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Challenges in Catalytic Manufacture of Renewable Pyrrolidinones from Fermentation Derived Succinate

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Abstract

Fermentation derived succinic acid ammonium salt is an ideal precursor for manufacture of renewable N-methyl pyrrolidinone (NMP) or 2-pyrrolidinone (2P) via heterogeneous catalysis. However, there are many challenges to making this a practical reality. Chief among the challenges is avoiding catalyst poisoning by fermentation by- and co-products. Battelle/Pacific Northwest National Laboratory have developed an effective technology strategy for this purpose. The technology is a combination of purely thermal processing, followed by simple catalytic hydrogenation that together avoids catalyst poisoning from fermentation impurities and provides high selectivity and yields of NMP or 2P.

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Notes

  1. Succinic acids: advances in research and applications—a scholarly brief—see 2011 Editions and also the Jan 9 2012, Dec 26 2012, and June 21 2013 editions, Ashton Acton, Ed., published by ScholarlyBriefs®, Atlanta, GA.

  2. Private discussions with various researchers.

  3. Private communications with a commercial producer of renewable succinic acid.

  4. Unpublished Battelle Internal Technical Report, NMP Commercialization Phase I, (5-2003)—a proprietary publication by Battelle/PNNL staffs.

  5. Unpublished results from CRADA # 96-0407, Administered by Oak Ridge National Laboratory, US Department of Energy Alternate Feedstock Program. (available from Oak Ridge).

  6. Definition: peptone = any of various water-soluble compounds (and mixtures) that form by hydrolysis of proteins to amino acids, http://en.wikipedia.org/wiki/Peptone#Peptide_classes.

  7. Private discussions with Evonik and Engelhard (now BASF) staffs.

  8. Also observed by PNNL staff via titration curves of succinic acid aqueous solutions with ammonium hydroxide.

  9. Applied CarboChemicals evolved into Diversified Natural Products (DNP and is now known as BioAmber.

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Acknowledgements

We would like to thank the US Department of Energy, Energy Efficiency and Renewable Energy Office, Battelle Memorial Institute and Archer-Daniels-Midland for financial support. In addition, we acknowledge the technical efforts and activities of E. V. Alderson, M. Butcher, T. Hart, D. S. Muzatko, D. L. Stiles, C. F. Wend and Dr. Y. Wang during various portions of this project. We also thank Battelle Memorial Institute for permission to publish.

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Correspondence to James F. White.

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White, J.F., Holladay, J.E., Zacher, A.A. et al. Challenges in Catalytic Manufacture of Renewable Pyrrolidinones from Fermentation Derived Succinate. Top Catal 57, 1325–1334 (2014). https://doi.org/10.1007/s11244-014-0299-z

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