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    28 April 2024, Volume 44 Issue 2 Previous Issue   
    Preparation and Properties of Hydrogenated Rosin Ester Bonded Silica Gel Column
    Lijuan JIANG, Huiying WU, Lei ZENG, Yuping SU, Fuhou LEI, Hao LI
    2024, 44 (2):  1-8.  doi: 10.3969/j.issn.0253-2417.2024.02.001
    Abstract ( 43 )   HTML ( 1449 )   PDF (816KB) ( 63 )   Save

    Hydrogenated rosin glycol acrylate(EGHRA) was bonded to the surface of thioglycolated silica gel(SH@SiO2) by click chemical reaction to prepare a novel hydrogenated rosin acrylate ethylene glycol ester bonded silica gel(EGHRA@SiO2) stationary phase. The synthesized stationary phase was characterized by elemental analysis, infrared spectroscopy, thermogravimetric analysis, N2 adsorption-desorption experiments, and particle size distribution tests. The results showed that the EGHRA@SiO2 stationary phase had an increased C content of 10.72 percentage points compared to SiO2, a specific surface area of 270.06 m2/g, an average pore diameter of 6.16 nm, and an average particle size of 10 μm. A 250 mm×30 mm preparation column was filled by homogenization method, and a series of chromatographic evaluations were performed, demonstrating good flowability typical reversed-phase chromatographic characteristic as well as excellent stability and reproducibility of the EGHRA@SiO2 preparation column. Tanaka tests showed that the spatial selectivity of EGHRA@SiO2 column was superior to that of C18 column owing to the phenanthrene-like skeleton of the bonding monomer. Under reversed-phase chromatographic mode, EGHRA@SiO2 preparation column exhibited ideal separation performance for the crude extracts of Taxus bark. Using the screened acetonitrile-water(volume ratio of 47∶53) mobile phase at a flow rate of 15 mL/min, the purity of paclitaxel(PTX), 10-deacetylbaccatin III(10-DAT), 7-xylosyl-10-deacetylbaccatin III(7-xyl-10-DAT) and cephalomannine(CEP) in the crude extract were increased by 91.52, 83.24, 62.99 and 55.85 percentage points after a single purification step of 1.0 mL injection sample, respectively.

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    Synthesis and Antifungal Activity of (Z)-/(E)-Piperitone-based Pyrazole-oxime Ester Compounds
    Wenjing ZHANG, Wengui DUAN, Guishan LIN, Yupei MENG, Zhaolei ZHANG, Xinyan LIU
    2024, 44 (2):  9-19.  doi: 10.3969/j.issn.0253-2417.2024.02.002
    Abstract ( 35 )   HTML ( 127 )   PDF (2069KB) ( 64 )   Save

    Using piperitone as the raw material, 42 novel(Z)-/(E)-piperitone-based pyrazole-oxime ester(compounds 6a-6u, including 21 pairs of Z/E isomers) were synthesized through O-acylation reactions with substituted pyrazoles after carbonyl oximation. The structures of the target products were characterized using proton-1 nuclear magnetic resonance spectrum(1H NMR), carbon-13 nuclear magnetic resonance spectrum(13C NMR), Fourier-transform infrared spectroscopy(FT-IR), and high-resolution mass spectrometry(HRMS). The Z/E configurations of the compounds were determined by single-crystal X-ray diffraction analysis(SC-XRD). In vitro bioactivity tests showed that the(Z)-/(E)-piperitone-based pyrazole-oxime ester compounds exhibited certain antifungal activities against eight plant pathogenic bacteria, including Fusarium oxysporum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoctonia solani, Bipolaris maydis, and Colleterichum orbiculare, at a mass concentration of 50 mg/L. The antibacterial activity was significantly influenced by the Z/E configurations of the compounds, and their activities against A. solani were found to be the most efficient. Wherein, (Z)-piperitone-based(3′, 5′-difluoromethyl)phenyl pyrazole-oxime ester((Z)-6o), (Z)-piperitone-based(p-trifluoromethyl)phenyl pyrazole-oxime ester((Z)-6u), (Z)-piperitone-based(p-nitro)phenyl pyrazole-oxime ester((Z)-6p), (E)-piperitone-based(p-nitro)phenyl pyrazole-oxime ester((E)-6p), (Z)-piperitone-based(p-trifluoromethoxy)phenyl pyrazole-oxime ester((Z)-6g), and(E)-piperitone-based(o-fluoro)phenyl pyrazole-oxime ester((E)-6i) exhibited the inhibition rates of 83.8%, 78.7%, 76.3%, 76.3%, 74.8%, and 74.3%, respectively, against A. solani. And compound(Z)-6u showed the inhibition rate of 82.5% against P. piricola, which was better than that of the positive control chlorothalonil. The three-dimensional quantitative structure-activity relationship(3D-QSAR) model(r2=0.928, q2=0.732) for the inhibitory activity of(Z)-piperitone-based pyrazole-oxime ester compounds against A. solani was established using comparative molecular field analysis(CoMFA) method.

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    Preparation of Nano-flower-shaped Carbon Loaded Ag-ZnO Using Lignin Template Method and Its Photocatalytic CO2 Conversion
    Bihui AN, Haojie CHEN, Lili ZHANG, Jinxia MA, Zhiguo WANG
    2024, 44 (2):  20-26.  doi: 10.3969/j.issn.0253-2417.2024.02.003
    Abstract ( 33 )   HTML ( 84 )   PDF (10033KB) ( 44 )   Save

    Using lignin(AL) as a template, nanoscale lignin-loaded zinc oxide(ZnO/AL) composite materials were prepared. Silver nanoparticles(AgNPs) were loaded onto this base material, and a nano-flower-shaped carbon loaded silver-zinc oxide(Ag-ZnO/C) composite material was prepared through high-temperature calcination. The composite materials were characterized using scanning electron microscopy(SEM), transmission electron microscopy(TEM), X-ray diffraction(XRD), and X-ray photoelectron spectroscopy(XPS), and their ability for photocatalytic conversion of CO2 was evaluated. The research results showed that when using lignin as a template, ZnO/AL could maintain the nano-flower morphology and structure during the subsequent calcination processes, and lignin could reduce silver ions in situ to AgNPs, uniformly loading them on the ZnO petal layers. Energy-dispersive X-ray spectroscopy(EDX) results showed that Ag-ZnO/C composite material was mainly composed of C(14.7%), O(14.4%), Zn(34.1%) and Ag(18.0%) elements. Combined with TEM, XRD, and XPS analysis, the successful preparation of the Ag-ZnO/C composite material was confirmed. The ability of photocatalytic CO2 conversion of the composite materials with different Ag+/Zn2+ ratios of 1∶2(Ag0.1-ZnO0.2/C) and 1∶10(Ag0.1-ZnO1.0/C) was compared. Photocurrent response and impedance spectroscopy test results indicated that Ag0.1-ZnO1.0/C had higher photocurrent intensity, lower resistance, and superior photocatalytic activity. The photocatalytic CO2 conversion by Ag0.1-ZnO1.0/C showed consistently low CH4 production, and the CO yield could reach 114.9 μmol/g after 10 hours of reaction.

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    Preparation of Hydrolysates from Ginkgo biloba Seed Protein Isolate and Their Antioxidant Activity
    Xiang WANG, Caihong ZHANG, Jianxin JIANG, Pujun XIE, Lixin HUANG
    2024, 44 (2):  27-32.  doi: 10.3969/j.issn.0253-2417.2024.02.004
    Abstract ( 31 )   HTML ( 143 )   PDF (506KB) ( 41 )   Save

    Ginkgo biloba seed protein isolate(GBSPI) was hydrolyzed by alcalase, bromelain, and Aspergillus oryzae protease, and the antioxidant activity of the hydrolysates was evaluated through in vitro DPPH radical, hydroxyl radical, and superoxide anion radical scavenging experiments. The results showed that the yields of hydrolysates by alcalase, bromelain, and Aspergillus oryzae protease were 93.60%, 60.00% and 46.80%, with degrees of hydrolysis were 13.76%, 6.28% and 5.55%, respectively. The hydrolysates from three enzymes exhibited good inhibitory effects on DPPH radical, hydroxyl radical, and superoxide anion radical. Among them, the hydrolysate from alcalase showed the strongest antioxidant activity, with IC50 values of 5.29 g/L for DPPH radical, 0.35 g/L for hydroxyl radical, and 7.01 g/L for superoxide anion radical, respectively.

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    Preparation of Visible Light Response ZnIn2S4 Catalyst with S Vacancy and Its Selective Oxidation of HMF
    Lifei XU, Haoqiang HOU, Chunhui MA, Wei LI, Sha LUO, Shouxin LIU
    2024, 44 (2):  33-41.  doi: 10.3969/j.issn.0253-2417.2024.02.005
    Abstract ( 29 )   HTML ( 136 )   PDF (6125KB) ( 38 )   Save

    A visible light response catalyst with abundant S vacancies, zinc indium sulfide(VS-ZIS), was prepared in situ by one-step method using thioacetamide as the sulfur source. The process of selective photocatalytic oxidation of 5-hydroxymethylfurfural(HMF) to 2, 5-diformylfuran(DFF) over VS-ZIS was studied, and the mechanism of VS-ZIS photocatalytic selective oxidation of HMF to DFF was analyzed. The existence of S vacancies was confirmed by electron paramagnetic resonance(EPR). The optical properties and elemental composition of VS-ZIS were investigated by UV-vis diffuse reflectance spectroscopy(DRS) and XPS, and the surface morphology and crystal structure of the catalyst were observed using SEM and XRD. The results showed that ZnIn2S4 could be successfully synthesized by the one-step method. The catalyst exhibited a petal-like microsphere morphology, and the elements of Zn, In, and S were uniformly distributed. The visible light absorption range of the catalyst was 420-530 nm. The synthesis time did not has significantly effect on the crystal structure of ZnIn2S4, while the S vacancies in the catalyst could be controlled by adjusting the synthesis time. Among the samples of VS-ZIS-2 to VS-ZIS-10 prepared at 2-10 h, the sample VS-ZIS-6 obtained at 6 h had abundant S vacancies. The VS-ZIS-6 prepared by heating at 80 ℃ for 6 h showed the best performance for the selective oxidation of HMF under the conditions of a reaction time of 4 h, VS-ZIS-6/HMF mass ratio of 3.2, HMF concentration of 1.0 mmol/L, and air flow rate of 20 mL/min. The HMF conversion rate reached 95.4%, and the DFF yield was 61.8%. The abundant S vacancies on the surface of VS-ZIS could promote the adsorption and activation of O2 on the catalyst surface, capturing photoinduced electrons to generate more O2-·, thereby enhancing the selective oxidation ability of the catalyst towards HMF.

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    Preparation and Properties of a Cellulose-based Flexible Film with Conductive Stability
    Minjie HOU
    2024, 44 (2):  42-48.  doi: 10.3969/j.issn.0253-2417.2024.02.006
    Abstract ( 30 )   HTML ( 214 )   PDF (8037KB) ( 35 )   Save

    Dopamine molecules were introduced onto the surface of cellulose nanofibers(CNF) through amidation reaction, resulting in dopamine-modified cellulose nanofibers(DCF). High-transparency DCF/montmorillonite(MMT) film materials were prepared by combining DCF with MMT. Silver nanowires(AgNWs) and graphene oxide(GO) were further deposited on the film through vacuum filtration to prepare cellulose-based transparent conductive films. The test results showed that the grafting of dopamine molecules did not affect the morphology and crystalline structure of CNF. The prepared DCF/MMT film maintained a high transmittance(82.4%) and exhibited a tensile strength of 49.5 MPa at a relative humidity of 100%, which was a 64% improvement compared to that of CNF/MMT film. The conductive films assembled with this material exhibited good transparency, conductivity, and electrical stability. The DCF/MMT/AgNWs/GO (DMAG) film demonstrated stable high conductivity after water immersion or exposure to high humidity(relative humidity of 90%), with the sheet resistances of 32 and 38 Ω, respectively. The preparation of this conductive film provides a new approach for the assembly of transparent electronic devices.

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    Synthesis and Properties of Fully Bio-based Polyester Hot-melt Adhesive
    Hongsheng WANG, Ren YE, Daihui ZHANG, Chunpeng WANG, Shishuai GAO
    2024, 44 (2):  49-54.  doi: 10.3969/j.issn.0253-2417.2024.02.007
    Abstract ( 28 )   HTML ( 211 )   PDF (723KB) ( 37 )   Save

    Using bio-based 2, 5-furandicarboxylic acid(FDCA), oil-based hydrogenated dimer acid(Pripol 1009), and bio-based 1, 4-butanediol(bio-BDO) as raw materials, a poly(2, 5-furandicarboxylic acid butanediol ester-co-hydrogenated dimer acid butanediol ester)(PBDF-20) thermoplastic polyester hot melt adhesive was prepared through melt polycondensation method. This adhesive was then applied in the wood processing field, and various methods were employed to characterize the polyester and plywood. The results showed that the polyester was a semi-crystalline polymer with a nano-scale microphase separation structure, where the dispersed phase had a long period of 14.3 nm. Its glass transition temperature and melting point were -12.8 ℃ and 148.6 ℃, respectively. The tensile strength and elongation at break were 22.6 MPa and 528%, respectively. The bonding strength of the poplar plywood bonded with PBDF-20 as adhesive met the requirements of Class Ⅰ plywood in terms of bonding strength, and the formaldehyde emission was less than 0.025 mg/L, complying with the ENF grade standard.

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    Preparation of Iron Based Carbon Aluminum Catalyst and Its Catalytic for Hydrogen Production from Corn Straw Pyrolysis
    Yan LU, Xueqin LI, Yanling LI, Tanglei SUN, Peng LIU, Tingzhou LEI
    2024, 44 (2):  55-63.  doi: 10.3969/j.issn.0253-2417.2024.02.008
    Abstract ( 29 )   HTML ( 182 )   PDF (1400KB) ( 35 )   Save

    An iron-based carbon-aluminum catalyst(Fe/CS-AWA) was prepared using hydrothermal carbonization(HTC) method, using corn stover(CS) biomass as the raw material, activated aluminum ash(AWA) activated by waste aluminum ash(WA) as a carrier and Fe as the active component. The Fe/CS-AWA was applied in catalyzing the pyrolysis of CS for hydrogen production. By investigating the influence of Fe loading on the catalyst performance, the hydrothermal carbonization conditions on the structural properties of Fe/CS-AWA and the effect of catalytic CS pyrolysis on hydrogen production were further optimized using response surface methodology(RSM).The results indicated that compared with CS pyrolysis, AWA and CS mixed hydrothermal carbonization as a catalyst increased the hydrogen production capacity of CS pyrolysis by 19. 11 mL/g. More importantly, Fe enhanced the catalytic activity of CS-AWA, with a gas total yield of 160. 93 mL/g and hydrogen proportion of 39.96% when the Fe loading was 10%. The optimized process conditions from RSM were as follows: mAWAmCS of 2 ∶ 1, residence time of 60 min at 250 ℃, and a carbonization temperature of 500 ℃. Under these conditions, the gas total yield for Fe/CS-AWA catalyzing CS pyrolysis was 267. 43 mL/g, with a H2 proportion of 37. 80%. It was found that characterization revealed the formation of irregular iron carbides and Al—O—C intermediates on the surface of Fe/CS-AWA, enhancing the catalytic activity of Fe/CS-AWA.

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    Cellulase-assisted Hydrolysis of Camellia oleifera Seed Meal to Extract Saccharicterpenin and Its Product Validation
    Leping ZHANG, Yuejie QIU, Chunrui HAN, Jianxin JIANG
    2024, 44 (2):  64-70.  doi: 10.3969/j.issn.0253-2417.2024.02.009
    Abstract ( 37 )   HTML ( 121 )   PDF (686KB) ( 42 )   Save

    The extraction of saccharicterpenin from Camellia oleifera cake meal by cellulase hydrolysis method was studied, with the saccharicterpenin yield as the investigation target. An orthogonal experiment was conducted to explore the effects of cellulase dosage, extraction time, liquid-to-solid ratio, extraction temperature, and pH value on the saccharicterpenin yield. The results showed that under the optimal experimental conditions of a solid-to-liquid of 1 ∶ 15(g ∶ mL), cellulase dosage of 4%, enzymatic hydrolysis pH value of 5.0, extraction temperature of 50 ℃, and extraction time of 120 min, the saccharicterpenin yield was 18.39%. The extract was found to conform to the basic structural characteristics of saccharicterpenin through infrared spectroscopy and high-performance liquid chromatography. Identification and component determination of saccharicterpenin were performed according to the national standard method of GB/T 25247—2010. The mass fractions of total sugars and total saccharicterpenin were more than 30%, and the mass fraction of proteins exceeded 7%. Saccharicterpenin exhibited good DPPH radical scavenging ability, with a clearance rate of 90.28% at a mass concentration of 1 g/L. And there was no hemolytic activity at mass concentration less than 5 mg/L, which had good prospects for application as a feed additive.

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    Preparation and Properties of Bio-based Schiff Base Self-repairing Polyurethane
    Xu FAN, Fuhao DONG, He LIU, Jianxin JIANG, Zhanqian SONG
    2024, 44 (2):  71-78.  doi: 10.3969/j.issn.0253-2417.2024.02.010
    Abstract ( 37 )   HTML ( 46 )   PDF (2267KB) ( 38 )   Save

    Dynamic covalent bonds were a type of chemical bond that can be broken and restored under specific conditions. Among them, Schiff base was a dynamic covalent bond formed by the condensation of aldehydes and amine compounds. A bio-based Schiff base compound(MV/S) was synthesized by the reaction between the amine group of 1, 8-p-menthanediamine(MD) with the aldehyde group of vanillin. A Schiff base compound(EV/S) without aliphatic ring was synthesized by replacing MD with ethylenediamine. Using MV/S and EV/S as chain extenders, the self-healing Schiff base polyurethane films(PU/SM and PU/SE) were prepared, At the sametime, the polyurethane without Schiff base(PU/BDO) prepared without MV/S and EV/S was used as a blank control to determine the effect of MD on the properties of self-healing polyurethane. Various analytical and testing methods were employed to study the structure, mechanical properties, and self-healing performance of the polyurethanes. The results showed that the tensile strength of PU/SM was 30.7 MPa, which was 20.1 MPa higher than that of PU/BDO. TG/DTG analysis revealed that the introduction of MD significantly improved the heat resistance of PU/SM. Comparison at the same temperature showed a significant reduction in relaxation time of PU/SM compared to that of PU/SE, indicating that the introduction of MD promoted the exchange rate of dynamic covalent bonds. Compared with PU/SE, PU/SM exhibited a faster relaxation rate, and the activation energy was reduced by 35. 84 kJ/mol. The results of self-healing performance tests demonstrated that PU/SM had superior self-healing properties compared to PU/BDO and PU/SE, with a self-healing rate of 77% for the sheared PU/SM film after 24 h of heating at 80 ℃.

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    Preparation of Bifunctional Carbon-based Solid Acid and Its Catalytic Alcoholysis of Cellobiose
    Teng FAN, Ronghua ZHANG, Kui WANG, Hui PAN, Junfeng FENG
    2024, 44 (2):  79-86.  doi: 10.3969/j.issn.0253-2417.2024.02.011
    Abstract ( 31 )   HTML ( 118 )   PDF (885KB) ( 38 )   Save

    Chitosan was used as a carbon source to prepare iron-loaded nitrogen-containing activated carbon(ACN-Fe) through metal impregnation and high-temperature carbonization. A series of metal-loaded dual-functional carbon-based solid acid(ACN-Fe-SO3H) catalysts were further prepared by hydrothermal sulfonation. The catalysts were applied to catalyze the alcoholysis of cellobiose. The catalysts were characterized in detail using X-ray diffraction(XRD), Raman spectroscopy, Fourier-transform infrared spectroscopy(FT-IR), N2 adsorption/desorption, X-ray photoelectron spectroscopy(XPS), inductively coupled plasma optical emission spectrometry(ICP-OES), and acid-base titration. The results showed that the unsaturated trivalent iron ions in the catalyst had Lewis acidity, while the sulfonic acid groups exhibited Brønsted acidity. The catalyst prepared at a carbonization temperature of 800 ℃(800-ACN-Fe-SO3H) possessed the strongest acidity(acidity of 0. 81 mmol/g) and the best structural characteristics(specific surface area of 85.7 m2/g), showing the best catalytic performance. With a catalyst dosage of 0. 20 g, a reaction temperature of 200 ℃, and a reaction time of 5 h, the cellobiose conversion rate reached 99. 6%, with yields of levulinic acid(LA) and methyl levulinate(ML) of 15.6% and 62.1%, respectively. After 5 cycles, the cellobiose conversion rate remained 93.1%, with a product yield of 51.1%, indicating good catalyst reusability. Additionally, a preliminary exploration of the reaction mechanism of cellobiose alcoholysis was conducted.

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    Preparation and Characterization Analysis of Activated Carbon from Camellia oleifera Shell by K2CO3 Activation
    Liwei PU, Lihuan MO, Yin HU, Jun LI
    2024, 44 (2):  87-93.  doi: 10.3969/j.issn.0253-2417.2024.02.012
    Abstract ( 32 )   HTML ( 143 )   PDF (1933KB) ( 43 )   Save

    Using K2CO3 as the activating agent, Camellia oleifera shell(COS) was used as the raw material to prepare COS-based activated carbon through activation in both air and nitrogen atmospheres. The effects of activation temperature, activation time, and K2CO3 impregnation ratio(mL ∶ g) on the preparation of activated carbon were investigated. The activated carbon was characterized using elemental analysis, Fourier-transform infrared spectroscopy(FT-IR), scanning electron microscopy(SEM), and other methods. The results showed that with an impregnation ratio of 1. 5, temperature of 800 ℃, and carbonization activation time of 1 h in air atmosphere, the obtained activated carbon had the yield of 12.48%, specific surface area o f 1 080. 94 m2/g, and methylene blue(MB) adsorption value of 441. 62 mg/g. When activated in nitrogen with impregnation ratio of 2. 5, temperature of 800 ℃, and carbonization activation time of 1 h, the obtained activated carbon had the yield of 18. 00%, specific surface area of 942. 42 m2/g, and MB adsorption value of 428.77 mg/g. The results of elemental analysis showed that activated carbon prepared under a nitrogen atmosphere had a lower H/C elemental ratio and the aromaticity was improved. FT-IR and SEM analysis indicated that activation promoted the thermal decomposition of —CH and —COOH groups and the growth of pores in the activated carbon. Compared to the samples prepared under a nitrogen atmosphere, activated carbon produced by air as pyrolysis had more developed pores and better adsorption performance.

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    Preparation and Properties of Starch/Carboxymethyl Cellulose/Glycerol Degradable Composite Films
    Dongyang JIANG, Nannan LI, Haiyuan HUANG, Zeguang ZHOU, Yanyue LU, Lei ZHONG
    2024, 44 (2):  94-102.  doi: 10.3969/j.issn.0253-2417.2024.02.013
    Abstract ( 31 )   HTML ( 125 )   PDF (10016KB) ( 38 )   Save

    Starch/carboxymethyl cellulose(CMC)/glycerol composite film was fabricated with a casting method by mixing starch CMC and glycerol used as a plasticizer. The structure of the composite film was characterized by SEM, XRD, and FT-IR, and the mechanics, light transmittance, water absorption, and degradation properties of the composite film were studied. The effect of different glycerol addition levels(based on the total dry mass of starch and CMC, 0-30%) on the structure and properties of the composite film were mainly investigated. The results showed that starch, CMC, and glycerol were physically blended, and the addition of glycerol improved the compatibility of the system. The more glycerol added, the smoother fracture surface of the composite film was achieved. As the glycerol addition increased, the elongation at break of the composite film significantly increased. When the addition increased from 0 to 30%, the elongation at break increased from 3.39% to 46.23%, which was an increase of 12.6 times. The transmittance, water absorption, and water vapor permeability(WVP) of the composite film increased with increase of glycerol addition. When the addition was 20%, the maximum transmittance at 600 nm reached 79.42%, and the WVP and water absorption were 5.14×10-11 g/(m · s · Pa) and 25.46%, respectively. The increase of glycerol addition in the system could also accelerate the degradation rate of the composite film. When the glycerol addition was 20%, the composite film almost completely degraded within 9 days. The results showed that the mechanical, optical and degradable properties of starch/CMC/glycerol composite film were better when the glycerol content was 20%, which could meet the performance requirements of food packaging film.

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    Synthesis and Herbicidal Activity of Terpinyl Phthalimide Derivatives
    Yun ZHANG, Guangtong ZHU, Meifang ZHUO, Yanmin HUANG, Qijin MO
    2024, 44 (2):  103-110.  doi: 10.3969/j.issn.0253-2417.2024.02.014
    Abstract ( 33 )   HTML ( 213 )   PDF (631KB) ( 47 )   Save

    Using α-terpinene(1) as the starting material, dimethyl terpinylbutenedioate(2) was synthesized through its Alder-Rickert reaction with dimethyl butenedioate. Terpinyl phthalic anhydride(3) was subsequently synthesized by their ring-closing reaction. Afterwards, 13 novel terpinyl phthalimide derivatives(4a-4m) were synthesized by the substitution reactions of compound 3 with a series of aromatic amine compounds. The structures of the target compounds were characterized by IR, ESI-MS, 1H NMR and 13C NMR, and the successful synthesis of the target compounds 4a-4m was confirmed. Preliminary herbicidal activity tests results showed that most synthetic compounds exhibited certain herbicidal activity against Echinochloa crusgalli(L.) Beauv, Digitaria sanguinalis(L.) Scop., Abutilon theophrasti Medicus and Amaranthus retroflexus when they were applied to the stems and leaves at a dosage of 1.5 kg/hm2. Among them, compounds 4b(R=p-CH3) and 4c(R=p-OCH3) showed the highest inhibitory activity and reached grade B against A. theophrasti Medicus with the inhibition rates of 62.2% and 64.0%, respectively.

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    Structure and Properties of Soy Protein Adhesive Modified by Urea-Glyoxal Resin
    Shunyao YANG, Qiheng LI, Jun ZHANG, Yan XIA, Guanben DU, Shuduan DENG
    2024, 44 (2):  111-118.  doi: 10.3969/j.issn.0253-2417.2024.02.015
    Abstract ( 29 )   HTML ( 176 )   PDF (613KB) ( 40 )   Save

    Soy protein-based adhesive(SUG) was prepared using urea-glyoxal(UG) resin and soy protein isolate(SPI) as the main raw materials, and the solid content, viscosity, surface tension coefficient, contact angle, and bonding performance of the soy protein-based adhesive were tested. Then, the structure of the synthesized soy protein-based adhesive was characterized by XPS, FT-IR and 13C NMR. The curing performance of the adhesive was determined by DSC and DMA. The results showed that the solid content, viscosity, surface tension coefficient, and contact angle of the modified soy protein adhesive increased with the increase of SPI content, where the viscosity exhibited the most significant change. The synthesized soy protein adhesive mainly contained functional groups such as C—C, C—O—C, C=O, C—N and C—O. Combined with the results of 13C NMR and FT-IR analysis, it could conclud that cross-linking occurred between UG resin and SPI. When the amount of SPI was 30 g and the amount of UG resin was 50 g, the prepared soy protein adhesive exhibited better performance, and the cured adhesive had a high storage modulus, which was 4 082 MPa. The wet strength values of the plywood prepared at 160 ℃ and 180 ℃ hot pressing temperatures in cold water for 24 h were 1.23 and 1.48 MPa, respectively. The hot water wet strength values after 3 h were 1.05 and 1.22 MPa, which were significantly higher than the requirements for Class II plywood according to the national standard GB/T 9846—2015, and the prepared plywood adhesive exhibited a certain level of water resistance.

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    Preparation of NiMoRe/HZSM-5 Catalyst for Hydrodeoxygenation of Fatty Acid Methyl Ester
    Xiaobo GUO, Wenduo JIANG, Wenbiao HOU, Ping ZHAO, Junming XU, Peng LIU
    2024, 44 (2):  119-126.  doi: 10.3969/j.issn.0253-2417.2024.02.016
    Abstract ( 35 )   HTML ( 172 )   PDF (3675KB) ( 36 )   Save

    A 5 kg NiMoRe/HZSM-5 catalyst was prepared by impregnation method, and the physicochemical properties of the catalyst were analyzed using characterization techniques such as X-ray diffraction(XRD), scanning electron microscopy(SEM), and inductively coupled plasma optical emission spectrometry(ICP-OES). The optimal conditions for the catalyst in the hydrogenation deoxygenation reaction of stearic acid methyl ester were explored. The research results showed that, compared to three commercial catalysts, the metal nickel in NiMoRe/HZSM-5 had smaller and more uniformly dispersed particles, a larger BET specific surface area(SBET) of 239.1 m2/g, and exhibited better catalytic activity. Under the optimal reaction conditions of 260 ℃, catalyst dosage of 0.3 g, reaction time of 4 hours, and initial H2 pressure of 3 MPa, both the raw material conversion rate and alkane selectivity were 100%. The catalyst demonstrated good stability, with a high raw material conversion rate of 96.1% even after the 5th cycle, and the ratio of hydrogenation deoxygenation(HDO) reaction to decarboxylation/decarbonylation(DCO) reaction decreased from 1.2 to 0.56. After scaling up the hydrogenation deoxygenation reaction of fatty acid methyl ester under solvent-free conditions using the NiMoRe/HZSM-5 catalyst, a pilot-scale evaluation was conducted on 25 kg of fatty acid methyl ester in a 2.8 L fixed bed reactor. After 15 cycles, the fatty acid methyl ester achieved a conversion rate of 98%.

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    Research Progress in the Application of Machine Learning in the Preparation and Application of Biochar
    Bufei WANG, Yuanchong YUE, Mei WANG, Kang SUN, Shule WANG, Quan BU
    2024, 44 (2):  127-137.  doi: 10.3969/j.issn.0253-2417.2024.02.017
    Abstract ( 44 )   HTML ( 149 )   PDF (1002KB) ( 48 )   Save

    In recent years, machine learning had made great progress in predicting and optimizing the preparation and application of biochar. This paper provided a comprehensive review of the role of machine learning in facilitating the preparation and application of biochar. The machine learning models applied in the preparation and application of biochar were mainly introduced, as well as some suggestions for the latest research.

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    Research Progress on Hydrophobic Modification and Application of Cellulose Base Materials
    Peishan SUI, Juntao ZHANG, Mingming ZHENG, Yufei ZHANG, Jiayuan SHEN
    2024, 44 (2):  138-146.  doi: 10.3969/j.issn.0253-2417.2024.02.018
    Abstract ( 37 )   HTML ( 130 )   PDF (4300KB) ( 46 )   Save

    The research progress on hydrophobic modification of polymorphic cellulose materials(such as filter paper, cotton fabric, polymer film, fiber foams, and aerogels, etc.) was comprehensively reviewed, with particular emphasis on modification methods including spraying method, impregnation method, plasma method, chemical vapor deposition method, sol-gel method, atom transfer radical polymerization, "thiol-ene" click reaction, etc. Furthermore, the application research progress of cellulose-based superhydrophobic materials in the field of waterproofing, anti-icing, flame retardancy, and oil-water separation was discussed. Finally, the problems and development prospects of hydrophobic modification of cellulose-based materials were summarized and prospected.

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