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A STUDY OF THE PRODUCTS OBTAINED BY THE 
 SOLVENT ACTION OF DI-PHENYL ETHER 
 ON VARIOUS COALS 
 
 BY 
 
 HERBERT DUANE GARTER 
 
 THESIS 
 
 FOR THE 
 
 DEGREE OF BACHELOR OF SCIENCE 
 
 / 
 
 IN 
 
 CHEMICAL ENGINEERING 
 
 COLLEGE OF LIBERAL ARTS AND SCIENCES 
 UNIVERSITY OF ILLINOIS 
 
 1922 
 
I 92^ 
 
 UNIVERSITY OF ILLINOIS 
 
 — ^fay- 3 -& 192-3-.- 
 
 THIS IS TO CERTIFY THAT THE THESIS PREPARED UNDER MY SUPERVISION BY 
 
 Herb ert- JDuana-Gajitar 
 
 ENTITLED ^ Btudy of the Products Obtained by 
 of Di-Phenyl Ether on Various Coals. 
 
 IS APPROVED BY ME AS FULFILLING THIS PART OF THE REQUIREMENTS FOR THE 
 DEGREE OF Ba&helJDX--0-f-5.cl-enc.e 
 
 In_ - Ch eml aal - JE n.,su. ne e j: j 
 
 Instructor in Charge 
 
 Approved : 
 
 ACTINGr head of department of _5HEMI_aTRY. 
 
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ACKHOWLEDCtMEN T 
 
 This work was undertaken in the Chemical Laboratory 
 of the University of Illinois. The problem was undertaken 
 at the suggestion of Dr. Laynd and its completion was 
 due to a great extent by his kindly co-operation and 
 advise. I wish to take this opportunity of expressing 
 my appreciation. 
 
 
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A Study of the Products Obtsdned by the Solvent 
 Action of Di-Phenyl Ether on Various 
 Coals. 
 
 1. Introduction. 
 
 1. Nature of the Problem. 
 
 This problem is one of a series of closely 
 related problems which are be»ing studied in this labor- 
 atory with a purpose of learning more about the consti- 
 tuents and carbonization of coal. At first the compo- 
 sition of coal was studied by observing the products that 
 were obtained from the destructive distillation of the coal. 
 Later this problem was attacked using solvents, and 
 
 much work has been done along this line during recent 
 years. Various compounds have been tried as solvents, but 
 most of them have distinct disadvantages, in some oases the 
 solvent acts as a reagent rather than as a solvent, in some 
 it forms add ition products with the coal, while with other 
 solvents it is either very difficult or impossible to 
 remove the solvent fromt&ie products obtained. It is for 
 this reason that di-phenyl ether has been used and its 
 effect upon the products observed. 
 
 2. Historical:- 
 
 There is nothing in the literature concerning 
 the effect of di-phenyl ether on coal, but a review of 
 
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 the work that has been done on the solvent and composition of 
 coal problem will serve as a means of showii^ the importance 
 of this line of work, and why it is desirous to obtain a 
 new solvent that will not have the disadvantages ^ich have 
 been given above. 
 
 Coal is a substance which is the result of the 
 
 degradation of cellulosic constituents together with resinous 
 
 materials. The steps in this degradation as, suggested by 
 
 1 
 
 White and Thiessen are in this order, peat, lignite, bitum- 
 inous, and then anthracite. l!?hite says that the earlier 
 changes in the formation of coal are biochemical, while the 
 later ones are dyn.amo chemical. The formation of each variety 
 of coal depends upon the length of time that the original 
 plant matter has been exposed to the physical forces of the 
 earth. During this time of transformation the material is 
 subjected to heat and pressure. 
 
 Ash free coal consists of carbon, hydrogen, sulfup 
 oxygen, and nitrogen, but the coal molecule itself is very 
 complea. H9hite has shown that the hydrogen and oxygen content 
 of a coal may be taken as an index to the coking power of the 
 coal. It this hydrogen-oxygen ratio is fifty-nine or more, the 
 coal will usually give good coke. Coals which have been 
 
 weathered are usually poor cokers and have a low hydrogen-ox^’’ga n 
 2 
 
 ratio. Hobart in his work found that this ratio held true for 
 the coals that he ^ed. 
 
 The changes in going from vegetable matter to peat 
 

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 is accomplished with a loss of water and oxygen* The changes 
 in the coal in going from peat to anthra^cite indicates a 
 tendency to approach a hydrocarbon. The hydrogen, carbon, and 
 oxygen come from the celliilosic part of the vegetable matter. 
 
 The nitrogen comes partly from the animal matter which is 
 included with the vegetable matter and the remainder from the 
 plant substance. The original plant and vegetable matter 
 tooth contain some sulfur. This gives use to the organic sulfur 
 in coal. Other sulfur compounds, chiefly iron and calcium, 
 are formed from the hydrogen sulfide waters that percolate 
 through the coal and precipitates insoluable compounds. _ The 
 iron and calcium compounds usually form most of the ash. 
 
 The constitution of coal until the present time 
 
 has been studied almost entirely from the basis of destruction 
 
 distillation. This method is a poor one, because it does 
 
 not tell the real nature of the coal, but it has been developed 
 
 on account of the great commerci fJ. importance of coke and gas 
 
 manufacturing. The products from such a distillation are 
 
 the decomposition products of more complex molecules and are 
 
 divided into gaseous, liquid and solid condensate, and a residue 
 
 3 
 
 which consists chiefly of carbon and ash. The volatile products 
 consist of ammonia, carbon dioxide, hydrogen sulfide, hydrogen, 
 methane, carbon monoxide, nitrogen, acetylene, ethylene, other 
 hydrocarbons / pyridin, phenol, benzene, toluene, xylene, naptha - 
 Isene, anthracene , .phenanthrene, cresol, and a great variety 
 of aromatic compounds. The presence of a predominance of 
 ring hydrocarbons and their derivatives had led to a belief 
 
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- 4 - 
 
 that the coal consisted of ring like compounds. The work 
 that has been done on the destructive distillation side will 
 not be discussed inasmuch as the work is almost entirely a 
 study of the volatile prodnopts from coal and does not involve 
 the use of solvents. 
 
 Another method of attacking the constitution of 
 
 co^l problems is by the use of solvents. This has been the 
 
 basis of much investigation in the connection with the coking 
 
 properties of coal. Most of this research has been dons 
 
 on account of the commercial importance of coke. A review of 
 
 the work along this line follows: 
 
 4 
 
 Reinsch in 1885 conducted some experiments usirg 
 solvents on coal. He concluded that by means of solvents it is 
 possible to i^solate from coal substances \iiiich are quite amor- 
 phous, do not exhibit signs of organic structure, and which are 
 characterized by their resistance to concentrated mineral acids 
 and atmospheric influences. He is of the opinion that coal is 
 composed of two substances which are distinguished by the 
 
 difference in their behaviour with alkaline solutions. 
 
 5 
 
 in 1898 Anderson and Roberts said that caustic 
 potash afforded a means of differentiating coking from non- 
 coking coals. 
 
 6 
 
 Baker used pyridin having a boiling point 
 o 
 
 110-130 C. as a solvent. The percent extract varied with the 
 
 kind of coal. The highest extract was 30.4 percent. 
 
 7 
 
 Later Anderson and Hend.erson treated coal 
 
- 5 - 
 
 in a Soxhlet with pyridin. They say that the carbon, hydrogen, 
 and nitrogen in the extract are similar to those in the original 
 coal, although the carbon is usually less. With inferior 
 coking cords they found that the treatment with pyridin destroyed 
 the coking power, and in strong coking coals the coking power 
 is impaired but not destroyed. The amount extracte d was 
 from 15 to 21 percent. 
 
 8 
 
 In 1908 Bedson and Blair used pyridin as a solvent 
 and obtained an extract that varied from 22 to 32 percent. Bedson 
 used pyridin which gave as high as 20.4 percent extract on cer- 
 tain bituminous cords. It yielded extracts of from dark red to 
 brown color and in some instances it exhibited a green fluores- 
 cence. The undissolved residue from the extraction was almost 
 devoid of coking properties. 
 
 9 
 
 In 1912 Lewes gave the result of his investiga- 
 tion using pyridin. There acre twC different resinic bodies 
 present in the coed, one is easily oxidizable, soluable in 
 pyridin and saponifiable with alkalies, and which upon weather^ 
 ing is oxidized into humtus body with the evolution of wa.ter 
 and carbon dioxide and is responsible for the heating of coal 
 ain storage: the other class non-oxidi sable , not saponified by 
 alkalies, and forming with pyridin a compound insoluif.ble in 
 excess of reagent, and this class may be hydrocarbons from 
 decomposed resins as the residue in which they are present 
 yield rich liquid hydrocarbons, as tar and pitch, but are not 
 rich in gas. 
 

 
 
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 10 
 
 Dimroth and Kerkovious used nitric acid 
 on coal. The residue from this extract was a.gain extracted 
 with ether and gave a substance which was amorphous and hygro- 
 scopic. It gave a black color with alkali and was easily 
 soluable in alcohol. 
 
 11 
 
 Pictet and Ramseyer used benzene on a "fat” 
 French coal and obtained hexatiydrofluorene together with some 
 polymers. 
 
 12 
 
 Vignon used aniline on different types of 
 coal and obtained extracts which ran as high as 35 percent. 
 He also used beta quinoline on a "fat" coal and obtained an 
 
 extract of 47 percent. 
 
 13 
 
 Fisher and Oluud used benzene under pressure. 
 
 o 
 
 The extract which was 6.7 per cent, would soften at 140 and 
 
 o 0 
 
 run at 180 C. Cannels coals heated to 350 with naphthalene 
 and extract recovered with chloroform in a Soxhlet gave a 
 yield of 35 to 30 percent. They also used liquid sulfur dioxide 
 to extract the coal, but in such cases the residue was very 
 small. 
 
 14 
 
 In 1912 Wahl used pyridin in a Soxblet and 
 obtained as high as 25 percent for the extracted material. The 
 residue had poor coking properties, but if the extract was 
 added to the residue, the mixture will produce a coke similar 
 to that of the raw sample. 
 
 15 
 
 Clark and feeler extracted coal with pyridin 
 and then the pyridin extract was treated with chloroform. It 
 

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- 7 - 
 
 was noted from the ultimate analysis that the increase in the 
 amount of nitrogen v/as 3.75 percent, showing that nitrogen 
 had been added from some source. 
 
 16 
 
 Frazier and Hoffmeji using phenol forund that, some 
 of the substances isolated approach pure compounds, and some 
 appear to be quite pure hydrocarbons containing small amounts 
 of oxygenated compounds. The investigations was to be con- 
 tinued using pyridin as the solvent. 
 
 17 
 
 Parr and Hadley usir*g phenol say that, (l) Extrac- 
 tion of coal leaves a residue that will not coke. The coking 
 constituents of the coal is in the extract, (s) Destructive 
 distillation of the residue and the extract gave practically 
 the same gases. (3) 0xid3.tion of coal residue, or extract, 
 produces a lowering of the percent of \^olatile matter. (4) Ox- 
 idation decreases the amount of material that can be extracted 
 from coa.1 with phenol and the coking properties are decreased 
 
 in proportion to the extent of oxidation. 
 
 18 
 
 Later Cherry working on the effect of oxygen on 
 coal and the subsequent effect of phenol on the weathered 
 coal found that the cellulosi* portion has greater avidity 
 for oxygen than the resinic portion; the effect of oxygen on 
 the cellulosic constituents is sufficient to destroy the coking 
 power of the coal. 
 
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- 8 - 
 
 II. Experimentcil . 
 
 1. Apparatus. 
 
 The extraction was conducted in an erlenmyer 
 flask with a long refiiuxing tube. The end of this tube was 
 connected to a trap containing alkaline P3^ro gallop in order to 
 keep oxygen out and thus reduce any tendency to oxidize. The 
 flask was placed in an electric furnace where the tanperature 
 was controlled by a variable resistance. 
 
 The excess of di-phenyl ether was distilled 
 
 off, and the extract finally dried in an electric furnace 
 
 in an apparatus as shown in Figure 1. 
 
 The apparatus used in all of the carbonization 
 
 tests is sliown in Figure 2. The apparatus was swept with 
 200 oc. of nitrogen before and after the run. 
 
 The extract and residue were both dried in 
 
 an atmosphere of nitrogen. 
 
 The extraction with alcoholic potash was 
 carried out in an erlenmyer with a water condenser on a steam 
 bath. 
 
 2. Determination of products. 
 
 The ultimate analysis was made according, to 
 standard methods, and the gases from the carbonization tests 
 were analyzed in a University of Illinois modified Orsat 
 apparatus. The results from the ultimate analysis are 
 checked in tables 5, 6, 7, 8, 9 and 10. 
 
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 The tar given off was so small that it could 
 not be separated from the water that condensed with it. The 
 water that did not condense with the tar was caught in a 
 calcium chloride tube and weighed. 
 
 In the carbonization tests on coal, the hydrogen 
 sulfide was determined ty finding the increase in weight of 
 ^he cadnium sulfate tube. This method, however, wqs not 
 entirely satisfactory so in the later runs the cadrsium sulfide 
 was filtered off and weighed, and the am.ount of hydrogen sulfxLe 
 was calculated froi$ this. 
 
 3. Types of Coal Used. 
 
 Three di "^^ferent coals were used in effort to 
 observe the effect of di-phenyl ether on coals of different 
 character. A fresh sample of Franklin County Blue Ridge 
 Cool was used as a sample from Illinois. The Inaiana sample 
 was a fourth vein coal about four months old, while the Alberta 
 coal was from the Canadian Pacific Phtilroad mine 4^14 and was 
 about one year old. The coals were first extracted with 
 di-phenyl ether and this residue extracted with alcoholic 
 potash. 
 
 III. Results. 
 
 Results of all the analyses are given in tabular 
 form in the following tables. In tables 5,6, 7, 8 and 9 and 
 10 the value in the fifth column for the composition of the 
 extract is obtained by calculating the amount of each const ituoit 
 of the original coal that should go into the extract. 
 

 
 ■' , o*: .'o • ' ' : o nl 
 
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 h 
 
 I H 
 
Extraction of Illinois Coal with Di-phenyl ether. 
 
 /linount of 
 Coal 
 
 Amount of 
 Solvent 
 
 Time 
 
 Temp, in 
 Furn ice 
 
 i- Extract 
 of moist, 
 and ash 
 free coal 
 
 60 grs. 
 
 300 grs. 
 
 34 hrs. 
 
 0 
 
 330 C 
 
 3.16 
 
 10 ” 
 
 300 " 
 
 30 « 
 
 0 
 
 350 C 
 
 3.39 
 
 10 " 
 
 300 ” 
 
 6 " 
 
 0 
 
 360 C 
 
 3.39 
 
 o 
 
 CD 
 
 300 ” 
 
 48 " 
 
 0 
 
 350 C 
 
 3.85 
 
 O 
 
 CO 
 
 390 " 
 
 00 
 
 0 
 
 330 C 
 
 3.85 
 
 O 
 1 — 1 
 
 300 « 
 
 30 *’ 
 
 0 
 
 380 C 
 
 3.85 
 
 Table I. 
 

 
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Analysis of Coal Samples 
 
 
 Illinois 
 
 Inciiana 
 
 Alberta 
 
 Air 
 
 Dry 
 
 Dry 
 
 IM & A 
 Free 
 
 Air 
 
 Dry 
 
 Dry 
 
 M & A 
 Free 
 
 Air 
 
 Dry 
 
 Dry 
 
 M & A 
 Free 
 
 Air Dry 
 LO 88 
 
 3. 33 
 
 - 
 
 - 
 
 4.76 
 
 - 
 
 - 
 
 -0- 
 
 - 
 
 - 
 
 Mo i st . 
 
 4.03 
 
 - 
 
 - 
 
 1.66 
 
 - 
 
 - 
 
 .68 
 
 - 
 
 - 
 
 Vol .Mat 
 
 34.85 
 
 36.31 
 
 39. 39 
 
 43.52 
 
 44.25 
 
 48. 79 
 
 15.78 
 
 15.89 
 
 16.76 
 
 Ash 
 
 7.50 
 
 7.82 
 
 - 
 
 9.17 
 
 9. 33 
 
 - 
 
 5.22 
 
 5.25 
 
 - 
 
 Sulphur 
 
 1.31 
 
 1.36 
 
 1.48 
 
 3.75 
 
 3.81 
 
 4.30 
 
 .76 
 
 .77 
 
 83.74' 
 
 .81 
 ^ 88. 30 
 
 Total C 
 
 t 
 
 6$. 85 
 
 72.78 
 
 78.95 
 
 70.67 
 
 71.85 
 
 79.23 
 
 83.18 
 
 Hydroge: 
 
 1 4.67 
 
 4.87 
 
 5.27 
 
 5.03 
 
 5.12 
 
 5.66 
 
 4.42 
 
 4.45 
 
 4.69 
 
 Oxygen 
 
 11.09 
 
 11.56 
 
 12.53 
 
 8. 32 
 
 8.47 
 
 9. 34 
 
 4.29 
 
 4. 32 
 
 4.55 
 
 Nitro-r 
 
 sen 
 
 1.55 
 
 1.61 
 
 1. 75 
 
 1.41 
 
 1.43 
 
 1.58 
 
 1.46 
 
 1.47 
 
 1.55 
 
 B.T.U. 
 
 12774 
 
 13309 
 
 14437 
 
 12S01 
 
 13118 
 
 14465 
 
 14641 
 
 14740 
 
 15550 
 
 Extract 
 
 3.5 
 
 3.64 
 
 3.95 
 
 5. 44 
 
 5.52 
 
 6.05 
 
 .5 
 
 .5 
 
 .5 
 
 \ 
 
 Table 2. 
 
 , 5- 
 
Analysis of di-phenyl Ether Residues 
 
 
 Illinois 
 
 Indiana 
 
 Alberta 
 
 Dry 
 
 Ash 
 
 Free 
 
 Dry 
 
 Ash 
 
 Free 
 
 1 
 
 Dry 
 
 Ash 
 
 Free 
 
 Vol. Mat. 
 
 36. 73 
 
 39.98 
 
 49.41 
 
 5 4.15 
 
 21. 72 
 
 22.90 
 
 Ash 
 
 8.15 
 
 - 
 
 8.76 
 
 - 
 
 5.27 
 
 — 
 
 Sulphur 
 
 1.09 
 
 1.18 
 
 3.98 
 
 3.26 
 
 . 75 
 
 .79 
 
 Total C. 
 
 73.37 
 
 78. 78 
 
 73.83 
 
 79.83 
 
 83. 30 
 
 88.31 
 
 Hydrogen 
 
 5.76 
 
 6.38 
 
 5.00 
 
 5.48 
 
 4.71 
 
 4.96 
 
 Oxygen 
 
 11.11 
 
 IS. 10 
 
 9.10 
 
 9.97 
 
 4.07 
 
 4. 29 
 
 Nitrogen 
 
 1.53 
 
 1.65 
 
 1.33 
 
 1.45 
 
 1.44 
 
 1.53 
 
 B. T. U. 
 
 13107 
 
 14369 
 
 i 13064 
 
 14314 
 
 14828 
 
 15643 
 
 KOH Ext. 
 
 6.51 
 
 7.09 
 
 1.64 
 
 1.80 
 
 .12 
 
 .13 
 
 Table 3. 
 
 1 t 
 

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 if. 
 
 

 Analysis 
 
 of Alcoholic Potash Residues 
 
 1 
 
 
 Illi nois 
 
 Indiana 
 
 j 
 
 Alberta | 
 
 i 
 
 
 Dry 
 
 Ash 
 
 Free 
 
 Dry 
 
 Ash 
 
 Free 
 
 Dry 
 
 Ash 
 
 Fr®e 
 
 Vol. Mat 
 
 34.55 
 
 34.96 
 
 34.93 
 
 46.56 
 
 17.16 
 
 17.56 
 
 Ash 
 
 6.53 
 
 - 
 
 24.99 
 
 - 
 
 2. 32 
 
 - 
 
 Sulphur 
 
 1 .35 
 
 1. 44 
 
 2.94 
 
 3.92 
 
 .72 
 
 .74 
 
 Total C. 
 
 74.64 
 
 79.84 
 
 58. 40 
 
 77.84 
 
 87. 70 
 
 89.78 
 
 Hydrogen 
 
 4.66 
 
 4.-98 
 
 4.64 
 
 6.19 
 
 4.21 
 
 4.31 
 
 Oxygen 
 
 12.62 
 
 13.50 
 
 8.02 
 
 10.69 
 
 3.96 
 
 • • • 
 
 4.05 
 
 Nitogen 
 
 1.21 
 
 1.29 
 
 1.07 
 
 1. 34 
 
 1.09 
 
 1.11 
 
 B. T. U. 
 
 12834 
 
 13728 
 
 108 72 
 
 14492 
 
 15087 
 
 15444 
 
 M 
 
 Table 4. 
 
 1 
 
Balance Sheet for Illircis Coal 
 Di-phenyl Ether Residue to Coal 
 
 
 
 Ash 
 
 Free 
 
 Residue 
 
 To M & A 
 Free Coal 
 
 Coal 
 
 Differ- 
 
 ence 
 
 Amount 
 
 of 
 
 Coal to 
 Extract 
 
 Error 
 
 Ydeld 
 
 
 96.05 
 
 
 
 3.95 
 
 
 Total C 
 
 78.78 
 
 75.68 
 
 78.9 5 
 
 3.27 
 
 3.12 
 
 t .15 
 
 Sulphur 
 
 1.18 
 
 1.13 
 
 1. 48 
 
 .34 
 
 .01 
 
 / .33 
 
 Hydroger 
 
 6.28 
 
 6.03 
 
 5.37 
 
 '.76 
 
 .21 
 
 '.96 
 
 Oxygen 
 
 12.10 
 
 11.63 
 
 12.53 
 
 .91 
 
 . SD 
 
 41 
 
 Ritro- 
 
 een 
 
 1.65 
 
 1.58 
 
 1.75 
 
 .17 
 
 .01 
 
 ^.16 
 
 B.T.U. 
 
 1426R 
 
 13705 
 
 14437 
 
 732 
 
 570 
 
 ^ 162 
 
 
 
 Table 5. 
 
 ■ 
 
Balance for Indiana Coal 
 Di-Phenyl Ether Residue to Coal 
 
 
 Ash 
 
 Free 
 
 Residue 
 
 To M & A 
 Free Coal 
 
 Coal 
 
 Di ffer- 
 ence 
 
 Amt . of 
 Coal to 
 Extract 
 
 Error 
 
 Yield 
 
 
 93.95 
 
 
 
 6.05 
 
 
 Total C 
 
 79.83 
 
 74. 89 
 
 79.33 
 
 4.34 
 
 4.79 
 
 -.45 
 
 Sulphur 
 
 3.26 
 
 3.05 
 
 4.30 
 
 1.15 
 
 .35 
 
 + .90 
 
 Hydroger 
 
 5. 48 
 
 5.15 
 
 5.64 
 
 . 49 
 
 .30 
 
 +.19 
 
 Oxyg en 
 
 9.97 
 
 9. 36 
 
 9.3ft 
 
 - .03 
 
 .56 
 
 58 
 
 Nitro- 
 
 gen 
 
 1.45 
 
 1.36 
 
 1.58 
 
 .33 
 
 .01 
 
 + .31 
 
 B. T. U. 
 
 14314 
 
 13448 
 
 14465 
 
 1017 
 
 875 
 
 + 142 
 
 Table 6. 
 
( 
 
 \ 
 
 i 
 
 
 f 
 
 (,l rTp c r 
 
 
 I 
 
 i 
 
 
Balance Sheet for Alberta Coal 
 
 Di-phenyl Ether Residue to Coal 
 
 F 
 
 
 Ash Free 
 Residue 
 
 To M & A 
 Free Coal 
 
 Coal 
 
 Differ- 
 
 ence 
 
 Amount of 
 Coal to 
 Extract 
 
 [ 
 
 Error 
 
 Yield 
 
 
 99. 5 
 
 
 
 . 
 
 .5 
 
 
 Total C 
 
 80? -31 
 
 87.89 
 
 88.30 
 
 . 41 
 
 .44 
 
 -.03 
 
 Sulphur 
 
 .79 
 
 .S9 
 
 .81 
 
 .03 
 
 .04 
 
 -.02 
 
 Hydrogen 
 
 4.96 
 
 4.91 
 
 4.69 
 
 -.32 
 
 .03 
 
 -.24 
 
 Oxygen 
 
 4.39 
 
 4.27 
 
 4.55 
 
 .18 
 
 .02 
 
 + .16 
 
 Nitrogen 
 
 1.53 
 
 1.51 
 
 1.55 
 
 .03 
 
 .01 
 
 -t.02 
 
 B. T. U. 
 
 15643 
 
 15564 
 
 1555 0 
 
 '14 
 
 77 
 
 - 91 
 
 Table 7 
 
 / 
 
Balance Sheet for Alcoholic Pota.sh Residues-Illinois Coal 
 
 * 
 
 Alcoholic Potash Residues to Di-phenyl Ether Residue 
 
 
 Ash Free 
 Residue 
 
 To Ash 
 Free Di- 
 phenyl 
 Residues 
 
 Di-pheny] 
 Residue 
 Ash Free 
 
 nffer-' 
 
 ence 
 
 Amt . 0 f 
 Di-phenyl 
 Res.‘ 
 to Ale*. 
 KOH Ext. 
 
 Error 
 
 Yield 
 
 - 
 
 92.91 
 
 - 
 
 - 
 
 7.09 
 
 - 
 
 Total C 
 
 79.84 
 
 74.17 
 
 78.78 
 
 4. 61 
 
 5.57 
 
 -.96 
 
 Sulphur 
 
 1. 44 
 
 1. 34 
 
 1.18 
 
 '-.16 
 
 .08 
 
 -.34 
 
 Hydroge 
 
 1 4.98 
 
 4.62 
 
 6.28 
 
 1.66 
 
 . 44 
 
 •1-1.22 
 
 Oxygen 
 
 13.50 
 
 12.54 
 
 12.10 
 
 44 
 
 . 86 
 
 '1.30 
 
 Nitrogen 
 
 1.29 
 
 1.20 
 
 1,65 
 
 .45 
 
 .11 
 
 + . 34 
 
 B. T. U. 
 
 13728 
 
 12754 
 
 14269 
 
 1515 
 
 1011 
 
 f 504 
 
 
 
 Table 8. 
 
 : 
 

 
Balance Sheet for Alcdiholic Potash Residue-Indiana Coal 
 Alcoholic Potash Residues to Di-phenyl Ether Residue 
 
 
 Ash Free 
 Residue 
 
 « - « 
 To Ash 
 Free Di- 
 phenyl Res 
 
 — 
 
 Di -phenyl 
 Residue 
 . Ash Free 
 
 Differ-' 
 ence . 
 
 Amt . of 
 Di-pheny! 
 Residue 
 to Alc.KOH 
 Extract 
 
 Error 
 
 Yield 
 
 
 98.2 
 
 . 
 
 
 1.8 
 
 
 Total C 
 
 77.84 
 
 76.43 
 
 79.82 
 
 3.39 
 
 1.43 
 
 4- 1.96 
 
 Sulphur 
 
 3.93 
 
 3.84 
 
 3.26 
 
 ' .58 
 
 .06 
 
 - .64 
 
 Hydroger 
 
 6.19 
 
 6.08 
 
 5.48 
 
 - .60 
 
 .09 
 
 - .69 
 
 Oxygen 
 
 10.69 
 
 10.49 
 
 9.97 
 
 -.52 
 
 .17 
 
 - .68 
 
 Nitrogen 
 
 1. 34 
 
 1.31 
 
 1.45 
 
 .14 
 
 .02 
 
 + .12 
 
 B. T. U 
 
 14492 
 
 13631 
 
 14314 
 
 683 
 
 258 
 
 + 425 
 
 ' Table S, 
 
Balance Sheet for Alcoholic Potash Residue- Alberta Coal 
 Alcoholic Potash Residues to Di-phenyl Ether Residue 
 
 
 Ash Free 
 Residu e 
 
 To Ash 
 Free Di- 
 ph9n3’’l 
 Residues 
 
 Di -phenyl 
 Residue 
 Ash Free 
 
 Diff. 
 
 = 
 
 Amt . of 
 Di -phenyl 
 Residue 
 to Alc.KOH 
 Ext ract 
 
 Error 
 
 
 
 
 
 
 
 
 Yield 
 
 - 
 
 99.87 
 
 - 
 
 - 
 
 .13 
 
 - 
 
 Total C 
 
 89.78 
 
 89.66 
 
 88. 31 
 
 -1.35 
 
 .115 
 
 -1.46 
 
 ■^■^Iphur 
 
 . 74 
 
 .74 
 
 .79 
 
 .05 
 
 .003 
 
 + .048 
 
 gydrogen 
 
 4.35 
 
 4. 34 
 
 4.96 
 
 .63 
 
 .005 
 
 + .615 
 
 Oxygen 
 
 4.Q5 
 
 4.04 
 
 4. 39 
 
 .35 
 
 .005 
 
 + .34 5 
 
 N itrogen 
 
 1.11 
 
 1.11 
 
 1.53 
 
 .41 
 
 .003 
 
 + .408 
 
 B. T. U, 
 
 15 444 
 
 15433 
 
 15643 
 
 330 
 
 30 
 
 + 200 
 
 Table 10. 
 
 , / 
 

 
 
 0, 
 
 Carbonization Tests of Coals, (10 Gr. Sample to 500 J. | 
 
 
 Illinois 
 
 Indiana 
 
 Alberta 
 
 Water (CaClJ 
 
 . 426 fo 
 
 .249% 
 
 . 539% 
 
 Water and Tar 
 
 1. 77 fo 
 
 2.0 5% 
 
 . 41% 
 
 Hydrogen Sulfide 
 
 .356% 
 
 .906% 
 
 none 
 
 Coke Left 
 
 6.75% 
 
 6.95% 
 
 9. 40% 
 
 Volume of Sas 
 
 500 cc 
 
 850 cc 
 
 600 cc 
 
 
 0 
 
 0 
 
 
 Formation Temp, of H^^S 
 
 410 C 
 
 340 C 
 
 - 
 
 
 0 
 
 
 0 
 
 Formation Temp, of Tar 
 
 410 C 
 
 - 
 
 480 C 
 
 Kind of Coke 
 
 Weak 
 
 Hard Dense 
 
 > 
 
 Powder 
 
 Table 11. 
 

 ^ -%<■« M u m ■ /f, 
 
 i* 
 
 ! fcvr _ 
 
 
 I 
 
 1 : 
 
 r t 
 
 ©MVIw® 
 
 T *“* '\ 
 
 
 jy.-. 
 
 V I .'■.■'■'■■SI? -'■* -'v . 
 
 >e? .,3f ■,^''-«, •■ 6*i!i 
 
 fik-«'J> I 9ft i . ft*- t^_i '• * ' 
 
 4m* — ^ 
 
 ' ' • ' ■- ■ ^;K' ‘ ■ ^^v■'i^i-:^;v:^■ :.. 
 
 0 
 
 a-jt 
 
 
 
 0 
 
 U ' Cp^ 
 
 .0 C5^ 1VH 
 
 c ■ ' 
 
 A 
 
 i'*;' 
 
 r-:^J "/I 
 
 ti:^ i i .it *i»v 1 
 
 -* ■ * # 1 ^ - -ii> ^ «fc 0Hr I u ' 
 
 ^ ^ 13 , 
 
 L''^ -.-■ > ‘‘ ,', ■ '.'. 'j' .n 
 
 •V.- ’A-iv"'*: '.'* . rfB- 'tZ,:'-.~ ,-! ■ i. ’^,-''1 i> , ;« 
 
 yi<. '^...■irf, ^ ■■/,.>.. ■‘‘’IS 
 
 |l/ 
 %«'.4 
 
 it "f 
 
 l‘- r..-.as*««r 
 
 (i* . * -.(jt-l’ 
 
 f^,s;rac?B=v ' -ai^^itcs 
 
 
 __ f . ■' :• N 
 j* j ,' 4' .,''v---'«y 7 
 
Carbonization Tests of Di-Phenyl Residues 
 
 5 Grs. to 500 degree 
 
 8 C. 
 
 
 Illinois 
 
 Indiana 
 
 Alberta 
 
 Water (OaCl^) 
 
 1 . 34f. 
 
 .43fo 
 
 
 Water and Tar 
 
 1 — 1 
 
 30^0 
 
 8 . 4f. 
 
 Hydrogen Sulfide 
 
 • 
 
 CO 
 
 • 
 
 C5J 
 
 CD 
 
 none 
 
 Coke Left 
 
 60< 
 
 66 f. 
 
 81 fo 
 
 Volume of Gas 
 
 10 5D CO 
 
 450 cc 
 
 500 cc 
 
 
 0 
 
 0 
 
 — 
 
 Formation Temp, of H^S 
 
 445 C 
 
 410 0 
 
 
 
 0 
 
 0 
 
 0 
 
 Formation Te-ip. of Tar 
 
 410 C 
 
 315 C 
 
 400 C 
 
 Kind of Coke 
 
 Powder 
 
 Powder 
 
 Powder 
 
 Table 12. 
 
PiPr"' 
 
 v: s,:ii:^- r T— ^:r' WV’^''' 
 
 ft 
 
 :v‘< i- 
 
 r.afcr: 
 
 
 ■ '4^ V. 
 
 • f*??* ' 
 
 -D 
 
 ^r f: . 'j- 
 
 i-r'* 
 
 t. --• '\w 
 
 
 
 ■f' 
 
 .mO.f, V ^ 
 
 . *^F* n • ' "* • 4 
 
 
 M ui 
 
 Vr i'"''- ■; ‘K^ ( ^OitS)) 
 
 ^^'6! '• I ^tfy»i.r«'ii»i iiii»i>»»<W(>lp»i f i i 4 i~" ' ''' 
 
 
 . • 4' 
 
 CO C^< i 
 
 
 '■i.'i 
 
 9 fcit R^ 3 ( 7 ^tH 
 
 .-T.. ^ •*'■ 
 
 .'“■ * .< 
 
 ,1 V.V 
 
 
 TO 
 
 i'' 0 ■- [ ^ . 
 
 i; ' ' ■' . . I 0 4X*,. f O'-f.'^X- ^,,H 
 
 ! 
 
 ■ ? w^. 
 
 l"» ’»‘ . 
 
 p$ r " * " *»*i 
 
 
 p ^£2^, r p c^r> kjof a'&- ■9,'^ 
 
 ■* .■». ....^Mi ^ . - I . . . . 
 
 
 ■w 
 
 1 ) . 
 
 
 v« 
 
 C, 
 
 ^ 'a' A 
 
 .,!-v.v^ ^ 
 
 ♦v>.‘- .Jh* 
 
 •>x •> ' . ■^•: 4 
 
 V -,-'B V. ,. V, -^rj y— 4 If' 
 
 ’ , '■ '* t ' ' I 4 ' 
 
 ► > - i • Uf 
 
 Vi'-f-!§<^’ ■"''^ 
 
 '.‘7 ■r*^';<..)--jj..L 
 
 r... '.' : : 
 
 Vs 1 
 
 - i>\j 
 
 
 a .1 
 
 ‘‘w 0 ' ■' ■ I f A ■ ■ ■>> y w~ ' 
 
 O ^ .,.l|it*i' ■ . J'‘„ • ’.^ 
 
 wt. '/A*; ^ 
 

 Carbonization Tests of Alcoholic Rotash Residues 
 
 0 
 
 5 grs. to 500 C. 
 
 
 
 Illinois 
 
 Indiana 
 
 A1 berta 
 
 Water (CaClp.) 
 
 1 1c 
 
 1.S4 1 
 
 1.78 1 
 
 Water and Tar 
 
 10 1 
 
 16 1o 
 
 00 
 
 Hydrogen Sulfide 
 
 Hone 
 
 .25 $ 
 
 None 
 
 Coke Left 
 
 CO 
 
 73 1o 
 
 CO 
 
 CO 
 
 Volume of Gas 
 
 500 CO 
 
 650 CO 
 
 600 cc 
 
 Formation Tenp. of HS 
 
 V 
 
 
 0 
 
 420 C 
 
 
 Formation Temp, of Tar 
 
 410o C 
 
 0 
 
 375 C 
 
 0 ' 
 410 C 
 
 Kind of Coke 
 
 . . 
 
 Powder 
 
 Powder 
 
 Powder 
 
 Table 13. 
 
- f ' f ' ;.— ■‘•'•\r''^«eag s^r^T/'.w^' ;■ 
 
 te-’r^-^-ilSii V j ", ^^.j) '< ’iT- >r^ i i ■ 
 
 i 'i H|P!V '■' 
 
 -..If#-. .', . i 7 ,Tr',-teJ . ' . ■’«■_■•'?-£ 
 
 t. 
 
 '■• *1 
 
 ''■ I 
 
 i' ' - . 
 
 I I . ' 
 
 
 ■'. ■ '^rr':-s.> . 
 
 V 'Vi?, TV 
 
 . A, .-■ * ^ :• '. V-frVif . r';- UJ 
 
 ■ a;J •• . ’-L' 
 
 I • ' V* 
 
 ■•> #■' 
 
 
 F , 
 
 
 -D? 
 
 «VJC c 
 
 ■ 
 
 t ‘ H ‘‘V rTrLOClX/ 
 
 r ^1 i^ ' 
 
 :-r* . 
 
 
 r Sa' • '' 
 
 o 
 
 
 • V 
 
 
 
 7 ' J)- 
 
 -■ t: 
 
 J 1 JI' 
 
 '^"~l=y . ' g '*'* *?**» " " r »l<« #^ lii i^ ,i l r -w.^./^ 
 
 rT 4 & ■ ■ 
 
 , .,^v 
 
 < < V I 
 
 hi Hv. i. ., / 4 .^ <• ■ ■ .' ,. 
 
 • " ^ •* - -•~>*’‘* ' *»- ■ I i» « jiiitii < 4i -n Xi .^ -^- w ■ «iij^ i i^,^..i..<i^i|^ -I — in » « i» iiiiwi( S .i»>t4U ^ fi'<iM t y ■ 
 
 mi; Vi 
 
 V 
 
 !! 
 
 <a 
 
 I 
 
 ‘^ 40 - ' 
 
 
 ■ ' - tir9*,Vi(d5c«p4^^ -4|; 
 
 
 L ■ H' ^ais /‘-*yV-7VtJ^9ii(oo jy 
 
 1 . ‘"^:’bs 
 
 ' 1 . ti ' 
 
 »4i 
 
 vt> 
 
 > 
 
 il^V-ro -‘iQ^T 
 
 'X. - -. t 
 
 ..siJjjrT B 
 
 - - •■■^ • iti Wmii — »'«|i’ n »' I i>i I i |rgwi y i . -;: /vr 
 
 ^ L ' Vp^’rfl 
 
 . ..' ■,<' 1 ?.V,;;. .Si-' 
 
 • **iii •' -f iV II* 
 
 r ll ’U ' ' '■ ' '■ 
 
 . . . . ; .. lA- V' ',7 7 '- 
 
 ,.p 
 
 “ ' I.-. > . •■ 1 ;., fC ■' & ■ ‘ ' 
 
 
 fit- v 7 'A 
 

 
 - 
 
 
 Analysis of Gases from Carbonization of Coal 
 
 Nitrogen Free 
 
 
 j 
 
 1 
 
 1 
 
 1 
 
 1 
 
 i 
 
 Percent Gases 
 
 Illinois 
 
 Indiana 
 
 Alberta 
 
 Carbon Dioxide 
 
 16.8 
 
 6.3 
 
 11.0 
 
 Oxygen 
 
 15. a 
 
 40. 4 
 
 19.4 
 
 Unsat. Hydrocarbon 
 
 3.8 
 
 4.8 
 
 3.3 
 
 Aromat. Hydrocarbon 
 
 1.8 
 
 1. 3 
 
 .6 
 
 Hydrogen 
 
 10. 4 
 
 7.0 
 
 f= 
 
 1 
 
 CO 
 
 1 — 1 
 
 Carbon Monoxide 
 
 4.8 
 
 4.14 
 
 6.8 
 
 Methane 
 
 31.3 
 
 CO 
 
 • 
 
 o 
 1 — 1 
 
 31.0 
 
 Eth \ne 
 
 15.6 
 
 35. 3 
 
 -10.6 
 
 Table 14. 
 

 
 V 
 
 •• r • 
 
 
 
 1 
 
 
 * '4«A 
 
Analysis of Oases from Carbonization of Diphenyl Ether 
 Residues, Nitrogen Free. 
 
 Percent Oases 
 
 Illinois 
 
 Indiana 
 
 Alberta 
 
 Carbon Dioxide 
 
 11.5 
 
 8.8 
 
 18.6 
 
 Oxygen 
 
 43.4 
 
 CO 
 
 • 
 
 1 — 1 
 to 
 
 41.6 
 
 Unsat. Hydrocarbon 
 
 1.6 
 
 4.3 
 
 3jk-l— . . . 
 
 Armat. Hydrocarbon 
 
 1.1 
 
 .9 
 
 0 
 
 Hydrogen 
 
 11.5 
 
 3.0 
 
 33. 4 
 
 Carbon Monoxide 
 
 8.1 
 
 4.0 
 
 3.0 
 
 Methane 
 
 33.8 
 
 48. 3 
 
 13. 3 
 
 
 Table 15. 
 
Analysis of Gases from the Carbonization of 
 Potash Residues, Nitrogen Free 
 
 Alcoholic 
 
 Percent Gases 
 
 Illinois 
 
 I nd i ma 
 
 Alberta 
 
 Carbon Dioxide 
 
 21.4 
 
 43.7 
 
 27.8 
 
 Oxygen 
 
 42.3 
 
 14.1 
 
 24.6 
 
 Unsat. Hydrocarbon 
 
 2.3 
 
 3.2 
 
 1.1 
 
 Arma t . Hy d ro c arb on 
 
 1.1 
 
 . 7 
 
 0 
 
 Hydrogen 
 
 4. 3 
 
 5.2 
 
 16.2 
 
 Carton Monoxide 
 
 2.3 
 
 3.2 
 
 2.5 
 
 Methane 
 
 26.3 
 
 30.9 
 
 
 27.8 
 
 
 
 
 
 
 Table 16. 
 
 1 f 
 
Volume of Gases from 100 Grams of Coal, Nitrogen Free 
 
 I 
 
 cc per 100 grs. 
 
 Illinois 
 
 Indi;ana 
 
 A1 be rta 
 
 Carbon Dioxide 
 
 840 
 
 530 
 
 660 
 
 Oxygen 
 
 775 
 
 3440 
 
 1164 
 
 Unsat. Hydrocarbon 
 
 193 
 
 398 
 
 134 
 
 , - . Armat . Hy dro c arb on 
 
 93 
 
 109 
 
 36 
 
 Hydrogen 
 
 531 
 
 ' 597 
 
 1108 
 
 C_arbpn Monoxide 
 
 340 
 
 353 
 
 1 4 
 
 409 
 
 Methane 
 
 1561 
 
 904 
 
 1860 
 
 Ethane 
 
 775 
 
 3169 
 
 639 
 
 Total Volume 
 
 5000 
 
 8500 
 
 6000 
 
 Table 17, 
 

 ^ , 
 
 ‘ , s 
 
 vc7^ Ito C9«i0 OOiT e)6t4p3^ ' 
 
 , , 4 ' ^\] ‘ "■ 
 
 :f ■. 
 
 .\ 
 
 
 r "■<>^- 
 
 r'S-'>r » 
 
 
 *^i^<ifl * I 
 
 « ' ' ■ ' 'A 
 
 Ji 
 
 ^ i. n 
 
 
 [;y.’-i?! f 
 
 . '*•» I - Ifl^ 
 
 ■» 9 I„ -ijf-.: .41 
 
 :.ivt ct.., 
 
 iH. . 
 
 , ■ . - . , ■ '^it»'*'‘’'‘ -*r 
 
 rr • I f •' t\ >b'- "' ^ , «» ^ i 
 
 '■'■ -t4>' \'^ ^^^Sitlii■o^,> 
 
 r •- -t *• 
 if ; . 
 
 f>v ^ f’“*^ ',L^ ^. ■- J 
 
 F3;/ f%' 
 
 t ;, !' ^ ''ii' ife 
 
 etT ,, : 
 
 I. ,4. ^ 
 
 I." 'i'^'pSr: 
 
 , -'**-•► 44 * 
 
 ®: «*:oV.li'/i^ '*’- 
 
 V'i 
 
 • _/ '■' ■'« •■»' 
 
 M 
 
 ! 1 
 
 *^» ' t> I 
 
 
 ,> "f ,tf 
 
 
 
 
Volumes of Gases from 100 grs. of Di-phenyl Residues 
 Nitrogen Free 
 
 CC per 100 Grs. 
 
 111 ino is 
 
 Indi^ana 
 
 Alberta 
 
 Carbon Dioxide 
 
 2430 
 
 794 
 
 1860 
 
 Oxygen 
 
 9120 
 
 3860 
 
 4160 
 
 Unsat. Hydrocarbon 
 
 336 
 
 378 
 
 310 
 
 Armat. Hydrocarbon 
 
 331 
 
 81 
 
 0 
 
 Hydrogen 
 
 2430 
 
 180 
 
 2240 
 
 Carbon Monoxide 
 
 1700 
 
 360 
 
 200 
 
 Methane 
 
 47 73 
 
 4367 
 
 1Z3CL, 
 
 Tdjtal Volume 
 
 21000 
 
 9000 
 
 10000 
 
 Table 18. 
 

 A.t, 
 
 .'■■■ . . ■ ■ \T''% >' ■ 
 
 Xv.'?i y.x> . ^73?. 001 M'rJ’ To 
 
 > ! 
 
 
 
 i/'. ., 
 
 . i 
 
 ‘n 
 
 
 {«/; rEi>£ 
 
 4 ’.' ^i» 
 
 j 
 
 
 
 tl. 
 
 I 
 
 . 'CXO.,. 
 
 ^ev 
 
 MHiM -. A. . . 
 
 ■ 
 
 . -5aR?^_ 
 
 ,'■ I*;-.' 
 
 *■' ' i’fr 
 
 J.' w& 
 
 "i-*- ■' -f<lkAite — - •«** #**♦ vWi W-UBR .Am; 1 1 mn w yip *£* 
 
 . ■ ' ' !"'■'■ '"■ 
 
 .. > >.-'_-06I, ■>[ 
 
 ' - '\ *•« "•••'-' '>■• . 
 
 ; I ‘ 1 'jfti'ioiCE- k6#»!j0 > 
 
 -*T ••••• •'>*,_ *• •♦^•-•; 1 1 # <m>* i p y lib «<it* i *«*>- 
 
 ‘-^ i . 
 
 i - .,'. 
 
 
 "i -» 
 
 vO!' 
 
 
 s 
 
 
 
 
 ' \it: 
 
 
 ‘5r: 
 
 
 '.'"■ ;'T- 
 
 
 
 
 ,- ^>: ' tm' 
 
 “ 3 ■ ’ • 
 
 ^-■ 
 
 '/% '|s1b 
 
 rotmr ;, ,|ir 
 
 . • '7 
 
 ‘ .A J r 
 
 ;..v» 
 
 
 I . 
 
 t- 
 
 i .’* • 
 
 K V 
 
 . A .-V 
 
 , . .'•■’’■ 3n-'n 
 
 :>V.,.i ^ 
 
 j .S 
 
 r 
 
 V( \ 
 
 :i*vv'"*'- 
 
 .. ■Ji 
 
 ■ . v>^l;A^;;' ;i , 
 
 ■ .: ' ' ■ ■ ■ if. :lt- '#! i_-W -ij 
 
 • -,ic" ,'d' 'V^-^i, -t' ...>i.«il«,»lW^ r‘^-ikii 
 
 
 
 
 » *■ 
 
 'i' - 
 
 r. ^* ■ 
 
 * ? 
 
 
 
 
 U. r 
 
 • » >f, * 
 
 s I* , . • |V , 
 
 ‘ -V- Ji ^»*■• 
 
 #■'’'.*5 Sfc t'' 
 
 .'it -ardW ■ ''■■■./I • ., V ’ ;-i 
 
 ':J 
 
 ■; 'V.;/ 
 
 ^y^JSTT>3^>- . 
 
 3 ^ 
 
 f. '• 
 
 — Y^ T»« « 
 
 ,i. 
 
 ’i ■ ' 'V ’ 
 
 s 
 
 » '{,■ 
 
 't ■“ 
 
 . V 
 
 -■ 
 
 
 
 (A' L 
 
 '■xs. ju t m utei- 
 
 •• ,\| "' C \. . ' . ■ ■ ■ ^.' 
 
 
Volume of Gases 
 
 from 100 Grs. Alcoholic Potash Residues 
 Nitrogen Free 
 
 CC uer 100 Grams 
 
 Illinois 
 
 Indiana 
 
 Alberta 
 
 Carbon Dioxide 
 
 3140 
 
 55 50 
 
 3 780 
 
 Oxygen 
 
 4330 
 
 1830 
 
 3460 
 
 Unsat. Hydrocarbon 
 
 330 
 
 416 
 
 110 
 
 A rm at . Hy dro c ar bo n 
 
 11 0 
 
 91 
 
 0 
 
 Hydrogen 
 
 430 
 
 675 
 
 1630 
 
 Carbon Monoxide 
 
 330 
 
 416 
 
 350 
 
 Methane 
 
 3630 
 
 4033 
 
 3780 
 
 Total Volume 
 
 10000 
 
 13000 
 
 10000 
 
 Table 19. 
 
- 10 - 
 
 IV. Discussion and Conclusion. 
 
 Di-phenyl ether will remove the coking property 
 of coal. It, however, does not remove all of the resinic 
 mattery for the residue will give tar v/hen carbonized and an 
 extract when treated with alcoholic potash. For two of the 
 samples the ash on the residue is practically equally to the 
 amount of the ash contained in the original coal. This indicates 
 that di-phenyl ether is a true solvent. 
 
 The residue from the di-phenyl ether extraction can 
 be handled easily, and after washing with ethyl ether it can 
 
 be crushed, to a fine powder without any difficulty. 
 
 19 
 
 The H:0 ratio as proposed by ??hite for a guide 
 to the coking power, holds true in all the carbonization tests. 
 The Indiana Coal is the only one that had a hydrogen tO' oxygen 
 ratio greater than 59, and it is the only one that produced 
 a good coke. ^ 
 
 From Table 1 it can be seen that the amount of 
 material extracted does not depend upon the time of extraction 
 to any great extent. Also, it is not necessary to keep the 
 
 solvent It its boiling point. The temperature, however, 
 
 o 
 
 should not be below 200 C. , because under such conditions the 
 coal will Ccike in the bottom of the flask, and it is more 
 difficult to filter the relative coal solution. 
 
 The volatile matter on all the residues is higher 
 than on the original coal. This iS due to traces of the sol- 
 vent that were not removed in washing the residues. This fact 
 

 
 ,r 
 
 i 
 
 V- .. f -I 
 
 "I . J 
 
 »r^ljs;iii'ncvl. fr*/: rfOito^u^c vM,. > 
 
 ■H .'.1 
 
 
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 »i' »■ , 
 
 rMt «ri 6 fW r'tl» 7 .-^ofj %tt .LeoC'lo 
 
 .'"'■ -, \ tfl. - j ' -. 
 
 udi \a irt^ ^Xtml 0 ciJf‘ d/i# 
 
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 4 ' 
 
 ■f->‘''l '>• . ‘ I "it 
 
 »ii-t 0^ ritj >/r^ vtx^oi;toAt‘: $jf f«rfrt-a9x •■ 
 
 • "■■•< tji ^ ■ '••f i 
 
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 aWT tiv« -U .^mria^^iiPo disiS 
 
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 'i^i' 
 
 ^ . \4 
 
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 ' ff 9 ;< 5 yfo- 04 ^ . i «4 sn<? vi^io (si 
 
 Spoolio-l^ iTk.t^ tiiSO M£ Oitr** ’ 
 
 
 *Vi> 
 
 ’ . io ’^n'.cpiluj:/ nilf 
 
 -*■ 
 
 ..V' 
 
 ■ 
 
 F- ; 
 
 np 5 » >?Cf' .f- 
 
 ':a ac^ Apficiet JPr'^«'-eab 
 
 fe"'" V.' ' ■ ■ ‘ ' ■ ,E:^i 
 
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 ■x-'j i:ictj}'tun ^om r^’w op^jlrotnii iL 
 
 f ,^7 
 
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 ,,. T^-^riX'ii:. ajjitfi. , fX4\rtb'^ ■£a.tf;f»;(r..'p,fi*ff- r^sv- W? 
 
 KS 
 
 . / 
 
 -— J <i; 
 
 -r£op *!<? ef 0 £ Vii of- Vil W'tpft '.Z^PpF^nijj.txo «4i^: ffo^a,^/f;r 
 
 ^-I’l airf?' . ^lii tii ;t:id^v|',* 
 
 
 
 I .-'Ak 4 l 
 
 
 ■ JflV" J 
 
- 11 - 
 
 isalso shown in the balance sheets, tables 5, 6 and 7, in 
 
 which hydrogen shows an increase in two cases, while the 
 
 ox3'-gen has increased in one. The increase in oxygen could 
 
 be due to the solvent tSieat had been left in the residue or 
 
 18 
 
 to absorption of oxygen from the air. Cherry, working with 
 
 phenol, found that the residue shows an avidity for oxygen. 
 
 The alcoholic potash residues show a decrease 
 
 in volatile matter for two of the samples, while the oxygen 
 
 content shows an increase on the siune samples. The difficulty 
 
 in using alco’olic potash lies in the fact that if the residue 
 
 is not carefully washed, some of the KOH will remain in the 
 
 residue. This is what happened with the Indiana residue where 
 
 the ash on the original coal was 9.33 percent and 34.99 percent 
 
 on the alcoholic potash residue. It was found that if the 
 
 residue was placed in a beaker inrith water and acid added until 
 
 potash 
 
 the solution v/as neutral, the ash on the alcoholic residues 
 
 will be very close to the values on the original coal. 
 
 The gases from the carbonization of the alcoholic 
 
 potash residues show increases in carbon dioxide. This 
 
 increase is partially due to oxidatioi or to absorption of carbon 
 
 dioxide by the alkaline solution. Carbon monoxide is lower 
 
 on the alcoholic potash residues, showing that part of it mi^it 
 
 have been converted into carbon dioxide during the extraction 
 
 process. The carbon dioxide on two of the di-phenyl ether 
 
 residues show an increase' and one shows a decrease. Parr 
 17 
 
 and Hadley said that any increase in carbon disxide on the 
 residue from a phenol extraction, was due to oxidation. ; 
 

 
 , i 
 
 
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 r 
 
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 ■ . f I' 
 
 
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 • X ' ' V ' ' r ^ 
 
 ,afiIT ■ . ' -^I']‘ft$B m-,v 'ir.^ .08 swo^a V- 
 
 * '" K- t. '; 
 
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 Carbon monoxide decreases on the coals where carbon dioxide 
 
 increases and increased on the sample that showed a decrease 
 
 of carbon dioxide on the di-phenyl ether residue. According 
 
 20 
 
 to Porter and Taylor carbon dioxide and carbon monoxide come 
 from cellulosic materials, so it would be naturcil to expect 
 an increase on the residues which contain a higher percent of 
 cellulosic material. 
 
 V. Summary. 
 
 1. The products of Di-phenyl ether extraction are 
 in such a condition that they can be easily handled. 
 
 2. Time over six hours does not increase the amount 
 of extracted material. 
 
 3. The temperature does not have to be at the boilipg 
 
 0 
 
 point of di-phenyl ether, but it should not be below 200 C. 
 
 4. The ' 3 :e si due 8 from both di-phenyl ether and alcoholic 
 potash extractions show an avidity for oxygen. 
 
 5. It is impossible to remove di-phenyl ether completely 
 from the residue. 
 
 6. Di-phenyl ether does not remove all of the resinic 
 matter, but it leaves a residue that will not coke. 
 
 7. The ash on the di-phenyl residue can be usually 
 checked back to the value orir the original coal, showing that 
 di-phenyl ether is a true solvent of the coal substance. 
 
 8. Di-phenyl ether is a much better solvent than 
 either phenol or pyridin, because it is easier to 7;ork with 
 than phenol and will not form addition products as pyridin 
 will do. 
 
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- 13 - 
 
 9, The use of alcoholic potash is not as 
 
 advant eous as that of di-phSnyl ether, because it is very 
 easy for the residue to absorb carbon dioxide, and the 
 residue must be I'^c^shed very carefully in order to remove all 
 of the alcoholic potash. 
 
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- 13 - 
 
 VI. Bibliography 
 
 1. Bulletin #82, U.S.G.S. 
 
 Bulletin #38, Bureau of Mines 
 
 2. Thesis, University of Illinois, 1921. 
 
 3. Bulletin, University of Illinois, Engineering Experiment 
 
 Station, No. 111. 
 
 4. Jour. Chem. Soc. Vol. 48, page 876. 
 
 5. Jour. Soc. Chem. Ind. 1898, page 1013. 
 
 0 , M ti 11 11 Vol. 20, page 789. 
 
 7 ^ 11 11 II « ” 21, page 242 
 
 S, II II « ” ” 27, page 150 
 
 9. Progressive Age. Vol. 29, page 1030. 
 
 10. Annalen. Vol. 399, page 120. 
 
 11. Berichte, Vol. 44, page 2486. 
 
 12. Compt . Rendus. Vol. 158, page 1421. 
 
 13. Berichte, Vol. 49, page 1460. 
 
 14. Comt. Rendus: Vol. ’ 154, page 1094. 
 
 Bulletin Soc. Chem. Vol. 21, page 78. 
 
 15. Jour. Oh:pm. Soc., Vol. 103, p?ge_ 1704. 
 
 16. Tech. Pa.per, Bureau of Mines, No. 5. 
 
 17. Bulletin Univ. of 111. Eng. Expt. Stat. No. 76. 
 
 18. Thesis University of Illinois, 1920. 
 
 19. Bulletin, Bureau of Mines, No. 29, 1911. 
 
 20. Technical Paper 140, Department of the Interior.