Thanks for the good suggestions. Yes, swim has been leaning more toward CTH, but for completeness is interested in the simplest setup that might be put together a for H2 gas hydrogenation. A big advantage of CTH is the ease with which TLC tests can be made to monitor the reduction. The disadvantage is that CTH has less supporting refs for the type of reactions that swim is interested in - mostly ring reduction of hetrocycles and non aromatics and the difficulty of procuring a hydrogen donor. In any case this may all be for nothing since swims catalyst source has fallen through.
Ammonium formate is out of reach (Leuckart) unless preped from materials available otc. hypophosphite is not available although phosphinic acid and salts are.
Regarding ammonium formate, - this is apparantly a better hydrogen donor than either formic acid or NaCOOH. I am aware of Rhodium's synth of formic acid from oxalic acid and glycerol however I am thinking that H202 oxidation of formaldehyde might be a better option. This is supposedly much easier than trying to oxidise methanol all the way to formic acid.
I am wondering if the reaction in italics proposed below might be adapted to go straight to Nh4COOH by substituting NaOH with NH4OH to create the alkaline conditions.
2HCHO + 2 NH4OH + H2O2 ----> 2HCOONH4 + 2 H2O + H2The formed volatiles would just be evaporated off leaving behind ammonium formate - followed by a recrystalisation?. Remembering that for swim's purposes yield is not important although purity is what byproducts might be formed that could not be just boiled off. The imine base of formaldehye and ammonia? Otherwise using NaOH as the base would require distilling the formic acid out of H2SO4 followed by titration with aqueous ammonia.
Alkaline Reaction
2HCHO + 2 NaOH + H2O2 ----> 2HCOONa + 2 H2O + H2
HCHO will be oxidized to formate / formic acid. The reaction will take 10 - 180 minutes depending on reaction temperature, pH, and H2O2 charge. With moderate temperatures (< 40 deg C) and a pH of 10 - 11, the H2O2 demand should be about 0.8 parts H2O2 per part HCHO, which translates into an H2O2 cost of about $0.75 USD per lb-HCHO. It is possible to reduce the H2O2 demand by increasing the NaOH charge (to 2 - 3 g/L) and elevating the temperature (to 60 - 80 deg C) to affect aldol condensation. In this case, the H2O2 demand should be about 0.3 parts H2O2 per part HCHO, which translates into an H2O2 cost of about $0.30 USD per lb-HCHO. However, these savings are partially offset by the higher NaOH charge (about $0.25 USD per lb - HCHO). source:
http://www.h2o2.com/applications/industrialwastewater/hcho.html