Comparison of the methods of the phase transfer catalysis and hydroperoxide in the epoxidation of 1,5,9-cyclododecatriene

• Autorzy: Lewandowski G.
• Języki publikacji: EN

Abstrakty

EN

The process of the epoxidation of cis,trans,trans- 1,5,9-cyclododecatriene (CDT) to 1.2-epoxy-5,9-cyclododecadiene (ECDD) with the 30% aqueous hydrogen peroxide under the phase transfer conditions and with /tert-butyl hydroperoxide under the homogeneous conditions was investigated. Onium salts such as AliquatŽ 336, ArquadŽ 2HT, methyltrioctylammonium bromide and the Na2WO4/H3PO4 catalyst system are very active under the phase transfer catalysis (PTC) conditions for the selective epoxidation of cis,trans,trans-1,5,9-cyclododecatiene (PTC method). These catalytic systems were found to be as active and selective as the homogeneous phase system Mo(CO)6/TBHP (hydroperoxide method).

Słowa kluczowe

EN

epoxidation; 1,5,9-cyclododecatriene; phase transfer catalysis; hydrogen peroxide; tert-butyl hydroperoxide

PL

epoksydowanie; 1,5,9-cyklododekatrien; kataliza przeniesienia międzyfazowego; nadtlenek wodoru; wodoronadtlenek tert-butylu

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2007
• Tom: Vol. 9, nr 3
• Strony: 101--104
• Opis fizyczny: Bibliogr. 11 poz., tab.

Twórcy

autor

Lewandowski G.

• Szczecin University of Technology, Institute of Organic Chemical Technology, Pulaskiego 10, 70-322 Szczecin,

Bibliografia

• 1. Brégeault J. -M.: Transition-metal complexes for liquid-phase catalytic oxidation: some aspects of industrial reactions and of emerging technologies, Dalton Transl., 2003, 3289.
• 2. Choudary B. M., Kantam M. L., Santhi P. L.: New and ecofriendly options for the production of specialty and fine chemicals, Catal. Today, 2000, 57, 17.
• 3. Sheldon R. A.: Selective catalytic synthesis of fine chemicals: opportunities and trends, J. Mol. Catal. A: Chem., 1996, 107, 75.
• 4. Grigoropoulou G., Clark J. H., Elingsb J. A.: Recent developments on the epoxidation of alkenes using hydrogen peroxide as an oxidant, Green Chem., 2003, 5, 1.
• 5. Venturello C., Alneri E., Ricci M.: A new effective catalytic system for epoxidation of olefins by hydrogen peroxide under phase-transfer conditions, J. Org. Chem., 1983, 48, 3831.
• 6. Venturello C., D'Aloisio R.: Quaternary ammonium tetrakis(diperoxotungsto)-phosphate(3-) as a new class of catalysts for efficient alkene epoxidation with hydrogen peroxide, J. Org. Chem., 1988, 53, 1553.
• 7. Ishii Y., Yamawaki K., Ura T., Yamada H., Yoshida T., Ogawa M.: Hydrogen peroxide oxidation catalyzed by heteropoly acids combined with cetylpyridinium chloride: Epoxidation of olefins and allylic alcohols ketonization of alcohols and diols and oxidative cleavage of 1 2-diols and olefins, J. Org. Chem., 1988, 53, 3587.
• 8. Arends I. W. C. E., Sheldon R. A.: Recent developments in selective catalytic epoxidations with H2O2, Topics Catal., 2002, 19, 133 - 141.
• 9. Sharpless K. B., Verhoeven T. R.: Metal catalysed, highly selective oxygenation of olefins and acetylenes with tert-butyl hydroperoxide. Practical consideration and mechanisms, Aldrichim. Acta, 1979, 12, 63 - 74.
• 10. Lewandowski G.: Epoxidation of (Z,E,E)-1,5,9-cyclododecatriene with aqueous hydrogen peroxide by the method of phase transfer catalysis (PTC), Annals of the Polish Chemical Society, Year 2005, v. II, 421.
• 11. Wagner Ch. D., Smith R. D., Peters E. D.: Anal. Chem., 1974, 19, 976.