:2-Ethylhexanoic acid

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| verifiedrevid = 477197636

| ImageFile = 2-Ethylhexanoic acid.png

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| ImageSize = 180

| ImageName = Skeletal formula of 2-ethylhexanoic acid

| ImageFile1 = 2-Ethylhexanoic-acid-3D-balls.png

| ImageAlt1 = 2-Ethylhexanoic acid molecule

| PIN = 2-Ethylhexanoic acid{{Cite web|title=2-ethylhexanoic acid - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8697|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=21 February 2012|location=USA|date=26 March 2005|at=Identification and Related Records}}

|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}}

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|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

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|Section3={{Chembox Thermochemistry

| DeltaHf = −635.1 kJ mol−1

| DeltaHc = −4.8013 – 4.7979 MJ mol−1

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|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)}}

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|Section5={{Chembox Related

| OtherCompounds = {{Unbulleted list|2-Methylhexane|3-Methylhexane|Valnoctamide|2-Methylheptane|3-Methylheptane|2-Ethylhexanol|Valproic acid|Propylheptyl alcohol}}

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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

File:Co(Ethexanoate)2.jpg

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}}

See also

References

{{Reflist}}

{{DEFAULTSORT:Ethylhexanoic acid, 2-}}

Category:Alkanoic acids