Abstract
Polyethoxylates from cardanol and from cardol, the main component phenolic lipids in technical cashew nutshell liquid derived from the replenishable source Anacardium occidentale, were obtained by reaction with ethylene oxide under base-catalyzed conditions. Oligomeric mixtures resulted. In the cardanol series, the first six members of the mixture were independently synthesized for characterization purposes by a variety of reactions. The members in the oligomeric mixture were separated by HPLC, and the composition was determined by 1H NMR spectroscopy and by chromatography. These studies were preparatory to surfactant and biodegradation studies involving comparison with commercially available polyethoxylates derived from petrochemical nonylphenol.
Article PDF
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
Abbreviations
- ASTM:
-
American Society for Testing and Materials
- bp:
-
boiling point
- BSS:
-
British Standard Specification
- CNSL:
-
cashew nutshell liquid
- HPLC:
-
high-performance liquid chromatography
- mp:
-
melting point
- NMR:
-
nuclear magnetic resonance
- ODS:
-
octadecylsilane
- THF:
-
tetrahydrofuran
- TLC:
-
thin-layer chromatography
- UV:
-
ultraviolet
References
Schick, M.J. (ed.), Non-ionic Surfactants, Marcel Dekker, New York, 1966.
Lynn, J.L., Jr., and B.H. Bony, Surfactants, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th edn., John Wiley & Sons, New York, Vol. 23, 1992, p. 510.
Bennie, D.T., Review of the Environmental Occurrence of Alkylphenols and Alkylphenol Ethoxylates, Water Qual. Res. J. Canada 34:79 (1999).
Maguire, R.J., Review of the Persistence of Nonylphenol and Nonylphenol Ethoxylates in Aquatic Environments, Water Qual. Res. J. Canada 34:37 (1999).
Tyman, J.H.P., and I.E. Bruce, Biodegradable Surfactants Derived from Phenolic Lipids, in Surfactants in Lipid Chemistry: Recent Synthetic, Physical and Biodegradative Studies, edited by J.H.P. Tyman, Royal Society of Chemistry, Cambridge, 1992, p. 159.
Tyman, J.H.P., and L.J. Morris, The Composition of Cashew Nut-Shell Liquid, J. Chromatogr. 27:287 (1967).
Tyman, J.H.P., Non-isoprenoid Long-Chain Phenols, Chem. Soc. Rev. 8:499 (1979).
Tyman, J.H.P., Studies in Organic Chemistry, Elsevier, Oxford, Vol. 52, 1996, 465 pp.
Subbarao, R., and V.P. Harigopal, Analysis of Ethylene Oxide Adducts of Cardanol and 3-Pentadecylphenol by NMR and Thin-Layer Chromatographic Procedures, Fette Seifen Anstrichm. 77:197 (1975).
Ahmed, A.F., and G.L. Hart, A Process for Ethoxylating a Derivative of Cashew Nut-Shell Liquid, United Kingdom Patent GB 2262525 (1993).
Graham, M.B., and J.H.P. Tyman, Ozonization of Phenols from Anacardium occidentale (cashew), J. Am. Oil Chem. Soc. 79:725 (2002).
Tyman, J.H.P., Chemical Purification Method, United Kingdom Patent GB 206682B (1983).
Patel, M., J.H.P. Tyman, and A. Manzara, Treatment of Cashew Nut-Shell Liquid, United Kingdom Patent Application 8100208 (1981).
Tyman, J.H.P., I.E. Bruce, and P. Payne, The Phase Separation of Phenolic Lipids from Anacardium occidentale, Nat. Prod. Lett. 1:117 (1992).
Sood, S.K., J.H.P. Tyman, A.A. Durrani, and R.A. Johnson, Practical Liquid Chromatographic Separations of the Phenols in Technical Cashew Nut-Shell Liquid, Lipids 21:241 (1986).
Tyman, J.H.P., R.A. Johnson, M. Muir, and R. Rokhgar, The Extraction of Natural Cashew Nut-Shell Liquid from Anacardium occidentale, J. Am. Oil Chem. Soc. 66:553 (1989).
Shimoda, S., and K. Kuwata, Modified Alkenylsalicylic Acids, Jpn. Kokai Tokkyo Koho JP 10 218241 (1998).
Davis G.L., S.K. Sood, V. Tychopoulos, and J.H.P. Tyman, Practical Separations of the Component Phenols in Cashew Nut-Shell Liquid: Distillation Procedures for Obtaining Cardanol, J. Chem. Tech. Biotech. 32:681 (1982).
Melander, J.L., A. Nahum, and C. Horvath, Mobile Phase Effects in Reversed Phase Chromatography: Changes in Conformation and Retention of Oligo (ethylene glycol) Derivatives with Temperature and Eluent Composition, J. Chromatogr. 185:126 (1979).
Van der Maeden, F.P.B., M.E.F. Biemond, and P.C.G.M. Jannsen, Oligomeric Separations by Gradient Elution High-Performance Liquid Chromatography, J. Chromatogr. 149:539 (1978).
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Tyman, J.H.P., Bruce, I.E. Synthesis and characterization of polyethoxylate surfactants derived from phenolic lipids. J Surfact Deterg 6, 291–297 (2003). https://doi.org/10.1007/s11743-003-0272-3
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11743-003-0272-3