3,4'-Oxydianiline

Description

3,4'-Oxydianiline (3,4'-ODA) is a phenyl ether derivative capped at both ends with two amines in the para and meta positions. 3,4'-ODA is commonly used in the synthesis of polyimides which have multifunctional properties.3,4'-ODA is transparent and can be used as a substrate for displays. Polyimides are transparent and can be used as substrates for displays. 3,4'-ODA can also be used to synthesise organic porous materials with a BET surface area of up to 351 m2/g. Polyetherimide membranes made from this diamine structural unit show good permeation during water-isopropanol separation.

Uses

3,4''-Diaminodiphenyl Ether, can be used for the synthesis of asymmetric soluble polyimides. It can also be used as a spacer in the preparation of glycine-based molecular tongs as inhibitors of β-amyloid peptide Aβ1-40 aggregation in vitro.

Uses

3,4'-Oxydianiline is an ether organic substance and can be used as a pharmaceutical intermediate.

Application

3,4'-Oxydianiline (3,4'-ODA) is a diphenylamine compound with a purity of up to 99%. It is commonly used as a synthetic raw material, reacting with acid anhydrides to form polyimide films or foams. It is also used in the production of co-p-aramid fibres. Co-p-aramid fibres synthesised using 3,4'-ODA as the sole comonomer exhibit tensile moduli and tensile strengths of 80.4 and 3.1 GPa, respectively. These aramid fibres are widely used in bulletproof vests, optical cables and the aerospace industry.

Materials Uses

The addition of 3,4'-Oxydianiline(3,4′-ODA) significantly alters the microcellular morphology and macroscopic volume stability of polyimide by introducing flexible segments and changing the gas release kinetics during the foaming process.^[2]

Synthesis

GENERAL STEPS: The hydrogenation reaction was carried out in a 100 mL reaction flask equipped with an FB generator without additional stirring. 3-Amino-4'-nitrodiphenyl ether (10 mmol) was dissolved in ethyl acetate (80 mL) and subsequently heated to 30 °C. H2-FB was introduced into the reaction system in the presence of palladium alumina spheres (0.5% Pd, 2-4 mm, 0.3 mmol, 3 mol%) using a FB generator (MA3-FS) at a flow rate of 5 mL/min. The reaction progress was monitored by sampling the reaction periodically by GC analysis. Upon completion of the hydrogenation reaction, ethyl acetate was removed by vacuum evaporation to obtain high purity 3,4'-diaminodiphenyl ether.

References

[1] Synlett,  2017,  vol. 28,  # 16,  p. 2184 - 2188
[2] YIN LI. Effects of 3,4′-oxydianiline on the structures and properties of a novel aromatic polyimide foam[J]. Journal of Applied Polymer Science, 2012, 125 5: 4128-4134. DOI:10.1002/app.35683.