A grind-strengthened strategy was developed for the solvent-free synthesis of sucrose fatty acid esters (SE). The effect of grinding time, emulsifier, reaction time, reaction pressure and catalyst dosage on yields and production distributions of SE were investigated by using sucrose and fatty acid methyl ester as reactants. The generated SE was purified by using water washing and alcohol extraction. And they were characterized by the analysis of Fourier Transform Infrared Spectroscopy (FTIR) and High Performance Liquid Chromatography-Evaporative Light Scattering Detector (HPLC-ELSD). The results showed that the grinding pretreatment could reduce the particle size of reaction dispersion (D50) to 5 μm and effectively enhanced the solvent-free transesterification reaction of sucrose esters. Under the optimized conditions a fatty acid methyl ester conversion of 91.2% and a SE yield of 61.6% were achieved, in which the grinding time was 60 min, the dosage of potassium stearate was 10%, the dosage of potassium carbonate was 2.0%, the reaction was conducted under the pressure of 0.5 kPa for 6 h. The amount of SE reached up to 81.9% in the purified product, and its free sugar was 0.6%, acid value was 3.0 mg KOH/g, water content was 0.2%, ash content was 0.5%, and all these indicators completely accorded with the Food and Agriculture Organization / World Health Organization (FAO/WHO) standard.