tags
trichloroacetic aciddiethylzincestersTrichloroacetichydrogendichloroaceticchloridesulfuric acidchloroaceticethertrichloroaceticzinc salt

video tutorial Reduction of trichloroacetic acid using zinc

  • Goal: reduce trichloroacetic acid (TCA) with zinc; initial undiluted setup caused rapid moisture absorption and dense vapors, so a dilute aqueous approach with ice was used.
  • Reagents and conditions: 25 g TCA dissolved in ~50 mL water with ice; 11 g ground zinc powder (~1.1:1 molar ratio) added slowly under stirring; reaction is exothermic and yields zinc-organic salts rather than hydrogen gas.
  • Observation: zinc participates in reduction; formation of zinc salts, not free hydrogen; after addition and stirring, the mixture warms; further scraping suggests adsorption of hydrogen may occur; reaction yields a hot mixture requiring cooling.
  • Workup: pH tested; sulfuric acid (10 mL of 50%) added to regenerate free organic acids; extraction with 40 mL diethyl ether, separation of organic phase, drying with MgSO4, and solvent evaporation to isolate product.
  • Product recovered: 13.5 g of pale yellow, slightly oily liquid; chilled tests and crystallization attempts did not yield pure TCA; possible mixture of trichloroacetic acid (unreacted), dichloroacetic acid (DCA), and possibly monochloroacetic acid (MCA); presence of HCl vapor on cooling suggested chlorinated acids were present, but conclusive identification of DCA was not achieved.
  • Characterization notes: the product’s aroma suggested possible esters (trace ethanol from ether); crystallization is difficult, complicating purification; lack of burette prevents accurate titration for definitive composition.
  • Two days later: freezing at −15°C showed slight viscosity but liquid remained; test of reactivity with zinc showed DCA is less reactive than TCA, yet the reaction was still rapid/exothermic, supporting a mixture of acids rather than pure DCA.
  • Conclusion: the product is likely a mixture of unreacted TCA, DCA, and possibly MCA; crystallization is challenging, and tests are inconclusive for pure DCA; product is highly skin-damaging, so handling requires extreme caution.
  • Note: further testing and purification are needed; the presenters invite input on suitable tests.

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