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 |
PubChem CID |
|
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 | |
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
- ↑ Oleylamine at chemicaldictionary.org
- ↑ Technical grade Oleylamine on Sigma-Aldrich
- ↑ 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.
- ↑ 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
- ↑ 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.
- 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.