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The Kinetics of the Thermal Decomposition of Benzaldehyde and Benzyl Benzoate. by Dexter H# Reynolds Submitted in Partial Fulfil

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The Kinetics of the Thermal Decomposition of Benzaldehyde and Benzyl Benzoate. by Dexter H# Reynolds Submitted in Partial Fulfil The kinetics of the thermal decomposition of benzaldehyde and benzyl benzoate Item Type text; Thesis-Reproduction (electronic) Authors Reynolds, Dexter Harold, 1902- Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 23/09/2021 21:27:34 Link to Item http://hdl.handle.net/10150/553204 The Kinetics of the Thermal Decomposition of Benzaldehyde and Benzyl Benzoate. by Dexter H# Reynolds Submitted in partial fulfillment of the requirements for the degree of Master of Science in the College of Letters, Arts, and Sciences, of the University of Arizona 1933 Approved: cfc £ Major adviser f ) * * sS in > t •;r> t ^ o: > >• / 7 s t A £ 9 7?/ /933 & o ACKN OT/LEDGEMKITT The writer wishes to express his most sincere gratitude for the generous advice and assistance of Dr. Lathrop Emerson Roberts, under whose direction this investigation was made. 98620 TABLE OF CONTENTS* Introduction - - - - ------------- - - - - Page 1 Review of literature - ~ --- ------------------ ■ « 5 Preliminary work on the oxides of nitrogen - - - « 7 The apparatus and its use - 9-go a . She thermostat — * 9 b. The thermo-regulator o- - - - - r > - — - ” 10 c. The thermo-couple ------------ * 11 d. The apparatus for following the ; pressure changes acoomp&ayiag reaction 12 Analysis of the product® of reaction • - - - - - « 21 Preparation of materials ~ - - - - - - - - - » 22-23 a. Benaaldehyde - ----------- - - - « 22 b * Benzyl benzoate.'*1' -■* — -;-. ” 23 ■, . ■ .. ' ' ’ I',:/-' - ' ' . Experiaontal data - - - — - - - - - - - ,----- « 24-34 ■ • ' . y : - ' ■ ' ' : . .. ' ' a* Benzaldehyde — - — — — — — —' — ;B4:- b • Benzyl benzoate — — — — — — — — — —w . 28;, 6• Benzoic acid — — — — — — — — * , 33- -■ ■ d « Bensophenone — - - — — — — — — —. — ■— — —. —. H 34 Interpretation of results - - - - - - -- - - > - < 3 5 - 5 5 a • Benzaldehyde — — — ** — — — — — — — — — — .. ^ ■ ■ 35 b. Benzyl benzoate ------- - - - - - - - - n 43 o. Miscellaneous - - - - - - - « 54 Summary - - • » 56 Bibliography « 58 The Kinetiei of the Thermal Decomposition of Benzaldehyde and Benzyl Benzoate. Introduction. One of the fundamental problems of theoretical chem­ istry is the determination of the exact mechanism of chem­ ical change. The study of the kinetics of a chemical reaction is of prime importance in the study of the reaction mechanism,'and li the study of the reasons for the occurence of a reaction. Thermodynamics gives information as to the energy changes involved in a chemical action, and may show whether a reaction may reasonably be expected to occur or not, but it cannot tell whether a reaction will really take place, or whether it will take place appreciably in finite time. In ease the reaction really does take place, thermodynamics can only take account of the conditions of the Initial and final states, and leaves entirely out of consideration the question of intermediate reactions and mechanism of the change. These latter may best be found out by an interpretation of the results of kinetic studies. Reaction rates may he studied either in solution or in the gaseous phase. The literature cites many examples of kinetic studies in both liquids and gases. Inter­ pretation of the results in the liquid state are extremely 2 difficult becaxuw of lack of knowledge of exact molecular conditions in liquids. The kinetic theory of gases gives rather exact information concerning the gaseous state which may he used in interpreting the results of kinetic studies of gaseous reactions. Often, reactions in the gaseous phase may he followed conveniently hy measuring changes in pres­ sure which take place as the reaction proceeds. These facts tend to make the study of gaseous reactions and the inter­ pretation of results much easier than is the case with reactions in solution. In the study of a gas reaction it is desirable to determine the influence of a change of initial pressure of the reacting substance, the effect of temperature changes, and of the influence of the surface of the reaction vessel upon the course of the reaction. It is of importance to find out whether the reaction really occurs in the gaseous phase or whether it takes place on the walls of the con­ taining vessel, i.e., whether the reaction is homogeneous or heterogeneous. The order of the reaction is of consider­ able Importance in the interpretation of results. Unlmoleeular reactions, in particular, are of great interest theoretically in connection with activation theories. Only a few homogeneous gas reactions have been found and studied in which the rate of reaction is proportional to the first power of the partial pressure of the reacting substance. Many studies of the thermal decomposition of vapors have given rise to the idea that as a molecule increases in complexity, the greater is the possibility that it will decompose in accordance with the unimolecular law. For example, it is found that the thermal decompos­ ition of acetaldehyde1 is himolecular, while the decom­ position of the next higher member of the series, prop ion- aldehyde? is unimolecular. The studies mentioned above have all been made with the socalled permanent gases, or with vapors of low boiling liquids. Obviously it is desirable to extend this study to tapers of liquids with molecules of greater complexity. These liquids are in general high boiling. This brings up . several problems in apparatus design which are not present , or are of minor Importance, in the case of the lower boiling liquids. The lack of a stopcock lubricant which will permit the vacuum tight operation of the stopcock at high temper­ atures prevents the use of the usual methods of introducing the vapors into the reaction chamber. Ramsperger3 has designed a stopcock for such operation, but one was not available for the work described in this paper. Then, too, in the case of vapors of high boiling liquids, pressures may not be measured with an ordinary manometer. To prevent eendensation of thejvapors in the tubes nonnesting the reaction flask and the manometer, it is necessary that the connecting tube and the surface of the manometer liquid be heated to a temperature above the boiling point of the liquid being studied* If this temper­ ature Is in the neighborhood of 800®C., it would be difficult end certainly tepraetloal, to obtain a manometer liquid with a sufficiently low vapor pressure to enable the accurate measurement of pressure#! V . Always it is desirable to keep the vapors being studied away from contact with metallic surfaces, and from contamination with stopcock lubricant. That these difficulties have been overcome in a satisfactory manner will be shown in the description of the apparatus used. In the choice of a suitable liquid for study it was observed that the decomposition of the vapors of aoetonef acetaldehyde^ diethyl ether® and trichlormethyl chloro- formate, an ester, in the gaseous state are homogeneous reactions. It would be expected that a higher member of one of the homologous series mentioned would behave in a similar manner. Since the more complex substances appear to decompose unlmolecularly, it was thought that benzal- dehyde would probably decompose homogeneously and unl- molecularly. Benzaldehyde, being easily obtainable, was, therefore, shosen as the subject of the studies to be described in this paper. The reaction proved to be of great complexity, and, in the effort to trace the different possible reactions taking place, it was found that benzyl benzoate apparently decomposed according to the unlmolecular law, homogeneously. The last reaction was, therefore, studied in some detail. •5— Review of the literature. The products of the thermal decomposition of benzol- dehyde were studied by Mile. Peytral; by passing the vapors through a narrow platinum tube at 1150*0., and analyzing the products formed. The chief products of the decomposition were found to be benzene, carbon monoxide, hydrogen, and diphenyl, with small amounts of methane, carbon, and a substance which was thought to be anthracene. In accordance with the analysis of the reaction products, the mechanism of the reaction was given as, V. • ; : .; :... ' ■ l V : . ' : (1) C5H5CHO m CgHg + CO (2) 2 C6H5CH0 « (OgHgJg + H2 + 00. These results have been practically duplicated by Hurd and Bennetf using a pyrex tube at 650-670*0. They identified the substance called anthracene by Mile. Peytral as 9 p-diphenyl benzene. In a sealed tube at 350*0., Lachaann found that two molecules of benzaldehyde combine to form a molecule of benzyl benzoate, according to the reaction, (3) 2 C6H5CHO « CgHs-CHg-O-CO-CgHg. Both Hurd and Bonnet, and Laohmann reported that there is no decomposition of benzaldehyde in a sealed tube at 250*0., even after heating for an eighteen hour period. Hurd and Bennet reported that no methane was formed at 690*0. in pyrex tubing. The gases formed had the following composition by volume: 00 - 86.7$, Hg _ 12.90, GO, - 0.320. 10 Marc da Henrotlnne studied the photoehealeal decoiEpdiltlbn of benzaldehyde. He reported the produets of V - the resetion to be the same as in the thermal decomposition 11 Hurd and Bennett studied to some extent the deooepoe it ion of benzyl benzoate. The sample of 42.5 gras, was sealed in a tube and heated at 346*350°C. for two hours, A high pressure was developed in the tube. Ho further mention was made of the gaseous products, butaaaamgtthe liquid produet# formed are: toluene, benzaldehyde, benzole acid, benzole anhydride, and a considerable amount of tar and residues. The work mentioned above will be considered in more detail when the data obtained in the present study is discussed* Preliminary work on the oxides of nitrogen. Previous to the decision to study the thermal decom­ position of a vapor, an interesting situation was observed among the oxides of nitrogen. In many cases nitrous ezlde acts as a more vigorous oxidizing agent in combustions than does elemental oxygen.
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