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Wax esters from fatty alcohols and uncommon fatty acids were synthesized in yields up to 90% when commercially available microbial lipases from Rhizomucor miehei (Lipozym ewM) and Candida antarctica (SP 435) were used with limited water content in nonpolar solvents under mild conditions. The corresponding fatty acids were prepared by chemical conversion of naturally occurring resources (agricultural surpluses). Also, when phenylboronic acid was added as solub'dizing agent in a nonpolar solvent, the direct enzymatic monoacylation of glycerol with uncommon fatty acids was successful. The measurement of n/A-isotherms by means of a Langmuir film balance indicated medium film pressures, medium or large molecular areas, and interesting phase behavior. The monolayer of a wax ester at the air/water interface could be directly visualized by Brewster angle microscopy.KEY WORDS: n/A-isotherms, Brewster angle microscopy, film pressure, glycerol, lipase, monoacylation, nonaqueous conditions, uncommon wax esters.

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The continuous production of aleuritic acid decyl ester has been investigated with LipozymeTM as biocatalyst in a fixed‐bed reactor. To avoid the limiting effects of mean substrate solubility, the direct synthesis without organic solvents was chosen, whereby a yield of 90% was obtained depending on the residence time. A comparison of different reaction paths to synthesize a centrally dihydroxylated decyl ester indicated a preference for transesterification of the methyl ester. Under external compression, the interfacial behavior of several enzymatically produced hydroxy wax esters was determined with a Langmuir film balance to find a structure/efficiency relationship. Brewster‐angle microscopy allowed direct visualization of a wax ester monolayer at the air/water interface.

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