Singularities of the area preserving curve shortening flow with a Neumann free boundary condition

We consider the area preserving curve shortening flow with Neumann free boundary conditions outside of a convex domain or at a straight line. We give a criterion on initial curves that guarantees the appearance of a singularity in finite time. We prove that the singularity is of type II. Furthermore, if these initial curves are convex, then an appropriate rescaling at the finite maximal time of existence yields a grim reaper or half a grim reaper as limit flow. We construct examples of initial curves satisfying the mentioned criterion.