Synthesis of 4,5-Diphenyl Imidazolone and Studies on its Fluorescent Effect

4,5-Diphenyl-Imidazolone의 合成 及 螢光效果에 關한 硏究

  • Published : 19571100

Abstract

4,5-Diphenyl Imidazolone is synthesized from Benzoin, Urea, and Acetic acid catalyser. Nowadays, it is being used as an optical bleaching agent for wool and nylon textiles. Up to now, only one process of synthesis has been known. In order to find out the best conditions governing the yield were examined under various catalysers and conditions. In this experiment, the summary of results were as follows. a. On Acetic acid catalyser. The maximum yield conditions were mol ratio (Benzoin: Urea: Acetic acid) 1 : 2 : 14, Acetic acid concentration 99.9%. Reaction temperature 115$^{\circ}$. Under reaction time of 2 hours, above yield was 96.4%. b. On Mineral acid Catalyser. In using of Sulfonic acid, the color of solution was changed dark purlish black. With other mineral acid catalysers, in spite of increasing of temperature, it was proved that Benzoin floats on the solution, so that this reaction could not be continue. c. On Phosphoric acid catalyser. It was made clear that it can not be used for this reaction. d. On Sodium hydroxide catalyser. As one of Alkali catalyser, Sodium hydroxide was examined but this was unsuitable substance for this reaction. e. On Formic acid catalysers. The maximum yield conditions were mol ratio (Benzoin: Urea: Formic acid) 1: 2: 30. Formic acid concentration 85.%. Reaction temperature 150∼110$^{\circ}$. Under reaction time of 90 minutes, the best yield was 87%. Hereby, it was proved that organic acids such as Acetic acid and Formic acid can be used. When using Acetic acid, the yield was better than Formic acid, but it takes longer reaction time than Formic acid. About the fluorescent effect, the temperature of dye-bath must not be over 904,5-Diphenyl Imidazolone is synthesized from Benzoin, Urea, and Acetic acid catalyser. Nowadays, it is being used as an optical bleaching agent for wool and nylon textiles. Up to now, only one process of synthesis has been known. In order to find out the best conditions governing the yield were examined under various catalysers and conditions. In this experiment, the summary of results were as follows. a. On Acetic acid catalyser. The maximum yield conditions were mol ratio (Benzoin: Urea: Acetic acid) 1 : 2 : 14, Acetic acid concentration 99.9%. Reaction temperature 115$^{\circ}$. Under reaction time of 2 hours, above yield was 96.4%. b. On Mineral acid Catalyser. In using of Sulfonic acid, the color of solution was changed dark purlish black. With other mineral acid catalysers, in spite of increasing of temperature, it was proved that Benzoin floats on the solution, so that this reaction could not be continue. c. On Phosphoric acid catalyser. It was made clear that it can not be used for this reaction. d. On Sodium hydroxide catalyser. As one of Alkali catalyser, Sodium hydroxide was examined but this was unsuitable substance for this reaction. e. On Formic acid catalysers. The maximum yield conditions were mol ratio (Benzoin: Urea: Formic acid) 1: 2: 30. Formic acid concentration 85.%. Reaction temperature 150∼110$^{\circ}$. Under reaction time of 90 minutes, the best yield was 87%. Hereby, it was proved that organic acids such as Acetic acid and Formic acid can be used. When using Acetic acid, the yield was better than Formic acid, but it takes longer reaction time than Formic acid. About the fluorescent effect, the temperature of dye-bath must not be over 90$^{\circ}$. and the ratio of 4,5-Diphenyl Imidazolone and water should be from 1:50000. to 1:10000. It proved that the best effect on textiles, and the best condition were dye-temperature near 704,5-Diphenyl Imidazolone is synthesized from Benzoin, Urea, and Acetic acid catalyser. Nowadays, it is being used as an optical bleaching agent for wool and nylon textiles. Up to now, only one process of synthesis has been known. In order to find out the best conditions governing the yield were examined under various catalysers and conditions. In this experiment, the summary of results were as follows. a. On Acetic acid catalyser. The maximum yield conditions were mol ratio (Benzoin: Urea: Acetic acid) 1 : 2 : 14, Acetic acid concentration 99.9%. Reaction temperature 115$^{\circ}C$. . Under reaction time of 2 hours, above yield was 96.4%. b. On Mineral acid Catalyser. In using of Sulfonic acid, the color of solution was changed dark purlish black. With other mineral acid catalysers, in spite of increasing of temperature, it was proved that Benzoin floats on the solution, so that this reaction could not be continue. c. On Phosphoric acid catalyser. It was made clear that it can not be used for this reaction. d. On Sodium hydroxide catalyser. As one of Alkali catalyser, Sodium hydroxide was examined but this was unsuitable substance for this reaction. e. On Formic acid catalysers. The maximum yield conditions were mol ratio (Benzoin: Urea: Formic acid) 1: 2: 30. Formic acid concentration 85%. Reaction temperature 150∼110$^{\circ}C$. Under reaction time of 90 minutes, the best yield was 87%. Hereby, it was proved that organic acids such as Acetic acid and Formic acid can be used. When using Acetic acid, the yield was better than Formic acid, but it takes longer reaction time than Formic acid. About the fluorescent effect, the temperature of dye-bath must not be over 90$^{\circ}C$. and the ratio of 4,5-Diphenyl Imidazolone and water should be from 1:50000. to 1:10000. It proved that the best effect on textiles, and the best condition were dye-temperature near 70$^{\circ}C$. and dye-time 15 minutes. . and dye-time 15 minutes. . and the ratio of 4,5-Diphenyl Imidazolone and water should be from 1:50000. to 1:10000. It proved that the best effect on textiles, and the best condition were dye-temperature near 70$^{\circ}C$. and dye-time 15 minutes.

Keywords

References

  1. 化學과 工業 v.7 小泉正夫
  2. J. Am. Chem. Soc. v.73 R.R.Hentz;M.Burton
  3. 新有機化學反應 小田良平
  4. 應用有機合成化學 小田良平
  5. Org. Synth. (合本 II)
  6. 分光化學 紫田雄次
  7. 工業化學雜誌 鶴田禎二;古川淳二
  8. 工業化學雜誌 失部;林
  9. 化學과 工業 v.7 no.5 小田;吉田
  10. 化學實驗學. 物理化學 v.IV 上原