EDDHA or ethylenediamine-''N'',''N′''-bis(2-hydroxyphenylacetic acid) is a

chelating agent Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...

. Like EDTA, it binds metal ions as a hexadentate ligand, using two amines, two phenolate centers, and two carboxylates as the six binding sites. The complexes are typically anionic. The ligand itself is a white, water soluble powder. Both the free ligand and its tetraanionic chelating agent are abbreviated EDDHA. In contrast to EDDHA, most related aminopolycarboxylic acid chelating agents feature tertiary amines and few have phenolate groups. : EFOREWdownC2

Preparation

It is produced by the multicomponent reaction of

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

, glyoxalic acid, and

ethylenediamine Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately ...

. In this process, the initial Schiff base condensate alkylates the phenol. Related ligands can be prepared more efficiently using ''para''-cresol.

Uses

It is used to mobilize metal ions analogously to the use of EDTA. EDDHA has been used in

phytoextraction Phytoextraction is a subprocess of phytoremediation in which plants remove dangerous elements or compounds from soil or water, most usually heavy metals, metals that have a high density and may be toxic to organisms even at relatively low concentra ...

of lead from contaminated soils. It degrades with release of

salicylic acid Salicylic acid is an organic compound with the formula HOC6H4CO2H. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the EPA Toxic Substance ...

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References

Chelating agents Dicarboxylic acids Phenols