Events in the Libya and elsewhere are casting a new light on Prince Andrew's business links

As turmoil rages in the Middle East, the Duke of York's business connections are beginning to unravel.

When the Duke of York began to come under fire over the contacts he had cultivated in his role as UK Special Representative for International Trade and Investment, UKTI (UK Trade and Investment) put out a list of testimonials from some of the UK companies he has helped to promote. Unfortunately, it transpired that the quotes were up to four years old. What is more, some of the listed companies declined to issue any fresh support.

At the very least, the story illustrates how recent events in the Middle East are training a spotlight on how nations like the UK do business in the region. And a glance at the Duke of York's engagements over the past 10 years, as revealed in the Court Circular, shows that he has been a regular visitor to the countries currently reeling from domestic unrest in the Middle East.

In the process, inevitably, he has had to rub shoulders with rulers, and the relatives and friends of rulers, whose regimes score low on most measures of democracy and human rights.

'Demanding, vain and difficult'
Take Tunisia. On 2 October 2010 the Duke of York gave a lunch at Buckingham Palace for Sakhar el-Materi, the son-in-law of President Zine el-Abidine Ben Ali (the president fled Tunisia just over three months later, on 14 January). When questioned about the engagement, a spokesman for Prince Andrew said: "Whatever has happened since, at the time it was a legitimate public engagement".

Critics might view this as disingenuous, particularly in the light of remarks by Stephen Day, UK ambassador to Tunis between 1987 and 1992. He told the BBC al-Materi was a "crook" and suggested that the embassy in Tunis would have been "very clear that this was a man who carried an awful lot of baggage".

It is a view that clearly held currency in wider diplomatic circles. A WikiLeaks cable, dated 28 February 2007, from Robert Godec, US ambassador to Tunisia, describes al-Materi as "demanding, vain and difficult". It evokes his decadent lifestyle – he keeps a tiger on his compound at Hammamet – and concludes that he and the Ben Ali family "are disliked and even hated by some Tunisians".

The same cable, incidentally, recounts el-Materi's claim that he had helped to secure several appointments for Prince Andrew during a recent visit to Tunisia, noting: "Before his intervention, El Materi said, the Prince had only one appointment with a single Minister."

Key defence market
Or take Libya. The connections between the UK and Saif al-Islam Gaddafi, one of Colonel Gaddafi's sons, have been well documented since the middle of February. The UK has not been a major trading partner with Libya in recent years, yet the Duke of York has been assiduous in courting the country.

We know that he travelled to Tripoli to meet the colonel in November 2008 in his capacity as Britain's trade envoy. Buckingham Palace has confirmed to Channel 4 News that they have met "privately" on two other occasions.

The duke also met Saif al-Islam Gaddafi twice in Libya in an official capacity in October and November 2007, months after BP announced it had struck a £450m deal with the Libya Investment Corporation (Saif presumably took time out from his academic schedule at the LSE to meet the prince – he was awarded his PhD in 2008).

Former Foreign Office minister Chris Bryant alleged recently that Prince Andrew was "a very close friend of Saif Gaddafi" (a claim not supported by evidence in the public domain) as well as being "a close friend of the convicted Libyan gun smuggler Taken Kaituni".

In July 2009 the Duke of York gave a seminar for the Libya Africa Investment Portfolio and attended a lunch in London given by Bashir Saleh Bashir, one of President Gaddafi's closest advisers.

The fact is that UKTI has designated Libya as a priority market country. And in a Freedom of Information document obtained by Campaign Against the Arms Trade, UKTI also lists Libya as a "key" defence and security market in 2010 and 2011.

However, the Libyan uprising, and the means used by Colonel Gaddafi to attempt to crush it in its early stages, focused attention on UK arms sales to the country. Who Knows Who has reported how crowd control vehicles manufactured by UK firm NMS International had apparently been used to attack anti-government protesters.

'Railing at anti-corruption investigators'
The UK is a major weapons producer, so it is not surprising that the Duke of York's responsibilities have seen him endorsing this country's arms manufacturers. On 20 July 2010, for example, he attended the Farnborough Air Show, the largest UK arms fair last year, where he met, among others, Prince Faisal of Jordan (son of the late King Hussein) and defence ministers from Malaysia and India.

The prince also gave a reception for the air show at St James's Palace and attended a dinner given by Rolls-Royce. It is not known who else attended the reception or dinner, but countries including Libya, Saudi Arabia and Bahrain were among those invited by UKTI to attended the Farnborough event.

And we know that 16 months earlier, in March 2009, the Duke of York made a special presentation during a visit to Riyadh to one Mohammed Fehri Al Qahtani, BAE Systems' "man of the year" for 2008. Readers will recall that the Serious Fraud Office courted controversy in 2006 when it decided to halt an investigation into alleged kickbacks paid out by BAE Systems to a member of the Saudi royal family as part of the £43bn al-Yamamah arms deal with Saudi Arabia.

The al-Yamamah deal is famously alluded in another WikiLeaks cable, published in November 2010. Tatiana Gfoeller, the US ambassador to Kyrgyzstan, describes attending a brunch to brief Prince Andrew ahead of his meetings with the country's prime minister. She writes that the prince "railed at British anti-corruption investigators, who had had the 'idiocy' of almost scuttling the Al-Yamama deal with Saudi Arabia".

Blurring the dividing line
In the same cable, the prince describes himself as "a frequent visitor to Central Asia and the Caucasus". Recent reports have highlighted his links with President Akiyev of Azerbaijan and Timur Kulibayev, son-in-law of Kazakhstan's President Nazarbayev. Last April Kairat Kelimbetov, head of Kazakhstan’s Samruk-Kazyna sovereign wealth fund, claimed that Prince Andrew "expressed his readiness to help organise meetings with business circles in Britain".

At this point, the dividing line between the Duke of York's role as a UK trade representative and his personal life begin to blur. For Kulibayev, as well as being a bastion of energy-rich Kazakhstan's oligarchy, has admitted that he bought Sunninghill Park, the Duke and Duchess of York's former home near Ascot and a wedding present from the Queen, in 2007.

Although the property has remained unoccupied since then, Kulibayev bought it for £15m - £3m above the asking price at which it had been on the market for several years before 2007.

The sale of Sunninghill Park was carried out privately via the royal household and the Queen's solicitors. But the deal was brokered by Goga Ashkenazi, an Oxford-educated Kazakh who is also the mother of a child by Timur Kulibayev. Ms Ashkenazi defended Prince Andrew's business links in an interview with the London Evening Standard on 8 March, stating "Andrew is not the only one to have beaten a path to the door of dodgy dictators."

Meanwhile, Prince Andrew's relationship with his former wife, the Duchess of York, has continued to provide tabloid fodder since their marriage in 1986.

In May 2010 the duchess was filmed in a News of the World sting, suggesting to a reporter posing as an Indian businessman that a £500,000 payment could "open doors" via Prince Andrew. In a subsequent statement, she stressed that the Duke of York had not been aware or involved in the discussions she had had.

It then emerged that Jeffrey Epstein, a convicted paedophile and long-standing friend of the prince, had helped the Duchess of York to pay off part of one of her debts – allegedly at Prince Andrew's behest. A contrite duchess apologised for "a gigantic error of judgement" and restated her admiration for her former husband, "the man I admire most in the world".