Some extra background...2 years ago, the AC stopped working and the compressor wouldn't spin. I diagnosed it to a failed clutch coil relay. Replaced the relay and it worked fine until the next year. When the AC stopped working again and the relay wasn't the problem I started looking around online. I found several posts talking about failed clutch coils and then found that the part was given an extended warranty from Acura but that ran out a couple years ago. I bought a new coil and installed it, but that didn't fix the problem. My fault for throwing parts at a problem instead of diagnosing them first. I gave up and took the car to a local mechanic...they evacuated the system and told me it was about 1lb low and refilled it to what they said was the correct volume...though when I asked the guy what it was filled to, his answer was vague so I don't know how much he actually put in. Obviously this didn't fix the problem or I wouldn't be creating a new post.
So, here's where the car sits today. If it is cool outside in the morning, the AC works and these are the pressures I am reading:
Low Side: 44psi
High Side: 110psi

After the system warms up:
Low Side: 32psi
High Side: 123psi

After everything gets too hot and the compressor stops:
High and Low Side: 140psi

The only thing I can think of is that it doesn't have enough refrigerant which allows the system to overheat too quickly/easily. Any ideas?