2-Ethylhexanoic acid

8-Carbon branched fatty acid changed changed 477197636 2-Ethylhexanoic acid.png skin-invert correct ?? 180 Skeletal formula of 2-ethylhexanoic acid 2-Ethylhexanoic-acid-3D-balls.png bg-transparent 2-Ethylhexanoic acid molecule 2-Ethylhexanoic acid2-ethylhexanoic acid - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/8697 PubChem Compound National Center for Biotechnology Information 21 February 2012 USA 26 March 2005 Identification and Related Records 149-57-5 correct CAS 72377-05-0 changed ?? S enantiomer 56006-48-5 changed ?? R enantiomer 8697 78052 R 135309 S 8373 correct chemspider 70431 changed chemspider R 119200 changed chemspider S 01MU2J7VVZ correct FDA 205-743-6 2-ethylhexanoic+acid 1162485 correct EBI 1162487 changed EBI 1162486 changed EBI MO7700000 1750468 CCCCC(CC)C(O)=O 1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) correct chemspider OBETXYAYXDNJHR-UHFFFAOYSA-N correct chemspider 8 16 2 Colorless liquid 903 mg mL−1 214.15 501.2 2.579 <1 Pa (at 25 °C) 4.819 9.178 1.425 −635.1 kJ mol−1 −4.8013 – 4.7979 MJ mol−1 corrosion exclamation mark health hazard DANGER 312 318 361 280 305+351+338 114 371 0.9–6.7% 1.142 g kg−1 (dermal, rabit) 3 g kg−1 (oral, rat) 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,https://ntrl.ntis.gov/NTRL/dashboard/searchResults/titleDetail/OTS0512911.xhtml Economic Impact Analysis of Proposed Test Rule for 2-ethylhexanoic Acid (final) (epa Contract No. 68-01-6630). 2000 Environmental Protection Agency, Washington, DC. Office of Toxic 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. Esters and salts of 2-EHA are called 2-ethylhexanoates, e.g. potassium 2-ethylhexanoate. Production 2-Ethylhexanoic acid is produced industrially from butyraldehyde, which is obtained by hydroformylation of propylene. Aldol condensation of the aldehyde gives 2-ethylhexenal, which is hydrogenated to give 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid.Wilhelm Riemenschneider Carboxylic Acids, Aliphatic 2002 10.1002/14356007.a05_235 Metal ethylhexanoates thumb|left|65% Solution of cobalt(II) bis(2-ethylhexanoate) in mineral spirits, tilted vial to illustrate color and viscosity. Salts, esters, and coordination complexes derived from 2-ethylhexanoic acid are called 2-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.10.1039/B614334M Metal 2-Ethylhexanoates and Related Compounds as Useful Precursors in Materials Science 2007 Mishra Shashank Daniele Stéphane Hubert-Pfalzgraf Liliane G. Chemical Society Reviews 36 11 1770–1787 18213985 They function as catalysts in polymerizations as well as for oxidation reactions as "oil drying agents."Synthetic applications of 2-ethylhexanoic acid derived reagents Raju, Ravinder Prasad, Kapa Tetrahedron 2012 68 5 1341–1349 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).Coulembier, O. Degee, P. Hedrick, J. L. Dubois, P. Controlled Ring-Opening Polymerization to Biodegradable Aliphatic Polyester: Especially Poly(Β-Malic Acid) Derivatives Prog. Polym. Sci. 2006 31 723–747 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)10.1002/047084289X.rn014m Nickel(II) 2-Ethylhexanoate Encyclopedia of Reagents for Organic Synthesis 2001 Burrows Cynthia J. Wey Shiow-Jyi 0-471-93623-5 Regulations 2-Ethylhexanoic acid is banned in the EU for use in cosmetics.32023R1490 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 2-Ethylhexanol References Category:Alkanoic acids