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Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent

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Chinese Journal of Chemical Engineering 2023年第2期54卷 248-256页

作者： Yinglin Mai Xiaoling Xian Lei Hu Xiaodong Zhang Xiaojie Zheng Shunhui Tao Xiaoqing Lin School of Chemical Engineering and Light Industry Guangdong University of TechnologyGuangzhou 510006China Guangdong Provincial Key Laboratory of Plant Resources Biorefinery Guangdong University of TechnologyGuangzhou 510006China Guangzhou Key Laboratory of Clean Transportation Energy Chemistry Guangdong University of TechnologyGuangzhou 510006China

levulinic acid(LA)is one of the top-12 most promising biomass-based platform chemicals,which has a wide range of applications in a variety of fields.However,separation and purification of LA from aqueous solution or actual hydrolysate continues to be a challenge.Among various downstream separation technologies,liquid-liquid extraction is a low-cost,effective,and simple process to separate LA.The key breakthrough lies in the development of extractants with high extraction efficiency,good hydrophobicity,and low cost.In this work,three hydrophobic deep eutectic solvents(DESs)based on tri-n-octylamine(TOA)as hydrogen bond acceptor(HBA)and alcohols(butanol,2-octanol,and menthol)as hydrogen bond donors(HBDs)were developed to extract LA from aqueous solution.The molar ratios of HBD and HBA,extraction temperature,contact time,solution pH,and initial LA concentration,DES/water volume ratios were systematically investigated.Compared with 2-octanol-TOA and menthol-TOA DES,the butanol-TOA DES exhibited the superior extraction performance for LA,with a maximum extraction efficiency of 95.79±1.4%.Moreover,the solution pH had a great impact on the LA extraction efficiency of butanol-TOA(molar ratio=3:1).It is worth noting that the extraction equilibrium time was less than 0.5 h.More importantly,the butanol-TOA(3:1)DES possesses good extraction abilities for low,medium,and high concentrations of LA.

关键词： Extraction Separation levulinic acid Deep eutectic solvents Hydrophobic Aqueous solution

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Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles

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Green Energy & Environment 2023年第2期8卷 438-443页

作者： Cailing Wu Mengjie Lou Mingming Sun Huiyong Wang Zhiyong Li Jikuan Qiu Jianji Wang Zhimin Liu Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical EngineeringKey Laboratory of Green Chemical Media and ReactionsMinistry of EducationHenan Normal UniversityXinxiangHenan453000China Beijing National Laboratory for Molecular Sciences Key Laboratory of ColloidInterface and ThermodynamicsCAS ResearchInstitute of ChemistryChinese Academy of SciencesBeijing100190China

Synthesizing nitrogen(N)-containing molecules from biomass derivatives is a new strategy for production of this kind of chemicals.Herein,for the first time we present the synthesis of N-substituted aryl pyrroles via reductive amination/cyclization of levulinic acid(LA)with primary aromatic amines and hydrosilanes(e.g.,PMHS)over Cs F,and a series of N-substituted aryl pyrroles could be obtained in good to excellent yields at 120○C.The mechanism investigation indicates that the reaction proceeds in two steps:the cyclization between amine and LA occurs first to form intermediate 5-methyl-N-alkyl-1,3-dihydro-2H-pyrrolones and their isomeride(B),and then the chemo-and region-selective reduction of intermediates take place to produce the final products.This approach for synthesis of N-substituted aryl pyrroles can be performed under mild and green conditions,which may have promising applications.

关键词： Biomass levulinic acid Reductive amination Pyrrole

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Comparative study of microwave-assisted versus conventional heated reactions of biomass conversion into levulinic acid over hierarchical Mn_(3)O_(4)/ZSM-5 zeolite catalysts

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Carbon Resources Conversion 2023年第3期6卷 245-252页

作者： Mazizah R.A.Helmi Dyah Utami C.Rahayu Arnia P.Pratama Irena Khatrin Anita N.Ramadhani Yuni K.Krisnandi Department of Chemistry Faculty of Mathematics and Natural ScienceUniversitas IndonesiaDepok 16424Indonesia Solid Inorganic Framework Laboratory Department of ChemistryFaculty of Mathematics and Natural ScienceUniversitas IndonesiaDepok 16424Indonesia

Conversion of delignified cellulose from rice husk biomass,and model compounds of cellobiose and glucose to levulinic acid(LA)over hierarchical Mn_(3)O_(4)/ZSM-5 catalyst was carried out using a household microwave method,and then compared to the established conventional thermos-reaction method.The hierarchical ZSM-5 was prepared using a double template method,aiming for micro and mesoporous systems developed in the structure.The as-prepared ZSM-5 were modified with Mn3O4 through incipient wetness impregnation with Mn2+solution followed by calcination at 550℃.The catalysts were characterized using various techniques such as powder XRD,SEM,BET,AAS,and FT-IR which indicated the hierarchical structure of MFI zeolite(Si/Al of 30-34)with Mn loading of 2.14 wt%.The conversion products were analyzed using HPLC,1H NMR,and 13C NMR instruments.The microwave-assisted reaction using 600 W for 180 s using delignified cellulose,cellobiose,and glucose gave conversion of 37.27%,46.35%,and 54.29%,respectively which is close to the conversion given by the conventional reaction carried out at 130◦C for 4 h(36.75%,55.62%,and 60.9%,respectively).Interestingly,the LA yield from the microwave-assisted reaction(4.33%,6.12%,and 9.57%)is higher than the yield from the conventional reaction,which only produced 5.2%,4.88%,and 6.93%respectively.The microwaveassisted method is also shown to give less by-products compared to the thermochemical reaction.Therefore,it could be considered an alternative method for converting cellulose to LA.

关键词： Hierarchical ZSM-5 zeolite levulinic acid Lignocellulose conversion Microwave-assisted synthesis Cellobiose Glucose

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Hydrogen production from steam reforming of biomass-derived levulinic acid over highly stable spinel-supported Ni catalysts

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Waste Disposal and Sustainable Energy 2023年第4期5卷 427-438页

作者： Tian Li Hongcai Su Lingjun Zhu Dan Xu Na Ji Shurong Wang State Key Laboratory of Clean Energy Utilization Zhejiang UniversityZheda Road 38Hangzhou310027China School of Environmental Science and Engineering Tianjin Key Laboratory of Biomass/Wastes UtilizationTianjin UniversityTianjin300350China

As one of the main oxygen-containing organic products generated from the hydrothermal conversion of biomass,levulinic acid(LA)has the potential to be further upgraded.This work investigated the steam reforming(SR)process of biomass-derived LA to produce H_(2).A series of Ni catalysts supported by various spinels were synthesized via co-precipitation and impregnation.The Ni active metal dispersed well on the NiAl_(2)O_(4)catalyst with high specific surface area,thereby exhibiting high catalytic activity.Among all the catalysts tested,15Ni/NiAl_(2)O_(4)showed the best performance for SR of LA,resulting in high carbon conversion of 96.3%,H_(2)yield of 92.8%,and H_(2)concentration of 67.9%at a reaction temperature of 800℃.Additionally,the influences of reaction temperature,steam-to-carbon ratio(S/C),and liquid hourly space velocity(LHSV)were also examined.Moreover,during the 40-h continuous SR process of LA,the 15Ni/NiAl_(2)O_(4)catalyst maintained its outstanding catalytic activity.This study provides an encouraging route for upgrading biomass-derived LA into eco-friendly and high-value fuels,thereby advancing the sustainability of the biomass refining process.

关键词： Biomass levulinic acid Hydrogen Spinel-supported Ni catalysts Steam reforming

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Promotional effect of Mn doping on Ru/layered MCM-49 catalysts for the conversion of levulinic acid to γ-Valerolactone

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Carbon Resources Conversion 2022年第3期5卷 185-192页

作者： Wenlin Li Feng Li Xin Ning Kaixi Deng Junwen Chen Jiajun Zheng Ruifeng Li College of Chemical Engineering and Technology Taiyuan University of TechnologyTaiyuanShanxi 030024China Chemistry Department State University of New YorkStony BrookNewYork 11794USA Research Institute of Petroleum Processing SinopecBeijing 100083China

Selective hydrogenation of levulinic acid(LA)toγ-Valerolactone(GVL)is an important reaction to produce high value-added chemicals and fuels but remains a big challenge.Herein we reported a Ru/zeolite catalyst with Mn promotion,which exhibited excellent catalytic performance(yield:98%)towards LA to GVL.The intrinsic activity(TOF)also increased obviously with the Mn addition.The particle size of Ru gradually decreased with the increase of Mn loading and a strong interaction between Ru and support was observed for the Ru-Mn/MCM-49 catalyst.The addition of Mn not only offered a good dispersion of Ru species on MCM-49,but also increased the L/B ratio of the catalyst,thereby contributing to the high GVL selectivity.High dispersed Ru sites were the intrinsic active sites of the catalyst verified by the in-situ experimental studies.The dissociation of the reactants was significantly enhanced,resulting in higher catalytic activity.

关键词： levulinic acid γ-Valerolactone Zeolites Ru-catalyst Mn promotion

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Role of the Cu-ZrO_(2) interface in the hydrogenation of levulinic acid to γ-valerolactone

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Journal of Energy Chemistry 2021年第10期30卷 446-458,I0012页

作者： Ziyi Li Haigang Hao Jingjing Lu Chengming Wu Rui Gao Jifan Li Chun-Ling Liu Wen-Sheng Dong Key Laboratory of Applied Surface and Colloid Chemistry(SNNU) MOESchool of Chemistry and Chemical EngineeringShaanxi Normal UniversityXi’an 710062ShaanxiChina College of Chemistry and Chemical Engineering Inner Mongolia UniversityHohhot 010021Inner MongoliaChina

Here we exquisitely fabricated Cu/ZrO_(2)-dp catalysts with plentiful Cu-ZrO_(2)interfaces by depositing amorphous ZrO_(2)onto Cu nanoparticles for the hydrogenation of levulinic acid(LA)to y-valerolactone(GVL).With the created plentiful CU-ZrO_(2)interfaces,the optimal catalyst 3 Cu/ZrO_(2)-dp exhibited exceptional catalytic performance under mild reaction conditions,and achieved the highest GVL mass productivity of 266.0 mmol GVL·h^(-1)·g^(-1)Cu,which was 12.5 and 2.3 times of CU/ZrO_(2)catalysts with equivalent Cu loadings prepared by traditional impregnation(3 Cu/ZrO_(2)-im)or co-precipitation(3 Cu/ZrO_(2)-cp).As far as we know,this GVL mass productivity stood at the highest level compared with those obtained using non-noble metal catalysts under similar reaction conditions.By systematic investigation with multiple characterizations,density functional theory(DFT)calculations,and kinetic studies,it was found that interfacial active centers were created at Cu-ZrO_(2)interfaces,which contained oxygen vacancies(O_(v)),negatively charged Cu^(δ)-and partially reduced Zr^(3+)The O_(v) favored the adsorption and activation of LA via its ketone group,while negatively charged Cu^(δ)-was able to enhance heterolysis of H2,which resulted in the formation of H^(+)-Cu^(δ)-and Zr^(3+)-H^(-)active species via hydrogen spillover.Also,plentiful acid sites,which derived from coordinatively unsaturated and defective Zr species,generated at Cu-ZrO_(2)interfaces.With the cooperation of interfacial active centers(Cu^(δ-)-O_(v)-Zr^(3+))and acid sites,the fabricated 3 Cu/ZrO_(2)-dp with plentiful Cu-ZrO_(2)interfaces achieved excellent catalytic performance for the hydrogenation of LA to GVL.Hence,the synergistic catalysis of Cu-ZrO_(2)interfaces provided an effective strategy for designing catalysts with a satisfactory performance for the hydrogenation of LA,which also can be expanded to other hydrodeoxygenation reactions.

关键词： Cu-ZrO_(2)interface γ-Valerolactone levulinic acid Oxygen vacancy Hydrodeoxygenation

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Aqueous-phase hydrogenation of levulinic acid over carbon layer protected silica-supported cobalt-ruthenium catalysts

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Chinese Journal of Chemical Engineering 2021年第10期34卷 114-122页

作者： Lihua Qian Guojun Lan Xiaoyan Liu Zhenqing Li Ying Li Institute of Industrial Catalysis Zhejiang University of TechnologyHangzhou 310014China

The hydrogenation of levulinic acid(LA)to c-valerolactone(GVL)by using water as solvent is a crucial process in the production of fine chemicals from biomass.An ultrathin carbon layer coating CoRu bimetallic catalyst supported on silica(CoRu@C/SiO2)is prepared by using tannis-ligated cobalt-ruthenium complex on silica as precursors,and applied for catalyzed synthesis of GVL from LA.Because of the synergistic effect between cobalt and ruthenium,the addition of small amounts of Ru to Co catalysts can increase the catalytic activity in the aqueous hydrogenation of LA.The ultrathin carbon layer covered on the CoRu bimetallic catalyst can greatly reduce the leaching of active metals.The CoRu@C/SiO2 catalyst achieves high stability and is reused up to 5 runs without significant loss of performance in aqueous hydrogenation of levulinic acid.

关键词： levulinic acid Hydrogenation Cobalt-ruthenium Synergistic effect Carbon coating

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Co encapsulated N-doped carbon nanotubes as robust catalyst for valorization of levulinic acid in aqueous media

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Journal of Energy Chemistry 2021年第1期30卷 12-19,I0001页

作者： Xiangjin Kong Weijie Geng Wenxiu Li Lin Liu Xiaoqi Yan Longchen Gong Junhai Liu School of Chemistry and Chemical Engineering Shandong Provincial Key Laboratory/Collaborative Innovation Center of Chemical Energy Storage&Novel Cell TechnologyLiaocheng UniversityLiaocheng 252000ShandongChina

The construction of an acid resistant catalyst for synthesis of γ-valerolactone from levulinic acid in aqueous media is an important but highly challenging goal.Herein,an efficient Co@NCNT-800(after 800℃ pyrolysis) catalyst was constructed by confining Co in N-doped carbon nano-tubes(NCNT) from low cost materials by a facile strategy.Combined with the characterization results and control experiments,the in situ formed Co and Co-Ox, but not Co-Nx, proved to be the main synergistic active sites of the catalyst.It was also found that Co species are completely isolated within the bamboo-like NCNT,which could protect the metal nanoparticles from agglomeration and leaching in the strong acid reaction system.The γ-valerolactone yield of no less than 99.9% can be obtained under a relatively mild condition,and the catalytic performance has not been significantly reduced within five cycles.Therefore,this work may pave a way for the design of robust non-noble catalyst,and has potential for the production of γ-valerolactone from biomass in large-scale industries.

关键词： levulinic acid γ-Valerolactone Co@N-doped carbon nanotubes Aqueous phase reaction

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Preliminary Optimization and Kinetics of SnCl_(2)-HCl Catalyzed Hydrothermal Conversion of Microcrystalline Cellulose to levulinic acid

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Journal of Renewable Materials 2021年第1期9卷 145-162页

作者： Dexby de Guzman Rizalinda de Leon Fuels Energy and Thermal Systems LaboratoryDepartment of Chemical EngineeringUniversity of the PhilippinesQuezon City1101Philippines

levulinic acid(LA)is a platform biorefinery chemical from biomass which can be converted to green solvents,plasticizers,polymer precursors,biobased cleaning agents,fuels and fuel additives.This study assessed the potential of SnCl_(2)-based mixed acid systems as catalyst in the hydrothermal conversion of microcrystalline cellulose to levulinic acid.Maximum LAyield of 36.2 mol%was achieved using 0.2 M SnCl_(2) concentration at test conditions of 3 h,180℃ and 1%w/v cellulose loading.To reduce precipitate formation and further improve LA yield,the strategy employed was to combine SnCl_(2)(a Lewis acid)with conventional mineral acids(Bronsted acids).Evaluation of the catalytic performance of SnCl_(2)-HCl,SnCl_(2)-H_(2)SO_(4),SnCl_(2)-HNO_(3),and SnCl_(2)-H_(3)PO_(4)(1:1 molar ratio,0.2 M total acid concentration)were done with highest LA yield of 47.0 mol%obtained using the SnCl_(2)-HCl system at same test conditions.Response surface methodology optimization employing Box-Behnken design generated a quadratic model with a high coefficient of determination(r2)of 0.964.A maximum LA yield of 63.5 mol%can be achieved at 0.17 M catalyst concentration,198℃,and 5.15 h reaction time.Rate constants were estimated using nonlinear regression,while activation energies were determined using Arrhenius equation.Cellulose hydrolysis was determined to be the rate-limiting step in the overall process.Low activation energy of 63.3 kJ/mol for glucose dehydration to hydroxymethylfurfural supports the action of SnCl_(2) as Lewis acid in the mixed-acid system.LA yield simulations for plug flow reactor(PFR)and continuous stirred tank reactor(CSTR)were done suggesting a similar PFR-CSTR configuration with the established Biofine process.Lastly,a reaction scheme was presented to explain the synergy between SnCl_(2) and HCl in LA production from cellulose.

关键词： levulinic acid tin(II)chloride cellulose optimization kinetics

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Iridium-Catalyzed Reductive Amination of levulinic acid to Pyrrolidinones under H2 in Water

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Chinese Journal of Chemistry 2017年第5期35卷 581-585页

作者： Zhanwei Xu Peifang Yan Hong Jiang Kairui Liu Z. Conrad Zhang Dalian National Lab for Clean Energy State Key Laboratory of Catalysis Dalian Institute of Chemical Physics Chinese Academy of Sciences Dalian Liaoning 116023 China

The synthesis of pyrrolidinones from reductive amination of levulinic acid （LA） with primary amines is reported.Pyrrolidinones have various applications such as surfactants,pharmaceutical intermediates,dispersants,and solvents.The half-sandwich Cp＊Ir complex （Cp＊ is 1,2,3,4,5-pentamethylcyclopenta-l,3-diene） coordinated by bipyridine ligand bearing both dimethylamino and ortho-hydroxyl groups showed high catalytic activity for the reductive amination of LA.A range of primary amines,such as aromatic and benzyl amines,were readily converted to corresponding pyrrolidinones in good yields.

关键词： iridium reductive amination hydrogenation levulinic acid biomass

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