Abstract :
[en] New rhamnolipids were obtained via the development of a synthesis procedure consisting of two biocatalyzed
steps. In the first step, naringinase was used to introduce a primary alcohol function onto
rhamnose by glycosylation of 1,3-propanediol. In the second step, immobilized lipase B from Candida
antarctica catalyzed the esterification of the primary hydroxyl group with mono- and di-carboxylic fatty
acids of increasing chain length (from C8 to C14). For the monoic acids, the initial rate and 24 h yield
decreased with increasing chain length. For the dioic acid, the number of carbon atoms of the acid did not
influence these parameters. The new rhamnolipid obtained with tetradecanoic acid showed very good
surface properties. At pH 5, it had a very low critical aggregation concentration of 1.70 M and it diminished
water’s surface tension to 27.6 mN/m. It was also able to form stable insoluble monolayers. On
the other hand, the rhamnolipid formed with tetradecanedioic acid showed far less interesting surface
properties.
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