2-(2-(2-Hydroxypropoxy)propoxy)-1-propanol → Tripropylene glycol 3,4-epoxycyclohexanecarboxylate
反応式
[O:1]1[CH:7]2[CH:2]1[CH2:3][CH:4]([C:8]([O:10]C)=[O:9])[CH2:5][CH2:6]2.[CH3:12][CH:13]([OH:24])[CH2:14][O:15][CH:16]([CH2:18][O:19][CH:20]([CH2:22][OH:23])[CH3:21])[CH3:17]>CCCCCCC>[O:1]1[CH:7]2[CH:2]1[CH2:3][CH:4]([C:8]([OH:10])=[O:9])[CH2:5][CH2:6]2.[CH3:12][CH:13]([OH:24])[CH2:14][O:15][CH:16]([CH2:18][O:19][CH:20]([CH2:22][OH:23])[CH3:21])[CH3:17]参加物
4
反応条件
- 温度
- 107.5 °C
実験手順
Methyl 3,4-epoxycyclohexanecarboxylate (50 g), and tripropylene glycol (33.8 g) in 60 milliliters (“mL”) of heptane were heated in a flask equipped with a 120-mL insulated Vigreaux column, Dean-Stark trap, drying tube and magnetic stirrer. The Dean-Stark trap was pre-filled with heptane. After refluxing the heptane for 60 minutes to azeotropically remove any water moisture, 0.0340 g of anhydrous sodium acetate (406 ppm by weight based on undiluted starting materials) was added as a transesterification catalyst. Methanol/heptane azeotrope was collected in the Dean-Stark trap and heating was continued for 405 minutes. The reaction temperature gradually increased from 102 to 113° C. during the course of the reaction, and the lower (methanol-rich) layer had a volume of 20.2 mL. Heating was continued and a nitrogen sparge was used to help remove any remaining heptane solvent by distillation. The product was allowed to cool to room temperature. The product consisted of 86 wt % of the mono and diepoxide adducts of tripropylene glycol, 0.8 wt % residual monoepoxide, and 14 wt % higher oligomers by uncorrected size-exclusion chromatography using THF solvent and a refractive index detector. Purity by gas chromatography was 88%. The viscosity of the product was 380 centipoise (cP) and the epoxy equivalent weight (titration) was 245 (theoretical 230). The product resin was formulated into a photo-crosslinkable material without further purification.