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Bolted pipe flange connections with metallic flat gaskets or ring type joint (RTJ) gaskets are used under higher pressure and higher temperature. However, a sealing mechanism is not known and a design method is not established how to determine bolt preload for preventing leakage from the connection with metallic gaskets. In addition, the characteristics of the connection are not known when oval and octagonal gaskets are used. In previous paper, when the contact stress of metallic flat gasket reaches the stress at plastic deformation inflection point, the leak rate is decreased rapidly. However, the leak rate could be measured up to 1.0 × 10−5 Pa · m3/s level. The objectives of the paper are to measure the leak rate of the metallic flat gasket of which the contact stress is over the stress at plastic deformation inflection point, and to measure the leak rate of 1.0 × 10−9∼10 Pa · m3/s level in the flat metallic gasket in the platen tests and the connection with RTJ gaskets. In addition, the characteristics of the connection are examined when oval and octagonal gaskets are used. As a result, it is found that the leak rate for the metallic flat gasket can be measured around 1.0 × 10−9∼10 Pa · m3/s in the platen tests when the contact stress of aluminum gasket reaches the stress at plastic deformation inflection point and more while the leak rate of SUS 304 flat gasket is around 1.0 × 10−7∼8 Pa · m3/s even if the contact stress is over 1.3 times of the stress at plastic deformation inflection point. In addition, the sealing characteristics of the connection with oval gasket are shown to be better than that with octagonal gasket. From a laser microscope observation, it is found that the contact area of oval gasket in the connection is smaller than that of octagonal gasket in the connection.