Increasing the reliability of combustion engines while further reducing emissions and life cycle costs are the main drivers for optimizing lubricating oil consumption (LOC). However, in order to reduce the lube oil consumption of an engine, it is crucial to measure it accurately. Therefore, a LOC measurement device based on the use of the stable isotope deuterium has been developed. Previous publications have focused on the use of passenger car engines. This publication describes the first application of this newly developed method on a large gas engine. This is of particular interest as large-bore engines might show different oil consumption behavior, much higher LOC in gram per hour and the bigger oil reservoir need larger amounts of tracer. Additionally, a different type of fuel has an effect on oil consumption measurement as well, as presented in this paper. The results showed this method can be applied to large gas engines as well after conducting minor changes to the measurement setup. However, other than liquid fuels, the origin and isotopic composition of the natural gas has to be monitored. Ideally, gas from large storage is used for carrying out these measurements.

Teraryl-based alpha-helix mimetics have resulted in efficient inhibitors of protein-protein interactions (PPIs). Extending the concept to even longer oligoarene systems would allow for the mimicking of even larger interaction sites. We present a highly efficient synthetic modular access to quateraryl alpha-helix mimetics, in which, at first, two phenols undergo electrooxidative dehydrogenative cross-coupling. The resulting 4,4′-biphenol is then activated by conversion to nonaflates, which serve as leaving groups for iterative Pd-catalyzed Suzuki-cross-coupling reactions with suitably substituted pyridine boronic acids. This work, for the first time, demonstrates the synthetic efficiency of using both electroorganic as well as transition-metal catalyzed cross-coupling in the assembly of oligoarene structures.

Teraryl‐based α‐helix mimetics have proven to be useful compounds for the inhibition of protein‐protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl‐based α‐helix mimetics using a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd‐catalyzed cross‐coupling used for teraryl assembly. In previous publications we have introduced the methodology of 4‐iodophenyltriflates decorated with the side chains of some of the proteinogenic amino acids. We herein report the core fragments corresponding to the previously missing amino acids Arg, Asn, Asp, Met, Trp and Tyr. Therefore, our set now encompasses all relevant amino acid analogues with the exception of His. In order to be compatible with the triflate moiety, some of the nucleophilic side chains had to be provided in a protected form to serve as stable building blocks. Additionally, cross‐coupling procedures for the assembly of teraryls were investigated.

Teraryl‐based α‐helix mimetics have proven to be useful compounds for the inhibition of protein‐protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl‐based α‐helix mimetics using a benzene core unit featuring two halide leaving groups of differentiated reactivity in the Pd‐catalyzed cross‐coupling used for teraryl assembly. The use of para‐bromo iodoarene core fragments resolved the issue of hydrolysis during cross‐coupling that was observed when using triflate as a leaving group. We report a complete set of para‐bromoiodoarene core fragments decorated with side chains of all proteinogenic amino acids relevant for PPI (Ala, Arg, Asn, Asp, Cys, Gln, Glu, His, Ile, Leu, Lys, Met, Phe, Ser, Thr, Trp, Tyr and Val). In order to be compatible with general cross‐coupling conditions, some of the nucleophilic side chains had to be provided in a protected form to serve as stable building blocks.

Because of the impact of lubrication on the efficiency and the lifecycle cost and emissions, the lubricating-oil consumption (LOC) is one of the key indicators in the research and development of internal combustion engines. State-of-the-art methods for LOC measurement are based on the use of a certain tracer to track the oil consumption. However, all of the currently available tracers have their downsides (e.g., the use of a radioactive tracer, corrosive emissions, etc.). Therefore, in the course of this research project, a new tracer substance that is based on a stable nonradioactive isotope of hydrogen—deuterium—was developed and tested thoroughly. The LOC is monitored by a hydrogen/deuterium isotopic ration in the exhaust gas by using an isotopic water analyzer. Tribologically important properties, such as the viscosity, stability, and compatibility of the tracer were investigated by laboratory experiments by using several tools, such as infrared spectroscopy, gas chromatography, thermogravimetry, etc. The properties relevant to the applicability of the method, such as the accuracy and the reproducibility, were investigated by engine test-bench experiments. Finally, long-term stability tests of the tracer were conducted with a field test.

The accurate and precise measurement of lubricating oil consumption is critical for developing environmentally friendly internal combustion engines, particularly hydrogen-fueled internal combustion engines. The deuterium tracer method is based on the addition of poly-deuterated base oil tracers to fully formulated oils for precise, accurate, and fast lubricating oil consumption measurements. Previously performed measurements have shown that the use of poly-deuterated poly-alpha olefins has minimal impact on lubricating oil properties, except for a slight drop in oil viscosity. To further reduce the impact on lubricating oil characteristics, a new base oil for the synthesis of a poly-deuterated tracer is introduced, and its influence on the lubricating oil’s chemical, tribological, and rheological properties is analyzed. Furthermore, the influence of the tracer addition on the preignition tendencies of the fully formulated oil is also examined. Based on the analyses, no relevant changes in the lubricating oil properties, such as viscosity, density, and thermal degradation behavior, can be observed. Additionally, the deuterium tracer does not negatively influence combustion anomalies, thus reducing preignition tendencies. These results establish the method’s compatibility with new-generation engines, especially hydrogen-fueled internal combustion engines.