Synthesis of Saccharic Acid by Oxidation of D-Glucose

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Saccharic acid or D-glucaric acid is a dicarboxylic acid C6H10O8 derived from glucose or its derivatives by oxidation with nitric acid. Saccharic acid formed the salt with d-amphetamine. This salt is a component of Adderall as a long-lasting amphetamine (Study Candy).

The synthesis process proceeds according to Scheme 1
M7sdG82yHa


Starting reagents and materials

  • 30 g D-glucose
  • 80 ml nitric acid ~50%
  • 80 ml distilled water
  • 5+5 ml distilled water for washing crystals
  • Beakers
  • Heater with water bath
  • Porous glass filters
  • Vacuum pump
  • Desiccator with alkali

Synthesis

80 ml of concentrated nitric acid (~50%) is placed in to a beaker. Fig 1
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Fig 1

~50% nitric acid is diluted with water to 160 ml to a concentration of ~25-26% Fig 2
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Fig 2

160 ml of diluted nitric acid is added to 30 g of glucose powder. Fig 3
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Fig 3

The mixture is heated and carefully evaporated on a water bath. Nitrogen oxides are formed! (Toxic brown gas!) Fig 4
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Fig 4

After the formation of nitrogen oxides ceases, RM evaporates to a syrupy consistency. Fig 5
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Fig 5

The syrupy RM is left to crystallize in air or in a desiccator over alkali for several days. Fig 6
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Fig 6

Over time, the RM may acquire a brown color, which is normal. Fig 7
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Fig 7

The crystals are filtered out Fig 8
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Fig 8

The crude crystals are transferred to a small porous filter Fig 9
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Fig 9

With the vacuum on, rinse with water in a volume of no more than 5 ml. The acid is very soluble in all solvents. Fig 10
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Fig 10

The crystals are dried in a desiccator over alkali. Fig 11
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Fig 11

Yield is 2 g
 
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