272116 Catalytic Valorization of Isosorbide As Versatile Renewable Platform Chemical

Tuesday, October 30, 2012: 8:30 AM
322 (Convention Center )
Marcus Rose, Rebecca Pfützenreuter, Katharina Thenert and Regina Palkovits, RWTH Aachen University, Aachen, Germany

Catalytic Valorization of Isosorbide as Versatile Renewable Platform Chemical

Marcus Rose, Rebecca Pfützenreuther, Katharina Thenert, Regina Palkovits
RWTH Aachen University, Aachen, Germany

The substitution of fossil resources in the production of crude oil-based products such as polymers or fuels by renewable lignocellulosic biomass is essential in the future. Cellulosic feedstock such as straw, wood residues or other bio-waste can be converted by efficient catalytic processes to platform chemicals of great importance such as isosorbide.

Isosorbide poses great potential as an intermediate in the production of biofuels, fuel additives, high boiling solvents, surfactants and polymers. Thus, the development of catalytic processes for a highly efficient isosorbide conversion is crucial. Main target is the functionalization or substitution of the two hydroxyl groups maintaining the cis-fused ditetrahydrofurane scaffold. Numerous investigations on feasible isosorbide transformation routes have been reported in the middle of the 20th century. Nowadays, two isosorbide derivatives are already commercially available. Isosorbide nitrates are used in medicine as vasodilating pharmaceuticals, whereas isosorbide dimethyl ether gained interest as a versatile non-toxic pharmaceutical solvent. Several publications deal with the isosorbide functionalization via the Williamson etherification using alkyl halides. A disadvantage of this process is the formation of huge amounts of halogen containing side product. Alternatively, the etherification by telomerization with 1,3-butadiene has been shown recently, resulting in several isomeric products.

One focus of our work is the conversion of isosorbide to defined tert-butyl ether derivatives heterogeneously catalyzed by acidic ion exchange resins such as Amberlyst-15. Instead of the Williamson method, two different approaches, the condensation reaction of isosorbide with tert-butanol avoiding side products other than water as well as the addition of isosorbide hydroxyl groups to isobutene, have been investigated. In the reaction with tert-butanol an isosorbide conversion of 27 % was achieved due to the water formation shifting the equilibrium reaction to the side of the substrates. With isobutene close to full conversion of isosorbide was observed with up to 60 % yield of the diether and two different monoethers as by-products. In our current work we develop an energy efficient process for the continuous etherification of the biogenic platform chemical isosorbide with isobutene.

In this contribution we want to give a critical overview on the different aspects of isosorbide chemistry and feasible catalytic conversions as well as present recent results on the development of efficient processes for the etherification of isosorbide to produce novel value-added products such as green solvents and fuel additives.

Extended Abstract: File Not Uploaded
See more of this Session: Catalytic Biomass Conversion to Chemicals II
See more of this Group/Topical: Fuels and Petrochemicals Division