Sebacic acid
Sebacic acid is a naturally occurring dicarboxylic acid with the formula (CH2)8(CO2H)2. It is a white flake or powdered solid. Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil.[2]
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IUPAC name
Decanedioic acid | |
Other names
1,8-Octanedicarboxylic acid | |
Identifiers | |
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.003.496 |
EC Number |
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MeSH | C011107 |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C10H18O4 | |
Molar mass | 202.250 g·mol−1 |
Density | 1.209 g/cm3 |
Melting point | 131 to 134.5 °C (267.8 to 274.1 °F; 404.1 to 407.6 K) |
Boiling point | 294.4 °C (561.9 °F; 567.5 K) at 100 mmHg |
0.25 g/L[1] | |
Acidity (pKa) | 4.720, 5.450[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used as a monomer for nylon 610, plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc.
Production
Sebacic acid is produced from castor oil by cleavage of ricinoleic acid, which is obtained from castor oil. Octanol is a byproduct.[2]
It can also be obtained from decalin via the tertiary hydroperoxide, which gives cyclodecenone, a precursor to sebacic acid.[3]
References
- Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t = 25 °C". J. Chem. Eng. Data. 51 (5): 1660–1667. doi:10.1021/je060132t.
- Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.
- Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
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