Oleylamine

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 color 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.[7]

Oleylamine
Names
IUPAC name
(Z)-Octadec-9-enylamine
Other names
9-Octadecenylamine
1-Amino-9-octadecene, (9Z)-Octadecene
Identifiers
ChemSpider
ECHA InfoCard 100.003.650
UNII
Properties
C18H37N
Molar mass 267.493 g/mol
Appearance colorless oil, yellowish when impure
Density 0.813 g/cm3
Melting point 21 °C (70 °F; 294 K)
Boiling point 364 °C (687 °F; 637 K)
Insoluble
Hazards
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
3
0
Flash point 154 °C (309 °F; 427 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

Uses

Commercially, it is mainly used as a surfactant or precursor to surfactants.[10]

It has also been used in the laboratory in the synthesis of nanoparticles.[11][12] 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 precursor and affect the formation kinetics of nanoparticles during the synthesis.[12]

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.

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See also

References
  1. Pubchem. "Oleylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-03-10.
  2. "Oleylamine, technical grade 70% (Sigma-Aldrich)". Retrieved March 10, 2019.
  3. "Oleylamine, ≥98% primary amine (Sigma-Aldrich)".
  4. "Oleylamine, min. 95% (Strem Chemicals)". Retrieved March 10, 2019.
  5. "Oleylamine, min. 70% (Strem Chemicals)". Retrieved March 10, 2019.
  6. "Oleylamine, approximate C18-content 80-90% (Acros Organics, catalog number 12954)". Retrieved 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. 31 (4): 1223–1230. doi:10.1021/acs.chemmater.8b04198. ISSN 0897-4756.
  8. Yin, Xi; Wu, Jianbo; Li, Panpan; Shi, Miao; Yang, Hong (January 2016). "Self-Heating Approach to the Fast Production of Uniform Metal Nanostructures". ChemNanoMat. 2 (1): 37–41. doi: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. 12 (2): 1704–1711. doi:10.1021/acsnano.7b08357. ISSN 1936-0851. PMC 5830690. PMID 29381326.
  10. Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
  11. Mourdikoudis, Stefanos; Liz-Marzán, Luis M. (2013-05-14). "Oleylamine in Nanoparticle Synthesis". Chemistry of Materials. 25 (9): 1465–1476. doi:10.1021/cm4000476. ISSN 0897-4756.
  12. Yin, Xi; Shi, Miao; Wu, Jianbo; Pan, Yung-Tin; Gray, Danielle L.; Bertke, Jeffery A.; Yang, Hong (5 September 2017). "Quantitative Analysis of Different Formation Modes of Pt Nanocrystals Controlled by Ligand Chemistry". Nano Letters. 17 (10): 6146–6150. doi:10.1021/acs.nanolett.7b02751. PMID 28873317.
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