物理化学学报 >> 2023, Vol. 39 >> Issue (9): 2212065.doi: 10.3866/PKU.WHXB202212065

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均相催化剂催化氧气氧化生物质制备甲酸

侯玉翠1, 何卓森2, 任树行2, 吴卫泽2,*()   

  1. 1 太原师范学院化学与材料学院, 山西 晋中 030619
    2 北京化工大学化学工程学院, 化工资源有效利用国家重点实验室, 北京 100029
  • 收稿日期:2022-12-31 录用日期:2023-02-13 发布日期:2023-02-24
  • 通讯作者: 吴卫泽 E-mail:wzwu@mail.buct.edu.cn

Catalytic Oxidation of Biomass to Formic Acid under O2 with Homogeneous Catalysts

Yucui Hou1, Zhuosen He2, Shuhang Ren2, Weize Wu2,*()   

  1. 1 College of Chemistry and Materials, Taiyuan Normal University, Jinzhong 030619, Shanxi Province, China
    2 State Key Laboratory of Chemical Resource Engineering, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, China
  • Received:2022-12-31 Accepted:2023-02-13 Published:2023-02-24
  • Contact: Weize Wu E-mail:wzwu@mail.buct.edu.cn

摘要:

甲酸是一种重要的化工原料,以可再生生物质为原料,通过催化氧气氧化制备甲酸具有重要意义。对于不溶于水的生物质原料的转化,采用可溶于水的均相催化剂体系证明是有效的。本文总结了均相催化剂体系(包括含钒杂多酸、含钒杂多酸+H2SO4、含钒杂多酸基离子液体、NaVO3+H2SO4、VOSO4、NaVO3-FeCl3+H2SO4、FeCl3+H2SO4等)在催化氧气氧化生物质(包括生物质模型化合物、纤维素、木材、秸秆和玉米芯等)制备甲酸方面的研究,分析了其转化的过程和机理。最后,指出了目前催化氧化生物质制备甲酸存在的问题和挑战。

关键词: 甲酸, 生物质, 氧气, 催化氧化, 均相催化剂

Abstract:

Formic acid (FA) is an important chemical for the production of leathers, medicines, preservatives, rubbers, textiles, and other materials. FA is also used as H2 and CO carriers, and as a fuel in fuel cells. Although most commonly synthesized from fossil fuels, FA can also be obtained from more sustainable sources, such as biomass (e.g., straw, husk, and sawdust). Oxygen and air are affordable and easily available oxidants used for the oxidation of biomass to FA. Because solid biomass is not soluble in water or organic solvents, homogeneous catalysts are preferred for the catalytic oxidation of biomass to FA by O2 in water. It has been demonstrated that homogeneous catalysts, such as vanadium-containing heteropoly acids (HPA), HPA+H2SO4, NaVO3+H2SO4, HPA-containing ionic liquids, VOSO4, NaVO3-FeCl3+H2SO4, and FeCl3+H2SO4, can convert complex biomass substrates to FA with high atom economy using O2 as the oxidant. The reported biomass substrates include model compounds, cellulose, wood, straw, and corncobs. The reaction conditions were summarized to compare the biomass conversions and FA yields. Vanadium-containing catalysts had the highest FA yield at mild conditions (T ≤ 170 ºC and P(O2) ≤ 3 MPa). Both the reaction rate and FA yield were improved by adding H2SO4. This high conversion can be explained by an electron transfer and oxygen transfer (ET-OT) mechanism, where high-valence transition metals (V5+ or Fe3+) oxidize biomass to FA and are reduced to low-valence species (V4+ or Fe2+). The catalysts are then regenerated by O2. This reaction occurs through C2―C3 and/or C3―C4 bond cleavages via retro-aldol condensation, followed by continued C―C bond cleavages to form FA. Using isotope-labeled D-glucose as substrate, we determined that oxidation occurs via successive C1―C2 bond cleavages; a V5+ catalyst reacts with C1―C2 to form a five-membered ring complex, without C―H bond cleavages, followed by oxidation from another V5+ species to form FA. The oxidation of solid cellulose occurs through hydrolysis (hydrolysis of cellulose to monosaccharides, and deep hydrolysis of monosaccharides to levulinic acid) and oxidation (monosaccharides to FA and levulinic acid to acetic acid) reactions. The catalytic oxidation of monosaccharides and deep hydrolysis steps are competitive, and the reaction rate of the latter increases faster with increasing temperature. However, catalytic oxidation was favored by higher P(O2). The addition of methanol, ethanol and DMSO to the reaction system, and in situ extraction of FA were performed to inhibit CO2 formation. FA was separated by extraction and the catalyst system was reused. A continuous process for producing FA from molasses was established using a three-phase liquid-liquid-gas system with a reaction volume of 2 L. Finally, the limitations and future requirements of this oxidation reaction are discussed: (1) improving separation or in situ conversion of FA; (2) improving homogeneous catalysts for both biomass hydrolysis and catalytic oxidation to FA; (3) studying the impact of ash in biomass, particularly after catalyst reuse; and (4) understanding the mechanism through which organic solvents such as methanol inhibit CO2 formation.

Key words: Formic acid, Biomass, Oxygen, Catalytic oxidation, Homogeneous catalyst