The UN Security Council imposed three sets of sanctions on North Korea last year in response to the reclusive state's nuclear and missile tests, including restrictions on oil sales.
But the US has said companies with ties across Asia were violating those sanctions, including by transferring oil to North Korean vessels at sea to avoid detection.
The latest man to be questioned, identified only by his family name Chuang, owns a ship suspected of transferring oil products to North Korea in the East China Sea, the Kaohsiung district prosecutor's office in southern Taiwan said.
He also intentionally filled out the name of the ship's previous owner rather than his own in official documents, prosecutors added.
"Chuang is the owner of the ship and he was aware that the ship's destination was to the international waters to sell oil products," it said in a statement.
Prosecutors did not name Chuang's ship but local media identified it as the "Jin Hye" which is registered in Sierra Leone.
He was released on a bail after questioning and has not been formally charged.
Prosecutors were not immediately available for comment.
Last month Kaohsiung prosecutors questioned another businessman Chen Shih-hsien also for allegedly selling oil to North Korea and breaching UN sanctions against the nuclear- armed regime.
Chen is being probed over links to Hong Kong-registered the Lighthouse Winmore which was impounded by South Korea in November.
The US Treasury Department also released satellite photos of a separate transfer with a North Korean vessel the Rye Song Gang 1 in October, without naming the second ship.
Chen has not been charged yet but Taiwanese authorities have banned all financial dealings with him and have frozen his company bank accounts.
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