1,3-Propylenediaminetertaacetic acid
[CAS# 1939-36-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 1,3-Propylenediaminetertaacetic acid
• Synonyms: 1,3-Propylenediamine-N,N,N',N'-tetraacetic acid
• Molecular Formula: C₁₁H₁₈N₂O₈
• Molecular Weight: 306.27
• CAS Registry Number: 1939-36-2
• EC Number: 400-400-9
• SMILES: C(CN(CC(=O)O)CC(=O)O)CN(CC(=O)O)CC(=O)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 250 ºC (dec.) (Expl.)
• Index of Refraction: 1.571, Calc.^*
• Boiling Point: 620.5±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 329.1±31.5 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Hazard Statements: H302-H318-H361
• Precautionary Statements: P203-P264-P264+P265-P270-P280-P301+P317-P305+P354+P338-P317-P318-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

1,3-Propylenediaminetetraacetic acid, often abbreviated as PDTA, is an organic compound that belongs to the class of aminopolycarboxylate ligands. It is a derivative of propylenediamine, which contains four carboxyl groups capable of binding to metal ions. This compound has garnered significant attention in the fields of chemistry and biochemistry due to its ability to form stable complexes with various metal ions, making it useful in a variety of applications ranging from analytical chemistry to medicine.

The discovery of 1,3-Propylenediaminetetraacetic acid can be traced back to research on polyaminocarboxylate ligands. The structure of PDTA includes a propylene backbone with two amino groups and four carboxylate groups, which enables it to form highly stable chelates with metal ions. This ligand was developed to improve the efficiency and stability of metal complexation compared to simpler polycarboxylate ligands. Its design was motivated by the need for more robust chelating agents that could be used in a range of processes requiring metal ion binding.

1,3-Propylenediaminetetraacetic acid is synthesized through a multi-step process that involves the reaction of propylenediamine with acetic acid derivatives to introduce the carboxyl groups. The resulting compound is a highly efficient chelating agent, capable of binding divalent and trivalent metal ions such as calcium, magnesium, copper, and iron. The chelation of metal ions is facilitated by the coordination of the amino and carboxylate groups to the metal center, forming a stable complex. This property is particularly valuable in various chemical and industrial processes that require the controlled interaction of metal ions.

One of the major applications of 1,3-Propylenediaminetetraacetic acid is in the field of metal ion sequestration. It is commonly used in analytical chemistry to remove unwanted metal ions from solutions or to stabilize metal complexes in solution. In this context, PDTA is used in techniques such as ion-exchange chromatography and complexometric titration, where it is employed to quantify or separate metal ions. The compound's ability to form stable complexes with metal ions also makes it useful in the purification of water and other industrial processes that involve metal contaminants.

In the medical field, 1,3-Propylenediaminetetraacetic acid has applications in the treatment of heavy metal poisoning. The compound's high affinity for metal ions makes it useful as a chelating agent to remove toxic metals such as lead, mercury, and arsenic from the body. It is employed in chelation therapy, a medical treatment aimed at reducing the concentration of heavy metals in the bloodstream. PDTA’s effectiveness in binding to these toxic metals allows for their excretion from the body, thus mitigating their harmful effects. The compound has been used in clinical settings to treat cases of metal toxicity, especially in patients with chronic exposure to heavy metals.

Furthermore, 1,3-Propylenediaminetetraacetic acid is used in research to study the behavior of metal ions in biological systems. Its ability to form stable complexes with metals makes it a valuable tool in biochemistry, particularly in experiments involving metal ion metabolism and enzyme activation. Researchers use PDTA to mimic the role of metal ions in biological systems or to inhibit metal-dependent processes.

In environmental chemistry, PDTA has also found applications in the removal of metal ions from wastewater. The compound’s ability to form stable metal complexes is harnessed in water treatment processes to capture and remove toxic metal pollutants from industrial effluents. By sequestering metal ions, PDTA prevents the harmful accumulation of metals in the environment, contributing to cleaner water and safer ecosystems.

Despite its versatility, there are some limitations to the use of 1,3-Propylenediaminetetraacetic acid. One challenge is the potential for environmental contamination from the disposal of large quantities of PDTA-containing waste, especially in industrial applications. Additionally, the effectiveness of PDTA in complexing metal ions can vary depending on the metal involved and the conditions under which it is used. Ongoing research aims to enhance the efficiency of PDTA and to explore safer and more sustainable alternatives for its use in metal sequestration and chelation therapy.

In conclusion, 1,3-Propylenediaminetetraacetic acid is a highly valuable compound with diverse applications across multiple fields, from environmental science to medicine. Its ability to bind metal ions effectively makes it a key player in the removal of toxic metals, as well as in a variety of industrial and research applications.