Simple and Fractional Distillation Recrystallization is used as a purifying technique for solids.

The technique most commonly used for purifying liquids is distillation. The method of distillation allows separation of distillates from less volatile substances. In short, distillation is a process of vaporizing a liquid, condensing the vapor, and collecting the condensed vapor. When the vapor pressure of a liquid equals the external pressure, the liquid boils or vaporizes. mixture will boil when the sum of the partial pressures equals the external pressure. When the vapor is cooled and condensed, and collected in the receiving flas!, the condensate will contain more of the more volatile components. t the same time, what is left behind, will contain more of the less volatile material. s the distillation proceeds, the temperature reading of the thermometer in the distillation head will rise gradually. The more volatile substance evaporates and finally will reach boiling temperature of the liquid. The temperature then remains constant as the distillate condenses. It may rise soon after the more volatile substance has distilled if a less volatile substance is left in the original mixture. "e careful to never distill to dryness #explosion danger$. In other words, stop and remove heat source when there is still a little liquid #%.& m'$ left in distillation flas!. This process allows the complete separation of two liquids only if the condensate is repeatedly redistilled. This series of redistillations can be done (automatically) in a fractionating column. The column is pac!ed with some material on which heat exchange between ascending vapor and descending liquid can ta!e place. large surface area is desirable, but the pac!ing cannot be so dense that pressure changes ta!e place within the column causing non*equilibrium conditions. lso, if the column pac!ing has a very large surface area, it will absorb #hold up$ much of the material being distilled. This may result in the column being (plugged) with a condensate layer in the middle of the column. common device for heating round*bottom flas!s is a heating mantle. +and is added to the heating mantle to provide a bath in which the flas! will be situated. The sand is there to increase the surface area of the flas! being heated. dding or removing sand with a micro spatula near and around the flas! can regulate the heat. ,ever heat an empty flas! in a heating mantle. -or most distillations we perform in our labs, set the transformer setting to about .% to &%.

There are several forms of distillation/ simple, fractional, steam, and vacuum distillation. We will use both simple and fractional distillation in this lab. +imple 0istillation/

"e sure to cool the receiving flas! in an ice bath to prevent loss of the distillate. -ractional distillation is the process of heating up a mixture containing different substances with different boiling points, and drawing the different fractions off as they each boil and liquefy at its own level. 1omponents with a higher boiling point condense on the column and return to the solution2 components with a lower boiling point pass through the column and are collected in the receiving flas!. typical application of factional distillation is the production of gasoline from crude oil using fractional distillation. The petroleum ether solvent in our solvent boxes is obtained by collecting the fraction that distills at a certain temperature interval in the fractional distillation of petroleum. That is why the bottles will say 3et. 4ther .%5*6%5 1 or some other temperature range. The most important variable contributing to a good fractional distillation is the rate at which the distillation is carried out. series of simple distillations ta!es place within a fractionating column, and it is important that complete equilibrium be attained between the ascending vapor and the descending liquid #adiabatic$. This process is not instantaneous. lways distil at a rate no faster than two drops per minute. 7icroscale pparatus 8 fractional distillation

+imple and -ractional 0istillation of an cyclohexane9toluene mixture cyclohexane and toluene mixture is a better*behaved mixture than water* ethanol since an azeotropic mixture is not formed. In theory, a mixture of cyclohexane and toluene can be separated with careful fractional distillation. This complete separation is impossible with one simple distillation2 however, with a series of redistillations #fractional distillation$ it is possible. We will chec! the separation with refractive index analysis. . +imple 0istillation of a 1yclohexane*Toluene 7ixture. To a :*m' long*nec!ed round*bottomed flas! is added ;.% m' of cyclohexane, ;.% m' of toluene, and a boiling chip. This flas! is <oined by means of a connector to a distilling head fitted with a thermometer using a rubber connector. The thermometer bulb should be completely below the side arm of the 1laisen head so that the mercury reaches the same temperature as the vapor that distills. The end of the distilling head dips well down into a vial, which rests on the bottom of a .%*m' bea!er filled with ice water. The distillation is started by piling up hot sand to heat the flas!. s soon as boiling starts, the vapors can be seen to rise up the nec! of the flas!. d<ust the rate of heating by piling up or scraping away sand from the flas! so that it ta!es several minutes for the vapor to rise to the thermometer. The rate of distillation should be no faster than two drops per minute. Record the temperature versus the number of drops during the entire distillation. If the rate of distillation is as slow as it should be, there will be sufficient time between drops to read and record the temperature. 1ontinue the distillation until about %.& m' remains in the distilling flas!. t the end of the distillation, measure as accurately as

possible, the volume of the distillate and, after it cools, the volume left in the pot2 the difference is the hold up in the column if none has been lost by evaporation. 7a!e an accurate plot of milliliters #drop number$ versus temperature for the distillation = ; ". -ractional 0istillation of a 1yclohexane9Toluene mixture. The =%*cm column is pac!ed with =.: g of copper sponge and connected to the :*m' short*nec!ed flas! using the connector. The column should be vertical , and care should be ta!en to ensure that the bulb of the thermometer does not touch the side of the distillation head. The column, but not the distilling head, will be insulated with glass wool or cotton at the appropriate time to ensure that the process is adiabatic. To the short* nec!ed flas! is added ;.% m' of cyclohexane, ;.% m' of toluene, and a boiling chip. The distillation column is pac!ed with =.: g of copper sponge. The mixture is brought to a boil over a hot sand bath. >bserve the ring of condensate that should rise slowly through the column2 if you cannot at first see this ring, locate it by touching the column with the fingers. Reduce the heat by scraping sand away from the flas!, and wrap the column, but not the distilling head, with glass wool or cotton if it is not already insulated. gain, apply heat, and as soon as the vapor reaches the thermometer bulb, reduce the heat by scraping away the sand. 0istill the mixture at a rate no faster than two drops per minute. To chec! the efficiency of your separation, collect the first three drops in a separate vial for refractive index analysis. 1ontinue to distill and record the temperature as a function of the number of drops. If the heat input has been very carefully ad<usted, the distillation will cease and the temperature will drop after the cyclohexane has distilled. Increase the heat input by piling up the sand around the flas! in order to cause the toluene to distil. Try to collect the last few drops of distillate in a separate container before ending the distillation. +top the distillation when only about %.& m' remains. +ave a few drops of the pot residue for Refractive Index analysis and measure the total volume of the distillate and pot residue as before. 7a!e a plot of boiling point versus milliliters of distillate #drops$. nalyze the initial drops, the rest of the distllate, the final drops, and the pot residue via Refractive Index. 0o a Refractive Index analysis of your three fractions and pot redue by ta!ing a refractive index of these samples. Then ta!e a refractive index of pure cyclohexane and of pure toluene. ?se the two values for pure toluene and cyclohexane to ma!e a calibration curve. 3lot refractive index vs @ composition #from %@toluene9=%%@ cyclohexane to =%%@ toluene9%@cyclohexane$. ll of your fractions should fall somewhere on your calibration curve. nalysis of the 0ata 1ollected In this experiment, you are going to compare the effectiveness of simple and fractional distillation by plotting temperature of distillate vs. volume of distillate for both methods. 3lot the data of the two types of distillation on one A x ==.: graph. "e sure to use graph paper.

1ompare and explain the temperature versus drops of the simple and fractional distillation. ?sing the Refractive Index results from your fractional distillation, did you achieve complete separation of cyclohexane and tolueneB If not, how is complete separation possibleB 1ompare and explain the total volume amounts of the distillate and pot residue measured at the end of each distillation. 1alculate the holdup of the column for each distillation. re the results you obtained consistent with what they should have beenB Why or why notB 1ompare and explain the ease and accuracy of the two distillation processes. 4xplain under what circumstances simple or fractional distillation should be used. Include the two graphs your lab Write*up.
Reading: http://www.chem.umd.edu/organiclabs/Chem232/Expt06.htm #picture of apparatus$ http://science.howstuffwor s.com/oil!refining".htm http://www.chemhelper.com/distillation.html http://www.chemguide.co.u /ph#sical/phasee$ia/idealfract.html #recommended for phase

diagram explanation$
http://www.poshusta.chem.wsu.edu/%Chem&'/phase&diagram.htm

#how to read phse

diagram$
http://www.philipla(en.com/p20.html #refractive index$ http://resources.schoolscience.co.u /Exxon)obil/infoban /"/2index.htm*distilling.html http://home.clara.net/rod.bea(on/raoult.htm #how phase diagram generated$ http://www.uwlax.edu/facult#/ oster/+istillation30,.htm www.chem.wwu.edu/lampman/Chem-203,"-20lecture-20".ppt #ta!es a while to load

top

page, but good stuff 8 ignore gas chromatography stuff$

http/99www.chem.ufl.edu9Cbarbaro9;;=='9nutmeg9distillation.html http/99www*<csu.<esus.cam.ac.u!9Crpc;:9notes9chemistry9phaseDequillibria9 http/99chemistry.about.com9cs9distillation=9

Eandling 'iquids -or handling liquids refer to http/99www.chemistry.mcmaster.ca9Cchem;o69labmanual9microscale9ms*liq.html Fou will find more information on distillation and reflux at the following sites/ http/99orgchem.colorado.edu9courses9..;=manual90istillation'7+u%;.pdf http/99www.chem.ufl.edu9Cbarbaro9;;=='9experiments.html http/99www.wsu.edu9Cp!uzmic9chem;&%9lab9tlc.htmlGintro