Water: the Solvent of Choice

May 16, 2005

Miscibility not required: chemical reactions "on water" faster than in organic solvents

We all know what it means to put something "on ice", but what is a chemical reaction "on water"? This new expression has been coined by a team headed by K. Barry Sharpless, winner of the 2001 Nobel Prize for chemistry, to describe reactions of organic substances that are not water-soluble, yet react well or even considerably faster in the presence of water than in organic solvents. If water could also replace organic solvents more often on the industrial scale, it would save money, increase the safety of chemical facilities, and reduce stress on the environment. Another advantage is that after the reaction, the organic and aqueous phases separate, eliminating the need for complex isolation steps to obtain the product.

Until now, a central aspect in the area of aqueous organic chemistry has been the effort to improve the water- solubility of the substances involved. Has this been the wrong approach? Is the axiom that has been passed on from the days of alchemy, corpora non agunt nisi soluta (substances do not interact with each other if they are not dissolved), no longer valid? Do reactants not need to be water-soluble at all in order to react in an aqueous environment? It seems that the situation bears some rethinking. Says Sharpless, "In contrast to prior assumptions, it seems that in many cases the immiscibility of the organic and aqueous phases is a considerable advantage."

So what exactly does "on water" mean? The expression simply refers to the fact that the reactants and the water are vigorously stirred together. This forms a suspension, meaning that the immiscible liquids are finely divided into tiny drops. The contact surface between the aqueous and organic phases is thus especially large.

Why certain important categories of reactions, such as the Claisen rearrangement, work so well in aqueous suspension is not yet clear. Particularly astonishing is the fact that the reactions occasionally go faster "on water" than in a mixture of the pure reactants (without any solvent). "Molecules at the interface between two different phases often behave differently than molecules within the phase." Sharpless speculates: "It is possible that the unique properties of molecules at the interface between the water and the hydrophobic, oily organic phase play an important role in speeding up the reactions."

Source: John Wiley & Sons, Inc.

Explore further: Researchers create methylation maps of Neanderthals and Denisovans, compare them to modern humans

add to favorites email to friend print save as pdf

Related Stories

Chemical products on a renewable basis

Feb 04, 2014

A breakthrough in the use of renewable raw materials in chemical production has been achieved by Karlsruhe Institute of Technology (KIT) and its industrial partner AVA Biochem: In January this year, a facility ...

Recommended for you

Study finds law dramatically curbing need for speed

Apr 18, 2014

Almost seven years have passed since Ontario's street-racing legislation hit the books and, according to one Western researcher, it has succeeded in putting the brakes on the number of convictions and, more importantly, injuries ...

Newlyweds, be careful what you wish for

Apr 17, 2014

A statistical analysis of the gift "fulfillments" at several hundred online wedding gift registries suggests that wedding guests are caught between a rock and a hard place when it comes to buying an appropriate gift for the ...

User comments : 0

More news stories

Clippers and coiners in 16th-century England

In 2017 a new £1 coin will appear in our pockets with a design extremely difficult to forge. In the mid-16th century, Elizabeth I's government came up with a series of measures to deter "divers evil persons" ...

Airbnb rental site raises $450 mn

Online lodging listings website Airbnb inked a $450 million funding deal with investors led by TPG, a source close to the matter said Friday.

Health care site flagged in Heartbleed review

People with accounts on the enrollment website for President Barack Obama's signature health care law are being told to change their passwords following an administration-wide review of the government's vulnerability to the ...