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Kinetics and Mechanism of Oxidation of Borneol (Cyclic Secondary Alcohol) by Trichloroisocyanuric Acid in Acidic Medium

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Kinetics and Mechanism of Oxidation of Borneol (Cyclic Secondary Alcohol) by Trichloroisocyanuric Acid in Acidic Medium Jr. of Industrial Pollution Control 25 (1) (2009) pp 1-8 © Enviromedia Printed in India. All rights reserved KINETICS AND MECHANISM OF OXIDATION OF BORNEOL (CYCLIC SECONDARY ALCOHOL) BY TRICHLOROISOCYANURIC ACID IN ACIDIC MEDIUM NAVNEET SHARMA* AND MAMTA GOEL** * Department of Chemistry, H.R. Institute of Technology, Ghaziabad, U.P., India **Department of Chemistry, SGIT, Ghaziabad, U.P., India Key words : Kinetics, Oxidation, Borneol, Trichloroisocyanuric acid, Perchloric acid. ABSTRACT The kinetics of Oxidation of borneol (C10H18O) [endo-1, 7, 7-Trimethyl bicyclo (2, 2, 1) heptan-2-ol] by aqueous perchloric system, yields of ketone in the presence of Trichloroisocyanuric acid at 300C. The stoichiometry is (1:1) and the main oxidation product is Camphor which is studied by TLC using benzene as a solvent and by spraying with 2, 4-dinitrophenyl hydrazine reagent. The observed rate of oxidation shows a first order dependence on both borneol and TCICA (Oxidant). INTRODUCTION have been studied by various oxidants such as N- Bromo-acetamide8, N-Bromoseccharin9, N-Chloro R- Oxidation of organic compounds is one of the most 2, C-6 Diphenyl-t-3 Methyl piperedin-4-on (NCP)10, important reaction in organic synthesis. For this pur- Cerium (IV) Catalysed by chromium (III)11,Cromium pose, some new oxidizing reagents have been pre- (VI) in presence of oxalic acid12, by aqueous chlorine13 pared1-3. In the recent years, studies of oxidation of and oxidation of organic alcohol by pyrazinium various organic compounds in presence of perchlo- dichromate14. The Oxidation of Borneol has been stud- ric acid by halo-compounds4. Borneol is a white crys- ied by chlorine15 and copper (II)-ß-cyclodextrin in py- talline bicyclic terpene alcohol and a component of ridine acetic acid-hydrogen peroxide system16, but many essential oils 5 and it is natural insect repel- there is no references in the literature on the oxida- lent.6 Borneol is easily oxidized to ketone and occurs tion of borneol by TCICA. Hence we have undertaken in two enatiomeric forms in which the hydroxyl group the study of the kinetics of the oxidation Borneol [sub- is placed in an endo-position (Borneol) and an exo- strate] with TCICA [oxidant]. Authors studied the position (Iso-borneol). Borneol is used in traditional kinetics of oxidation of ketones by TCICA in aqueous 17 Chinese medicine as moxa. Oxidation of cyclic sec- acetic acid medium in presence of HClO4 . The reac- ondary alcohol to carbonyl compound is an organic tion was acid-catalyzed exhibiting first order depen- functional group transformation and numerous re- dence each in (acid) and (substrate) and zero order agents and experimental procedures have been de- dependence in (oxidant). Assuming an acid catalyzed veloped for oxidation of alcohols to carbonyl com- enolisation of ketones in the rate determining step pounds7. The oxidation of cyclic secondary alcohols followed by oxidation of enol in a fast step and the Email : [email protected] ; [email protected] Eco-1 2 SHARMA AND GOEL following rate expression was given is used to maintain the ionic strength of the medium). Borneol and doubly distilled water except oxidant - d [ CTICA ] (TCICA) were kept in a corning glass bottle coated on = Ko [TCICA]o [Substrate] [H+] the outside with black japan and wrapped with a dt black cloth was used as reaction Vessel so as to elimi- Authors proposed that the nuclear chlorination nate the possibility of photochemical effect in the ther- by Trichloroisocyanuric acid is the first order reac- mostatic water bath at constant temperature 303K. tion each in [TCICA] and [substrate] & established Fresh solution of TCICA was also kept in the same the following schemes. thermo state. After 30 minutes, the required amount of TCICA was added to the reaction mixture. The TCICA + H O k DCICA + HOCl progress of the reaction is monitored by measuring 2 1 unconsumed TCICA iodometrically at regular inter- → val of time and poured in the conical flask contain- HOCl + H+ k2 H2O+Cl ing ice-cooled 10% KI solution. After keeping for 10 → minutes for liberation of Iodine, the liberated iodine was estimated against a standard solution of sodium H2O+Cl + Cl- k3 H2O + Cl2 ( In Presence of Cl-) → thiosulphate with a micro burette using starch solu- tion as indicator. The volume of sodium thio-sulphate By far the most reliable factor for a kinetics study corresponding to the iodine liberated by unreacted is the effect of concentration. Variation of concentra- TCICA was noted. The rate constants (kobs) in repli- tion of a reactant with fixed concentration of other cates were reproducible with in ± 5%. reactants, leads to the determination of order with respect to that reactant, such a study provides infor- Stoichiometric Investigations mation as to what function the rate is of the concen- Carried out under the conditions [TCICA] = 0.002 tration of that reactant. A review on the functional -3 -3 mol dm , [borneol] =0.001 mol dm , [HClO4] = 0.02 dependence of the various reactant on the rate, leads -3 18 mole dm , solvent aqueous acetic acid (50%v/v) and to the rate expression . temperature 300C were largely not meaningful be- Experimental cause of the appreciable decomposition of TCICA, However, the product was identified as camphor by The cyclic secondary alcohol (substrate) i.e Borneol thin layer chromatography using benzene as solvent (Lancaster) purified by recrystallisation from water 0 and by spraying with 2,4 dinitrophenyl-hydrazine and purity was checked by its melting point (208 C) reagent. before use. Trichloroisocyanuric (oxidant) was of Merck made and KI was of AR grade. Other chemi- RESULTS AND DICUSSION cals (reagents) were of spectroscopic grade. TCICA concentration was estimated iodometrically in acid The reaction is first order in [TCICA] as revealed by medium in accordance with reaction. the constancy of kobs values obtained with different C3O3N3(Cl)3 + 6I- + H+ 3C3O3N3(H)3 + 3I2 + 3Cl- intial [TCICA] and by the linearity of the plot of log (TCICA) > (ICA) [TCICA] vs time. The rate of reaction increases as in- crease in the [borneol] at fixed [TCICA]. A plot of log NaClO4 & HClO used were of annular grade. kobs vs log [borneol] in linear with unit slop indicat- 4 ing first order dependence in [substrate] Fig. 1. The The solution of NaClO4 was prepared by direct weighing while that of HClO4 was prepared by dilu- specific rate increases with an increase in the con- tion and strength was checked by titrating with centration of by hydrogen ions. Ionic strength is in- vestigated by varing [NaClO ] at constant [HClO ]. NaOH using phenolphthalein as indicator. All the 4 4 experiments were conducted under pseudo first or- Increase in ionic strength of the medium has no sig- der conditions using more than ten times the concen- nificant effect on the specific rate. To determine the tration of borneol over the concentration of temperature coefficient and thermodynamic param- Trichloroisocyanuric Acid [TCICA]. The reaction eters, the reaction was carried out at different tem- mixture containing requisite amount of all the reac- perature. A plot of log k Vs 1/T (T is the temperature) is tants i.e. perchloric acid, sodium perchlorate (which obs Eco-1 3 KINETICS AND MECHANISM OF OXIDATION OF BORNEOL linear. Hence the kinetics of the oxidation of borneol by Trichloroisoyanuric acid obey the rate law of first order; in which product camphor (ketone) is formed. ACKNOWLEDGEMENT Authors gratefully acknowledge the Chairman & Di- rector General HRGI and Dr. S.C.Gupta(Director SGIT) for providing the necessary supports. REFERENCES FiSheldon, R.A. and Kkochi, J.K. 1981. Metal-Catalyzed Oxidation of Organic Compounds (Academic Press), New York. Hudlick, M. 1990. Oxidations in Organic Chemistry, (Ameri- can Chemical Society, Washington DC). Plants Containing borneol (Dr. Duk’s Phytochemical and Ethnobotanical Databases) Chemical Information sun. ars-grin.gov. Retrieved on 2008-03-02. Fieser, L.F. and Fieser, M.L. 1967. Reagents for organic synthesis.11 : 44-147. Selvaraj, K., Venkateswaran , V. and Ramarajan, K. 1994. International J. Chemical Kinetics. (26). Fig. 1 Plot of bg kobs Vs. Borneol concentration Nimbalkar, L.V. , Chavan, A.M. and Gokavi, G.S. 1998. J. of Physical Organic Chemistry. II..
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