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Organic Chemistry LD Synthesis and Purification of Organic Chemistry Compounds Column Chromatography As a Purification Process Leaflets C2.4.4.1

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Organic Chemistry LD Synthesis and Purification of Organic Chemistry Compounds Column Chromatography As a Purification Process Leaflets C2.4.4.1 Organic Chemistry LD Synthesis and purification of organic Chemistry compounds Column chromatography as a purification process Leaflets C2.4.4.1 Separation of a leaf extract by column chromatography Aims of the experiment To produce a leaf extract. To demonstrate column chromatography as a method for separating substances according to their adsorption properties. To understand the separation principle of column chromatography using silica gel as the stationary phase. To explain the order of elution of various leaf pigments based on their molecular structure. To understand the structural associations between various classes of leaf pigments. Principles sorbed (they adhere to it) or desorbed (they return to the solution). Substances with a high affinity to the stationary Column chromatography is a frequently used method for phase spend on average a longer period of time in the ad- separating mixtures of substances in the laboratory. The sorbed state and less time in the solution. Therefore they substances are isolated based on their adhesion properties. It pass more slowly through the column than substances with a functions according to the same principle as other chromato- lower affinity to the stationary phase. graphic methods, but in contrast to these, it is used less for With column chromatography, the stationary phase is located identification and more for the separation and purification of in a cylindrical tube with a discharge tap on the underside. substances. The mobile phase trickles through the stationary phase by The substances to be separated are transported on a mobile gravitational force or is pumped through the stationary phase phase (solvent mixture) through a stationary phase (in this using compressed air (Flash chromatography). The various case silica gel). While the substances to be separated are eluates are collected in separate vessels. These can then be passing over the stationary phase, they are continually ab- investigated for their exact composition, e.g. by thin-layer 08 - 2014 - FS Fig. 1: Set-up of the experiment. Left: Production of the leaf extract. Right: Column chromatography. 1 C2.4.4.1 LD Chemistry Leaflets chromatography, or used for preparative purposes. A further development of column chromatography is HPLC Acetone (high performance liquid chromatography). Here, the sub- stances to be separated are pumped under high pressure Hazard statements through the stationary phase together with the solvent mix- H225: Highly flammable liquid and ture. A detector is located at the end of the column which vapour. detects the impacting substance. H319: Causes serious eye irritation. In the experiment described here, the stationary phase used H336: May cause drowsiness or diz- is polar silica gel and the mobile phase a solvent mixture ziness. consisting of slightly polar acetone (20 % by vol.) and non- polar petroleum ether (80 % by vol.). Silica gel is a polymer EUH066: Repeated exposure may consisting of units of silicic acid (see Fig. 2). These produce a cause skin dryness or cracking. network through condensation. As the condensation is not Signal word: Precautionary statements complete, randomly distributed hydroxyl groups arise. Hazard Because of its porous structure, silica gel is amply permeable P210: Keep away from heat/sparks/ to non-polar solvents. On the other hand, substances with open flames/hot surfaces. No smok- polar groups adhere to the hydroxyl groups or interact with ing. the bridging oxygen and are thus retained. P233: Keep container tightly closed. P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing. Petroleum ether, boiling point range: 90°C - 110°C Hazard statements H225: Highly flammable liquid and vapour. H304: May be fatal if swallowed and enters airways. H315: Causes skin irritation. H336: May cause drowsiness or diz- ziness. H411: Toxic to aquatic life with long- Fig. 2: Formation of silica gel by polymerisation. lasting effects. Precautionary statements Risk assessment P101: If medical advice is needed, The solvent mixture used is a highly volatile and combustible have product container or label at substance that is harmful to health. For this reason, all stages hand. of work in the experiment, including the production of the P102: Keep out of reach of children solvent mixture, must always be conducted in the fume cup- board. The apparatus must be kept away from fires. Signal word: P103: Read label before use A laboratory coat, protective glasses and gloves should be Hazard P210: Keep away from heat. No worn. smoking. P260: Do not breathe vapour/aerosol. P262: Do not get in eyes, on skin, or on clothing. P243: Take precautionary measures against static discharge. P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomit- ing. P403+P233: Store in a well ventilated place. Keep container tightly closed. 2 C2.4.4.1 LD Chemistry Leaflets Equipment and chemicals Preparation of the column chromatography For producing the leaf extract Note: Before performing the experiment, grease the taps and 1 Beaker, DURAN, 100 mL, nF ........................... 664 101 check them for liquid flow. 1 Porcelain mortar, 70 mm diam. ......................... 667 092 Produce the solvent mixture consisting of 20 % by vol. of 1 Pestle 100 mm long .......................................... 667 091 acetone and 80 % by vol. of petroleum ether by mixing 50 mL 1 Funnel, Boro 3.3, 100 mm diam........................ 665 005 of acetone with 200 mL of petroleum ether in a laboratory 1 Round filter Type 595, 150 mm diam., 100 pcs 661 038 bottle with a screw cap. It is necessary to use a bottle with a 1 Narrow-neck bottle, amber glass, 100 mL ........ 661161 screw cap, as if left to stand in the air for a longer period, the 1 Warning notice according to GHS..................... 661 0771 composition of the solvent mixture can change in the case of 1 Filtration stand for 2 funnels ............................. 666 584 highly volatile substances. 1 Sea sand, purified, 1 kg .................................... 674 8210 Cover the base of the chromatography column with some 1 Acetone, 1 l ....................................................... 670 0410 glass wool (press it down with a glass rod). Attach the column Additionally required: to the stand using a universal clamp. Place the large beaker dried or fresh leaves/grasses beneath it. Weigh 15 g of silica gel into a 100 mL beaker. Pour a little solvent mixture onto the silica gel and stir well Column chromatography with a glass rod until a gel-like mass results. Then fill the 1 Chromatography column 235 x 20 mm diam. ... 665 592 column with this mass using a powder funnel. This will require 1 Dropper funnel, glass, 75 mL, SB 29, graduated 665 073 a little solvent mixture to be added occasionally so that the 1 Beaker, DURAN, 100 mL, squat ....................... 664 101 silica gel sludge enters the column completely. Collect any 1 Beaker, Boro 3.3, 600 mL, tall .......................... 602 012 residual liquid in the column in a beaker. Fill the column up to 1 Laboratory bottle to DIN, 500 mL, GL 45 ......... 602 347 about 3 cm below the rim. 1 Warning labels according to GHS ..................... 661 0771 1 Measuring cylinder 100 mL, plastic base .......... 665 754 1 Measuring cylinder 500 mL, plastic base .......... 665 756 Performing the experiment 1 Compact balance 200 g : 0.01 g ....................... 667 7977 Attach the dropper funnel above the chromatography column. 1 Glass stirring rod, 500 / 8 mm diam., 10pcs ..... 665 217 Allow solvent mixture to run out of the column until the liquid 1 Powder funnel, PP, 100 mm diam. ................... 665 025 level reaches the upper edge of the gel. Now place a small 1 Test tube rack, plastic, 18 mm diam. ................ 667 050 amount of leaf extract onto the column using a dropping pi- 10 Glass test tube, Fiolax, 16x160 mm, set of 10 . 664 043 pette. One to two millimetres of liquid above the column is 9 Rubber stopper, solid, 14...18 mm diam. .......... 667 253 sufficient. Open the tap and wait until the column has com- 1 Spoon-ended spatula, PP, 180 mm .................. 666 966 pletely absorbed the leaf extract. 1 Dropping pipette, 150 x 7 mm, set of 10 ........... 665 953 1 Rubber bulbs, set of 10 ..................................... 665 954 The addition of solvent mixture can now commence. Fill the 1 Stand base, V-shaped, small ............................ 300 02 dropper funnel with solvent mixture. Adjust the two taps such 1 Stand rod 47 cm, 12 mm diam. ......................... 300 42 that the drop frequency is approximately equal for both. 2 Bosshead S ...................................................... 301 09 Should the column run dry, add a little more solvent mixture 2 Universal clamp 0...80 mm ............................... 666 555 to the dropper funnel. Take care to note when the eluates of 1 Petroleum ether, 90...110 °C, 250 mL .............. 670 8200 various colours reach the lower edge of the column so that 1 Glass wool, 10 g ............................................... 672 1000 they can be collected in test tubes. 1 Acetone, 1 L ..................................................... 670 0410 Note: Optionally, the eluates collected can be investigated for 1 Silica gel 35-70 mesh, 500 g ............................ 661 058 purity by thin-layer chromatography using the same solvent 1 Stopcock grease, 60 g ...................................... 661 0821 mixture. Set-up and preparation of the experiment Observation Producing the leaf extract Bands of different colours can be identified in the column. The bands are orange, yellow, green and blue-green. 1. Rub the dried leaves or grasses between your fingers. Place sufficient crushed plant material into the mortar to fill it Result of the experiment about one third. Leaf pigments enable photosynthesis to take place in plants. 2. Add some sea sand and sufficient acetone (2-propanone) They belong to the light-collecting complexes in the thylakoid to fully saturate everything with extraction medium. membranes of the chloroplasts. The centre of these com- 3.
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