Adipic acid
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, but it is known as manufactured E number food additive E355. Salts and esters of adipic acid are known as adipates.
| 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 |
| EC Number |
|
| E number | E355 (antioxidants, ...) |
| 3166 | |
| KEGG | |
PubChem CID |
|
| RTECS number |
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| UNII | |
| UN number | 3077 |
CompTox Dashboard (EPA) |
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SMILES
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| Properties | |
| C6H10O4 | |
| Molar mass | 146.142 g·mol−1 |
| Appearance | White crystals Monoclinic prisms |
| 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 | |
Std enthalpy of formation (ΔfH⦵298) |
−994.3 kJ/mol |
| Hazards | |
| GHS labelling: | |
| Warning | |
| H319 | |
| P264, P280, P305+P351+P338, P337+P313 | |
| NFPA 704 (fire diamond) |
2
1
0 |
| Flash point | 196 °C (385 °F; 469 K) |
| 422 °C (792 °F; 695 K) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
3600 mg/kg (rat) |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Related dicarboxylic acids |
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).
Infobox references | |
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