Adipic acid

Adipic acid
Skeletal formula of adipic acid
Ball-and-stick model of the adipic acid molecule
Names
Preferred IUPAC name
Hexanedioic acid
Other names
Adipic acid
Butane-1,4-dicarboxylic acid
Hexane-1,6-dioic acid
1,4-butanedicarboxylic acid
Identifiers
3D model (JSmol)
1209788
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.250 Edit this at Wikidata
EC Number
  • 204-673-3
E number E355 (antioxidants, ...)
3166
KEGG
RTECS number
  • AU8400000
UNII
UN number 3077
  • InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10) checkY
    Key: WNLRTRBMVRJNCN-UHFFFAOYSA-N checkY
  • InChI=1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
    Key: WNLRTRBMVRJNCN-UHFFFAOYAY
  • O=C(O)CCCCC(=O)O
  • C(CCC(=O)O)CC(=O)O
Properties
C6H10O4
Molar mass 146.142 g·mol−1
Appearance White crystals[1]
Monoclinic prisms[2]
Odor Odorless
Density 1.360 g/cm3
Melting point 152.1 °C (305.8 °F; 425.2 K)
Boiling point 337.5 °C (639.5 °F; 610.6 K)
14 g/L (10 °C)
24 g/L (25 °C)
1600 g/L (100 °C)
Solubility Very soluble in methanol, ethanol
soluble in acetone, acetic acid
slightly soluble in cyclohexane
negligible in benzene, petroleum ether
log P 0.08
Vapor pressure 0.097 hPa (18.5 °C) = 0.073 mmHg
Acidity (pKa) 4.43, 5.41
Conjugate base Adipate
Viscosity 4.54 cP (160 °C)
Structure
Monoclinic
Thermochemistry
−994.3 kJ/mol[3]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319
P264, P280, P305+P351+P338, P337+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 196 °C (385 °F; 469 K)
422 °C (792 °F; 695 K)
Lethal dose or concentration (LD, LC):
3600 mg/kg (rat)
Safety data sheet (SDS) External MSDS
Related compounds
glutaric acid
pimelic acid
Related compounds
 hexanoic acid
adipic acid dihydrazide
hexanedioyl dichloride
hexanedinitrile
hexanediamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Adipic acid or hexanedioic acid is the organic compound with the formula (CH2)4(COOH)2. From an industrial perspective, it is the most important dicarboxylic acid: about 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon. Adipic acid otherwise rarely occurs in nature,[4] but it is known as manufactured E number food additive E355. Salts and esters of adipic acid are known as adipates.

  1. ^ Mac Gillavry, C. H. (2010). "The crystal structure of adipic acid". Recueil des Travaux Chimiques des Pays-Bas. 60 (8): 605–617. doi:10.1002/recl.19410600805.
  2. ^ "Adipic Acid". The Merck Index. Royal Society of Chemistry. 2013. Retrieved 2 March 2017.
  3. ^ Haynes, W. M., ed. (2013). CRC Handbook of Chemistry and Physics (94th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4665-7114-3.
  4. ^ Musser, M. T. (2005). "Adipic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_269. ISBN 3527306730.