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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #340668

Research Project: Industrial Monomers and Polymers from Plant Oils

Location: Bio-oils Research

Title: Bio-based production of methacrylic acid

item LANSING, JAMES - Orise Fellow
item Moser, Bryan
item Murray, Rex

Submitted to: Great Lakes Regional American Chemical Society Symposium
Publication Type: Abstract Only
Publication Acceptance Date: 5/17/2017
Publication Date: 6/27/2017
Citation: Lansing, J.C., Moser, B.R., Murray, R.E. 2017. Bio-based production of methacrylic acid [abstract]. American Chemical Society Great Lakes Regional Meeting, Sustainable Polymers section, GLRM 24, June 27-30, 2017, Fargo, ND. p. 4.

Interpretive Summary:

Technical Abstract: Methacrylic acid (MAA) is an important industrial chemical commodity, with annual production exceeding 3 million metric tons and a market value surpassing $9 billion. The primary use of MAA is the conversion to ester derivatives, which are further converted into numerous useful polymers. Despite the usefulness of MAA, the two main synthetic routes of generation (acetone cyanohydrin process and the direct oxidation of isobutylene) suffer from numerous drawbacks, including harsh toxic reagents and the generation of low value byproducts. We report a bio-based route to MAA via selective decarboxylation of itaconic acid utilizing catalytic ruthenium carbonyl propionate in an aqueous solvent system. High selectivity (> 90%) was achieved at low catalyst loading (0.1 mol %) with high substrate concentration (5.5 M) at low temperature (200–225 deg C) and pressure (less than or equal to 425 psig) relative to previous contributions in this area. Direct decarboxylation of itaconic acid was achieved as opposed to the conjugate base reported previously, thereby avoiding basification and acidification steps. Neither carbon monoxide nor propylene (excessive decarboxylation) were detected during ruthenium-catalyzed decarboxylation. In addition, co-solvents such as tetraglyme lowered vapor pressures within the reaction vessel by > 100 psig while minimizing decomposition of starting acids. In combination, these findings represent improvements over existing methodologies that may facilitate sustainable production of MAA, an important petrochemically-based monomer for the plastics industry.