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Selective valorization of lignin to phenol by direct transformation of Csp2-Csp3 and C-O bonds.

ABSTRACT: Phenol is an important commodity chemical in the industry, which is currently produced using fossil feedstocks. Here, we report a strategy to produce phenol from lignin by directly deconstructing Csp2-Csp3 and C-O bonds under mild conditions. It was found that zeolite catalyst could efficiently catalyze both the direct Csp2-Csp3 bond breakage to remove propyl structure and aliphatic ? carbon-oxygen (C?-O) bond hydrolysis to form OH group on the aromatic ring. The yield of phenol could reach 10.9 weight % with a selectivity of 91.8%. In this unique route, water was the only reactant besides lignin. A scale-up experiment showed that 4.1 g of pure phenol could be obtained from 50.0 g of lignin. The reaction pathway was proposed by a combination of control experiments and density functional theory studies. This work opens the way for producing phenol from lignin by direct transformation of Csp2-Csp3 and C-O bonds in lignin.

SUBMITTER: Yan J

PROVIDER: S-EPMC7673717 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Selective valorization of lignin to phenol by direct transformation of Csp2-Csp3 and C-O bonds.

Yan Jiang J Meng Qinglei Q Shen Xiaojun X Chen Bingfeng B Sun Yang Y Xiang Junfeng J Liu Huizhen H Han Buxing B

Science advances 20201106 45

Phenol is an important commodity chemical in the industry, which is currently produced using fossil feedstocks. Here, we report a strategy to produce phenol from lignin by directly deconstructing Csp2-Csp3 and C-O bonds under mild conditions. It was found that zeolite catalyst could efficiently catalyze both the direct Csp2-Csp3 bond breakage to remove propyl structure and aliphatic β carbon-oxygen (Cβ-O) bond hydrolysis to form OH group on ...[more]

PMID: 33158871

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Project description:Technical lignins produced as a by-product in biorefinery processes represent a potential source of renewable carbon. In consideration of the possibilities of the industrial transformation of this substrate into various valuable bio-based molecules, the biological deconstruction of a technical soda lignin by filamentous fungi was investigated. The ability of three basidiomycetes (Polyporus brumalis, Pycnoporus sanguineus and Leiotrametes menziesii) to modify this material, the resultant structural and chemical changes, and the secreted proteins during growth on this substrate were investigated. The three fungi could grow on the technical lignin alone, and the growth rate increased when the media were supplemented with glucose or maltose. The proteomic analysis of the culture supernatants after three days of growth revealed the secretion of numerous Carbohydrate-Active Enzymes (CAZymes). The secretomic profiles varied widely between the strains and the presence of technical lignin alone triggered the early secretion of many lignin-acting oxidoreductases. The secretomes were notably rich in glycoside hydrolases and H2O2-producing auxiliary activity enzymes with copper radical oxidases being induced on lignin for all strains. The lignin treatment by fungi modified both the soluble and insoluble lignin fractions. A significant decrease in the amount of soluble higher molar mass compounds was observed in the case of P. sanguineus. This strain was also responsible for the modification of the lower molar mass compounds of the lignin insoluble fraction and a 40% decrease in the thioacidolysis yield. The similarity in the activities of P. sanguineus and P. brumalis in modifying the functional groups of the technical lignin were observed, the results suggest that the lignin has undergone structural changes, or at least changes in its composition, and pave the route for the utilization of filamentous fungi to functionalize technical lignins and produce the enzymes of interest for biorefinery applications.

Dataset Information

Selective valorization of lignin to phenol by direct transformation of Csp2-Csp3 and C-O bonds.

Publications

Selective valorization of lignin to phenol by direct transformation of C<sub>sp2</sub>-C<sub>sp3</sub> and C-O bonds.

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