Techniques for Overcoming Sulfur Poisoning of Catalyst Employed in Hydrocarbon Reforming

Kumar, Santosh; Appari, Srinivas; Kuncharam, Bhanu Vardhan Reddy

doi:10.1007/s10563-021-09340-w

Cited by 18 publications

(7 citation statements)

References 197 publications

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“…The S adsorption energies are displayed using color coding, where a darker blue color represents a lower value (therefore more prone to S adsorption) and a lighter green represents a higher value (less prone to S adsorption). Based on previous research on the interaction between sulfur and transition metal-based catalysts, , sulfur poisoning takes place through two main routes: the reversible adsorption of sulfur-containing species (at lower concentrations) and the irreversible chemisorption of sulfur due to the formation of metal sulfides. Therefore, having a higher value of S adsorption energy is in general favorable for the catalyst, as it allows for a more difficult adsorption and easier desorption of sulfur species.…”

Section: Resultsmentioning

confidence: 99%

High-Throughput Screening of Sulfur-Resistant Catalysts for Steam Methane Reforming Using Machine Learning and Microkinetic Modeling

Wang,

Kasarapu,

Clough

2024

ACS Omega

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The catalytic activity of bimetallic catalysts for the steam methane reforming (SMR) reaction was extensively studied previously. However, the performance of these materials in the presence of sulfur-containing species is yet to be investigated. In this study, we propose a novel process aided by machine learning (ML) and microkinetic modeling for the rapid screening of sulfur-resistant bimetallic catalysts. First, various ML models were developed to predict atomic adsorption energies (C, H, O, and S) on bimetallic surfaces. Easily accessible physical and chemical properties of the metals and adsorbates were used as input features. The Ensemble learning, artificial neural network, and support vector regression models achieved the best performance with R 2 values of 0.74, 0.71, and 0.70, respectively. A microkinetic model was then built based on the elementary steps of the SMR reaction. Finally, the microkinetic model, together with the atomic adsorption energies predicted by the Ensemble model, were used to screen over 500 bimetallic materials. Four Ge-based alloys (Ge

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Section: Resultsmentioning

confidence: 99%

High-Throughput Screening of Sulfur-Resistant Catalysts for Steam Methane Reforming Using Machine Learning and Microkinetic Modeling

Wang,

Kasarapu,

Clough

2024

ACS Omega

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“…Moreover, the fused ring benzothienyl-substituted ketone 1g was hydrogenated smoothly and delivered the chiral alcohol 2g with 99% yield and 99% ee. The outcomes of varied heteroaromatic substrates with substituted thienyl groups suggested that the sulfur atom had no influence on the catalytic capability of the Ir–( R C , S P , R C )- L6 catalyst, though it usually poisoned catalysts in transition-metal-catalyzed reactions 50 – 53 . In addition, the aromatic β-amino ketones without substituent ( 1h ) or bearing varied electron-withdrawing/electron-donating substituent groups formed admirable enantioselectivities of 97–99% ee and good to excellent yields of 77–98%, regardless in the meta - or para -position on the phenyl ring ( 2h – 2u ).…”

Section: Resultsmentioning

confidence: 99%

Iridium-catalyzed enantioselective synthesis of chiral γ-amino alcohols and intermediates of (S)-duloxetine, (R)-fluoxetine, and (R)-atomoxetine

et al. 2022

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Chiral γ-amino alcohols are the prevalent structural motifs and building blocks in pharmaceuticals and bioactive molecules. Enantioselective hydrogenation of β-amino ketones provides a straightforward and powerful tool for the synthesis of chiral γ-amino alcohols, but the asymmetric transformation is synthetically challenging. Here, a series of tridentate ferrocene-based phosphine ligands bearing modular and tunable unsymmetrical vicinal diamine scaffolds were designed, synthesized, and evaluated in the iridium-catalyzed asymmetric hydrogenation of β-amino ketones. The system was greatly effective to substrates with flexible structure and functionality, and diverse β-tertiary-amino ketones and β-secondary-amino ketones were hydrogenated smoothly. The excellent reactivities and enantioselectivities were achieved in the asymmetric delivery of various chiral γ-amino alcohols with up to 99% yields, >99% ee values, and turnover number (TON) of 48,500. The gram-scale reactions with low catalyst loading showed the potential application in industrial synthesis of chiral drugs, such as (S)-duloxetine, (R)-fluoxetine, and (R)-atomoxetine.

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“…In addition, iodobenzenes bearing electron‐donating groups, such as −OMe ( 2 ad ) and −NMe 2 ( 2 ae ), were also viable electrophiles, providing good yields (71–75 %). Employing meta ‐substituted 1,3‐ bis (trifluoromethyl)‐5‐iodobenzene ( 2 ai ) gave 71 % yield, and using an ortho ‐substituted iodothioanisole ( 2 aj ) was also successful; a moderate yield (51 %) was observed as a result of the steric effect or a possible catalyst poisoning by sulphidation [21] . Additionally, a variety of heteroaryl electrophiles were explored.…”

Section: Methodsmentioning

confidence: 99%

“…Employing metasubstituted 1,3-bis(trifluoromethyl)-5-iodobenzene (2 ai) gave 71 % yield, and using an ortho-substituted iodothioanisole (2 aj) was also successful; a moderate yield (51 %) was observed as a result of the steric effect or a possible catalyst poisoning by sulphidation. [21] Additionally, a variety of heteroaryl electrophiles were explored. Both electrondeficient and electron-rich heteroarenes could be employed, It should be emphasized that the unique selectivity [22] of iodides as electrophiles enabled good compatibility with other halogens (2 m, 2 ah), pseudo-halogens (2 ag) and boronic esters (2 af), which could be used as pre-installed oxidation states for subsequent transition-metal catalyzed coupling reactions.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Carbonylative Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates

Zhang

Newhouse

2023

Angew Chem Int Ed

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This report describes the first example of palladium‐catalyzed carbonylative difunctionalization of unactivated alkenes initiated by enolate nucleophiles. The approach involves initiation by an unstabilized enolate nucleophile under an atmospheric pressure of CO and termination with a carbon electrophile. This process is compatible with a diverse range of electrophiles, including aryl, heteroaryl, and vinyl iodides to yield synthetically useful 1,5‐diketone products, which were demonstrated to be precursors for multi‐substituted pyridines. A Pd(I)‐dimer complex with two bridging CO units was observed although its role in catalysis is not yet understood

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Techniques for Overcoming Sulfur Poisoning of Catalyst Employed in Hydrocarbon Reforming

Cited by 18 publications

References 197 publications

High-Throughput Screening of Sulfur-Resistant Catalysts for Steam Methane Reforming Using Machine Learning and Microkinetic Modeling

High-Throughput Screening of Sulfur-Resistant Catalysts for Steam Methane Reforming Using Machine Learning and Microkinetic Modeling

Iridium-catalyzed enantioselective synthesis of chiral γ-amino alcohols and intermediates of (S)-duloxetine, (R)-fluoxetine, and (R)-atomoxetine

Palladium‐Catalyzed Carbonylative Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates

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