1,2,3,4-Butanetetracarboxylic acid

Chemical compound From Wikipedia, the free encyclopedia

1,2,3,4-Butanetetracarboxylic acid is an organic compound with the formula HO2CCH2CH(CO2H)CH(CO2H)CH2CO2H. It is one of the simplest stable tetracarboxylic acids. The compound exists as two diastereomers, meso and the (R,R)/(S,S) pair. All are white solids. The compound is produced by oxidation of tetrahydrophthalic anhydride.[1]

Quick facts Names, Identifiers ...
1,2,3,4-Butanetetracarboxylic acid
Names
Preferred IUPAC name
Butane-1,2,3,4-tetracarboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 216-938-0
  • InChI=1S/C8H10O8/c9-5(10)1-3(7(13)14)4(8(15)16)2-6(11)12/h3-4H,1-2H2,(H,9,10)(H,11,12)(H,13,14)(H,15,16)
    Key: GGAUUQHSCNMCAU-UHFFFAOYSA-N
  • C(C(C(CC(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
C8H10O8
Molar mass 234.160 g·mol−1
Appearance White solid
Melting point 236 Â°C (457 Â°F; 509 K)
246 ºC for meso
227-230 ºC for (R,R)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Uses and reactions

Among the several possible uses, it has been repeatedly investigated in the textile industry,[2] e.g., for permanent press clothing.[3] As expected for a polycarboxylate, it binds zinc to afford coordination polymers.[4]

It forms a dianhydride (RN 4534-73-0), which consists of two succinic anhydride-like rings.[1]

References

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