Sodium+Borohydride+Reduction+of+Vanillin

Hailey Baldwin Sodium Borohydride Reduction of Vanillin

Vanillin is naturally found in the seedpods of the vanilla plant and has a sweet smell. Synthetic formation of Vanillin is produced using lignin, a byproduct of wood pulp. Vanilla flavoring and odors are very popular. The synthetic formation of Vanillin is much more affordable then the harvesting of nature vanilla plants.



Vanillin can be synthetically transformed into Vanillyl alcohol. This process is done through the reduction of Vanillin. Green chemistry is exploring this synthesis for several reasons. First, as the by-product of wood vanillin is a renewable material. Lignin is highly available to aid in the production for vanillin, thus the synthesis to Vanillyl alcohol is renewable and shows great potential for the formation of active molecules and a flavoring ingredient. Second, the reaction uses benign solvents, reactants and products. In the past Lithium aluminum hydride (LiAlH4) was used as the reducing agent, it is highly reactive and produces hydrogen gas. Replacing LiAlH4 with a benign reducing agent such as sodium borohydride yields a much safer and stable experiment. Third the amount of solvent is reduced. The solvent is the reaction is ethanol.



(Vanillyl Alcohol)

Vanillin + NaBH4 (sodium borohydride) + 4H2O (water) -Vanillyl alcohol + H3BO3 (boroic acid) + NaOH (sodium hydroxide)

The key chemical concept involves nucleophilic addition to the carbonyl group. This group is then reduced by the reducing agent which is NaBH4. In addition water is also used as a reagents and aids in oxidation.


 * **Name of reactant** || **MW** || **mass or volume added** ||
 * Vanillin || 152.15g || 2.5-2.6g ||
 * NaBH4 || 37.83g || 5.0mL ||
 * Ethanol || 46.07 || 5.0mL ||
 * Ice Water || 18.07 || 1 mL ||
 * HCl || 36.46g || drops until pH below 7 ||

** Theoretical Mass yield = ** 1 mol of vanillyl alcohol 154.16 + 1 mol boronic acid 61.83 + 1 mol sodium hydroxide ** Atom economy ** =MW of desired product / MW of all reactants Vanillyl alcohol 154.16g/mol + (boronic acid) H3BO3 61.83 + Sodium Hydroxide 40.00 / Vanillin 152.15g/mol + NaBH4 37.83g/mol + 4 H2O 72.28g/mol = .976 x 100 = 98% ** Effective Mass Yield %= ** mass of products x 100 / mass of non-benign reagents density of NaBH4 = 5.350 g/mL x 5mL of NaBH4 = 26.73g

how do I know how many mols or grams I will have of my product? to calculate effective mass yield?

__** Equipment needed for this experiment **__ 50mL beaker 25 mL round beaker flask solid addition funnel stand and clamps ice bath vaccum filtration equipment melting point equipment IR spectrometer


 * Hazards and Safety**
 * Compounds || NFPA-Health || NFPA-Fire || NFPA-Reactive || Hazardous || Sigma-Aldrich # || Part in the reaction ||
 * Vanillin || 2 || 1 || 0 || Harmful if inhaled, causes respiratory tract and skin irritation || 120804 || reactant ||
 * Sodium borohydride || 3 || 0 || 2 || Harmful if inhaled destructive mucous membrane, skin and eye burns, toxic if swallowed || S9125 || Reducing agent ||
 * Ethanol || 2 || 3 || 0 || Skin and eye irritation, harmful in inhaled or swallowed || P5833 || Rinse ||
 * Hydrochloric acid || 3 || 0 || 1 || Burns and irritating to the respiratory tract || 320331 || used for acidification ||
 * **Disposal Regulations**

Observe all federal, state, and local environmental regulations.Contact a licensed professional waste disposal service to dispose of this material. || Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. || Burn in a chemical incinerator equipped with an afterburner and scrubber but exertextra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material || Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material || Thanks for doing a thorough job and getting it done on time.
 * Vanillin: **
 * ** Sodium borohydride: **
 * ** Ethanol: **
 * ** Hydrochloric acid: **