Chemistry and Industry of Forest Products ›› 2023, Vol. 43 ›› Issue (2): 116-126.doi: 10.3969/j.issn.0253-2417.2023.02.015
Previous Articles Next Articles
Chunyu REN1, Xiangyu LIN2, Zhuomin WANG1, He LIU1,*()
Received:
2022-01-09
Online:
2023-04-28
Published:
2023-04-26
Contact:
He LIU
E-mail:liuhe_caf@163.com
CLC Number:
Chunyu REN, Xiangyu LIN, Zhuomin WANG, He LIU. Preparation of Porous Graphite Carbon Nitride and Its Visible Light Catalytic Conversion of Lignin[J]. Chemistry and Industry of Forest Products, 2023, 43(2): 116-126.
Table 1
Photocatalytic transformation of model compound 1(2-phenoxy-1-phenylethanol) under different reaction conditions"
编号 No. | 催化剂 catalyst | 溶剂 solvent | 1转化率/% 1 conversion | 产率yield/% | C—C断裂选择性/% selectivity of C—C fracture | |||
2 | 3 | 4 | 5 | |||||
a | 无none | CH3CN | 0 | — | — | — | — | — |
b | BCN | CH3CN | 57.22 | 49.53 | 15.98 | 1.83 | 5.65 | 90.09 |
c | mpg-CN | CH3CN | 98.06 | 81.70 | 31.03 | 8.36 | 8.05 | 91.79 |
d | BCN | C2H5OH | 11.51 | 4.82 | 8.87 | 2.98 | 2.40 | 76.47 |
e | mpg-CN | C2H5OH | 19.64 | 13.19 | 9.19 | 3.46 | 2.67 | 86.18 |
f | BCN | V(CH3CN)∶V(H2O)=1∶1 | 71.95 | 64.04 | 28.86 | 1.68 | 5.38 | 92.43 |
g | mpg-CN | V(CH3CN)∶V(H2O)=1∶1 | 79.86 | 72.11 | 30.16 | 3.06 | 4.83 | 93.96 |
h | BCN | CH3COCH3 | 42.17 | 31.34 | 13.74 | 1.53 | 9.79 | 77.05 |
i | mpg-CN | CH3COCH3 | 52.29 | 34.49 | 19.72 | 8.19 | 10.08 | 80.89 |
j | mpg-CN (黑暗dark) | CH3CN | 5.86 | — | — | — | — | — |
k | mpg-CN(Ar) | CH3CN | 3.59 | — | — | — | — | — |
Table 2
Results of transformation of model compound 1 in mpg-CN samples in different scavengers solutions"
编号 No. | 清除剂名称 scavengers name | 清除剂类型 scavengers type | 1转化率/% 1 conversion |
1 | 无none | 无none | 88.02 |
2 | TEMPO | 自由基中间体free radical intermediate | 5.63 |
3 | K2S2O8 | 光生电子photogenerated electron(e-) | 91.66 |
4 | (NH4)2C2O4 | 光生空穴photogenerated hole(h+) | 70.58 |
5 | 叔丁醇t-BuOH | ·OH | 86.79 |
6 | 对苯醌p-BQ | O2- | 95.48 |
1 |
LI C Z , ZHAO X C , WANG A Q , et al. Catalytic transformation of lignin for the production of chemicals and fuels[J]. Chemical Reviews, 2015, 115 (21): 11559- 11624.
doi: 10.1021/acs.chemrev.5b00155 |
2 |
SUN Z , BOTTARI G , AFANASENKO A , et al. Complete lignocellulose conversion with integrated catalyst recycling yielding valuable aromatics and fuels[J]. Nature Catalysis, 2018, 1 (1): 82- 92.
doi: 10.1038/s41929-017-0007-z |
3 | YAN J, MENG Q L, SHEN X J, et al.Selective valorization of lignin to phenol by direct transformation of Csp2-Csp3 and C-O bonds[J/OL]. Science Advances, 2020, 6(45): eabd1951[2021-12-20]. http://doi.org/10.1126/sciadv.abd1951. |
4 |
WU X J , LUO N C , XIE S J , et al. Photocatalytic transformations of lignocellulosic biomass into chemicals[J]. Chemical Society Review, 2020, 49 (17): 6198- 6223.
doi: 10.1039/D0CS00314J |
5 |
XING Z Y , HAN W Y , DENG J , et al. Photocatalytic conversion of lignin to chemicals and fuels[J]. ChemSusChem, 2020, 13 (17): 4199- 4213.
doi: 10.1002/cssc.202000601 |
6 | 孔劼琛, 骆治成, 李愽龙, 等. 木质素解聚和加氢脱氧的进展[J]. 中国科学(化学), 2015, 45 (5): 510- 525. |
KONG J C , LUO Z C , LI B L , et al. Advances in depolymerization and hydrodeoxygenation of lignin[J]. Scientia Sinica Chimica, 2015, 45 (5): 510- 525. | |
7 |
LIU X , FLORENT P B , FAN J , et al. Recent advances in the catalytic depolymerization of lignin towards phenolic chemicals: A review[J]. ChemSusChem, 2020, 13 (17): 4296- 4317.
doi: 10.1002/cssc.202001213 |
8 | 江昊翰, 李双明, 于三三. 木质素解聚和液相催化降解研究进展[J]. 生物质化学工程, 2022, 56 (4): 67- 76. |
JIANG H H , LI S M , YU S S . Research progress on depolymerization and liquid phase catalytic degradation of lignin[J]. Biomass Chemical Engineering, 2022, 56 (4): 67- 76. | |
9 | 舒日洋, 徐莹, 张琦, 等. 木质素催化解聚的研究进展[J]. 化工学报, 2016, 67 (11): 4523- 4532. |
SHU R Y , XU Y , ZHANG Q , et al. Progress in catalytic depolymerization of lignin[J]. Chinese Journal of Chemical Engineering, 2016, 67 (11): 4523- 4532. | |
10 |
KOBAYAKAWA K , SATO Y , NAKAMURA S A , et al. Photodecomposition of Kraft lignin catalyzed by titanium dioxide[J]. Bulletin of the Chemical Society of Japan, 1989, 62 (11): 3433- 3436.
doi: 10.1246/bcsj.62.3433 |
11 |
LIU J X , LI Y J , LIU H M , et al. Photo-thermal synergistically catalytic conversion of glycerol and carbon dioxide to glycerol carbonate over Au/ZnWO4-ZnO catalysts[J]. Applied Catalysis B: Environmental, 2019, 244, 836- 843.
doi: 10.1016/j.apcatb.2018.12.018 |
12 | LIU Z L , JIN Y J , TENG F , et al. An efficient Ce-doped MoO3 catalyst and its photo-thermal catalytic synergetic degradation performance for dye pollutant[J]. Catalysis Communications, 2015, 66 (5): 42- 45. |
13 |
GAO W , LIU W , LENG Y , et al. In2S3 nanomaterial as a broadband spectrum photocatalyst to display significant activity[J]. Applied Catalysis B: Environmental, 2015, 176/177, 83- 90.
doi: 10.1016/j.apcatb.2015.03.048 |
14 | WU X J , FAN X T , XIE S J , et al. Solar energy-driven lignin-first approach to full utilization of lignocellulosic biomass under mild conditions[J]. Nature Catalysis, 2018, 1 (1): 772- 780. |
15 |
LI X , YU J G , WAGEH S , et al. Graphene in photocatalysis: A review[J]. Small, 2016, 12 (48): 6640- 6696.
doi: 10.1002/smll.201600382 |
16 |
VAN CAN N , KE N J , NAM L D , et al. Photocatalytic reforming of sugar and glucose into H2 over functionalized graphene dots[J]. Journal of Materials Chemistry A, 2019, 7, 8384- 8393.
doi: 10.1039/C8TA12123K |
17 |
HAN G Q , YAN T , ZHANG W , et al. Highly selective photocatalytic valorization of lignin model compounds using ultrathin metal/CdS[J]. ACS Catalysis, 2019, 9 (12): 11341- 11349.
doi: 10.1021/acscatal.9b02842 |
18 |
MAJDOUB M , ANFAR Z , AMEDLOUS A . Emerging chemical functionalization of g-C3N4: Covalent/noncovalent modifications and applications[J]. ACS Nano, 2020, 14 (10): 12390- 12469.
doi: 10.1021/acsnano.0c06116 |
19 | 刘爽爽, 李娟, 史佳菲, 等. g-C3N4光催化剂改性方法的研究进展[J]. 山东化工, 2020, (7): 85- 89. |
LIU S S , LI J , SHI J F , et al. Research progress on the modification of g-C3N4 photocatalyst[J]. Shandong Chemical Industry, 2020, (7): 85- 89. | |
20 | SHI L , LIANG L , WANG F X , et al. Higher yield urea-derived polymeric graphitic carbon nitride with mesoporous structure and superior visible-light-responsive activity[J]. ACS Sustainable Chemistry & Engineering, 2015, 3 (12): 3412- 3419. |
21 | 卢辛成, 蒋剑春, 孙康, 等. 活性炭比表面积、孔径对TiO2/AC光催化活性的影响[J]. 林产化学与工业, 2010, 30 (6): 29- 34. |
LU X C , JIANG J C , SUN K , et al. Effect of activated carbon surface area, pore size on photocatalytic activity of TiO2/AC[J]. Chemistry and Industry of Forest Products, 2010, 30 (6): 29- 34. | |
22 | 张杰, 李会鹏, 赵华, 等. 高比表面积g-C3N4的制备及其在光催化制氢中的应用研究进展[J]. 现代化工, 2018, 38 (11): 67- 71. |
ZHANG J , LI H P , ZHAO H , et al. Synthesis of g-C3N4 with high specific surface area and its application advancesin hydrogen production via photocatalysis[J]. Modern Chemical Industy, 2018, 38 (11): 67- 71. | |
23 |
李梅, 张胜波, 刘晓, 等. 硬模板法制备聚合物半导体氮化碳[J]. 高校化学工程学报, 2017, 31 (4): 749- 762.
doi: 10.3969/j.issn.1003-9015.2017.04.001 |
LI M , ZHANG S B , LIU X , et al. Polymeric semiconductor carbon nitride prepared from hard template[J]. Journal of Chemical Engineering of Chinese Universities, 2017, 31 (4): 749- 762.
doi: 10.3969/j.issn.1003-9015.2017.04.001 |
|
24 | 李晓豪, 解从霞. Pd/mpg-C3N4催化剂的制备、表征及其对松香加氢反应的催化性能[J]. 林产化学与工业, 2019, 39 (2): 73- 80. |
LI X H , XIE C X . Preparation and characterization of Pd/mpg-C3N4 catalyst and its catalytic performance for hydrogenation of rosin[J]. Chemistry and Industry of Forest Products, 2019, 39 (2): 73- 80. | |
25 |
HAN Q , CHENG Z H , WANG B , et al. Significant enhancement of visible-light-driven hydrogen evolution by structure regulation of carbon nitrides[J]. ACS Nano, 2018, 12 (6): 5221- 5227.
doi: 10.1021/acsnano.7b08100 |
26 | 艾兵, 刘凡, 韩永磊, 等. 铁掺杂氮化碳的制备及其光催化性能研究[J]. 山东理工大学学报(自然科学版), 2021, 35 (2): 8- 12. |
AI B , LIU F , HAN Y L , et al. Preparation and photocatalytic properties of iron doped carbon nitride[J]. Journal of Shandong University of Technology(Natural Science Edition), 2021, 35 (2): 8- 12. | |
27 | LI Y R, KONG T T, SHEN S H.Artificial photosynthesis with polymeric carbon nitride: When meeting metal nanoparticles, single atoms, and molecular complexes[J/OL]. Small, 2019, 15: 1900772[2021-12-20]. https://doi.org/10.1002/smll.201900772. |
28 | WANG Z Y , GUAN W , SUN Y J , et al. Water-assisted production of honeycomb-like g-C3N4 with ultralong carrier lifetime and outstanding photocatalytic activity[J]. Nanoscale, 2015, 7 (6): 2471- 2479. |
29 | SHALOM M , INAL S , NEHER D , et al. SiO2/carbon nitride composite materials: The role of surfaces for enhanced photocatalysis[J]. Catalysis Today, 2014, 225 (15): 185- 190. |
30 | WANG H , LIU X , NIU P , et al. Porous two-dimensional materials for photocatalytic and electrocatalytic applications[J]. Matter, 2020, 2 (6): 1377- 1413. |
31 | WANG M , LI L H , LU J M , et al. Acid promoted C-C bond oxidative cleavage of β-O-4 and β-1 lignin models to esters over a copper catalyst[J]. Green Chemistry, 2017, 19 (3): 702- 706. |
32 | 聂明才, 霍淑平, 孔振武. 木质素模型化合物的研究进展[J]. 林产化学与工业, 2010, 30 (5): 115- 121. |
NIE M C , HUO S P , KONG Z W . Research progress of lignin model compounds[J]. Chemistry and Industry of Forest Products, 2010, 30 (5): 115- 121. | |
33 | CHEN H, WAN K, ZHENG F J, et al.Mechanism insight into photocatalytic conversion of lignin for valuable chemicals and fuels production: A state-of-the-art review[J/OL]. Renewable and Sustainable Energy Reviews, 2021, 147: 111217[2021-12-20]. https://doi.org/10.1016/j.rser.2021.111217. |
34 | LI W J , LI D Z , LIN Y M , et al. Evidence for the active species involved in the photodegradation process of methyl orange on TiO2[J]. Journal of Physical Chemistry C, 2012, 116 (5): 3552- 3560. |
35 | MITCHELL L J , MOODY C J . Solar photochemical oxidation of alcohols using catalytic hydroquinone and copper nanoparticles under oxygen: Oxidative cleavage of lignin models[J]. Journal of Organic Chemistry, 2014, 79 (22): 11091- 11100. |
36 | HOU T T , LUO N C , LI H J , et al. Yin and yang dual characters of CuOx clusters for C-C bond oxidation driven by visible light[J]. ACS Catalysis, 2017, 7 (6): 3850- 3859. |
[1] | KE Xun, YANG Yuanxing, ZHAO Lihong. Preparation and Properties of UV-shielded Film Derived from Full Components of Bagasse [J]. Chemistry and Industry of Forest Products, 2023, 43(3): 1-8. |
[2] | YE Dawei, WU Yuchao, YANG Zongmei, YU Lin, MAI Yuliang, CHEN Jiazhi. Lignin-based Polyphenols Produced by Alcoholysis-Demethylation and Their Antioxidant Properties [J]. Chemistry and Industry of Forest Products, 2023, 43(3): 34-40. |
[3] | LIU Xuze, ZHAN Yunni, ZHAO Mengke, HUANG Chen, DENG Yongjun, FANG Guigan. Improving Pretreatment Efficiency of Moso Bamboo with Ternary Deep Eutectic Solvent of Choline Chloride/1,4-Butanediol/AlCl3 [J]. Chemistry and Industry of Forest Products, 2023, 43(3): 108-114. |
[4] | DENG Junqian, CHEN Ling, LIAN Hailan. Research Progress of Lignin-based Polyurethane Adhesives [J]. Chemistry and Industry of Forest Products, 2023, 43(3): 160-172. |
[5] | Qingye LIU, Xianyun CHEN, Hua DENG, Weixing GAN, Siyu HUANG, Mianwu MENG. Modification and Characterization of Alkali Lignin by Choline-chloride/Lactic Acid Deep Eutectic Solvents Catalyzed by Sodium Carbonate [J]. Chemistry and Industry of Forest Products, 2023, 43(1): 89-96. |
[6] | Jiewang YE, Zhidan ZHOU, Zhenfu JIN. Preparation, Characterization and Adsorption Properties of Nitrogen-doped Lignin-based Activated Carbon [J]. Chemistry and Industry of Forest Products, 2023, 43(1): 127-132. |
[7] | Ningxin WEI, Xixin DUAN, Wenbiao XU, Junyou SHI. Degradation of Lignin to Phenolic Compounds by Polyacid/H2O2 System [J]. Chemistry and Industry of Forest Products, 2022, 42(6): 55-63. |
[8] | Wenqi LUO, Yimin XIE, Gongxia ZHANG. Pretreatment of Poplar Heartwood by White-rot Fungus and Performance of Biological Chemi-mechanical Pulping [J]. Chemistry and Industry of Forest Products, 2022, 42(6): 91-98. |
[9] | Hao ZHENG, Jinghui ZHOU, Yao LI. Preparation and Application of Biomass-based Carbon Aerogel as Electrodes for Supercapacitors [J]. Chemistry and Industry of Forest Products, 2022, 42(5): 76-82. |
[10] | Guangliu XU, Zhichen ZHAO, Rui ZHANG, Han ZHANG, Junjun ZHU. Fractionation of Bamboo Residues by Acid Hydrotrope [J]. Chemistry and Industry of Forest Products, 2022, 42(4): 16-24. |
[11] | Ying WANG, Bang AN, Mingcong XU, Jinquan YUE, Shouxin LIU, Wei LI. Synthesis of Blue and Green Lignin-based Luminescent Carbon Dots by Hydrothermal-Nitric Acid Oxidation [J]. Chemistry and Industry of Forest Products, 2022, 42(4): 33-39. |
[12] | Hui ZHAO, Yanru XU, Hao REN. Application Performance Comparison of Lignin-based Phenolic Resin with High Phenol Substitution Rate in Plywood [J]. Chemistry and Industry of Forest Products, 2022, 42(4): 75-80. |
[13] | Wenxiang ZHU, Fangeng CHEN, Tian HE, Yuhui SU, Yunsi LIU. Preparation of Pesticide Dispersant from Acetic Acid Lignin and Performance Evaluation [J]. Chemistry and Industry of Forest Products, 2022, 42(3): 19-26. |
[14] | Yifei DU, Yue PU, Liping ZHANG, Qiang ZHAO, Xianliang SONG. Power Generation Performance of Lignin in Direct Biomass Fuel Cell [J]. Chemistry and Industry of Forest Products, 2022, 42(3): 75-82. |
[15] | Qi GUO, Wei XU, Junli LIU. Preparation and Electrochemical Performance of Lignin-based Activated Carbon by Phosphoric Acid Activation [J]. Chemistry and Industry of Forest Products, 2022, 42(2): 31-38. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||