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One of the important environmental aspects of improving the efficiency of primary municipal solid waste (MSW) technology is reducing the permeability of the filtrate. The filtrate is a major contributor to the negative impact of landfill sites MSW on the environment due to the presence of toxic substances, heavy metals, organic, inorganic compounds, etc., which are included in the waste or are products of their decomposition. The main fraction of MSW is organic matter (biomass), which causes biological pollution. A literature analysis showed that reducing the size of MSW particles from 50 to 10 mm decreases their water permeability by almost 22 times during landfilling, which helps to reduce the intensity of soil and groundwater contamination by filtrate and improve environmental safety in general. The regression analysis method was used to detect the degree of influence of the sizes of MSW particles on their water permeability during disposal at the landfill. A pairwise regression analysis was performed by selecting the best kind of function from the 16 most common types by the criterion of the maximum correlation coefficient. The regression was performed on the basis of linearization transformations, which allow reducing a nonlinear dependence to a linear one. The regression equation coefficients were determined using the least-squares method using the developed “RegAnaliz” software, which is protected by a copyright registration certificate for the work. The regression dependence of the water permeability of the filtrate on the particle size of the crushed MSW was revealed. The obtained regression dependence can be used to create a methodology for engineering calculations of the parameters of the equipment for grinding MSW as one of the methods of their initial processing. This dependency can also be taken into account when developing a MSW management strategy aimed at minimizing their negative impact on the environment and enhancing the environmental safety in general.