What is 1-Dodecanethiol?

1-Dodecanethiol (C12H26S, CAS registry No. 112-55-0) is also called n-dodecyl mercaptan, which is a clear liquid. Its melting point is -7 oC, and flash point is 87 oC. It is stable under normal temperatures and pressures. Store in a cool and dry place, and keep container closed when not in use. It can cause severe skin burns and eye damage. It may cause an allergic skin reaction. It is very toxic to aquatic life with long lasting effects.

1-Dodecanethiol can be used as a chain transfer agent in the polymerization of methyl methacrylate. For example, the effect of 1-dodecanethiol as a chain transfer agent on the molecular weight of poly(methyl methacrylate) has been studied[1]. The transfer constant of 1-dodecanethiol was calculated at different temperatures; the activation energy and frequency factor for an Arrhenius equation of transfer constant were then obtained.

1-Dodecanethiol, an organic molecular sulfur, has been utilized as the sulfur source for cadmium sulfide (CdS) “magic-sized” quantum dots (MSQDs) production[2]. For example, CdS quantum dot (QD) nanoparticles have been synthesized using a cadmium salt and 1-dodecanethiol, an organic sulfur, as the cadmium and sulfur sources, respectively, along with a long-chain organic acid (myristic acid, lauric acid, or stearic acid). The acid has dual effects as a surface capping ligand and a solubility controlling agent as well. The organic sulfur (1-dodecanethiol) proved to be a useful sulfur source for synthesizing magic-sized CdS QDs. Several distinctive size regimes of magic-sized quantum dots (MSQDs), including Families 378 and 407, were successfully produced by controlling a small number of factors.

1-Dodecanethiol can be used for the synthesis of thiol-stabilized metal nanoparticles (NPs), such as gold nanoparticles and silver nanoparticles, which have been produced for use as catalysts, electronic devices, fillers, sensors and active components in composite materials, and other applications. As an example, silver nanoparticles, which were produced by the borohydride reduction of silver nitrate, were stabilized by means of 1-dodecanethiol providing sulfur atom in two phase system involving water and organic solvent (such as toluene, chloroform and hexane)[3]. Different organic solvent played a major role in the particle size of silver nanoparticles. As a result, 1-dodecanethiol-capped silver nanoparticles were found to serve as effective catalysts to activate the reduction of 4-nitrophenol (4NP) in the presence of NaBH4, where the size of silver nanoparticles played the determining role in catalytic activity.

1-Dodecanethiol can also be used for development of the 1-dodecanethiol-based phase transfer protocol for the highly efficient extraction of noble metal ions from aqueous phase[4]. First, mix the aqueous metal ion solution with an ethanolic solution of 1-dodecanethiol, and then extract the coordination compounds formed between noble metal ions and 1-dodecanethiol into a non-polar organic solvent. A number of characterization techniques, including inductively coupled plasma atomic emission spectroscopy (ICP-AES), Fourier transform infrared spectroscopy (FT-IR), and thermogravimetric analysis (TGA) were used to characterize the coordinating compounds formed between noble metal ions and 1-dodecanethiol, and to address the following critical issues: (1) the transfer efficiency of noble metal ions; (2) the transfer mechanism of this 1-dodecanethiol-based protocol; and (3) the selectivity of this phase transfer protocol for the extraction of noble metal ions.

Fig 1. Chemical structure formula of 1-dodecanethiol

References

[1]. Jahanzad, F.; Kazemi, M.; Sajjadi, S.; Taromi, F. A., n-Dodecyl mercaptan transfer constant in polymerization of methyl methacrylate. Polymer 1993, 34 (16), 3542-3544.

[2]. Dickson, R. E.; Hu, M. Z., Chemical synthesis and optical characterization of regular and magic-sized CdS quantum dot nanocrystals using 1-dodecanethiol. Journal of Materials Research 2015, 30 (7), 890-895.

[3]. Zhang, D.; Yang, Y., Synthesis of 1-dodecanethiol-capped Ag nanoparticles and their high catalytic activity. Applied Physics a-Materials Science & Processing 2017, 123 (1).

[4]. Chen, D.; Cui, P.; Cao, H.; Yang, J., A 1-dodecanethiol-based phase transfer protocol for the highly efficient extraction of noble metal ions from aqueous phase. Journal of Environmental Sciences 2015, 29, 146-150.

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