Objectives: This study examined how ethanolamines (EAs) with the same functional alcohol group ($HOCH_2CH_2$), such as mono-EA (MEA), di-EA (DEA), and tri-EA (TEA), in water-based metalworking fluids (wbMWFs) are vaporized, condensed, and transformed by heat generated during metalworking. Methods: Two types of experimental apparatus were manufactured to achieve these objectives. Results: Vaporization tests using a water bath showed that the vaporization rate increased markedly from $0.19;mg/m^2{cdot}min$ at $23.5^{circ}C$ to $8.04;mg/m^2{cdot}min$ at $60^{circ}C$. Chamber tests with a heat bulb revealed that "spiked" MEA was fully recovered, while only 13.32% of DEA and no TEA were recovered. Interestingly, non-spiked types of EAs were detected, indicating that heat could convert EAs with more alcohol groups (TEA or DEA) into other EAs with fewer group(s) (DEA or MEA). The EA composition in fresh fluid was 4% DEA, 66% TEA, and 30% MEA, and in used fluids (n = 5) was 12.4% DEA, 68% TEA, and 23% MEA. Conversion from TEA into DEA may therefore contribute to the DEA increment. Airborne TEA was not detected in 13 samples taken from the central coolant system and near a conveyor belt where no machining work was performed. The DEA concentration was $0.45;mg/m^3$ in the only two samples from those locations. In contrast, airborne MEA was found in all samples (n = 53) regardless of the operation type. Conclusion: MEAs easily evaporated even when MWFs were applied, cleaned, refilled, and when they were in fluid storage tanks without any metalworking being performed. The conversion of TEA to DEA and MEA was found in the machining operations.