A method for peroxidase-catalyzed oxidation of aromatic hydrocarbons and derivatives thereof
A peroxidase and reaction technology, applied in the field of biocatalysis, can solve the problems of harsh production oxidation process, strict environmental protection requirements, dependence on imports, etc.
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Embodiment 1
[0046] Embodiment 1: the preparation of the compound 4-chlorobenzyl alcohol of following formula
[0047]
[0048] In a 2 mL reaction bottle, add 890 microliters of phosphate buffer solution (pH=7, 50 mmol / L), add 100 microliters of methanol solution of 4-chlorotoluene (50 mmol / L), and add 10 microliters of peroxidase UPO Enzyme (500 nmol / L), use an infusion pump to pass H at a rate of 5mM / h 2 o 2 .
[0049] The above reaction system was stirred and reacted with a constant temperature mixer at 30°C for 15 hours, and then the reaction was terminated. Take 100 microliters of the reaction solution, add 200 microliters of ethyl acetate, extract, dry over anhydrous sodium sulfate, and detect and analyze by gas chromatography. The yield is 85 %.
Embodiment 2
[0050] Embodiment 2: the preparation of compound 4-chlorobenzyl alcohol or 4-chlorobenzaldehyde of following formula
[0051]
[0052] In a 1L reaction flask, add 890 ml of phosphate buffer solution (pH=7, 50 mmol / L), add 50 ml of methanol solution of 4-chlorotoluene (50 mmol / L), add 5 ml of peroxidase UPO enzyme ( 500 nmol / L). Inject H at a rate of 5 mmol / h using an infusion pump 2 o 2 .
[0053] The above reaction system was stirred and reacted with a constant temperature oscillator at 30° C. for 5 hours, and then the reaction was terminated. The reaction solution was extracted twice with 500 ml of ethyl acetate, the extracts were combined, and the organic phase was dried with anhydrous sodium sulfate, and the ethyl acetate was removed by rotary evaporation. After purification on a silica column, the overall yield was 71% (19% for 4-chlorobenzyl alcohol and 52% for 4-chlorobenzaldehyde.
[0054] figure 1 This is the gas chromatogram of 4-chlorobenzyl alcohol and 4-...
Embodiment 3
[0055] Embodiment 3: the preparation of compound 3-chlorobenzyl alcohol or 3-chlorobenzaldehyde of the following formula:
[0056]
[0057] In a 2 mL reaction bottle, add 890 microliters of phosphate buffer solution (pH=7, 50 mmol / L), add 100 microliters of 3-chlorotoluene in methanol solution (50 mmol / L), and add 10 microliters of peroxidase UPO enzyme (500 nmol / L). Inject H at a rate of 5 mmol / h using an infusion pump 2 o 2 .
[0058] The above reaction system was stirred and reacted with a constant temperature mixer at 30°C for 4 hours, and the reaction was terminated. Take 100 microliters of the reaction solution, add 200 microliters of ethyl acetate, extract, dry over anhydrous sodium sulfate, and detect and analyze by gas chromatography. The yield is 81 % (i.e. the yield of 3-chlorobenzaldehyde). figure 2 Gas chromatogram of 3-chlorobenzaldehyde for 4 hours under the reaction conditions.
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