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Studies on the Electrochemical Oxidation Cyanation to Synthesis α-Aminonitriles

Author: ZhaoPing
Tutor: YinYingWu
School: Tsinghua University
Course: Chemistry
Keywords: anodic oxidation organic electrochemistry synthesis α-aminonitrile synthesis electrolysis cyanation
CLC: TQ226.7
Type: PhD thesis
Year: 2004
Downloads: 161
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Abstract


The factors effected the industrialization of the organic electrochemistry were studied in this dissertation. The different amines were chosen as reaction model to synthesis α-aminonitriles and the rules of different factors in the electrolysis oxidation were summarized. The most apporopriate technical condition was found.The piperidine and its ramification selected as raw material to synthesis α-aminonitriles were studied in detail firstly. The oxidation potentials of the amines were determined through the liner sweep voltammetry study. The relationship between oxidation potential and chemical shift of 1H NMR was discovered firstly. The effects of the electrolysis manners, constant cell voltage, constant current and potentiostatic electrolysis, on the electrolysis were comparative studied. It was found that a series of complicated byproducts was found in constant current electrolysis becuase of the overoxidation caused by the polarization of the anode. Large numbers of organic substrates could not convert to α-aminonitriles under low constant cell voltage electrolysis or α-aminonitriles were overoxidized under high cell voltage electrolysis. High yield of α-aminonitriles could be obtained under potentiostatic electrolysis. The in situ products mixture of the three electrolytic manners were analyzed through GC-MS, the rules of various factors effect on the electrolysis were found, the best technical conditions were determined and the most reasonable mechanism of various condition electrolysis was proposed. The electrolysis condition such as electrolysis current, anodic potential, temperature, substrate concentration, solvent, electrolytes, solvent ratio, charges and material of electrode were studied and optimized and the simulative industrialized experiments were also studied. Thus the best condition for synthesis α-aminonitrile was found and made it is possible to industrialize. Appropriate anodic potential (not constant current and constant cell voltage) is the key factor to enhance the yield of the α-aminonitrile. Only α-aminonitriles could be obtained when the appropriate electrolysis condition was selected. <WP=5>The synthesis of α-aminonitriles from α-amino ester, carbamate and piperidine was experimented firstly in this paper. The oxidation potential of carbamate was too high to be as raw material to synthesis α-aminonitrile. The synthetical steps were simplified and it is valuable to industrialize when piperidine was selected as substrate to synthesize α-aminonitrile. The systematic investigative methods were proposed and the hindrances of the industrialization of organic electrochemistry were found. The key factors that effect on the industrialization of the organic electrochemistry and the measures and schemes to solve were proposed. The series of the conclusions in the dissertation must be useful and have instruction significance to the organic electrochemistry synthesis and its industrialization.

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of aliphatic compounds ( acyclic compounds) > Aliphatic nitrogen-containing compounds
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