Weeks 4 & 5 Indigo Synthesis

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1 Weeks 4 & 5 Indigo Synthesis I believe that the great Creator has put ores and oil on this earth to give us a breathing spell. As we exhaust them, we must be prepared to fall back on our farms, which is God s true storehouse and can never be exhausted. We can learn to synthesize material for every human need from things that grow. George Washington Carver Scientist An understanding of the transformation of matter is fundamental to the study of chemistry. The synthesis of new molecules and new materials is the basis of the chemical industry. The synthesis of new chemicals involves a number of different linked processes. First, reactions are performed that generate new chemicals. Then the products are isolated from the other materials present, purified and characterized. This last procedure involves measurement of their chemical and physical properties to confirm their identity and purity. This two-week experiment is designed to introduce you to some of the issues involved in transforming matter. You will investigate the synthesis of the dye indigo. This common dye will be made, isolated and evaluated. Educational Objectives: A student who has successfully completed this experiment will be able to synthesize indigo, determine percent yield for a reaction, make leuco-indigo from indigo, dye cloth using vat dying, perform a sulfonation reaction, and use absorption spectroscopy to determine yield. Experimental Objectives: A student who performs this experiment is asked to synthesize indigo from smaller precursors, isolate the indigo using filtration and determine a yield, prepare leucoindigo and use it to dye a cloth test strip, synthesize indigo carmine from indigo, and quantify the indigo carmine produced using absorption spectroscopy. Background Indigo is the name given to an organic molecule with an intense blue color and to the plant (a member of the pea family) from which it is extracted. Indigo has been used to dye cotton and wool fabric for millennia. It is the source of the color in blue jeans. The molecule was first made synthetically in By the turn of the 20 th century a commercial process had been developed and synthetic production quickly replaced agricultural production. Synthesizing Indigo Many different ways are now known to make indigo. The one presented here is quick and produces indigo in very high yield. The reaction is between 2 nitrobenzaldehyde (a.k.a. o-nitrobenzaldehyde or orthonitrobenzaldehyde) and acetone in the presence of a strong base (NaOH). 2 C 7 H 5 NO C 3 H 6 O C 16 H 10 N 2 O CH 3 CO 2 H + 2 H 2 O (2-1) 2-nitrobenzaldehyde acetone indigo acetic acid

2 The organic molecules are dissolved in water. A NaOH solution is added to start the reaction. Since indigo is virtually insoluble in water, it precipitates as fast as it forms. The product can be readily collected by filtration and quantified. Dying Cloth Indigo s insolubility in water not only makes it easily to isolate, but also makes it a good dye. Once impregnated in the cloth, washing with water will not easily dislodge the dye molecules. Getting the dye into the cloth, however, is a problem. Fortunately, the chemistry of indigo provides a solution. Indigo can be reduced to form a compound known as leucoindigo. Equation 2 shows half of the reaction for this reduction. It can be coupled with any suitable reaction that provides the two electrons. C 16 H 10 N 2 O H + + 2e C 16 H 12 N 2 O 2 (2-2) indigo leucoindigo Leucoindigo is a colorless molecule that is quite soluble in water. To dye cloth, indigo is reduced to leucoindigo with an appropriate reagent and dissolved in water. The cloth to be dyed is then dipped into the solution. When the cloth is removed from the solution and allowed to dry, the oxygen in the air will oxidize the leucoindigo to indigo. Simultaneously, the dye becomes fixed in the cloth and the color appears. A suitable reaction to provide the needed electrons is the oxidation of the stannite ion to stannate. This is the reaction that will be available for you to use. SnO 2 2- stannite ion H 2 O SnO H + + 2e (2-3) stannate ion Making Indigo Carmine Although indigo itself is quite insoluble in water, it can be reacted with sulfuric acid to produce watersoluble forms that retain the characteristic intense blue color. When placed in a concentrated solution of sulfuric acid, the indigo will add two, three or four sulfonic acid (HSO 3 ) units. The actual number will depend on the strength of the acid, the temperature and the reaction time. C 16 H 10 N 2 O H 2 SO 4 2 C 16 H 8 N 2 O 8 S 2 Indigo sulfuric acid indigo disulfonic acid C 16 H 10 N 2 O H 2 SO 4 3 C 16 H 7 N 2 O 11 S 3 indigo trisulfonic acid + 2 H 2 O + 2 H + (2-4) + 3 H 2 O + 3 H + (2-5) 4 C 16 H 10 N 2 O H2SO4 C 16 H 6 N 2 O 14 S H 2 O + 4 H + (2-6) indigo tetrasulfonic acid The disulfonic acid form is extensively used in industry. As a dye in the food and drug industry, it is known as FD&C Blue #2. It is also used as a functional kidney test and to color nylon surgical sutures. One gram of indigo carmine will dissolve in about 100 ml of water.

3 The Problem The problem put to your group is to investigate the properties of the organic dye indigo. The process you will use can be summarized as follows. 1. Make some indigo. 2. Isolate the indigo and determine a yield. 3. Convert some of the indigo into leucoindigo and use that to dye a cloth sample. 4. Convert the remaining indigo into indigo carmine and determine the yield using absorption spectroscopy. The first three activities will be performed the first week. Your charge is to determine the efficiency of this synthesis method in preparing indigo. Indigo carmine will be synthesized the second week. But indigo carmine is only one of three possible products. In fact, the extent of the reaction and the mixture of products will be affected by the conditions under which the reaction is performed. Your group is asked to evaluate the effect of one of the following conditions on the extent of reaction and the mixture of products: strength of the acid, the temperature and the reaction time. Procedures Making Indigo The quantities given here are intentionally small. Larger quantities of the indigo can be made by proportionately increasing the amounts. You will need to write procedures in your lab notebook based on the descriptions given here. Parts of these procedures will be used as answers to the TA-graded pre-lab questions. Don t worry about having correct procedures. You will have the chance to modify them based on what you learn during the pre-lab discussion. Here s a short video of indigo being made. Indigo is a highly colored dye. Very small amounts can impart lots of color to all kinds of things (clothing, hands, books, etc.). Be careful to avoid coloring things best left uncolored. Write a procedure for making indigo. Incorporate the following features. Use approximately 0.4 g of 2-nitrobenzaldehyde. This is a solid reagent. Use about 5 ml of acetone. This is a liquid reagent. Dissolve the nitrobenzaldehyde in the acetone and then add the NaOH. You should use about 6 ml of 1.0M NaOH. You will need to add the NaOH slowly the reaction generates a lot of heat. Don t add the NaOH so fast that the acetone evaporates. After thoroughly mixing these chemicals you will need to allow the mixture to sit for at least 5 minutes to ensure the reaction is complete. Isolate the indigo using vacuum filtration as described in chapter 5-2 of the lab book. Allow the indigo to dry. When it s dry you can determine the mass. Characterizing Indigo: Dyeing Cloth

4 Indigo is used to dye cloth in a process known as vat dyeing. The indigo is first converted to the watersoluble leucoindigo (2-2). The cloth is then dipped into a solution of the leucoindigo, allowed to soak, removed, and allowed to dry. As the cloth dries, oxygen from the air oxidizes the leucoindigo back to indigo, and in the process, also fixes the indigo in the cloth. Preparation of leucoindigo is a two-step process. First, the reductant must be made, then the leucoindigo prepared. The reductant provided for your use is the sodium stannite reagent. Because it is a strong reductant, it easily reacts with atmospheric oxygen. Thus, it must be prepared fresh every time it is used. Here s how. Sodium Stannite Reagent Put one gram of stannous chloride dihydrate in a small beaker (150 ml). Add 10 ml of 1 M HCl and swirl to dissolve. This should take a few minutes. Don t worry if the solution is cloudy. Add 20 ml of 3 M NaOH. Swirl to mix. At first a white to off-white precipitate will form. It should re-dissolve with mixing. Again, this should take a few minutes. Don t worry if the final solution is slightly cloudy. This solution is the stannite reagent. Preparation of Leucoindigo Place half of the indigo you made earlier in a small beaker. Save the other half for next week. Add 3 ml of a 3 M NaOH solution. Heat to boiling in a hot water bath. Slowly add stannite reducing reagent, with constant stirring. The indigo dissolves rather slowly. The stannite reagent should be added a ml or so at a time, with mixing, until a total of 25 ml has been added. Continue to heat and stir for another 10 minutes. Take a clean small beaker (150 ml) and add 25 ml of distilled water. Gravity filter the leucoindigo solution, collecting the filtrate in this beaker. The dilute filtrate is what you will use to dye the cloth. Work a small piece of cloth into the dye solution and allow it to soak. When saturated, remove and allow it to drain and dry. Note that the leucoindigo cannot be reoxidized until the cloth has dried out. Once the cloth is dry, the color will slowly develop. Making Indigo Carmine Performing the Reaction In addition to reacting with concentrated sulfuric acid, indigo is also soluble in this reagent. Thus, the reaction system is rather simple. Solid Remember that concentrated sulfuric acid, like all concentrated acids, is strongly corrosive and will cause the immediate destruction of clothing and skin. Should you suspect you ve gotten some on you, begin washing with water immediately and consult your instructor. Make sure all spills are neutralized and cleaned up immediately. Figure 2-1. Cloth swatch for testing indigo.

5 indigo is dissolved in 18 M H 2 SO 4 and the mixture heated to promote the reaction. After a sufficient period of time, the reaction can be stopped by the addition of water which will also dilute the sulfuric acid and the un-reacted indigo will precipitate out. The following is an outline of a procedure for evaluating this reaction. You should use your remaining indigo for this procedure. It should be at least 0.05 g. If you don t have enough consult your instructor. Dissolve the indigo in concentrated sulfuric acid (H 2 SO 4 ). You should use 20 drops (1 ml) for every 0.1 g of indigo you have with a minimum amount of 1 ml. Swirl to dissolve the indigo in the acid. Heat in a simmering water bath. How long depends on what you and your group decide on but it should be for at least 10 minutes and not longer than 30. When it is time to stop, pour the reaction mixture into distilled water. But first, cool the solution. Use 5 ml of water for every ml of acid you started with. The unreacted indigo will precipiatate leaving the sulfonated products dissolved in the water. Set up a clean vacuum filtrate apparatus. Do not add water to acid. You can get a steam explosion. Pour the acid into water. And do not pour hot acid into water. Again, a potential explosion. Remember that you will be keeping the filtrate. Filter the indigo solution. Use a small amount of distilled water to wash all solution through the funnel. You may discard the solid, un-reacted indigo residue. Determine the volume of your filtrate. A graduated cylinder is sufficient for this measurement. Spectrophotometric Determination of Product Yield You will be evaluating your product using absorption spectroscopy. Since you want to know the total moles you will need to know both the molarity and the total volume. You will need to develop a procedure to determine the λ max and the absorbance. Remember that if the absorbance is more than 1.0 you will need to dilute the solution. Finally, you will need to know the molar absorptivity for all the appropriate indigo sulfonate known solutions. Data Analysis and Report Considerations Data Analysis For the synthesis of indigo you will need to determine your percent yield which is discussed in chapter 2-4 of the lab book. This will require figuring out the experimental yield and the yield theoretical yield which is best done while still in lab in collaboration with your fellow group members. For the synthesis of indigo carmine, determine your percent yield. Again you will need to know the experimental yield and the theoretical yield. And again, this is best done while still in the lab in collaboration with your fellow group members. For the synthesis of indigo carmine you will also have to evaluate which of the three sulfonated indigo carmines you made. This will be done by evaluating the spectrum of your product solution.

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