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]

Contents

Partial list of saturated dicarboxylic acids

Some common or illustrative examples

CnCommon nameSystematic IUPAC nameStructurepKa1pKa2PubChem
C20 Oxalic acid ethanedioic acid Oxalsaure2.svg 1.274.27 971
C31 Malonic acid propanedioic acid Malonsaure.svg 2.855.05 867
C42 Succinic acid butanedioic acid Kwas bursztynowy007.svg 4.215.41 1110
C53 Glutaric acid pentanedioic acid Glutaric acid.png 4.345.41 743
C64 Adipic acid hexanedioic acid Adipic acid structure.png 4.415.41 196
C75 Pimelic acid heptanedioic acid Heptanedioic acid 200.svg 4.505.43 385
C86 Suberic acid octanedioic acid Suberic acid.svg 4.5265.498 10457
C86 1,4-Cyclohexanedicarboxylic acid 1,4-cyclohexanedicarboxylicAcid.svg 14106
C97 Azelaic acid nonanedioic acid Azelaic acid.svg 4.5505.498 2266
C108 Sebacic acid decanedioic acid Sebacic acid.png 4.7205.450 5192
C119undecanedioic acid Undecanedioic acid.svg 15816
C1210 dodecanedioic acid Dodecanedioic acid structure.svg 12736
C1311 Brassylic acid tridecanedioic acid Brassylic acid.svg 10458
C1614 Thapsic acid hexadecanedioic acid Thapsic acid.png 10459
C2119 Japanic acid heneicosanedioic acid 9543668
C2220Phellogenic acid docosanedioic acid Docosanedioic acid.svg 244872
C3028 Equisetolic acid triacontanedioic acid Equisetolic acid v2.svg 5322010

Unsaturated dicarboxylic acids

TypeCommon nameIUPAC nameIsomerStructural formulaPubChem
Monounsaturated Maleic acid (Z)-Butenedioic acidcis Maleic-acid-2D-skeletal-A.svg 444266
Fumaric acid (E)-Butenedioic acidtrans Fumarsaure.svg 444972
Glutaconic acid (Z)-Pent-2-enedioic acidcis Glutaconic acid cis vinyl-H.png 5370328
(E)-Pent-2-enedioic acidtrans Glutaconic acid trans vinyl-H.png 5280498
2-Decenedioic acid trans 2-Decenedioic acid.svg 6442613
Traumatic acid Dodec-2-enedioic acidtrans Traumatic acid structure.png 5283028
Diunsaturated Muconic acid (2E,4E)-Hexa-2,4-dienedioic acidtrans,trans Muconic acid EE.svg 5356793
(2Z,4E)-Hexa-2,4-dienedioic acidcis,trans Muconic acid EZ.svg 280518
(2Z,4Z)-Hexa-2,4-dienedioic acidcis,cis Muconic acid ZZ.svg 5280518
Glutinic acid
(Allene-1,3-dicarboxylic acid)		(RS)-Penta-2,3-dienedioic acid HO2CCH=C=CHCO2H 5242834
Branched Citraconic acid (2Z)-2-Methylbut-2-enedioic acidcis Citraconic acid.svg 643798
Mesaconic acid (2E)-2-Methyl-2-butenedioic acidtrans Mesaconic-acid-2D-skeletal.svg 638129
Itaconic acid 2-Methylidenebutanedioic acid– Itaconic acid.svg 811
Acetylenic Acetylenedicarboxylic acid But-2-ynedioic acidnot applicable Acetylenedicarboxylic acid.svg 371

Substituted dicarboxylic acids

Common nameIUPAC nameStructural formulaPubChem
Tartronic acid 2-Hydroxypropanedioic acid Tartronic acid.svg 45
Mesoxalic acid Oxopropanedioic acid Mesoxalic acid.png 10132
Malic acid Hydroxybutanedioic acid Apfelsaure3.svg 525
Tartaric acid 2,3-Dihydroxybutanedioic acid Tartaric acid.svg 875
Oxaloacetic acid Oxobutanedioic acid Oxaloacetic acid.svg 970
Aspartic acid 2-Aminobutanedioic acid Asparaginsaure - Aspartic acid.svg 5960
dioxosuccinic acid dioxobutanedioic acid Dioxosuccinic acid.svg 82062
α-hydroxyGlutaric acid 2-hydroxypentanedioic acid Alpha-hydroxyglutaric acid.png 43
Arabinaric acid 2,3,4-Trihydroxypentanedioic acid 109475
Acetonedicarboxylic acid 3-Oxopentanedioic acid Structural formula of acetonedicarboxylic acid.svg 68328
α-Ketoglutaric acid 2-Oxopentanedioic acid Alpha-ketoglutaric acid.png 51
Glutamic acid 2-Aminopentanedioic acid Glutaminsaure - Glutamic acid.svg 611
Diaminopimelic acid (2R,6S)-2,6-Diaminoheptanedioic acid Diaminopimelic acid.svg 865
Saccharic acid (2S,3S,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid Glucaric acid structure.svg 33037

Aromatic dicarboxylic acids

Common namesIUPAC nameStructurePubChem
Phthalic acid
o-phthalic acid		Benzene-1,2-dicarboxylic acid Phthalic-acid-2D-skeletal.png 1017
Isophthalic acid
m-phthalic acid		Benzene-1,3-dicarboxylic acid Isophthalic-acid-2D-skeletal.png 8496
Terephthalic acid
p-phthalic acid		Benzene-1,4-dicarboxylic acid Terephthalic-acid-2D-skeletal.png 7489
Diphenic acid
Biphenyl-2,2′-dicarboxylic acid		2-(2-Carboxyphenyl)benzoic acid Diphenic Acid Structural Formula V.1.svg 10210
2,6-Naphthalenedicarboxylic acid 2,6-Naphthalenedicarboxylic acid 2,6-Naphthalenedicarboxylic acid.svg 14357

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.
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