:2-Ethylhexanoic acid
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477197636
| ImageFile = 2-Ethylhexanoic acid.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 180
| ImageName = Skeletal formula of 2-ethylhexanoic acid
| ImageFile1 = 2-Ethylhexanoic-acid-3D-balls.png
| ImageAlt1 = 2-Ethylhexanoic acid molecule
|Section1={{Chembox Identifiers
| CASNo = 149-57-5
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 72377-05-0
| CASNo1_Ref = {{cascite|changed|??}}
| CASNo1_Comment = S enantiomer
| CASNo2 = 56006-48-5
| CASNo2_Ref = {{cascite|changed|??}}
| CASNo2_Comment = R enantiomer
| PubChem = 8697
| PubChem1 = 78052
| PubChem1_Comment = R
| PubChem2 = 135309
| PubChem2_Comment = S
| ChemSpiderID = 8373
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 70431
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1_Comment = R
| ChemSpiderID2 = 119200
| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID2_Comment = S
| UNII = 01MU2J7VVZ
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 205-743-6
| MeSHName = 2-ethylhexanoic+acid
| ChEMBL = 1162485
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL1 = 1162487
| ChEMBL1_Ref = {{ebicite|changed|EBI}}
| ChEMBL2 = 1162486
| ChEMBL2_Ref = {{ebicite|changed|EBI}}
| RTECS = MO7700000
| Beilstein = 1750468
| SMILES = CCCCC(CC)C(O)=O
| StdInChI = 1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OBETXYAYXDNJHR-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=8 | H=16 | O=2
| Appearance = Colorless liquid
| Density = 903 mg mL−1
| MeltingPtK = 214.15
| BoilingPtK = 501.2
| LogP = 2.579
| VaporPressure = <1 Pa (at 25 °C)
| pKa = 4.819
| pKb = 9.178
| RefractIndex = 1.425
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −635.1 kJ mol−1
| DeltaHc = −4.8013 – 4.7979 MJ mol−1
}}
|Section4={{Chembox Hazards
| GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}} {{GHS health hazard}}
| GHSSignalWord = DANGER
| HPhrases = {{H-phrases|312|318|361}}
| PPhrases = {{P-phrases|280|305+351+338}}
| FlashPtC = 114
| AutoignitionPtC = 371
| ExploLimits = 0.9–6.7%
| LD50 = {{Unbulleted list|1.142 g kg−1 (dermal, rabit)|3 g kg−1 (oral, rat)}}
}}
|Section5={{Chembox Related
| OtherCompounds = {{Unbulleted list|2-Methylhexane|3-Methylhexane|Valnoctamide|2-Methylheptane|3-Methylheptane|2-Ethylhexanol|Valproic acid|Propylheptyl alcohol}}
}}
}}
2-Ethylhexanoic acid (2-EHA), commonly known as octoic acid,{{Cite report |url=https://ntrl.ntis.gov/NTRL/dashboard/searchResults/titleDetail/OTS0512911.xhtml |title=Economic Impact Analysis of Proposed Test Rule for 2-ethylhexanoic Acid (final) (epa Contract No. 68-01-6630). |date=2000 |publisher=Environmental Protection Agency, Washington, DC. Office of Toxic |issue=OTS0512911}} 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.
Production
2-Ethylhexanoic acid is produced industrially from propylene, which is hydroformylated to give butyraldehyde. Aldol condensation of the aldehyde gives 2-ethylhexenal, which is hydrogenated to give 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid.{{Ullmann|first1=Wilhelm|last1=Riemenschneider|title=Carboxylic Acids, Aliphatic|year=2002|doi=10.1002/14356007.a05_235}}
Metal ethylhexanoates
2-Ethylhexanoic acid forms compounds with metal cations that have stoichiometry as metal acetates. These ethylhexanoate complexes are used in organic and industrial chemical synthesis.{{cite journal |doi=10.1039/B614334M |title=Metal 2-Ethylhexanoates and Related Compounds as Useful Precursors in Materials Science |date=2007 |last1=Mishra |first1=Shashank |last2=Daniele |first2=Stéphane |last3=Hubert-Pfalzgraf |first3=Liliane G. |journal=Chemical Society Reviews |volume=36 |issue=11 |pages=1770–1787 |pmid=18213985 }} They function as catalysts in polymerizations as well as for oxidation reactions as "oil drying agents."{{cite journal|title=Synthetic applications of 2-ethylhexanoic acid derived reagents|author1=Raju, Ravinder|author2=Prasad, Kapa|journal=Tetrahedron|year=2012|volume=68|issue=5|pages=1341–1349|doi=10.1016/j.tet.2011.10.078}} They are highly soluble in nonpolar solvents. These metal complexes are often described as salts. They are, however, not ionic but charge-neutral coordination complexes. Their structures are akin to the corresponding acetates.
=Examples of metal ethylhexanoates=
- Hydroxyl aluminium bis(2-ethylhexanoate), used as a thickener
- Tin(II) ethylhexanoate (CAS# 301-10-0), a catalyst for polylactide and poly(lactic-co-glycolic acid).{{cite journal|author1=Coulembier, O.|author2=Degee, P.|author3=Hedrick, J. L.|author4=Dubois, P.|title=Controlled Ring-Opening Polymerization to Biodegradable Aliphatic Polyester: Especially Poly(Β-Malic Acid) Derivatives|journal=Prog. Polym. Sci.|year=2006|volume=31|pages=723–747|doi= 10.1016/j.progpolymsci.2006.08.004}}
- Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins
- Nickel(II) ethylhexanoate (CAS# 4454-16-4){{cite book |doi=10.1002/047084289X.rn014m |chapter=Nickel(II) 2-Ethylhexanoate |title=Encyclopedia of Reagents for Organic Synthesis |date=2001 |last1=Burrows |first1=Cynthia J. |last2=Wey |first2=Shiow-Jyi |isbn=0-471-93623-5 }}
Regulations
2-Ethylhexanoic acid is banned in the EU for use in cosmetics.{{CELEX|id=32023R1490|text=Commission Regulation (EU) 2023/1490 of 19 July 2023 amending Regulation (EC) No 1223/2009 of the European Parliament and of the Council as regards the use in cosmetic products of certain substances classified as carcinogenic, mutagenic or toxic for reproduction}}