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Synthesis, mass spectrometry, and nuclear magnetic resonance characterization of Di-guerbet esters

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Journal of the American Oil Chemists' Society

Abstract

Several Di-Guerbet esters (DGE) suitable for lubricant applications were synthesized from branched Guerbet alcohols and Guerbet acids. The mass spectra of DGE under electron-ionization and positive chemical-ionization (PCI) conditions were recorded. Gas chromatography-mass spectrometry, especially in PCI mode with methane as reagent gas, is an effective method for analyzing DGE. In methane positive chemical-ionization mass spectrometry, the DGE give molecular ion peaks. In both PCI and EI modes, some other characteristic ions including up to four McLafferty rearrangement products with high m/z are observed. Thus identification of both hydrocarbon moieties is possible. The DGE were also characterized by 1H-and 13C nuclear magnetic resonance.

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References

  1. Guerbet, M., Compt. rend. 128:511 (1899).

    CAS  Google Scholar 

  2. Markownikoff, W., and P. Zuboff, Ueber die Condensation höherer Alkohole: Tricaprylalkohol, Chem. Ber. 34:3246–3249 (1901).

    Article  CAS  Google Scholar 

  3. Krause, H.-J., and A. Syldatk, Neue Tenside aus gemischten Guerbet-Alkoholen, Fette, Seifen, Anstrichm. 87:386–390 (1985).

    Article  CAS  Google Scholar 

  4. Hückel, W., and H. Naab, Sterische Umlagerungen bei Alkoholaten, Chem. Ber. 64:2137–2141 (1931).

    Google Scholar 

  5. Veibel, S., and J.I. Nielsen, On the Mechanism of the Guerbet Reaction, Tetrahedron 23:1723–1733 (1967).

    Article  CAS  Google Scholar 

  6. Strassberger, W., Wachssynthese mittels der Guerbet-Reaktion, Fette, Seifen, Anstrichm. 71:215–218 (1969).

    Article  CAS  Google Scholar 

  7. Klein, E., F. Thömel, and H. Winkler, Darstellung von 5-Alkyl-3-methyl-cyclohexanolen durch Guerbet-Reaktion, Liebigs Ann. Chem.:1004–1017 (1973).

  8. Schaper, U.-A., Die gemischte Guerbet-Reaktion zwischen cyclischen und acyclischen Alkoholen, Fette, Seifen, Anstrichm. 82:454–456 (1980).

    Article  CAS  Google Scholar 

  9. O’Lenick, A.J., Jr., and J.K. Parkinson, Effects of Branching upon Some Surfactant Properties of Sulfated Alcohols, J. Am. Oil Chem. Soc. 73:935–937 (1996).

    Article  CAS  Google Scholar 

  10. Burk, P.L., R.L. Pruett, and K.S. Campo, The Rhodium-Promoted Guerbet Reaction. Part I. Higher Alcohols from Lower Alcohols, J. Mol. Catal. 33:1–14 (1985).

    Article  CAS  Google Scholar 

  11. Burk, P.L., R.L. Pruett, and K.S. Campo, The Rhodium-Promoted Guerbet Reaction. Part II. Secondary Alcohols and Methanol as Substrates, Ibid.:15–21 (1985).

    Article  CAS  Google Scholar 

  12. Fanelli, J.J., Guerbet Alcohol, A Versatile Hydrophobe, J. Am. Oil Chem. Soc. 65:544 (abs.) (1988).

    Google Scholar 

  13. O’Lenick, A.J., and R.E. Bilbo, Saturated Liquid Lubricant Withstands Aluminum Forming, Res. Dev. 162–165 (1989).

  14. Mueller, G., F. Bongardt, M. Fies, and P. Daute, Hydraulic Oils Containing Biodegradable Guerbet Alcohols, U.S. Patent 5,578,558 (1996).

  15. O’Lenick, A.J., Jr., and J.K. Parkinson, A Comparison of the Rates of Esterification of Some Hydroxy Compounds, J. Soc. Cosmet. Chem. 45:247–256 (1994).

    CAS  Google Scholar 

  16. Schmid, K., F. Bongardt, and R. Wüst, Neues Basisöl für die Schmierstoffindustrie, Offenlegungsschrift DE 3929069 (1991).

  17. O’Lenick, A.J., Jr., Guerbet Meadowfoam Esters, U.S. Patent 5,646,321 (1997).

    Google Scholar 

  18. O’Lenick, A.J., Jr., Branched Esters, U.S. Patent 5,581,001 (1996).

    Google Scholar 

  19. O’Lenick, A.J., Jr., Branched Esters in Skin-Care Applications, U.S. Patent 5,656,664 (1997).

  20. O’Lenick, A.J., Jr., Di-Guerbet Esters, U.S. Patent 5,488,121 (1996).

    Google Scholar 

  21. O’Lenick, A.J., Jr., Di-Guerbet Esters in Personal-Care Applications, U.S. Patent 5,639,791 (1997).

  22. Murphy, R.C., Mass Spectrometry of Lipids, Handbook of Lipid Research 7, Plenum Press, New York, Chapter 4 (Fatty Acids), 1993, pp. 71–130.

    Google Scholar 

  23. Ryhage, R., and E. Stenhagen, Mass Spectrometric Studies. I. Methyl Esters of Saturated Normal Carboxylic Acids, Arkiv Kemi 13:523–542 (1959).

    CAS  Google Scholar 

  24. Ryhage, R., and E. Stenhagen, Mass Spectrometric Studies. II. Saturated Normal Long-Chain Esters of Ethanol and Higher Alcohols, Ibid.:483–495 (1959).

    CAS  Google Scholar 

  25. Ryhage, R., and E. Stenhagen, Mass Spectrometric Studies. IV. Esters of Monomethyl-Substituted Long-Chain Carboxylic Acids, Ibid.:291–315 (1960).

    CAS  Google Scholar 

  26. Ryhage, R., and E. Stenhagen, Mass Spectrometric Studies. V. Methyl Esters of Monoalkyl-Substituted Acids with Ethyl or Longer Side Chain and Methyl Esters of Di- and Polyalkyl-Substituted Acids, Ibid.:332–362 (1960).

    CAS  Google Scholar 

  27. Scheutwinkel-Reich, M., and H.-J. Stan, Chemical Ionization Mass Spectrometry of Hydroxy Fatty Acids, Anal. Chem. Symp. Ser. 1979 (publ. 1980), 4 (Recent Dev. Mass Spectrom., Biochem. Med. 6), 45–52.

  28. Plattner, R.D., H.W. Gardner, and R. Kleiman, Chemical Ionization Mass Spectrometry of Fatty Acids: The Effect of Functional Groups on the CI Spectra, J. Am.Oil Chem. Soc. 60:1298–1303 (1983).

    CAS  Google Scholar 

  29. Odham, G., Studies on Feather Waxes of Birds. I. On the Chemical Composition of the Wax in the Free Flowing Secretion from the Preen Gland of Domestic Geese, Arkiv Kemi 21:379–393 (1963).

    CAS  Google Scholar 

  30. Breitmaier, E., and W. Voelter, Carbon-13 NMR Spectroscopy, 3rd Edition, VCH, Weinheim, New York, 1989.

    Google Scholar 

  31. Gunstone, F.D., High Resolution 13C NMR Spectroscopy of Lipids, in Advances in Lipid Methodology-Two, ed. by W.W. Christie, The Oily Press, Dundee, 1993, pp. 1–68.

    Google Scholar 

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Correspondence to Gerhard Knothe.

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Deceased.

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Knothe, G., Carlson, K.D. Synthesis, mass spectrometry, and nuclear magnetic resonance characterization of Di-guerbet esters. J Amer Oil Chem Soc 75, 1861–1866 (1998). https://doi.org/10.1007/s11746-998-0342-y

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  • DOI: https://doi.org/10.1007/s11746-998-0342-y

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