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Biorefineries provide an important alternative for petroleum-based refineries to reduce CO2 emissions and increase the share of renewable feedstocks for the production of chemicals and fuels. Vegetable oils and animal fats are used as renewable raw materials for the production of oleochemicals. Never before in the history of the oleochemical industry have the changes been more dramatic than in the last decades. The rapid growth of palm oil, the rise of oleochemicals production in Southeast Asian Nations and an increased competition with the biofuel industry for feedstocks form a challenge for the traditional oleochemical players in Europe and North America. This increased competition forces European oleochemical companies such as Oleon NV to diversify the feedstocks they process, ranging from low quality animal fat to higher quality vegetable oils. Operating a continuous installation with a variable feed composition poses significant challenges for process operation and control to ensure resource efficiency, high product yields and excellent product quality. Petroleum refineries regularly use mechanistic and statistical modelling to tackle this challenge of feedstock diversity and adapt process conditions for compositional variability of the incoming crude oil. Applying these techniques to biorefineries, such as for the production of oleochemicals, could aid in utilizing variable bio-based feedstock streams more efficiently, enable the use of lower quality-grade feedstocks and improve adaptability toward future changes in demand and supply.

In this PhD thesis isotope-labelled AHLs were synthesized which can be used as a tool to study the metabolization of AHLs. Secondly, the possible rearrangement of N-(3-hydroxyacyl)- L-homoserine lactones was investigated and proven to be very unlikely. This investigation resulted in the successful development of a synthetic entry toward 1,4-oxazepane-2,5-diones, which are extremely difficult to synthesize due to the presence of a lactam with a preference for the trans-conformation and a labile lactone moiety in one ring structure. By applying the disclosed methodology on the synthesis of the natural product serratin, the incorrect structural assignment of this compound was identified. Thirdly, the profound effect of a QS signal molecule, HO8, on the swarming behavior of Pseudomonas species CMR12a, was demonstrated. This influence goes presumably via an elegant fine-tuning of the ratio of the two produced CLPs, orfamide and sessilin via the control of orfamide production.