My guess is that the upper button won't work because you're trying to move the oil canister in a direction that it can't be moved.
Looking at the screenshot below...
Although there are twelve different positions for the green arrow to be facing (kind of like the hour hand of a clock), the upper button will only work here if the green arrow is pointing to seven o'clock because that would be the only way to get the oil can back to the center. (And perhaps it's not obvious, but the lights correspond to the location of your oil canister.)
