Directed Preparation of Biomass-based Polyester Monomers by Catalytic Conversion

doi:10.6023/A22110459

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (2): 175-190.DOI: 10.6023/A22110459 Previous Articles Next Articles

Review

生物基聚酯单体的定向催化制备

于璐瑶, 任祯, 杨宇森^*(), 卫敏

北京化工大学化学学院化工资源有效利用国家重点实验室北京 100029

投稿日期:2022-11-12 发布日期:2022-12-19
通讯作者: 杨宇森

作者简介:

于璐瑶, 北京化工大学在读研究生, 2022年6月于北京化工大学化学工程学院化学工程与工艺专业获得学士学位, 随后加入北京化工大学化工资源有效利用国家重点实验室卫敏教授课题组, 主要研究方向为生物质有机酸的定向制备.

杨宇森, 博士, 副教授, 硕士生导师. 2019年于北京化工大学获得化学工程与技术博士学位, 师从卫敏教授. 2019年至今在北京化工大学化工资源有效利用国家重点实验室从事多相催化研究, 主要研究方向: (1) 生物质平台分子的定向催化转化; (2) 可再生资源途径制氢、氢气精制与高效利用. 目前, 已发表SCI研究论文40余篇. 以第一(含共一)作者和共同通讯作者在Nat. Commun.、ACS Catal.、Chem Catal.、Appl. Catal. B: Environ.、J. Catal.、Green Chem.、《化学学报》及《化工学报》等期刊发表学术论文29篇(其中IF>10的17篇), 他引1000余次. 参与编写专著1部, 授权国家发明专利1项, 获中国石油和化学工业联合会科技进步二等奖1项(2022年).

卫敏, 教授, 博士生导师. 2001年于北京大学获得理学博士学位, 同年加入北京化工大学, 2006年晋升为教授. 2008年佐治亚理工学院访问学者. 近年来从事一碳化学、能源催化、生物质催化转化研究工作. 以通讯作者在Nat. Commun.、J. Am. Chem. Soc.、Angew. Chem. Int. Ed.等刊物发表SCI收录研究论文200余篇; 发表论文他引12600余次, 16篇论文入选基本科学指标数据库ESI高被引TOP 1%论文. 授权国际专利2项, 授权国家发明专利30余项. 现担任Science Bulletin期刊副主编, 催化学报编委, 中国化学会高级会员, 英国皇家化学会会士. 获2012年国家杰出青年基金资助; 获2015年中国石油和化学工业联合会科技进步一等奖; 入选2017年国家百千万人才工程, 被授予“有突出贡献中青年专家”称号; 获2019年第十五届中国青年科技奖.

基金资助:
国家自然科学基金(22172006); 国家自然科学基金(21521005); 国家自然科学基金(22102006); 国家重点研发计划(2021YFC2103500); 北京市自然科学基金(2212012); 中央高校基本科研业务费(XK1803-05); 中国石化分子化学工程联合研发中心项目资助.

Directed Preparation of Biomass-based Polyester Monomers by Catalytic Conversion

Luyao Yu, Zhen Ren, Yusen Yang(), Min Wei

State Key Laboratory of Chemical Resource Engineering, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029

Received:2022-11-12 Published:2022-12-19
Contact: Yusen Yang
Supported by:
National Natural Science Foundation of China(22172006); National Natural Science Foundation of China(21521005); National Natural Science Foundation of China(22102006); National Key Research and Development Program(2021YFC2103500); Beijing Natural Science Foundation(2212012); Fundamental Research Funds for the Central Universities(XK1803-05); Joint Research and Development Center of Molecular Chemical Engineering of SINOPEC

Dicarboxylic acid is an important polyester monomer, which is widely used in all aspects of chemical fiber, light industry, electronics and other industrial production. With the development of social industrialization, the production of dicarboxylic acids from a large number of non-renewable petroleum resources has caused the lack of oil resources and environmental pollution of the earth. The preparation of high value-added chemicals dicarboxylic acids by biomass and its derivatives has attracted extensive attention in chemical applications. In the research of synthetic biomass dicarboxylic acid, it is of great significance to design and prepare catalysts with high activity and high stability. In recent years, many works have explored the types of catalysts and made certain research progress. In this review, the catalytic system for the preparation of C₃~C₆ dicarboxylic acid, including malonic acid, succinic acid, 2,5-furandicarboxylic acid and adipic acid, was reviewed from the aspects of biomass raw materials, catalyst performance evaluation and reaction mechanism, and the development of biomass dicarboxylic acid preparation is prospected.

Key words: biomass, oxidation reaction, dicarboxylic acid, heterogeneous catalysis

Cite this article

Luyao Yu, Zhen Ren, Yusen Yang, Min Wei. Directed Preparation of Biomass-based Polyester Monomers by Catalytic Conversion[J]. Acta Chimica Sinica, 2023, 81(2): 175-190.

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Fig. & Tab. 10

Figure 1. Dicarboxylic acids produced from biomass derivatives

Figure 2. Proposed mechanism for the formation of malonic acid, lactic acid, formic acid, and acetic acid from cellulose by an alkaline hydrothermal reaction in its homogeneously aqueous solution[28]

Figure 3. (a) Proposed reaction mechanism for SA production from furfural over solid acid catalysts in the presence of H2O2. (b) Structure of SO3H-carbocatalyst with nitrogen functionalities based on polybenzoxazine and (c) furfural transformation towards succinic acid over SO3H-carbocatalyst with nitrogen functionalities[40]

Figure 4. (a) Pyridine adsorption IR spectra for HBeta-38, DeAl-Beta, and 2Sn-Beta. BA, LA, and HB indicate peaks due to Br?nsted acidity, Lewis acidity, and hydrogen-bonded pyridine, respectively. (b) Catalytic activity of different catalysts for the furfural oxidation reaction. Reaction conditions: 1 mmol (96 mg) furfural, 50 mg of the catalyst, 10 mL of the 15% (w) H2O2 solution, 50 ℃, 6 h. (c) DRIFTS spectra of furfural adsorbed on various catalysts. (d) UV-Vis spectra of catalysts showing formation of M-OOH species in the presence of H2O2 on TS-1[32]

Figure 5. (a) Mechanism of LA transformation to SA catalyzed by H2WO4[45]. (b) Isotropic tracing experiments on the catalytic aerobic oxidation of LA in the presence of D216O, 18O2 and H218O. (c) Stress-strain curves for PBS-CA samples. The inset shows the strain at the breaking point of PBS-CA samples as a function of the composition ratio of the BS unit[46]

Figure 6. (a) Routes for the synthesis of adipic acid from biomass. (b) Conventional process for the manufacture of adipic acid from KA oil[56]. (c) Successive steps of Dawson POM synthesis[57]. (d) ORTEP drawing of nanocluster (30% probability ellipsoid)[58]

Figure 7. (a) General reaction pathways for HMF oxidation to FDCA. (b) Proposed Mechanism for HMF oxidation to FDCA. (c) Stability of HMF and its acetal derivatives (PD-HMF, EG-HMF, and MeO-HMF) at 473 K. These compounds were placed in a pressure-resistance NMR tube and evacuated at 298 K for 2 h to remove water contamination. The tubes were sealed and then heated at 473 K for 2 h. The molar loss of these compounds was determined by 1H NMR analysis using benzoic acid as an internal standard. (d) Computed reaction energies of the acetal formation. (e) Computed reaction energy diagram for the rate-determining step during the oxidation of PD-HMF into FDCA over the CeO2-supported Au catalyst[96]

Figure 8. (a) High-resolution XPS spectra of Pt nanocrystals in the Pt 4f. EPR spectra of radical adducts with DMPO over Pt-NCs and Pt-NOs after O2 bubbling (50 mL/min) for 10 min at 40 ℃ in (b) aqueous and (c) methanol dispersions. (d) Proposed active oxygen species promoted dehydrogenation mechanism for the alcohol oxidation step of HMF oxidation on the surfaces of Pt(100) and Pt(111)[97]

Figure 9. (a) EXAFS spectra of Co-N-C-9.6. (b) Concentration-variation 1H NMR spectra of HMF with different concentrations of Co-N-C-9.6 and the model of hydrogen bonded HMF with an acceptor of X. (c) Locally amplified 1H NMR spectra of HMF with different concentrations of pyridine (400 MHz, CDCl3). (d) Linear relationships between the apparent rate constants k (d, left) and TOF values (d, middle) of HMF oxidation over Co-N-C-n catalysts, together with the –ΔG0 for HMF and Co-N-C-n catalysts (d, right) with nitrogen contents of catalysts[105]

Figure 10. (a) Structures of MnO2. Pink, green, and red spheres represent Mn, K, and O atoms, respectively. (b) SEM images of MnO2[106]. (c) Plausible reaction mechanism of the aerobic base-free oxidation of HMF to FDCA over the Co3O4/Mn0.2Co catalyst[109]

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生物基聚酯单体的定向催化制备

Directed Preparation of Biomass-based Polyester Monomers by Catalytic Conversion

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