1,2,3,4-Butanetetracarboxylic acid

1,2,3,4-Butanetetracarboxylic acid
Names
	Other names Butane-1,2,3,4-tetracarboxylic acid
Identifiers
CAS Number	1703-58-8 unspecified stereochemistry; 4534-68-3 meso; 4799-96-6 (R,R)-enantiomer;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1574612;
EC Number	216-938-0;
PubChem CID	15560;
	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−1
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 [77 °F], 100 kPa). Infobox references

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]

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

^ ^a ^b 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.
^ 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.
^ Welch, Clark M. (1988). "Tetracarboxylic Acids as Formaldehyde-Free Durable Press Finishing Agents". Textile Research Journal. 58 (8): 480–486. doi:10.1177/004051758805800809.
^ 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.

[Acta-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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