Lauric acid

"Laurate" redirects here. For the honorary title, see Laureate.
Lauric acid
Skeletal formula of lauric acid
Names
Preferred IUPAC name
Dodecanoic acid
Other names
n-Dodecanoic acid, Dodecylic acid, Dodecoic acid, Laurostearic acid, Vulvic acid, 1-Undecanecarboxylic acid, Duodecylic acid, C12:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.075 Edit this at Wikidata
EC Number
  • 205-582-1
KEGG
UNII
  • InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) ☒N
    Key: POULHZVOKOAJMA-UHFFFAOYSA-N ☒N
  • InChI=1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
    Key: POULHZVOKOAJMA-UHFFFAOYAP
  • O=C(O)CCCCCCCCCCC
Properties
C12H24O2
Molar mass 200.322 g·mol−1
Appearance White powder
Odor Slight odor of bay oil
Density 1.007 g/cm3 (24 °C)[1]
0.8744 g/cm3 (41.5 °C)[2]
0.8679 g/cm3 (50 °C)[3]
Melting point 43.8 °C (110.8 °F; 316.9 K)[3]
Boiling point 297.9 °C (568.2 °F; 571.0 K)
282.5 °C (540.5 °F; 555.6 K)
at 512 mmHg[1]
225.1 °C (437.2 °F; 498.2 K)
at 100 mmHg[3][4]
37 mg/L (0 °C)
55 mg/L (20 °C)
63 mg/L (30 °C)
72 mg/L (45 °C)
83 mg/L (100 °C)[5]
Solubility Soluble in alcohols, diethyl ether, phenyls, haloalkanes, acetates[5]
Solubility in methanol 12.7 g/100 g (0 °C)
120 g/100 g (20 °C)
2250 g/100 g (40 °C)[5]
Solubility in acetone 8.95 g/100 g (0 °C)
60.5 g/100 g (20 °C)
1590 g/100 g (40 °C)[5]
Solubility in ethyl acetate 9.4 g/100 g (0 °C)
52 g/100 g (20°C)
1250 g/100 g (40°C)[5]
Solubility in toluene 15.3 g/100 g (0 °C)
97 g/100 g (20°C)
1410 g/100 g (40°C)[5]
log P 4.6[6]
Vapor pressure 2.13·10−6 kPa (25 °C)[6]
0.42 kPa (150 °C)[4]
6.67 kPa (210 °C)[7]
Acidity (pKa) 5.3 (20 °C)[6]
Thermal conductivity 0.442 W/m·K (solid)[2]
0.1921 W/m·K (72.5 °C)
0.1748 W/m·K (106 °C)[1]
1.423 (70 °C)[1]
1.4183 (82 °C)[3]
Viscosity 6.88 cP (50 °C)
5.37 cP (60 °C)[2]
Structure
Monoclinic (α-form)[8]
Triclinic, aP228 (γ-form)[9]
P21/a, No. 14 (α-form)[8]
P1, No. 2 (γ-form)[9]
2/m (α-form)[8]
1 (γ-form)[9]
a = 9.524 Å, b = 4.965 Å, c = 35.39 Å (α-form)[8]
α = 90°, β = 129.22°, γ = 90°
Thermochemistry
404.28 J/mol·K[4]
−775.6 kJ/mol[6]
7377 kJ/mol
7425.8 kJ/mol (292 K)[4]
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H412[7]
P273[7]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
1
1
Flash point > 113 °C (235 °F; 386 K)[7]
Related compounds
Related compounds
 Glyceryl laurate
Related compounds
Related compounds
 Undecanoic acid
Tridecanoic acid
Dodecanol
Dodecanal
Sodium lauryl sulfate
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 ?)

Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids.[6] It is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and esters of lauric acid are known as laurates.

  1. ^ a b c d G., Chuah T.; D., Rozanna; A., Salmiah; Y., Thomas Choong S.; M., Sa'ari (2006). "Fatty acids used as phase change materials (PCMs) for thermal energy storage in building material applications" (PDF). University Putra Malaysia. Archived from the original (PDF) on 2014-11-03. Retrieved 2014-06-22.
  2. ^ a b c Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering data on mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN 0-444-82802-8.
  3. ^ a b c d Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  4. ^ a b c d Dodecanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-14)
  5. ^ a b c d e f Seidell, Atherton; Linke, William F. (1952). Solubilities of inorganic and organic compounds (3rd ed.). New York: D. Van Nostrand Company. pp. 742–743.
  6. ^ a b c d e CID 3893 from PubChem
  7. ^ a b c d Sigma-Aldrich Co., Lauric acid. Retrieved on 2014-06-14.
  8. ^ a b c d Vand, V.; Morley, W. M.; Lomer, T. R. (1951). "The crystal structure of lauric acid". Acta Crystallographica. 4 (4): 324–329. Bibcode:1951AcCry...4..324V. doi:10.1107/S0365110X51001069.
  9. ^ a b c Sydow, Erik von (1956). "On the structure of the crystal form A of lauric acid" (PDF). actachemscand.org. Acta Chemica Scandinavica. Retrieved 2014-06-14.