Oxidation of ethoxylated fatty alcohols to alkylpolyglycol carboxylic acids using noble metals as catalysts

Authors

  • Spiros Zlatanos Chemical Engineering Department, Aristotle University of Thessaloniki
  • Kostas Laskaridis Chemical Engineering Department, Aristotle University of Thessaloniki
  • Angelos Sagredos Chemical Engineering Department, Aristotle University of Thessaloniki

DOI:

https://doi.org/10.3989/gya.010309

Keywords:

Alkylpolyglycol carboxylic acid, Ethoxy carboxylic acid, Fatty alcohol ethoxylate, Noble-metal catalyst Oxidation, Noble-metal catalyst Dehydrogenation

Abstract


The conversion of ethoxylated fatty alcohols to the corresponding carboxylic acids through dehydrogenation/ oxidation using noble-metal catalysts has been studied. Ethoxylated primary aliphatic alcohols, ethoxylated random secondary aliphatic alcohols and ethoxylated alkylphenols have been converted to the corresponding acids in the presence of a base. The noble metal catalysts Palladium and Platinum were used without significant degradation of the ethoxyl chain in yields that exceeded 90%. On the other hand, the catalysts Rhodium and Ruthenium gave yields of about 80% and 60% respectively.

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References

Aalbers JG. 1964. Lauryl (poly-1-oxapropene) oxaethane carboxylic acids, Drukkerij Wed. G.Van Soenst N. V., Amsterdam.

Gangwal VR, van der Schaaf J, Kuster BFM, Schouten JC. 2005. Influence of pH on noble metal catalysed alcohol oxidation: reaction kinetics and modeling. J. Catal. 229, 389-403. doi:10.1016/j.jcat.2004.11.021

Haines AH. 1988. Methods for the Oxidation of Organic Compounds: Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes, and Aminoarenes, Academic Press, London.

Heyns K, Paulsen H. 1957. Neuere Methoden der präparativen organischen Chemie II. 8. Selektive katalytische Oxydationen mit Edelmetall- Katalysatoren. Angew. Chem. 69, 600-608. doi:10.1002/ange.19570691803

Heyns K, Blazejewicz L. 1960. Katalytische oxydation von primären und sekundären hydroxylverbindungen mit sauerstoff am platinkontakt in flüssiger phase: Über katalytische oxydationen—XIV, Tetrahedron 9, 67-75. doi:10.1016/0040-4020(60)80054-3

Heyns K, Paulsen H. 1962. Selective catalytic oxidation of carbohydrates, employing plantinum catalysts. Adv. Carbohydr. Chem. 17, 169-221.

Korovchenko P, Donze C, Gallezot P, Besson M. 2007. Oxidation of primary alcohols with air on carbonsupported platinum catalysts for the synthesis of aldehydes or acids, Catal. Today 121, 13-21. doi:10.1016/j.cattod.2006.11.007

Mallat T, Baiker A. 2004. Oxidation of Alcohols with Molecular Oxygen on Solid Catalysts. Chem. Rev. 104, 3037-3058. doi:10.1021/cr0200116

Mallat T, Baiker A. 1995. Catalyst potential: a key for controlling alcohol oxidation in multiphase reactors. Catal. Today 24, 143-150. doi:10.1016/0920-5861(95)00016-9

Mallat T, Baiker A. 1994. Oxidation of alcohols with molecular oxygen on platinum metal catalysts in aqueous solutions. Catal. Today 19, 247-284. doi:10.1016/0920-5861(94)80187-8

Röper H. 1990. in: F.W. Lichtenthaler (Ed.) Carbohydrates as Organic Raw Materials, VCH, Weinheim, pp. 267-288.

Schiller G. 1990. in: Houben, Weyl, Müller (Eds.), Methoden der Organischen Chemie, 4th edition, Georg Thieme Verlag, Stuttgart, p.339.

Sheldon RA, Arends IWCE, Dijksman A. 2000. New developments in catalytic alcohol oxidations for fine chemicals synthesis. Catal. Today 57, 157-166. doi:10.1016/S0920-5861(99)00317-X

van Bekkum H. 1990. in: F.W. Lichtenthaler (Ed.) Carbohydrates as Organic Raw Materials, VCH, Weinheim, pp. 289-310.

Vinke P, de Wit D, de Goede ATJW, van Bekkum H. 1992. in: Ruiz P., Delmon B. (Eds.) Studies in Surface Science and Catalysis, Vol. 72: New Developments in Selective Oxidation by Heterogeneous Catalysis, Elsevier Amsterdam, pp.1-20.

Zhan BZ, Thompson A. 2004. Recent developments in the aerobic oxidation of alcohols. Tetrahedron 60, 2917-2935. doi:10.1016/j.tet.2004.01.043

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Published

2009-09-30

How to Cite

1.
Zlatanos S, Laskaridis K, Sagredos A. Oxidation of ethoxylated fatty alcohols to alkylpolyglycol carboxylic acids using noble metals as catalysts. Grasas aceites [Internet]. 2009Sep.30 [cited 2024Mar.28];60(4):360-6. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/586

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Research