Adipic acid

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Template:Chembox E numberTemplate:Chembox SolubilityInWater
Adipic acid
IUPAC name hexanedioic acid
Other names butane-1,4-dicarboxylic acid
Identifiers
3D model (JSmol)
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Properties
C6H10O4
Molar mass 146.14 g/mol
Appearance White crystals
Density 1.36 g/cm³
Melting point
Boiling point
Hazards
Main hazards flammable
R-phrases R: R36
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Adipic acid (IUPAC systematic name: hexanedioic acid) is a chemical compound of the class of carboxylic acids. It is a white crystalline powder appearing as an acid in aqueous circumstances, though it is not highly soluble.

Preparation

Historically, adipic acid is prepared from various fats using oxidation. Current commercial adipic acid is produced from cyclohexane by two oxidation steps.

  1. Cyclohexane + O2cyclohexanol and cyclohexanone
  2. cyclohexanol/cyclohexanone + nitric acid + air → adipic acid + nitrous oxide

(The mixture of cyclohexanol and cyclohexanone produced from cyclohexane is commercially called "KA oil", the abbreviation of "Ketone-Alcohol oil".)

Utilizing Principles of Green chemistry, a new method of synthesis involves:

Cyclohexene + hydrogen peroxide with a tungsten catalyst under phase transfer conditions to produce adipic acid.[1] The waste product is water.

Uses

By far the main use of adipic acid is as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon, the most common form of nylon. Other uses include:

  • reactant to form plasticizers and lubricant components
  • Food Ingredient as a flavorant and gelling aid.E-number E355.
  • FDA citations - GRAS (21 CFR 184.1009), Indirect additive (21 CFR 175.300, 21 CFR 175.320, 21 CFR 176.170, 21 CFR 176.180, 21 CFR 177.1200, 21 CFR 177.1390 , 21 CFR 177.1500, 21 CFR 177.1630 , 21 CFR 177.1680, 21 CFR 177.2420, 21 CFR 177.2600)

References

  1. Sato K, Aoki M, Noyori R (1998). "A "Green" route to adipic acid: direct oxidation of cyclohexenes with 30 percent hydrogen peroxide". Science. 281 (5383): 1646–7. PMID 9733504.

External links

cs:Kyselina adipová de:Adipinsäure it:Acido adipico lv:Adipīnskābe nl:Adipinezuur fi:Adipiinihappo


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