-" A STUDY OF THE REPEATED OXIDATION OF CELLULOSE BY A SODIUM HYPOCHLORITE SOLUTION Thesis for the Degree of M‘ S‘ MICHIGAN STATE COLLEGE I.,.. AIIan Fickes I 9‘40 y fab“) ,l 'rlf.’ PL“- A .2 V’s} ‘filfiiair «:11 u “13“.. .I a ”(“Esb‘ ftp“.- -‘ri.h1\.|.&.~ Y.’ 7m! In... “if/0.333., 3*. 1‘ 25%“. hwW.§d-u.. IQINBE-i'...g\sfi gill-E! I i.ll’mjvr.. . A STUDY OF THE REPEATED OXIDATION OF CELLULOSE BY A.SODIUM HYPOCELORI-E SOLUTION by / L. Allan Fickes A THESIS Submitted to the Graduate School of Michigan State College of Agriculture and Applied Science in partial fulfilment of the requirements for the degree of MASTER OF SCIENCE Department of Chemistry 1930 3-‘3. “,p L ‘s‘ (f4; {"1 ..._J i I F441 ACKNOWLEDGEMENT To Professor B. E. Hartsuch, Who suggested the subject for investigation and who made many helpful suggestions as the work pro- gressed, the writer wishes to express his appreciation. 18264.8 TABLE OF CORTBNTS Page No. Introduction 1 - A Purpose of the Work U - 5 Laboratory Procedure .A. Preparation of Bleach Liquor 5 B. Determination of Strength of Bleach Liquor 5 C. Conditioning of Samples 6 D. Bleaching Procedure 6 E. Determination of.Alkali Solubility 7 F. Determination of Copper Number 8 Discussion of Data 9 - 10 Summary 11 Data A. Tables B. Graphs Bibliography A STUDY OF THE RRPEATSD OXIDATION OF CELLULOSE BY A SODIUM HYOPCELORITE SOLUTION Introduction When cellulose is subjected to the action of hypochlorite solutions, or other oxidizing agents, it undergoes changes in both chemical and physical preperties. Mild oxidation has no noticeable effect on the appearance and tensile strength of cotton cloth, but if the treatment is more severe, the material is badly tendered and may become discolored. The action may even by carried to a point where the cloth is reduced to a powdery substance. Pure cellulose is rather unreactive chemically, but oxidized cellulose shows remarkable reducing, acidic and other prop- erties. Oxidized cellulose will reduce Fehling Solution and is soluble in sodium hydroxide solution. It is slightly soluble in pure water, while cellulose itself is insoluble in water. Cotton cloth which has been overbleached in hypochlorite solutions often tends to acquire a slight yellow color in moist air; it is less resistant to heat and so will scorch more easily than cloth which has not been overbleached. There has been an enormous amount of work done in the study of the oxidation of cellulose, but there still remains much to be understood about it. The early workers in the field often ignored the investigations of predecessors and contemporaries, thus slowing up progress in that line. They also were very careless about experimental conditions, and, as a consequence, much of their work lost a great deal of its significance. The discovery of “oxycellulose” is generally attributed to Witz in about 1883. Cross and Bevan, after a visit to the laboratory of Wits, became interested in his work and began investigations on the prepantion 2. of oxycellulose (1). They examined the influence of light, air, heat and subsidiary factors affecting the action of solutions of bleaching powder upon cotton. They showed that the presence of air increased the formation of oxycellulose due to the carbon dioxide which is present in air. With dilute bleaching solutions, the oxidizing action was affected very little by increase in temperature up to 75°C., after which a small increase in temperature greatly increased the effect. Light also prod- uced a marked increase in the amount of oxidation. Other points were in- vestigated, such as the effects of agitation, but they were not accorded much significance at that time. The progress-of oxidation in these ex- periments was measured roughly by the increased attraction of modified cellulose for Methylene Blue and other basic dyes. Bull (2) found that the products of cellulose oxidation possessed acidic properties by the fact that they were soluble in various basic substances. Some of the oxycelluloses could be dissolved in weakly basic substances, while others dissolved only in caustic alkalis. This was evidence that there were several acidic products of oxidation, some being more acidic than others. The work done on the oxidation of cellulose since these investtgtions has, for the most part, dealt with the following: The actions of differ- ent types of oxidizing agents, qualitative studies of the products of oxidation, and comparison of the modified celluloses with normal cellulose. The prime purpose of the greater part of these studies has been to invest- igate the relationship of oxidation to bleaching. .A. Forster and S..A. Pearlman (3) used three criteria in the study of bleaching of sulfate pulps and cotton cellulose: 1. Amount of bleached products soluble in 100 parts of boiling 3% caustic soda in 1 hour. (alkali solubility) 2. Absorption of available chlorine. 3. 3. Lignin value. They found that the degradation of cellulose increased more rapidly as the oxidation progressed. In 193M, L. Lompe (h) studied the effect of dilution and ratio of bleach liquor to cotton cloth. He described a number of experiments on the tendering of cotton by alkaline soda chemic in which the principal variations were made in ratio of chemic to cloth, time and temperature. It was found the ttendering diminished with dilution. When the ratio of chemic to cloth was low, tendering was more severe, and tendering was much faster at 50°C. than at room temperature with other conditions re- mai ning the same. One of the most important investigations of the oxidation of cellu- lose was made by Birtwell, Clibbens, and Ridge (5). They noted that in previous work on the properties of oxycellulose, the materials were cel- luloses which had been drastically modified by oxidizing agents. They devised eXperimental conditions for accurate control and made a system— atic investigation of the oxidation of cellulose by examining the prep— erties of the oxidized products at various intervals during the early stages of reaction. Two extreme types of oxycellulose were recognized, one possessing a high affinity for Methylene Blue and the other a high reducing property. The reducing property of a modified cellulose may be determined by the c0pper number, the definition and determination of which is described later in this paper. The type of cellulose formed in hypochlorite sol- utions is dependent upon the acidity or alkalinity of the solution. An alkaline bleach gives rise to a product with high Methylene Blue number and low cOpper number, while an acid bleach produces an oxycel- lulose with a high copper number and a low affinity for Methylene Blue. u. Oxycellulose with a high Methylene Blue number also possesses a higher solubility in alkali. Bancroft has said, “The literature in regard to oxycellulose is a bit confusing, there being apparently not less than three oxycelluloses; and an ambitious person would probably increase the number so as to have one for every oxidizing agent.“ (6) Cloth whidh has been excessively bleached shows a loss in weight, which indicates that some of the oxidized products are soluble in the ” bleaching solution (7), (8). When cellulose has been oxidized, further oxidation causes a greater degradation than that produced in the previous attack on the cellulose. The greater the previous degradation, the more susceptible is the cellulose to further oxidation. Bartelson (8) found that only in neutral oxidation of cotton cloth by permanganate solutions did different measurements of the rate of oxid- ation show a consistent increase. He concluded that this was due to the fact that there were no other chemical agents present to interfere with and complicatathe normal oxidation process. 11115 psemo _f _ _the We rk The purpose of the present work was to study the changes in cotton cellulose when bleached six consecutive times with a sodium hypochlorite bleach liquor at 50°C. for one hour periods, the cotton being thoroughly rinsed and dried after each bleaching Operation. The material bleached was 100 Berkely cambric. Each bleaching operation was carried out under the same carefully controlled conditions of time, temperature, and ratio of bleach liquor to cloth, and new bleach liquor was used each time the cloth was bleached. After each bleach, the cloth was throughly rinsed to remove all traces of the bleach liquor, dried and weighed. Samples 5. were then removed for testing. These samples were tested for their COpper number (9), (10) and for their solubility in boiling 3% sodium hydroxide for one hour (ll). The strength of the bleach liquor was determined be- fore and after each bleaching Operation by iodimetric titration for the purpose of determining the amount of oxygen used by the cellulose. The experimental conditions, established by trial and error, were such that the cloth still retained its textile quality after the final bleach, but was in an extremely tendered condition. Preparation of Bleach Liquor The bleach liquor used in this problem was made by mixing 2,000 gms. of commercial bleaching powder with about ten liters of distilled water. This was allowed to settle, and the supernatant liquid was siphoned Off. More water was added to the solid material, mixed, and allowed to settle and the supernatant liquid again siphoned off and added to the first vol- ume. This material was then filtered and the calcium precipitated out wdth approxiretely 1,200 gms. of soda lime. The supernatant liquid was filtered off and made up to 20 liters. This stock solution contained between 13 and 1M gms. of available chlorine per liter. It was kept in a dark room at all times. When used in the bleaching Operations, it was diluted in the proportion of one part of the bleach liquor to one part of distilled water. The strength of the diluted solution was determined each time it was made up, and if it was not used up in one day, the strength was determined each day that it was used. The liquor was fairly stable, its oxygen content decreasing only very slightly in the course of several weeks. Determination of Strengjh of Bleach Liquorgilg}: To approximately 3 gms. of potassium iodide dissolved in 50 cc. of water were pipetted 10 cc. of the bleach liquor. This was made acid with 6. 10 cc. of glacial acetic acid and titrated with .lN sodium thiosulfate to a faint yellow color. Four cc. Of starch solution (.5 gm./100 cc.) were added, and the titration was continued to the disappearance of the purple color. Conditioninggof Samples All the cellulose and oxycellulose samples used in COpper number and alkali solubility tests were conditioned in a normal atmosphere jar, as were the Gooch crucibles containing asbestos mats. The normal atmosphere jar was made by placing 35.7% sulfuric acid in the bottom compartment of a glass dessicator instead of a drying agent. This gives the dessicator a condition of 65% relative humidity (13). Bleaching Procedure .A 50 gm. piece of cotton cloth was bleached with 1,500 cc. of bleach liquor, this ratio being retained in each subsequent bleaching Operation on the cloth. The required volume of bleach liquor was placed in a two quart Mason Jar and allowed to come to 50°C. in a constant temperature water bath maintained at that temperature. The cloth was then placed in the jar, thoroughly shaken wdth the bleach liquor and placed in the water bath. During the process Of bleaching, the cloth was kept submerged with a glass stirring rod which was put through a small hole in the cover of the jar. Every fifteen minutes, the jar was removed from the water bath, shaken and immediately returned to the bath. .At the end of one hour, it was again shaken and the cloth removed. The liquid absorbed by the cot- ton was squeezed out into the jar. The cloth was then allowed to soak in about 8 liters of distilled water for a half hour, after which it was rinsed consecutively in a weakly acid solution (2 cc. Of conc. HCl in 8 7. liters of water), a weakly basic solution (2 cc. of conc. NHhOH in 8 liters of water), and finally in 8 liters of distilled water again. In the process of these rinsings, the cloth was repeatedly saturated and squeezed out in each rinsing solution. In the final rinsing this was repeated until the cellulose was neutral to litmus paper pressed against the cloth. It was dried at 50°C. until dry to the touch and then allowed to stand overnight in the air at room temperature. While the cloth was soaking in its first rinse, a portion of the bleach liquor was cooled to room temperature and its strength determined. The dried cloth was weighed and a 6 gm. sample removed for subse- quent investigation. The sample was stored in a tightly corked bottle. The remainder was weighed and bleached again by the procedure just des- cribed, starting with fresh bleaching solution. This procedure was fol- lowed through six times with each sample Of cloth. Four series were run. Determination of Alkali Solubility; A 2.5 gm. sample of the bleached cloth, cut into 1 cm. squares, in a 500 cc. flask, was boiled under a reflux condenser with 100 parts (250 cc.) Of 3% NaOH for one hour. The mixture was strongly heated un- til the first bubbles appeared, then the flame was turned down until the boiling was slow and steady. .At the end of an hour, the flask was re- moved and cooled under the water tap. The solution was then filtered through a conditioned Gooch crucible containing an asbestos mat. The residue was washed with water, then with a few drops of reagent HCl, and finally with water until the washings were neutral to litmus paper. The crucible and residue were dried Overnight in an Oven at 60°C., conditioned and weighed. The percent loss in weight Of the sample was calculated. The same procedure was carried out with a sample of the original 100 Berkely cambric, which was .8% soluble. Determination of Copper Number The copper number of a sample ox oxycellulose is a measure of its reducing power. It is defined as the number of grams of cepper reduced by 100 gms. of cellulose. The method used in this problem for the de- termination of conper number was a micro-method develOped by T. F. Heyes(9). The commercially bleached cambric has a copper number of .20 1. 9. Discussion of Data In Graph 1, it can be seen that the amount of oxygen used by the cellulose increases as the amount of previous oxidation increases. How- ever, the increment Of increase in oxygen consumption decreases with each oxidation. If cellulose were oxidized under the conditions of this eXperiment for a continuous period Of six hours, there would be a crit- ical period where the rate of oxygen consumption would show a sudden marked increase (7). The lack of such a critical period in this study is probably due to the fact that each bleaching Operation is started with fresh bleach liquor. This removes all soluble oxidation products from the scene of action and thus prevents their reacting further with the bleach liquor. Also, the rinsing of the cloth after each bleach removes some soluble products. Thus the soluble oxidation products cannot accum— ulate and cause a possible sudden increase in the consumption Of oxygen. Furthermore, in a continuous oxidation, the alkalinity of the bleach liquor shows a gradual decrease until the beginning of the critical per- iod when the bleach becomes acid, and then the acidity increases rapidly until the end of the critical period (7). In the present study, the re- newing of the bleach liquor with each bleaching Operation prevents such a depletion of alkali, providing another possible explanation for the gradual rise of the curve. These facts explain why a study of this kind cannot be compared with procedures in which cloth has been continuously bleached and the progress of the reaction studied in that way. The loss in weight of the cellulose upon repeated oxidation, as seen in graph 2, shows a different trend than does the rate of oxygen consumpt- ion. Each bleaching Operation causes a greater percentage loss in weight than does the preceding Operation, but in the case the increment Of increase grows larger with each oxidation. This might be expected, for 10. each bleach produces partially oxidized material which remains in the cloth. The next time the cloth is bleached, in addition to the normal cellulose becoming oxidized, the partially oxidized material already present would be very susceptible to further degradation and thus cause a relatively large loss in weight, as compared with the previous oxidat— ion. The COpper number and alkali solubility of the cellulose oxidized once showed a large increase over that of the normal cellulose. Samples from each subsequent bleach showed a more gradual increase (graphs 3 and h). These tests are very indicative of the progress Of oxidation in this study, as may be seen by comparison of the graphs. As well as agreeing with each other, the copper number and alkali solubility values show very close agreement with the values obtained for the oxygen consumption. Cloth, which had been previously bleached, imparted a yellow color to the boiling alkali, and there was a gradual increase in the intensity of the color as the amount of oxidation increased. An attempt was made to measure the change in pH of the bleach liq- uor during each bleaching Operation; however, it was so slight as to be considered insignificant. Also, upon titration of the 3% NaOh before and after each alkali boil, it was found that the difference was not great enogh to exclude experimental error. The results from this experiment point out that the speed of oxidat- ion Of cotton is increased by previous oxidation, and that the greater the previous oxidation, the greater is the speed of degradation of the cotton. If a study of this kind were made on a commercial bleaching process, the life Of a piece Of goods could be accurately predicted in regard to its degradation by oxidation. Also, the life Of the textile could be greatly lengthed by decreasing the time of each successive bleaching Operation upon the material. 3. W 50 ll. Under the condi ions of this experiment, there is no critical period in which there is a sudden increase in the rate of oxidation. The rate of oxidation of cellulose increases with increase in the previous modification of the cellulose. In the repeated bleaching of cotton cloth, the amount of degradat- ion becomes greater with each bleach. Copper number and alkali solubility test are good indicators of the extent to which cotton cloth has been bleached. After cotton cloth has once been bleached, the chances for its tendering become greater with subsequent bleaches. So subsequent bleaches should be carried out with more care in order to minimize damage to the cloth. 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II . . no.9- ILr . n II 5 II it: I. III-.11.! In; a . . . — . .. u .1 -.._ n . . . _ . . . . . . _ . .. . .. . . . I . 4. _ . . é. . . . , L I I .‘I I I I I I l I i . I III 0 Ir .TII III I II I O '0‘ I I“ I 0 .II I III.. 1 I i d I. .0. I I II II III II I-JII IICIII ‘ O 0|.quth I. I o — o t — — YI . 0.. I . .1 ,. I I . _ _ M . . . . c I . I .I I I. b , cg ‘ II - _ ‘ _ h . , . I I .n I “In I .. I u u H . La. . w n . u . _. . . .. _ . n . u . . _ .. . m . I. w. I.» I I I III! II HI III-IIIIIIIII-III I- . I I I I I | III III. I I )..~ BI BLI (JGPAPHY (1) Cross and Bevan, J, Soc, ChemL Ind., 3, 391 (1881)) (2) 131111, _.._T_.___Qhe__._. 1.11,»: ., J_, 1090 (1597) (3) Forster and Pear 1man, J;_§gc Che: 135.,L __, 233 (1935) (h) Lompe, J Text Inst., MMGA (193”) (5) Birtwell, Clibbens, and Riige, #:3314119“, 15, 13 (1925) (6) Bancroft, mailman 19, 159 (1915) (7) Alvori, blasters Thesis, Liichigan State College (1927) (8) Bartleson, Mastefis Thesis, Michigan State College, (1939) (9) Heyes, J. Soc. Cheg,_1gg., 9OT (1928) (10) Lomax, Textile Tesgigg, 138 (11) Knecht and Thompson, g;_s_oqL;Dvg (1920) (12) Scott's Official Methoas of 121111315 (13) Wilson, 113.111.2122...-(2119111. 11, 3.28 (11+) Liinaev, 111.29.11.11:- , 11, 118A (1936) (15) Birtwell, Clihbene and Gleake, J,*Text. InstM 19, T339 (1928) (16) Marsh and Wood, én In s”, (1336 tio_n to the thmisfir'L of “Cel1ulo se -.O_—_..- (17) Matthews, BleaQQing and Related Prqqeggeg . I I I 13%;, I I F ' -!}-é¢-g 7-5.: ‘I v . .‘ ‘%v_'fl >. n . - - . . I, . 7- a l .’ ‘ LI .2 “.‘L b ' - ”‘4' . . ‘.‘l h. t‘ 0-{ _1‘- ' . -\. " cl \ ~ '1’, IR}; ’ .)‘ . .7. O -“-l""’"-‘ I“; ‘1' ’ £447. ‘ T r _ I . ' I - ' ‘ 5p. 't I “ II 'J ' VI 0 ~ J4 "‘ ‘ l ._ 1“ .. /.' Mb .|' ‘ .-“~ . ‘ . .._l..'f\ -. . .1." .- IL.» -- .‘J‘rfi'fl ' . A- ' O ' I . 4 , I . I V _. ~ . I ' ‘ ’9‘ _. ,I . ¢. I 1‘ , . - '. 3": ‘2‘ ' " r-v ‘. I'd. : <1 . ‘ .I 3 ¢:.«.( ,-1 , ;u 5-, . \ ‘v '9‘. Hr "- ‘ - ‘ ' I 2% ) \ ‘1 \ l . . ._ . I ‘ , — " ‘ ‘ . ' I . 7- ~-}/- .- v . 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