4,4'-Oxydianiline

4,4′-Oxydianiline (ODA) is an organic compound with the formula O(C6H4NH2)2. It is an ether derivative of aniline. This colourless solid is a useful monomer and cross-linking agent for polymers, especially the polyimides, such as Kapton.

4,4′-Oxydianiline
Names
Preferred IUPAC name
4,4′-Oxydianiline
Other names
4,4′-Diaminodiphenyl ether; 4-Aminophenyl ether; 4,4′-Oxybisbenzenamine; Bis(4-aminophenyl) ether; 4,4′-ODA
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.707
EC Number
  • 202-977-0
KEGG
UNII
UN number 3077
  • InChI=1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2 checkY
    Key: HLBLWEWZXPIGSM-UHFFFAOYSA-N checkY
  • InChI=1/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2
    Key: HLBLWEWZXPIGSM-UHFFFAOYAM
  • O(c1ccc(N)cc1)c2ccc(cc2)N
Properties
C12H12N2O
Molar mass 200.24 g/mol
Appearance Colorless crystalline solid
Melting point 188 to 192 °C (370 to 378 °F; 461 to 465 K)
Boiling point 219 °C (426 °F; 492 K)
Insoluble
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H311, H331, H340, H350, H361f, H411
P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
Flash point 219 °C (426 °F; 492 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Uses

4,4′-Oxydianiline is used in the production of a wide variety of polymer resins. The primary use lies in the production of polyimide and poly(ester)imide resins. These resins are used for their temperature-resistant properties and are utilized in products including wire enamels, coatings, film, adhesives, insulating varnishes, coated fabrics, flame-retardant fibers, oil sealants and retainers, insulation for cables and printed circuits, and laminates and composite for aerospace vehicles.

Other applications of 4,4′-oxydianiline include the production of poly(amide)imide resins (which are used in the manufacture of heat-resistant wire enamels and coatings), as an intermediate in the manufacture of epoxy resins and adhesives, and in the production of aromatic polyether imides.[1] Its use in the production of polyimine vitrimers has also been proposed.[2]

A specific reaction involving industrial use of 4,4′-oxydianiline is in the production of thermostable poly(amideurea) acids, which can be prepared from 4,4′-oxydianiline, pyromellitic dianhydride, and diisocyanates. These poly(amideurea) acids can be used as intermediates in the syntheses of poly(imideurea)s:[3]

References
  1. "11th ROC: 4,4'-Oxydianiline" (PDF). Archived (PDF) from the original on 2009-01-31. Retrieved 2008-02-28.
  2. Schoustra, Sybren K.; Dijksman, Joshua A.; Zuilhof, Han; Smulders, Maarten M. J. (2021). "Molecular control over vitrimer-like mechanics – tuneable dynamic motifs based on the Hammett equation in polyimine materials". Chemical Science. 12 (1): 293–302. doi:10.1039/d0sc05458e. ISSN 2041-6520. PMC 8178953. PMID 34163597.
  3. Chiria, C.I; Tanasã, F. (2000). "Polyureas". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. doi:10.1002/14356007.d21_d01. ISBN 3527306730.
  • MSDS Material Safety Data Sheet provided by Sigma-Aldrich.
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