Topics in Catalysis

, Volume 57, Issue 17–20, pp 1325–1334 | Cite as

Challenges in Catalytic Manufacture of Renewable Pyrrolidinones from Fermentation Derived Succinate

  • James F. White
  • Johnathan E. Holladay
  • Allan A. Zacher
  • John G. FryeJr.
  • Todd A. Werpy
Original Paper

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.

Keywords

Succinic acid Hydrogenation N-Methyl succimide N-Methyl-2-pyrrolidinone 2-pyrrolidinone Renewable resources 

References

  1. 1.
    Werpy TA, Peterson G (2004) Top value added chemicals from biomass, US Dept. of EnergyGoogle Scholar
  2. 2.
    Zeikus JG, Jain MK, Elankovan P (1999) Appl. Biotechnol. 51:545CrossRefGoogle Scholar
  3. 3.
    Rodgers P, Chen JS, Zidwick MJ (2006) Prokaryotics (Chap. 3.1) 1:511Google Scholar
  4. 4.
    Guettler MV, Mahendrak J. US Patent 5,573,931 to Michigan Biotechnology InstituteGoogle Scholar
  5. 5.
    Rathin D. US Patent 5,143,833 to Rathin DataGoogle Scholar
  6. 6.
    Glassner D, Rathin D. US Patent 5,143,834 to the inventorsGoogle Scholar
  7. 7.
    Rathin D, Glassner D. US Patent 5,168,055 to the inventorsGoogle Scholar
  8. 8.
    Burglund KA, Yedur S. US Patent 5,958,744 to ACCGoogle Scholar
  9. 9.
    Fruchey OS, Manzer LE. USA patents 8084626, 8466300, and 2013/0184492 to BioAmberGoogle Scholar
  10. 10.
    Werpy TA, Holladay JE, Frye JG (2006) Biorefineries-industrial processes and products: status quo and future directions (Chap. 13), vol. 2. Wiley, Weinheim, p. 367Google Scholar
  11. 11.
    Frye JG, Zacher AH, Werpy TA, Wang Y (2005) Catalysis of organic reactions (Chap. 17), vol. 104. Taylor & Francis, Sowa, p. 145Google Scholar
  12. 12.
    Nghiem N, Davison BH, Donnelly MI, Tsai S (2001) ACS Symp Ser 748:160CrossRefGoogle Scholar
  13. 13.
    Werpy TA Frye JG. US Patent 6,706,893 to BattelleGoogle Scholar
  14. 14.
    Olson RJ. US Patents 4,814,464, 4,841,069 to AmocoGoogle Scholar
  15. 15.
    Tosukhowong T, Roffi K. WO2013033649A1 to Myriant Corp.Google Scholar
  16. 16.
    Werpy TA, Frye JG, White JF, Holladay JE, Zacher AH. US Patents 7,199,250, 7,674,916, 7,973,177, 8,501,963 to BattelleGoogle Scholar
  17. 17.
    Elliott DC, Peterson KL, Muzatko DS, Alderson EV, Hart TR, Neuenschwander GG (2004) Appl Biochem Biotechnol 115:807CrossRefGoogle Scholar
  18. 18.
    Werpy TA, Frye JG, Wang Y, Zacher AH (2007) US Patents 6603021, 6632951 and 6706893 to BattelleGoogle Scholar
  19. 19.
    Liu KC, Taylor PD. US Patent 4824967 to GAF Corp.Google Scholar
  20. 20.
    Werpy TA, Frye JG, White JF, Holladay JE, Zacher AH. EP1572644 to BattelleGoogle Scholar
  21. 21.
    Cerny M et al (1969) Collect Czech Chem Commun 34:1033CrossRefGoogle Scholar
  22. 22.
    Kertes AS, King CJ (1986) Biotechnol Bioeng 28:269CrossRefGoogle Scholar
  23. 23.
    Kirsch T, Maurer G (1996) Ind Eng Chem Res 35:1722CrossRefGoogle Scholar
  24. 24.
    Li Z, Qin W, Dai Y (2002) J Chem Eng Data 47:843CrossRefGoogle Scholar
  25. 25.
    Haas T, Tacke T, Schraver A. US 2011/0118504Al and references within to EvonikGoogle Scholar
  26. 26.
    Cockrem MCM. US 6291708 to A.E. StaleyGoogle Scholar
  27. 27.
    Joglekar HG, Rahman I, Babu S, Kulkarni SD, Joshi A (2006) Separat Purif Technol 52:1CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • James F. White
    • 1
  • Johnathan E. Holladay
    • 2
  • Allan A. Zacher
    • 2
  • John G. FryeJr.
    • 2
  • Todd A. Werpy
    • 3
  1. 1.3RiversCatalysis, LLCRichlandUSA
  2. 2.Pacific Northwest National LaboratoryRichlandUSA
  3. 3.JRR Research CenterArcher-Daniels-MidlandDecaturUSA

Personalised recommendations