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1,2,3,4-Butanetetracarboxylic acid

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1,2,3,4-Butanetetracarboxylic acid
Names
Other names Butane-1,2,3,4-tetracarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 216-938-0
PubChem CID
InChI
  • 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
SMILES
  • C(C(C(CC(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
Chemical formula C8H10O8
Molar mass 234.160 g·mol
Appearance White solid
Melting point 236 °C (457 °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 °C , 100 kPa). Infobox references
Chemical compound

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.

Uses and reactions

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

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

References

  1. ^ Nagao, R.; Marumo, F.; Saito, Y.; Asahara, T. (1971). "The Crystal Structure of Butane-1,2,3,4-tetracarboxylic Dianhydride". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 27 (3): 569–572. Bibcode:1971AcCrB..27..569N. doi:10.1107/s0567740871002577.
  2. Eltahlawy, K.; Elbendary, M.; Elhendawy, A.; Hudson, S. (2005). "The Antimicrobial Activity of Cotton Fabrics Treated with Different Crosslinking Agents and Chitosan". Carbohydrate Polymers. 60 (4): 421–430. doi:10.1016/j.carbpol.2005.02.019.
  3. Welch, Clark M. (1988). "Tetracarboxylic Acids as Formaldehyde-Free Durable Press Finishing Agents". Textile Research Journal. 58 (8): 480–486. doi:10.1177/004051758805800809.
  4. Wei, Guo-Hua; Yang, Jin; Ma, Jian-Fang; Liu, Ying-Ying; Li, Shun-Li; Zhang, Lai-Ping (2008). "Syntheses, Structures and Luminescent Properties of Zinc(II) and Cadmium(II) Coordination Complexes Based on New Bis(imidazolyl)ether and Different Carboxylate Ligands". Dalton Transactions (23): 3080–3092. doi:10.1039/b716657e. PMID 18521450.
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