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Metal Porphyrin ¦Â-structural Modification Of The Catalytic Air Oxidation Of Cyclohexane

Posted on:2010-12-02Degree:MasterType:Thesis
Country:ChinaCandidate:Y TangFull Text:PDF
GTID:2191360275998503Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
Porphyrin derivatives are a class of cyclotetrapyrrolic compounds, which have 18~22 conjugated electrons. These derivatives have been used in various fields due to their unique structure and properties. Deuteroporphyrins are one of the key intermediates which are synthesized from protoporphyrin. The high accessibility of deuteroporphyrins together with its excellent stability and the close relationship to the naturally occurring haemes makes it an ideal compound to mimic enzymatic systems. In that context, they have well foreground for further development and application.One of important application of metallo-deuteroporphyrins is used as biomimetic catalyst in oxidation. Cyclohexanol and cyclohexanone are important organic intermediates; therefore, the development of their new synthesis process has always been the focus of academies and enterprises. Metallo-deuteroporphyrins can imitate cytochrome P-450 in the oxidation of cyclohexane with air and have a lot of excellencies.In this dissertation, the general work in this text can be summed up to two points:1. Modification atβ-sites of metallo-deuteroporphyrins. Four kinds of deuteroporphyrins and their metal complexes have been synthesized, metallo-deuteroporphyrin dimethyl ester, metallo-deuteroporphyrin diproyl ester and metallo-deuteroporphyrin dihexanyl ester were synthesized by esterification. Another kind is metallo-deuteroporphyrin dimethyl ester substituted with nitro-groups in 3-/8-sites at the macrocycle. All of these compounds have also been demonstrated by ESI-MS, FT-IR and ~1H-NMR.2. Metallo-deuteroporphyrin catalysed the oxidate of cyclohexane with air. Following with the experiment which the predecessor have done, we adopted the same reaction conditions in the experiment of the cyclohexane oxidation with air. The catalytic activity of metallo-deuteroporphyrins have been investigated. Cobalt deuteroporphyrins exhibited the highest catalytic activity in the experiments, and porphyrins substituted with electron-withdrawing groups are more efficient than the unsubstituted ones.
Keywords/Search Tags:Metallo-deuteroporphyrins, Modification, Cyclohexane, catalytic oxidation, air
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