Sodium benzenesulfonate

Benzene SuIfona.tion. In the benzene sulfonation process, benzene reacts with concentrated sulfuric acid to form benzenesulfonic acid at about 150°C. The benzenesulfonic acid is neutralized with sodium sulfate to produce sodium benzenesulfonate, which is then fused with caustic soda to yield sodium phenate. The sodium phenate is acidified with sulfur dioxide and a small amount of sulfuric acid to release the phenol from the sodium salt. The phenol yield by this process can be as high as 88 mol % to that of the theoretical value based on benzene. Plants employing this technology have been shut down for environmental and economic reasons. 

Sodium benzenesulfonate [515-42-4] M 150.1, pK 0.70 (2.55) (for PhS03H2). Crystd from EtOH or aqueous 70-100% MeOH, and dried under vacuum at 80-100 . 

The melting point of pure /3-naphthylpiperidine is 58-58.5°. By the same procedure the submitters have obtained N-phenylpiperidine (94%) from sodium benzenesulfonate and N-a-naphthylpiperidine (23%) from sodium a-naphthalenesul-fonate. 

Sodium benzenesulfonate, reaction with piperidine to form N-phenylpi-peridine, 40, 75... 

C36H60O30,C3H7O3S-,Na+,9 H20 Cyclomaltohexaose-sodium 1-pro-panesulfonate, nonahydrate (ACDPRS)129 P212121 Z= 2 Dx = 1.42 R = 0.08 for 2,219 intensities. This structure is a channel type, with the molecules of cyclomaltohexaose stacked head-to-tail. It is almost isomorphous with the sodium benzenesulfonate complex.275... 

CasHgoO-jo CeH503S Na+ 10 H20 Cyclomaltohexaose-sodium benzenesulfonate, decahydrate CDXBZS 43 355... 

The use of ion pairing agents, such as sodium benzenesulfonate, may be helpful in the analysis of complex mixtures of quaternary ammonium compounds, as they modify their retention times418. 

If the sodium benzenesulfonate is to be isolated, the mixture is evaporated to dryness on a water bath. If it is desired to have the product as free as possible from inorganic salts, the paste may be filtered and the precipitate dried. This procedure entails considerable loss, of course. 

The crude paste of sodium benzenesulfonate (about 50 per cent), obtained as described in section 4 above, is used as the starting material. A test is made to determine the weight of solids in the paste, assuming arbitrarily that the solid substance is pure sodium benzenesulfonate. It is theoretically possible to fuse 2.25 parts of sodium benzenesulfonate with 1 part of caustic soda, but practically, only 1.65 parts can be used. 

Sulfonic acids are converted to the corresponding acid halides in much the same way as carboxylic acids. Thionyl chloride is the best reagent for the preparation of methanesulfonyl chloride (83%). By heating with a large excess of thionyl chloride, however, p-toluenesulfonic acid is converted into its anhydride (87%). Benzenesulfonyl chloride is made in 80% yield by the action of either phosphorus pentachloride or phosphorus oxychloride at 180° on sodium benzenesulfonate. Chlorosulfonic and fluorosulfonic acids are used in the conversion of sodium p-chloro-benzenesulfonate to the corresponding sulfonyl halides (85 8S>%). ... 

We shall refer to this as the n n interaction argument. It has been formulated ba,sed on the following experiments (1) adsorption isotherms of phenol, nitrobenzene, and sodium benzenesulfonate on a series of activated carbons and carbon blacks and (2) characterization of the surface chemistry of as-received and chemically modified carbons. The authors did not report the pH in fact, this word is not even mentioned in any of their papers on this subject [450,331,332]. 

Preparative electrolyses of diphenyl disulfide and 4-bromophenyl 4-nitrophenyl disulfide afforded, respectively, sodium benzenesulfonate (20%) and bis(4-bromophenyl) and bis(4-nitrophenyl) disulfides with an overall yield of 80% [37]. 

Historically, phenol was produced by the distillation of coal tar. Today, phenol is prepared by one of several synthetic methods, such as the fusion of sodium benzenesulfonate with sodium hydroxide followed by acidification the hydrolysis of chlorobenzene by dilute sodium hydroxide at high temperature and pressure to give sodium phenate, which on acidification liberates phenol (Dow process) or the catalytic vapor-phase reaction of steam and chlorobenzene at 500°C (Raschig process). 

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