Strong Hydrogen Bonds. III. Hydrogen Sulfide-Hydrosulfide Anion Interactions

McDaniel, Darl H.; Evans, W. G.

doi:10.1021/ic50046a022

Cited by 16 publications

(8 citation statements)

References 1 publication

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“…DMEA serves as a representative alkanolamine for the spectral characterization discussion. Similarly to the reported Lewis acid/base adduct in CDCl 3 in Maddox et al 12 there are minor spectral changes in the 1 H and 13 C NMR. We performed NMR analysis on the neat hydrosulfide salts to prevent decomposition of the ionic liquid.…”

Section: Characterization Of Hydrosulfide Ionic Liquidssupporting

confidence: 79%

“…Trialkanolammonium hydrosulfide liquids were characterized by 1 H NMR, infrared spectroscopy (IR) and 13 C NMR. DMEA serves as a representative alkanolamine for the spectral characterization discussion.…”

Section: Characterization Of Hydrosulfide Ionic Liquidsmentioning

confidence: 99%

“…This observation contrasts with studies showing anhydrous trialkylamines such as triethylamine react with H 2 S to form solid hydrosulfide salts. 13 Maddox et al were unable to observe the Lewis acid/base adducts during nuclear magnetic resonance (NMR) characterization because H 2 S evolved readily from solutions of DMEA and MDEA in chloroform (CDCl 3 ) at standard temperature and pressure (STP). For this reason they believed the H 2 S was associated as a Lewis acid/base complex (eqn (1) and ( 2)), and not an ionic species.…”

Section: Introductionmentioning

confidence: 99%

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Chemically selective gas sweetening without thermal-swing regeneration

Koech

Rainbolt

Bearden

et al. 2011

Energy Environ. Sci.

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Natural gas purifications using chemically selective hydrogen sulfide (H 2 S) sorbents could be more efficient if chemical selectivity for H 2 S could be maintained without thermal regeneration of the sorbent. We used tertiary alkanolamines to reversibly capture H 2 S in the absence of water to produce hydrosulfide-based ionic liquids in high yield. These alkanolammonium hydrosulfide ionic liquids release H 2 S by exposure to inert gas or by mild heating. H 2 S can be rapidly and nearly quantitatively released at ambient temperature from the alkanolammonium hydrosulfide ionic liquids by the addition of nonpolar antisolvents, some of which naturally phase separate from the spent alkanolamine. The antisolvent-induced regeneration of the alkanolamine potentially allows an efficient H 2 S gas scrubbing process that is chemically selective and can be operated continuously at or near ambient temperature.

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Section: Characterization Of Hydrosulfide Ionic Liquidssupporting

confidence: 79%

Section: Characterization Of Hydrosulfide Ionic Liquidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemically selective gas sweetening without thermal-swing regeneration

Koech

Rainbolt

Bearden

et al. 2011

Energy Environ. Sci.

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“…The simple neutralization‐metathesis chemistry provides a facile approach to tertiary amine functionalized ILs. Since the interaction of CO 2 with tertiary amine is thermodynamically and kinetically unfavorable due to the absence of active protons in CO 2 molecule, these hydrophobic protic ILs are expected to have high performance in the selective absorption of H 2 S from CO 2 .…”

Section: Introductionmentioning

confidence: 99%

Hydrophobic protic ionic liquids tethered with tertiary amine group for highly efficient and selective absorption of H₂S from CO₂

et al. 2016

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Developing absorbents with both high absorption capacity of H 2 S and large selectivity of H 2 S/CO 2 is very important for natural gas sweetening process. To this end, a class of novel hydrophobic protic ionic liquids (ILs) containing free tertiary amine group as functional site for the absorption of H 2 S were designed in this work. They were facilely synthesized through a simple neutralization-metathesis methodology by utilizing diamine compounds and bis(trifluoromethylsulfonyl)imide as the building blocks for cation and anion, respectively. Impressively, the solubility of H 2 S can reach 0.546 mol mol 21 (1 bar) and 0.225 mol mol 21 (0.1 bar), and the selectivity of H 2 S/CO 2 can reach 37.2 (H 2 S solubility at 1 bar vs. CO 2 solubility at 1 bar) and 15.4 (H 2 S solubility at 0.1 bar vs. CO 2 solubility at 1 bar) in the hydrophobic protic ILs at 298.2 K. Comparing the hydrophobic protic ILs with other absorbents justifies their superior performance in the selective absorption of H 2 S from CO 2 .

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“…Sulfur is generally considered as a weak hydrogen bonding acceptor because of its low electronegativity. However, due to the slight electronegativity difference between H and S (0.38, Pauling scale [20]), sulfur-hydrogen bonding can occur [21][22][23][24]. These sulfur containing hydrogen-bonds play an important role in some biological processes, mainly in structure and function of proteins [25][26][27].…”

mentioning

confidence: 99%

Intra‐ and Inter‐molecular Sulf‐ hydryl Hydrogen Bonding: Facilitating Proton Transfer Events for Determination of pH in Sea Water

Sisodia¹,

Miranda²,

McGuinness³

et al. 2020

Electroanalysis

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This work presents the electrochemical response of a 2‐(methylthio)phenol glassy carbon based electrode for a promising voltammetric pH sensor in both buffered and low‐buffered solutions. Electropolymerization of the redox species was performed with the resulting polymer presenting a Nernstian response in buffered media, with a sensitivity of 51 mV/pH unit. The effectiveness of the sulfhydryl bond to facilitate proton transfer from the bulk solution to the phenol molecules has been confirmed, providing an accurate pH measurement of 8.28 in sea water media, compared to that measured with a calibrated glass pH probe of 8.30.

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Strong Hydrogen Bonds. III. Hydrogen Sulfide-Hydrosulfide Anion Interactions

Cited by 16 publications

References 1 publication

Chemically selective gas sweetening without thermal-swing regeneration

Chemically selective gas sweetening without thermal-swing regeneration

Hydrophobic protic ionic liquids tethered with tertiary amine group for highly efficient and selective absorption of H₂S from CO₂

Intra‐ and Inter‐molecular Sulf‐ hydryl Hydrogen Bonding: Facilitating Proton Transfer Events for Determination of pH in Sea Water

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Strong Hydrogen Bonds. III. Hydrogen Sulfide-Hydrosulfide Anion Interactions

Cited by 16 publications

References 1 publication

Chemically selective gas sweetening without thermal-swing regeneration

Chemically selective gas sweetening without thermal-swing regeneration

Hydrophobic protic ionic liquids tethered with tertiary amine group for highly efficient and selective absorption of H2S from CO2

Intra‐ and Inter‐molecular Sulf‐ hydryl Hydrogen Bonding: Facilitating Proton Transfer Events for Determination of pH in Sea Water

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Product

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Hydrophobic protic ionic liquids tethered with tertiary amine group for highly efficient and selective absorption of H₂S from CO₂