RI 4755 Phenol And Cresols In Coal Tar From Coals Carbonized At 800° And 900° C.

Phenol was discovered in coal tar by Runge (1)1/ in 1834 and was isolated (2) in 1841 as pure phenol by distilling the tar, extracting with caustic soda, acidifying the extract, and fractionating the tar acids. Later, o-cresol was isolated (3) through careful fractional distillation of the tar-acid mixture. The m-and p-cresols distilled within a boiling range of about 1.50 c. and had to be separated by other means. Raschig (4) fractionated the tar-acid mixture to obtain pure o-cresol, sulfonated the mixture of m-and p-cresols, and treated the cresol-sulfonic acids with superheated steam at 1200 to 1300 c. to hydrolyze the m-cresol sulfonic acid, the p-isomer was not affected at that temperature. He also attempted to make use of the different crystallizabilities of the m-and p-cresol sulfonic acids (5). When treated with sodium bisulfate and sodium pyro-sulfate at 100° to 110° C. or with sulfuric acid (90/0) at 20° C., only the m-cresol was sulfonated (6). Hoffman-La Roche (7) treated the meta-para mixture with concentrated sulfuric acid at 40° to 100° C., when m-cresol and part of the p-cresol was sulfonated, and precipitated the m-cresol sulfonic add by diluting with water. The same sort of separation may be carried out by means of 80 percent sulfuric acid at 35° C. and 35 mm pressure (8).