Skip to main content
SpringerLink
Log in

Esterification of Fatty Acids in Greases to Fatty Acid Methyl Esters with Highly Active Diphenylamine Salts

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Diphenylamine sulfate (DPAS) and diphenylamine hydrochloride (DPACl) salts were found to be highly active catalysts for esterification and substantial transesterification of inexpensive greases to fatty acid methyl esters (FAME). In the presence of catalytic amounts of DPAS or DPACl and excess methanol, the free fatty acids as well as the acylglycerols in waste greases were converted to FAME at 125 °C within 1 h. Although the DPAS and DPACl catalysts were found to have similar catalytic activities to their parent liquid acids (i.e., sulfuric and hydrochloric acids) the diphenylammonium salts are much easier to work with than concentrated liquid acids.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

Article Open access 02 December 2021

Baoxin Zhang, Dilver Peña Fuentes & Armin Börner

References

  1. Banavali R, Hanlon RT, Jerabek K, Schultz AK (2009) Heterogeneous catalyst and process for the production of biodiesel from high free-fatty acid-containing feedstocks. Chem Ind 123:279–289

    Article  CAS  Google Scholar 

  2. Kim M, DiMaggio C, Yan S, Wang H, Salley SO, Simon Ng KY (2011) Performance of heterogeneous ZrO2 supported metal oxide catalysts for brown grease esterification and sulfur removal. Bioresour Technol 102:2380–2386

    Google Scholar 

  3. Corro G, Pal U, Tellez N (2013) Biodiesel production from Jatropha curcas crude oil using ZnO/SiO2 photocatalyst for free fatty acids esterification. Appl Catal B: Environ 129:39–47

    Article  CAS  Google Scholar 

  4. Thiruvengadaravi KV, Nanadagopal J, Sathya Selva Bala V, Dinesh Kirupha S, Vijayalakshmi P, Sivanesan S (2012) The solid acid catalyzed esterification of free fatty acids in pongamia pinnata oil. Energy Sources, Part A:Recov, Util Environ Eff 34:2016–2022

    Article  CAS  Google Scholar 

  5. Guo F, Xiu ZL, Liang ZX (2012) Synthesis of biodiesel from acidified soybean soapstock using a lignin-derived carbonaceous catalyst. Appl Energy 98:47–52

    Article  CAS  Google Scholar 

  6. Zhang J, Liu J, Ma H (2012) Esterification of free fatty acids in Zanthoxylum bungeanum seed oil for biodiesel production by stannic chloride. J Am Oil Chem Soc 89:1647–1653

    Article  CAS  Google Scholar 

  7. Diaz L, Borges ME (2012) Low-quality vegetable oils as feedstock for biodiesel production using k-pumice as solid catalyst. Tolerance of water and free fatty acids contents. J Agric Food Chem 60:7928–7933

    Article  CAS  Google Scholar 

  8. Ngo HL, Zafiropoulos NA, Foglia TA, Samulski ET, Lin W (2008) Efficient two-step synthesis of biodiesel from greases. Energy Fuels 22:626–634

    Article  CAS  Google Scholar 

  9. Zafiropoulos NA, Ngo HL, Foglia TA, Samulski ET, Lin W (2007) Catalytic synthesis of biodiesel from high free fatty acid-containing feedstocks. Chem Commun 35:3670–3672

    Article  Google Scholar 

  10. Ngo HL, Xie Z, Kasprzyk S, Haas M, Lin W (2011) Catalytic synthesis of fatty acid methyl esters from extremely low quality greases. J Am Oil Chem Soc 88:1417–1424

    Article  CAS  Google Scholar 

  11. Majewski MW, Pollack SA, Curtis-Palmer VA (2009) Diphenylammonium salt catalysts for microwave assisted triglyceride transesterification of corn and soybean oil for biodiesel production. Tetrahedron Lett 50:5175–5177

    Article  CAS  Google Scholar 

  12. Foglia TA, Jones KC, Nuñez A, Phillips JG, Mittelbach M (2004) Comparison of chromatographic methods for the determination of bound glycerol in biodiesel. Chromatographia 60:305–311

    Article  CAS  Google Scholar 

  13. Kishimoto Y, Radin NS (1965) A reaction tube for methanolysis; instability of hydrogen chloride in methanol. J Lipid Res 6:435–436

    CAS  Google Scholar 

Download references

Acknowledgments

We thank Mr. Kerby Jones for help on the analytical procedures used in this study. We thank Dr. Phoebe Qi and Mr. Edward Wickham for characterizing the salts using ATR-IR. Finally, we thank Dr. Thomas A. Foglia for helpful advice on this work.

Author information

Authors and Affiliations

  1. US Department of Agriculture, Agricultural Research Service, Eastern Regional Research Center, 600 E. Mermaid Lane, Wyndmoor, PA, 19038, USA

    Helen L. Ngo, Heather Vanselous, Gary D. Strahan & Michael Haas

Authors
  1. Helen L. Ngo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Heather Vanselous
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gary D. Strahan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Michael Haas
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Helen L. Ngo.

Additional information

Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the US Department of Agriculture.

About this article

Cite this article

Ngo, H.L., Vanselous, H., Strahan, G.D. et al. Esterification of Fatty Acids in Greases to Fatty Acid Methyl Esters with Highly Active Diphenylamine Salts. J Am Oil Chem Soc 90, 563–570 (2013). https://doi.org/10.1007/s11746-012-2200-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-012-2200-1

Keywords

Search

Navigation