Phosphonic acid, P-(1Z)-1-propen-1-yl-, bis(1,1-dimethylethyl) ester synthesis

Yield:25383-05-5 97%

Reaction Conditions:

with hydrogen in toluene at 15 - 30; under 1140.08 - 1672.11 Torr; for 0.3 - 1.16667 h;

Steps:

1-5 Example 1

Example 1 Add 8 g of a Ni-Al catalyst to a solution containing 112 g of diterbutyl propadienylphosphonate in 1000 ml of toluene. The catalyst contains at least 93% Ni, with a particle size of less than 80 μm. The mixture is inerted, and is heated to 30° C passing H2 through it until a pressure of 2 atm is reached. The reaction ends after 18 minutes. 110 g of diterbutyl cis-1 propenylphosphonate is obtained, which means a yield of 98%. The reaction is monitored using infrared spectroscopy.Example 2 Add 16.5 g of a Ni-Al catalyst to a solution containing 230 g of diterbutyl propadienylphosphonate in 2000 ml of toluene. The catalyst contains at least 93% Ni, and a particle distribution of less than 200 μm. The mixture is inerted, and the temperature is maintained at 22°C passing H2 through it until a pressure of 1.5 atm is reached. The reaction ends after 55 minutes. 226 g of diterbutyl cis-1 propenylphosphonate is obtained, which means a yield of 98%.Example 3 Add 8 g of a Ni-Al catalyst to a solution containing 60 g of diterbutyl propadienylphosphonate in 1000 ml of toluene. The catalyst contains at least 93% Ni and an average particle size of 27 μm. The mixture is inerted, and the temperature is maintained at 15° C passing H2 through it until a pressure of 2.2 atm is reached. The reaction ends after 19 minutes. 58 g of diterbutyl cis-1 propenylphosphonate is obtained, which means a yield of 97%.Example 4 Add 16 g of a Ni-Al catalyst to a solution containing 232 g of diterbutyl propadienylphosphonate in 3000 ml of toluene. The dry catalyst contains at least 93% Ni and an average particle size of 42 μm. The mixture is inerted, and the temperature is maintained at 15° C passing H2 through it until a pressure of 2 atm is reached. The reaction ends after 70 minutes. 225 g of diterbutyl cis-1 propenylphosphonate is obtained, which means a yield of 97%.Example 5 Add 7 g of a Ni-Al catalyst to a solution containing 112 g of diterbutyl propadienylphosphonate in 1000 ml of toluene. The catalyst contains 93% Ni. The mixture is inerted, and is heated to 30° C passing H2 through it until a pressure of 2 atm is reached. The reaction ends after 50 minutes. 110 g of diterbutyl cis-1 propenylphosphonate is obtained, which means a yield of 98%.

References:

EP1422232,2004,A1 Location in patent:Page 3