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.
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 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid.[2]
Metal ethylhexanoatesedit
65% Solution of cobalt(II) bis(2-ethylhexanoate) in mineral spirits, tilted vial to illustrate color and viscosity.
^"2-ethylhexanoic acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 21 February 2012.
^Mishra, Shashank; Daniele, Stéphane; Hubert-Pfalzgraf, Liliane G. (2007). "Metal 2-Ethylhexanoates and Related Compounds as Useful Precursors in Materials Science". Chemical Society Reviews. 36 (11): 1770–1787. doi:10.1039/B614334M. PMID 18213985.
^Coulembier, O.; Degee, P.; Hedrick, J. L.; Dubois, P. (2006). "Controlled Ring-Opening Polymerization to Biodegradable Aliphatic Polyester: Especially Poly(Β-Malic Acid) Derivatives". Prog. Polym. Sci. 31: 723–747. doi:10.1016/j.progpolymsci.2006.08.004.
January 01, 1970
ethylhexanoic, acid, organic, compound, with, formula, c2h5, co2h, carboxylic, acid, that, widely, used, prepare, lipophilic, metal, derivatives, that, soluble, nonpolar, organic, solvents, colorless, viscous, supplied, racemic, mixture, names, preferred, iupa. 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 2 Ethylhexanoic acid Names Preferred IUPAC name 2 Ethylhexanoic acid 1 Identifiers CAS Number 149 57 5 Y72377 05 0 S enantiomer N56006 48 5 R enantiomer N 3D model JSmol Interactive image Beilstein Reference 1750468 ChEMBL ChEMBL1162485 YChEMBL1162487 NChEMBL1162486 N ChemSpider 8373 Y70431 R N119200 S N ECHA InfoCard 100 005 222 EC Number 205 743 6 MeSH 2 ethylhexanoic acid PubChem CID 869778052 R135309 S RTECS number MO7700000 UNII 01MU2J7VVZ Y CompTox Dashboard EPA DTXSID9025293 InChI InChI 1S C8H16O2 c1 3 5 6 7 4 2 8 9 10 h7H 3 6H2 1 2H3 H 9 10 YKey OBETXYAYXDNJHR UHFFFAOYSA N Y SMILES CCCCC CC C O O Properties Chemical formula C 8H 16O 2 Molar mass 144 214 g mol 1 Appearance Colorless liquid Density 903 mg mL 1 Melting point 59 00 C 74 20 F 214 15 K Boiling point 228 1 C 442 5 F 501 2 K log P 2 579 Vapor pressure lt 1 Pa at 25 C Acidity pKa 4 819 Basicity pKb 9 178 Refractive index nD 1 425 Thermochemistry Std enthalpy offormation DfH 298 635 1 kJ mol 1 Std enthalpy ofcombustion DcH 298 4 8013 4 7979 MJ mol 1 Hazards GHS labelling Pictograms Signal word Danger Hazard statements H312 H318 H361 Precautionary statements P280 P305 P351 P338 Flash point 114 C 237 F 387 K Autoignitiontemperature 371 C 700 F 644 K Explosive limits 0 9 6 7 Lethal dose or concentration LD LC LD50 median dose 1 142 g kg 1 dermal rabit 3 g kg 1 oral rat Related compounds Related compounds 2 Methylhexane3 MethylhexaneValnoctamide2 Methylheptane3 Methylheptane2 EthylhexanolValproic acidPropylheptyl alcohol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Production 2 Metal ethylhexanoates 2 1 Examples of metal ethylhexanoates 3 See also 4 ReferencesProduction edit2 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 2 ethylhexanal Oxidation of this aldehyde gives the carboxylic acid 2 Metal ethylhexanoates edit nbsp 65 Solution of cobalt II bis 2 ethylhexanoate in mineral spirits tilted vial to illustrate color and viscosity 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 3 They function as catalysts in polymerizations as well as for oxidation reactions as oil drying agents 4 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 edit 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 5 Cobalt II ethylhexanoate CAS 136 52 7 a drier for alkyd resins Nickel II ethylhexanoate CAS 4454 16 4 See also edit2 EthylhexanolReferences edit 2 ethylhexanoic acid Compound Summary PubChem Compound USA National Center for Biotechnology Information 26 March 2005 Identification and Related Records Retrieved 21 February 2012 Riemenschneider Wilhelm 2002 Carboxylic Acids Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a05 235 ISBN 978 3527306732 Mishra Shashank Daniele Stephane Hubert Pfalzgraf Liliane G 2007 Metal 2 Ethylhexanoates and Related Compounds as Useful Precursors in Materials Science Chemical Society Reviews 36 11 1770 1787 doi 10 1039 B614334M PMID 18213985 Raju Ravinder Prasad Kapa 2012 Synthetic applications of 2 ethylhexanoic acid derived reagents Tetrahedron 68 5 1341 1349 doi 10 1016 j tet 2011 10 078 Coulembier O Degee P Hedrick J L Dubois P 2006 Controlled Ring Opening Polymerization to Biodegradable Aliphatic Polyester Especially Poly B Malic Acid Derivatives Prog Polym Sci 31 723 747 doi 10 1016 j progpolymsci 2006 08 004 Retrieved from https en wikipedia org w index php title 2 Ethylhexanoic acid amp oldid 1211124117, wikipedia, wiki, book, books, library,
