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[Abstract Image] In this contribution, we present a process development for an easy, efficient, and sustainable synthesis of recently developed biobased and biodegradable high-performance lubricants utilizing lipase catalysis. The lubricants are produced starting from a regioisomeric mixture of methyl 9-/10-hydroxymethylstearate as an oleic acid-derived raw material by means of solvent-free esterification at low temperatures, making them highly attractive for industrial-scale applications. The process setup is semicontinuous and enables a simple and efficient catalyst recycling, which has been demonstrated over in total 21 reaction cycles. The immobilized lipase catalyst (Novozym 435) shows excellent long-term stability within the process with a very low loss of enzyme activity of only 0.25% per cycle, thus opening up the perspective for an economically feasible production on an industrial scale. Furthermore, an _E_ factor of