High temperature heat pumps (HTHPs) with heat sink temperatures in the range of 100 to 160°C are expected to become increasingly commercialized in the coming years. Major applications have been identified, particularly in the food, paper, metal and chemical industries, especially in drying, sterilization, evaporation, and steam generation processes. With the intensification of the F-gas regulations, only refrigerants with low GWP may be used in the near future. Replacement fluids for the currently applied hydrofluorocarbons (HFCs) R245fa and R365mfc are required. The actual research gap in the field of HTHPs is toextend the limits of efficiency and heat sink temperature to higher values, while using environmentally friendly refrigerants. Natural refrigerants such as water (R718) or hydrocarbons (e.g. R601 or R600) are promising candidates. However, special heat pump cycle designs with multi-stage recompression or sophisticated safety measures against flammability are needed, which can increase system costs. Various hydrofluoroolefins (HFOs) and hydrochlorofluoroolefins (HCFOs) have recently been developed, which exhibit very low GWPs, are non-flammable and show potential for use at high temperatures (i.e. their critical temperatures are above 150°C). The thermodynamic properties of these fluids allow subcritical heat pump operation at condensation temperatures in the range of about 100 to 160°C. This paper investigates the environmentally friendly HFOs R1336mzz(Z) and R1234ze(Z) and the HCFOs R1233zd(E) and R1224yd(Z) and compares the coefficient of performance (COP) and the volumetric heatingcapacity (VHC) with the HFC refrigerants R365mfc and R245fa at different condensation temperatures and temperature lifts. Based on simulations and literature findings, a single-stage HTHP with internal heat exchanger (IHX) has been designed and built to test the performance of various refrigerants and high-viscosity oils. The established laboratory scale HTHP provides 10 kW heating capacity and heatsink temperatures of 80 to 150°C. The system operates with a variable-speed reciprocating compressor and has an oil separator installed on the discharge side of the compressor. An IHX is used to ensure adequate superheating control. The system design, theoretical simulations and first experimental test results with R1233zd(E) are presented.