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A STUDY OF THE PRODUCTS GOAL 
 OBTAINED BY THE USE OF 
 BENZENE AND TOLUENE 
 UNDER HIGH PRESSURE 
 
 BY 
 
 FRANKLIN A. McCANN 
 
 THESIS 
 
 FOK THE 
 
 D E G K K E O F B A C H E I . OR OF SCIENCE 
 
 COLLKGK OF LIBERAL ARTS AND SCIENCES 
 
 UNLVEKSITY OF ILLINOIS 
 
€ ■* 
 
Finley 
 
 
 
 
 
 
 UNIVERSITY OF ILLINOIS 
 
 May ^3^ ig^ 
 
 THIS IS TO CERTIFY THAT THE THESIS PREPARED UNDER MY SUPERVISION BY 
 
 Franklin A. McCann 
 
 ENTITLED A_ 7. _9 A _ _? ®_ _ PJt _ 0.Q §>1 _ C).b t_a i ne d _ Ijy 
 
 the Use of Benzene and Toluene Under High Pressure. 
 
 IS APPROVED BY ME AS FULFILLING THIS PART OF THE REQUIREMENTS FOR THE 
 DEGREE OF Bachelor__Qi._SjiiejQc.e 
 
 College of Liberal Atrs and Sciences 
 
 Approve] 
 
 ACTING HEAD OF DEPARTMENT OF -CHEMISTRY. 
 
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TABLE OF CONTENTS 
 
 T. Introduction 
 
 1. Nature of the problem,#, 3 
 
 2 * Historical 4 
 
 3« Theoretical 8 
 
 III. Experimental 
 
 1. Apparatus 9 
 
 2. Determination of the products...* 10 
 
 III. Results...*. 11 
 
 IV Discussion of Results 18 
 
 V. Summary * 21 
 
 VI. Bibliography 22 
 
Digitized by the Internet Archive 
 in 2016 
 
 https://archive.org/details/studyofproductsoOOmcca 
 
APPRECIATION 
 
 This work was done under the direction 
 of Dr. T. E.Iayng, who has given advice, 
 help, and instruction throughout this 
 investigation. I am deeply Indebted to 
 him, not only for the assistance he has 
 given, but for the inspiration he has 
 been throughout the year. 
 
5 
 
 A STUDY OF THE PRODUCTS OF COAL 
 OBTAINED BY THE USE OF BICNZENE 
 AND TOLUENE UNDER HIGH PRESSURE. 
 
 I. Introduction. 
 
 1. Nature of the problem. 
 
 The study of coal by the use of solvents is not a new one. 
 Organic solvents, to be true solvents, as distinct from 
 reagents, should be chemically inert towards both the 
 the substances extracted and the residue. This is why 
 the present work has been carried on with benzene. 
 
 Benzene has been used many times before but always with 
 low yields. The primary object therefore has been to 
 find some means by ^ich benzene can be made to give 
 good yields. High temperatures and pressures were tried, 
 and excellent results were obtained. 
 
 Another object of this work, and the ultimate aim, has 
 been to throw some light upon the reason, and process 
 of coal during carbonization. By studying the fractions 
 of coal obtained, and their behavior in carbonizing, a 
 better insight can be gained into the properties of 
 resins (extracted material) and the cellulose or humic 
 bodies (residue) • 
 
 The best solvents up to this time, notably pyridine and 
 
4 
 
 phenol, undoubtedly perform more than a solvent action. 
 
 In this particular benzene has untold advantages, as it 
 is strictly neutral, and affects neither the extract nor 
 the residue. Benzene has been held in dififavor because of 
 its low solvent action on coal, the use of high temperature 
 and pressure however removes this objection and places 
 benzene among the best of the true solvents. 
 
 2. Historical. 
 
 Schrotter* y^as the first to study coal with the use of 
 solvents, he began his work in 1849. Lei sesse* al so worked 
 with solvents in 18 57, but these studies were isolated 
 and without much value. The first systematic study was 
 made by De Marsilly' in 1862. He treated coal with alcohol, 
 ether, carbon disulfide, benzene, and chloroform at their 
 boiling points. He found that chloroform was the best. This 
 is the first record of benzene being used as a solvent. 
 
 De Marsilly was also the first man to use pressure work 
 for extracting coal. He tried benzene and chloroform 
 under fifteen pounds pressure in a Papin's digester. He 
 found no increase in solvent action. 
 
 Guignet] 1879, made the first extraction that gave a good 
 yield, dry phenol extracting 4^c* This gave a brown solution. 
 Dondorf fl in 1881, obtained a brown resin, using ether, 
 which gave a yield of .3^. Londorff was the first olffserver 
 of the fluoresence of extract solutions. The terra resin 
 
’ 5 
 
 may cause some confusion, by it is meant any amorphous, 
 vitreous mass of organic compounds of inde terminal com- 
 ■ position. 
 
 Siepmann^ 1891, using ether in a Soxhlet apparatus, on a 
 West]phalian coal obtained a deep brown solution with a 
 green fluoresence. The extract was 1.25^. The year 1891 
 also records another failure of benzene, Watson Smith' 
 tried several coals with yields of less than one percent. 
 With pyridine he obtained a yield of 20,^c 
 
 Pictet and Ramseyer' in 1911, i sol ated hexahjrdrofluorene, 
 Gi 3 Hi 6> from a benzene soluble extract. These men are now 
 working with benzene on an elaborate scale, in 1918 ex- 
 tracting 5.5 tons of coal with benzene at its boiling 
 point for four days. They obtained ten and one-half kilos 
 of concentrated heavy brown solution, refraining from 
 completely drying it. 
 
 The work done on carbonization of the portions of coal 
 has been comparatively late; the notable workers in this 
 1 ine are Burgess ana V/heeler, Parr and Hadley, and Porter 
 and Taylor. 
 
 Burgess and Wheelerlargue that coal contains two types 
 of compounds of different degrees of ease of decompostion: 
 The one, the least stable, yielding the parrafin hydro- 
 carbons and no hydrogen; the other decomposing with great- 
 er difficulty and yielding hydrogen alone, or possibly 
 
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6 
 
 hydrogen and the oxides of carbon, as its decomposttion 
 products. 
 
 Porter and Taylor^di sagree with Burgess and Wheeler and 
 find that the cellulosic portion decomposes first, this 
 is the constituent that the latter claim decomposes last, 
 yielding hydrogen. Porter and Taylor found that the cell- 
 ulose broke down into water, the oxides of carbon, and 
 hydrocarbons. 
 
 Jones and Wheeler "^studied the decomposition of the sol- 
 uble and insoluble portions of coal usinf pyridine as a 
 solvent. Ihe cellulosic portion, or residue yielded 
 chiefly phenolic products. ITie resinic portion, the extract, 
 yielded some phenolic products and hydrocarbons. They 
 contented themselves chiefly with the tars obtained. 
 
 Parr and HadleyJused a comparatively high temperature in 
 distilling their fractions, 800 deg.: phenol was used as 
 a solvent. The marked differences in the gases evolved 
 were an increase in hydrogen in the cellulose, or residue, 
 and more paraffins in the extract. 
 
 Later work has been done on carbonization especially in 
 its relation to low temperature carbonization, by Parr 
 and Layng at the University of Tllinoi s.^They find that 
 the order of evolution of gases is as follows* v/ater 250 to 
 300, carbon dioxide 300 to 350 deg., and methane 350 to 
 4pp deg. At this stage begins the evolution of ethane and 
 
7 
 
 the heavier hydrocarbons. They also find that the sulfur 
 that is organically combined begins its early discharge# 
 and the sulfur in the form of pyrites does not decompose 
 until much higher temperatures are reached. The pyritic 
 sulfur shows itself chiefly in the tars. 
 
 Both Parr and Layng, and Potter and Taylor find that most 
 of the organic material of coal is broken down at an 
 early stage in heating, below 500 deg. 
 
 Layng'^advances a theory in regard to the oxidation or 
 weathering of some coals more than others. He states 
 that the peculiar stratifications of resins and cell- 
 ulose in Eastern bituminous coals is the cause for 
 their non** weathering as fast as an Illinois coal where 
 the resins and cellulose are scattered. The resins act 
 as a protective coating for the readily oxidizable cell- 
 ulosic portions, while in the Illinois coal due to this 
 scattered protection the cellulose is quickl«y weathered. 
 
8 
 
 3. TheErretical- 
 
 There are several theories as to the coking of coal, hat 
 the one most generally accepted is that a pasty layer 
 forms around the hot walls and travels slowly inward to 
 the center of the coal mass, coking the coal as it travels* 
 The gases are thought to eacape from the humus bodies 
 first, and are followed by the decomposition of the resins, 
 which leave a pitch behind, binding the coke. If this is 
 true an analysis of the gases from the extract and the 
 residue should show evidences of this priority of de- 
 composi tion* 
 
 Many experimenters have extracted the resins from the 
 coal and afterwards worked with the coal fractions. This 
 vyork seems to bear out the theory that the resins cause 
 the coking, as the residue left after an extraction will 
 not coke, while the extract or a mixture of the extract 
 and the residue will. 
 
 The hydrogen to oxygen ratio in coal is also an index 
 to the coking of coal. An ultimate analysis of the 
 products of coal should then throw some light on the 
 causes for coking as the extract and residue have differ- 
 ent ratios. 
 
 We are then faced with the following problems: 
 
 1) fthat is the best way to obtain a good yield with 
 

9 
 
 a strictly neutaal sol]»ent? 
 
 2) In v/hat way, if any, do the extract and residue differ 
 from the original coal? Does this difference affect the 
 coking properties? 
 
 3) UShat effect has the resin to cellulose ratio have in 
 coking coals? Ihe hydrogen to oxygen ratio? 
 
 4) What form of sulfur, organic or inorganic, causes 
 the evolution of hydrogen sulfide? 
 
 II. Experimental. 
 
 1. Apparatus. 
 
 An iron pressure bomb was used for all extractions. Tni s 
 7/as merely an old mercury flask with a screw plug at the 
 top. This plug was treated with a mixture of litharge and 
 glycerine before each extraction, so as to better seal the 
 plug. 
 
 The heating devise was an electric furnace wound with ni- 
 chromc resistance wire. The temperature control was effected 
 by a sliding resistance wire. 
 
 The fractional carbonization apparatus consisted of a 
 glass flask for the coal, a tube for catching the tar and 
 water, and a tube filled with cadmium sulfate to absorb 
 the hydrogen sulfide evolved, and two sets of aspirator 
 bottles to contain the gases delivered. Tlie heating was 
 accomplished by a small electric furnace, the temperature 
 

 
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 control was obtained by resistance wire. The temperature 
 of the flask was measured by a 500 deg nitrogen filled 
 thermometer. 
 
 2. Determination of products. 
 
 The coal after extraction was filtered and the undissolved 
 coal put back into the flask together with more solvent 
 for a further extraction. The solution was refiltered and 
 distilled until a thick brovn solution resulted. This sol- 
 lution was brom by transmitted light and green by reflected 
 light. It was then transferred to a storage bottle, prev©* 
 lously weighed, and the remaining benzene evaporated at 
 100 deg. Nitrogen was passed in during this last concen- 
 tration and the bottle sealed. Air however had little ef- 
 fect on the extract and it is doubtful if this precai&tion 
 was necessaaby. The residue, or undissolved coal, after the 
 last extraction was Flashed with alcohol and ether and 
 sealed in nitrogen. Air attacks the residue with great 
 avidity and it is necessary to keep the residue in the 
 presence of some inert gas. 
 
 The analysis of the products was as follov/sJ for carbon, 
 the coal was fused with sodium peroxide and treated with 
 acid, the evolved carbon dioxide was measiured and absorbed 
 in caustic potash. The air in the mixture was measured and 
 deducted from the total gas. From the volume of carbon 
 dioxide, the temperature, and the pressure, the total 
 carbon in the coal, extract, and residue was determined. 
 

 
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 Sulfur was determined by fusion with sodikum peroxide 
 and precipi tation with barium chloride. Nitrogen was 
 determined by the well known Kjeldahl method. The hydrogen 
 was found by Eu Long's formula after the B.t.u* was det- 
 ei'mined with an oxygen bomb calorimeter. Oxygen was found 
 by difference. 
 
 The gases from the fractional carbonization were analyzed 
 by a modified Ordat gas apparatus. The carbon dioxide was 
 absorbed by caustic potash, the oxygen by alkaline pyro- 
 galloi, the unsaturated hydrocarbons by bromine water, the 
 aromatics by firming sulfuric acid, the hydrogen and carbon 
 monoxide were oxidized in a copper oxide furnace, the con- 
 traction being the hydrogen, and the carbon dioxide formed 
 absorbed by caustic potash and this volume is the carbon 
 monoxide. The remaining products are then burned in a 
 mercury bulb in the presence of oxygen in excess, and the 
 paraffins computed from the loss in volume and the amount 
 of carbon dioxide formed. 
 
 ITT. Results. 
 
 Benzene was found to extract 13^ from the coal. The sol- 
 ution was a port wine color by transmitted light and green 
 by reflected light. Wien evaporated to dryness the extract 
 was hard and vitreous. 
 
 Various amounts of coal and benzene were tried but the 
 
12 
 
 bext results were obtained by using twenty -five grams of 
 coal and two liters of benzene. Two extractions were 
 sufficient when tliese amounts were used. Hie temperature 
 used was 273 deg #iich gave 50 atmospheres pressures, the 
 critical temperature and pressure of benzene. 
 
 Toiiiuene was used and a twenty-five percent extraction of 
 the coal obtained. The dried extract was not resinous 
 however, and therefore not as satisfactory as benzene which 
 seems to be an ideal solvent. 
 
 The coal used was £rom the Fairmount district of West 
 Virginia, and had the following proximate analysis. 
 
 As received basis. 
 
 Moisture 2.3^ 
 
 Volatile Matter 36.7^c 
 Ash 5.8^ 
 
 Fixed Carbon 55. 2 % 
 
 The ultimate analyses of the original coal, extract, and 
 residue are given in tables 5 and II. 
 
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 Praotional Carboni zation. 
 
 The apparatus was put under a vacuum of three feet of 
 water, exhausted, filled with nitrogen, and exhausted 
 again. Tiiis was done repeatedly until all the air was 
 expelled and the coiil and apparatus saturated with nit- 
 rogen. 
 
 Ten grams were used as a charge. The coal was carbonized 
 ’*as teoeived’*. The flask was slowly heated and a out 
 of the gases made at 350 deg and another at 450 deg. iiere 
 the carbonization was stopped. The tar of the original 
 coal was black and heav^, of the residue black atid light, 
 and the extract of thennature of a light oil, it was 
 reddish in color and accompanied by a red wax which did 
 not mix with the oil evolved. 
 
 The analyses of the two cuts of gases, the amount of 
 tar and hydrogen sulfide evolved, for the driginal coal, 
 extract, and residue will be found in tables III and IV. 
 
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 IV. Discmssi on. 
 
 Benzene extracts 13^ material of a resinous material 
 from coal when used under high temperatures and pressures. 
 The residue consists of the ash, undissolved resins, and 
 the material of cellulosic nature. 
 
 An ultimate analysis of the produats shows that neither 
 the extract nor the residue is chemiaally affected by 
 the action of the benzene. 
 
 This ultimate analysis shows that the ratio of hydrogen 
 to oxygen is approximately 5.5 to 6.5 in the original 
 coal, 5 to 6 in the extract, and 5* 5 to 7 in the residue. 
 
 If we accept the theoty of the hydrogen to oxygen ration 
 as an index to coking coals, the residue should give the 
 poorest coke. This was found to be the case. The reason 
 for the residue coking at all was because of some un- 
 dissolved resins which had not been extracted by the 
 benzene. The residue form the toluene extraction, which 
 gave a better yield, and therefore extracted more resins, 
 gave only a powder -when given coking tests. 
 
 Cherry ‘^found that coal absorbs oxygen readily but states 
 that little is evolved as carbon dioxide. The carbonization 
 of the residue, which is the portion which absorbs oxygen, 
 showred a great evolution of carbon dioxide, though it 
 was exposed to the air but a shoijt time. 
 
19 
 
 Burgess and Wheeler^argue that the resins decompose first 
 and the cellulosic material with greateji difficulty and 
 yielding only hydrogen and the oxides of carbon. The car- 
 bonization of the coal fractions shows that the cellulose 
 begins to decompose earlier th>an 350 deg and with the for- 
 mation of paraffins to the extent of 36^ of the gas evol- 
 ved at 350 deg., and 52^ paraffins at 450 deg. The volume 
 of gas evolved from each of the products shows a greater 
 ease in the decomposition of the resins, and jn this res- 
 pect substantiating Burgess and V.'heeler who find that the 
 resins are the easier decomposed of the two. 
 
 Porter and Taylor^^claim that the cellulosic derivatives 
 decompose the more easily, forming water, the oxides of 
 carbon, and hydrocarbons. The results obtained cannot 
 entirely substantiate this, as the resinic extract de- 
 composed much more readily. The presence of hydrocarbons 
 in the residue decomposition bear out their ^statements 
 as against Burgess and fl,heeler, who claim that the cellu- 
 losic |)ortion gives only hydrogen and the oxides of carbon. 
 
 The great amount of hydrogen sulfide evolved from the 
 resinous extract agrees with Parr and Layng'^who find 
 that the sulfur organically combined is evolved at an 
 early stage. It also shows that the evolution of hydro- 
 gen sulfide is due to the organic sulfur and not the 
 pyrites. 
 
20 
 
 A study of th^ carbonization also points out clearly the 
 effect of weathering on coal. The best coal to weather 
 or store is an Eastern bituminous, the coal worked with, 
 which has the resins and cellulose in stratified form. 
 
 It is thought that the resins in this form of layer pro- 
 tection prevent the cellulosic portion from being oxidized. 
 If the coating d)f tesin is takeri away, as is the case in 
 extraction, the cellulose is no longer protented by the 
 resin and oxidizes rapidly. The residue yielded 29^ more 
 carbon dioxide, notwithstanding the precautions to protect 
 it with nitrogen, than the residwe. This proves that the 
 resin is undoubtedly is a protecting agent. 
 

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21 
 
 V . Sunni ary . 
 
 1) Benzene proves an efficient solvent for coal if used 
 under high temperature and pressure. 
 
 2) The action on the coal is of a tru,e solvent nature 
 
 as neither the extract nor the residue is chemi sally 
 affected. 
 
 3^ The residue, or cellulosic portion, shows a great avidity 
 for oxygen, which it absorbs rapidly, and gives up 
 on heating as carbon dioxide. In this respect it 
 resembles activated carbon. 
 
 4) 'Ihe resinous portion of the coal is the material 
 which decomposes most easily, giving hydrogen, the 
 oxides o§ carbon, and hydrocarbons. 
 
 5) Tlie cellulosic portion decomposes eatly but not as 
 
 easily as the resins, giving hydrogen, the oxides 
 of carbon, and hydrocarbons. 
 
 6) Hydrogen sulfide is evolved by the organic sulfur 
 in coal rather than by the inorgan^ c. 
 
 7) The resinic material proves a protecting agent for 
 the cellulose, if the two are in stratified form. If 
 the resin is removed, the cellulose oxidizes easily. 
 

 
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22 
 
 VI. Bibliography. 
 
 1 « 
 
 2 
 
 3 
 
 4 
 
 5 
 
 7 
 
 Constitution of Goal*«^ Stopes and Wheeler- 1918. 
 
 "Goal and its Scienticio Uses”- Bone. 
 
 "The .dialysis Of Coal witn Phenol as a Solvent" Parr-Hadley 
 The Effect of Oxygen on the Coking of Goal" Cherry 
 "Low Temperature Carbonization ond its Application 
 to High Oxygen Goals" Parr and Layng-J . I. E. Chem 1921. 
 Porter and Taylor, "The Primary Volatile Products of 
 the Carbonization of Coal" Eept. of Int. bull ^^^140 
 T.E.Layng, by oral communication.