Sebacic acid

Sebacic acid
Skeletal formula of sebacic acid
Ball-and-stick model of the sebacic acid molecule
Names
Preferred IUPAC name
Decanedioic acid
Other names
1,8-Octanedicarboxylic acid
Decane-1,10-dioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.496 Edit this at Wikidata
EC Number
  • 203-845-5
MeSH C011107
UNII
  • InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14) ☒N
    Key: CXMXRPHRNRROMY-UHFFFAOYSA-N ☒N
  • InChI=1/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
    Key: CXMXRPHRNRROMY-UHFFFAOYAE
  • OC(=O)CCCCCCCCC(=O)O
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).
☒N verify (what is checkY☒N ?)

Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula HO2C(CH2)8CO2H. 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]

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.

It can be used as a surfactant in the lubricating oil industry to increase the antirust properties of lubricating oils on metals.

  1. ^ a b 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.
  2. ^ Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523. ISBN 3527306730.