The goal of the second part of the experiment was to separate the fluorene and fluorenone mixture by the method of column chromatography. Separate a mixture of fluorene and 9 fluorenone by column chromatography. Is it just because hexane is nonpolar and fluorene is less polar than. Evaporate an aqueous slurry of 1 g of potassium permanganate and 10 g of. Most of the condensable substances fluorene, 9fluorenone, phthalic anhydride, 2,3indenedicarboxylic anhydride and maleic anhydride were separated on an ov1 capillary column for gc analysis. Part 7 of 7 of the ivc chemistry lab safety series. Unit 9, column chromatography including the following. Post lab thinlayer chromatography fluorenone, fluorenol, and fluorene from highest to lowest r 2. The percent recovery of fluorene was found to be 38. Column chromatography was performed on silica gel 60120 mesh to purify the compounds. Is there anything about their structure which would.
Column chromatography was used in this part of the experiment as a separation technique since it permits the sample to be collected whereas tlc only allows the product to be separated and not collected. Weigh the mixture of fluorene and fluorenone isolated in week 1. The progress of the oxidation will be monitored by thin layer chromatography, tlc, using fluorescent silica gel sheets 2. Column chromatography uses the same principles as tlc to separate compounds, but can be used on a larger scale. The fluorenone scaffold is present in a number of natural and synthetic bioactive compounds with important pharmacological activities, including anticancer, antihiv1, and antioxidant.
Nov 21, 20 1 explain why fluorene travels faster through the column than fluorenone when using hexane as the elution solvent. The fluorene is more soluble in that solvent than the fluorenone, but would be likely to oxidise to fluorenone when you try to dry it off. The 9fluorenone will be oxidized with naocl to form the ketone, 9fluorenone. The purpose of this experiment was to utilize the technique of column chromatography in order to separate various compounds from each other. It can be synthesised from fluorene with the addition of glacial acetic acid and sodium hypochlorite solution, undergoing an oxidation reaction.
The structure of all the synthesized compounds was confirmed by standard physiochemical techniques. A solution processablefluorenefluorenone oligomer with. Fluorenone was detected in particles from brake linings and road dust at concentrations of 0. Fluorene and flourenone lab report robbysean cayetano chem. Students use semiquantitative tlc and product recoveries from column chromatography to determine which procedure provides the better yield of fluorenone. The ketone in fluorenone can be easily reduced to an alcohol by the action of sodium borohydride. Reduction of fluorenone with nabh4 in my lab, we reacted 9fluorenone with sodium borohydride in ethanol. Column chromatography will be used to separate fluorene from an oxiation product 9 fluorenone one of htese compounds is white and the other is yelloiww the progress of hte chromatography may be followed by evaporation of the solvent at periodic intervals as well as by observing teh slowermoving yellow band. Fluorene and fluorenone have very different polarities that we will take advantage of when we separate the components of a fluorene fluorenone mixture. Suppose your were visualizing a tlc plate and all of the spots were at the solvent front. It can be synthesised from fluorene with the addition of glacial acetic acid and.
An improved process for the production of pure fluorenone by oxidation of fluorene with air or oxygen at ambient temperature in the presence of a quaternary salt, the improvement comprising carrying out the reaction in a suspension of fluorene or a fluorenecontaining fraction in an aprotic immiscible with water solvent, such as a. Minard, bellamarie bregar and other students from spring 01 honors organic chemistry rev 9203 introduction. Fluorenone based fluorescent probe for selective turnon. Wear appropriate protective eyeglasses or chemical safety goggles as described by oshas eye and face protection regulations in 29 cfr 1910. In the separation of fluorene and fluorenone during column chromatography, what is the stationary phase and what is the mobile phase. Is there anything about their structure which would correlate with this ordering by ry.
Column chromatography of fluorene and fluorenone free essays. The reason why this separation was feasible was due to the fact that these two compounds do not have the. Liquid column chromatography was used in this experiment to separate. Orgo lab 6 column chromatography abstract the purpose of. John davison at irvine valley college, in irvine, ca. Jun 15, 2018 column chromatography was performed on silica gel 60120 mesh to purify the compounds. This particular experiment was performed in order to isolate the compounds flourene and 9fluorenone from each other.
Sodium borohydride nabh 4 is a common reducing agent that reduces ketones to alcohols. Fluorenene to fluoronone essay sample new york essays. Most of the condensable substances fluorene, 9 fluorenone, phthalic anhydride, 2,3indenedicarboxylic anhydride and maleic anhydride were separated on an ov1 capillary column for gc analysis sichromat 2, siemens, fid. The next step is to spot your filtrate and authentic samples of fluorene and fluorenone sidebyside on a tlc plate and elute the plate with an available solvent you think should separate them. The 9 fluorenone will be oxidized with naocl to form the ketone, 9 fluorenone. Column chromatography was used in this part of the. Recent advances of synthesis of fluorenone and fluorene. A simple experiment to demonstrate nucleophilic addition to a carbonyl. It will depend on the nature of the stationary phase the substance that you put in the column to s. Is it just because hexane is nonpolar and fluorene is less polar than fluorenone. These results illustrate that the fluorene and fluorenone were properly separated in the column chromatography and the order in which they appear on the tlc plate is also evident of this. In the reaction using koh, the smallsized base, the major product. Students isolate their fluorenol product by recrystallization and characterize it by nmr and ir.
Us4218400a process for the production of fluorenone by. The progress of the reduction will be monitored by thin layer chromatography, tlc, using fluorescent silica gel sheets 2. Because fluorene moves faster through the column than the fluorenone, it makes sense that it will show up in the earlier test tubes because it is eluted first. Developing investigation skills in an introductory multistep. Air oxidation of fluorene to fluorenone separation of products by column chromatography chem 2 experiment 6 synthesize the fluorenefluoreneone. Fluorenone was present in 2 of 3 samples of spent chlorination liquor from the bleaching of sulphite pulp at concentrations of 0. After the reaction was complete as determine by tlc. Separate a mixture of fluorene and 9fluorenone by column chromatography. In particular, by using tlc initially to determine a solvent system for separation of a mixture, one can quickly find the solvent system that will effect separation of the same mixture on a column of the same adsorbent. One reagent lane fair lawn, nj 07410 for information in north america, call. The next step is to spot your filtrate and authentic samples of fluorene and fluorenone sidebyside on a tlc plate and elute the plate with an available. Fluorenone is an aromatic organic compound with the chemical formula c h 8 o. The same comments that were made concerning adsorbents and solvents for tlc apply also to column chromatography.
Column chromatography was invented by tswett in 1906 so that his study of the chemistry of. An improved process for the production of pure fluorenone by oxidation of fluorene with air or oxygen at ambient temperature in the presence of a quaternary salt, the improvement comprising carrying out. Fluorene and fluorenone have very different polarities that we will take advantage of when we separate the components of a fluorenefluorenone mixture. Fluorene is a polycyclic aromatic hydrocarbon that contains three ring systems. Chromatographic separation of fluorene and fluorenone abstract. Thin layer chromatography is a very rapid technique, so if. Your crude sample should be dissolved in less than one ml of dichloromethane just before it is applied to the column. Fluorene is an apolar molecule, while fluorenone which i believe is the second molecule you are referring to is polar, due to the carbonyl group. It is bright fluorescent yellow in color and is a solid at room temperature. Liquid column chromatography was used in this experiment to separate fluorene and fluorenone from a mixture.
Dissolve the crude mixture of fluorene and fluorenone in a. After all, the stationary phase, silica, is quite polar and the order of polarity of the three compounds as stated correctly in the experiment is. After visualizing your thinlayer chromatography results, no doubt you established the elution order of the three compounds as. Nov 12, 2009 chromatographic separation of fluorene and fluorenone abstract. A solution processablefluorenefluorenone oligomer with aggregation induced emission enhancement. Infrared spectroscopy will be used to determine the identity of each product. The retention factors were calculated to find the distances the samples of the compounds being tested moved up the plate relative to the distances moved by the solvent front. Column chromatography of the fluorenefluorenone mixture prepare a microscale chromatographic column exactly as described at. The progress of the oxidation will be monitored by thin layer chromatography, tlc, using. In place of the standard tlc and column chromatography labs, you will do a 4step synthesis of difluorenylidene. Column chromatography of the fluorene fluorenone mixture prepare a microscale chromatographic column exactly as described at the beginning of this chapter see fig. Column chromatography will be used to separate fluorene from an oxiation product 9fluorenone one of htese compounds is white and the other is yelloiww the progress of hte. Process for the production of fluorenone by catalytic. This process requires special catalysts as well as the traditional measure of melting the fluorene.
In principle, the chemical compound that flows through the column at a faster speed is more nonpolar. Soundaram jeevarathinam ananthakrishnan, a belumalai varathan, ezhakudiyan ravindran, a. Fluorene will elute off of your very polar alumina column first before fluorenone when using hexane as the eluting solvent. Chromatographic seperation of fluorene and fluorenone essay. I do have the chemical structures of each of these. Fluorenone was detected in particles from brake linings. Fluorene and flourenone lab report robbysean cayetano. A mixture of fluorene 1 and fluorenone 2 was separated by column chromatography. Organic chemistry lab manual harper college, fall 2010 o 9fluorenone mp 8285oc och 2ch 3 o h 2n ethyl 4aminobenzoate mp 9192oc oh o benzoic acid mp 122oc procedure acidbase. The structure of all the synthesized compounds was confirmed by standard.1625 178 454 1103 182 12 825 1590 989 1441 1295 140 568 50 685 175 959 881 1185 1615 661 369 1413 167 1615 787 209 699 1328 242 8 1613 871 1086 1350 741 290 503 778 692 290 1233 1192 894