Synthesis of Disperse Red 9
By: June A. Fitzloff
Benzene
Synthesis derived from https://www.youtube.com/watch?v=X10VZeQmFDo
Materials:Chemicals
Materials:Supplies
Synthesis of Benzene
Grind 100g of Sodium Benzoate to a fine powder and transfer to a beaker. Repeat but this time with 65g of Sodium Hydroxide. Mix the powders together with a metal spatula and pour the powder into the paint can. Put the lid on the can and attach the distillation apparatus to the can with the camp stove as the heat source. Run the apparatus until benzene stops coming over. Transfer the crude benzene to a separatory funnel and wash with water a few times. You may dry the washed benzene with calcium chloride but this step is optional. Transfer the benzene to a distillation apparatus this time with a round bottom flask in a water bath. Run the apparatus and the fraction with the lower temperature should be the benzene.
1-anthraquinone
Synthesis derived from the Hawthorn synthesis of anthracene
Materials:Chemicals
Materials:Supplies
Synthesis of 1-anthraquinone
Put 90cc of benzene in a medium beaker and add 150g of phthalic acid. Turn on strong stirring and add 5g of AlCl3 and allow to stir overnight. Filter and transfer to a round bottom flask. Bring to a boil and add 15cc. of conc. sulfuric acid for at least 2 hours. Distill of the sulfuric acid until you have a dry powder. To purify, you can dissolve the product in acetic acid, but this is optional.
1-nitroanthraquinone
Nitration proposed by Lionel Spanner on the science madness forum
Materials:Chemicals
Materials:Supplies
Synthesis of 1-nitroanthraquinone
Add 100cc. of conc. sulfuric acid and 100cc. of conc. nitric acid to a beaker. Stir and add 10g of 9-10-anthraquinone to the mixture. Let sit for a few hours. Distill or filter, IDK I haven’t tested this yet.
Boric acid
Synthesis derived from https://www.youtube.com/watch?v=YtVpGXII3l0
Materials:Chemicals
Materials:Supplies
Synthesis of Boric acid
Bring 45cc. of water to a boil in a beaker. Add 15.5 grams of borax to the water and stir until dissolved. Once dissolved remove the solution from heat and add 5cc. of 3 molar HCl. Cover and allow to cool to room temperature. Move to fridge for a few hours to crystalize as much boric acid as possible. Decant remaining liquid and transfer crystals to a coffee filter to dry.
Potassium anthraquinone-α-sulfonate
Synthesis derived from http://www.orgsyn.org/demo.aspx?prep=cv2p0539
Materials:Chemicals
Materials:Supplies
Synthesis of Potassium anthraquinone-α-sulfonate
Set up a three neck flask with a mechanical stirrer in an oil bath. Submerge a thermometer halfway into the bath. In the flask add 120g oleum and 0.31g of boric acid. Warm the bath to 100°C and add 100g anthraquinone. Stir vigorously and heat to 147-152°C for 45-60 minutes after which remove the oil bath and stirrer from the stand. Place a 2-l. beaker containing 1 l. of hot water and a mechanical stirrer. Pour the hot acid solution slowly into the beaker and boil for another 5 minutes. Filter in a 20cm. Büchner funnel with a cotton filter cloth. Wash with 100cc. of water and heat filtrate along with wash water to 90°C. Add a solution of 32g potassium chloride in 250cc. water to the hot filtrate solution. Cool to room temperature. Filter the solution through a large Büchner funnel with filter paper and wash with 200cc. of cool water. Collect the crystals and dry at 100°C in a vacuum.
Materials:Chemicals
Materials:Supplies
Synthesis of sodium chlorate
Bring 100cc. of bleach to a boil until crystals precipitate. Allow to cool to room temperature. Decant of the sodium chlorate solution and discard the salt crystals. Add water equal to half the volume of the left over fluid to a beaker and add potassium chloride until it no longer dissolves into solution. Pour into the sodium chlorate solution and move to a freezer for 12 hours. Filter potassium chlorate solution and collect the crystals. Dissolve crystals into more water and put it back into the freezer for another 12 hours. Filter again and dry.
1-chloroanthraquinone
Synthesis derived from http://www.orgsyn.org/demo.aspx?prep=CV2P0128
Materials:Chemicals
Materials:Supplies
Synthesis of 1-chloroanthraquinone
Set up a 2-l. three neck flask with a condenser and dropping funnel. Place 20g of potassium anthraquinone-α-sulfonate, 500cc. of water, and 85cc. of conc. HCl. Heat to a boil with medium stirring while adding a solution of 20g sodium chlorate in 100cc. of water dropwise over the course of three hours. Reflux for an additional hour and then collect precipitated 1-chloroanthraquinone by vacuum filtration. Wash with about 350cc. of hot water. Dry product at 100°C under vacuum.
1-aminoanthraquinone
Suggested by Lionel Spanner
Materials:Chemicals
Materials:Supplies
Synthes of 1-aminoanthraquinone
Dissolve 25g 1-nitroanthraquinone in 200cc. of ethanol in a beaker. Add 8g of sodium sulphide and let stirr for a few hours. Boil of ethanol and add 100cc. of dist. water. Filter and dry.
Formaldehyde
Materials:Chemicals
Materials:Supplies
Synthesis of Formaldehyde
Add 10g Iron oxide and 100cc. of methanol to the boiling flask and set up for reflux. Heat to about 300°C for a few hours. Filter and distill.
Formic Acid
Materials:Chemicals
Materials:Supplies
Synthesis of Formic Acid
Add 82cc. of formaldehyde to the erlenmeyer flask and turn on medium stirring. Slowly add 70g of sodium hydroxide.
Cannizzaro reaction
Disperse Red 9 (1-methylamino-anthraquinone)
Materials:Chemicals
Materials:Supplies
Disperse Red 9 Synthesis
Try a Eschweiler-Clarke methylation
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