Adipic acid

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;
Beilstein Reference	1209788
ChEBI	CHEBI:30832 ;
ChEMBL	ChEMBL1157 ;
ChemSpider	191 ;
ECHA InfoCard	100.004.250
EC Number	204-673-3;
E number	E355 (antioxidants, ...)
Gmelin Reference	3166
KEGG	D08839 ;
PubChem CID	196;
RTECS number	AU8400000;
UNII	76A0JE0FKJ ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID7021605 ;
	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; 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)
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, 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
Crystal structure	Monoclinic
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−994.3 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305+P351+P338, P337+P313
NFPA 704 (fire diamond)	2 1 0
Flash point	196 °C (385 °F; 469 K)
Autoignition; temperature	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

Adipic acid or hexanedioic acid is an organic compound with the chemical formula C₆H₁₀O₄.^[4] It is a white crystalline powder at standard temperature and pressure.^[4] From an industrial perspective, it is the most important dicarboxylic acid at about 2.5 billion kilograms produced annually, mainly as a precursor for the production of nylon.^[4] Adipic acid otherwise rarely occurs in nature,^[5] but it is known as manufactured E number food additive E355. Salts and esters of adipic acid are known as adipates.

^ Mac Gillavry, C. H. (1941). "The crystal structure of adipic acid". Recueil des Travaux Chimiques des Pays-Bas. 60 (8): 605–617. doi:10.1002/recl.19410600805.
^ "Adipic Acid". The Merck Index. Royal Society of Chemistry. 2013. Retrieved 2 March 2017.
^ Haynes, W. M., ed. (2013). CRC Handbook of Chemistry and Physics (94th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4665-7114-3.
^ ^a ^b ^c Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. ABC-CLIO. pp. 20–23. ISBN 978-0-313-33758-1. Archived from the original on 17 June 2016. Retrieved 21 November 2015.
^ Musser, M. T. (2005). "Adipic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_269. ISBN 3527306730.

[1] Mac Gillavry, C. H. (1941). "The crystal structure of adipic acid". Recueil des Travaux Chimiques des Pays-Bas. 60 (8): 605–617. doi:10.1002/recl.19410600805.

[Adipic_Acid-2] "Adipic Acid". The Merck Index. Royal Society of Chemistry. 2013. Retrieved 2 March 2017.

[crc-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.

[Myers-4] Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. ABC-CLIO. pp. 20–23. ISBN 978-0-313-33758-1. Archived from the original on 17 June 2016. Retrieved 21 November 2015.

[Ullmann-5] Musser, M. T. (2005). "Adipic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_269. ISBN 3527306730.

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