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Mechanism of Preparation of Platform Compounds from Lignocellulosic biomass Liquefaction Catalyzed by Bronsted Acid: A Review

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Journal of Bioresources and Bioproducts 2019年第4期4卷 202-213页

作者： Kang GUO Qiyuan GUAN Junming XU Weihong TAN Institute of Chemical Industry of Forest Products Chinese Academy of ForestryNational Engineering Lab for Biomass Chemical UtilizationKey and Open Lab of Forest Chemical EngineeringState Forestry AdministrationKey Lab of Biomass Energy and MaterialJiangsu ProvinceNanjing 210042China

Over the past two decades, research on transforming lignocellulosic biomass into small molecule chemicals byusing catalytic liquefaction has made great progress. Notably, in recent years it has been found the production of smallmolecule chemicals through directional liquefaction of lignocellulosic biomass. Understanding the liquefactionmechanism of lignocellulosic biomass is highly important. In this review, the liquefaction mechanism of lignocellulosicbiomass and model compounds of cellulose are described, and some problems and suggestions to address them aredescribed.

关键词： lignocellulosic biomass liquefaction product platform chemical bronsted acid liquefaction mechanism

Facile Synthesis and Crystal Structure of a Novel Cyanopyridine

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Chinese Journal of Structural Chemistry 2011年第7期30卷 1011-1015页

作者：杨晓慧刘承果周永红崔竞方林小羽 Institute of Chemical Industry of Forestry Products CAF National Engineering lab.for biomass Chemical Utilization key and lab.on Forest Chemical Engineering SFA key lab.of biomass energy and material

The title compound 2-amino-4-（4-hydroxy-3,5-dimethoxyphenyl）-5-methyl-6- phenyl nicotinonitrile, C21H19N3O3, was synthesized via four-component reactions between propiophenone, malononitrile, syringaldehyde and ammonium acetate in ethanol under reflux without catalyst and characterized by IR, 1H NMR, 13C NMR, MS, EA and single-crystal X-ray diffraction. Single-crystal X-ray diffraction analysis shows that the compound is of monoclinic system, space group P21/n with a = 8.4600（17）, b = 17.139（3）, c = 13.408（3） A, β= 107.06（3）°, V= 1858.6（6） A3, Z = 4, Mr = 361.39, F（000） = 760, μ（MoKa） = 0.088 mm^-1 Dc = 1.292 g/cm3, 2 = 0.71073 A, the final R = 0.0751 and wR = 0.0938 for 3333 observed reflections with I〉 2σ（I）. The crystal packing of the title compound is stabilized by intermolecular hydrogen bonds.

关键词： cyanopyridine synthesis crystal structure multi-component reactions

Two Dehydroabietic Acid-based Arylamines: Synthesis, Crystal Structure and Fluorescent Properties

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Chinese Journal of Structural Chemistry 2013年第3期32卷 396-402页

作者：高宏宋杰商士斌宋湛谦 Institute of Chemical Industry of Forestry Products CAF National Engineering lab. for biomass Chemical Utilization key and lab.on Forest Chemical Engineering SFAKey Lab. of Biomass Energy and Material Department of Chemistry and Biochemistry University of Michigan-Flint

Two dehydroabietic acid-based arylamines have been synthesized and characterized by FTIR, 1H NMR, 13C NMR, MS spectra and elemental analysis. Their spatial structures were determined by X-ray diffraction analysis. UV-Vis absorption and fluorescence spectral characteristics of these compounds in methanol were investigated. Their fluorescence emission spectra in different polarity solvents were further evaluated. Fluorescent properties and structural relationship of the compounds showed that fluorescence intensity and quantum yield inversely increase with the non-coplanar degree. In addition, the solvent polarity has different effects on the fluorescence emission spectra of two compounds.

关键词： dehydroabietic acid-based arylamine synthesis crystal structure fluorescent property

A process insight into production of ethyl levulinate via a stepwise fractionation

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Journal of Bioresources and Bioproducts 2024年第2期9卷 233-242页

作者： Yan Ma Hongxiao Wang Ziyang Wu Weihong Tan Guodong Feng Jianchun Jiang Institute of Chemical Industry of Forest Products Chinese Academy of ForestryNanjing 210042China Jiangsu Province key lab.of biomass energy and material Nanjing 210042China National Engineering lab.for biomass Chemical Utilization Nanjing 210042China Co-Innovation Center of Efficient Processing and Utilization of Forest Resources Nanjing Forestry UniversityNanjing 210037China

Ethyl levulinate(EL)is a key biomass-derived compounds due to its socio-economic benefits for the synthesis of commodity chemicals.Herein,we proposed an efficient one-step bamboo conversion to EL in ethanol,and a novel stepwise fractionation to purify EL and lignocellulose degradation products.A proton acid,due to its high catalytic efficiency,yielded 26.65%EL in 120 min at 200℃.The productions of ethyl glucoside and 5-ethoxymethylfurfural were analyzed in terms of by-products formation.To the best of our knowledge,there is no single report on catalyst for one step synthesis of EL directly from bamboo,as well as a stepwise fractionation to purify EL.Due to similar physiochemical properties in each fraction,the platform molecules could broaden a new paradigm of bamboo biomass utilization for renewable energy and value-added biochemicals.In addition,glucose,ethyl glucoside,corn starch,and microcrystalline cellulose were also investigated as substrates,so that the reaction intermediates of this one-pot procedure were identified and a possible reaction mechanism was proposed.

关键词： Ethyl levulinate Liquefaction biomass Ethanol By-products

Synthesis and Application of UV-curable Phosphorous-Containing Acrylated Epoxidized Soybean Oil-based Resins

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Journal of Bioresources and Bioproducts 2019年第3期4卷 49-57页

作者： Yun HU Puyou JIA Qianqian SHANG Meng ZHANG Guodong FENG Chengguo LIU Yonghong ZHOU Institute of Chemical Industry of Forest Products Chinese Academy of ForestryKey Lab of Biomass Energy and MaterialJiangsu ProvinceNational Engineering Lab for Biomass Chemical UtilizationKey Lab on Forest Chemical EngineeringState Forestry AdministrationNanjing 210042China Co-Innovationof Efficient Processing and Utilization of Forest Resources Nanjing Forestry UniversityNanjing 210037China

A novel phosphorous-containing acrylated epoxidized soybean oil-based(P-AESO)resin was developed via the ring-opening reaction of epoxidized soybean oil(ESO)with diphenylphosphinic chloride(DPPC),followed by acrylation of the resulting groups.The chemical structure was characterized by Fourier transform infrared spectroscopy(FT-IR),and ^(1)H nuclear magnetic resonance(^(1)H NMR).Subsequently,the viscosity and volumetric shrinkage of the obtained P-AESO resins were studied.Then the oligomer was formulated into UV-curable coatings,and the mechanical,thermal,and coating properties of the resulting UV-cured bioresins were studied by tensile testing,dynamic mechanical thermal analysis(DMA),thermogravimetric analysis(TGA)coupled with FT-IR spectroscopy(TGA-FT-IR),hardness,adhesion,pencil hardness and chemical resistance.Furthermore,the UV-curing behavior of the P-AESO resin was determined by real-time realtime infrared(RT-IR).Meanwhile,compared with coating from acrylated epoxidized soybean oil(AESO),the P-AESO system coatings showed better volumetric shrinkage,excellent adhesion,and enhanced thermal and glass transition temperature(Tg)while maintaining reasonably final C=C conversions and cross-link density.For instance,the obtained P-AESO/trimethylolpropanetriacrylate(TMPTA)20 material possessed a volumetric shrinkage of 4.1%,Tg of 115.6℃,char yield of 9.47%,and final C=C conversions of 81.4%respectively,which exhibited superior values than that of the AESO/TMPTA20 material.The improvement of the P-AESO coating performances could contribute to the architectures that combined the structural features of phosphorous-containing rigid benzene.The developed P-AESO resin is promising for applications in the UV-curable coatings.

关键词： biobased UV-curable coatings acrylated epoxidized soybean oil diphenylphosphinic chloride

Metallurgical pyrolysis toward Co@Nitrogen-doped carbon composite for lithium storage

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Green energy & Environment 2021年第1期6卷 91-101页

作者： Yanyan Liu Kang Sun Jianchun Jiang Wenshu Zhou Yuan Shang Chenxia Du Baojun Li b Institute of Chemical Industry of Forest Products CAFNational Engineering Lab.for Biomass Chemical UtilizationKey Lab.of Chemical Engineering of Forest ProductsNational Forestry and Grassland AdministrationKey Lab.of Biomass Energy and MaterialJiangsu ProvinceCo-Innovation Center of Efficient Processing and Utilization of Forest ResourcesNanjing210042China College of Chemistry Zhengzhou UniversityZhengzhou450001China Supercomputer Center in ZZU Zhengzhou UniversityZhengzhou450052China

Elemental state matter-heteroatom-doped carbon composites are of great importance for the development of anode in lithium ion batteries(LIBs).In this article,metal–organic frameworks(MOFs)are adopted as precursor to prepare Co composites via metallurgical pyrolysis under controllable conditions.The obtained nitrogen-doped porous carbon-Co nanocomposite possesses core–shell structure(Co@C–N).Co@C–N exhibits the best Li storage performances as anode active matter.After the 200th cycles at current density of 0.2 A g^(-1),a reversible capacity of 870 mAh g^(-1)is retained.A reversible capacity of 275 mAh g^(-1)still maintains with 5 A g^(-1).Co@C–N presents a high reversible capacity with excellent cycle stability.Considering the corresponding experimental and theoretical results,the Co0-based N-doped porous carbon composite is proposed to work as LIBs anode matter.These results provide a new design idea for electrode matters of metallic ion battery,and demonstrate that MOFs pyrolysis is an effective method for the construction of elemental state anode materials.

关键词： Co nanoparticles(NPs) Core–shell structure Lithium ion battery anode Metal–organic framework(MOF) Nitrogen-doped carbon

Oxygen-vacancy-rich MnOx supported RuOx for efficient base-free oxidation of 5-hydroxymethylfurfural and 5-methoxymethylfurfural to 2,5-furandicarboxylic acid

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Journal of energy Chemistry 2024年第8期95卷 670-683页

作者： Jiali Wu Weizhen Xie Yining Zhang Xixian Ke Tianyuan Li Huayu Fang Yong Sun Xianhai Zeng Lu Lin Xing Tang Xiamen key laboratory of Clean and High-valued Applications for biomass Fujian Engineering and Research Center of Clean and High-valued Technologies for Biomass College of Energy Xiamen University key lab for Sport Shoes Upper materials of Fujian Province Fujian Engineering and Research Center for New Functional Fiber Materials(Fujian Huafeng New Material Co.Ltd.Putian Dakai New Material Co. Ltd.)

2,5-Furandicarboxylic acid(FDCA) is a promising biomass-derived polymeric monomer that serves as an attractive alternative to terephthalic acid derived from fossil resources. However, the green and efficient production of FDCA through the oxidation of 5-hydroxymethylfurfural(HMF) and its derivatives is still rudimentary under base-free conditions. In this work, oxygen-vacancy-rich Mn Oxwas prepared and displayed a strong adsorption and anchoring ability to Ru species that mainly exposed the(2 1 0) plane of RuO2, bringing about highly dispersed and active interfacial Ru-O-Mn structures. Experimental results and density functional theory calculations confirm that these above features greatly facilitate the adsorption/activation of oxygen and the dehydrogenation-oxidation of HMF/5-methoxymethylfurfural(MMF),which enables an efficient FDCA production under base-free and mild conditions. Notably, a desirable FDCA yield of 86.56% was still obtained from concentrated HMF(10 wt%) under base-free conditions over oxygen-vacancy-rich Mn Oxsupported Ru Ox(1.0 MPaO2, 120 °C, 6 h). This work delineates a facile catalyst preparation strategy for HMF/MMF oxidation, and might open a new avenue for the green synthesis of FDCA under base-free conditions.

关键词： 2,5-Furandicarboxylic acid 5-Hydroxymethylfurfural 5-Methoxymethylfurfural Base-free oxidation Oxygen-vacancy-rich

Analysis and comparison of tribological performance of fatty acid-based lubricant additives with phosphorus and sulfur

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Journal of Bioresources and Bioproducts 2020年第2期5卷 134-142页

作者： Haiyang Ding Xiaohua Yang Lina Xu Mei Li Shouhai Li Sujing Zhang Jianling Xia key lab.of biomass energy and material Nanjing 210042China Co-Innovation Center of Efficient Processing and Utilization of Forest Resources Nanjing 210042China key lab.of Chemical Engineering of Forest Products National Forestry and Grassland AdministrationNanjing 210042China National Engineering lab.for biomass Chemical Utilization Nanjing 210042China anjing Science and Technology Development Corporation Nanjing 210042China

Two environmentally friendly,water-based lubricant additives(phosphorus-containing ricinoleic acid(PRA)and sulfur-containing ricinoleic acid(SRA))were prepared.The lubrication perfor-mance of the additives in a water-based lubricant was tested using a four-ball tribotester.The stainless steel surface was analyzed by using scanning electron microscopy(SEM)and X-ray pho-toelectron spectroscopy(XPS).The additives reduced the coefficient of friction(COF)value,wear scar diameter(WSD)and improved the extreme pressure(PB)value.Water-based fluids con-taining the PRA exhibited lower COF,WSD,and PB values than the SRA.The good tribological performances of the PRA and SRA were attributed to the synergistic action of long aliphatic chains and highly active phosphorus and sulfur elements.

关键词： Ricinoleic acid Water-soluble additive Tribological performance Friction mechanism

Base-free oxidative esterification of 5-hydroxymethylfurfural to furan-2,5-dimethylcarboxylate over n-doped carbon-supported Co/Fe bimetallic catalyst under batch-operation or continuous-flow conditions

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Journal of energy Chemistry 2022年第12期75卷 95-108,I0004页

作者： Weizhen Xie Binglin Chen Wenlong Jia Huai Liu Zheng Li Shuliang Yang Xing Tang Xianhai Zeng Yong Sun Xixian Ke Tianyuan Li Huayu Fang Lu Lin Xiamen key laboratory of Clean and High-valued Applications for biomass Fujian Engineering and Research Center of Clean and High-valued Technologies for BiomassCollege of EnergyXiamen UniversityXiamen 361102FujianChina biomassChem Group Faculty of Chemical EngineeringKunming University of Science and TechnologyKunming 650500YunnanChina key lab for Sport Shoes Upper materials of Fujian Province Fujian Engineering and Research Center for New Functional Fiber Materials(Fujian Huafeng New Material Co.Ltd.Putian Dakai New Material Co.Ltd.)Putian 351144FujianChina

Developing an efficient and easily available catalyst for the selective conversion of biomass-derived 5-hydroxymethylfurfural(HMF)into furan-2,5-dimethylcarboxylate(FDMC),a valuable biomass-based monomer,remains a high demand but formidable challenge.Herein,a facile strategy for the synthesis of N-doped carbon-supported Co/Fe bimetallic catalyst(CoFe-NC)was developed,which provided an outstanding FDMC yield of 93%in a batch reactor(base-free,80℃,2 bar O_(2),4 h).Interestingly,CoFe-NC also gave a high FDMC yield of 91%under continuous-flow conditions for 80 h(5 bar O_(2),80℃,GHSV 1320 h^(-1),LHSV 0.6 h^(-1),base-free).Notably,it is the first time that a non-noble catalyst gave such a high FDMC yield under continuous-flow conditions.The introduction of Fe could greatly improve both the electron intensity of Co-N_(x)species and basicity of the catalyst,which endowed CoFe-NC with improved O_(2)activation capacity and enhanced dehydrogenation activity for the oxidation-esterification of HMF.This work delineates the efficient strategy on the construction of N-doped carbon-supported non-noble catalyst,which might open a new avenue for developing highly efficient catalyst for FDMC production.

关键词： 5-Hydroxymethylfurfural Furan-2,5-dimethylcarboxylate Oxidation-esterification Catalysis Co-N_(x)sites