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.[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

Some common or illustrative examples

C n Common name Systematic IUPAC name Structure pKa1 pKa2 PubChem
C2 0 Oxalic acid ethanedioic acid 1.27 4.27 971
C3 1 Malonic acid propanedioic acid 2.85 5.05 867
C4 2 Succinic acid butanedioic acid 4.21 5.41 1110
C5 3 Glutaric acid pentanedioic acid 4.34 5.41 743
C6 4 Adipic acid hexanedioic acid 4.41 5.41 196
C7 5 Pimelic acid heptanedioic acid 4.50 5.43 385
C8 6 Suberic acid octanedioic acid 4.526 5.498 10457
C8 6 1,4-Cyclohexanedicarboxylic acid 14106
C9 7 Azelaic acid nonanedioic acid 4.550 5.498 2266
C10 8 Sebacic acid decanedioic acid 4.720 5.450 5192
C11 9 undecanedioic acid 15816
C12 10 dodecanedioic acid 12736
C13 11 Brassylic acid tridecanedioic acid 10458
C16 14 Thapsic acid hexadecanedioic acid 10459
C21 19 Japanic acid heneicosanedioic acid 9543668
C22 20 Phellogenic acid docosanedioic acid 244872
C30 28 Equisetolic acid triacontanedioic acid 5322010


Unsaturated dicarboxylic acids

Type Common name IUPAC name Isomer Structural formula PubChem
Monounsaturated Maleic acid (Z)-Butenedioic acid cis 444266
Fumaric acid (E)-Butenedioic acid trans 444972
Glutaconic acid (Z)-Pent-2-enedioic acid cis 5370328
(E)-Pent-2-enedioic acid trans 5280498
2-Decenedioic acid trans 6442613
Traumatic acid Dodec-2-enedioic acid trans 5283028
Diunsaturated Muconic acid (2E,4E)-Hexa-2,4-dienedioic acid trans,trans 5356793
(2Z,4E)-Hexa-2,4-dienedioic acid cis,trans 280518
(2Z,4Z)-Hexa-2,4-dienedioic acid cis,cis 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 acid cis HO2CCH=C(CH3)CO2H 643798
Mesaconic acid (2E)-2-Methyl-2-butenedioic acid trans HO2CCH=C(CH3)CO2H 638129
Itaconic acid 2-Methylidenebutanedioic acid – 811
Acetylenic Acetylenedicarboxylic acid But-2-ynedioic acid not applicable 371

Substituted dicarboxylic acids

Common name IUPAC name Structural formula PubChem
Tartronic acid 2-Hydroxypropanedioic acid 45
Mesoxalic acid Oxopropanedioic acid 10132
Malic acid Hydroxybutanedioic acid 525
Tartaric acid 2,3-Dihydroxybutanedioic acid 875
Oxaloacetic acid Oxobutanedioic acid 970
Aspartic acid 2-Aminobutanedioic acid 5960
dioxosuccinic acid dioxobutanedioic acid 82062
α-hydroxyGlutaric acid 2-hydroxypentanedioic acid 43
Arabinaric acid 2,3,4-Trihydroxypentanedioic acid 109475
Acetonedicarboxylic acid 3-Oxopentanedioic acid 68328
α-Ketoglutaric acid 2-Oxopentanedioic acid 51
Glutamic acid 2-Aminopentanedioic acid 611
Diaminopimelic acid (2R,6S)-2,6-Diaminoheptanedioic acid 865
Saccharic acid (2S,3S,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid 33037

Aromatic dicarboxylic acids

Common names IUPAC name Structure PubChem
Phthalic acid
o-phthalic acid		 Benzene-1,2-dicarboxylic acid 1017
Isophthalic acid
m-phthalic acid		 Benzene-1,3-dicarboxylic acid 8496
Terephthalic acid
p-phthalic acid		 Benzene-1,4-dicarboxylic acid 7489
Diphenic acid
Biphenyl-2,2′-dicarboxylic acid		 2-(2-Carboxyphenyl)benzoic acid 10210
2,6-Naphthalenedicarboxylic acid 2,6-Naphthalenedicarboxylic acid 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. ^ a b 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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