Environmental analysis of the life cycle emissions of 2-methyl tetrahydrofuran solvent manufactured from renewable resources

Abstract

An environmental analysis has been conducted to determine the cradle to gate life cycle emissions to manufacture the green solvent, 2-methyl tetrahydrofuran. The solvent is considered a greener chemical since it can be manufactured from renewable resources with a lower life cycle footprint. Analyses have been performed using different methods to show greenness in both its production and industrial use. This solvent can potentially be substituted for other ether and chlorinated solvents commonly used in organometallic and biphasic reactions steps in pharmaceutical and fine chemical syntheses. The 2-methyl tetrahydrofuran made from renewable agricultural by-products is marketed by Penn A Kem under the name ecoMeTHF™. The starting material, 2-furfuraldehyde (furfural), is produced from corn cob waste by converting the available pentosans by acid hydrolysis. An evaluation of each step in the process was necessary to determine the overall life cycle and specific CO2 emissions for each raw material/intermediate produced. Allocation of credits for CO2 from the incineration of solvents made from renewable feedstocks significantly reduced the overall carbon footprint. Using this approach, the overall life cycle emissions for production of 1 kg of ecoMeTHF™ were determined to be 0.191 kg, including 0.150 kg of CO2. Life cycle emissions generated from raw material manufacture represents the majority of the overall environmental impact. Our evaluation shows that using 2-methyl tetrahydrofuran in an industrial scenario results in a 97% reduction in emissions, when compared to typically used solvents such as tetrahydrofuran, made through a conventional chemical route.

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“…In fact, MTHF has many benefits to THF as a solvent including immiscibility with water, lower volatile organic compound (VOC) emissions, and improved results in a variety of applications, particularly in the pharmaceutical industry . Furthermore, a life cycle analysis of the production of MTHF from furfural showed a 97% reduction in emissions compared to the current industrial route to make THF . THP also shows potential as a green alternative to THF or 1,4‐dioxane, having similar properties with the exception of its limited solubility in water, which could be advantageous in liquid‐liquid separation processes…”

Out-smarting smart drug modafinil through flow chemistry

“…The solvent selected, 2-methyltetrahydrofuran, although still lacking classification by pharmaceutical regulatory boards such as the FDA, is a significantly greener option. 61 In this regard, the process reported here relies entirely on class 3 FDA solvents, i.e., solvents recognized for the low toxic potential thus facilitating the straightforward application of our work to the industrial setting. 52 Another important consideration to determine the practicality of a synthesis is cost.…”

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

“…2-Methyltetrahydrofuran, see Figure 11 , is an ethereal solvent that can be derived from renewable resources such as levulinic acid or furfural, 153 which can themselves be derived from agricultural waste such as corn stover, sugar cane bagasse, and rice straw. 154 Life cycle assessment conducted on 2-MeTHF has shown that production of the solvent from furfural derived from corn-cob waste can reduce emissions by up to 97% when compared to a traditional chemical synthesis of THF, 155 though it is not always clear how individual supplies of 2-MeTHF are currently made. Structurally, 2-MeTHF differs from THF by the addition of one single methyl group, yet this addition is responsible for several significantly different physiochemical properties.…”