Synthesis of 2-hydroxyethyl dibutyldithiocarbamate and its adsorption mechanism on chalcopyrite

Huang, Xiaoping; Huang, Kaimin; Wang, Shuai; Cao, Zhanfang; Zhong, Hong

doi:10.1016/j.apsusc.2019.01.053

Cited by 44 publications

(10 citation statements)

References 56 publications

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“…Although many synthetic methods have been developed for thionocarbamate, the use of ethylamine is still unavoidable. , To address this issue, using safer amines as raw materials and preparing products with the same or even better flotation performance are potential solutions. , Hydroxyl groups benefit from the strong electronegativity of oxygen atoms, which can improve the polarity of molecules and the dispersibility of surfactants. Furthermore, our group’s previous studies have also shown that the introduced hydroxyl groups may also interact with the mineral surface and improve the flotation performance of collectors. , Therefore, we speculate that using ethanolamine instead of ethylamine in the synthesis of thionocarbamate can not only avoid the use of irritating amine gas but also enhance its flotation performance via the introduction of a hydroxyl group into the molecule.…”

Section: Introductionmentioning

confidence: 90%

“…Furthermore, our group's previous studies have also shown that the introduced hydroxyl groups may also interact with the mineral surface and improve the flotation performance of collectors. 17,18 Therefore, we speculate that using ethanolamine instead of ethylamine in the synthesis of thionocarbamate can not only avoid the use of irritating amine gas but also enhance its flotation performance via the introduction of a hydroxyl group into the molecule.…”

Section: Introductionmentioning

confidence: 99%

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O-Isobutyl-N-hydroxyethyl Thionocarbamate: Molecular Behavior and Flotation Mechanism to Chalcopyrite

Lin

Wang

et al. 2023

Ind. Eng. Chem. Res.

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Herein, a chelating collector, O-isobutyl-N-hydroxyethyl thionocarbamate (IBHETC), was synthesized by using a safe ethanolamine instead of volatile gas ethylamine, and its molecular behavior and flotation performance for chalcopyrite were carefully investigated. Nuclear magnetic resonance (NMR) (1D and 2D), molecular dynamics (MD) simulations, and density functional theory (DFT) calculations revealed the existence of two isomers similar to cis–trans isomers in IBHETC, owing to the planar nature of the C(S)–N structure in the thionocarbamate group. It was further demonstrated that both isomers undergo the deprotonation–isomerization mechanism after reacting with Cu+, resulting in the formation of an identical IBHETC–(N,O,S)–Cu complex through N, O, and S atoms. The surface tension test, Fourier transform infrared (FTIR), ultraviolet (UV), and X-ray photoelectron spectroscopy (XPS) results revealed that IBHETC selectively adsorbs onto the surface of chalcopyrite to realize hydrophobic flotation through the synergistic behavior of hydroxyl and thionocarbamate groups. This research is expected to promote the molecular design and industrial applications of functional surfactants.

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Section: Introductionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

O-Isobutyl-N-hydroxyethyl Thionocarbamate: Molecular Behavior and Flotation Mechanism to Chalcopyrite

Lin

Wang

et al. 2023

Ind. Eng. Chem. Res.

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“…Initial structures of SBEX and SPEX molecules were first optimized by semi-empirical and PM3 methods. And then, the geometry configuration of BEX and PEX were optimized using an integral equation formalism polarizable continuum model (IEFPCM) method at DFT/B3LYP in conjunction with 6-311+G(d) basis set. ,, In the process of calculation, the parameter of the solvent was water. Finally, the final optimized structures were visualized using Gaussview 5.0.…”

Section: Methodsmentioning

confidence: 99%

“…Computational chemistry has been recognized as important as experimental chemistry in the study of chemical systems, physical and chemical properties in chemical reactions due to the remarkable advances in computing ability and computer programs. , Density functional theory (DFT) calculation owns excellent computational efficiency, and is regarded as a reliable method for obtaining chemical information from energy, structure, and properties of atoms and molecules. , In froth flotation, DFT calculation has also been widely used to evaluate the interface chemical reaction between collector and mineral through the structure–reactivity relationship of flotation collectors, so as to understand the flotation mechanism. − …”

Section: Introductionmentioning

confidence: 99%

Novel Sodium O-Benzythioethyl Xanthate Surfactant: Synthesis, DFT Calculation and Adsorption Mechanism on Chalcopyrite Surface

et al. 2019

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Xanthate with low cost and strong collecting ability has great application in the recovery of sulfide mineral. Herein, a xanthate, sodium O-benzythioethyl xanthate (SBEX), with high collecting ability was prepared by introducing thioether structure, which was constructed by reactive 2-(benzylthio)ethanol, carbon disulfide, and sodium hydroxide. The flotation performance of SBEX to chalcopyrite is yet to be explored by flotation experimental, surface tension measurements, adsorption experimental, density functional theory (DFT) calculations, and X-ray photoelectron spectroscopy (XPS) analyses. It is found that the thioether structure can increase the hydrophobicity and adsorption amount of SBEX on chalcopyrite surface, and SBEX features a higher collecting recovery toward chalcopyrite than sodium isobutyl xanthate (SIBX) and sodium phenylethyl xanthate (SPEX). The adsorption mechanism analyses reveal that two S atoms in the structure of −C(S)–S are the reactive sites that can donate their electrons to minerals, as confirmed by DFT calculations and XPS analyses.

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“…For BETX-Cu 2+ , the peaks of C�S−Cu were located at 162.01 and 162.72 eV. 62,75 Therefore, changes of proportion in BETX-treated chalcopyrite may be the result of the superposition of the peak of disulfifides, polysulfide, and C�S−Cu. 12 The fitted high-resolution Cu 2p 3/2 XPS spectra are listed in Figure 7(D) and Table S7.…”

Section: Investigation On the Flotation Mechanismmentioning

confidence: 99%

A Novel Bipolar Surfactant, BETX, for Selective Flotation of Chalcopyrite: Folding-Synergistic Mechanism Based on Intramolecular Weak Interactions

Lin,

Yang,

Wang

et al. 2024

Ind. Eng. Chem. Res.

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Surfactants with multiple polar groups have shown promising applications, while the molecular mechanism that distinguishes them from conventional surfactants remains unclear. Herein, a novel surfactant, BETX, which contains two polar groups was designed, and the effect of intramolecular interaction on its molecular mechanism was elucidated. MD simulations, DFT calculations, and UV spectroscopy revealed that the BETX molecules fold due to π−π stacking and various other weak interactions, which enhances the binding ability of BETX to Cu 2+ while reducing that to Fe 3+ . Interestingly, the synergism of ionic xanthate groups and nonionic thionocarbamate groups enables the thionocarbamate groups to react with Cu 2+ in aqueous solutions. This selective synergistic behavior endowed BETX with excellent selective flotation ability for chalcopyrite, with a dosage an order of magnitude lower than that of traditional collectors. ToF-SIMS, FTIR, and XPS demonstrated that BETX interacts with chalcopyrite through the xanthate group and the deprotonated thionocarbamate group. Each N and S atom in the molecule can form chemical bonds with copper sites. Comparative assessments of Cu 2+ binding between unfolded bipolar surfactants with rigid structures have confirmed the reinforcing effect of folding synergism in BETX molecules. The revelation of this intramolecular folding-synergistic mechanism holds profound significance, offering crucial insights into the operational mechanisms of multipolar surfactants and facilitating precise molecular design for future advancements.

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Synthesis of 2-hydroxyethyl dibutyldithiocarbamate and its adsorption mechanism on chalcopyrite

Cited by 44 publications

References 56 publications

O-Isobutyl-N-hydroxyethyl Thionocarbamate: Molecular Behavior and Flotation Mechanism to Chalcopyrite

O-Isobutyl-N-hydroxyethyl Thionocarbamate: Molecular Behavior and Flotation Mechanism to Chalcopyrite

Novel Sodium O-Benzythioethyl Xanthate Surfactant: Synthesis, DFT Calculation and Adsorption Mechanism on Chalcopyrite Surface

A Novel Bipolar Surfactant, BETX, for Selective Flotation of Chalcopyrite: Folding-Synergistic Mechanism Based on Intramolecular Weak Interactions

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