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,[4] but it is known as manufactured
E number food additive E355.
 Adipic acid

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

CAS Number 124-04-9  

3D model (JSmol) Interactive image

Interactive image
ChEBI CHEBI:30832  

ChEMBL ChEMBL1157  

ChemSpider 191  

ECHA InfoCard 100.004.250

EC Number 204-673-3

E number E355 (antioxidants, ...)

KEGG D08839  

PubChem CID 196

RTECS number AU8400000

UNII 76A0JE0FKJ  

CompTox Dashboard DTXSID7021605

(EPA)

InChI
InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10) 
Key: WNLRTRBMVRJNCN-UHFFFAOYSA-N 

InChI=1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
Key: WNLRTRBMVRJNCN-UHFFFAOYAY
SMILES
O=C(O)CCCCC(=O)O
C(CCC(=O)O)CC(=O)O
Properties

Chemical formula 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)
Solubility in water 14 g/L (10 °C)
24 g/L (25 °C)
1600 g/L (100 °C)

Solubility Very soluble in

 methanol, ethanol
soluble in acetone
slightly soluble in
cyclohexane
negligible in benzene,
petroleum ether
insoluble in acetic acid
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

Crystal structure Monoclinic

Thermochemistry

Std enthalpy of −994.3 kJ/mol[3]

formation (ΔfH⦵298)
Hazards

Safety data sheet External MSDS

EU classification (DSD) Irritant (Xi)

(outdated)

R-phrases (outdated) R36

NFPA 704 1
2 0

Flash point 196 °C (385 °F; 469 K)

Autoignition 422 °C (792 °F; 695 K)
temperature

Lethal dose or concentration (LD, LC):

LD50 (median dose) 3600 mg/kg (rat)

Related compounds

Related dicarboxylic glutaric acid

acids
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).

 verify (what is   ?)

Infobox references

Preparation and reactivity

Adipic acid is produced from a mixture of
cyclohexanone and cyclohexanol 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:

HOC6H11 + HNO3 → OC(CH2)5 + HNO2 +

H2O

Among its many reactions, the

cyclohexanone is nitrosated, setting the
stage for the scission of the C-C bond:

HNO2 + HNO3 → NO+NO3− + H2O

OC6H10 + NO+ → OC6H9-2-NO + H+

Side products of the method include

glutaric and succinic acids. Nitrous oxide
is produced in about one to one mole ratio
to the adipic acid,[5] as well, via the
intermediacy of a nitrolic acid.[4]

Related processes start from

cyclohexanol, which is obtained from the
hydrogenation of phenol.[4][6]

Alternative methods of
production

Several methods have been developed by

carbonylation of butadiene. For example,
the hydrocarboxylation proceeds as
follows:[4]

CH2=CH−CH=CH2 + 2 CO + 2 H2O →
HO2C(CH2)4CO2H
Another method is oxidative cleavage of
cyclohexene using hydrogen peroxide.[7]
The waste product is water.

Historically, adipic acid was prepared by

oxidation of various fats,[8] thus the name
(ultimately from Latin adeps, adipis –
"animal fat"; cf. adipose tissue).

Reactions

Adipic acid is a dibasic acid (it has two

acidic groups). The pKa values for their
successive deprotonations are 4.41 and
5.41.[9]
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.[10]

Uses
About 60% of the 2.5 billion kg of adipic
acid produced annually is used as
monomer for the production of nylon [11]
by a polycondensation reaction with
hexamethylene diamine forming nylon 66.
Other major applications also involve
polymers; it is a monomer for production
of polyurethane and its esters are
plasticizers, especially in PVC.

In medicine

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.[12]

In foods

Small but significant amounts of adipic

acid are used as a food ingredient as a
flavorant and gelling aid.[13] It is used in
some calcium carbonate antacids to make
them tart. As an acidulant in baking
powders, it avoids the undesirable
hygroscopic properties of tartaric acid.[2]
Adipic acid, rare in nature, does occur
naturally in beets, but this is not an
economical source for commerce
compared to industrial synthesis.[14]

Safety
Adipic acid, like most carboxylic acids, is a
mild skin irritant. It is mildly toxic, with a
median lethal dose of 3600 mg/kg for oral
ingestion by rats.[4]

Environmental
The production of adipic acid is linked to
emissions of N2O,[15] 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:[16]

2 N2O → 2 N2 + O2

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. "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 .
5. Parmon, V. N.; Panov, G. I.; Uriarte, A.;
Noskov, A. S. "Nitrous oxide in
oxidation chemistry and catalysis
application and production". Catalysis
Today. 100 (2005): 115–131.
doi:10.1016/j.cattod.2004.12.012 .
6. Ellis, B. A. (1925). "Adipic Acid" .
Organic Syntheses. 5: 9.; Collective
Volume, 1, p. 560
7. 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): 1646–47.
Bibcode:1998Sci...281.1646S .
doi:10.1126/science.281.5383.1646 .
8. Ince, Walter (1895). "Preparation of
adipic acid and some of its
derivatives" . Journal Chemical
Society, London. 67: 155.
doi:10.1039/CT8956700155 .
 9. Cornils, Boy and Lappe, Peter (2006)
"Dicarboxylic Acids, Aliphatic" in
Ullmann's Encyclopedia of Industrial
Chemistry, Wiley-VCH, Weinheim.
doi:10.1002/14356007.a08_523
10. Thorpe, J. F.; Kon, G. A. R. (1925).
"Cyclopentanone" . Organic Syntheses.
5: 37.; Collective Volume, 1, p. 192
11. "Archived copy" . Archived from the
original on 2015-05-18. Retrieved
2015-05-09. PCI abstract for adipic
acid
12. Roew, Raymond (2009), "Adipic Acid",
Handbook of Pharmaceutical
Excipients, pp. 11–12
13. "Cherry Jell-O Nutrition Facts" . Kraft
Foods. Retrieved 21 Mar 2012.
14. American Chemical Society (9
February 2015). "Molecule of the
Week: Adipic Acid" .
15. US EPA. "U.S. Greenhouse Gas
Inventory Report, Chapter 4. Industrial
Processes" (PDF). Retrieved
2013-11-29.
16. Reimer, R. A.; Slaten, C. S.; Seapan, M.;
Koch, T. A.; Triner, V. G. (2000). "Adipic
Acid Industry — N2O Abatement". Non-
CO2 Greenhouse Gases: Scientific
Understanding, Control and
Implementation. Netherlands:
Springer. pp. 347–358.
doi:10.1007/978-94-015-9343-4_56 .
ISBN 978-94-015-9343-4.

Appendix
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

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

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