Application of niobium oxide supported copper catalyst in synthesis of secondary amine or derivative thereof from aromatic nitro compound and benzyl alcohol compound

By using Cu/Nb2O5 catalyst to catalyze the formation of secondary amines with aromatic nitroates and benzyl alcohol compounds under hydrogen conditions, the problems of by-product generation, separation and dependence of precious metal catalysts in the prior art are solved, and efficient, environmentally friendly and low-cost secondary amine synthesis is achieved.

CN119701982APending Publication Date: 2025-03-28LANZHOU UNIV
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Patent Information

Application Number
CN202411893133.6
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-12-20
Publication Date
2025-03-28

AI Technical Summary

Technical Problem

The existing secondary amine synthesis methods have problems such as by-product generation and separation, great environmental impact and dependence on expensive precious metal catalysts, making it difficult to achieve environmentally friendly, efficient and low-cost synthesis.

Method used

The Cu/Nb2O5 catalyst is prepared by hydrothermal method, precipitation method and hydrogen calcination, and is used to catalyze the formation of secondary amines or derivatives of aromatic nitro compounds and benzyl alcohol compounds under hydrogen conditions to achieve atomic economical synthesis.

Benefits of technology

The synthesis of secondary amines with low cost, high economicality and high yield is achieved, which avoids the problem of excessive benzyl alcohol, simplifies product separation, and has good industrial production potential.

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to application of a niobium oxide supported copper catalyst in preparation of secondary amine and derivatives thereof from an aromatic nitro compound and a benzyl alcohol compound. The invention finds that niobium oxide loaded copper (Cu / Nb2O5) can be used as a catalyst, an aromatic nitro compound and a benzyl alcohol compound are used as raw materials, hydrogen is used as a reaction atmosphere, and four steps of nitro hydrogenation, alcohol dehydrogenation, aldehyde amine coupling and imine hydrogenation are completed by a one-pot method to synthesize secondary amine or derivatives thereof. The niobium oxide supported copper catalyst has the capabilities of catalyzing nitro hydrogenation, alcohol dehydrogenation, aldehyde-amine coupling and imine hydrogenation at the same time, atom economical synthesis of an aromatic nitro compound and a benzyl alcohol compound in an equal molar ratio is achieved, and the niobium oxide supported copper catalyst is superior to found noble metal or non-noble metal catalysts. The niobium oxide supported copper catalyst is prepared from niobium oxalate and copper nitrate through a hydrothermal method, a precipitation method and hydrogen roasting, and the preparation process is simple and economical; according to the method, hydrogen is adopted as a hydrogen source, excessive use of benzyl alcohol compounds is avoided, atom economical synthesis of secondary amine from aromatic nitro compounds and benzyl alcohol compounds is innovatively realized, and the separation and purification difficulty is remarkably reduced. The catalytic system has the advantages of low catalyst cost, excellent yield, good stability, high reaction atom economy and the like, and has good industrial production potential.
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