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Solid–liquid separation of lignocellulosic sugars from biomass by rotating ceramic disc filtration† 旋转陶瓷盘过滤法从生物质中分离木质纤维素糖的固液分离技术†。
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc04533e
Patrick O. Saboe , Yudong Li , Emily G. Tomashek , Eric C. D. Tan , Xiaowen Chen , Louis A. Chirban , Yian Chen , Daniel J. Schell , Eric M. Karp , Gregg T. Beckham
{"title":"Solid–liquid separation of lignocellulosic sugars from biomass by rotating ceramic disc filtration†","authors":"Patrick O. Saboe ,&nbsp;Yudong Li ,&nbsp;Emily G. Tomashek ,&nbsp;Eric C. D. Tan ,&nbsp;Xiaowen Chen ,&nbsp;Louis A. Chirban ,&nbsp;Yian Chen ,&nbsp;Daniel J. Schell ,&nbsp;Eric M. Karp ,&nbsp;Gregg T. Beckham","doi":"10.1039/d4gc04533e","DOIUrl":"10.1039/d4gc04533e","url":null,"abstract":"<div><div>In many biomass conversion processes, the separation of cellulosic sugars from residual, lignin-rich solids is a critical step, and achieving high recovery yields of sugars by conventional tangential crossflow and vacuum filtration is challenged by the presence of biomass solids, which rapidly foul filters, resulting in decreased throughput. Considering the performance limitations of traditional filtration methods, dynamic filtration, which generates high shear at the membrane surface to decrease fouling, is emerging as a viable alternative for demanding solid–liquid separations. For high solids separations, there is little available information regarding the performance, limitations, and energy consumption of dynamic filtration. To that end, here we characterized the performance of a dynamic filtration module, specifically a rotating ceramic disc (RCD) filter, for the aseptic recovery of cellulosic sugars from biomass solids following pretreatment and enzymatic hydrolysis. We show how RCD rotational velocity and percent biomass solids impact the filter throughput. Additionally, we used computational fluid dynamics (CFD) simulations to estimate the shear rate at the membrane surface and to visualize hydrodynamic profiles within the module. With the combined CFD simulations and experimental results, we estimated the energy demand and operating expenses for a viable dynamic filtration system operating with a lignocellulosic feed slurry. Our results indicate that an RCD filter can achieve ≥95% recovery of sugars and produce a retentate slurry containing 12 wt% insoluble solids with low energy consumption (a 2.2-fold improvement over cross-flow filtration) and low operating costs ($0.06 per kg sugars). These results show a viable path towards operationally reliable, energy efficient, and cost-effective separations of sterilized cellulosic sugars from biomass solids and highlight the potential of dynamic filtration systems for challenging solid–liquid separations.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11587-11599"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc04533e?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714038","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Does enzymatic catalysis lead to more sustainable chemicals production? A life cycle sustainability assessment of isopropyl palmitate† 酶催化是否能带来更可持续的化学品生产?棕榈酸异丙酯的生命周期可持续性评估†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc04514a
Pieter Nachtergaele , Ozan Kocak , Yblin Roman Escobar , Jordy Motte , Dries Gabriels , Leopold Mottet , Jo Dewulf
{"title":"Does enzymatic catalysis lead to more sustainable chemicals production? A life cycle sustainability assessment of isopropyl palmitate†","authors":"Pieter Nachtergaele ,&nbsp;Ozan Kocak ,&nbsp;Yblin Roman Escobar ,&nbsp;Jordy Motte ,&nbsp;Dries Gabriels ,&nbsp;Leopold Mottet ,&nbsp;Jo Dewulf","doi":"10.1039/d4gc04514a","DOIUrl":"10.1039/d4gc04514a","url":null,"abstract":"<div><div>In this work, a comprehensive Life Cycle Sustainability Assessment (LCSA) is performed assessing environmental, economic and social impacts of switching from chemical to enzymatic catalysis for the esterification of Isopropyl palmitate (IPP). A dedicated LCSA methodology with a common goal, system boundary and life cycle inventory is presented. A 7 to 13% reduction in environmental impacts was found due to less hazardous waste formation, lower feedstock consumption and reduced steam usage. The social medium risk hours increase by 9% due to a longer production time, however, certain social benefits which were identified by stakeholder interviews, such as improved safety for workers, are not properly captured by the social impacts database used. Despite reductions in utility and feedstock costs, the total operating costs are higher (+40%) due to the immobilized enzyme cost and higher labour costs. Nevertheless, profitability indicators show that switching to enzymatic production is likely to be profitable. To reduce costs, optimization efforts should focus on reducing the batch time and increasing enzyme reuse. From a social and environmental perspective, upstream impacts linked to palmitic acid and isopropyl alcohol production should be addressed.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11662-11672"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc04514a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714054","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Postliminary treatment of food-waste digestate via combined hydrothermal carbonization and microbial fuel cell for bio-energy recovery: a comparative life cycle impact assessment† 通过组合式热液碳化和微生物燃料电池对食物垃圾沼渣进行初步处理以回收生物能源:生命周期影响比较评估†。
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc04081c
Shraddha Yadav , Manikanta M. Doki , Makarand M. Ghangrekar , Brajesh K. Dubey
{"title":"Postliminary treatment of food-waste digestate via combined hydrothermal carbonization and microbial fuel cell for bio-energy recovery: a comparative life cycle impact assessment†","authors":"Shraddha Yadav ,&nbsp;Manikanta M. Doki ,&nbsp;Makarand M. Ghangrekar ,&nbsp;Brajesh K. Dubey","doi":"10.1039/d4gc04081c","DOIUrl":"10.1039/d4gc04081c","url":null,"abstract":"<div><div>Anaerobic digestion (AD) is the predominant technique for transforming food-waste into biomethane, yet the dewatering and valorisation of the resultant digestate present a significant downstream technical challenge. This investigation provides an advanced digestate management approach for resource recovery through the synergistic integration of hydrothermal carbonization (HTC) with anaerobic digestion. The integrated system resulted in biomethane (∼466 mL g<sup>−1</sup> VS) and biocoal (hydrochar) with a high calorific value (∼22 MJ kg<sup>−1</sup>). The effect of HTC operating conditions including reaction temperature and time on the coalification degree has been investigated. Additionally, the by-product of HTC, <em>i.e.</em>, HTC process water was treated using the microbial fuel cell (MFC) with organic abatement efficiency of 76.0 ± 4.6% and power recovery of ∼4.41 W m<sup>−3</sup>. Further, the metagenomic analysis was conducted to affirm the high proliferation of specific electrogens (<em>Clostridia</em>) in the MFC. Distinctively, in this work, the impacts on the environment in eighteen different categories using life cycle assessment for the technologies AD, AD + HTC, and AD + HTC + MFC were also compared. The single score results demonstrated the least impact of the integrated AD + HTC + MFC on human health, ecosystem, and resource depletion. This highlights the potential of the integrated system for real-field applicability, sustainable digestate management, and bioenergy recovery.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11673-11685"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714055","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Flow electrosynthesis of phosphinamides and phosphoramidates through P–N coupling† 通过 P-N 偶联实现膦酰胺和膦酰胺酸盐的流动电合成†。
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc04450a
Tribani Boruah , Ren Ishizeki , Alberto Roldan , Rebecca L. Melen , Thomas Wirth
{"title":"Flow electrosynthesis of phosphinamides and phosphoramidates through P–N coupling†","authors":"Tribani Boruah ,&nbsp;Ren Ishizeki ,&nbsp;Alberto Roldan ,&nbsp;Rebecca L. Melen ,&nbsp;Thomas Wirth","doi":"10.1039/d4gc04450a","DOIUrl":"10.1039/d4gc04450a","url":null,"abstract":"<div><div>A robust flow electrochemical methodology operating under mild reaction conditions for P–N and P–O oxidative coupling has been developed. Potentiostatic and galvanostatic electrolyses were used to investigate reactant redox behaviour, showcasing a broad substrate scope (47 examples, up to 85% yield) across various chemical contexts.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11722-11727"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc04450a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714060","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Rational design of the La-doped CuCoAl hydrotalcite catalyst for selective hydrogenation of furfuryl alcohol to 1,5-pentanediol† 用于糠醇选择性加氢制 1,5-戊二醇的掺镧铜铝氢铝酸盐催化剂的合理设计†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc03974b
Jingjing Tan , Hailong Huang , Yuanna Zhang , Jinglei Cui , Jing Zhang , Long Huang , Yongzhao Wang , Yulei Zhu
{"title":"Rational design of the La-doped CuCoAl hydrotalcite catalyst for selective hydrogenation of furfuryl alcohol to 1,5-pentanediol†","authors":"Jingjing Tan ,&nbsp;Hailong Huang ,&nbsp;Yuanna Zhang ,&nbsp;Jinglei Cui ,&nbsp;Jing Zhang ,&nbsp;Long Huang ,&nbsp;Yongzhao Wang ,&nbsp;Yulei Zhu","doi":"10.1039/d4gc03974b","DOIUrl":"10.1039/d4gc03974b","url":null,"abstract":"<div><div>1,5-Pentanediol (1,5-PeD) is an important raw material for the preparation of degradable polyesters, polyurethanes and pharmaceutical intermediates. Efficient synthesis of 1,5-PeD from biomass-derived furfuryl alcohol (FFA) by hydrogenation is a green synthetic route instead of using fossil raw material production. Nevertheless, it suffers from great challenges as the various adsorption configurations of FFA on the catalyst surface induce diverse product distributions and low selectivity for 1,5-PeD. Herein, a CuCoAl hydrotalcite catalyst modified by La was fabricated and applied in the hydrogenation of FFA to 1,5-PeD. The results demonstrated that in the catalyst doped with La <em>via</em> deposition–precipitation methods (La/CuCoAl-DP) there appeared a strong Cu–La interaction, and it exhibited superior activity compared with other catalysts. A near 60% yield of 1,5-PeD was achieved under 160 °C, 4 MPa H<sub>2</sub> within 2 h. Extensive characterizations including XRD, HRTEM, N<sub>2</sub>O-TPD and CO<sub>2</sub>-TPD demonstrated that the doping of La improved markedly the dispersion of Cu and the concentration of strong basic sites. Furthermore, HRTEM and the <em>in situ</em> XPS characterization verified that the addition of La species promoted the formation of a Cu–La interface with a stable Cu<sup><em>n</em>+</sup>–O–La(OH)<sub>3</sub> structure on the catalyst surface. Such Cu<sup><em>n</em>+</sup>–O–La(OH)<sub>3</sub> sites can simultaneously activate the furan ring and the –OH group in FFA with an intermediate six-membered ring transition state, leading to high selective cleavage of the C2–O1 bond in the furan ring to 1,5-PeD. Meanwhile, the DFT calculation results corroborated that the modifying by La species remarkably promoted the C2-end tilted adsorption of FFA on the catalyst surface and enhanced the ability of the catalyst to activate hydrogen. This study provided a new strategy for the high-value utilization of biomass resources and the development of multi-center catalysts.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11608-11624"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc03974b?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714040","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A multiscale graph neural network for predicting the properties of high-density cycloalkane-based diesel and jet range biofuels† 用于预测高密度环烷基柴油和喷气范围生物燃料特性的多尺度图神经网络†。
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc02621g
Yanqiu Yao , Yizhuo Wang , Zhanchao Li , Jing Wang , Hong Wang
{"title":"A multiscale graph neural network for predicting the properties of high-density cycloalkane-based diesel and jet range biofuels†","authors":"Yanqiu Yao ,&nbsp;Yizhuo Wang ,&nbsp;Zhanchao Li ,&nbsp;Jing Wang ,&nbsp;Hong Wang","doi":"10.1039/d4gc02621g","DOIUrl":"10.1039/d4gc02621g","url":null,"abstract":"<div><div>Predicting the fuel properties using computer techniques can speed up the search for alternatives to replace fossil-based diesel and jet fuels and lower research costs. However, previously reported graph neural network (GNN) models are not suitable for the fuel property prediction of biofuels with ring structures, such as cycloalkane-based high-density biofuels, because GNNs with a limited number of layers are inadequate for capturing the global structure of compounds. In this work, we proposed a multiscale graph neural network (MGNN) model to estimate the fuel properties of cycloalkane-based diesel and jet-range biofuels. The MGNN model increased the receptive field of each node, allowing nodes to perceive topological and feature information from a larger neighborhood, which enhanced the complexity and capacity of the model, thereby improving its fitting ability. Traditional over-smoothing issues in the MGNN were overcome by introducing dense connections, which maintained the distinctiveness of vertex embedding and preserved substructure details. The coefficients of determination of the linear regressions (<em>R</em><sup>2</sup>) were all in the range of &gt;0.98 with smaller mean relative errors (MREs) and a narrower range of error distribution compared to conventional GNN models. A detailed analysis of the relationship between these properties and various topological descriptors was discussed. The results show a promising and accurate method for estimating the fuel properties of cycloalkane-based diesel and jet-range biofuels.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11625-11635"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714041","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Controllable tertiary amine-promoted photoactivation metal-free carbonylation of aryl sulfonium salts to aryl carboxylic acid derivatives† 芳基锍盐与芳基羧酸衍生物的可控叔胺促进光活化无金属羰基化反应†。
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc04502e
Jiajun Zhang , Le-Cheng Wang , Yuanrui Wang , Xiao-Feng Wu
{"title":"Controllable tertiary amine-promoted photoactivation metal-free carbonylation of aryl sulfonium salts to aryl carboxylic acid derivatives†","authors":"Jiajun Zhang ,&nbsp;Le-Cheng Wang ,&nbsp;Yuanrui Wang ,&nbsp;Xiao-Feng Wu","doi":"10.1039/d4gc04502e","DOIUrl":"10.1039/d4gc04502e","url":null,"abstract":"<div><div>Conventional transition metal-catalyzed carbonylative reactions are a powerful tool for the direct incorporation of electrophilic reagents, CO, and nucleophilic reagents into high-value-added products. Although these metal-catalyzed carbonylation strategies can efficiently synthesize carbonylated compounds, metal-free systems remain an attractive direction in carbonylative reactions. Inspired by the achievements in metal-free radical carbonylation, herein we describe a photochemical method for the carbonylation of aryl sulfonium salts using photoexcitation of electron donor–acceptor (EDA) complexes. This strategy is metal-free and widely applicable, enabling ready access to a wide range of aryl carboxylic acid derivatives in a simplified manner. Notably, by choosing different amines, the reaction intermediates can be captured and then quenched stepwise. It has the potential to be a direct green alternative to conventional carbonylation methods for the synthesis of aryl carboxylic acid derivatives.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11686-11694"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc04502e?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714056","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Advancing green chemistry in environmental monitoring: the role of electropolymerized molecularly imprinted polymer-based electrochemical sensors 推进环境监测中的绿色化学:基于电聚合分子印迹聚合物的电化学传感器的作用
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc03250k
Christopher Mwanza , Wei-Zhi Zhang , Kalulu Mulenga , Shou-Nian Ding
{"title":"Advancing green chemistry in environmental monitoring: the role of electropolymerized molecularly imprinted polymer-based electrochemical sensors","authors":"Christopher Mwanza ,&nbsp;Wei-Zhi Zhang ,&nbsp;Kalulu Mulenga ,&nbsp;Shou-Nian Ding","doi":"10.1039/d4gc03250k","DOIUrl":"10.1039/d4gc03250k","url":null,"abstract":"<div><div>Molecularly imprinted polymers (MIPs) are synthetic materials designed to mimic the natural “lock and key” mechanism observed in biomolecular systems, such as the interactions between antibodies and antigens. As recognition elements, MIPs exhibit high selectivity and affinity toward both biological and chemical targets, making them suitable for various analytical applications. This tutorial review provides a comprehensive and critical assessment of the existing literature on MIPs, with a particular emphasis on those synthesized through electropolymerization—herein referred to as electropolymerized MIPs (eMIPs)—and their application in the development of molecularly imprinted electrochemical sensors (MIES) specifically designed for environmental monitoring. The synthesis of molecularly imprinted polymers (MIPs) is a critical aspect of their development, involving various techniques, among which, there's electropolymerization (also known as electrochemical polymerization). This scholarly article attempts to position electropolymerization as a superior and more environmentally sustainable method for the synthesis of MIPs, that is, electrochemically synthesized MIPs (eMIPs). Compared to traditional MIP synthesis methods, such as bulk, precipitation, or solution polymerization, electrochemical polymerization offers significant advantages in terms of precision, reproducibility, and environmental sustainability, among many others. Its ability to precisely control MIP film thickness on the surface of the transducer makes it a more efficient, reliable, and facile method for fabricating electrochemical sensors. This perspective further examines the application of such sensors based on research from the past five years (2019–2024), exploring cutting-edge MIES methodologies that utilize eMIPs for the sensitive and selective detection of diverse environmental pollutants. It not only underscores electropolymerization as a superior and eco-friendly MIP synthesis technique but also addresses prevailing challenges within the field and proposes actionable solutions. By incorporating sustainable practices in the synthesis of eMIPs, electropolymerization enhances environmental monitoring and contributes to broader goals of sustainability and pollution monitoring. This perspective highlights the transformative potential of eMIPs in advancing green chemistry and environmental monitoring technologies, reaffirming their sustainability in the fabrication of MIESs and showcasing their latest practical applications in environmental monitoring.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11490-11517"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142713992","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A sustainable lecithin-based ligand for the bio-functionalization of iron and hybrid metal organic frameworks (MOFs) nanoparticles with the sugar mannose† 一种基于卵磷脂的可持续配体,用于铁和混合金属有机框架(MOFs)纳米粒子与甘露糖的生物功能化
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc03743j
Camilla M. Cova , Víctor Ramos , Alberto Escudero , Juan P. Holgado , Noureddine Khiar , Alessio Zuliani
{"title":"A sustainable lecithin-based ligand for the bio-functionalization of iron and hybrid metal organic frameworks (MOFs) nanoparticles with the sugar mannose†","authors":"Camilla M. Cova ,&nbsp;Víctor Ramos ,&nbsp;Alberto Escudero ,&nbsp;Juan P. Holgado ,&nbsp;Noureddine Khiar ,&nbsp;Alessio Zuliani","doi":"10.1039/d4gc03743j","DOIUrl":"10.1039/d4gc03743j","url":null,"abstract":"<div><div>The functionalization of nanoparticles with specific ligands, such as antibodies, peptides, and small molecules, plays a critical role in achieving targeted delivery, enhancing biocompatibility, and controlling drug release. However, to date, practically no attention has been paid to the design of green ligands. Herein, an innovative approach to develop a sustainable ligand for nanoparticle functionalization is reported. Its synthesis involved a photochemical thio–ene “click” reaction between the natural compounds phosphatidylcoline, the main component of lecithin, and cysteine, followed by a reductive amination with mannose, a sugar of growing interest for biomedical targeting, in a continuous flow hydrogenation reactor. Comprehensive characterization techniques, including nuclear magnetic resonance (NMR), mass spectrometry (MS), Fourier-transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS) and elemental analysis, confirmed the structure and properties of the novel ligand. The environmental sustainability of the ligand was evaluated determining some green metrics using the EATOS software. The obtained <em>E</em>-factor was compared with a conventional PEG-based ligand. The newly developed lecithin-derived ligand was successfully used to functionalize diverse NP platforms, including the MOFs MIL-101(Fe), PCN-222, UiO-66, and iron nanoparticles (in the form of akaganeite), demonstrating its potential in nanomedicine applications.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11563-11575"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/gc/d4gc03743j?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714037","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Visible light-driven α-sulfonylation of ketone-derived silyl enol ethers via an electron donor–acceptor complex† 通过电子供体-受体复合物,以可见光驱动酮基硅烷烯醇醚的α-磺酰化反应†
IF 9.3 1区 化学
Green Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4gc04554h
Barakha Saxena , Roshan I. Patel , Anuj Sharma
{"title":"Visible light-driven α-sulfonylation of ketone-derived silyl enol ethers via an electron donor–acceptor complex†","authors":"Barakha Saxena ,&nbsp;Roshan I. Patel ,&nbsp;Anuj Sharma","doi":"10.1039/d4gc04554h","DOIUrl":"10.1039/d4gc04554h","url":null,"abstract":"<div><div>The diverse utility of β-ketosulfones in pharmaceuticals and bioactive compounds has generated considerable interest in their synthesis. However, existing synthetic approaches often depend on transition-metal catalysts, which require extensive purification and result in low yields. Herein, we present a cost-effective, metal- and photocatalyst-free, visible light electron donor–acceptor (EDA) complex-mediated sulfonylation of ketone-derived silyl enol ethers with thiosulfonates (acceptor) and DABCO as an electron donor under mild conditions, offering a more efficient and straightforward approach. Our method enables the synthesis of a diverse range of β-ketosulfone derivatives, including biologically active and late-stage molecules, in good yields. Our strategy offers several significant advantages over existing techniques, which include (i) transition-metal and photoredox catalyst-free conditions; (ii) no need for an external SO<sub>2</sub> source; (iii) broad substrate scope; (iv) recyclable and reusable by-products; and (v) excellent atom economy, reaction mass efficiency, process mass intensity, and <em>E</em>-factor and EcoScale scores, highlighting its efficiency and economic sustainability. Detailed mechanistic studies confirm the involvement of an EDA-complex-mediated radical process that operates without a catalyst.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 23","pages":"Pages 11650-11661"},"PeriodicalIF":9.3,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142714053","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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