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Hiroto Yoshitake: Chemical Studies on Hydrogenation of 2-Phenylphenol and its Hydrogenated Products. I. Separation and Purification of 2- and 4-Phenylphenol from Distillation Residue in Phenol Production. (Ube Nitrogen Factory, Ube Industries Ltd.*1)
| Content Provider | Semantic Scholar |
|---|---|
| Author | Hiroto Yoshitake |
| Copyright Year | 2009 |
| Abstract | 2-Phenylphenol is obtained on industrial as well as laboratory scale by the purification of distillation residue of synthetic phenol or from the dehydrogeneous condensation of phenol. These procedures are superior to others because of an inexpensive and steady large scale supply of starting material. Since 2 and 4-phenylphenol both exist in these starting materials and form a solid mixture in all proportions, their isolation becomes difficult. The reexamination of the various known procedures of their purification indicated that inspite of troublesome methods, the purity and the yields of the products are not satisfactory. During our studies concerning the isolation of pure 2-phenyl phenol, which is required for hydrogenation, from the distillation residue, we found the solubility ratio of two isomers of phenylphenol in aliphatic alcohol to be much larger than those in petroleum type solvents such as petroleum benzin. Using this property we succeeded in isolating pure 2 and 4-phenylphenols in high yields by the comparatively simple procedure. In this case, the sudden change in solubility of 2-phenylphenol, which results by its transformation into its m.p. 23•K crystalline form, was observed. The sulfur containing impurity in the 2-phenylphenol fraction of synthetic crude phenol obtained by sulfonation method, is presumed to be a cause of troublesome purification of 2-phenylphenol. Desulf urisation of impure 2-phenylphenol (m.p. 58•`59•K, S, 0.3%) with 5% Raney nickel by weight of starting material, at initial hydrogen pressure, 70kg./cm2, temperature, 120•K and time, 50 min., gave 2-phenylphenol, m.p. 57•`57.5•K, S, 0.0007%. When 10% of Raney nickel at atmospheric hydrogen pressure, temperature, 120•K, time, 3 hours was used, 2-phenylphenol m.p. 57.5•`58•K, 0.01% was obtained. |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | https://www.jstage.jst.go.jp/article/yakushi1947/83/5/83_5_527/_pdf/-char/en |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
