木质素及其衍生物负载金属催化剂在有机合成中的应用研究进展

doi:10.6023/cjoc202207013

摘要/Abstract

碳中和发展理念的提出使得生物质基催化剂的关注度不断提高, 将木质素作为过渡金属催化剂的载体来制备非均相催化剂应用于有机合成领域, 可以极大地提高木质素的利用价值. 木质素结构中广泛存在的含氧官能团为金属催化剂的负载提供了多种结合位点, 通过物理吸附/沉积、离子交换以及与羟基官能团通过静电络合可以有效地捕获金属粒子. 首先介绍了木质素的结构, 然后介绍了制备非均相催化剂的方法, 重点介绍了木质素及其衍生物负载金属催化剂催化点击反应、Glaser反应、Huisgen [3＋2]环加成反应、Heck反应、Suzuki反应、Sonogashira反应、Stille偶联反应、迈克尔加成/脱水串联反应、亲电开环反应、Fridel-Crafts型反应及乙烯聚合反应等, 并对存在的问题和发展趋势进行了展望.

关键词: 功能化木质素, 木质素负载金属催化剂, 非均相催化, 有机合成, 绿色化学

The attention of biomass-based catalysts has been continuously increased due to the proposal of carbon neutralization development concept. The use of lignin as a support for transition metal catalysts for the preparation of heterogeneous catalysts in the field of organic synthesis can greatly improve the utilization value of lignin. The extensive presence of oxygen-containing functionalities in the lignin structure provides a variety of binding sites for the loading of metal catalysts, and metal particles can be efficiently captured by physical adsorption/deposition, ion exchange, and electrostatic complexation with hydroxyl functional groups. The structure of lignin is firstly introduced, and the methods for preparing heterogeneous catalysts are then described. Lignin and its derivatives supported metal catalysts catalyzed Click reaction, Glaser reaction, Huisgen [3＋2] cycloaddition reaction, Heck reaction, Suzuki reaction, Sonogashira reaction, Stille coupling, Michael addition/dehydration tandem, Electrophilic ring-opening reaction, Fridel-Crafts type reaction, ethylene polymerization and other reactions. Thus, at the end of this review, the existing problems and development trends are prospected.

Key words: functionalized lignin, lignin-supported metal catalyst, heterogeneous catalysis, organic synthesis, green chemistry

引用此文

莫百川, 陈春霞, 彭进松. 木质素及其衍生物负载金属催化剂在有机合成中的应用研究进展[J]. 有机化学, 2023, 43(4): 1215-1240.

Baichuan Mo, Chunxia Chen, Jinsong Peng. Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1215-1240.

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图/表 44

图1. 木质素的结构单元

Figure 1. Structural unit of lignin

图2. 木质素的代表结构

Figure 2. Representative structures of lignin

名称	提取流程	特征
硫酸盐木质素	Na₂S/NaOH	高度修饰, 部分碎片化
木质素磺酸盐	从软木材硫酸盐制浆工艺的废液中提取木质素	高度修饰, 高平均分子量, 醚键断裂, 甲氧基裂解且会形成新的碳-碳键
磨木质素(MWL)	球磨后用二氧六环和水混合溶剂提取	最接近天然结构, 多次球磨可能导致部分解聚
有机溶剂木质素	直接用有机溶剂提取木质素	条件温和, 木质素收率高, 可以回收有机溶剂
离子液体木质素	逐步沉淀或选择性提取	与硫酸盐木质素比结构改变更小, 分子量分布更均匀
蒸汽爆破木质素	对纤维进行高温蒸汽爆破	不需要或需要很少的化学试剂, 能耗低, 处理时间短, 只改变某些特定的官能团
碱性木质素	在碱性条件下处理木质素	通过β-O-4断裂进行部分降解

表1. 木质素衍生物的提取方式及特点

Table 1. Extraction methods and characteristics of lignin derivatives

图式1. DIS@SLS-TMEDA-Cu催化剂的制备

Scheme 1. Preparation of DIS@SLS-TMEDA-Cu catalyst

图式2. Cu2O@Lignin催化Huisgen [3＋2]环加成反应机理

Scheme 2. Mechanism for the Huisgen [3＋2] cycloaddition reaction catalyzed by Cu2O@Lignin

图式3. SLS-FAS-Cu催化剂的制备

Scheme 3. Preparation of SLS-FAS-Cu catalyst

图式4. 三维生物基质负载金属纳米粒子

Scheme 4. Metal nanoparticles supported on the three-dimensional biomass

污染物	还原率/%	时间/min
MO	99.5	4
MB	96.6	5
CR	95.1	7
AO	98.8	14
4-NP	96.8	10

表2. Cu-ZV-MNPs/EFB对污染物的催化还原性能

Table 2. Catalytic reduction performance of Cu-ZV-MNPs/EFB for pollutants

图式5. Cu(II)-SLS纳米花非均相催化剂的制备

Scheme 5. Preparation of Cu(II)-SLS nanoflowers heterogeneous catalyst

图式6. Fe3O4-Lignin-Cu 催化剂的制备

Scheme 6. Preparation of Fe3O4-Lignin-Cu NPs catalyst

图式7. Cu NPs@Fe3O4-LS-CS的合成示意图

Scheme 7. Synthesis of Cu NPs@Fe3O4-LS-CS catalyst

图式8. Cu NPs@Fe3O4-LS-CS催化合成5-芳基四唑的机理

Scheme 8. Mechanism of Cu NPs@Fe3O4-LS-CS catalyzed synthesis of 5-aryltetrazoles

图式9. Cu@MLS-TA的合成过程

Scheme 9. Synthesis process of Cu@MLS-TA

图式10. Cu@MLS-TA催化胺N-甲酰化反应机理

Scheme 10. Proposed mechanism for the N-formylation of amines catalyzed by Cu@MLS-TA

电极	电解液	法拉第效率/%
铜-木质素-泡沫镍	0.1 mol/L Na₂SO₄	23.20
铜-泡沫镍	0.1 mol/L Na₂SO₄	16.50
铜/N-参杂石墨烯	0.1 mol/L KHCO₃	63
铜网	0.5 mol/L KHCO₃	13
3D CuO	0.1 mol/L KHCO₃	13
Cu/TiO₂	0.2 mol/L KI	27.40
石墨烯/Cu₂O	0.5 mol/L NaHCO₃	9.93
Cu₄Zn	0.1 mol/L KHCO₃	29.10

表3. 不同催化剂电化学还原CO2的法拉第效率

Table 3. Faradaic efficiency of electrochemical reduction of CO2 with different catalysts

图3. (a)铜、(b)铜-泡沫镍、(c)铜-木质素和(d)铜-木质素-泡沫镍的扫描电子显微镜显微照片

Figure 3. Scanning electron microscope micrographs of (a) Cu, (b) Cu-Ni foam, (c) Cu-lignin and (d) Cu-lignin-Ni foam

图式11. 非均相催化剂Fe3O4@LigA/Cu的制备

Scheme 11. Preparation of heterogeneous Fe3O4@LigA/Cu catalyst

图式12. Fe3O4@LigA/Cu催化的还原反应

Scheme 12. Reduction reaction catalyzed by Fe3O4@LigA/Cu

Entry	Catalyst	Time/h
1	LAC-Pd	4
2	LACT-Pd	2
3	LAC-Pd	2
4	LACT-Pd	2
5	LACT-Pd	2
6	LACT-Pd	2
7	LACT-Pd	2
8	LACT-Pd	2
9	LACT-Pd	6

表4. LAC-Pd和LACT-Pd催化烯烃加氢a

Table 4. LAC-Pd and LACT-Pd catalyzed hydrogenation of alkenes

Entry	Arylbromide	Arylboronic acid	Cross-coupling	Homo-coupling
1
2				Not detected
3				Not detected

表5. LACT-Pd催化Suzuki-Miyaura偶联反应

Table 5. LACT-Pd catalyzed Suzuki-Miyaura coupling reaction

图式13. 3种非均相催化剂的制备

Scheme 13. Preparation of three heterogeneous catalysts

图式14. Lignin-TEPA-Pd催化剂的制备路线

Scheme 14. Preparation route of lignin-TEPA-Pd catalyst

图式15. Pd NPs@lignin催化剂的合成

Scheme 15. Synthesis of Pd NPs@lignin catalyst

图式16. Pd NPs@lignin催化Sonogashira偶联反应循环实验

Scheme 16. Cycling experiment of Sonogashira coupling reaction catalyzed by Pd NPs@lignin

图式17. FLA-Pd催化剂的合成

Scheme 17. Synthesis of FLA-Pd catalyst

图4. Pd NPs@Fe3O4-CLS结构示意图

Figure 4. Structural diagram of Pd NPs@Fe3O4-CLS

图式18. Pd NPs合成机制

Scheme 18. Proposed mechanism for synthesis of Pd NPs

图式19. Fe3O4-lignin@Pd NPs的合成

Scheme 19. Synthesis of Fe3O4-lignin@Pd NPs

图式20. Fe3O4-lignin@Pd NPs 催化Mizoroki-Heck机理

Scheme 20. Mechanism of Mizoroki-Heck reaction catalyzed by Fe3O4-lignin@Pd NPs

图式21. Pd@LPR催化剂的制备

Scheme 21. Preperation of Pd@LPR catalyst

图式22. FLT-Pd非均相催化剂的合成

Scheme 22. Synthesis of FLT-Pd heterogeneous catalyst

图式23. Ag/C的合成及Ag/C催化硝基苯酚还原

Scheme 23. Synthesis of Ag/C and Ag/C catalyzed reduction of nitrophenol

图式24. Ag@SLSPF催化剂的制备

Scheme 24. Preparation of Ag@SLSPF catalyst

图式25. 非均相催化剂SLS@Ag的制备

Scheme 25. Preparation of heterogeneous catalyst SLS@Ag

图式26. FeC催化剂的制备过程

Scheme 26. Preparation procedure of FeC catalyst

图式27. Fe@C催化生物合成气合成液态烃

Scheme 27. Fe@C catalyzed synthesis of liquid hydrocarbon from biosyngas

图式28. FeNi-CDL催化硝基苯和苯乙炔氢化还原

Scheme 28. FeNi-CDL catalyzed hydrogenation reduction of nitrobenzene and phenylacetylene

图式29. P-(L-FeTPP)的制备

Scheme 29. Preparation of P-(L-FeTPP)

图式30. Pt纳米粒子的制备及其对α-蒎烯催化加氢反应

Scheme 30. Preparation of Pt nanoparticles and their catalytic hydrogenation of α-pinene

图式31. 空心球形木质素负载钒基齐格勒-纳塔催化剂的制备及其在乙烯聚合中的应用

Scheme 31. Preparation of hollow spherical lignin-supported vanadium-based Ziegler-Natta catalyst and its application in ethylene polymerization

图式32. LCN@Zn-SAC的合成

Scheme 32. Synthesis of LCN@Zn-SAC

图式33. 去保护木质素负载钴(II)催化剂的制备

Scheme 33. Preparation of deprotected lignin-supported Co(II) catalyst

图式34. DL-CoTCPP催化HMF制备HMFCA和FDCA

Scheme 34. Preparation of HMFCA and FDCA from HMF catalyzed by DL-CoTCPP

图式35. 双功能木质素磺酸盐催化剂将纤维素降解为HMF和木聚糖降解为糠醛

Scheme 35. Degradation of cellulose to HMF and xylan to Furfural by bifunctional lignosulfonate catalysts

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