Synthetic oil was an essential industry for the war economies of Japan and Germany. When a project of developing a synthetic oil industry was launched in Japan in 1937 under the Seven Year Plan for Promoting the Synthetic Oil Industry, the German synthetic oil industry had already been established, securing a stable domestic market under the Four Year Plan of 1936. Toward the summer of 1939 Krupp started to take orders for its high pressure vessels and other machines from the Japanese Navy, Army and private synthetic oil industries. Krupp, however, failed to obtain to obtain export permissions from German authorities. The conclusion of the Tripartite Pact in September 1940 raised Japanese expectation for increasing economic and technological cooperation between Japan and Germany. Among the most essential areas for cooperation was the transfer of German synthetic-oil technology and related machines to Japan. At the beginning of 1941 in Berlin, Yoshikiyo OSHIMA, a director of Teikoku Nenryo(imperial Fuel), a half state-owned company, made every effort to import high pressure vessels and other machines in cooperation with some affiliates of Japanese trading companies such as Mitsubishi, Mitsui and Okura. Krupp was most eager to make export contracts. The chemical concern I. G. Farben also became interested in exporting German machines, for which I. G. might thereby obtain licence fees. However, Krupp and I. G. failed to cooperate each other. More decisively, the German authorities, especially the Agency for the Four Year Plan, remained opposed to the transaction. They attached more importance to the fulfillment of the Four Year Plan than to the cooperarion with Japan under the Pact. In this way, the expected economic and technological cooperation with Germany bore no fruit in the development of synthetic oil industry in Japan. The Tripartite Pact was an 'ineffective alliance' in economic, technological as well as political sense.