生物基聚酯单体的定向催化制备

doi:10.6023/A22110459

化学学报 ›› 2023, Vol. 81 ›› Issue (2): 175-190.DOI: 10.6023/A22110459 上一篇下一篇

综述

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

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摘要/Abstract

有机二羧酸是重要的聚酯单体, 广泛应用于化学纤维、轻工、电子等工业生产的各个方面. 随着社会工业化的发展, 以大量不可再生的石油资源为原料生产有机酸造成地球石油资源的匮乏和环境污染问题. 通过生物质及其衍生物来制备高附加值化学品有机二羧酸, 引起了化工应用领域的广泛关注. 在合成生物质有机二羧酸的研究中, 设计与制备具有高活性、高稳定性的催化剂具有重要意义. 近年来, 许多工作对催化剂的种类进行了探索, 并取得了一定的研究进展. 本文重点从生物质原料、催化剂性能评估、反应机理等方面对制备C₃~C₆二羧酸的催化体系进行了综述, 包括丙二酸、丁二酸、2,5-呋喃二甲酸和己二酸, 并对生物质有机二羧酸制备领域的发展进行了展望.

关键词: 生物质, 氧化反应, 有机二羧酸, 多相催化

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

引用此文

于璐瑶, 任祯, 杨宇森, 卫敏. 生物基聚酯单体的定向催化制备[J]. 化学学报, 2023, 81(2): 175-190.

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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图/表 10

图1. 由生物质衍生物生产的二羧酸

Figure 1. Dicarboxylic acids produced from biomass derivatives

图2. 纤维素在均匀水溶液中通过碱性水热反应生成丙二酸、乳酸、甲酸和乙酸的机理[28]

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]

图3. (a) H2O2存在下固体酸催化剂上糠醛制备丁二酸的反应机理. (b) 含N的聚苯并噁嗪(PBZ)基磺化碳催化剂的结构和(c) 在含N官能团的磺化碳催化剂上将糠醛转化为丁二酸[40]

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]

图4. (a) HBeta-38、DeAl-Beta和2Sn-Beta的吡啶吸附红外光谱. BA、LA和HB分别表示由Br?nsted酸性、Lewis酸性和氢键吡啶引起的峰值. (b) 不同催化剂对糠醛氧化反应的催化活性. 反应条件: 1 mmol (96 mg)糠醛, 50 mg催化剂, 10 mL 15% (w) H2O2溶液, 50 ℃, 6 h. (c) 糠醛吸附在各种催化剂上的DRIFTS. (d) UV-Vis谱显示在TS-1上存在H2O2时形成M-OOH物种[32].

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]

图5. (a) H2WO4催化LA转化为SA的机理[45]. (b) D216O、18O2 和H218O存在下LA催化有氧氧化的同位素示踪实验. (c) PBS-CA样品的应力-应变曲线. 插图显示了PBS-CA样品断裂点处的应变作为BS单元组成比的函数[46]

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]

图6. (a) 生物质合成己二酸的路径. (b) 从KA油制备己二酸的常规工艺[56]. (c) Dawson POM合成的连续步骤[57]. (d) 纳米簇的橡岭热椭球图(Oak Ridge thermal ellipsoid plot, ORTEP) (30%概率椭球体)[58]

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]

图7. (a) HMF氧化为FDCA的一般反应路径. (b) HMF氧化为FDCA的可能机理. (c) HMF及其缩醛衍生物(PD-HMF、EGHMF和MeO-HMF)在473 K下的稳定性. 将这些化合物置于耐压NMR管中, 并在298 K下抽空2 h以去除水污染. 将管密封, 然后在473 K下加热2 h. 使用苯甲酸作为内标物, 通过1H NMR分析测定这些化合物的物质的量损失. (d) 缩醛生成的反应能计算. (e) PD-HMF在Au/CeO2催化剂上氧化成FDCA过程中决速步的反应能量计算图[96]

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]

图8. (a) Pt纳米晶体Pt 4f的高分辨XPS光谱. 在(b) 水和(c) 甲醇中, 通入O2 (50 mL/min) 10 min后, 在Pt-NCs和Pt-NOs上与DMPO的自由基加合物的EPR光谱. (d) 提出了活性氧物种促进Pt(100)和Pt(111)表面上HMF氧化的醇氧化步骤的脱氢机理[97]

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]

图9. (a) Co-N-C-9.6的EXAFS谱. (b) 不同浓度Co-N-C-9.6的HMF的浓度变化1H NMR谱和HMF具有X受体的氢键模型. (c) 具有不同浓度吡啶的HMF的局部放大1H NMR谱(400 MHz, CDCl3). (d) Co-N-C-n催化剂上HMF氧化的表观速率常数k (d, 左)和TOF值(d, 中)之间的线性关系, 以及HMF和Co-N-C-n (d, 右)催化剂的–ΔG0与催化剂的氮含量之间的关系[105]

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]

图10. (a) MnO2的结构. 粉色、绿色和红色球体分别代表Mn、K和O原子. (b) MnO2的SEM图像[106]. (c) 在Co3O4/Mn0.2Co催化剂上HMF有氧无碱氧化成FDCA的合理反应机理[109]

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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