Oleylamine Explained

Oleylamine is an organic compound with a molecular formula C18H35NH2.[1] It is an unsaturated fatty amine related to the fatty acid oleic acid. The pure compound is a clear and colorless liquid. Commercially available oleylamine reagents[2] [3] [4] [5] [6] vary in colour from clear and colorless to varying degrees of yellow due to impurities. The major impurities include trans isomer (elaidylamine) and other long chain amines with varying chain lengths.[7] Minor impurities include oxygen-containing substances such as amides and nitroalkanes.

Chemical reactions

Oleylamine reacts with carboxylic acid to form its carboxylate salt through an exothermic reaction.[8] [9] Its carboxylate salt can further condensate into amides through the loss of one water molecule. In the presence of acetic acid, oleylamin formes with DNA insoluble complexes with the radii of the particles equal 60–65 nm.[10]

Uses

Commercially, it is mainly used as a surfactant or precursor to surfactants.[11]

It has also been used in the laboratory to synthesise nanoparticles.[12] [13] 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.

Safety

Oleylamine has an LD50 (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.[14]

See also

Notes and References

  1. Web site: Oleylamine. Pubchem. pubchem.ncbi.nlm.nih.gov. en. 2019-03-10.
  2. Web site: Oleylamine, technical grade 70% (Sigma-Aldrich). March 10, 2019.
  3. Web site: Oleylamine, ≥98% primary amine (Sigma-Aldrich).
  4. Web site: Oleylamine, min. 95% (Strem Chemicals). March 10, 2019.
  5. Web site: Oleylamine, min. 70% (Strem Chemicals). March 10, 2019.
  6. Web site: Oleylamine, approximate C18-content 80-90% (Acros Organics, catalog number 12954). March 10, 2019.
  7. Baranov. Dmitry. Lynch. Michael J.. Curtis. Anna C.. Carollo. Alexa R.. Douglass. Callum R.. Mateo-Tejada. Alina M.. Jonas. David M.. 2019-02-26. Purification of Oleylamine for Materials Synthesis and Spectroscopic Diagnostics for trans Isomers. Chemistry of Materials. en. 31. 4. 1223–1230. 10.1021/acs.chemmater.8b04198. 0897-4756. free.
  8. Yin. Xi. Wu. Jianbo. Li. Panpan. Shi. Miao. Yang. Hong. Self-Heating Approach to the Fast Production of Uniform Metal Nanostructures. ChemNanoMat. January 2016. 2. 1. 37–41. 10.1002/cnma.201500123.
  9. Almeida. Guilherme. Goldoni. Luca. Akkerman. Quinten. Dang. Zhiya. Khan. Ali Hossain. Marras. Sergio. Moreels. Iwan. Manna. Liberato. 2018-02-27. Role of Acid–Base Equilibria in the Size, Shape, and Phase Control of Cesium Lead Bromide Nanocrystals. ACS Nano. en. 12. 2. 1704–1711. 10.1021/acsnano.7b08357. 1936-0851. 5830690. 29381326.
  10. Zaborova . O. V. . Voinova . A. D. . Shmykov . B. D. . Sergeyev . V. G. . Solid Lipid Nanoparticles for the Nucleic Acid Encapsulation . Reviews and Advances in Chemistry . 2021 . en . 11 . 3–4 . 178–188 . 10.1134/S2079978021030055 . 246946068 . 2634-8276.
  11. Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  12. Mourdikoudis. Stefanos. Liz-Marzán. Luis M.. 2013-05-14. Oleylamine in Nanoparticle Synthesis. Chemistry of Materials. 25. 9. 1465–1476. 10.1021/cm4000476. 0897-4756.
  13. Yin. Xi. Shi. Miao. Wu. Jianbo. Pan. Yung-Tin. Gray. Danielle L.. Bertke. Jeffery A.. Yang. Hong. Quantitative Analysis of Different Formation Modes of Pt Nanocrystals Controlled by Ligand Chemistry. Nano Letters. 17. 10. 6146–6150. 5 September 2017. 10.1021/acs.nanolett.7b02751. 28873317. free.
  14. Web site: Oleylamine(112-90-3) 1H NMR.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Oleylamine".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.