Periodate Oxidation of Benzoylated Cotton

Abstract

Purified cotton yarn was partially benzoylated, with and without tension, to three low DS values averaging from 0.2 to 0.6, to retain the fibrous structure of cotton. Benzoylated and untreated yarns were oxidized by sodium metaperiodate at room temperature (32°C) for different periods (4-48 h). The oxidized samples were analyzed for their reducing power in terms of copper number. The percentage accessibility to periodate oxidation was calculated from oxygen consumption values.

In most cases oxygen consumed, copper number of oxidized samples, and accessibility of benzoylated cellulose on periodate oxidation were influenced by the DS but unaffected by tensional forces on the yarn during benzoylation. Benzoylated cotton cellulose is shown to undergo oxidation at slower rate (assessed in terms of rate constant and percentage accessibility) than untreated cotton cellulose, indicating blocking of the secondary hydroxyl groups of cellulose by benzoyl groups. Further, the rate of oxidation was slower at higher DS and was independent of the tensional forces.

Get full access to this article

View all access options for this article.

References

Chatterjee, S.M. , Benzoylation of Cotton in Relation to It's Properties, Textile Res. J. 42, 44-51 (1972).

Consins, E.R. , Bullock, A.L. , Mach, C.H. , and Rowland, S.P. , Periodate Oxidation of Formaldehyde Treated Cottons, Textile Res. J. 34, 953-959 (1964).

Cramer, F.B. and Purves, C.B. , The Unesterified Primary Hydroxyl group in Acetone Soluble cellulose Acetate, J. Am. Chem. Soc. 61, 3458-3462 (1939).

Datye, K.V. and Nabar, G.M. , Studies in the Reaction of Formaldehyde with Unmodified, Modified, and Dyed Cellulose, Textile Res. J. 33, 500-509 (1963).

Davidson, G.F. , The Properties of the Oxycellulose Formed in the Early stages of the Oxidation of Cotton Cellulose by Periodic Acid and Metaperiodate, J. Textile Inst. 31, T81-T96 (1940); The Progressive Oxidation of Cotton Cellulose by Periodic Acid and Metaperiodate Over a Wide Range of Oxygen Consumption, J. Textile Inst. 32, T109-T131 (1941).

Dyer, E. and Arnold, H.E. , Distribution of Hydroxyl groups in Carboxyl methyl cellulose, J. Am. Chem. Soc. 74, 2677-2679 (1952 ).

Genung, L.P. and Mallatt, R.C. , Analysis of Cellulose Derivatives, Anal Chem. 22, 401-405 (1950).

Gloor, W.E. and Klug, E.D. , Cellulose and Cellulose Derivative, Eds. Ott, E. , Spurlin, H. M. and Graffin, M. N. , 2nd ed. Pt. 3, New York, Interscience, 1955, P. 1422.

Goldfinger, G. , Mark, H. , and Siggia, S. , Kinetics of Oxidation of Cellulose with Periodic Acid, Ind. Engng. Chem. 35, 1083-1086 (1943 ).

10.

Head, F.S.H. , Effect of Light on the Reaction Between Periodate and a Glycols, Nature 165, 236-237 (1950); The Effect of Daylight on the Periodate Oxidation of β-Methyl-glucoside, β-Methyl Cellobiside and Cellulose, J. Textile Inst. 44, T209-T223 (1953).

11.

Heyes, T.F. , Cellulose : Copper Number, J. Soc. Chem. Ind. 47, T90-T92 (1928).

12.

Homeyman, J. , Reactions of Cellulose, J. Chem. Soc., Trans., 168-173 (1947).

13.

IS: 1560-1962, Method of Estimation of Carboxylic Acid Groups in Cellulosic Textile Materials, Indian Standards Institution , New Delhi, 1962.

14.

Jackson, E.L. and Hudson, C.S. , The Structure of the Products of Periodic Acid Oxidation of Starch and Cellulose, J. Am. Chem. Soc. 60, 989-991 (1938).

15.

Klenkova, N.I. , Kilakova, O.M. , Tsimara, N.D. , and Khlebosolva , E.N. , Zhur, Priklad, Khim , 35, 2778 (1962).

16.

Mahoney, J.F. and Purves, C.B. , New Methods for investigating the Distribution of Ethoxyl groups in a Technical Ethyl Cellulose, J. Am. Chem. Soc. 64, 9 (1942); The Relationship between the Method of Preparation, the Distribution of Substituents and the Solubility in Water or Alkali of Methyl and Ethyl Ether's of Cellulose, ibid 64, 15 (1942).

17.

Nabar, G.M. and Padmanabhan, C.V. , Estimation of Free Aldehyde Groups in Oxycellulose , J. Soc. Dyers and Colour. 69, 295-297 (1953).

18.

Nabar, G.M. , Shenai, V.A. , and Meghal, S.M. , Some Observations of the Acidic Properties of the Oxycellulose, Curr. Sci. 33, 229-235 (1964).

19.

Nevell, T.P. , The Mechanism of Oxidation of Cellulose by Periodate, J. Textile Inst. 48, T484-T494 (1957).

20.

Nickerson, R.F. , Hydrolysis and Catalytic Oxidation of Cellulose Materials, Ind. Engng. Chem. 34, 1480-1485 (1942).

21.

Rebenfeld, L. and Paesu, E. , Cellulose Studies . Part XIX. Distribution of Methoxyl Groups in Partly Methylated Celluloses, Textile Res. J. 24, 941-955 (1954).

22.

Timell, T.E. , Acta Poly. Tech. 63, 13 (1950).

23.

Vogel, I. , Quantative Inorganic Analysis, London, Longmans, Green & Co., 1951, P342.

24.

Whisler, R.L. and Wolform, M.L. , "Methods in Carbohydrate Chemistry Vol. I, New York, Academic Press, 1962, P. 439.