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Adipic acid information


Adipic acid
Skeletal formula of adipic acid
Ball-and-stick model of the adipic acid molecule
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 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
Beilstein Reference
1209788
ChEBI
  • CHEBI:30832 checkY
ChEMBL
  • ChEMBL1157 checkY
ChemSpider
  • 191 checkY
ECHA InfoCard 100.004.250 Edit this at Wikidata
EC Number
  • 204-673-3
E number E355 (antioxidants, ...)
Gmelin Reference
3166
KEGG
  • D08839 checkY
PubChem CID
  • 196
RTECS number
  • AU8400000
UNII
  • 76A0JE0FKJ checkY
UN number 3077
CompTox Dashboard (EPA)
  • DTXSID7021605 Edit this at Wikidata
InChI
  • InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10) checkY
    Key: WNLRTRBMVRJNCN-UHFFFAOYSA-N checkY
  • 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, 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 fH298)
−994.3 kJ/mol[3]
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H319
Precautionary statements
P264, P280, P305+P351+P338, P337+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 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. Salts and esters of adipic acid are known as adipates.

  1. ^ Mac Gillavry, C. H. (2010). "The crystal structure of adipic acid". Recueil des Travaux Chimiques des Pays-Bas. 60 (8): 605–617. 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. ISBN 3527306730.

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Adipic acid

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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...

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Adipic acid dihydrazide

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Adipic acid dihydrazide (ADH) is a chemical used for cross-linking water-based emulsions. It can also be used as a hardener for certain epoxy resins....

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Dicarboxylic acid

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dicarboxylic acid in the industry is adipic acid, which is a precursor in the production of nylon. Other examples of dicarboxylic acids include aspartic acid and...

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Adiponitrile

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NCCH2CH=CHCH2CN + H2 → NC(CH2)4CN Adiponitrile has also been produced from adipic acid, by dehydration of the diamide, but this is rarely employed. After patent...

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Pimelic acid

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Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Pimelic acid is one CH 2 unit longer than a related dicarboxylic acid, adipic acid, a...

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Muconic acid

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benzene. Synthetically, trans,trans-muconic acid can be prepared from adipic acid. cis,cis-Muconic acid is produced by some bacteria by the enzymatic...

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Nitrolic acid

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dioxide. Adipic acid is a precursor to many nylon polymers. In the end, nitrous oxide is produced in about one to one mole ratio to the adipic acid. Matt...

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Polybutylene adipate terephthalate

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biodegradable random copolymer, specifically a copolyester of adipic acid, 1,4-butanediol and terephthalic acid. PBAT is produced by many different manufacturers...

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Acetylated distarch adipate

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starches. This is a starch that is treated with acetic anhydride and adipic acid anhydride to resist high temperatures. No acceptable daily intake for...

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Nylon 66

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polycondensation of hexamethylenediamine and adipic acid. Equivalent amounts of hexamethylenediamine and adipic acid are combined in water. In the original...

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Nitrous acid

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oxidized to a carboxylic acid, or reduced to form amines. This process is used in the commercial production of adipic acid. Nitrous acid reacts rapidly with...

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Nitric acid

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nylon, adipic acid, is produced on a large scale by oxidation of "KA oil"—a mixture of cyclohexanone and cyclohexanol—with nitric acid. Nitric acid has been...

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Mucic acid

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can be used to replace tartaric acid in self-raising flour or fizzies. It has been used as a precursor of adipic acid in the way to nylon by a rhenium-catalyzed...

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Cyclohexane

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sometimes used). Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon. Cyclohexyl (C6H11) is...

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Adipoyl chloride

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colorless liquid. It reacts with water to give adipic acid. It is prepared by treatment of adipic acid with thionyl chloride. Adipoyl chloride reacts...

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Carboxylic acid

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adipic acid (polymers), citric acid (a flavor and preservative in food and beverages), ethylenediaminetetraacetic acid (chelating agent), fatty acids...

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List of carboxylic acids

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Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature...

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Thermoplastic polyurethane

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on soft segment chemistry: polyester-based TPUs (mainly derived from adipic acid esters) polyether-based TPUs (mainly based on tetrahydrofuran (THF) ethers)...

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Dioctyl adipate

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been used for bis(2-ethylhexyl) adipate (CAS # 103-23-1). Esters of adipic acid exhibit low acute toxicities in animal models. The LD50 of the related...

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Cyclohexene

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precursor to caprolactam. The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant in the presence of a tungsten...

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Aldaric acid

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at every carbon. Adipic acid, HO2C(CH2)4COOH, is not an aldaric acid, but a simple dicarboxylic acid. "Aldaric acids". Aldaric acid. IUPAC Gold Book....

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Glutaric acid

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Glutaric acid is the organic compound with the formula C3H6(COOH)2. Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble...

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Soured milk

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acetic acid (commonly found in vinegar), adipic acid, citric acid (commonly found in lemon juice), fumaric acid, glucono-delta-lactone, hydrochloric acid, lactic...

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Dibasic ester

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esters are commercially produced from short-chain acids such as adipic acid, glutaric acid, and succinic acid. They are non-flammable, readily biodegradable...

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Chytridiomycota

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as an energy storage compound, and synthesis of lysine by the α-amino adipic acid (AAA) pathway. Chytrids are saprobic, degrading refractory materials...

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Nylon

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and adipic acid; PA 66/610: [NH−(CH2)6−NH−CO−(CH2)4−CO]n−[NH−(CH2)6−NH−CO−(CH2)8−CO]m made from hexamethylenediamine, adipic acid and sebacic acid. The...

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Dimethyl adipate

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pigment dispersant. Dimethyl adipate is prepared by esterification of adipic acid with methanol. Less conventional routes include the hydroesterification...

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Surfactant

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used as a surfactant-like heterogeneous catalyst for the synthesis of adipic acid. Agents that increase surface tension are "surface active" in the literal...

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