Comparative studies of the behavior of unsaturated acids and their salts in hydrogenation over platinum

A method for preparing sodium acrylate‐d3, a useful and stable precursor for deuterated acrylic monomers

“…Prior to conducting reactions using deuterium, a series of survey reactions were performed using hydrogen gas to determine the optimum reaction conditions that would maximize the yield of sodium acrylate (3-H) while minimizing the amount of sodium propiolate (2-H) remaining and the amount of sodium propionate (4-H) produced. It was previously reported that treatment of sodium propiolate in 0.1 M NaOH at 40 C with hydrogen over Pt black 6 could produce sodium acrylate; however, synthetic details are absent, and no information regarding the yield of sodium acrylate is provided. On the basis of this work, the partial reduction of sodium propiolate using the Lindlar catalyst (200mg per 1.15g of 2-H) was first investigated in 0.05M NaOH.…”

“…A literature search revealed only one example where sodium acrylate was prepared directly by the partial reduction of sodium propiolate. 6 In that work, the sodium propiolate was reduced over Pt black in 0.10M NaOH solution affording a mixture of sodium acrylate and sodium propionate, although synthetic details were not provided. As we had some experience using the Lindlar catalyst 7,8 (Pd supported on CaCO 3 or BaSO 4 , modified with Pb) to reduce terminal alkynes to alkenes, we first attempted the partial reduction of sodium propiolate with hydrogen and the Lindlar catalyst in various aqueous media, including 0.05M NaOH, but found that essentially no reduction took place, even after stirring overnight.…”