Super-strong solid acid catalytic synthesis method of diaminodiaryl methane compounds
A technology of diaminodiarylmethane and diaminodiphenylmethane, which is applied in the field of super strong solid acid catalyzed synthesis of diaminodiarylmethane compounds, can solve the problems of poor high temperature resistance and deactivation, and achieve The effect of no degradation, excellent high temperature resistance, and excellent recycling performance
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Embodiment 1
[0043] (1) At room temperature, add 0.05 mol (4.65 g) of aniline into a 50 mL flask with a stirrer, slowly add 0.005 mol (0.405 g) of 37% formaldehyde aqueous solution under vigorous stirring, and increase the temperature to 60 after the addition is complete. The reaction was stirred at ℃ for 2h. After the condensation reaction is completed, use a rotary evaporator to remove water and formaldehyde.
[0044] (2) The product obtained in step (1) is further heated to 130°C, N 2 Reflux under protection, add 1g Nafion-HNR50 solid acid catalyst to it, and rearrange the reaction for 6h under stirring.
[0045] (3) The reaction product of step (2) and the solid acid catalyst are separated by filtration, the reactant adsorbed on the catalyst surface is washed with an organic solvent, the catalyst is vacuum dried, and the recovered catalyst is reused.
[0046] Carry out the reaction product of step (3) 1 H NMR analysis (see figure 1 ), of which 2,4'-diaminodiphenylmethane accounts for 27% of ...
Embodiment 2
[0048] (1) At room temperature, add 0.05mol (5.36g) o-toluidine into a 50mL flask with a stirrer, slowly add 0.005mol (0.405g) 37% formaldehyde aqueous solution under vigorous stirring, and then heat up after the addition is complete The reaction was stirred at 60°C for 2h. After the condensation reaction is completed, use a rotary evaporator to remove water and formaldehyde.
[0049] (2) The product obtained in step (1) is further heated to 110°C, N 2 Reflux under protection, add 1g of Nafion-HNR50 solid acid catalyst to it, and rearrange the reaction for 6h under stirring.
[0050] (3) The reaction product of step (2) is separated from the solid acid catalyst by filtration, the reactant adsorbed on the catalyst surface is washed with an organic solvent, the catalyst is vacuum dried, and the recovered catalyst is reused.
[0051] Carry out the reaction product of step (3) 1 H NMR analysis (see figure 2 ), of which 3,3'-dimethyl-2,4'-diaminodiphenylmethane accounts for 7% of the to...
Embodiment 3
[0053] (1) At room temperature, add 0.1mol (12.75g) o-chloroaniline into a 50mL flask with a stirrer, slowly add 0.01mol (0.811g) 37% formaldehyde aqueous solution under vigorous stirring, and then heat up after the addition is complete The reaction was stirred at 60°C for 2h. After the condensation reaction is completed, use a rotary evaporator to remove water and formaldehyde.
[0054] (2) The product obtained in step (1) is further heated to 130°C, N 2 Reflux under protection, add 2g Nafion-HNR50 solid acid catalyst to it, and rearrange the reaction for 6h under stirring.
[0055] (3) The reaction product of step (2) is separated from the solid acid catalyst by filtration, the reactant adsorbed on the catalyst surface is washed with an organic solvent, the catalyst is vacuum dried, and the recovered catalyst is reused.
[0056] Carry out the reaction product of step (3) 1 H NMR analysis (see image 3 ), of which 3,3'-dichloro-2,4'-diaminodiphenylmethane accounts for 12% of the t...
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