op0c00131_si_001.pdf (13.86 MB)
Process Intensification for Obtaining a Cannabidiol Intermediate by Photo-oxygenation of Limonene under Continuous-Flow Conditions
journal contribution
posted on 2020-05-22, 22:13 authored by Anderson
R. Aguillón, Raquel A. C. Leão, Kleber Thiago de Oliveira, Timothy John Brocksom, Leandro S. M. Miranda, Rodrigo O. M. A. de SouzaWe have investigated
the synthesis of p-mentha-2,8-dien-1-ol
(1) as a cannabidiol precursor by photochemical oxidation
of (R)-limonene (2) with singlet oxygen
(1O2) using meso-tetraphenylporphyrin
(TPP) as a photosensitizer. Different home-made engineered set-ups
were used for reaction intensification. Under optimized conditions,
the target compound was obtained at up to 580.8 μmol·min–1 (66.7 g·day–1) using a low
concentration of TPP (0.1 mM) and requiring 20 min for total conversion.
Low-temperature photoreactor approaches made it possible to raise
the level of selectivity of the desired limonene derivative up to
66%, with 55% conversion.
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mM20 mincannabidiol precursorphotosensitizerselectivityconcentrationContinuous-Flow Conditionstetraphenyltarget compoundconversionmenthaLimonenePhoto-oxygenationmolprocess IntensificationLow-temperature photoreactor approachessynthesislimoneneoxidationCannabidiol Intermediate1 O 2TPPset-upreaction intensificationObtainingDifferent home-made580.8singlet oxygenoptimized conditionsmeso
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