Bioadvantaged Nylon: Polycondensation of 3-Hexenedioic Acid with Hexamethylenediamine

Bioadvantaged Nylon: Polycondensation of 3-Hexenedioic Acid with Hexamethylenediamine

(DIV) Iowa State University researchers have developed a flexible pathway to turn glucose into nylon or PET using inexpensive catalysts and moderate reaction conditions.
Abstract: 
(DIV) Using a combination of biological, electrochemical, and catalytic processes, ISU researchers have developed a pathway to convert glucose into precursors for both nylon and PET manufacture. The first phase utilizes an engineered strain of Saccharomyces cerevisiae to produce high levels of muconic acid from a glucose feedstock (a titer of 752mg/L). Next, muconic acid can be partially hydrogenated to hexenedioic acid or fully hydrogenated to adipic acid via an electrochemical process. Both hexenedioic acid and adipic acid can be combined with hexaminediamine to make Nylon 6,6. If hexenedioic acid is used in the nylon backbone, the remaining double bond can be further modified using controlled radical polymerization to create a functionalized nylon with potential applications in packaging and other areas. Alternately the muconic acid can undergo a series of reactions to produce terephthalic acid (one of the building blocks for PET, the most common thermoplastic polyester). These steps include electrocatalytically isomerizing the cis,cis- or cis,trans- muconic acid to the trans,trans- variant for PET and other high-value chemical production. This suite of technologies enables the production of a variety of similar polymers with different physical characteristics that can be targeted toward specialized end products. (DIV) This technology is related toISURF #4289: Electrocatalytic Hydrogenation of Muconic Acid for the Production of Biorenewable Synthetic Polymer Precursors, andISURF #4402: Electrochemical Isomerization of Muconic Acid (DIV)
Benefits: 
(DIV) -• Eliminates the use of petrochemicals in the production of a wide array of commonly used industrial and consumer products -• Tunable at several steps to produce similar polymers with different physical characteristics -• Inexpensive catalysts, moderate reaction conditions and high conversion rates -• Flexible pathway between nylon and PET -• Biomass byproducts have additional market value (DIV)
applications: 
Internal Laboratory Ref #: 
4357
Lab Representatives
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