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Thesis-1967D-J95l.Pdf (2.225Mb) THE LIQUID-PHASE PHOTOCHm,1:ICAL HALOGENATION OF ISOBUTANE AND.ITS MONOHALO DERIVATIVES By . PREM SAGAR, JUNEJAII Bachelor of Scienc~ I>anjab Un:l.versity, Chandigarh. Panjab, India · 1959 Submitted to the Faculty of the Graduate College of the.Oklahom~ State University in partial fulfillment.of the requirements for the degree of .. DOCTOR OF PHXLOSOPHY · Ml:ly, 1967 t>KLAHOMA STATE UNlVERSllY LIBRARY ·JAN 10 1968 THE LIQUID-PHASE PHOTOCHEMICAL HALOGENATION OF ISOBUTANE AND ITS MONOHALO DERIVATIVES Thesis Approved: Thesis Adviser Dean of the Graduate School 558877 ii ACKNOWLEDGMENTS I wish to express my gratitude to Professor E. M. Hodnett, research adviser, for his invaluable guidance, patience·and confidence.tu the author which provided all the inspir1;1tion needed during the course.of my graduate work and the preparation of. this thesi.s. Grateful acknow­ ledgment is made.to Dr. O. C. Dermer, for suggestions and reading the manuscript; to Dr. s. E. Schepple for his criticism and helpful discus­ sions. Thanks are also due to Dr. Rex L. Elmore, a :former colleague, for his help in the early stages of my gradl,late work; to Miss Olamay Chen, without whose help t1'e storage of tritiated isobutane would have been quite inconvenient. Acknowledgment is made to the U. S~ Atomic Energy Commission (Contract No. AT (11-1)-1049), the Chemistry Department, Research Foundation and the Graduate College, all of Oklahoma State University, for financial support. Finally, r wish to thank Bhabha Atomic Resea.rch Center~ Trombay, (formerly A.E.E.T.), Bombay (Government of India) for the study leave granted to t.he author. iii TABLE OF CONTENTS Chapter Page !. INTRODUCTION • • I II. HISTORICAL • • " • • • ii: • • 2 III. INTRODUCTION OT THE EXPREIMENTAL WORK. • . 23. Objectives and Plan of the Study . • • . • . • . 21 Kinetics of Chlorination of. 2-methylpropane-2-E_ • . 26 Assay for Tritium. • • • • • • • 32 IV. EXPERIMENTAL 34 Materials •••• • .• , .••• , 34 Identification of Products • • . • • • • • • • • 34 General Procedure of Halogenation. • • • • . 35 Product Andysis.in tl;le Chlorination of Isobutyl Chloride • • • • • • • • • • • • • • 3 6 Preparative-scale Chlorination of Isobutyl Chloride • • • • • ·. • • • • • • • • • • • • • 36 Quantitative vpc Analysis of Products in Com- petitive Chlorinations • • • • • • . • 37 Preparation of l,2-Dichloro-2-:methylpropane via Addition of Chlorine to Isobutylene • • . • • . 38 Preparation of.l-:Chloro.,-2-:Srom.o-2:.methylpropane 3.9 Peroxide... Catalyzed Addition of·Hydrogen Bromide to Methallyl .Chloride .• , • , • • . • • . • . 39 · Addit.ion .of Bromine t;o · Isobutylene in the Dar;k. · • . 40 Chlorination of tert-Butyl Bromide • . ·• • • , 40 Chlorination of Isobutyl Bromide. • 41 · Brominatton of ~-Butyl Chloride . • • • • • 41 Bromination of Isobutyl Chloride • • 42 Preparation of 2-Methylpr0pane-2-E_ ·• 4.2 Assay of Isobutane-t. • • • . • . • • , • • . 45 Reference Compound for Measuring Activity.of Isobutyl Chloride ! • • • • • • • • • • • 46 Prepara·t;i~ti of. Tritiated Iso-crotyl Chloride 47 Specific Radioactivity of Isocrotyl Chloride. 48 Tritium Assay of the Reaction Products • • • • .51 Photochlorination of 2-Methylpropane-2-E_ • . 53 Specific Radioactivity of Hydrog~n Chloride • . 55 iv Chapter Page IV. RESULTS AND DISCUSSION . .. 58 BIBLIOGRAPHY 91 V LIST OF TABLES Table Page Relative Reactivities of C-H B·onds in Saturated Hydr.ocarb'ons toward · Chlorine Atoms • • • • • • • . 4 II. Vpc. Retention Times and mnr .. Data for the Chloro Brome. Derivatives .of !so.butane ·• • • ·• • . • • • • • • • • 43 IIJ;. Initia\ ~pacific. Radioactivity of Isobu1:an~ and Isoci::otyl Chloride· • • •. • • • • • • • • • • • • • ·• . 50 ry. Vapor Pressu-res ·of Some Compounds at Different Temperatures • , , , • • , • • • . • • • • • • • . 57 '·'- . ' ' ' V. Relative Reactivities of Tet't:iai-y and Pt'imary Hydrogen At011,1s of. 2-Methylpropane · at 24°. • · • • • .. • • ·• • • • ·• 59 : ·.. ··. ,.· VI. Ratio of ReaC:t:f,vities•of Tertiary·and-Primary Hydroge11- Atonis in Some Hydroearbons. • • •· • · • • • . • • • • . • • -60 . VIJ:. Rel,ative React:l.vities of Hydrogen· Atoms. in th.e Chl.orina:- tion of Isobutyl Chloride in c014 at 24° • • • • • • . · ·. 6? VIII... Chlorination· of Isobutyl Chloride i'Q. Carbon Tetrachlo- ride at ...:1s:.to.s0 •· •• ··, -~ •• , ·• , •••• ,' ~. ·•.• • • .. 6.3. IX. Competitive Chlorination .of·Isobutane and,Isobutyl Chloride • • • • · • • . • • • .•. '. • • '•·. • It • • • .•. • • • x. Competitive Chl~rination of Isobutane and ,!!il-Bu.tyl · Chloride . -~ . · . .• . .. _. • . 68 . XI. Solvent.Effects in the Photochlorinat:t.on of.Isobutyl Chloride • • • • : • • • • . • • ... • .. !I • 70 . XII. Solvent Effects in the Competitive Photochlorination of Isobutyl Chloride and.tert...;Butyl Chloride ••• 71 XIII. Final Specific Radioactivity of, Isobutane (E106A 1 , El06B). ~ .•..• ·... • .•...•.. • _...... .81 XIV. Final Specific Radioactivity of Isobutane and Isobutyl Chlorid.e (E106C) • . • • • • • • . • • . • • 82 v-1 Table Page XV. Final Specific Radioactivity of Isobutane,. Runs El07A and El07B. • • • • .• • .• • • • • • • • • • . • ~ 85 XVI. Reactants Used in the Chlorination of 2-Methylpropane- 2-~ • · • •. .• • • • • ·• ·: • •. • .• • . • •. • • . • • • •. .• • • • . 87 XVII... Assays of Isobutane a~q. Isobutyl Chloride for. Seconda~y Isotope Effect ••••••. ~ •••• ~ • • • • • • • • • 89 vii LIST OF.FIGURES Figure Page 1. Appartus for Transferring Isocrotyl Chloride""'.! from an Ampule into an Ionization Chamber • • • • • • • • 49 2. Appartus for Trapping Hydrogen. and· Tritium Chlorides • • 56 viii CHAPTER .I INTRODUCTION The purpose of this investigation is. to gain a better. insight into the different factors which control .the relative rates of substitution of different hydrogen at.oms in a hydrocarbon and its derivatives bearing electronegative groups~ Another objective of thi$ undertaking is to explore the neighboring group effect of bromine.and chlorine suhstituents 'in' the liquid-phase photo.chemical chlorination and bromination of chloro­ and, bromo-derivatives of isobutane. Variation of "relative reactivities 11 with the nature ot the solvent was studied at different concentrations · of an aromatic.and a non-aromatic "complexing·solvent" in order to under­ stand the relative importance.of polar and hyperconjugative intel;:'actions in the photochlorination qf isobutyl an.d tert-butyl cl:\lorides. Primary and secondary tritium isotope ef!ects ·irt the photochemical reaction between chlorine and 2-meth,ylpropane-2-_t were studied.so that Ii better knowledge regarding the nature of the transition state in such reactions could be gained. 1 C,HAPTERII HISTORICAL · Since the. discovery. of·the tr:lphenylmethyl. (trityl) radical by Gromberg in 1900 (41) .and th~ subsequent work, of Taylor (144) and Paneth (98) on the role of radicals. as ·transie.nt intermediates in chemi- cal reactions the. chemistry of free radicals has come a long way. ·· The progress m1;1de in this field may be gauged from the num.berof monographs that· have.appeared i:n·the li:!.st twenty years (105, 138, 140, 148, 153, 162, 16 7) • · Free..:radical halogenation cons·tittites an important phase in the chemistry.of.atoms and radicals; Because of the nature of the subject dealt with in this thes1.s, the hbtorical.background presented here will. be restricted to.the literature which has some bearing on this study. Al.though chlorination of certai,n aliphatic compounds was carried out as far back as the ninet~enth ce~tury (l7, 83, 121), the first pioneering experiments of chlorination were conducted by Hass and coworkers (44, 45). These authors reviewed the older data and as a result of their own precis-a measurements on chlorination of aliphatic hydrocarbons, they formulated a number of rules. ·which may be used to predict qualitatively the reeults of chlorination. The free ... radicalchlorination of hydroc;arbons occurs.in the vapor phase.at high temperatures thermally or at J.ow temperatures photochemi-,­ cally or in the presence of radical sources such as azomethane (151). 2. 3 In the liqufd :phase the reaction-·may be initiated by radicals formed ·• from the decomposition of co:mpounds _such as benzoyl peroxide (151), The facile diesociation of.chlorine by visible light of short wave length, however, makes the photochemical reaction most attractive. Besides the halogen elements, many halogen compounds such as sulfuryl chloride, N-halo amides and N-halo imides, and tert-butyl hypohalites have been employed for halogenation studies. The chain mechanism of photochemica! chlorination was. proposedI . by Pease and Waiz (101) and by Yuster and Reyerson (171) and was later substiantiated by Kharasch and associates .. (9). .An identical mechanism operates-for atomic bromination (59). A very pronounced inhibition by traces of.oxygen was noted in the thermal chloripation of methane (101), A similar behavior was observed by ·Richie and Winning. (106) . Pres~ably in the. presence of oxygen, the normal substitutive step (R: + c12~--_-.,,,, RCl + Cl·) is replaced by R· + o~-->""--R·.,.00', Actually the presence_of large amounts of oxygen 2'' in the system may result in. a halogen-induced auto-oxidation rather than chlorin,ation of the organic substrate (120). - The inhibitory action of oxygen may· also be due to the. forl!latiQn o:I: the transient ~p.ecies Clo which subsequently decomposes to.chlorine and oxygen ·(102, 122,123, 124)~ Peroxide-sensitized chlorination of a number of hydrocarbons and
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