There are approximately 4 cups per pound of 10x sugar. I'm sticking with 3 3/4 unless I sift it a few times. In most cases it doesn't affect the texture of the finished product and with that much being used, it definitely doesn't affect the taste!
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It really depends on what kind of sugar that you're measuring sugar, brown, packed is 8oz in a cup sugar granulated 71/2 ozs. in a cup sugar powdered is 43/4 oz in a cup. these measurements are weight measurements. brown is 20 cups, granulated is 93/4 cups powdered 5.93/4 cups in ten pounds of sugar.
Cups are a liquid measurement. Liquid measurements measure volume, and you cannot transfer that into weight unless you know the density of the substance you're measuring.
A good estimate would be about 20 but that is not exact. Cups is a measure of volume. Pounds is a measure of weight and mass. You can not directly convert the two.