SAO PAULO — SAO PAULO (AP) — Brazil on Thursday said it seized 1.2 billion reais (about $220 million) in assets linked to a sprawling criminal network as part of a nationwide investigation into a money laundering scheme involving investment funds and the fuel sector.

Officials executed 14 search and seizure warrants and 14 preventive arrest warrants, resulting in five arrests, in what Justice Minister Ricardo Lewandowski said was one of the largest operations against organized crime in the country’s history.

Federal authorities did not name any specific individuals or companies targeted, citing sealed and ongoing investigations. However, state prosecutors in Sao Paulo, who contributed to the operation, said the scheme involved members of the First Capital Command crime syndicate, or PCC.

Lewandowski said: “This operation addresses how criminal organizations have infiltrated and appropriated parts of the fuel industry, and how this connects to the financial sector through money laundering schemes.”

Authorities identified 40 investment funds with a combined asset value of 30 billion reais (about $5.5 billion). These funds were allegedly used to shield assets for criminal organizations, holding properties such as a port terminal, four ethanol plants and about 1,000 gas stations across 10 Brazilian states. The fuel sector was chosen as a starting point by investigators into the criminal networks because it was the most visible one, they said.

“People know how it has worked, but it took a national effort to reach the heart of the problem and be able to confront it,” Finance Minister Fernando Haddad told journalists.

Andrea Chaves, deputy secretary for tax enforcement at the Brazilian Federal Revenue Service, said the investigation highlighted the “extremely serious” infiltration of organized crime into the real economy and financial markets.

“This affects the entire supply chain — from fuel importation, production, distribution and commercialization,” Chaves said. “In the financial sector, it involves asset concealment and shielding, in schemes similar to the hiding of shareholders in offshore tax havens. The Brazilian state cannot allow this to happen.”

Sao Paulo’s State Public Prosecutor’s Office said its investigation found that criminal organizations used adulterated fuel at more than 300 gas stations to launder illegal money through a complex network of intermediaries, including shell companies, investment funds and payment institutions.

“A significant portion of the unbacked funds was used to acquire ethanol plants and expand the group’s criminal operations, which now include fuel distributors, transport companies and gas stations,” prosecutors said.

The fraud also involved irregular imports of methanol through the Port of Paranagua, in Parana state. The methanol was not delivered to the recipients listed on invoices but instead sent to gas stations and distributors, where it was used to adulterate fuel.

“Consumers were allegedly charged for less fuel than indicated by the pumps or received fuel that was chemically altered and failed to meet technical standards set by Brazil’s National Petroleum Agency,” prosecutors said.

Nívio Nascimento, a foreign relations advisor at the Brazilian Forum on Public Safety — an independent group that tracks crime — said the operation marked a milestone in combating the infiltration of criminal organizations into strategic sectors of Brazil’s economy.

“Enforcement still needs to be expanded, considering the centrality of these economic sectors — fuel, beverages, cigarettes and several other items — that have been appropriated by criminal organizations,” Nascimento told The Associated Press.

PCC is Brazil’s biggest and most powerful organized crime group. It was founded in 1993 by hardened criminals inside Sao Paulo’s Taubate Penitentiary to pressure authorities to improve prison conditions. It quickly started using its power to direct drug dealing and extortion operations on the outside. Over the past few years, the gang has diversified their investment portfolios into various illicit markets.

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