反应详情

温度

55 °C

Lauryl alcohol in the amount of 294.4 g was heated in a flask of 1 L to a temperature of 60° C. One hundred grams (100 g) of gallic acid was added (purity 90%) together with 1 ml of sulfuric acid (96%) as a catalyst. The mixture was submitted to reaction in a Rotavapor at a temperature of approximately 160° C. and a vacuum of −0.4 bar. While reacting, the azeotropic water/lauryl alcohol was distilled off. Approximately 5 to 6 hours were needed for completion. The percent of remaining gallic acid was controlled by HPLC. When the remaining gallic acid was less than 1%, the process can be taken to the next step. The distilled azeotropic water/lauryl alcohol mixture was separated by means of a separation funnel and the lauryl alcohol can be re-used after quality control by GC. The remaining reaction mixture was cooled down to approximately 55° C., while stirring. In another flask of 2 L with reflux cooler and stirrer, 1 L of petroleum ether (Bp. 40-60° C.) was heated to approximately 55° C. When both the petroleum ether and the reaction mixture had the same temperature (approximately 55° C.), the reaction mixture was slowly added to the petroleum ether while stirring. The mixture of the reactants and the petroleum ether was cooled down over a period of approximately 5 hours to room temperature (hour 0, temp. 55° C.; h. 0.5, temp. 60° C.; h. 1, temp. 55° C.; h.2, temp. 45° C.; h3, temp. 35° C.; h. 4, temp. 25° C.; h. 5, temp. 25° C.). The lauryl gallate crystallized and was filtered via a vacuum sucked glass filter. Solid impure lauryl gallate and filtrate A (lauryl gallate, lauryl alcohol, petroleum ether) were obtained. The solid impure lauryl gallate was mixed again with 0.5 L of petroleum ether (Bp. 40-60° C.), but this time at room temperature. Again, this mixture was filtered by a vacuum sucked glass filter. This time pure lauryl gallate and filtrate B (lauryl gallate, lauryl alcohol, petroleum ether) were obtained. Filtrate A and B were combined and the petroleum ether was recovered via vacuum distillation with a Rotavapor (temp. 60° C., −0.4 Bar). After quality control, the petroleum ether could be re-used. The residue was also checked for remaining lauryl gallate and lauryl alcohol by HPLC and GC, it can be re-used at the start of a next batch. Drying of the pure lauryl gallate for 24 hours at approximately 60° C. and at a vacuum of −0.4 Bar in a vacuum oven, yields crystalline lauryl gallate. Lauryl gallate was obtained as a crystalline silver white powder with a purity of 81.35%. The conversion rate was rather good as only 0.2% of gallic acid was found remaining in the reaction mixture.

1. customThe mixture was submitted to reaction in a Rotavapor at a temperature of approximately 160° C.
2. distillationthe azeotropic water/lauryl alcohol was distilled off
3. customApproximately 5 to 6 hours
4. customThe distilled azeotropic water/lauryl alcohol mixture was separated by means of a separation funnel
5. customThe remaining reaction mixture
6. temperaturewas heated to approximately 55° C
7. customthe same temperature (approximately 55° C.)
8. stirringwhile stirring
9. additionThe mixture of the reactants
10. custom55° C.
11. custom60° C.
12. custom55° C.
13. custom45° C.
14. custom35° C.
15. custom25° C.
16. custom25° C.
17. customThe lauryl gallate crystallized
18. filtrationwas filtered via a vacuum
19. filtrationfilter