By JO BECKER and RON NIXON

The United States government has awarded more than $107 billion in contract payments, grants and other benefits over the past decade to foreign and multinational American companies while they were doing business in Iran, despite Washington’s efforts to discourage investment there, records show.

That includes nearly $15 billion paid to companies that defied American sanctions law by making large investments that helped Iran develop its vast oil and gas reserves.

For years, the United States has been pressing nations to join its efforts to squeeze the Iranian economy, in hopes of reining in Tehran’s nuclear ambitions. Now, with the nuclear standoff hardening and Iran rebuffing American diplomatic outreach, the Obama administration is trying to win a new round of United Nations sanctions.

But a New York Times analysis of federal records, company reports and other documents shows that both the Obama and Bush administrations have sent mixed messages to the corporate world when it comes to doing business in Iran, rewarding companies whose commercial interests conflict with American security goals.

Many of those companies are enmeshed in the most vital elements of Iran’s economy. More than twothirds of the government money went to companies doing business in Iran’s energy industry - a huge source of revenue for the Iranian government and a stronghold of the increasingly powerful Islamic Revolutionary Guards Corps, a focus of the Obama administration’s proposed sanctions because it oversees Iran’s nuclear and missile programs.

Other companies are involved in auto manufacturing and distribution . One supplied container ship motors to IRISL, a government-owned shipping line that was subsequently blacklisted by the United States for concealing military cargo.

Beyond $102 billion in United States government contract payments since 2000 - to do everything from building military housing to providing platinum to the United States Mint - the companies and their subsidiaries have reaped a variety of benefits. They include nearly $4.5 billion in loans and loan guarantees from the Export-Import Bank, a federal agency that underwrites the export of American goods and services, and more than $500 million in grants for work that includes cancer research and the turning of agricultural byproducts into fuel.

In addition, oil and gas companies that have done business in Iran have over the years won lucrative drilling leases for close to 5.6 million hectares of offshore and onshore federal land.

The government can, and does, bar American companies from most types of trade with Iran, under a broad embargo that has been in place since the 1990s. But as The Times’s analysis illustrates, multiple administrations have struggled to exert American authority over companies outside the embargo’s reach - foreign companies and the foreign subsidiaries of American ones.

Indeed, of the 74 companies The Times identified as doing business with both the United States government and Iran, 49 continue to do business there with no announced plans to leave.

One of the government’s most powerful tools to influence the behavior of companies beyond the jurisdiction of the embargo is the Iran Sanctions Act, devised to punish foreign companies that invest more than $20 million in a given year to develop Iran’s oil and gas fields. But in the 14 years since the law was passed, the government has never enforced it, in part for fear of angering America’s allies.

Among the companies is the Brazilian state-controlled energy conglomerate Petrobras, which last year received a $2 billion Export-Import Bank loan to develop an oil reserve off the coast of Rio de Janeiro.

Despite repeated American entreaties, Petrobras had previously invested $100 million to explore Iran’s offshore oil prospects in the Persian Gulf.

But the Export-Import Bank loan could help create American jobs, since Petrobras would use the money to buy goods and services from American companies. Perhaps more important, it could help develop a source of oil outside the Middle East.

After The Times inquired about the loan, officials of the bank said they asked for and received a letter of assurance from Petrobras that it had finished its work in Iran.

On November 23, Iran’s president, Mahmoud Ahmadinejad, visited Brazil, and the two countries agreed to share technical expertise on energy projects. Iranian officials said they might offer Petrobras additional incentives for further investment.

The visit infuriated American officials, who felt it undercut efforts to press Iran on its nuclear program while lending international legitimacy to the Iranian president.

In the meantime, Petrobras’s Tehran office remains open.

Representative Ron Klein, a Florida Democrat, wrote a contracting provision moving through Congress that would mandate that companies that invest in Iran’s energy industry be denied federal contracts.

“We need to send a strong message to corporations that we’re not going to continue to allow them to economically enable the Iranian government to continue to do what they have been doing,’’ Mr. Klein said.


President Mahmoud Ahmadinejad of Iran in Brazil, where Petrobras deals with the United States and Iran. / FERNANDO BIZERRA JR. /EUROPEAN PRESSPHOTO AGENCY

THE NEW YORK TIMES