2,2'-oxybis(N,N-bis(2-ethylhexyl)acetamide)
[CAS# 669087-46-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: 2,2'-oxybis(N,N-bis(2-ethylhexyl)acetamide)
• Synonyms: 2-[2-[bis(2-ethylhexyl)amino]-2-oxoethoxy]-N,N-bis(2-ethylhexyl)acetamide
• Molecular Formula: C₃₆H₇₂N₂O₃
• Molecular Weight: 580.97
• CAS Registry Number: 669087-46-1
• SMILES: CCCCC(CC)CN(CC(CC)CCCC)C(=O)COCC(=O)N(CC(CC)CCCC)CC(CC)CCCC

Properties

• Density: 0.9 g/cm³ Calc.^*
• Boiling point: 640.6 ºC 760 mmHg (Calc.)^*
• Flash point: 341.2 ºC (Calc.)^*
• Index of refraction: 1.468 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

2,2'-Oxybis(N,N-bis(2-ethylhexyl)acetamide) is a symmetrical, lipophilic diamide featuring an ether linkage connecting two N,N-bis(2-ethylhexyl)acetamide units. The molecule combines two amide functional groups with long branched alkyl chains, imparting both solubility in nonpolar solvents and steric bulk. This structural motif is commonly utilized in coordination chemistry, solvent extraction processes, and as a building block in the design of amphiphilic and chelating agents.

The synthesis of 2,2'-oxybis(N,N-bis(2-ethylhexyl)acetamide) typically involves the coupling of N,N-bis(2-ethylhexyl)acetamide precursors with a suitable dihalide or activated ether intermediate. Reaction conditions are optimized to favor the formation of the ether-linked diamide without over-alkylation or side reactions. Purification is generally performed through recrystallization or chromatographic techniques to yield a viscous oil or solid, depending on the chain conformation and purity.

In coordination chemistry and solvent extraction, this compound functions as a chelating ligand capable of interacting with metal ions through the carbonyl oxygen atoms of the amide groups. The branched 2-ethylhexyl chains enhance solubility in organic solvents and help stabilize metal-ligand complexes, making it valuable for applications in nuclear fuel reprocessing, heavy metal extraction, and environmental remediation. Its lipophilic character also facilitates selective partitioning of metal ions from aqueous to organic phases.

In synthetic organic chemistry, 2,2'-oxybis(N,N-bis(2-ethylhexyl)acetamide) serves as an intermediate for designing multifunctional ligands, surfactants, and amphiphilic molecules. The ether linkage provides structural flexibility, while the bulky amide substituents allow for steric control in reactions and influence molecular self-assembly. This makes it useful in creating supramolecular structures, micelles, and organized materials for chemical or materials research.

Physically, the compound is typically obtained as a viscous oil or waxy solid with solubility in nonpolar or moderately polar organic solvents such as toluene, chloroform, and hexane. It is stable under ambient conditions but should be stored away from strong oxidizing agents and moisture, which could hydrolyze the amide or ether linkages. Proper handling ensures its chemical integrity for use in synthesis, extraction, or materials applications.

Overall, 2,2'-oxybis(N,N-bis(2-ethylhexyl)acetamide) is a symmetrical, lipophilic diamide connected by an ether linkage. Its combination of bulky amide groups, long branched alkyl chains, and a flexible ether backbone enables selective metal coordination, solubility modulation, and incorporation into multifunctional molecular designs, making it valuable in synthetic chemistry, solvent extraction, and materials science.

References

2024. Development of a process for the separation of MA(III) from Ln(III) fission products using HONTA impregnated adsorbent. Journal of Radioanalytical and Nuclear Chemistry, 333(7).
DOI: 10.1007/s10967-024-09471-0

2023. Novel simplified synthesis of diglycolamides extractants. Journal of Radioanalytical and Nuclear Chemistry, 328(12).
DOI: 10.1007/s10967-023-09258-9

2020. Asymmetric diglycolamide in BmimNTf2 as an effective solvent system for the uranyl extraction. Journal of Radioanalytical and Nuclear Chemistry, 325(3).
DOI: 10.1007/s10967-020-07330-2