Skip to main content

Advertisement

Log in

Novel Full Hydrogenation Reaction of Methyl Esters of Palm Kernel and Sunflower Oils Into Methyl Stearate Catalyzed by Rhodium, Ruthenium and Nickel Complexes of Bidentate Hexasulfonated o-Phenylendiphosphite Ligands

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

High catalytic activities (TOF = 8680 h−1) have been achieved by novel rhodium catalysts modified with the chelating sulfonated phosphite ligand hexasulfonated o-phenylendiphosphite in the hydrogenation reaction of renewable methyl esters of sunflower oil under mild reaction conditions and a low rhodium concentration of 50 ppm in methanol.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Corma A, Iborra S, Velty A (2007) Chem Rev 107:2411

    Article  CAS  PubMed  Google Scholar 

  2. Huber GW, Iborra S, Corma A (2006) Chem Rev 106:4044

    Article  CAS  PubMed  Google Scholar 

  3. Moser BR (2014) Biofuels 5:5

    Article  CAS  Google Scholar 

  4. Issariyakul T, Dalai AK (2014) Renew Sust Energy Rev 31:446

    Article  CAS  Google Scholar 

  5. Turek T, Trimm DL, Cant NW (1994) Catal Rev Sci Eng 36:645

    Article  CAS  Google Scholar 

  6. Rupilius W, Ahmad S (2007) Eur J Lipid Sci Technol 109:433

    Article  CAS  Google Scholar 

  7. Behr A, Döring N, Durowicz-Heil S, Ellenberg B, Kozik C, Lohr C, Schmidke H (1993) Fat Sci Technol 95:2

    CAS  Google Scholar 

  8. Huber GW, O’Connor P, Corma A (2007) Appl Catal A 329:120

    Article  CAS  Google Scholar 

  9. Knothe G (2010) Prog Energy Combust Sci 36:364

    Article  CAS  Google Scholar 

  10. No S-Y (2014) Fuel 115:88

    Article  CAS  Google Scholar 

  11. Pozdeev VA, Safronov SP, Levanova SV, Krasnykh EL (2012) Russ J Appl Chem 85:261

    Article  CAS  Google Scholar 

  12. Schaff T, Greven H (2010) Lipid Technol 22:31

    Article  CAS  Google Scholar 

  13. Papadogianakis G, Bouriazos A, Tsichla A, Vasiliou Ch, US 8 334 396 B2 (18.12.2012), EP 2 014 752 A1 (23.06.2007), WO 2009/000435 A1 (14.06.2008), US 2010/0234625 A1 (16.09.2010) to Cognis IP Management GmbH and National and Kapodistrian University of Athens

  14. Vasiliou C, Bouriazos A, Tsichla A, Papadogianakis G (2014) Appl Catal B 158–159:373

    Article  CAS  Google Scholar 

  15. Normann W, DE (DRP) 141 029 (14.08.1902), GB 190 301 515 (21.01.1903) to Leprince & Siveke Herforder Maschinenfett & Oelfabrik

  16. Leuteritz G (1969) Fette Seifen Anstrichmittel 71:441

    Article  CAS  Google Scholar 

  17. List GR, Jackson MA (2007) Inform 18:403

    Google Scholar 

  18. List GR, Jackson MA (2009) Inform 20:395

    Google Scholar 

  19. Philippaerts A, Jacobs PA, Sels BF (2013) Angew Chem Int Ed 52:5220

    Article  CAS  Google Scholar 

  20. List GR (2012) Inform 23:451

    Google Scholar 

  21. Ribeiro APB, Grimaldi R, Gioielli LA, Gonçalves (2009) LAG Food Res Int 42:401

    Article  CAS  Google Scholar 

  22. Adhikari P, Shin J-A, Lee J-H, Kim H-R, Kim I-H, Hong S-T, Lee K-T (2012) Food Bioprocess Technol 5:2474

    Article  CAS  Google Scholar 

  23. Zhang L, Muramoto H, Ueno S, Sato K (2011) J Oleo Sci 60:287

    Article  CAS  PubMed  Google Scholar 

  24. Li D, Adhikari P, Shin J-A, Lee J-H, Kim Y-J, Zhu X-M, Hu J-N, Jin J, Akoh CC, Lee K-T (2010) LWT Food Sci Technol 43:458

    Article  CAS  Google Scholar 

  25. Ribeiro APB, Basso RC, Grimaldi R, Gioielli LA, dos Santos AO, Gardoso LP, Gonçalves (2009) LAG Food Res Int 42:1153

    Article  CAS  Google Scholar 

  26. Ribeiro APB, Basso RC, Grimaldi R, Gioielli LA, Gonçalves (2009) LAG J Food Lipids 16:362

    Article  CAS  Google Scholar 

  27. Kim I-H, Lee S-M, Lee B-M, Park H-K, Kim J-Y, Kwon K-I, Kim J-W, Lee J-S, Kim Y-H (2008) J Agric Food Chem 56:5942

    Article  CAS  PubMed  Google Scholar 

  28. Criado M, Hernández-Martín E, López-Hernández A, Otero C (2007) J Am Oil Chem Soc 84:717

    Article  CAS  Google Scholar 

  29. Farmani J, Hamedi M, Safari M, Madadlou A (2007) Food Chem 102:827

    Article  CAS  Google Scholar 

  30. Petrauskaite V, de Greyt W, Kellens M, Huyghebaert A (1998) J Am Oil Chem Soc 75:489

    Article  CAS  Google Scholar 

  31. Schmidt S, Hurtová S, Zemanovič J, Sekretár S, Šimon P, Ainsworth P (1996) Food Chem 55:343

    Article  CAS  Google Scholar 

  32. Hurtová S, Schmidt S, Zemanovič J, Sekretár S, Šimon P (1996) Fett/Lipid 98:60

    Article  Google Scholar 

  33. List GR, Mounts TL, Orthoefer F, Neff WE (1995) J Am Oil Chem Soc 72:379

    Article  CAS  Google Scholar 

  34. Mensink RP, Katan MB (1990) New Eng J Med 323:439

    Article  CAS  PubMed  Google Scholar 

  35. Zock P, Katan MB (1992) J Lipid Res 33:399

    CAS  PubMed  Google Scholar 

  36. German JB, in: Destaillats F, Sébédio J-L, Dionisi F, Chardigny J-M (eds), Trans fatty acids in human nutrition, 2nd edn., Oily Press Lipid Library, Woodhead Publishing, Oxford, 2009, vol 23, pp xix–xxiv

    Google Scholar 

  37. Bysted A, Mikkelsen A, Leth T (2009) Eur J Lipid Sci Technol 111:574

    Article  CAS  Google Scholar 

  38. Hillyer ChD (2007) Inform 18:356

    Google Scholar 

  39. Clifton PM, Keogh JB, Noakes M (2004) J Nutr 134:874

    Article  CAS  PubMed  Google Scholar 

  40. L’Abbé MR, Stender S, Skeaff M, Ghafoorunissa M, Tavella (2009) Eur J Clin Nutr 63:S50

    Article  CAS  Google Scholar 

  41. Hunter JE (2005) Nutr Res 25:499

    Article  CAS  Google Scholar 

  42. Eckel RH, Borra S, Lichtenstein AH, Yin-Piazza SY (2007) Circulation 115:2231

    Article  CAS  PubMed  Google Scholar 

  43. Mozaffarian D, Katan MB, Ascherio A, Stampfer MJ, Willett WC (2006) N Engl J Med 354:1601

    Article  CAS  PubMed  Google Scholar 

  44. Schleifer D (2012) Soc Stud Sci 43:54

    Article  Google Scholar 

  45. Stender S, Astrup A, Dyerberg J (2012) BMJ Open 2:e000859

    Article  PubMed  PubMed Central  Google Scholar 

  46. Stender S, Astrup A, Dyerberg J (2014) BMJ Open 4:e005218

    Article  PubMed  PubMed Central  Google Scholar 

  47. Tarrago-Trani MT, Phillips KM, Lemar LE, Holden JM (2006) J Am Diet Assoc 106:867

    Article  CAS  PubMed  Google Scholar 

  48. Remig V, Franklin B, Margolis S, Kostas G, Nece Th, Street JC (2010) J Am Diet Assoc 110:585

    Article  CAS  PubMed  Google Scholar 

  49. Borra S, Kris-Etherton PM, Dausch JG, Yin-Piazza SY (2007) J Am Diet Assoc 107:2048

    Article  PubMed  Google Scholar 

  50. Menaa F, Menaa A, Menaa B, Tréton J (2013) Eur J Nutr 52:1289

    Article  CAS  PubMed  Google Scholar 

  51. Galvín S, Guillén-Sans R, Galbis J, Guzmán-Chozas M (2016) LWT Food Sci Technol 65:1066

    Article  CAS  Google Scholar 

  52. Patel AR, Dewettinck K (2016) Food Funct 7:20

    Article  CAS  PubMed  Google Scholar 

  53. Kuhnt K, Baehr M, Rohrer C, Jahreis G (2011) Eur J Lipid Sci Technol 113:1281

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. Menaa F, Menaa A, Tréton J, Menaa B (2013) J Food Sci 78:R377–R386

    Article  CAS  PubMed  Google Scholar 

  55. Fitch-Haumann B (1994) Inform 5:668

    Google Scholar 

  56. Bahrmann H, Fell B, Papadogianakis G, DE 3 942 787 B1 (23.12.1989), EP 0 435 071 B1 (12.12.1990), US 632 465 (1990), CA 2 032 371 (1990), JP Hei/2/402 868 (1990), AU 68 368/90 (1990), BR 90 06 501 (1991), TW 79/109 500 (1990), KO 90/20 650 (1990) to Hoechst AG

  57. Bahrmann H, Fell B, Papadogianakis G, DE 3 942 954 B1 (23.12.1989), EP 0 435 084 B1 (13.12.1990), US 632 464 (1990), CA 2 032 372 (1990), JP Hei/2/402 869 (1990), AU 68 367/90 (1990), BR 90 06 444 (1991), TW 79/109 499 (1990), KO 90/20 528 (1990) to Hoechst AG

  58. Fell B, Papadogianakis G, Konkol W, Weber J, Bahrmann H (1993) J Prakt Chem/Chem-Ztg 335:752

    Google Scholar 

  59. Papadogianakis G, Thesis PhD, “Beiträge zur Rhodium-katalysierten Hydroformylierung mittel- und höhermolekularer α-olefine im Ein- und Zweiphasen-System”, Rheinisch-Westfälische Technische Hochschule (RWTH) Aachen, 1990

  60. Favre F, Olivier-Bourbigou H, Commereuc D, Saussine L (2001) Chem Commun 2001:1360

    Article  CAS  Google Scholar 

  61. Ratnayake WMN, Hansen SL, Kennedy MP (2006) J Am Oil Chem Soc 83:475

    Article  CAS  Google Scholar 

  62. Bouriazos A, Sotiriou S, Vangelis C, Papadogianakis G (2010) J Organomet Chem 695:327

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support of this research by the Postgraduate Studies Programme on “Catalysis and its Applications in the Industry” of Greek Ministry of Education and by the Special Account for Research Grants of the Research Committee of the National and Kapodistrian University of Athens are gratefully acknowledged. We thank Cognis GmbH (today BASF) for the supply of the starting materials methyl esters of palm kernel oil (Edenor® ME PK 12-18 F) and of methyl esters of sunflower oil (Sunflower Fatty Acid ME®).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Georgios Papadogianakis.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaika, N., Panopoulou, C., Anagnostopoulou, E. et al. Novel Full Hydrogenation Reaction of Methyl Esters of Palm Kernel and Sunflower Oils Into Methyl Stearate Catalyzed by Rhodium, Ruthenium and Nickel Complexes of Bidentate Hexasulfonated o-Phenylendiphosphite Ligands. Catal Lett 149, 580–590 (2019). https://doi.org/10.1007/s10562-018-2642-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-018-2642-7

Keywords

Navigation