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sulfonation of Hydroxymethylated Lignin and Its Application

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Journal of Bioresources and Bioproducts 2019年第2期4卷 80-88页

作者： Weijue GAOD John P.W.INWOODD Pedram FATEHI Department of Chemical Engineering and Green Processes Research Centre Lakehead University955 Oliver RoadThunder Bay P7B5E1Canada

To valorize kraft lignin,hydroxymethylation and sulfonation were applied on this under-utilized,but vastly available,material.The hydroxymethylation pretreatment was conducted as means to improve the reactivity of lignin.The sulfonation of hydroxymethylated kraft lignin was investigated by sulfuric acid and sodium sulfite treatments under various conditions.The modified lignin samples were characterized for their charge density,solubility,elemental components,and molecular weights.The results showed that the hydroxymethylation facilitated the sulfonation by sodium sulfite,yielding a product(SSH-lignin)with the charge density of-1.2 meq/g and water solubility of 10 g/L under the conditions of Ns_(2)SO_(3)/lignin molar ratio of 0.49 mol/mol,95℃and 3 h.On the other hand,hydroxymethylation hindered the sulfonation of lignin by sulfuric acid,yielding a product(SAH-lignin)with the charge density of–0.46 meq/g and solubility of 0.9 g/L under the conditions of H_(2)SO_(4)/lignin molar ratio of 14.8 mol/mol,80℃and 1 h.The SSH-lignin had a high adsorption on kaolinite(17 mg/g)at a lignin concentration of 40 g/L.The sulfonated lignins were also found to be effective coagulant for the cationic dye ethyl violet.

关键词： kraft lignin hydroxymethylation sulfonation adsorption dye removal

Implications from γ-globulin adsorption onto cation exchangers fabricated by sequential alginate grafting and sulfonation

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Chinese Journal of Chemical Engineering 2021年第1期34卷 121-125页

作者： Xianxiu Li Yan Sun Xiaoyan Dong Department of Biochemical Engineering School of Chemical Engineering and TechnologyTianjin UniversityTianjin 300354China Key Laboratory of Systems Bioengineering and Frontiers Science Center for Synthetic Biology(Ministry of Education) Tianjin UniversityTianjin 300072China

Our previous work proved that high adsorption capacity and uptake rate of lysozyme were achieved on alginate(Alg)-grafted re sin with an ionic capacity(IC) of 240 mmol·L^(-1)(Alg-FF-240).Moreover,the salt-tolerant feature of Alg-FF-230 was improved by using sequential alginate grafting and sulfonation strategy.Inspired by the enhanced adsorption performance of lysozyme,we have herein proposed to investigate the static and dynamic adsorption behaviors of γ-globulin on a series of Alg-grafted resins with different grafting densities and sulfonation degrees.The adsorption ca pacity of γ-globulin decreased with increa sing alginate-grafting density(IC) from 160 to 230 mmol·L^(-1) at 0 mmol·L^(-1) NaCl because of the steric hindrance caused by the alginate-grafting layer.Effects of ionic strength(IS) indicated that the adsorption capacities of the resins with the IC value of 230-370 mmol·L^(-1) were much higher than CM Sepharose FF at 50-100 mmol·L^(-1) NaCl,and the uptake rate of Alg-FF-230 was about twice as much as that of CM Sepharose FF.This work demonstrated the important effects of alginate-grafting layer and IS in γ-globulin adsorption behavior,which would be helpful in the design of Alggrafted resins and the selection of proper IS condition for protein purification.

关键词： Alginate sulfonation γ-Globulin Adsorption capacity Uptake rate

Gaseous sulfur trioxide induced controllable sulfonation promoting biomineralization and osseointegration of polyetheretherketone implants

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Bioactive Materials 2020年第4期5卷 1004-1017页

作者： Teng Wan Zixue Jiao Min Guo Zongliang Wang Yizao Wan Kaili Lin Qinyi Liu Peibiao Zhang Key Laboratory of Polymer Ecomaterials Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun130022PR China Department of Orthopaedics The Second HospitalJilin UniversityChangchun130041PR China Institute of Advanced Materials East China Jiaotong UniversityNanchang330013PR China Department of Oral&Cranio-Maxillofacial Surgery Shanghai Ninth People's HospitalShanghai Jiao Tong University School of MedicineShanghai Key Laboratory of StomatologyShanghai Research Institute of StomatologyShanghai200011PR China University of Science and Technology of China Hefei230026PR China

Fabricating a desired porous structure on the surface of biomedical polyetheretherketone(PEEK)implants for enhancing biological functions is crucial and difficult due to its inherent chemical inertness.In this study,a porous surface of PEEK implants was fabricated by controllable sulfonation using gaseous sulfur trioxide(SO3)for different time(5,15,30,60 and 90 min).Micro-topological structure was generated on the surface of sulfonated PEEK implants preserving original mechanical properties.The protein absorption capacity and apatite forming ability was thus improved by the morphological and elemental change with higher degree of sulfonation.In combination of the appropriate micromorphology and bioactive sulfonate components,the cell adhesion,migration,proliferation and extracellular matrix secretion were obviously enhanced by the SPEEK-15 samples which were sulfonated for 15 min.Finding from this study revealed that controllable sulfonation by gaseous SO3 would be an extraordinarily strategy for improving osseointegration of PEEK implants by adjusting the microstructure and chemical composition while maintaining excellent mechanical properties.

关键词： Polyetheretherketone sulfonation Micro-topology Mechanical strength Osteointegration

Rheological property of low-damage,ideal packing,film-forming amphoteric/sulfonation polymer drilling fluids

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Journal of Central South University 2008年第S1期15卷 429-433页

作者：张洪霞鄢捷年舒勇赵胜英 Ministry of Education Key Laboratory of Petroleum Engineering China University of Petroleum(Beijing)

Low-permeability dense reservoirs,including micro-fractured reservoirs,are commonly characterized by high content of clay substances,high original water saturation,high sensitivity to invasive fluids,high capillary pressure,complicated structure and anisotropic,high flow-resistance and micro pore throats etc,.Generally they also have lots of natural micro fractures,probably leading to stress sensibility.Main damaging factors in such reservoirs are water-sensibility and water-blocking caused by invasive fluids during drilling and production operations.Once damaged,formation permeability can rarely recovered.Numerous studies have shown that damaging extent of water-blocking ranges from 70% to 90%.Main damaging mechanisms and influencing factors of water-blocking were systematically analyzed.Also some feasible precaution or treating approaches of water-blocking were put forward.In a laboratory setting,a new multi-functional drilling fluid composed mainly of amphion polymer,sulfonation polymer,high effectively preventive water-blocking surfactants,ideal packing temporary bridging agents(TBA) and film-forming agents,etc.,were developed.New low-damage drilling fluids has many advantages,such as good rheological properties,excellent effectiveness of water-blocking prevention,good temporary plugging effect,low filtration and ultra-low permeability(API filtration≤5 mL,HTHP filtration≤10 mL,mud cake frictional coefficient≤0.14,permeability recovery>81%),can efficiently prevent or minimize damage,preserve natural formation and enhance comprehensive development-investment effect in TUHA Jurassic dense sandstone reservoir formation with low-permeability,the only one developing integrated condense gas field.Some references can be provided to similar reservoir formations.

关键词： low-permeability dense gas condense reservoir amphion and sulfonation polymer drilling fluid damage controlling water-blocking ideal packing theory(IPT) film-forming agent rheological properties

EFFECT OF SOLVENT COMPOSITION ON THE sulfonation DEGREE OF POLY(PHENYLENE OXIDE) (PPO)

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Chinese Journal of Polymer Science 2002年第1期20卷 53-57页

作者：徐铜文 Department of Applied Chemistry University of Science and Technology of China Hefei 230026 China The State Key Lab of Func. Polymeric Materials for Adsorp. and Separ Nankai University Tianjin 300071 China

This paper investigates the possibility of attaining sulphonated poly(phenylene oxide) (SPPO) with a relativelyhigher sulfonation degree. To achieve this aim, the approach we adopt is to improve the solubility of the final product in themixed solvent so that the sulfonation may take place between the bulk solutions and PPO powders even at higher sulfonationdegree. It is shown that the addition of a proper amount of dimethyl formide (DMF) to the conventional PPO-chloroformsystem can actually enhance the sulfonation effect. The solvent composition is then correlated with the sulfonation degreebased on the solubility parameters. It is interesting to find that solubility parameters between the mixed solvent and theprecipitated products keep an approximately unchanged value at about 4.9, which is just equal to that when pure chloroformis used, though the solubility parameters of both solvents increase with the content of DMF in solution. This may be the mainreason why the addition of DMF can reduce the precipitation and improve the ion exchange capacity (IEC) of SPPOpolymer.

关键词： Poly(phenylene oxide) sulfonation Solubility parameter

Enhancing Hydrophilicity of Thick Electrodes for High Energy Density Aqueous Batteries

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Nano-Micro Letters 2023年第7期15卷 110-121页

作者： Jungeun Lee Hyeonsoo Lee Cheol Bak Youngsun Hong Daeha Joung Jeong Beom Ko Yong Min Lee Chanhoon Kim Sustainable Technology and Wellness R&D Group Korea Institute of Industrial Technology(KITECH)102 Jejudaehak-RoJeju-SiJeju-do 63243Republic of Korea Department of Energy Science and Engineering Daegu Gyeongbuk Institute of Science and Technology(DGIST)Daegu 42988Republic of Korea Department of Physics Virginia Commonwealth UniversityRichmondVA 23284USA

Thick electrodes can substantially enhance the overall energy density of batteries.However,insufficient wettability of aqueous electrolytes toward electrodes with conventional hydrophobic binders severely limits utilization of active materials with increasing the thickness of electrodes for aqueous batteries,resulting in battery performance deterioration with a reduced capacity.Here,we demonstrate that controlling the hydrophilicity of the thicker electrodes is critical to enhancing the overall energy density of batteries.Hydrophilic binders are synthesized via a simple sulfonation process of conventional polyvinylidene fluoride binders,considering physicochemical properties such as mechanical properties and adhesion.The introduction of abundant sulfonate groups of binders(i)allows fast and sufficient electrolyte wetting,and(ii)improves ionic conduction in thick electrodes,enabling a significant increase in reversible capacities under various current densities.Further,the sulfonated binder effectively inhibits the dissolution of cathode materials in reactive aqueous electrolytes.Overall,our findings significantly enhance the energy density and contribute to the development of practical zinc-ion batteries.

关键词： Thick electrodes Hydrophilic binder sulfonation Aqueous zinc-ion batteries High areal capacity

Enhanced hydrolytic removal of tylosin in wastewater using polymer-based solid acid catalysts converted from polystyrene

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Journal of Environmental Sciences 2023年第4期126卷 287-296页

作者： Shiling Li Shuhan Sun Fei Qi Xiaomin Dou Beijing Key Lab for Source Control Technology of Water Pollution College of Environmental Science and EngineeringBeijing Forestry UniversityBeijing 100083China Engineering Research Center for Water Pollution Source Control and Eco-remediation College of Environmental Science and EngineeringBeijing Forestry UniversityBeijing 100083China

Antibiotic production wastewater usually contains high concentrations of antibiotic residues,which can cause instability and deterioration of biological wastewater treatment units and also domestication and proliferation of antibiotic-resistance bacteria.An effective pretreatment on antibiotics production wastewater is expected to selectively reduce the concentration of antibiotics and decrease the toxicity,rather than mitigate organic and other contaminants before further treatments.In this work,two polymer-based solid acids,PS-S and CPS-S bearing high concentrations of-SOH_(3)groups (up to 4.57 mmol/g),were prepared and successfully used for hydrolytic mitigation of 100 mg/L tylosin within 20 min.The co-existence of high concentrations of COD and humic substances did not affect the mitigation of tylosin obviously,while more than 500 mg/L of nitrogenous compounds suppressed the hydrolytic efficiency.Recycle and reuse experiments showed that the solid acids performed well in five cycles after regeneration.Three transformation products (P1,P2 and P3)were identified using UPLC-QTOF-MS/MS.Sugar moieties including mycarse,mycaminose,and mycinose detached and released simultaneously or in order from the 16-member lactone ring through desugarization,which led to a dramatic decrease in antibacterial activity as revealed by cytotoxicity evaluations using S.aureus.Ecotoxicity estimation indicated the acute toxicities of the hydrolyzed products to model species (e.g.,fish,daphnid and green algae) were classified as“not harmful”.This work suggested an effective and selective method to pretreat tylosin-contained production wastewater by using polymer-based solid acids.These results will shed light on effective elimination of antibiotics pollution from pharmaceutical industries through strengthening the pretreatments.

关键词： Polymer sulfonation Solid acid catalysts Tylosin hydrolysis Antibiotic

A sulfonated modification of PEEK for ultralow friction

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Friction 2023年第6期11卷 881-893页

作者： Shihua YUAN Chenhui ZHANG State Key Laboratory of Tribology Tsinghua UniversityBeijing100084China

Polyether ether ketone(PEEK)is a widely used material for friction pairs due to its excellent mechanical strength,good wear resistance,and chemical inertness.However,some modifications are necessary when PEEK is used as a water-lubricated friction pair.In this study,a novel sulfonation method was developed to design a water-lubricated friction pair with ultralow friction,good wear resistance,and high loading capacity.PEEK powders were sulfonated using ClSO3H and sintered to form bulk plastic.The sulfonated PEEK(SPEEK)plastic exhibited good tribological properties.At a low sliding speed,the friction coefficient was smaller than 0.02 when a 3 wt% NaCl solution was used as the lubricant.The order of magnitude of the wear rate was as low as 10^(-8) mm^(3)/(N·m).The mechanism of friction reduction was mainly hydration lubrication.The negatively charged -SO_(3)^(-) groups on the friction pair can adsorb hydrated Na+cations by electrostatic interactions.These hydrated Na+cations have a high load capacity and low shearing resistance.The ultralow wear mechanism observed in this study is possibly due to ultralow friction properties of the friction pairs prepared through the proposed sulfonation and thermoforming procedures.

关键词： polyether ether ketone(PEEK) sulfonation hydration lubrication friction wear

Synthesis,optimization and characterization of biochar based catalyst from sawdust for simultaneous esterification and transesterification

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Chinese Journal of Chemical Engineering 2018年第12期26卷 2654-2663页

作者： Suchith Chellappan Vaishakh Nair Sajith V. Aparna K. Department of Chemical Engineering National Institute of TechnologyCalicut India Institute of Physical Chemistry Polish Academy of Sciences School of Nano Science and Technology National Institute of Technology

The development of a benign environmental catalyst for the generation of biodiesel is an area of importance to reduce the overall usage of fossil fuels. In the current work, biochar was produced by slow pyrolysis of Irul wood sawdust. The optimization for biochar generation was carried out for different reaction temperatures and heating durations. The biochar was used to prepare solid acid catalysts by sulfonation process. The characterization of biochar and the sulfonated catalyst were carried out using Elemental analysis, Fourier Transform Infrared spectroscopy(FTIR), Powder X-ray Diffraction(XRD), Thermo Gravimetric Analysis(TGA), Scanning Electron Microscopy(SEM) and Surface area analyzer(BET). The characterization results showed that sulfonation of biochar resulted in biochar based solid acid catalyst containing various functional acidic groups like weak acidic\\OH groups, strong acidic\\COOH and SO3 H groups. The total acid density and sulfonic acid group density of catalyst were estimated and showed excellent acidic sites concentration which gives a good catalytic activity for biodiesel production through simultaneous esterification and transesterification. The enhanced catalytic activity is due to the high acid density of SO3 H groups and the reactant accessibility towards acidic sites as well as the strong affinity between the hydrophilic reactants and the neutral OH groups which are bonded with the polycyclic aromatic carbon rings. The performance of biochar catalyst for the production of biodiesel was evaluated by comparing the yield obtained. The FTIR and Gas Chromatography–Mass Spectroscopy(GC–MS) were also carried out for the analysis of biodiesel produced.

关键词： Biochar Biochar based catalyst Pyrolysis Biomass sulfonation