期刊
CHEMSUSCHEM
卷 15, 期 18, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202200914
关键词
amines; catalytic amination; cyclohexylamines; reductive catalytic fractionation; sustainable chemistry
资金
- European Research Council, ERC [638076]
- ERC [875649]
- Netherlands Organization for Scientific Research (NWO) [723.015.005]
- China Scholarship Council [201808330391]
- European Research Council (ERC) [875649] Funding Source: European Research Council (ERC)
Cyclic primary amines are important building blocks in many chemicals and pharmaceuticals. A powerful catalytic strategy was developed to convert guaiacol into cyclohexylamine with high yield. The method can also be applied to other types of guaiacols. It was found that crude bio-oil from birch lignocellulose can be transformed into a product mixture rich in 4-propylcyclohexylamine.
Cyclic primary amines are elementary building blocks to many fine chemicals, pharmaceuticals, and polymers. Here, a powerful one-pot Raney Ni-based catalytic strategy was developed to transform guaiacol into cyclohexylamine using NH3 (7 bar) and H-2 (10 bar) in up to 94 % yield. The methodology was extendable to the conversion of a wider range of guaiacols and syringols into their corresponding cyclohexylamines. Notably, a crude bio-oil originating from the reductive catalytic fractionation of birch lignocellulose was transformed into a product mixture rich in 4-propylcyclohexylamine, constituting an interesting case of catalytic funneling. The isolated yield of the desired 4-propylcyclohexylamine reached as high as 7 wt % (on lignin basis). Preliminary mechanistic studies pointed at the consecutive occurrence of three key catalytic transformations, namely, demethoxylation, hydrogenation, and amination.
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