Dicarboxylic acid

In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (−COOH). The general molecular formula for dicarboxylic acids can be written as HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids. Dicarboxylic acids are usually colorless solids. A wide variety of dicarboxylic acids are used in industry. Adipic acid, for example, is a precursor to certain kinds of nylon. A wide variety of dicarboxylic acids are found in nature. Aspartic acid and glutamic acid are two amino acids found in all life. Succinic and fumaric acids are essential for metabolism. A large inventory of derivatives are known including many mono- and diesters, amides, etc.

Partial list of saturated dicarboxylic acids

Some common or illustrative examples

C nCommon nameSystematic IUPAC nameStructurepKa1pKa2PubChem
C2 0Oxalic acidethanedioic acid1.274.27971
C3 1Malonic acidpropanedioic acid2.855.05867
C4 2Succinic acidbutanedioic acid4.215.411110
C5 3Glutaric acidpentanedioic acid4.345.41743
C6 4Adipic acidhexanedioic acid4.415.41196
C7 5Pimelic acidheptanedioic acid4.505.43385
C8 6Suberic acidoctanedioic acid4.5265.49810457
C8 61,4-Cyclohexanedicarboxylic acid14106
C9 7Azelaic acidnonanedioic acid4.5505.4982266
C10 8Sebacic aciddecanedioic acid4.7205.4505192
C11 9undecanedioic acid15816
C12 10dodecanedioic acid 12736
C13 11Brassylic acidtridecanedioic acid10458
C14 12Tetradecanedioic acidTetradecanedioic acid]
C16 14Thapsic acidhexadecanedioic acid10459
C21 19Japanic acidheneicosanedioic acid9543668
C22 20Phellogenic aciddocosanedioic acid244872
C30 28Equisetolic acidtriacontanedioic acid5322010

Unsaturated dicarboxylic acids

TypeCommon nameIUPAC nameIsomerStructural formulaPubChem
MonounsaturatedMaleic acid(Z)-Butenedioic acidcis444266
Fumaric acid(E)-Butenedioic acidtrans444972
Glutaconic acid(Z)-Pent-2-enedioic acidcis5370328
(E)-Pent-2-enedioic acidtrans5280498
2-Decenedioic acidtrans6442613
Traumatic acidDodec-2-enedioic acidtrans5283028
DiunsaturatedMuconic acid(2E,4E)-Hexa-2,4-dienedioic acidtrans,trans5356793
(2Z,4E)-Hexa-2,4-dienedioic acidcis,trans280518
(2Z,4Z)-Hexa-2,4-dienedioic acidcis,cis5280518
Glutinic acid
(Allene-1,3-dicarboxylic acid)		(RS)-Penta-2,3-dienedioic acidHO2CCH=C=CHCO2H5242834
BranchedCitraconic acid(2Z)-2-Methylbut-2-enedioic acidcisHO2CCH=C(CH3)CO2H643798
Mesaconic acid(2E)-2-Methyl-2-butenedioic acidtransHO2CCH=C(CH3)CO2H638129
Itaconic acid2-Methylidenebutanedioic acid–811
AcetylenicAcetylenedicarboxylic acidBut-2-ynedioic acidnot applicable371

Substituted dicarboxylic acids

Common nameIUPAC nameStructural formulaPubChem
Tartronic acid2-Hydroxypropanedioic acid45
Mesoxalic acidOxopropanedioic acid10132
Malic acidHydroxybutanedioic acid525
Tartaric acid2,3-Dihydroxybutanedioic acid875
Oxaloacetic acidOxobutanedioic acid970
Aspartic acid2-Aminobutanedioic acid5960
dioxosuccinic aciddioxobutanedioic acid82062
α-hydroxyGlutaric acid2-hydroxypentanedioic acid43
Arabinaric acid2,3,4-Trihydroxypentanedioic acid109475
Acetonedicarboxylic acid3-Oxopentanedioic acid68328
α-Ketoglutaric acid2-Oxopentanedioic acid51
Glutamic acid2-Aminopentanedioic acid611
Diaminopimelic acid(2R,6S)-2,6-Diaminoheptanedioic acid865
Saccharic acid(2S,3S,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid33037

Aromatic dicarboxylic acids

Common namesIUPAC nameStructurePubChem
Phthalic acid
o-phthalic acid		Benzene-1,2-dicarboxylic acid1017
Isophthalic acid
m-phthalic acid		Benzene-1,3-dicarboxylic acid8496
Terephthalic acid
p-phthalic acid		Benzene-1,4-dicarboxylic acid7489
Diphenic acid
Biphenyl-2,2′-dicarboxylic acid		2-(2-Carboxyphenyl)benzoic acid10210
2,6-Naphthalenedicarboxylic acid2,6-Naphthalenedicarboxylic acid14357

Terephthalic acid is a commodity chemical used in the manufacture of the polyester known by brand names such as PET, Terylene, Dacron and Lavsan.

See also

References

  1. 1 2 Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2014, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_523.pub3
  2. ↑ Bernthsen, A. (1922). Organic Chemistry. London: Blackie & Son. p. 242.