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Diamondoids Can Be Refined From Crude Oil

Diamondoid was first discovered and isolated from a Czechoslovakian petroleum in 1933. The isolated substance was named adamantane, from the Greek for diamond. This name was chosen because it has the same structure as the diamond lattice, highly symmetrical and strain free. It is generally accompanied by small amounts of alkylated adamantanes: 2-methyl-; 1-ethyl-; and probably 1-methyl-; 1,3-dimethyl; and others.
by Charles Choi
New York (UPI) May 07, 2004
Oil giant ChevronTexaco has announced it can now refine from crude oil sizable quantities of diamond-like molecules that hold great potential for science and health researchers.

Chemists say the diamondoids, as they are called -- each less than a billionth of billionth of a carat in size -- could find their way into everything from advanced materials and microscopic devices to pharmaceuticals and jet fuel.

"These materials are clear, and at the same time very hard, so you could really think about making a clear, hard coating applied to many different things as protection and still see through to the surface below," researcher Bob Carlson, a ChevronTexaco organic chemist, told United Press International.

A diamond weighing 1 carat is a crystal made of billions of interlocking cages. Each cage, only nanometers or billionths of a meter in size, is identical to all the others and is made up of 10 carbon atoms. By itself, such a cage has atoms of hydrogen attached to its surface and is known as adamantane, from "adamas," the Greek word for diamond.

Adamantane was first discovered in 1933 in Czechoslovakian petroleum. After some biochemical experimentation, scientists found an adamantane derivative, called aminoadamantane, could fight viruses, apparently by interfering with the proteins germs use to infect cells.

By chance, doctors also found aminoadamantane could reduce shaking in Parkinson's disease when they gave it to a patient who also had the flu.

For years investigators puzzled over what adamantane's bigger siblings might be capable of doing. Although they learned to synthesize adamantane, fusing even a few such cages together proved extraordinarily difficult, and efforts at creating larger diamondoids failed.

In late 2002, ChevronTexaco scientists, who were studying certain oil and natural gas pipelines that had become clogged, revealed they had discovered 20 new flavors of diamondoids in crude oil from the Gulf of Mexico -- some with up to 11 cages stuck together. The molecules had the rigidity and stability of diamonds.

Then last year, ChevronTexaco launched Molecular Diamond Technologies, a business unit in Richmond, Calif., to produce, develop and commercialize diamondoids. The company now says it can manufacture gram quantities of the material and has made them available for research and development applications.

"We are on track with the scale-up plans announced last year," Carlson said, "and (we) invite parties interested in researching, developing applications and commercializing these materials to contact us."

Current research partners include nearly 10 labs nationally and internationally to determine properties of the diamondoids and investigate the best possible applications.

"We are in serious negotiations with three or four companies at this time for commercial agreements," Waqar Qureshi, vice president of ChevronTexaco Technology Ventures, told UPI.

For years, scientists for have salivated over the possibilities inherent in higher diamondoids -- those possessing four or more cages. The molecules come in a menagerie of shapes, from rods to disks to screws, and combine the useful properties of diamonds with the versatile chemistry of hydrocarbon molecules.

This makes them ideal building blocks for nanotechnology -- or machines at the nanometer scale. No fewer than 30 countries worldwide are investigating nanotechnology, with total revenues for nanotech-enabled products and services expected to surpass $1 trillion annually worldwide, according to analyst firm Frost & Sullivan in San Antonio.

"Having a pure nano-material produced in sufficient quantities is essential to the advancement of commercial application development," Qureshi said. "This is an important step in furthering advances in the fast-growing, actively funded field of nanotechnology."

The ChevronTexaco scientists have refined higher diamondoids from crude oil -- as well as kilogram quantities of the valuable lower diamondoids diamantane and triamantane, which possess two and three crystal lattice cages, respectively.

"Diamantane and triamantane can be synthesized in laboratories, but it's very difficult and very expensive," Qureshi said. "The cost of synthesizing these diamondoids is probably in the tens to hundreds of dollars per gram. But we can extract it for orders of magnitudes lower in cost."

Qureshi said his group is beginning a research and development effort with an institute to study pharmaceutical applications for the diamondoids.

"Simple chemical compounds such as aminoadamantane that can serve as antiviral agents are extremely rare, so there's always interest in that," Alan Marchand, an organic chemist retired from the University of North Texas in Denton, told UPI.

Because diamondoids can absorb substantial heat without breaking down, Marchand also speculated they could find use as fuel additives as well as be used in many other applications.

"The fact they are able now to dredge out grams of diamondoids opens areas of research otherwise closed," Marchand said. "This is a gift from heaven. What they're doing is extremely important. It's hard to say exactly where it will go, but people will be inclined to try things otherwise inaccessible."

Diamondoids are found in only trace levels in most oils, varying anywhere from a few parts per million to thousands of parts per million. Gallons of crude oil can yield anywhere from milligrams to grams of diamondoid, Carlson said.

The diamondoids are formed in the extreme heat and pressure found in crude oil buried at great depths, so petroleum deposits exposed to hotter temperatures should be enriched in the molecules, Carlson said, adding that gas condensates found in deposits rich in natural gas seem to be the best sources for diamondoids.

The researchers purify diamondoids at a ChevronTexaco facility where petroleum is distilled, heated and run past a chromatography machine -- the kind used in the pharmaceutical industry to separate out drug components.

"We went from a batch process, which would have been virtually impossible to make anything that could really be commercial out of that, to a continuous process," Qureshi said.

"We could scale up right now if we wanted. The approach we're taking is producing gram amounts of several different diamondoids, enough for research, and then when there are directions that look like they have commercial value, scale up to doing more."

All rights reserved. Copyright 2004 by United Press International. Sections of the information displayed on this page (dispatches, photographs, logos) are protected by intellectual property rights owned by United Press International. As a consequence, you may not copy, reproduce, modify, transmit, publish, display or in any way commercially exploit any of the content of this section without the prior written consent of by United Press International.

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