In order to provide a new way for waste cooking oil(WCO) resource utilization, several diester derivatives were obtained from WCO through a three-step chemical modifications, viz.: transesterification, epoxidation and oxirane ring opening with carboxylic acids. The effects of the chain length of side chain groups on the viscosity, acid value, low temperature fluidity, thermo-oxidative stability, tribological properties and surface tension of diester derivatives were investigated. The results showed that increasing the chain length of side chain groups had a positive influence on the viscosity, viscosity index, acid value, pour point, friction coefficient and wear scar diameter along with a negative influence on the oxidation onset temperature, volatile loss, insoluble deposit, maximum non-seizure load and surface tension. These diester derivatives exhibited improved physicochemical and tribological properties that make themselves promising environmentally friendly biolubricant basestocks. In order to provide a new way for waste cooking oil (WCO) resource utilization, several diester derivatives were obtained from WCO through a three-step chemical modifications, viz .: transesterification, epoxidation and oxirane ring opening with carboxylic acids. The effects of the chain length of side chain groups on the viscosity, acid value, low temperature fluidity, thermo-oxidative stability, tribological properties and surface tension of diester derivatives were investigated. The results showed that increasing the chain length of side chain groups had a positive influence on the viscosity, viscosity index, acid value, pour point, friction coefficient and wear scar diameter along with a negative influence on the oxidation onset temperature, volatile loss, insoluble deposit, maximum non-seizure load and surface tension. and tribological properties that make in pre-employment environmentally friendly biolubricant basestoc ks.