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A whole cell biocatalytic process was developed to enable the efficient oxidation of styrene to chiral (S)‐styrene oxide with an enantiomeric excess better than 99%. Recombinant Escherichia coli cells were employed to express the genes styAB encoding the styrene monooxygenase of Pseudomonas sp. strain VLB120 from an expression plasmid utilizing the alk regulatory system of P. oleovorans GPo1. The strains reached specific activities of up to 70 U* (g cell dry weight)⁻¹ in shake‐flask experiments with glucose as the carbon source. An efficient two‐liquid phase fed‐batch process was established for the production of (S)‐styrene oxide with hexadecane as an apolar carrier solvent and a nutrient feed consisting of glucose, magnesium sulfate, and yeast extract. Engineering of the phase fraction and the composition of organic phase and feed led to a 2‐L scale process with maximal volumetric productivities of 2 …