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Synthesis 2013; 45(12): 1683-1688
DOI: 10.1055/s-0033-1338478
paper
© Georg Thieme Verlag Stuttgart · New York

Preparation of a Nylon-11 Precursor from Renewable Canola Oil

Nicolas Daniel Spiccia
School of Chemistry, Monash University, Clayton 3800, Australia   Fax: +61(3)99054597   Email: andrea.robinson@monash.edu
,
Emily Border
School of Chemistry, Monash University, Clayton 3800, Australia   Fax: +61(3)99054597   Email: andrea.robinson@monash.edu
,
Jayamini Illesinghe
School of Chemistry, Monash University, Clayton 3800, Australia   Fax: +61(3)99054597   Email: andrea.robinson@monash.edu
,
William Roy Jackson
School of Chemistry, Monash University, Clayton 3800, Australia   Fax: +61(3)99054597   Email: andrea.robinson@monash.edu
,
Andrea Jane Robinson*
School of Chemistry, Monash University, Clayton 3800, Australia   Fax: +61(3)99054597   Email: andrea.robinson@monash.edu
› Author Affiliations
Further Information

Publication History

Received: 04 February 2013

Accepted after revision: 15 April 2013

Publication Date:
17 May 2013 (online)

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Dedicated to Professor David Cole-Hamilton on the occasion of his retirement and for his outstanding contribution to transition-metal catalysis

Abstract

We report a multi-catalytic sequence to a valuable nylon-11 precursor, methyl 11-aminoundecanoate, which is prepared by a ruthenium-catalysed cross-metathesis and a highly regioselective palladium-catalysed amination–hydrogenation reaction, from canola oil, a renewable, natural vegetable oil feedstock.

Key words

metathesis - hydrogenation - amination - catalysis - polymers - nylon-11 - canola - renewable

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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  • References

  • 1 Jenck JF, Agterberg F, Droesher MJ. Green Chem. 2004; 6: 544
    Crossref
  • 2 Gunstone FD, Hamilton RJ. Oleochemical Manufacture and Applications . CRC Press; Boca Raton: 2001
    Google Scholar
  • 3 Biermann U, Friedt W, Lang S, Lühs W, Machmüller G, Metzger JO, Rüsch gen Klaas M, Schäfer HJ, Schneider MP. Angew. Chem. Int. Ed. 2000; 39: 2206 ; Angew. Chem. 2000, 112, 2292
    CrossrefPubMed
  • 4 Biermann U, Bornscheuer U, Meier MA. R, Metzger JO, Schäfer HJ. Angew. Chem. Int. Ed. 2011; 50: 3854
    CrossrefPubMed
  • 5 Devaux, J.-F.; Le, G.; Pees, B. Application of Eco-Profile Methodology To Polyamide 11; http://legacy.arkema.com/pdf/EN/products/technical_polymers/rilsan/rilsan_website_2011/rilsan_eco-profile_article.pdf (accessed May 7, 2013).
  • 6 Bonner RM, Kohan MI, Lacey EM, Richardson PN, Roder TM, Sherwood JL. T In Nylon Plastics . Kohan MI. Wiley; New York: 1973: 327-408
    Google Scholar
  • 7 Kohan MI In Nylon Plastics . Kohan MI. Wiley; New York: 1973: 13-82
    Google Scholar
  • 8 Castor Oil India Comprehensive Castor Oil Report 2013; ; http://www.castoroil.in/downloads/download.php?name=Preview_of_Comprehensive_Castor_Oil_Report.pdf (accessed Mar 27, 2013)
  • 9 Audi J, Belson M, Patel M, Schier J, Osterloh J. JAMA, J. Am. Med. Assoc. 2005; 294: 2342
    Crossref
  • 10 Scholz V, Nogueira da Silva J. Biomass Bioenergy 2008; 32: 95
    Crossref
  • 11 Warwel VS, Jägers HG, Thomas S. Fat. Sci. Technol. 1992; 94: 323
  • 12 Miao X, Malacea R, Fischmeister C, Bruneau C, Dixneuf PH. Green Chem. 2011; 13: 2911
    Crossref
  • 13 Schrodi Y, Pederson RL, Kaido H, Turpy MJ (Materia, Inc., USA) WO 2007-US81427, 2007 ; Chem. Abstr. 2008, 148, 474047.
  • 14 Jacobs T, Rybak A, Meier MA. R. Appl. Catal., A 2009; 353: 32
  • 15 Elevance Renewable Sciences; Elevance Renewable Sciences and Arkema Announce Partnership to Develop, Produce Renewable Polymers, 2012; http://www.elevance.com/technology/biorefinery/ and http://www.elevance.com/media/news-releases/elevance-renewable-sciences-and-arkema-announce-partnership-to-develop-produce-renewable-polymers/ (accessed Jan 6, 2013)
  • 16 Patel J, Mukinovic S, Jackson WR, Robinson AJ, Serelis AK, Such C. Green Chem. 2006; 8: 450
    Crossref
  • 17 Patel J, Elaridi J, Jackson WR, Robinson AJ, Serelis AK, Such C. Chem. Commun. 2005; 44: 5546
  • 18 Zhu Y, Patel J, Mujcinovic S, Jackson WR, Robinson AJ. Green Chem. 2006; 8: 746
    Crossref
  • 19 Clegg W, Eastham GR, Elsegood MR. J, Tooze RP, Wang XL, Whiston K. Chem. Commun. 1999; 18: 1877
    • 20a Núñez Magro AA, Robb L.-M, Pogorzelec PJ, Slawin AM. Z, Eastham GR, Cole-Hamilton DJ. Chem. Sci. 2010; 1: 723
      Crossref
    • 20b Jiminez-Rodriguez C, Eastman GR, Cole-Hamilton D. Inorg. Chem. Commun. 2005; 8: 878
      Crossref
  • 21 Behr A, Gomes JP. Beilstein J. Org. Chem. 2011; 7: 1
    Crossref
  • 22 von Czapiewski M, Kreye O, Mutlu H, Meier MA. R. Eur. J. Lipid. Sci. Technol. 2013; 115: 76
    Crossref
  • 23 Trost BM, Keinan E. J. Org. Chem. 1979; 44: 3451