Oleylamine

Oleylamine[1]
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
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 codeNFPA 704 four-colored diamond
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

Oleylamine is the organic compound with the formula C18H35NH2. It is an unsaturated fatty amine related to the fatty acid oleic acid. Although the pure compound is a colorless oil, typical commercial samples are yellowish and contain a few percent other fatty amines.[2]

Chemical reactions

Oleylamine reacts with carboxylic acid to form its carboxylate salt through an exothermic reaction[3]. 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.[4]

It has also been used in the laboratory in the synthesis of nanoparticles.[5][6] 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.[6]

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.

See also

References

  1. ↑ Oleylamine at chemicaldictionary.org
  2. ↑ Technical grade Oleylamine on Sigma-Aldrich
  3. ↑ 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.
  4. ↑ 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
  5. ↑ 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.
  6. 1 2 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. doi:10.1021/acs.nanolett.7b02751.
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