Startseite An Efficient and Mild Procedure for the Preparation of Aldonic Acids via Oxidation of D-Sucrose by Employing N-Bromophthalimide Oxidant and Micellar System
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An Efficient and Mild Procedure for the Preparation of Aldonic Acids via Oxidation of D-Sucrose by Employing N-Bromophthalimide Oxidant and Micellar System

  • Y. Katre , M. Singh und A. K. Singh
Veröffentlicht/Copyright: 5. April 2013
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Abstract

The oxidation reactions of D-sucrose have been carried out with N-bromophthalimide in the presence of micellar aggregates at 45°C. The kinetics revealed first order dependence on N-bromophthalimide (NBP) and fractional order dependence on D-sucrose. Variation of mercuric acetate concentration has an insignificant effect on reaction rate. The stoichiometric ratio of NBP:D-sucrose was 1:2 and the oxidation product was aldonic acid confirmed by FeCl3–HCl test. The influence of salts on the reaction rate has also been studied. Phthalimide (NHP) and sulfuric acid (H2SO4) inhibit the rate. Thermodynamic and activation parameters have been evaluated and a mechanism consistent with the kinetic data has been proposed. Cetyltrimethylammonium bromide (CTAB) and TritonX-100 (TX-100) catalyze the reaction, while sodium dodecyl sulfate (SDS) inhibits the rate of reaction. The applicability of Berezin's model was tested to explain the observed micellar effects. The rate constants (kM) and binding constants (KS + KO) have been evaluated.

Kurzfassung

Die Oxidationsreaktion von Saccharose wurde mit N-Bromphthalimid in Anwesenheit von micellaren Aggregaten bei 45°C durchgeführt. Die Kinetik zeigte ein Verhalten 1. Ordnung von N-Bromphthalimid (NBP) und eine gebrochene Ordnung von Saccharose. Die Veränderung der Quecksilberacetatkonzentration hat einen unwesentlichen Einfluss auf die Reaktionsrate. Das stöchometrische Verhältnis von NBP:Saccharose war 1:2. Das Oxidationsprodukt Aldonsäure wurde durch den FeCl3–HCl-Test bestätigt. Der Einfluss von Salzen auf die Reaktionsgeschwindigkeit wurde ebenfalls untersucht. Phthalimid (NHP) und Schwefelsäure hemmen die Reaktionsgeschwindigkeit. Die Thermodynamik- und die Aktivierungsparameter wurden ermittelt und ein Mechanismus für eine konsistente Deutung der Daten vorgeschlagen. Cetyltrimethylammoniumbromid (CTAB) und TritonX-100 (TX-100) beschleunigen die Reaktion, während Natriumdodecylsulfat (SDS) die Reaktionsgeschwindigkeit verringert. Die Anwendbarkeit des Berezin Modells für die Erklärung der mizellaren Effekte wurde geprüft. Die Geschwindigkeitskonstante kM und die Bindungskonstanten (KS + KO) wurden ermittelt.

Key words:: Micellar catalysis; critical micellar concentration; kinetics; D-sucrose; Berezin's model
Stichwörter:: Mizellare Katalyse; kritische Mizellkonzentration; Kinetik; D-Sucrose; Berezin-Model
∗ Dr. Yokraj Katre, Department of Chemistry, Kalyan Post Graduate College, Bhilai Nagar, Durg, (C.G.) – 490006, India, Tel.: 0788-2391124, 91-98261-89766, Fax: 0788-2226338. E-Mail:

Dr. Yokraj Katre received his M. Sc. in 1977 from Sagar University, India, and his M. Phil. in 1985 and Ph.D. in 1988 from Vikram University, Ujjain, India, under the guidance of Dr. S. K. Solanki. He participated in 8th International conference of Surfactants and presented a paper at the University of Florida, Gainesville, in 1990. He has been an assistant professor of chemistry in Kalyan P. G. College, Bhilai, since 1978. He continues his research related to micellar kinetics. He has completed three research projects (two UGC and one CCOST). He has attended 233rd ACS conference in Chicago in 2007, attended 12th Asian Chemical Congress in Kuala Lumpur, Maleysia in 2007. He has published more than 36 research papers in different international journals. Under his guidance four students have been awarded their Ph. D. degree. At present he is Prof. & Head, Department of Chemistry, Kalyan Post Graduate College, Bhilai, C. G., INDIA.

Miss Minu Singh received her M. Sc. in organic chemistry in 2006 from Bhilai Mahila Mahavidyalaya, Bhilai, India. She has completed her Ph. D. from Kalyan Post Graduate College, Bhilai, India, in the area of micellar oxidation kinetics, under the supervision of Dr. Y. R. Katre. She has published six research papers in different international journals. At present she is assistant professor in Kalyan Post Graduate College, Bhilai, C. G., INDIA.

Dr. Ajaya Kumar Singh received his M. Sc. In inorganic chemistry from Poorvanchal University, Jaunpur, India, and his D. Phil. in physical chemistry in 2002 from the University of Allahabad, India, under the supervision of Dr. Ashok Kumar Singh. He was selected as an assistant professor of chemistry at Government Science College, Mungeli, Bilaspur, through M. P. Public Service Commission, Indore in 1994. He was awarded a Teacher Research Fellowship to complete his research work in 2000–2002. He is currently associate professor of chemistry at Government V. Y. T. P. G. Autonomous College, Durg, India, where he continues his research work, which is mainly related to transition metal ion-catalyzed oxidation kinetics as well as micellar oxidation kinetics. He is the author of more than 35 papers related to this field. Two students awarded their Ph. D. degree under his guidance.

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Received: 2010-02-10
Published Online: 2013-04-05
Published in Print: 2011-01-01

© 2011, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Editorial
  6. Rückblick auf zwei erfolgreiche Jahre 2009/2010
  7. Application
  8. Surface Activity and Adsorption Properties of New Perfluorinated Carbohydrate Surfactants
  9. Novel Surfactants
  10. Study of Glycerol Residue as a Carbon Source for Production of Rhamnolipids by Pseudomonas aeruginosa (ATCC 10145)
  11. Study of CLSI-M44-A Disk Diffusion Method for Determining the Susceptibility of Candida Species against Novel Complexes Derived from Copper Stearate with 2-Amino Benzothiazoles
  12. European Detergents Conference
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  14. Physical Chemistry
  15. SAXS Study on Azithromycin Loaded Nonionic Microemulsions
  16. Effects of Alkaline Cations on Self-assembly of Cetylpyridinium Surfactants
  17. Influence of Surfactants on Release of Chlorhexidine from Hydrogels
  18. Environmental Chemistry
  19. Influence of Surfactants on the Performance of Calcium Phosphate Scale Inhibitors
  20. Technical Chemistry
  21. Preparation and Characterization of a Phosphorous Free and Non-Nitrogen Antiscalant in Industrial Cooling Systems
  22. Preparation and Characterization of Pillared Derivatives from δ-Layered Sodium Disilicate and their Tribological Properties in Liquid Paraffin
  23. Synthesis
  24. An Efficient and Mild Procedure for the Preparation of Aldonic Acids via Oxidation of D-Sucrose by Employing N-Bromophthalimide Oxidant and Micellar System
  25. Synthesis and Properties of Some N-Acylethylenediamine Triacetic Acid Chelating Surfactants
  26. Conference and Meeting Report
  27. Sixth European Detergents Conference Report
  28. GDCh-Intensive Course Surfactants: Detergents, Cosmetics, Technical Applications
https://doi.org/10.3139/113.110107
Schlagwörter für diesen Artikel
Micellar catalysis; critical micellar concentration; kinetics; D-sucrose; Berezin's model

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Editorial
  6. Rückblick auf zwei erfolgreiche Jahre 2009/2010
  7. Application
  8. Surface Activity and Adsorption Properties of New Perfluorinated Carbohydrate Surfactants
  9. Novel Surfactants
  10. Study of Glycerol Residue as a Carbon Source for Production of Rhamnolipids by Pseudomonas aeruginosa (ATCC 10145)
  11. Study of CLSI-M44-A Disk Diffusion Method for Determining the Susceptibility of Candida Species against Novel Complexes Derived from Copper Stearate with 2-Amino Benzothiazoles
  12. European Detergents Conference
  13. Bicontinuous Microemulsion as Reaction Medium for ω-Transaminase Catalysed Biotransformations
  14. Physical Chemistry
  15. SAXS Study on Azithromycin Loaded Nonionic Microemulsions
  16. Effects of Alkaline Cations on Self-assembly of Cetylpyridinium Surfactants
  17. Influence of Surfactants on Release of Chlorhexidine from Hydrogels
  18. Environmental Chemistry
  19. Influence of Surfactants on the Performance of Calcium Phosphate Scale Inhibitors
  20. Technical Chemistry
  21. Preparation and Characterization of a Phosphorous Free and Non-Nitrogen Antiscalant in Industrial Cooling Systems
  22. Preparation and Characterization of Pillared Derivatives from δ-Layered Sodium Disilicate and their Tribological Properties in Liquid Paraffin
  23. Synthesis
  24. An Efficient and Mild Procedure for the Preparation of Aldonic Acids via Oxidation of D-Sucrose by Employing N-Bromophthalimide Oxidant and Micellar System
  25. Synthesis and Properties of Some N-Acylethylenediamine Triacetic Acid Chelating Surfactants
  26. Conference and Meeting Report
  27. Sixth European Detergents Conference Report
  28. GDCh-Intensive Course Surfactants: Detergents, Cosmetics, Technical Applications
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