Conversion
of furfuryl alcohol to 4-hydroxy-2-cyclopentenone
was studied in a microreactor channel of 0.5 mm diameter and 1.5 m
length. Addition of 1 M N-methylpyrrolidinone as
a cosolvent significantly reduces the polymeric material normally
formed during the reaction in purely aqueous solution. The reaction
follows pseudo-first-order kinetics at constant pressure (200 bar)
with the values of ΔH
⧧ =
18 ± 2 kcal/mol and ΔS
⧧ = −38 ± 3 cal/mol/K. At 240 °C, 200 bar pressure,
and residence time of 1.5 min, the product is obtained with 98% conversion
and is isolated as a stable O-phenylacetyl derivative
in 80% yield. This racemic mixture was resolved into enantiomerically
pure forms by kinetic resolution with penicillin G acylase (E.C.3.5.1.11)
immobilized on epoxy-activated polymer in 90–92% theoretical
yield and >99% ee.
Allyl glycidyl ether-ethylene glycol dimethacrylate copolymer with 25 % crosslink density has been functionalized with various amines. The polymer bearing a dibenzyl amino function efficiently removed the soybean trypsin inhibitor (SBTI) and lipoxygenase (LOX) from soymilk. The polymer binds SBTI and LOX efficiently (25-30 mg/g) through a combination of hydrophobic and ionic interactions and denatures them at room temperature by simple contact for 1 h. The bound proteins can be easily recovered almost quantitatively by elution with 1 % (v/v) acetic acid, and the polymer can be recycled at least 10 times without significant changes in binding capacity.
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