Oleylamine

Chemical reactions

Oleylamine reacts with carboxylic acid to form its carboxylate salt through an exothermic reaction. Its carboxylate salt can further condensate into amides through the loss of one water molecule. In the presence of acetic acid, oleylamine forms with DNA insoluble complexes with the radii of the particles equal 60–65 nm.

Uses

Commercially, it is mainly used as a surfactant or precursor to surfactants.

It has also been used in the laboratory to synthesise nanoparticles. It can function both as a solvent for the reaction mixture and as a coordinating agent to stabilize the surface of the particles. It can also coordinate with metal ions, change the form of metal precursors and affect the formation kinetics of nanoparticles during the synthesis. As a ligand bound to metal nanoparticle surfaces, it exhibits an apparent length of 1.8 - 2.2 nm. This reported value varies between studies and the degree of interdigitation between overlapping oleylamine layers, particularly those of neighboring nanoparticles.

Safety

Oleylamine has an (intraperitoneal) of 888 mg/kg in mice; however, note that it is listed as a level 3 health hazard on the NFPA diamond, so it should be handled with caution.

Characterization

Oleylamine can be characterized using MS, HNMR, CNMR, IR, and Raman. Each technique shows distinct peaks in various regions.

References

References

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3. "Oleylamine, ≥98% primary amine (Sigma-Aldrich)".
4. "Oleylamine, min. 95% (Strem Chemicals)".
5. "Oleylamine, min. 70% (Strem Chemicals)".
6. "Oleylamine, approximate C18-content 80-90% (Acros Organics, catalog number 12954)".
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13. (5 September 2017). "Quantitative Analysis of Different Formation Modes of Pt Nanocrystals Controlled by Ligand Chemistry". Nano Letters.
14. (2022). "Effect of Oleylamine on the Surface Chemistry, Morphology, Electronic Structure, and Magnetic Properties of Cobalt Ferrite Nanoparticles". Nanomaterials.
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