Dicarboxylic acid

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In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (Template:Chem2). The general molecular formula for dicarboxylic acids can be written as Template:Chem2, 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 File:Oxalsäure2.svg 1.27 4.27 971
C3 1 Malonic acid propanedioic acid File:Malonic acid structure.png 2.85 5.05 867
C4 2 Succinic acid butanedioic acid File:Succinic acid.png 4.21 5.41 1110
C5 3 Glutaric acid pentanedioic acid File:Glutaric acid.png 4.34 5.41 743
C6 4 Adipic acid hexanedioic acid File:Adipic acid structure.png 4.41 5.41 196
C7 5 Pimelic acid heptanedioic acid File:Pimelic acid.png 4.50 5.43 385
C8 6 Suberic acid octanedioic acid File:Suberic acid.svg 4.526 5.498 10457
C8 6 1,4-Cyclohexanedicarboxylic acid File:1,4-cyclohexanedicarboxylicAcid.svg 14106
C9 7 Azelaic acid nonanedioic acid File:Azelaic acid.svg 4.550 5.498 2266
C10 8 Sebacic acid decanedioic acid File:Sebacic acid.png 4.720 5.450 5192
C11 9 undecanedioic acid File:Undecanedioic acid.svg 15816
C12 10 dodecanedioic acid File:Dodecanedioic acid structure.svg 12736
C13 11 Brassylic acid tridecanedioic acid File:Brassylic acid.svg 10458
C16 14 Thapsic acid hexadecanedioic acid File:Thapsic acid.png 10459
C21 19 Japanic acid heneicosanedioic acid 9543668
C22 20 Phellogenic acid docosanedioic acid File:Docosanedioic acid.svg 244872
C30 28 Equisetolic acid triacontanedioic acid File:Equisetolic acid v2.svg 5322010


Unsaturated dicarboxylic acids

Type Common name IUPAC name Isomer Structural formula PubChem
Monounsaturated Maleic acid (Z)-Butenedioic acid cis File:Maleic-acid-2D-skeletal-A.svg 444266
Fumaric acid (E)-Butenedioic acid trans File:Fumarsäure.svg 444972
Glutaconic acid (Z)-Pent-2-enedioic acid cis File:Glutaconic acid cis vinyl-H.png 5370328
(E)-Pent-2-enedioic acid trans File:Glutaconic acid trans vinyl-H.png 5280498
2-Decenedioic acid trans File:2-Decenedioic acid.svg 6442613
Traumatic acid Dodec-2-enedioic acid trans File:Traumatic acid structure.png 5283028
Diunsaturated Muconic acid (2E,4E)-Hexa-2,4-dienedioic acid trans,trans File:Muconic acid EE.png 5356793
(2Z,4E)-Hexa-2,4-dienedioic acid cis,trans File:Muconic acid EZ.png 280518
(2Z,4Z)-Hexa-2,4-dienedioic acid cis,cis File:Muconic acid ZZ.png 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 – File:Itaconic acid.svg 811
Acetylenic Acetylenedicarboxylic acid But-2-ynedioic acid not applicable File:Acetylenedicarboxylic acid.svg 371

Substituted dicarboxylic acids

Common name IUPAC name Structural formula PubChem
Tartronic acid 2-Hydroxypropanedioic acid File:Tartronic acid.svg 45
Mesoxalic acid Oxopropanedioic acid File:Mesoxalic acid.png 10132
Malic acid Hydroxybutanedioic acid File:Äpfelsäure3.svg 525
Tartaric acid 2,3-Dihydroxybutanedioic acid File:Tartaric acid.svg 875
Oxaloacetic acid Oxobutanedioic acid File:Oxaloacetic acid.svg 970
Aspartic acid 2-Aminobutanedioic acid File:Asparaginsäure - Aspartic acid.svg 5960
dioxosuccinic acid dioxobutanedioic acid File:Dioxosuccinic acid.svg 82062
α-hydroxyGlutaric acid 2-hydroxypentanedioic acid File:Alpha-hydroxyglutaric acid.png 43
Arabinaric acid 2,3,4-Trihydroxypentanedioic acid 109475
Acetonedicarboxylic acid 3-Oxopentanedioic acid File:Structural formula of acetonedicarboxylic acid.svg 68328
α-Ketoglutaric acid 2-Oxopentanedioic acid File:Alpha-ketoglutaric acid.png 51
Glutamic acid 2-Aminopentanedioic acid File:Glutaminsäure - Glutamic acid.svg 611
Diaminopimelic acid (2R,6S)-2,6-Diaminoheptanedioic acid File:Diaminopimelic acid.svg 865
Saccharic acid (2S,3S,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid File:Glucaric acid structure.svg 33037

Aromatic dicarboxylic acids

Common names IUPAC name Structure PubChem
Phthalic acid
o-phthalic acid		 Benzene-1,2-dicarboxylic acid File:Phthalic-acid-2D-skeletal.png 1017
Isophthalic acid
m-phthalic acid		 Benzene-1,3-dicarboxylic acid File:Isophthalic-acid-2D-skeletal.png 8496
Terephthalic acid
p-phthalic acid		 Benzene-1,4-dicarboxylic acid File:Terephthalic-acid-2D-skeletal.png 7489
Diphenic acid
Biphenyl-2,2′-dicarboxylic acid		 2-(2-Carboxyphenyl)benzoic acid File:Diphenic Acid Structural Formula V.1.svg 10210
2,6-Naphthalenedicarboxylic acid 2,6-Naphthalenedicarboxylic acid File: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

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  1. ↑ a b Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2014, Wiley-VCH, Weinheim. Script error: No such module "CS1 identifiers".
  2. ↑ Script error: No such module "citation/CS1".

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External links

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