Mining magnate Nathan Tinkler's business empire is under renewed pressure after a court ordered his Mulsanne Resources be liquidated over a failed $28.4 million debt to Blackwood Corporation.
It is understood that if the money cannot be recovered from Mulsanne then the directors, which includes Mr Tinkler, could be liable for trading while insolvent.
The liquidators could also seek to recover the $28.4 million from the directors.
But a spokesman for Tinkler Group said the court's ruling would not affect its stable of other companies, which include Hunter Ports, International Ports and Logistics, Hunter Sports Group and Patinack Farm.
"The liquidation of Mulsanne Resources does not affect any other part of the Tinkler Group," he said.
Coal explorer Blackwood sued shelf company Mulsanne Resources after it agreed to buy a 33.85 per cent stake in it for $28.4 million, but then failed to follow through with the deal.
NSW Supreme Court senior deputy registrar Nicholas Flaskas on Tuesday ordered that Mulsanne Resources be wound up and Ferrier Hodgson's Robyn Duggan and John Melluish be appointed as liquidators to recover the debt.
The order came after two months of court hearings in which the case was repeatedly adjourned for settlement negotiations.
It is the first time Mr Tinkler has failed to settle a legal threat to wind up one of his companies.
In the past two months, he has settled a dispute with Mirvac over his failure to meet a deadline on a $17 million payment, and a separate dispute with mining services company Sedgman.
Mr Tinkler's Patinack Farm also recently held a reduction sale of more than 200 of its horses.
He also recently lead a coup against the board of mining company Whitehaven Coal, in which he is majority shareholder.
But the move ended up narrowly failing to deliver the company a "first strike" at its annual general meeting.
Blackwood has previously said it was waiting for the money to fund drilling of its coal tenements in Queensland.
Shareholders in the coal explorer approved the share placement on July 12 and the payment was originally expected within a week.
Blackwood shares plummeted 25 per cent after the court decision before closing 22.2 per cent, or four cents, lower at 14 cents.
Mulsanne was also ordered to pay Blackwood's court costs.