Chem 232 Liquid Liquid Extraction of P-Bromoanaline
Essay by mictrentz • February 24, 2016 • Lab Report • 1,001 Words (5 Pages) • 1,655 Views
Chemistry 232 Fall 2015 and Spring 2016
Separation by Chemical Extraction
Abstract
p-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 Regeneration
Procedure Reference
Appendix, pages A-2 (Melting Point), A-14 (Rotary Evaporator), A-14 (Recrystallization), A-19 (Extraction), A-24 (Column and Thin-Layer Chromatography)
Liquid-liquid Extraction
Reagents for Extraction
Compound | MW (g/mol) | Used | moles | Physical and Safety Data |
p-Bromoanaline | 172.03 | 1.00 g | 5.81 x 10-3 mols | Irritant in case of skin/eye contact, hazardous in case of ingestion/inhalations. MP= 66 C; BP= decomposes |
Hydrochloric Acid (HCl) | 36.46 | 3 x 30 mL | 0.396 mols | Highly toxic, corrosive (3M solutions). Dispose as aqueous waste. Density= 1.20 g/M |
Phenantherene* | 178.23 | 2.00 g | 1.12 x 10-2 mols | Toxic, hazard to aqueous environment. MP= 98-100 C; BP= 340 C; density= 1.063 g/M |
Dichloromethane (DCM) | 84.93 | 100 mL | 1.56 mols | Toxic, dispose in halogen waste. BP= 39 C, d= 1.3255 g/mL |
Anhydrous Sodium Sulfate | 142.04 | 6.209 g | 4.37 x 10-2 mols | Irritant, hydroscopic. MP= 884 C, d=2.68 g/mL |
Sodium Hydroxide | 40.00 | 30 mL | 1.59 mols | Toxic, corrosive; 3 M. Dispose in basic aqueous d= 2.13 g/mL |
*Phenanthrene remained in the organic layer
Recrystallization of Phenanthrene
Compound | MW (g/mol) | Used | moles | Physical and Safety Data |
Phenanthrene | 178.23 | 1.0 g | 0.0056 mols | Toxic, hazardous to aqueous environment. Harmful if swallowed MP= 99-101 C, BP= 346 C, d= 1.063 g/mL |
Ethanol | 46.07 | 20 mL | 0.340 mols | Flammable liquid, irritant. Dispose as non-halogenated waste. BP= 78 C, d= 0.790 g/mL. |
Water | 18.02 | 0.271 g | 1.50 x 10-2 mols | Can be hazardous depending on contents. MP= 0C, BP= 100 C; d= 1.00 g/mL |
All Products; Crude and Recrystallized
Compound | MW (g/mol) | Isolated | moles | % recovery |
Crude phenanthrene | 178.20 | 1.059 g | 5.94 x 10-3 mols | 53% |
Recrystallized Phenanthrene | 178.23 | 1.101 g | 6.18 x 10-3 mols | 110% |
Aqueous precipitate (p-bromoanaline salt) | 172.03 | 0.271 g | 1.57 x 10-3 mols | 28% |
Physical Description
Crude 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 % recovery
Yield Calculation for Recrystallization of Phenanthrene
% yield = 0.006178451 mol / 0.0056 mol x 100%
= 110 % recovery
Melting Range Data
Sample Determined | Observed Melting Range | Lit. Melting Range | Identification |
Component from solution A | 55°C | 60-64°C | p-Bromoanaline |
Component from solution B | 90 -93°C | 111-113°C | m-Toluic Acid |
Crude phenanthrene | 77-87°C | 98-101°C | --- |
Recrystallized phenanthrene | 74-85°C | 98-101°C | --- |
The sample for the melting range of the m-Toluic Acid was supplied by Maddy Wrazej.
Solubility Data
Solubility | ||||||||
Compound | Ethanol | Hexanes | Toluene | Water | ||||
cold | hot | cold | hot | cold | hot | cold | Hot | |
Anthranilic acid | s | V | i | 𝛿 | i | V | 𝛿 | s |
Phenanthrene | 𝛿 | s | s | V | V | V | i | i |
m-Toluic acid | 𝛿 | V | s | V | V | V | i | i |
p-Bromoaniline | 𝛿 | s | 𝛿 | V | s | V | i | 𝛿 |
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