Wikipedia / Dicarboxylic acid
Wikipedia / Dicarboxylic acid
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 || || 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 |- |C14 | 12 || Tetradecanedioic acid || Tetradecanedioic acid] || || || || |- |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
{| class="wikitable skin-invert-image"
|+ |- ! Type !! Common name !! IUPAC name !! Isomer !! Structural formula !! PubChem |- | rowspan="7" | Monounsaturated || Maleic acid || (Z)-Butenedioic acid || cis || || 444266 |- | Fumaric acid || (E)-Butenedioic acid || trans || || 444972 |- | rowspan="2" | 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 |- | rowspan="4" | Diunsaturated || rowspan=3 | 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 |- | rowspan="3" | Branched || Citraconic acid || (2Z)-2-Methylbut-2-enedioic acid || cis || || 643798 |- | Mesaconic acid || (2E)-2-Methyl-2-butenedioic acid || trans || || 638129 |- | Itaconic acid || 2-Methylidenebutanedioic acid || – || || 811 |- | rowspan="7" | Acetylenic ||Acetylenedicarboxylic acid || But-2-ynedioic acid || not applicable || || 371 |- |}
Substituted dicarboxylic acids
{| class="wikitable skin-invert-image"
|+ |- ! 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
{| class="wikitable skin-invert-image"
|+ ! Common names !! IUPAC name !! Structure || PubChem |- | Phthalic acido-phthalic acid || Benzene-1,2-dicarboxylic acid || || 1017 |- | Isophthalic acidm-phthalic acid || Benzene-1,3-dicarboxylic acid || || 8496 |- | Terephthalic acidp-phthalic acid || Benzene-1,4-dicarboxylic acid || || 7489 |- | Diphenic acidBiphenyl-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.