| Revision as of 15:34, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 469312175 of page 2-Ethylhexanoic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 22:10, 21 November 2024 edit Marc Schroeder (talk | contribs)Extended confirmed users1,636 editsmNo edit summary |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| Verifiedfields = changed |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 413109808 |
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| verifiedrevid = 477197636 |
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| ImageFile = 2-Ethylhexanoic acid.png |
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| ImageFile = 2-Ethylhexanoic acid.png |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = 200px |
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| ImageSize = 180 |
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| IUPACName = 2-Ethylhexanoic acid |
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| ImageName = Skeletal formula of 2-ethylhexanoic acid |
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| OtherNames = 2-Ethylcaproic acid; 3-Heptanecarboxylic acid |
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| ImageFile1 = 2-Ethylhexanoic-acid-3D-balls.png |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = 2-Ethylhexanoic acid molecule |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = 2-Ethylhexanoic acid<ref>{{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}}</ref> |
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|Section1={{Chembox Identifiers |
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| CASNo = 149-57-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 72377-05-0 |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| CASNo1_Comment = <small>''S'' enantiomer</small> |
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| CASNo2 = 56006-48-5 |
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| CASNo2_Ref = {{cascite|changed|??}} |
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| CASNo2_Comment = <small>''R'' enantiomer</small> |
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| PubChem = 8697 |
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| PubChem1 = 78052 |
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| PubChem1_Comment = <small>''R''</small> |
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| PubChem2 = 135309 |
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| PubChem2_Comment = <small>''S''</small> |
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| ChemSpiderID = 8373 |
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| ChemSpiderID = 8373 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1 = 70431 |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1_Comment = <small>''R''</small> |
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| ChemSpiderID2 = 119200 |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2_Comment = <small>''S''</small> |
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| UNII = 01MU2J7VVZ |
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| UNII = 01MU2J7VVZ |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) |
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| EINECS = 205-743-6 |
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| InChIKey = OBETXYAYXDNJHR-UHFFFAOYAO |
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| MeSHName = 2-ethylhexanoic+acid |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1162485 |
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| ChEMBL = 1162485 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL1 = 1162487 |
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| ChEMBL1_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL2 = 1162486 |
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| ChEMBL2_Ref = {{ebicite|changed|EBI}} |
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| RTECS = MO7700000 |
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| Beilstein = 1750468 |
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| SMILES = CCCCC(CC)C(O)=O |
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| StdInChI = 1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) |
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| StdInChI = 1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OBETXYAYXDNJHR-UHFFFAOYSA-N |
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| StdInChIKey = OBETXYAYXDNJHR-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo = 149-57-5 |
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|Section2={{Chembox Properties |
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| PubChem = 8697 |
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| SMILES = O=C(O)C(CC)CCCC |
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| C=8 | H=16 | O=2 |
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| Appearance = Colorless liquid |
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| Density = 903 mg mL<sup>−1</sup> |
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| MeltingPtK = 214.15 |
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| BoilingPtK = 501.2 |
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| LogP = 2.579 |
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| VaporPressure = <1 Pa (at 25 °C) |
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| pKa = 4.819 |
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| pKb = 9.178 |
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| RefractIndex = 1.425 |
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}} |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −635.1 kJ mol<sup>−1</sup> |
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| DeltaHc = -4.8013–4.7979 MJ mol<sup>−1</sup> |
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}} |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}} {{GHS health hazard}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|312|318|361}} |
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| PPhrases = {{P-phrases|280|305+351+338}} |
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| FlashPtC = 114 |
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| AutoignitionPtC = 371 |
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| ExploLimits = 0.9–6.7% |
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| LD50 = {{Unbulleted list|1.142 g kg<sup>−1</sup> <small>(dermal, rabit)</small>|3 g kg<sup>−1</sup> <small>(oral, rat)</small>}} |
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}} |
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|Section5={{Chembox Related |
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| OtherCompounds = {{Unbulleted list|]|]|]|]|]|]|]|]}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| C=8|H=16|O=2 |
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| Appearance = Colorless oil |
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| Density = 0.903 g/cm<sup>3</sup>, solid |
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| MeltingPtC = -59 |
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| BoilingPtC = 228 |
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| Solubility = Low |
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| SolubleOther = Soluble in many organic solvents |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Flammable |
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| FlashPt = 110 °C (230 °F) |
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| Autoignition = 371 °C |
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| RPhrases = {{R63}} |
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| SPhrases = {{S36/37}} |
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}} |
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| Section4 = {{Chembox Related |
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| OtherFunctn = |
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| Function = ligand precursor |
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| OtherCpds = ], ] |
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}} |
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'''2-Ethylhexanoic acid''' (2-EHA), commonly known as '''octoic acid''',<ref>{{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}}</ref> is the ] with the ] CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CH(C<sub>2</sub>H<sub>5</sub>)CO<sub>2</sub>H. It is a ] 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 ]. |
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==Production== |
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2-Ethylhexanoic acid is produced industrially from ], which is ] to give ]. ] of the aldehyde gives 2-ethylhexenal, which is hydrogenated to give ]. Oxidation of this aldehyde gives the carboxylic acid.<ref>{{Ullmann|first1=Wilhelm|last1=Riemenschneider|title=Carboxylic Acids, Aliphatic|year=2002|doi=10.1002/14356007.a05_235}}</ref> |
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==Metal ethylhexanoates== |
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] |
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2-Ethylhexanoic acid forms compounds with metal cations that have stoichiometry as ]s. These ethylhexanoate complexes are used in ] and ].<ref>{{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 }}</ref> They function as ]s in ]izations as well as for ] reactions as "]s."<ref>{{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}}</ref> They are highly soluble in nonpolar solvents. These metal complexes are often described as salts. They are, however, not ionic but charge-neutral ]. Their structures are akin to the corresponding ]s. |
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===Examples of metal ethylhexanoates=== |
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* ], used as a thickener |
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* ] (CAS# 301-10-0), a catalyst for ] and ].<ref>{{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}}</ref> |
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* Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins |
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* Nickel(II) ethylhexanoate (CAS# 4454-16-4)<ref>{{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 }}</ref> |
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== Regulations == |
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2-Ethylhexanoic acid is banned in the EU for use in cosmetics.<ref>{{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}}</ref> |
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==See also== |
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* ] |
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==References== |
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{{Reflist}} |
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{{DEFAULTSORT:Ethylhexanoic acid, 2-}} |
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] |
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] |