Ash Influence on the Ethyl Levulinate Production from Sugarcane Molasses Mediated by Taurine Hydrogen Sulfate

Author(s)

Gomes, Gustavo Rodrigues ^[1] ; Breitkreitz, Marcia Cristina ^[1] ; Pastre, Julio Cezar ^[1]

Affiliation

^[1] Univ Campinas UNICAMP, Inst Chem, BR-13083970 Campinas, SP - Brazil

• Document type: Journal article
• Source: ACS SUSTAINABLE CHEMISTRY & ENGINEERING; v. 9, n. 40, p. 13438-13449, OCT 11 2021.
• Web of Science Citations: 0

Abstract

Ethyl levulinate (EL) is an important biobased building block obtained from a sugar platform to produce chemicals, pharmaceuticals, solvents, plasticizers, and biofuels. In this work, a biobased amino acid derivative, taurine hydrogen sulfate, was applied as a Bronsted-acid catalyst for the conversion of sugarcane molasses to ethyl levulinate under microwave irradiation. Experimental designs were carried out for the three main carbohydrates present in the molasses (fructose, sucrose, and glucose), and under the optimized conditions, EL was obtained in 76% yield from fructose (180 degrees C, 60 min, Cat. 5 mol %), 54% yield from sucrose (180 degrees C, 60 min, Cat. 40 mol %), and 53% yield from glucose (180 degrees C, 120 min, Cat. 100 mol %). A control experiment using a synthetic medium showed that EL could be obtained in up to 80% yield at 180 degrees C for 2 h with 100 mol % taurine hydrogen sulfate. However, EL yields were extremely low (5%) at the same conditions using the raw feedstock, the drop in the yield correlating with the inorganic matter (ashes) content of the molasses. Several adsorbents were tested, and Dowex 50WX2 exhibited the best performance to remove the ash content. Indeed, two sequential percolations could reduce the ashes from 7.5% to 0.25%, resulting in a matrix able to produce EL in 82% yield, completely eliminating the matrix effect observed for sugarcane molasses. Our findings could be useful for other applications including the use of this abundant raw material for the preparation of other key industrial intermediates. (AU)

• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 20/11578-7 - Enabling technologies allied to green chemistry: synthesis of high value-added compounds from biomass derivatives
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Regular Program Grants
• FAPESP's process: 18/09861-2 - Synthesis of novel ionic liquids from renewable sources and application on biomass conversion
• Grantee: Gustavo Rodrigues Gomes
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 14/26378-2 - Development of methodologies and synthetic processes employing a new technological platform: micro and meso reactor assisted synthesis of natural products and derivatives with potential pharmacological activity
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Research Grants - Young Investigators Grants