Synthesis of meso-TPP Revisited: Its "Green-Oriented" Optimization Under Controlled Microwave Heating

A practical and proecological improvement for synthesis of meso-tetraphenylporphyrin (meso-TPP) under microwave irradiation is described. A cyclocondensation reaction of benzaldehyde and pyrrole followed by oxidation of the porphyrinogen formed as an intermediate in a small amount of propionic acid...

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Bibliographic Details
Published in:Synthetic communications 2011-12, Vol.41 (24), p.3703-3713
Main Authors: Mikus, Agnieszka, Bielińska, Marta E., Lipińska, Teodozja, Ostrowski, Stanisław
Format: Article
Language:English
Subjects:
Green chemistry
microwave-assisted synthesis
optimization
porphyrins
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Summary:A practical and proecological improvement for synthesis of meso-tetraphenylporphyrin (meso-TPP) under microwave irradiation is described. A cyclocondensation reaction of benzaldehyde and pyrrole followed by oxidation of the porphyrinogen formed as an intermediate in a small amount of propionic acid at 120 °C (under controlled microwave heating) resulted in conversion to meso-TPP in a reasonable yield (ca. 30%) in preparative-scale experiments (300-500 mg). The influence of many parameters such as the concentration of reagents, catalyst, solvent, temperature, reaction time, and oxidant on the reaction yield was studied. The environmental motive in this improvement is reduction of solvent volume (ca. 250 times). Also, some toxic reagents were eliminated from the procedure.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2010.520183