Saying "Adiabatic" is very missleading. Adiabatic only indicates an absence of heat transfer.
Adiabatic expansion through a flow restriction is very different from adiabatic expansion of a gas through an expansion engine. In the first case, the gas that is expanding does no work. In the case of the gas expanding in the cylinder work is performed by the gas.
Using the first law of thermodynamics is the proper way to solve either of these problems. In the case of a gas being released from the bottle, the change in internal energy of the gas inside the bottle is equal to the enthalpy of the gas exiting the bottle.
In this case, you must perform the analysis iteratively since as the pressure decays, the gas gets colder, and the enthalpy of the gas venting from the bottle drops.
If done iteratively, you will eventually get the correct answer.
Alternatively, you can draw a control volume around the gas that never leaves the bottle. At first, it occupies a very small amount of room at the bottom of the bottle, and as it expands, it eventually displaces all the other gas and fills the bottle.
In this case, one can immediately conclude the gas that has expanded has undergone an isentropic expansion, just like the piston in a cylinder.
Note that I've done this analysis both ways and both methods give identical answers.
The result is about -190 F. I doubt it actually gets that cold though, since the process is not adiabatic. Heat transfer from the thermal mass of the bottle is still very significant. I've had to do numerous problems similar to this one at cryogenic temperatures, and I've always found that the heat transfer from the vessel is a very significant factor, so "adiabatic" it is not.