Dissertation > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of heterocyclic compounds

Study on the Synthetic Method of a New 1H-1, 2, 3 Triazole Analogue

Author ChengKang
Tutor LiHuiPing
School Zhengzhou University
Course Chemical processes
Keywords 1H-1, 2,3 - triazole Click synthetic Proton exchange membrane Siloxane
Type Master's thesis
Year 2010
Downloads 134
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The proton exchange membrane is one of the core components of the PEM fuel cell. Current common perfluorosulfonic acid membrane having a high proton conductivity, but the proton conductivity mechanism determines the perfluorosulfonic acid membrane at low temperatures, high relative humidity shows functional. Resulting in catalyst easy CO poisoning, the system of water and heat management problem, in addition to high prices, high fuel permeability limit further promote the use of. The azole molecule due to the presence of protoplasts promoter has good proton conductivity, and the the conjugated structure within its ring, can form a class of chemical and electrochemical properties of a relatively stable compound. For this reason, as Zhengzhou University Graduate Scientific Research Fund (A192), 1H-1, 2,3 - three triazole represented by 4 - methoxy-benzyl alcohol as raw materials, chlorinated, azide substitution and prepared in the cycloaddition reaction to obtain a proton conductor of 1 - (4 - methoxy-benzyl) -4 - (hydroxymethyl) -1,2,3 - triazole, can be used for the preparation of novel polymer electrolyte membrane. The study has important academic significance and prospects for engineering applications. First synthesized a novel triazole-containing functional monomers as the preparation of proton exchange membrane precursor. Anisic methanol synthesis of raw materials by chloro substituted p-methoxybenzyl chloride (Ⅰ, yield 90.1%), and then by azide synthesis of organic azides 1 - (azidomethyl) -4 - anisole (AMOB) (Ⅱ, 93% yield), FTIR and NMR and its structure was identified. Secondly, organic azides (AMOB), and propargyl alcohol as raw materials, ascorbic acid and copper sulfate of Cu as a catalyst, by the \methoxy-benzyl) -4 - (hydroxymethyl) -1,2,3 - three triazole (Ⅲ, HTZMOB), and the optimum conditions are obtained through orthogonal test: reaction time will always be 41h; reaction temperature of 70 ° C; The material ratio of n (propargyl alcohol): n (AMOB) = 1.1:1, the ratio of copper sulfate and ascorbic acid (molar ratio) 1%: 5%, yield of 86.7% under this condition. Finally, the use of chloropropyl methyl dimethoxy silane coupling agent with the product HTZMOB graft Synthesis of 1 - (4 - benzyloxy) -4 - (2 - (3 - (dimethoxy (A -yl) silyl) propoxy) ethyl)-1H-1, 2,3 - triaza oxazole (Ⅳ, yield 93.8%). And using trifluoroacetic acid protecting group, the removal of the finally obtained 4 - (2 - (3 - (dimethoxy (methyl) silyl) propoxy) ethyl)-1H-1, 2,3 - triazole (V, yield 92.3%).

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