Chemistry 3411 Purification by Recrystallization You will be given a sample of dimethylterephthalate which you will purify by recrystallization.

Recrystallization ma es use of differences in solubility between the desired compound and impurities. !o do this" a solvent must be used in which the desired substance is soluble in boiling solvent but insoluble when cold. #ince there is no such thing as completely insoluble" you will lose some of your desired compound to the cold solvent at the time of your final filtration. $f your solvent is warm" huge amounts may stay dissolved %which is a bad thing& !he more solvent that you use" even if cold" the more product you will lose. !hus you should ideally use the minimum amount of solvent that will dissolve all of your desired compound when hot. $n general" higher purity is achieved by slow crystallization. !he following outline shows the se'uence of events in a recrystallization and the fate of the substance%s& at each step.

mi(ture of desired compound hot solvent insoluble impurities soluble impurities

insoluble insoluble impurities %remove by filtration& soluble cold desired compound soluble impurities solvent insoluble desired compound %collect by filtration& soluble desired compound %trace& soluble impurities

Before you come to lab Read )ubric chapter 11 %the portion on solid products& and chapter 13 on recrystallization. Complete your prelab including properties and safety data for methanol and dimethylterephthalate. * series of short videos are available on the class website http+,,www.aug.edu,-tcrute,lab.techni'ues,lab.techni'ues.htm to assist you in preparing to complete a recrystallization. Procedure Prepare a melting point sample of the impure sample and set it aside for later. Record the mass of the impure sample %it will be about 1 gram& and place it in a /0 m1 2rlenmeyer flas with a small stirbar. #tart adding some room temperature methanol and begin to heat the flas to bring the methanol to a boil. 3eanwhile" set up your gravity filtration e'uipment consisting of the 14/ m1 2rlenmeyer flas on the same hot plate with a large stir bar" a glass funnel above it" and fluted filter paper in the funnel. 5nce a fair amount of methanol %/ or 10 m16& has been added and come to a boil" you should begin the hot filtration process %even if not all of the sample has dissolved&. 7ust before you begin filtering" note how much methanol you have added and how much of the sample dissolved. 8or instance" you may notice that about half of the sample dissolved with / m1 added. !his will serve as a guide later for the 9right: amount of solvent for the cooling stage. $f you have not added enough methanol to fully dissolve all product" it is o ay because later you will be adding more hot methanol that can dissolve the remaining material. !here will li ely be some insoluble impurities that will never dissolve and remain trapped in the filter paper. ;on:t use too much methanol. !oo much solvent will cause problems later. ;uring the filtration the solution will cool down and will see some desired product %dimethylterephthalate& will crystallize in the filter paper and on the glass funnel. *dd more methanol to the original flas " heat to boiling" and filter to try to get as much of the desired material is out of the original flas as possible %though you will not be able to get all of it& <se boiling methanol to rinse product through the filter paper" however don:t use any more methanol than you have to. Chec the amount of total solvent you have" remembering how much methanol you initially added and whether it all dissolved or not. You want a barely saturated solution. !hus if your early observation was that / m1 dissolved about half the sample" then you should shoot for 10 m1 as your final volume now. $f you have too much" evaporate the e(cess by bringing it to a gentle boil %with a stirring bar in there=&. $f you evaporate too much away" impurities will crystallize and contaminate your product. >hen you have %or have achieved& the 9right: amount of solvent it is

time for slow cooling to induce crystallization. Remove the flas from the heat and allow it to cool %and crystallize& as slowly as practical. %Rapid crystallization traps impurities in the crystals.& 5nce your sample has cooled to room temperature" you should see some crystals present. ?ow cool the sample in an ice@water bath %clamp it=&. Cool a portion of fresh methanol as well. $f after a couple minutes of cooling you do not see crystals" contact the instructor for options such as proper use of the stirring rod to assist crystallization. You will collect your crystals by vacuum filtration. 3a e sure the solution is ice@cold and use vacuum filtration with a ABchner funnel to collect your crystals. 3a e sure you pre@wet your filter paper to seal it to the funnel. Rinse the crystals with small portions of cold methanol. 1et air run through the crystals for several minutes to dry them as much as possible. $f time permits" you may wish to isolate a second crop of crystals from the mother li'uor" especially if you are dissatisfied with the amount of crystals from the first crop. Your instructor can guide you if you are unsure how to do this. 5nce the crystals are as dry as possible" record the melting point of the purified product as well as the original impure sample. ;etermine the mass of product recovered and calculate the percent recovery based on the amount you started with. >hen you are completely done with your sample" have the instructor or !* evaluate your crystals" sign off on your noteboo " and instruct you on where to put the crystals. Results #ummarize important observations from the recrystallization including how many crops of product" percent recovery %show calculations&" and the melting point range of product. Discussion Comment on the important practical aspects %e.g. temperature control" volume of solvent& of performing recrystallizations" and advantages and disadvantages of this techni'ue as a purification tool. >hich part%s& of your e(periment led to decreased yield or purity6 >hat did your melting point tell you about the purity before and after the recrystallization. >hen is it necessary to boil off solvent before crystallization6 >hen is it unnecessary to boil off solvent before crystallization6 Cow can you tell you have the right amount of solvent6 >hat properties must your recrystallization solvent possess6 Questions *nswer each of the following 'uestions in a separate section of the report *8!2R the discussion+ >hat are the e(pected conse'uences of the following procedural errors6 %be as specific as possible& 1. Performed final crystallization by transferring flas of boiling solution directly to ice bath %assume that the flas will not brea & 4. !oo much solvent was present during the final cooling" crystallization" and filtering 3. 5mitted the first filtration 4. ;uring final filtering" used warm solvent to rinse crystals