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Dicarboxylic acid

Organic compound with two –COOH groups

Organic compound with two –COOH groups

In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , 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

:{| class="wikitable skin-invert-image" |+ !C ! n !! Common name !! Systematic IUPAC name !! Structure !! pKa1 !! pKa2 !! PubChem |- |C2 | 0 || Oxalic acid || ethanedioic acid || [[File:Oxalsäure2.svg|60px]] || 1.27 || 4.27 || 971 |- |C3 | 1 || Malonic acid || propanedioic acid || [[File:Malonsäure.svg|80px]] || 2.85 || 5.05 || 867 |- |C4 | 2 || Succinic acid || butanedioic acid || [[File:Kwas bursztynowy007.svg|100px]] || 4.21 || 5.41 || 1110 |- |C5 | 3 || Glutaric acid || pentanedioic acid || [[File:Glutaric acid.png|120px]] || 4.34 || 5.41 || 743 |- |C6 | 4 || Adipic acid || hexanedioic acid || [[File:Adipic acid structure.png|140px]] || 4.41 || 5.41 || 196 |- |C7 | 5 || Pimelic acid || heptanedioic acid || [[File:Heptanedioic acid 200.svg|160px]] || 4.50 || 5.43 || 385 |- |C8 | 6 || Suberic acid || octanedioic acid || [[File:Suberic acid.svg|180px]] || 4.526 || 5.498 || 10457 |- |C8 | 6 || || 1,4-Cyclohexanedicarboxylic acid || [[File:1,4-cyclohexanedicarboxylicAcid.svg|180px]] || || ||14106 |- |C9 | 7 || Azelaic acid || nonanedioic acid || [[File:Azelaic acid.svg|200px]] || 4.550 || 5.498 || 2266 |- |C10 | 8 || Sebacic acid || decanedioic acid || [[File:Sebacic acid.png|220px]] || 4.720 || 5.450 || 5192 |- |C11 | 9 || || undecanedioic acid || [[File:Undecanedioic acid.svg|240px]] || || || 15816 |- |C12 | 10 || || dodecanedioic acid || [[File:Dodecanedioic acid structure.svg|260px]] | || || 12736 |- |C13 | 11 || Brassylic acid || tridecanedioic acid || [[File:Brassylic acid.svg|280px]] || || || 10458 |- |C16 | 14 || Thapsic acid || hexadecanedioic acid || [[File:Thapsiasäure.svg|300px]] || || || 10459 |- |C21 | 19 || Japanic acid || heneicosanedioic acid || [[File:Japanic acid v2.svg|200px]] || || || 9543668 |- |C22 | 20 || Phellogenic acid || docosanedioic acid || [[File:Docosanedioic acid.svg|280px]] || || || 244872 |- |C30 | 28 || Equisetolic acid || triacontanedioic acid || [[File:Equisetolic acid v2.svg|280px]] || || || 5322010 |}

Unsaturated dicarboxylic acids

:{| class="wikitable skin-invert-image"

+
! Type !! Common name !! IUPAC name !! Isomer !! Structural formula !! PubChem
-
-
Fumaric acid
-
-
(E)-Pent-2-enedioic acid
-
-
Traumatic acid
-
[[File:muconic acid EE.svg
-
(2Z,4E)-Hexa-2,4-dienedioic acid
-
(2Z,4Z)-Hexa-2,4-dienedioic acid
-
Glutinic acid
(Allene-1,3-dicarboxylic acid)
-
-
Mesaconic acid
-
Itaconic acid
-
-
}

Substituted dicarboxylic acids

:{| class="wikitable skin-invert-image"

+
! Common name !! IUPAC name !! Structural formula !! PubChem
-
Tartronic acid
-
Mesoxalic acid
-
Malic acid
-
Tartaric acid
-
Oxaloacetic acid
-
Aspartic acid
-
dioxosuccinic acid
-
α-hydroxyGlutaric acid
-
Arabinaric acid
-
Acetonedicarboxylic acid
-
α-Ketoglutaric acid
-
Glutamic acid
-
Diaminopimelic acid
-
Saccharic acid
}

Simple forms of dicarboxylic acids

Hidden: Dubious relevance and un-traceable references --

Aromatic dicarboxylic acids

:{| class="wikitable skin-invert-image" |+ ! Common names !! IUPAC name !! Structure || PubChem |- | Phthalic acid o-phthalic acid || Benzene-1,2-dicarboxylic acid || [[File:Phthalic-acid-2D-skeletal.png|80px]] || 1017 |- | Isophthalic acid m-phthalic acid || Benzene-1,3-dicarboxylic acid || [[File:Isophthalic-acid-2D-skeletal.png|120px]] || 8496 |- | Terephthalic acid p-phthalic acid || Benzene-1,4-dicarboxylic acid || [[File:Terephthalic-acid-2D-skeletal.png|120px]] || 7489 |- | Diphenic acid Biphenyl-2,2′-dicarboxylic acid || 2-(2-Carboxyphenyl)benzoic acid || [[File:Diphenic Acid Structural Formula V.1.svg|110px]] || 10210 |- | 2,6-Naphthalenedicarboxylic acid || 2,6-Naphthalenedicarboxylic acid || [[File:2,6-Naphthalenedicarboxylic acid.svg|150px]] || 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.

References

References

  1. 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. (1922). "Organic Chemistry". Blackie & Son.
  3. (August 1995). "0.68 Evaluation of diet-induced thermogenesisin Crohn's diseased patients". Clinical Nutrition.
  4. (November 1999). "A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples". Clinica Chimica Acta.
  5. (July 1995). "Inhibition of Atherosclerosis and Myocardial Lesions in the JCR:LA-cp Rat by β,β′-Tetramethylhexadecanedioic Acid (MEDICA 16)". Arteriosclerosis, Thrombosis, and Vascular Biology.
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