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4] THEORY OF GENERAL TECHNIQUE 9 number of distillations necessary for reasonably complete separation of the two liquids. A fractionating column is designed to provide a continuous series of partial condensations of the vapour and partial vaporisations of the condensate and its effect is, indeed, similar to a number of separate distillations. The effect of partial condensation will be evident from Fig. /, 4, 2. If the temperature of the vapour is lowered, it will partly condense giving a hquid richer in B and leaving the vapour richer in A. The vapour passing up the column will accordingly contain more of A than did the vapour which left the boiling liquid. Similarly the hquid returning to the flask will contain relatively more of the less volatile component B. A fractionating column consists essentially of a long vertical tube through which the vapour passes upward and is partially condensed; the condensate flows down the column and is returned eventually to the flask. Inside the column the returning hquid is brought into intimate contact with the ascending vapour and a heat interchange occurs whereby the vapour is enriched with the more volatile component A at the expense of the hquid in an attempt to reach equihbrium. The conditions necessary for a good separation are :—(i) there should be a comparatively large amount of hquid continually returning through the column ; (ii) thorough mixing of hquid and vapour ; and (iii) a large active surface of contact between liquid and vapour. Excessive cooling should be avoided ; this difficulty is particularly apparent with liquids of high boiling point and may be overcome by suitably insulating or lagging the outer surface of the column or, if possible, by surrounding it with a vacuum jacket or an electrically heated jacket. Various types of laboratory fractionating columns are described in Sections II, 15-11,18. (2) Minimum boiling point. Typical boiling point - composition curves for systems of this kind are shown in Fig. /, 4, 4. If a solution of composition Lx is heated, the vapour pressure will rise until at the point lx it is equal to the pressure of the atmosphere and boiling commences at tv The composition of the vapour first distilling is Vv As the boiling proceeds the temperature rises from tx to t2f and during this period distillates with compositions ranging from Vx to V2 will be obtained. If the distillate be redistilled, the vapour approaches the composition of the minimum boiling point system, as can be seen from the figure. Hence fractional distillation will result in a distillate of composition Lm, although the final residue will approach A. Similarly, a solution of composition L{ when distilled commences to boil at Z/, i.e., at a temperature tx' the vapour (and therefore the distillate) will have the composition Vx'. As the distillation continues the composition of the vapour changes to V2' and the hquid to L2'. Fractional distillation will, in this case, yield a solution of composition L^hf and the residue will approach B. The hquid mixture can then be separated only into the component present in excess (either A or B) and the mixture of minimum boiling point. The liquid represented by Lm will distil over completely without change of composition since at the boiling point the vapour has the same composition as the liquid. Such systems which distil unchanged are called azeotropic mixtures (Greek : to boil unchanged). The composition and boiling point of such constant boiling point mixtures vary with the pressure and consequently they are not chemical compounds.
10 PRACTICAL ORGANIC CHEMISTRY P. L* U V» V, lOO^A Composition Fig. /, 4, 4. IOO;#B Examples of azeotropic mixtures of minimum boiling point are collected in Table 1,4, A. TABLE I, 4, A. AZEOTROPIC MIXTURES OF MINIMUM BOILING POINT COMPONENT A Water, 100-0° Water, 100-0° Water, 100-0° Water, 100-0° Water, 100-0° Methyl alcohol, 64-7° Ethyl alcohol, 78-3° Methyl alcohol, 64-7° Ethyl alcohol, 78-3° Water, 100-0° Water, 100-0° Benzene, 80-2° Ethyl alcohol, 78-3° Ethyl alcohol, 78-3° Methyl alcohol, 64-7° Ethyl alcohol, 78-3° Ethyl alcohol, 78-3° Methyl alcohol, 64-7° Acetic acid, 118-5° (3) Maximum boiling point, diagram is shown in Fig. /, 4, 5. COMPONENT B Ethyl alcohol, 78-3° tsoPropyl alcohol, 82-4° n-Propyl alcohol, 97 • 2° tert.-Butyl alcohol, 82-6° Pyridine, 115-5° Methyl iodide, 44-5° Ethyl iodide, 72-3° Methyl acetate, 57 • 0° Ethyl acetate, 77-2° Butyric acid, 163-5° Propionic acid, 140-7° cycJoHexane, 80-8° Benzene, 80-2° Toluene, 110-6° Chloroform, 61-2° Chloroform, 61-2° Methyl ethyl ketone, 79-6° Methylal, 42 • 2° Toluene, 110-6° B.p. OP AZEOTROPIC MIXTURE 78-15° 80-4° 87-7° 79-9° 92-6° 39-0° 63 0° 54-0° 71-8° 99-4° 100-0° 77-5° 68-2° 76-7° 53-5° 59-4° 74-8° 41-8° 105-4° % OF A (BY WT.) IN MIXTURE 4-4 12-1 28-3 11-8 430 7-2 13 19 31 18-4 17-7 55 32-4 68 12-5 7-0 40 18-2 28 A typical boiling point - composition By reasoning analogous to that given
Page 1 and 2: A TEXT-BOOK OF P R A C T I C A L O
Page 3 and 4: PREFACE TO THIRD EDITION THE favour
Page 5 and 6: PREFACE TO FIRST EDITION vn the new
Page 7 and 8: CONTENTS CHAPTER I THEORY OF GENERA
Page 9 and 10: CONTENTS xiii PAGE 11.58. Apparatus
Page 11 and 12: CONTENTS xv PAGE 111.76. n-Heptaldo
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Page 21 and 22: CONTENTS XXV PAGE 1X,7. Diethylbarb
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60 PRACTICAL ORGANIC CHEMISTRY [II,
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64 PRACTICAL ORGANIC CHEMISTRY III.
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66 PRACTICAL ORGANIC CHEMISTRY [H.
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72 PRACTICAL ORGANIC CHEMISTRY [II.
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u PRACTICAL ORGANIC CHEMISTRY [II,
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M PRACTICAL ORGANIC CHEMISTRY [II.
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90 PRACTICAL ORGANIC CHEMISTRY [H,
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96 rRACTICAL ORGANIC CHEMISTRY [II,
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102 PRACTICAL ORGANIC CHEMISTRY [II
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11% PRACTICAL ORGANIC CHEMISTRY PL
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114 PRACTICAL ORGANIC CHEMISTRY rn,
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122 PRACTICAL ORGANIC CHEMISTRY [IL
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138 PRACTICAL ORGANIC CHEMISTRY PL
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156 PRACTICAL ORGANIC CHEMISTRY [M.
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172 PRACTICAL ORGANIC CHEMISTRY [«
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176 PRACTICAL ORGANIC CHEMISTRY in.
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206 PRACTICAL ORGANIC CHEMISTRY [">
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228 PRACTICAL ORGANIC CHEMISTRY [11
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234 PRACTICAL ORGANIC CHEMISTRY [HI
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246 PRACTICAL ORGANIC CHEMISTRY [IU
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250 PRACTICAL ORGANIC CHExMISTRY [H
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252 PRACTICAL ORGANIC CHEMISTRY fil
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TABLE 111,27. Alcohol Diacetone alc
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TABLE 111,42, Halide ALIPHATIO HALO
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TABLE 111,42. ALIPHATIC HALOGEN COM
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TABLE 111,70. Formaldehyde Aldehyde
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344 PRACTICAL ORGANIC CHEMISTRY [Hi
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TABLE III, 74. ALIPHATIC KETONES Ke
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TABLE 111,85. ALIPHATIC CARBOXYLIC
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394 PRACTICAL ORGANIC CHEMISTRY I H
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396 PRACTICAL ORGANIC CHEMISTRY TAB
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412 PRACTICAL ORGANIC CHEMISTRY [in
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TABLE 111,123. Amine Methylamine Et
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TABLE 111,132. AMINO ACIDS—Contin
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TABLE 111,136. POLYHYDRIC ALCOHOLS
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LACTOSAZONE MALTOSAZONE CELLOBIOSAZ
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CHAPTER IV AROMATIC COMPOUNDS AROMA
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510 PRACTICAL ORGANIC CHEMISTRY [IV
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TABLE IV,9. Hydrocarbon Diphenyl .
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530 PRACTICAL ORGANIC CHEMISTRY Liv
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TABLE IV.28. AROMATIC HALOGEN COMPO
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552 PRACTICAL ORGANIC CHEMISTRY [VI
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562 PRACTICAL ORGANIC CHEMISTRY (IV
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TABLE IV,100A. Amine Aniline . o-To
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TABLE IV,100A. PRIMARY AROMATIC AMI
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TABLE IV,100C. Amine p-Bromodimethy
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668 PRACTICAL ORGANIC CHEMISTRY tiv
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TABLE IV,106. AROMATIC ETHERS (cont
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TABLE IV,114. PHENOLS (continued) P
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TABLE IV,U4A. ENOLS Compound Acetyl
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702 PRACTICAL ORGANIC CHEMISTRY LIV
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718 PRACTICAL ORGANIC CHEMISTRY tiv
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TABLE IV,135. AROMATIC ALDEHYDES [c
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TABLE IV,148. Ketone Benzophenone p
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TABLE IV,152. Quinone Thymoquinone
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TABLE IV.175. Add Benzoic o-Toluic
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TABLE IV,205. Alcohol Benzyl P-Phen
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CHAPTER V SOME HETEROCYCLIC AND ALI
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830 PRACTICAL ORGANIC CHEMISTRY [V,
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834 PRACTICAL ORGANIC CHEMISTRY [V.
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888 PRACTICAL ORGANIC CHEMISTRY IV1
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910 PRACTICAL ORGANIC CHEMISTRY IVI
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CHAPTER IX SOME PHYSIOLOGICALLY ACT
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998 PRACTICAL ORGANIC CHEMISTRY [IX
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1000 PRACTICAL ORGANIC CHEMISTRY [I
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1010 PRACTICAL ORGANIC CHEMISTRY fi
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CHAPTER X SYNTHETIC POLYMERS X,l. B
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1016 PRACTICAL ORGANIC CHEMISTRY [X
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CHAPTER XI QUALITATIVE ORGANIC ANAL
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1034 PRACTICAL ORGANIC CHEMISTRY 1X
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TABLE XI,5,1. DIVISION OF ORGANIC C
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1074 PRACTICAL ORGANIC CHEMISTRY IX
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1088 PRACTICAL ORGANIC CHEMISTRY TA
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TABLE XI,9,2. GENERAL SCHEME FOR SE
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1116 PRACTICAL ORGANIC CHEMISTRY [A
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TABLE A,8,2. 1 PER CENT. CH8OH BY 1
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TABLE A,8,5. AQUEOUS NITRIC ACID PE
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TABLE A,8,9. PER CENT. HBr BY WEIGH
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TABLE kfi,12. AQUEOUS AMMONIA SOLUT
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TABLE A,8,/6. AQUEOUS POTASSIUM CAR
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A,9. DENSITY AND VAPOUR PRESSURE OF
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INDEX Page numbers in bold-faced ty
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a-Amino-n caproic acid, 427, 432 4-
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a-Benzilmonoxime, 720 P-Benzilmonox
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m-Chlorobenzoic acid, 929, 932 o-Ch
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Diethylaniline, 562, 573 purificati
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p-Ethylbenzyl chloride, 540 Ethyl b
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Halogen carriers, 533 Halogen compo
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Magnesium sulphate, as desiccant, 4
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m-Nitroaniline, 563, 574 7>-Nitroan
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a-Picoline, purification of, 177 p-
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Semimicro apparatus—cord, distill
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Thermometers, 72 calibration curve
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