This is my first post, I'm hoping the chemistry experts here can give me some guidance.
I observed an unexpected color change dissolving a quaternary ammonium iodide in alcohol.
I dissolved 1.5 grams of tetrabutylammonium iodide powder in about 8 mL of water-white 2-ethylhexanol (2EH) at room temperature. TBA iodide is a white powder, which forms a clear colorless solution in water and methanol. Immediately upon adding the 2EH, the solution began to turn yellow-brown. Within a minute of swirling, the TBA iodide appeared to fully dissolve or react to form a dark brown solution free from residual solids or haze.
The reagents are somewhat old. The TBA-I is about 2 years old, the 2EH is about 6 years old. However the degree of opacity is so significant I find it hard to believe that impurities alone are to blame. My instinct is that molecular iodine is somehow forming, but I am having difficulty identifying a mechanism that occurs so rapidly.
I do not have newer reagents to determine if it is a purity issue. Any help would be appreciated.