Decomposition of β-O-4 Linked Lignin Model Compound in Anhydrous Ethanol without any Added Catalyst
Xuezhong Wu,
Wenqian Jiao,
Yanming Li,
Bing-Zheng Li,
Yanghuan Huang,
Hongbin Zhang,
Yahong Zhang,
Quanrui Wang,
Yi Tang
Affiliations
Xuezhong Wu
Department of Chemistry, Laboratory of Advanced Materials, Collaborative Innovation Center of Chemistry for Energy Materials and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai, 200433, China; State Key Laboratory of Non-Food Biomass Enzyme Technology, National Engineering Research Center for Non-Food Biorefinery, Guangxi Key Laboratory of Biorefinery, Guangxi Academy of Sciences, Nanning, 530007, China; China
Wenqian Jiao
Department of Chemistry, Laboratory of Advanced Materials, Collaborative Innovation Center of Chemistry for Energy Materials and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai, 200433, China; China
Yanming Li
State Key Laboratory of Non-Food Biomass Enzyme Technology, National Engineering Research Center for Non-Food Biorefinery, Guangxi Key Laboratory of Biorefinery, Guangxi Academy of Sciences, Nanning, 530007, China; China
Bing-Zheng Li
State Key Laboratory of Non-Food Biomass Enzyme Technology, National Engineering Research Center for Non-Food Biorefinery, Guangxi Key Laboratory of Biorefinery, Guangxi Academy of Sciences, Nanning, 530007, China; China
Yanghuan Huang
Department of Chemistry, Laboratory of Advanced Materials, Collaborative Innovation Center of Chemistry for Energy Materials and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai, 200433, China; China
Hongbin Zhang
Department of Chemistry, Laboratory of Advanced Materials, Collaborative Innovation Center of Chemistry for Energy Materials and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai, 200433, China; China
Yahong Zhang
Department of Chemistry, Laboratory of Advanced Materials, Collaborative Innovation Center of Chemistry for Energy Materials and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai, 200433, China; China
Quanrui Wang
Department of Chemistry, Fudan University, Shanghai, 200433, China; China
Yi Tang
Department of Chemistry, Laboratory of Advanced Materials, Collaborative Innovation Center of Chemistry for Energy Materials and Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai, 200433, China; China
The cleavage of a lignin model compound of 2-phenoxyacetophenone (2-PAP) was studied in an anhydrous ethanol solvent. A high conversion of 2-PAP (> 99%) to the desired products (> 80% for phenol) with impressive selectivity was achieved in a stainless steel (T316SS) autoclave without any added catalyst. The stainless steel was analyzed as being effective at catalyzing the decomposition of 2-PAP because of its hydrogen transfer activity and stabilization of reaction intermediates, while anhydrous ethanol served as both a solvent and hydrogen donator. An active hydrogen-promoted reaction network was proposed to explain these results. Further investigation demonstrated that the co-catalyst, Cs2.5H0.5PMo12O40, enhanced the cleavage efficiency, which resulted in high yields of the desired products (> 98% of phenol and > 91% of acetophenone). The proposed method in this study based on the stainless steel-promoted hydrogen transfer reaction, which had the merits of a high conversion efficiency and easy handling, can be expected to develop a promising process for further transformation of lignin to valuable multi-substituted aromatics.
