyl chloride (PVC). Note that while phthalates are usually plasticizers, not all plasticizers are phthalates. The two terms are specific and unique and cannot be used interchangeably.

<span class="mw-page-title-main">Plasticizer</span> Substance added to a material to make it softer and more flexible

A plasticizer is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Methyl acetate</span> Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">Butyraldehyde</span> Chemical compound

Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Bis(2-ethylhexyl) phthalate</span> Organic compound used as a plasticizer to soften polymer matrix

Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, diisooctyl phthalate, DEHP; incorrectly — dioctyl phthalate, DIOP) is an organic compound with the formula C6H4(CO2C8H17)2. DEHP is the most common member of the class of phthalates, which are used as plasticizers. It is the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colorless viscous liquid is soluble in oil, but not in water.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

Ethylhexyl palmitate, also known as octyl palmitate, is the fatty acid ester derived from 2-ethylhexanol and palmitic acid. It is frequently utilized in cosmetic formulations.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

The Guerbet reaction, named after Marcel Guerbet (1861–1938), is an organic reaction that converts a primary alcohol into its β-alkylated dimer alcohol with loss of one equivalent of water. The process is of interest because it converts simple inexpensive feedstocks into more valuable products. Its main disadvantage is that the reaction produces mixtures.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">2-Ethylhexanoic acid</span> Chemical compound

2-Ethylhexanoic acid is the organic compound with the formula CH3(CH2)3CH(C2H5)CO2H. It is a carboxylic acid that is widely used to prepare lipophilic metal derivatives that are soluble in nonpolar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.

<span class="mw-page-title-main">Diethyl phthalate</span> Chemical compound

Diethyl phthalate (DEP) is a phthalate ester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.

<span class="mw-page-title-main">2-Ethyl-1-butanol</span> Chemical compound

2-Ethyl-1-butanol is an organic chemical compound. It can be used to facilitate the separation of ethanol from water, which forms an azeotrope that otherwise limits the maximum ethanol concentration.

<span class="mw-page-title-main">4-Methylcyclohexanemethanol</span> Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

<span class="mw-page-title-main">Bis(2-ethylhexyl)tetrabromophthalate</span> Chemical compound

Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).

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. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0354". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 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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