Successfully catalyzed a ‘forbidden’ product

This week a study is published in the journal Nature Catalysis explaining how to obtain a product so far ‘banned’ from Mizoroki-Heck reactions. Palladium catalysts are used to create carbon-carbon bonds and organic molecules of great industrial interest. The 2010 Nobel Prize in Chemistry recognized its development.

The authors of the work are scientists from the Institute of Chemical Technology (ITQ, mixed center of the CSIC and the Polytechnic University of Valencia), in collaboration with other researchers from this university and from Cádiz.

A new alkene, a molecule similar to that of oleic acid in olive oil, has been obtained using a different catalyst than the current one, which reduces costs up to 100 times and opens up a range of possibilities for its industrial application.

The product is a new alkene, a molecule similar to that of oleic acid in olive oil, and has been achieved using a catalyst other than the one used up to now, which reduces the price of obtaining it by up to 100 times and opens up a new range of possibilities for its use by the industry.

The Mizoroki-Heck reactions were described in the 1970s to create complex organic compounds that bound together carbon atoms, the chemical element on which life on Earth is based. Is it so palladium catalyzed and today they are used throughout the world, both in research and to produce drugs, as well as in the electronics industry, for example to manufacture organic LEDs.

However, this chemical reaction has a fundamental limitation: it consistently produces a single product, an alkene also known as a ‘beta product’. Alkenes are unsaturated hydrocarbons that have a double bond between carbon atoms that give them certain properties. For example, the famous unsaturated fats that help with ‘good cholesterol’ are alkenes.

Thus, the Mizoroki-Heck reaction so far produced only one type of alkene, and, although theoretically possible, it ‘prohibited’ the production of another alkene named ‘alpha product‘.

Obtaining the new alkene with a Mizoroki-Heck reaction. / ITQ (CSIC-UPV)

What the team has now achieved is to develop a new method to produce this alpha product from the Mizoroki-Heck reaction. To do this, they use a new palladium catalyst, which can also be liquid or solid and is not consumed in the reaction. In this case it is a zeolite, mineral widely used as a catalyst in the petrochemical industry.

New opportunities for the industry

“Obtaining this alpha product through a new catalyst greatly speeds up the process, a discovery that opens up new industrial possibilities for this reaction”, explains one of the authors, Antonio Leyva Pérez, of the ITQ.

Tamoxifen, the drug used against breast cancer after surgery and chemotherapy, could be made with this new molecule

The new product is also an alkene and has a carbon double bond, but its structure is different, which gives it different properties. In addition, obtaining it through a cheaper catalyst means that the price of obtaining one kilogram of this molecule is reduced by up to a hundred times in the way that until now it has been possible to obtain the ‘alpha product’, where palladium was consumed in the process.

Among its applications, Leyva explains that tamoxifen, the drug used against breast cancer after surgery and chemotherapy, it could be made with this new molecule. Also, it could be used in cosmetic or to get new polymers.

Reference:

Francisco Garnes-Portolés, Antonio Leyva-Pérez et al. “Regioirregular and catalytic Mizoroki – Heck reactions”. Nature Catalysis, 2021

Fountain: CSIC / UPV

Rights: Creative Commons.