A Greener Route to Nylon Production

Winner: 2024 Environment, Sustainability and Energy Horizon Prize: John Jeyes Prize

For the effective decoupling of the synthesis of the major commodity chemical cyclohexanone oxime from industrial hydrogen peroxide production.

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A Greener Route to Nylon Production is a collaboration led by Cardiff University, UBE Corporation, and Shanghai Jiao Tong University, with contributions from the Research Complex at Harwell, the University of Bath and Lehigh University.

Every year, nearly 2.5 million tons of hydrogen peroxide (H₂O₂) is used to upgrade the raw materials (feedstocks) used in chemical manufacturing. A long-standing goal of catalysis has been to replace preformed H₂O₂ with that generated in situ for chemical synthesis. But a combination of catalyst deactivation, poor selectivity and low yields, has prevented the adoption of such approaches.

However, the team’s research offers a breakthrough for producing cyclohexanone oxime, a crucial intermediate in the synthesis of Nylon-6. They have created a series of catalysts, based on bifunctional Pd/TS-1, that can generate H₂O₂ in situ, using readily available feedstocks, and produce cyclohexanone oxime at the same time.

This new process bridges the gap between the highly different conditions required for the individual reactions pathways. The performance of this new method is excellent, achieving close to 100% yield (meaning almost all the starting materials turn into the desired product) and minimal waste.

The adoption of this technology paves the way for cleaner, more efficient chemical production by generating H₂O₂ where it is needed. And, existing infrastructure can likely be adapted to use the technology, lowering the barrier to industrial adoption.

This work represents a positive first step towards more sustainable selective chemical transformations and has the potential to supersede the current industrial route to cyclohexanone oxime production.

The team

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Liwei Chen, Distinguished Professor, Shanghai Jiao Tong University

Tomas E. Davies, Experimental Officer in Electron Microscopy, Cardiff Catalysis Institute, Cardiff Univeristy

Jennifer K. Edwards, Senior Lecturer in Catalytic and Physical Chemistry, Cardiff Catalysis Institute, Cardiff Univeristy

Simon J. Freakley, Lecturer, University of Bath

Yukimasa Fukuta, General Manager, UBE Corporation

Graham J. Hutchings, Regius Professor of Chemistry, Cardiff Catalysis Institute, Cardiff Univeristy

Christopher J. Kiely, Harold B. Chambers Senior Professor, Lehigh University

Richard J. Lewis, Research Associate, Cardiff Catalysis Institute, Cardiff University

Xi Liu, Distinguished Professor, Shanghai Jiao Tong University/Ningxia University

David J. Morgan, Surface Analysis Manager, Cardiff Catalysis Institute, Cardiff Univeristy

Charlie B. Paris, Reseach Student, Cardiff Catalysis Institute, Cardiff Univeristy

Jizhen Qi, Reseach Student, Suzhou Institute of Nano-Tech and Nano-Bionics

Tian Qin, Reseach Student, Shanghai Jiao Tong University

James Singelton, Reseach Student, Cardiff Catalysis Institute, Cardiff Univeristy

Alex Stenner, Reseach Student, Cardiff Catalysis Institute, Cardiff Univeristy

Kenji Ueura, Manager, UBE Corporation

Yasushi Yamamoto, General Manager, HighChem Tokyo R&D CENTER LTD

Q&A

Example person

What were the biggest challenges in this project?

Richard Lewis: The biggest challenge that this project faced was in the design and synthesis of catalytic materials that were able to overcome the broad conditions gap that exists between the two key reaction pathways (i.e. the direct synthesis of hydrogen peroxide and the synthesis of the Nylon precursor) while also demonstrating excellent stability under conditions that promoted deactivation of active sites.

What different strengths did different people bring to the team?

Jenny Edwards: The steer of our industrial collaborators was critical to make sure we could integrate the two catalytic pathways to be a commercially viable solution. In doing so, the catalysts themselves became much more complex and so the skills of our materials characterization team were critical to understand how the catalyst performed.

Why is this work so important and exciting?

Richard Lewis: This breakthrough technology represents the first major decoupling of industrial H2O2 production from chemical synthesis, allowing for significant decarbonization of an existing industrial chemical process. It is a clear demonstration that significant improvements in current state-of-the-art technologies can be made and will hopefully contribute to the chemical synthesis sectors' declared sustainability goals.

Where do you see the biggest impact of this technology/research being?

Richard Lewis: We foresee this technology being implemented at scale, which would represent a significant step towards more efficient production of a major commodity chemical. More broadly, we hope that this work will inspire others to challenge existing paradigms and, through collective efforts, aid in the transition of the chemical synthesis sector towards more sustainable processes.

How will this work be used in real life applications?

Richard Lewis: We envisage this technology as a drop-in replacement for existing industrial routes to Nylon, allowing for improved process efficiencies in production and the decarbonization of a major commodity chemical.

How do you see this work developing over the next few years, and what is next for this technology/research?

Richard Lewis: Currently planning is underway for the evaluation of this technology beyond the laboratory scale. We’re also investigating the applicability of the in situ approach in the valorization of a range of other chemical feedstocks. Until now, the high cost of preformed H2O2 has been a major hurdle to commercial progression. However, through effective in situ production of the oxidant, considerable cost reductions may be achieved, which, when coupled with the improved environmental credentials of our technology, improves commercial viability.

What inspires or motivates your team?

David Morgan: The expanding roles of catalysis in everyday application is always exciting, but from a personal perspective, it’s the challenge of unravelling and understanding the complexities of the materials we produce.

What is the importance of collaboration in the chemical sciences?

Alex Stenner: As an early career scientist, collaboration is paramount from both a personal and collective perspective. This project has provided the opportunity to work with a diverse team of talented and knowledgeable individuals, which has been an incredibly valuable learning experience which I will take forward throughout my career.

What does good research culture look like or mean to you?

Jenny Edwards: Where there are no barriers to inclusion, and each and every person has the opportunity to contribute their expertise. Individuals are recognized for their contributions in an environment that is supportive of a healthy work-life balance.

How are the chemical sciences making the world a better place?

Richard Lewis: From the development of effective medicines and the production of materials we all rely on daily to the development of sustainable fuels, new energy sources and reversing environmental damage and decline, without the chemical sciences, the modern world simply would not exist.

What advice would you give to a young person considering a career in chemistry?

Richard Lewis: Don’t be afraid to question existing paradigms. Scientific discovery is driven by individuals and teams that are willing to explore heterodox approaches to challenges, including those that the community considers solved. Also, recognize that success isn’t always measured in the same timeframe or by the same metrics for everyone.