Preparation method of hindered amine quaternary ammonium salt
A technology of quaternary ammonium salts and hindered amines, which is applied in the field of redox active materials for flow batteries, can solve the problems of few synthesis reports and achieve the effects of low cost, simple operation steps and high product purity
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Embodiment 1
[0043] 1) Synthesis of 4-chloro-2,2,6,6-tetramethylpiperidine (III):
[0044] Dissolve 157g of 4-hydroxy-2,2,6,6-tetramethylpiperidine in 500g of toluene, drop the temperature by 5°C, and then add 76.5g of phosphorus oxychloride dropwise to the reaction solution. Control the temperature not to exceed 10°C; then slowly raise the temperature to 110°C, keep the temperature for 2 hours, lower to 30°C, add 200g of water and stir vigorously for 1 hour, then adjust the pH value to 10, extract with dichloromethane, dry over anhydrous magnesium sulfate, and rotate After evaporation of the solvent, 172 g of a colorless liquid with a GC content of 98%, namely 4-chloro-2,2,6,6-tetramethylpiperidine, was obtained, which was used directly in the next stage.
[0045] 1 H NMR (400MHz, D 2 O) δ = 4.35(m, 1H), 2.17(d, 2H), 1.79(br, 1H), 1.42(t, 2H), 1.24(s, 6H), 1.19(s, 6H).
[0046]
[0047] 2) Synthesis of N,N,N,2,2,6,6-heptamethylpiperidinium-4-ammonium chloride (IV):
[0048]Put 172g...
Embodiment 2
[0056] 1) Synthesis of 4-chloro-2,2,6,6-tetramethylpiperidine (III):
[0057] Dissolve 1000g of 4-hydroxy-2,2,6,6-tetramethylpiperidine in 3000g of toluene, drop the temperature to 5°C, and then add 682g of phosphorus oxychloride dropwise to the reaction solution. Control the temperature in the medium to not exceed 10°C; then slowly increase the temperature to 105°C, keep the temperature for 2 hours, cool down to 30°C, add 2000g of water and stir vigorously for 1 hour, adjust the pH value to about 10, extract with dichloromethane, and dry with anhydrous magnesium sulfate. After rotary evaporation of the solvent, 1076 g of a yellow liquid with a GC content of 97%, namely 4-chloro-2,2,6,6-tetramethylpiperidine, was obtained, which was directly used in the next stage.
[0058] 2) Synthesis of N,N,N,2,2,6,6-heptamethylpiperidinium-4-ammonium chloride (I):
[0059] Put 1076g of 4-chloro-2,2,6,6-tetramethylpiperidine obtained in the previous stage into the autoclave, add 1500g of a...
Embodiment 3
[0063] 1) Synthesis of 4-chloro-2,2,6,6-tetramethylpiperidine (III):
[0064] Dissolve 800g of 4-hydroxy-2,2,6,6-tetramethylpiperidine in 1200g of toluene, and after lowering the temperature to 5°C, add 540g of phosphorus oxychloride dropwise to the reaction solution. Control the temperature in the medium to not exceed 10°C; then slowly raise the temperature to 100°C, keep the temperature for 2 hours, cool down to 30°C, add 600g of water and stir vigorously for 1 hour, adjust the pH value to about 10, extract with dichloromethane, and dry with anhydrous magnesium sulfate. After rotary evaporation of the solvent, 861 g of a yellow liquid with a GC content of 97%, namely 4-chloro-2,2,6,6-tetramethylpiperidine, was obtained, which was directly used in the next stage.
[0065] 2) Synthesis of N,N,N,2,2,6,6-heptamethylpiperidinium-4-ammonium chloride (I):
[0066] Put 861g of 4-chloro-2,2,6,6-tetramethylpiperidine obtained in the previous stage into the autoclave, add 1200g of ace...
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