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Check all connections for air leak including the water drain valve with soapy water. If no air leaking from connections, spray soapy water on head area where head attaches to the cylinder checking for gasket leaks. If no leaks are found, most likely problem is in the head /valves /internal gasket leak. If head gasket or valves are leaking, you will notice that air seems to blow out of the intake filter (normally there is good suction at the intake). Good luck
check air tank drain valve located on bottom of tank, if it is not leaking try adjusting air pres regulator (large black knob close to air hose connection.) the knob when turned in will increase the tank air pressure, if knob wont turn check that lock ring on bottom of knob to make sure it is disengaged. also check for air leaks in all lines and connections
The problem with compressors not building pressure is usually a bad pressure switch or bad regulator. Does the motor shut off at 20psi or does it continue running and not build pressure? If the motor continues to run with no increase in pressure, the you should go over the machine looking for air leaks from your regulator back all the way to the motor. Any air leak while the compressor is running can cause the pressure to "peak" way before the intended shutoff that it is regulated to.
It is possible the reeds in the intake are loose. This requires removing the top of the cylinder, not for amateurs as the bolts need proper torque and the crack easily. Also check the cold start valve, it is a small brass valve with a needle in the center it bleeds air for cold starts, should be on the tank if so equipped. Check the unloader too. Run the unit then shut off the motor at 20 lbs and listen for air leaking. Not hearing air leaking would indicate the first suggestion of reeds or if it is old, worn rings.
Oil free pumps do tend to blow the piston ring (not too expensive) available at searsparts.com. Remove covers to pump and manually turn crank until piston is at top and look at the condition of the cylinder neer top, If it looks scratched, order cylinder kit with piston ring. If it looks good and shiney, could be the valve plate in the head. There are reed valves that tend to break. Run pump however with covers removed and check with soapy water for air leaks and repair as needed (air leaks under the cover will prevent unit from filling). Good luck
The issue suggests that the head gasket is blown between the two cylinders or the reed valves are not seating or broken. The only other condition that would cause this is a leak. Here are a couple of simple tests. For leak spray soapy water on all connections and fittngs including the pressure regulator and the bottom of the pressure switch while unit is running. Repair as needed. If no leak is found, run compressor untill it reaches 60 or stops increasing and feel for suction at the air filter intake. The best way to check for suction is to remove the air filter and feel for suction at intake port-hole. The suction should be very strong. When valves are leaking it almost feels that the air is blowing out thru intake. If little or no suction, remove head and valveplate and replace parts as needed. Parts are available at www.chpower.com or www.toolpartsdirect.com. Good luck and post again if you have other question.
IS YOUR AIR FILTER CLOGGED. SOUNDS LIKE THE VALVES IN YOUR HEAD ARE NOT CLOSING ALL THE WAY. THEY ARE MOST LIKELY REED VALVES, THIN STRIPS OF METAL THAT OPEN AND CLOSE WHEN THE PISTON MOVES. MAKE SURE THEY ARE CLOSING ALL THE WAY (NOT CARBONED UP). DID YOU REMOVE THE HEAD AND DID YOU PUT BACK LIKE YOU FOUND IT - NOT TURNED OR FLIPPED OVER. SEE IF YOUR FINGER WILL GET SUCKED UP TO THE INTAKE HOLE.