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SC CHEM 333 - Synthesis of Phthalic acid Pre-Lab

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Works CitedOrganic Chemistry 333L, section 03M LaboratoryPre-LabSynthesis ofPhthalic acidSynthesized By:Cameron KahnInstructor (TA): James Collie13 January 20191 | P a g eObject:In this experiment, a person will be able to purify phthalic acid by means of recrystallization, andrecover a pure stable compound with a minimum loss of product. They will also be able to findthe melting point, mass of the product, and calculate the percent recovered.Theory:The most important method for purification of a solid organic compound is crystallization. Mostcommercial samples are only 95 – 96% pure and need to be purified using recrystallization. It isa rapid and convenient method[ CITATION Geo12 \l 1033 ]. The recrystallization processpurifies alum, aspirin, and copper sulfate. One of the most important parts of the recrystallization process is choosing the right solvent forthe job. The solvent should allow impure organic solid to dissolve completely when heated.When the solution cooled to room temperature or below, the solid should recrystallize fromsolution in a pure form. The solid then should be isolated in a pure form while the impurities inthe solid fail to dissolve at the elevated temperature or remain dissolved when the solutions iscooled.Separating crystals from the solvent done by means of gravity filtration. Gravity Filtration is atechnique used to separate a solid from a liquid. The solid separated from the liquid phase bypassing the mixture over a filtering media. The mixture forced through the filter by eithergravity or reduced pressure on one side of the filter (by creating a vacuum). It is possible toseparate a solid from a liquid by either technique; however, there are advantages to eachtechnique[ CITATION Boa13 \l 1033 ].Procedure:Start by measure 100mg of impure phthalic acid and placing it in a small test tube. Now add 1-1.5 mL of room temperature water and a boiling stone. Bring the solution to a boil by using theheating mantle with a Variac setting of 50. Be sure to place the test tube in a holder, pointingaway from people while heating the solution. When the solution begins to boil, wait to see if allsolids dissolve. If any solids remain, add a few drops of water. Be careful not to add to muchwater as to maintain a saturated solution. Check to make sure, if there any insoluble impuritiesin your solution, as they will need to be removed by means of a hot gravity filtration. With thesolids dissolved and the insoluble removed, allow the hot solution of phthalic acid to stand atroom temperature for 5 – 10 minutes. Now to complete the recrystallization by cooling the phthalic acid solutions test tube in an icebath. Crystals should start to form. If crystals are not forming, scratch the inside of the test tubewith a glass-stirring rod to start the process. Once crystals start to form, collect the product bymeans of the Buchner suctions funnel process. When the product collect in the Buchner funnelwash the product free of a soluble impurities with a few drops of ice-cold water. Do-not use hotwater or room temperature water to wash the product, because you will lose some of yourproduct. Leave your product in the Buchner funnel to drain for a few minutes as to remove as2 | P a g emuch of the solvent as possible. Spread out the solid product on filter paper and let dry. Next,record the mass of the dried product and calculatepercent recovered, melting point, and percent difference and record your finding in your labbook.Apparatus:Equipment Needed:I. Small Test Tube (Figure 1)II. Suctions Filtration Apparatus (Figure2)III. Test Tube Holder (Figure 5)IV. Test Tube Rack (Figure 1)V. Scoopula (Figure 4)VI. Heating Mantle (Figure 3)Attach the three-finger clamp to a ring stand. Next, you will need to secure theneck of the filter flask with the clamp. Secure the filter flask adapter on theopen end of the Buchner funnel containing the pre-weighed filter paper. Connect the tube to thefilter flask and the aspiration. Set the water to a high flow rate to create suction. Check forsuction by pushing down lightly on the top of the Buchner funnel with the open palm of yourhand. You should feel a small pull on the palm of your hand, if not check all connections.Always dismantle by disconnecting the vacuum tube first, then removing the filter and adapterflask. Rinse the flask with acetone and drain in to liquid organic waste container, then rinse withwater and dry. Rinse test tube and Buchner funnel with acetone and drain into liquid organicwaste container, then rinse with water and dry. Discard the soiled filter paper in the solid organicwaste container and set apparatus to dry[ CITATION Geo12 \l 1033 ].3 | P a g eFigure 2: Buchner Funnel ApparatusFigure 1: Test tube/rackFigure 3: Heating MantleFigure 5: HolderFigure 4: ScoopulaFigure 1: test tube and rackChemical Table:Name Structure Atomic Weight Melting Point Boiling Point DensityPhthalicacidC6H4(CO2H)2166.14 g/mol 191-230˚C 207°C 1.59 g/cm³Disposal:Use the solid organic waste container to dispose of all phthalic acid and filter paper. Make sureto flush filtrate down the drain with tap water. Soiled gloves and paper towels need to bedisposed of in their proper containers. Any broken glass needs placed in the broken glasscontainer. Consult the TA if unsure about any disposal procedure.4 | P a g eWorks CitedAli, George Handy and Salman. Chemistry 333 & 334 Laboratory Manual. Columbia South Carolina: QDE Press, 2012.System, Board of Regents of the University of Wisconsin. Chem Pages Laboratory Resources. 261 2013. 26 1 2013 <http://chem.wisc.edu/deptfiles/genchem/lab/labdocs/modules/gravfilt/gravfiltdesc.htm>.5 | P a g eOrganic Chemistry 333L, section 001 LaboratoryPost-LabSynthesis ofPhthalic acidSynthesized by Christopher N. Rufty13 January 20196 | P a g eSynthesized for Organic Lab - Dr. Handy, and Fiona OxshuResults:Phthalic acid is a white crystal. While doing the experiment there were no visible signs ofimpurities. The recrystallized crystals looked long clear, shards like white stained glass. A watch glass used to collect the phthalic acid with a dry mass of 37.256g. The initial mass ofthe phthalic acid used at the start of the experiment was 0.104g. The pure product collected andthe mass of the watch glass 37.356g. A difference of 0.100g pure phthalic acid refined. A melting point of 215


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