Separation of Ferrocene and Acetylferrocene by Chromatography
Purpose
1. To prepare a dry-packed sample of product mixture of ferrocene and Acetylferrocene
2. To separate and purify the components in the product mixture by column chromatography.
3. To check the purity of the components by thin-layer chromatography (TLC).
4. To calculate the yield of acetylferrocene and the percent recovery of unreacted ferrocene.
Table of Quantity showing various physical properties
Type of substance Molecular Formula Molecular Weight (g/mol) Density(g/cm3) M.P.(oC) B.P.(oC) Solubility
Ferrocene C10H10Fe 186.03 1.49 172 oC-174 oC 249oC Insoluble in water, soluble in organic solvent
Acetyl-ferrocene C12H12FeO 228.08 - 81 oC -83 oC 161 oC - 163 oC (at 4 mm) Very slightly soluble in water, soluble in organic solvent
Ethyl Acetate C4H8O2 88.11 0.897 -83.6 oC 77.1 oC Slightly soluble in water (~8.3g/100mL, 20 oC), very miscible with alcohol, ether, acetone, benzene.
Hexane C6H14 86.18 0.6548 -95 oC 69oC Immiscible with water
Dichloro-methane CH2Cl2 84.93 -97 oC 40 oC 1.325 Slightly soluble in water (~1.3g/100mL, 20 oC), very miscible with most organic solvent.
Hazard
1. Ferrocene is highly flammable and it is harmful if swallowed.
2. Acetylferrocene is highly toxic if swallowed.
3. Ethyl acetate is irritant and flammable.
4. Dichloromethane is a suspected carcinogen.
Procedure
1. The mass of the product mixture was measured.
2. About 2mL of CH2Cl2 was added to the product mixture in a 30mL beaker and about 300mg of silica gel was added
3. The beaker was covered with aluminum foil with a hole and was CH2Cl2 was evaporated.
4. 2.3g of fresh silica gel was mixed with 7mL of hexane in a 30mL beaker to get a slurry.
5. Stirred the slurry constantly with hexane added and poured it into the column.
6. Hexane was added and run until the solvent was about 1cm above the silica gel.
7. About 1cm of sand was added followed by loading of the dried sample.
8. Hexane was added and run until the first fraction was collected
1. To prepare a dry-packed sample of product mixture of ferrocene and Acetylferrocene
2. To separate and purify the components in the product mixture by column chromatography.
3. To check the purity of the components by thin-layer chromatography (TLC).
4. To calculate the yield of acetylferrocene and the percent recovery of unreacted ferrocene.
Table of Quantity showing various physical properties
Type of substance Molecular Formula Molecular Weight (g/mol) Density(g/cm3) M.P.(oC) B.P.(oC) Solubility
Ferrocene C10H10Fe 186.03 1.49 172 oC-174 oC 249oC Insoluble in water, soluble in organic solvent
Acetyl-ferrocene C12H12FeO 228.08 - 81 oC -83 oC 161 oC - 163 oC (at 4 mm) Very slightly soluble in water, soluble in organic solvent
Ethyl Acetate C4H8O2 88.11 0.897 -83.6 oC 77.1 oC Slightly soluble in water (~8.3g/100mL, 20 oC), very miscible with alcohol, ether, acetone, benzene.
Hexane C6H14 86.18 0.6548 -95 oC 69oC Immiscible with water
Dichloro-methane CH2Cl2 84.93 -97 oC 40 oC 1.325 Slightly soluble in water (~1.3g/100mL, 20 oC), very miscible with most organic solvent.
Hazard
1. Ferrocene is highly flammable and it is harmful if swallowed.
2. Acetylferrocene is highly toxic if swallowed.
3. Ethyl acetate is irritant and flammable.
4. Dichloromethane is a suspected carcinogen.
Procedure
1. The mass of the product mixture was measured.
2. About 2mL of CH2Cl2 was added to the product mixture in a 30mL beaker and about 300mg of silica gel was added
3. The beaker was covered with aluminum foil with a hole and was CH2Cl2 was evaporated.
4. 2.3g of fresh silica gel was mixed with 7mL of hexane in a 30mL beaker to get a slurry.
5. Stirred the slurry constantly with hexane added and poured it into the column.
6. Hexane was added and run until the solvent was about 1cm above the silica gel.
7. About 1cm of sand was added followed by loading of the dried sample.
8. Hexane was added and run until the first fraction was collected
References: 1) Safety (MSDS) data (http://physchem.ox.ac.uk/MSDS/) 2) Sigma-Aldrich catalogue (http://www.sigmaaldrich.com) 3) Williamson, Macroscale and Microscale Organic Experiments, 4th Edition, 2003, P.156-162, 171-173 4) Solomons and Fryhle, Organic Chemistry, 8th edition, 2004, P.1058-1059