`
`KENNETH B. WEBERG
`
`Professor of Chemistry
`
`Um'rue'rsity of memgtmz
`
`McGRAW-HILL BOOK COMPANY,
`
`INC.
`
`1960
`
`New York
`
`Toronto
`
`London
`
`Liquidia - Exhibit 1010 - Page 1
`
`Liquidia - Exhibit 1010 - Page 1
`
`

`

`LABORATORY TECHNIQUE IN ORGANIC CHEMISTRY
`
`Inc‘. Printed
`Copyright © 1960 by the McGraw—Hill Book Company,
`in the United States of America, A11 rights reserved. This book, or
`para thereof,rnay not be reproduced in any fornlkahout pernfisdon
`of the publishers. Library of Congress Catalog Card Number 59—11950
`IV
`
`70095
`
`THE NIAPLE PRESS COMPANY, YORK, PA.
`
`Liquidia - Exhibit 1010 - Page 2
`
`Liquidia - Exhibit 1010 - Page 2
`
`

`

`
`
`PREFACE
`
`Although there are a number of monographs available which deal
`with an aspect of the techniques required in dealing with organic com—
`pounds, there has for some time been no book which gives a brief de—
`scription of most of the important techniques. This book is written in
`an effort to fill this need and is directed mainly to the advanced un—
`dergraduate or beginning graduate student who is about to undertake
`a program of research work.
`Each of the three types of matter, liquids, solids and gases, is con-
`sidered with respect to both its properties and the methods of puri—
`fication. It
`is
`felt
`that an understanding of the properties of the
`substances adds materially to the appreciation of the methods of puri—
`fication. Methods which involve distribution between two phases are
`then considered. Finally, the reaction itself is examined in relation to
`the apparatus and techniques involved.
`the use of the proper
`In organic chemical
`laboratory technique,
`apparatus is important. A drawing of a commonly used piece of equip~
`ment has generally been provided to accompany the description of
`each method. These drawings are for the most part derived from the
`working drawings used in the shops at the University of Washington,
`and in most cases all important dimensions are given in millimeters,
`In writing a book of this type, it is very difiicult to give credit to
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`Liquidia - Exhibit 1010 - Page 3
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`Liquidia - Exhibit 1010 - Page 3
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`

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`Liquidia - Exhibit 1010 - Page 4
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`

`

`
`
`viii
`
`Contents
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`Chapter3.Gases................]20
`PHYSICAL PROPERTIES or GASES.
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`120
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`Pressure. Vapor Density. Heat Capacity and Thermal Con~
`tluctivity.
`PURIFICATION OFGASES.
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`129
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`Vacuum Lines. Pumping System. Vacuum Manifold. Toepler
`Pump. Stopcocks
`and Lubricants. Simple Distillation.
`Frac—
`tional Distillation. Diffusion. Purification of Gases by Chemical
`Methods.
`
`Chapter 4. Adsorption and Extraction
`ADSORP’I'ION
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`149
`14-9
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`Distribution between Liquid and Solid Phases. Adsorbents.
`Standardization of Adsorbcnts. Effect of the Structure of the
`
`Solute on the Degree of Adsorption. Batchwise Adsorption and
`Decolorization. Chromatography. Advantages and Limitations
`of Chromatography. Partition Chromatography and Paper
`Chromatography. Vapor-phase Chromatography.
`[on Exchange.
`EXTRACTION.................179
`
`Simple Extraction. Continuous Liquid—Liquid Extraction. Con-
`tinuous Solid—Liquid Extraction. Multiple~contact Pseudocounter—
`current Extraction. Countercurrent Extraction.
`
`191
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`Chapter 5. The Reaction
`APPARATUS..................191
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`Flasks. Condensers. Stirrers and Stirring Motors. Addition of
`Liquids. Addition of Solids. Addition of Gases. Heating and
`Cooling Baths. Water Separators. Apparatus for Conducting Re—
`actions at High Dilution. Reactions Efiected in an Inert Atmos—
`phere. Semimicro Scale Preparations. Thermostats. Hydrogena-
`tion Apparatus. Ultraviolet Light Sources.
`PURIFICATION or SOLVENTS.
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`240
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`Chapter 6. Literature of Synthetic Organic Chemistry .
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`253
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`index
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`Liquidia - Exhibit 1010 - Page 5
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`Liquidia - Exhibit 1010 - Page 5
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`

`

`Loboraiory Technique in Organic Chemistry
`1.12
`ing homogeneity, particularly of natural products. If the material is
`fractionally crystallized, giving perhaps 8 to 10 fractions from the
`head fraction to the tail fraction (8 to 10 layers), and if these fractions
`are compared and found to be identical, it is reasonable to assume that
`the material is homogeneous.
`The alembic shown in Fig. 2—21 is particularly useful in fractional
`crystallization, since it permits convenient adjustment of the amount
`of solvent and prevents loss of solvent during the prolonged refluxing
`sometimes required to bring the material into solution.
`
`Precipitation
`
`In some cases, the most convenient method for the purification of a
`solid consists in precipitating it from a solution in which it is con—
`tained as a derivative. A typical example is the purification of a water—
`insoluble solid carboxylic acid by dissolving it in sodium hydroxide
`solution, filtering, and precipitating the compound by the addition of
`acid. A similar procedure may be used with amines: dissolve the com—
`pound in acid and precipitate it with a base. These procedures usually
`work quite well in that they utilize a chemical reaction to aid in sep—
`aration from nonacidic or nonbasic impurities.
`Another method of precipitation involves precipitating\-. the com—
`pound as *a derivative and then converting the derivative back to the
`original compound. An example of this is to dissolve an amine in ether,
`precipitate it as the hydrochloride by passing in hydrogen chloride,
`and convert the hydrochloride back to the amine with sodium hydrox~
`ide solution. Again,
`this method is useful because it involves separa—
`tion through the use of a reaction.
`_
`,
`One method of precipitation which is usually relatively unsuccessful
`involves dissolving the compound in one solvent and precipitating by
`the addition of another solvent in which it is insoluble. This procedure
`usually leads to coprecipitation and relatively little purification. If two
`solvents are to be used, the compound should be recrystallized from
`amixture of-the two solvents as described in the preceding section.
`
`Distillation
`
`If the compound is relatively impure, crystallization usually entails
`considerable loss of material, and several recrystallizations are re
`quired to effect complete purification. The procedure often may be
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`Liquidia - Exhibit 1010 - Page 6
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`Liquidia - Exhibit 1010 - Page 6
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