Chem 232 Liquid Liquid Extraction of P-Bromoanaline
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Chemistry 232 Fall 2015 and Spring 2016Separation by Chemical ExtractionAbstractp-Bromoanaline was isolated via liquid-liquid extraction. Phenanthrene was separated and purified via recrystallization. The purity of the phenanthrene sample was determined using the thin layer chromatography method and via the comparison of melting ranges. The % recovery of the crystal phenanthrene was determined to be 110%, and p-bromoanaline was 28 %.Equation of Extraction and RegenerationProcedure ReferenceAppendix, pages A-2 (Melting Point), A-14 (Rotary Evaporator), A-14 (Recrystallization), A-19 (Extraction), A-24 (Column and Thin-Layer Chromatography)Liquid-liquid ExtractionReagents for ExtractionCompoundMW (g/mol)UsedmolesPhysical and Safety Datap-Bromoanaline172.031.00 g5.81 x 10-3 molsIrritant in case of skin/eye contact, hazardous in case of ingestion/inhalations. MP= 66 C; BP= decomposesHydrochloric Acid (HCl)36.463 x 30 mL0.396 molsHighly toxic, corrosive (3M solutions). Dispose as aqueous waste.Density= 1.20 g/MPhenantherene*178.232.00 g1.12 x 10-2 molsToxic, hazard to aqueous environment.MP= 98-100 C; BP= 340 C; density= 1.063 g/MDichloromethane(DCM)84.93100 mL1.56 molsToxic, dispose in halogen waste.BP= 39 C, d= 1.3255 g/mLAnhydrous Sodium Sulfate142.046.209 g4.37 x 10-2 molsIrritant, hydroscopic.MP= 884 C, d=2.68 g/mLSodium Hydroxide40.0030 mL1.59 molsToxic, corrosive; 3 M. Dispose in basic aqueous d= 2.13 g/mL*Phenanthrene remained in the organic layerRecrystallization of PhenanthreneCompoundMW (g/mol)UsedmolesPhysical and Safety DataPhenanthrene178.231.0 g0.0056 molsToxic, hazardous to aqueous environment. Harmful if swallowedMP= 99-101 C, BP= 346 C, d= 1.063 g/mLEthanol46.0720 mL0.340 molsFlammable liquid, irritant. Dispose as non-halogenated waste. BP= 78 C, d= 0.790 g/mL.Water18.020.271 g1.50 x 10-2 molsCan be hazardous depending on contents. MP= 0C, BP= 100 C; d= 1.00 g/mL
All Products; Crude and RecrystallizedCompoundMW (g/mol)Isolatedmoles% recoveryCrude phenanthrene178.201.059 g5.94 x 10-3 mols53%Recrystallized Phenanthrene178.231.101 g6.18 x 10-3 mols110%Aqueous precipitate (p-bromoanaline salt)172.030.271 g1.57 x 10-3 mols28%Physical DescriptionCrude phenanthrene- thick/dense consistency, off-white, powdered solid.Aqueous precipitate (p-bromoanaline salt)- whitish colour. Crystalized once cooled. Sweetish odour.Crystallized phenanthrene- original state was thick/dense off-white powdered solid, when hot water added became hard, shiny/sparkly crystals.Yield Calculation for p-Bromoanaline % yield = moles of product / moles of start material x 100% = 0.001575306 mol / 0.0056 mol = 28 % recoveryYield Calculation for Recrystallization of Phenanthrene% yield = 0.006178451 mol / 0.0056 mol x 100% = 110 % recoveryMelting Range DataSample DeterminedObserved Melting RangeLit. Melting RangeIdentificationComponent from solution A55°C60-64°Cp-BromoanalineComponent from solution B90 -93°C111-113°Cm-Toluic AcidCrude phenanthrene77-87°C98-101°C—Recrystallized phenanthrene74-85°C98-101°C—The sample for the melting range of the m-Toluic Acid was supplied by Maddy Wrazej.Solubility DataSolubilityCompoundEthanolHexanesTolueneWatercoldhotcoldhotcoldhotcoldHotAnthranilic acidsVi𝛿iV𝛿sPhenanthrene𝛿ssVVViim-Toluic acid𝛿VsVVViip-Bromoaniline𝛿s𝛿VsVi𝛿