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Cost-efficient, on-purpose 1,5-PDO from bio-based starting material

By Scott Jenkins |

Construction is underway on a demonstration plant for manufacturing 1,5-pentanediol (1,5-PDO) from bio-based furfural, a platform chemical that can be derived from plant-based hemicellulose sugars. The process under construction by the company Pyran Inc. (Madison, Wis.; www.pyranco.com) offers a lower-cost (by 40% below today’s market price, the company says) route to 1,5-PDO than that of the petroleum-derived 1,5-PDO analog. Additionally, it can be produced on purpose, rather than being obtained only as a byproduct of other processes, explains technology developer and Pyran co-founder Kevin Barnett.

“α,ω-diols are expensive to produce from petroleum feedstocks because they require a number of complex separations, selective oxidations and reductions,” says Barnett. “And 1,5-PDO is even more difficult because C5 petroleum feedstocks are not readily available in large quantities. That’s what makes the bio-based approaches attractive,” he says.

Pyran engineers developed a novel route to 1,5-PDO that lowers catalyst costs by almost 50 times compared to alternative bio-based 1,5-PDO processes, and lowers operating costs by seven times, despite having more reaction steps.

The process begins with the hydrogenation of furfural to make tetrahydrofurfuryl alcohol, which is converted to dihydropyran, a heterocyclic ring compound with a C=C double bond. The double bond is then hydrated to form 2-hydroxytetrahydropyran (2-HY-THP; figure). The 2-HY-THP undergoes a ring-opening tautomerization that forms an aldehyde (5-hydroxyvaleraldehyde) that can be hydrogenated over a specially adapted noble-metal catalyst to produce the 1,5-PDO in high yields.

The 1,5-PDO demonstration plant is currently being built in the Houston area as a toll-manufacturing operation, and will supply ton quantities of bio-based 1,5-PDO for customer qualification testing. The plant is expected to begin production in autumn 2021.

1,5-PDO is widely used in the coatings and adhesives segment. “Customers of 1,5-pentanediol have been restricted from using the performance-enhancing product because of cost, and petroleum-based capacity is constrained by co-product limitations,” says Mel Luetkens, who recently joined Pyran as CEO. “Pyran’s renewable, on-purpose production will enable customers to expand their businesses with better-performing and more sustainable products.”

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