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Dicarboxylic acid

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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.[1] In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.[1] 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.[2]

Partial list of saturated dicarboxylic acids

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Some common or illustrative examples

C nCommon nameSystematic IUPAC nameStructurepKa1pKa2PubChem
C2 0Oxalic acidethanedioic acidImage1.274.27971
C3 1Malonic acidpropanedioic acidImage2.855.05867
C4 2Succinic acidbutanedioic acidImage4.215.411110
C5 3Glutaric acidpentanedioic acidImage4.345.41743
C6 4Adipic acidhexanedioic acidImage4.415.41196
C7 5Pimelic acidheptanedioic acidImage4.505.43385
C8 6Suberic acidoctanedioic acidImage4.5265.49810457
C8 61,4-Cyclohexanedicarboxylic acidImage14106
C9 7Azelaic acidnonanedioic acidImage4.5505.4982266
C10 8Sebacic aciddecanedioic acidImage4.7205.4505192
C11 9undecanedioic acidImage15816
C12 10dodecanedioic acidImage 12736
C13 11Brassylic acidtridecanedioic acidImage10458
C14 12Tetradecanedioic acidTetradecanedioic acid]
C16 14Thapsic acidhexadecanedioic acidImage10459
C21 19Japanic acidheneicosanedioic acidImage9543668
C22 20Phellogenic aciddocosanedioic acidImage244872
C30 28Equisetolic acidtriacontanedioic acidImage5322010

Unsaturated dicarboxylic acids

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TypeCommon nameIUPAC nameIsomerStructural formulaPubChem
MonounsaturatedMaleic acid(Z)-Butenedioic acidcisImage444266
Fumaric acid(E)-Butenedioic acidtransImage444972
Glutaconic acid(Z)-Pent-2-enedioic acidcisImage5370328
(E)-Pent-2-enedioic acidtransImage5280498
2-Decenedioic acidtransImage6442613
Traumatic acidDodec-2-enedioic acidtransImage5283028
DiunsaturatedMuconic acid(2E,4E)-Hexa-2,4-dienedioic acidtrans,transImage5356793
(2Z,4E)-Hexa-2,4-dienedioic acidcis,transImage280518
(2Z,4Z)-Hexa-2,4-dienedioic acidcis,cisImage5280518
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–Image811
AcetylenicAcetylenedicarboxylic acidBut-2-ynedioic acidnot applicableImage371

Substituted dicarboxylic acids

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Common nameIUPAC nameStructural formulaPubChem
Tartronic acid2-Hydroxypropanedioic acidImage45
Mesoxalic acidOxopropanedioic acidImage10132
Malic acidHydroxybutanedioic acidImage525
Tartaric acid2,3-Dihydroxybutanedioic acidImage875
Oxaloacetic acidOxobutanedioic acidImage970
Aspartic acid2-Aminobutanedioic acidImage5960
dioxosuccinic aciddioxobutanedioic acidImage82062
α-hydroxyGlutaric acid2-hydroxypentanedioic acidImage43
Arabinaric acid2,3,4-Trihydroxypentanedioic acid109475
Acetonedicarboxylic acid3-Oxopentanedioic acidImage68328
α-Ketoglutaric acid2-Oxopentanedioic acidImage51
Glutamic acid2-Aminopentanedioic acidImage611
Diaminopimelic acid(2R,6S)-2,6-Diaminoheptanedioic acidImage865
Saccharic acid(2S,3S,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acidImage33037

Aromatic dicarboxylic acids

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Common namesIUPAC nameStructurePubChem
Phthalic acid
o-phthalic acid		Benzene-1,2-dicarboxylic acidImage1017
Isophthalic acid
m-phthalic acid		Benzene-1,3-dicarboxylic acidImage8496
Terephthalic acid
p-phthalic acid		Benzene-1,4-dicarboxylic acidImage7489
Diphenic acid
Biphenyl-2,2′-dicarboxylic acid		2-(2-Carboxyphenyl)benzoic acidImage10210
2,6-Naphthalenedicarboxylic acid2,6-Naphthalenedicarboxylic acidImage14357

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

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References

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  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.
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