Sebacic acid

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Sebacic acid
Skeletal formula of sebacic acid
Ball-and-stick model of the sebacic acid molecule
Names
IUPAC name
Decanedioic acid
Other names
1,8-Octanedicarboxylic acid
Identifiers
111-20-6 YesY
ChEBI CHEBI:CHEBI:41865 N
ChemSpider 5004 N
EC number 203-845-5
Jmol-3D images Image
MeSH C011107
PubChem 5192
Properties
C10H18O4
Molar mass 202.25 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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Sebacic acid is a naturally occurring dicarboxylic acid with the structure (HOOC)(CH2)8(COOH).

In its pure state it is a white flake or powdered crystal. The product is described as non-hazardous, though in its powdered form it can be prone to flash ignition (a typical risk in handling fine organic powders).

Sebaceus is Latin for tallow candle, sebum (tallow) is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil, with the vast majority of world production occurring in China which annually exports over 100,000 metric tonnes, representing over 90% of global trade of the product.[citation needed]

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. Sebacic acid is also used as an intermediate for aromatics, antiseptics, and painting materials.

Sebacic acid is produced from castor oil by using sodium hydroxide, sulfuric acid with catalysts including zinc oxide and phenol.[citation needed] Byproducts include glycerol, octanol and polymer residue.

References[edit]

  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. 

External links[edit]