A federal judge in New York has issued a restraining order temporarily blocking Aegean Marine Petroleum Network’s $367m purchase of HEC Europe from the bunkering giant’s founder and former largest shareholder.

In a sharply worded rebuke of the proposed deal, US District Judge Loretta Preska said that the transaction with oil tycoon and shipowner Dimitris Melissanidis is not fair because there was no attempt to seek a shareholder vote and was timed before the company’s annual meeting.