Adipic acid

Adipic 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.[2]

Historically, adipic acid was prepared by oxidation of various fats,[5] thus the name (ultimately from Latin adeps,
adipis : 'animal fat'; cf. adipose tissue).

1.2 Reactions
Adipic acid is a dibasic acid (can be deprotonated twice).
Its pKs are 4.41 and 5.41.[6]

Preparation and reactivity

With the carboxylate groups separated by four methylene

groups, adipic acid is suited for intramolecular condensation reactions. Upon treatment with barium hydroxide at
elevated temperatures, it undergoes ketonization to give
cyclopentanone.[7]

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:

2 Uses

HOC6 H11 + HNO3 OC6 H10 + HNO2 +

H2 O

About 60% of the 2.5 billion kg of adipic acid produced

Among its many reactions, the cyclohexanone is ni- annually is used as monomer for the production of nylon
trosated, setting the stage for the scission of the C-C [8] by a polycondensation reaction with hexamethylene
bond:
diamine forming nylon 66. Other major applications
also involve polymers: it is a monomer for production of
HNO2 + HNO3 NO+ NO3 + H2 O
Polyurethane and its esters are plasticizers, especially in
PVC.
OC6 H10 + NO+ OC6 H9 2-NO + H+
Side products of the method include glutaric and succinic
acids.[2]
2.1 In medicine
Related processes start from cyclohexanol, which is obAdipic acid has been incorporated into controlled-release
tained from the hydrogenation of phenol.[2][3]
formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. It
1.1 Alternative methods of production
has also been incorporated into the polymeric coating of
hydrophilic monolithic systems to modulate the intragel
Several methods have been developed by carbonylation pH, resulting in zero-order release of a hydrophilic drug.
of butadiene. For example, the hydrocarboxylation pro- The disintegration at intestinal pH of the enteric polymer
ceeds as follows:[2]
shellac has been reported to improve when adipic acid
was used as a pore-forming agent without aecting reCH2 =CH-CH=CH2 + 2 CO + 2 H2 O
lease in the acidic media. Other controlled-release forHO2 C(CH2 )4 CO2 H
mulations have included adipic acid with the intention of
obtaining a late-burst release prole.[9]
See also: Heteropoly acid

2.2 In foods

A method 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.

Small but signicant amounts of adipic acid are used as a

food ingredient as a avorant and gelling aid.[10] It is used
in some calcium carbonate antacids to make them tart.
1

Safety

EXTERNAL LINKS

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.[2]

[12] Reimer, R. A.; Slaten, C. S.; Seapan, M.; Koch, T. A.

and Triner, V. G. (2000). Adipic Acid Industry N2 O
Abatement. Non-CO2 Greenhouse Gases: Scientic Understanding, Control and Implementation. Netherlands:
Springer. pp. 347358. doi:10.1007/978-94-015-93434_56. ISBN 978-94-015-9343-4.

6 Appendix

Environmental

The production of adipic acid is linked to emissions of N

2O,[11] a potent greenhouse gas and cause of stratospheric
ozone depletion. At adipic acid producers DuPont and
Rhodia (now Invista and Solvay respectively), processes
have been implemented to catalytically convert the nitrous oxide to innocuous products:[12]
2 N2 O 2 N 2 + O 2

References

[1] Mac Gillavry, C. H. (2010). The crystal structure of

adipic acid. Recueil des Travaux Chimiques des Pays-Bas
60 (8): 605. doi:10.1002/recl.19410600805.
[2] Musser, M. T. (2005). Adipic Acid. Ullmanns Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.
doi:10.1002/14356007.a01_269.
[3] Ellis, B. A. (1925). Adipic Acid. Org. Synth. 5: 9.;
Coll. Vol. 1, p. 560
[4] 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): 164647. Bibcode:1998Sci...281.1646S.
doi:10.1126/science.281.5383.1646.
[5] Ince, Walter (1895). Preparation of adipic acid and some
of its derivatives. Journal Chemical Society, London 67:
155. doi:10.1039/CT8956700155.
[6] Cornils, Boy and Lappe, Peter (2006) Dicarboxylic Acids, Aliphatic in Ullmanns Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.
doi:10.1002/14356007.a08_523
[7] Thorpe, J. F. and Kon, G. A. R. (1925).
Cyclopentanone. Org. Synth. 5: 37.; Coll. Vol.
1, p. 192
[8] http://pcinylon.com/index.php/markets-covered/
adipic-acid PCI abstract for adipic acid
[9] Roew, Raymond (2009), Adipic Acid, Handbook of
Pharmaceutical Excipients, pp. 1112
[10] Cherry Jell-O Nutrition Facts. Kraft Foods. Retrieved
21 Mar 2012.
[11] US EPA. U.S. Greenhouse Gas Inventory Report, Chapter 4. Industrial Processes (PDF). Retrieved 2013-11-29.

E-number E355.
U.S. 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)
European Union Citations Decision 1999/217/EC
Flavoing Substance; Directive 95/2/EC, Annex IV
Permitted Food Additive; 2002/72/EC, Annex A
Authorized monomer for Food Contact Plastics

7 External links
International Chemical Safety Card 0369
SIDS Initial Assessment Report for Adipic acid
from the Organisation for Economic Co-operation
and Development (OECD)
adipic acid on chemicalland
Solutia Inc product website

Text and image sources, contributors, and licenses

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