Researchers at University of California at Berkeley have discovered a mild and relatively inexpensive procedure for removing oxygen from biomass. Nature, life and the future depend on science getting a much better grasp on the hydrogen, oxygen and carbon bonds.  Starting with the H2O splitting of water issue and ending in a very long list of complex molecules made of hydrogen, oxygen and carbon, getting the excess oxygen out is a matter of intense interest and has been so for decades.

Formic Acid Mediated Deoxygenation. Click image for more info.

Formic Acid Mediated Deoxygenation. Click image for more info.

Berkeley’s new procedure, if it can be effectively industrialized, could allow many of today’s petrochemical products, including plastics, to be made from biomass.  Robert Bergman, a co-principal investigator on this project who holds a joint appointment with Berkeley Lab’s Chemical Sciences Division and the UC Berkeley Chemistry Department says, “We’ve found and optimized a selective, one-pot deoxygenation technique based on a formic acid treatment.”  In the process formic acid converts glycerol, a major and unwanted by-product in the manufacturing of biodiesel, into allyl alcohol, which is used as a starting material in the manufacturing of polymers, drugs, organic compounds, herbicides, pesticides and other chemical products. Allyl alcohol today is produced from the oxidation of petroleum.

Jonathan Ellman, UC Berkeley chemistry professor and the other principal investigator in this research says, ““Right now, about five percent of the world’s supply of petroleum is used to make feedstocks that are synthesized into commodity chemicals. If these feedstocks can instead be made from biomass they become renewable and their production will no longer be a detriment to the environment.”  Well, not quite.  The disposal of the used plastic for example, still needs addressed.  I admit that plastics, bags and other containers are getting to be a serious trash problem.  And I am getting tired of picking up other’s trash, especially when it lasts for nearly an eternity.

Biomass holds most attention for its potential to be converted into carbon-neutral biofuels.  Yet there is also huge potential for it to be converted into chemical feedstocks.  Unlike petrochemical feedstocks, which are made by adding oxygen to petroleum, and fuels that are usually oxygen free unlike oxygen rich alcohols, biomass feedstocks require the removal of oxygen from the raw materials and alcohols that could be petrochemicals when the oxygen is removed.  Some products will be biodegradable, which is good news, too.

The story is Bergman and Ellman, working with Elena Arceo, a Fulbright scholar from Spain, and Peter Marsden, a UC Berkely graduate student, used labeling experiments and a unique distillation system to take a new look at an old chemical reaction in which formic acid was used to remove oxygen from glycerol. In its original conception, the reaction was low-yielding, primarily because of substantial charring, an unselective combustion that leads to an intractable mixture under high heat. Bergman and Ellman found that simply protecting this reaction from air provided a much-improved process for the deoxygenation of glycerol.

Bergman notes, “Treating glycerol with formic acid while directing a stream of nitrogen through the reaction mixture completely eliminates charring. Besides protecting the product from atmospheric oxidation, the nitrogen also facilitates distillation of the alcohol. The final product shows substantially improved yield (80-percent) and higher selectivity.”

Ellman concludes with, “From our studies we also gained a much better understanding of the basic chemistry behind the reaction. We thought that the charring was a random oxidation process because the reaction had been carried out in air and we expected that running it in a nitrogen environment would improve things. However, in studying the basic chemistry we uncovered an unexpected reaction pathway that really broadens the generality of this reaction and expands its potential applications.”

In the new reaction pathway, the formic acid-mediated deoxygenation technique could be used to convert the carbohydrates in biomass, as well as other polyhdroxy compounds, into the chemical feedstocks, such as olefins (alkenes) that are now derived from petroleum. The technique should also prove useful in the process by which biomass is converted into liquid transportation fuels.

Bergman instructs that the breakthrough needs engineering to go to commercial scale saying, “Our preliminary results with inexpensive biomass-derived polyols suggest that the reaction of polyhydroxy compounds with formic acid will be a valuable alternative for the manufacture of reduced oxygen content products. However, scaling this technique up so that biomass feedstocks are competitive with feedstocks derived from petroleum is going to be an engineering challenge.”

Ellman adds, “Scaling the technique up to industrial levels is probably going to require the combined efforts of industrial and academic laboratories, but if we are able to one day make commodity chemicals as well as fuels from biomass, we can protect the atmosphere from further damage and at the same time help lower current carbon dioxide levels.”

This work is just now past conception stage with great potential.  Oxygen is one of three main life chemicals and its presence has bedeviled chemists for decades in reforming molecules to other forms.  Getting it in has proven much easier than getting it out, so these developments are quite important.  Bergman’s site is this link and Ellman’s is here.


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