Iodine-Catalyzed Isomerization of Dimethyl Muconate

Settle, Amy E.; Berstis, Laura; Zhang, Shuting; Rorrer, Nicholas A.; Hu, Haiming; Richards, Ryan M.; Beckham, Gregg T.; Crowley, Michael F.; Vardon, Derek R.

doi:10.1002/cssc.201800606

Title: Iodine-Catalyzed Isomerization of Dimethyl Muconate

Journal Article · 16 April 2018 · ChemSusChem

DOI: https://doi.org/10.1002/cssc.201800606 · OSTI ID:1436570

^[1]; Berstis, Laura ^[2]; Zhang, Shuting ^[2];

^[2]; Hu, Haiming ^[2];

^[1];

^[2];

^[1]

National Renewable Energy Lab. (NREL), Golden, CO (United States); Colorado School of Mines, Golden, CO (United States)
National Renewable Energy Lab. (NREL), Golden, CO (United States)

Abstract cis,cis ‐Muconic acid is a platform bio‐based chemical that can be upgraded to drop‐in commodity and novel monomers. Among the possible drop‐in products, dimethyl terephthalate can be synthesized via esterification, isomerization, Diels–Alder cycloaddition, and dehydrogenation. The isomerization of cis , cis ‐dimethyl muconate ( cc DMM) to the trans , trans ‐form ( tt DMM) can be catalyzed by iodine; however, studies have yet to address (i) the mechanism and reaction barriers unique to DMM, and (ii) the influence of solvent, potential for catalyst recycle, and recovery of high‐purity tt DMM. To address this gap, we apply a joint computational and experimental approach to investigate iodine‐catalyzed isomerization of DMM. Density functional theory calculations identified unique regiochemical considerations owing to the large number of halogen‐diene coordination schemes. Both transition state theory and experiments estimate significant barrier reductions with photodissociated iodine. Solvent selection was critical for rapid kinetics, likely because of solvent complexation with iodine. Under select conditions, tt DMM yields of 95 % were achieved in <1 h with methanol, followed by high purity recovery (>98 %) with crystallization. Lastly, post‐reaction iodine can be recovered and recycled with minimal loss of activity. Overall, these findings provide new insight into the mechanism and conditions necessary for DMM isomerization with iodine to advance the state‐of‐the‐art for bio‐based chemicals.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio); National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1436570

Alternate ID(s):: OSTI ID: 1436543

Report Number(s):: NREL/JA-5100-71487

Journal Information:: ChemSusChem, Vol. 11; ISSN 1864-5631

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 15 works

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