| Adipic acid | |
|---|---|
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hexanedioic acid |
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Other names
hexane-1,6-dioic acid |
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| Identifiers | |
| CAS number | 124-04-9 |
| PubChem | 196 |
| ChemSpider | 191 |
| UNII | 76A0JE0FKJ |
| EC-number | 204-673-3 |
| KEGG | D08839 |
| ChEBI | CHEBI:30832 |
| ChEMBL | CHEMBL1157 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C6H10O4 |
| Molar mass | 146.14 g mol−1 |
| Appearance | White crystals (monoclinic)[1] |
| Density | 1.36 g/cm3 |
| Melting point |
152.1 °C, 425 K, 306 °F |
| Boiling point |
337.5 °C, 611 K, 640 °F |
| Solubility in water | fairly soluble[2] |
| Acidity (pKa) | 4.43, 5.41 |
| Hazards | |
| MSDS | External MSDS |
| EU Index | 607-144-00-9 |
| EU classification | Irritant (Xi) |
| R-phrases | R36 |
| NFPA 704 |
1
2
0
|
| Flash point | 196 °C |
| Autoignition temperature |
422 °C |
| LD50 | 3600 mg/kg (rat) |
| Related compounds | |
| Related dicarboxylic acids | glutaric acid pimelic acid |
| Related compounds | hexanoic acid adipic acid dihydrazide |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Adipic acid is the organic compound with the formula (CH2)4(COOH)2. From the 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.[3]
Contents |
Historically, adipic acid was prepared from various fats using oxidation. Currently adipic acid is produced from a mixture of cyclohexanol and cyclohexanone called "KA oil", the abbreviation of "ketone-alcohol oil." The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction the cyclohexanol is converted to the ketone, releasing nitrous acid:
Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C-C bond:
Side products of the method include glutaric and succinic acids.[3]
Related processes start from cyclohexanol, which is obtained from the hydrogenation of phenol.[3]
Several methods have been developed by carbonylation of butadiene. For example, the hydrocarboxylation proceeds as follows:[3]
A method has been reported that utilizes principles of green chemistry in that water is the only by-product. Cyclohexene is oxidized with hydrogen peroxide using a tungstate-based catalyst and a phase transfer catalyst.[4] The waste product is water.
By far the majority of the 2.5 billion kg of adipic acid produced annually is used as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon. Other major applications also involve polymers: it is a monomer for production of Polyurethane and its esters are plasticizers, especially in PVC.
Adipic acid has been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. It has also been incorporated into the polymeric coating of hydrophilic monolithic systems to modulate the intragel pH, resulting in zero-order release of a hydrophilic drug. The disintegration at intestinal pH of the enteric polymer shellac has been reported to improve when adipic acid was used as a pore-forming agent without affecting release in the acidic media. Other controlled-release formulations have included adipic acid with the intention of obtaining a late-burst release profile.[5]
Small but significant amounts of adipic acid are used as a food ingredient as a flavorant and gelling aid. It is used in some calcium carbonate antacids to make them tart.
Adipic acid, like most carboxylic acids, is a mild skin irritant. It is mildly toxic, with an LD50 of 3600 mg/kg for oral ingestion by rats.[3]