反応 #170952
ord-cd9f2d93171e44769130843b0329e994
反応方程式
反応物
試薬
反応条件
後処理
- 1その他To a 2 L jacket-equipped separable flask
- 2その他provided with a stirrer
- 3その他Prepared gas
- 4workup.ADDITIONdiluted with nitrogen so as
- 5温度While the solution was heated
- 6その他was removed by the Dean-Stark water separator
- 7workup.ADDITIONThus, a reaction solution containing 3-hydroxy-1-adamantyl methacrylate
- 8その他was obtained
- 9その他The obtained reaction solution
- 10洗浄The resultant solution was washed with 5% by weight of dilute sulfuric acid and with 500 ml of ion exchange water
- 11ろ過After the washing, precise filtration
- 12ろ過filter
- 13その他Then, concentration-crystallization
- 14その他was performed by use of an evaporator while the temperature of the solution
- 15その他was kept at 40° C., until the weight of the solution
- 16濃縮After the concentration
- 17温度cooling
- 18その他crystallization
- 19その他was performed at a temperature of an ice water bath
- 20その他to separate the crystal
- 21ろ過by filtration
- 22洗浄The crystal was rinsed with heptane twice
- 23その他dried at a reduced pressure at 35° C. for 24 hours
- 24その他During the process from the dehydration esterification reaction
- 25その他to the solid-liquid separation
- 26洗浄until the termination of rinsing
実験手順
To a 2 L jacket-equipped separable flask provided with a stirrer, a thermometer, a Dean-Stark water separator, a Dimroth condenser and a gas blowing tube, 84.0 g of 1,3-adamantanediol, 124.1 g of methacrylic acid, 0.38 g of p-methoxyphenol as a polymerization inhibitor, 1.2 g of concentrated sulfuric acid as an acid catalyst, and 750 ml of toluene as a solvent were put. Prepared gas diluted with nitrogen so as to have an oxygen concentration of about 5% by volume was supplied at a rate of 0.2 L/min. The reaction operation was performed as follows. While the solution was heated and water generated as a secondary product was removed by the Dean-Stark water separator, the reflux state was continued for 5 hours. Thus, a reaction solution containing 3-hydroxy-1-adamantyl methacrylate was obtained. The obtained reaction solution was cooled down to room temperature, and then a 10% by weight of aqueous solution of sodium hydroxide was added while stirring to neutralize the residual methacrylic acid and sulfuric acid. Then, the neutralized water phase was drawn out from the two-phase solution. To the residual organic phase, 0.85 g of p-methoxyphenol was added as a polymerization inhibitor. The resultant solution was washed with 5% by weight of dilute sulfuric acid and with 500 ml of ion exchange water, twice for each. After the washing, precise filtration was performed by use of a Teflon® filter having a pore diameter of 0.1 μm. Then, concentration-crystallization was performed by use of an evaporator while the temperature of the solution was kept at 40° C., until the weight of the solution became 110 g. After the concentration was finished, cooling crystallization was performed at a temperature of an ice water bath to separate the crystal by filtration. The crystal was rinsed with heptane twice, and then dried at a reduced pressure at 35° C. for 24 hours. During the process from the dehydration esterification reaction to the solid-liquid separation and until the termination of rinsing performed by use of ion exchange water, the prepared gas was kept blown into the solution. Table 1 shows the analysis results of the obtained 3-hydroxy-1-adamantyl methacrylate. Methylethylketone was used as the solvent for measuring the turbidity.