Extraction cyclohexanol

The reaction mixture is now poured into a separatory funnel with 50 ml of ice water, and the cyclohexanol is removed by two ether extractions. The ether extracts are dried with anhydrous sodium sulfate, and the dried solution is distilled. Cyclohexanol is collected at 154-1607750 mm, expected yield 5-6 g. 

Solvent additives to the melt (Table 3) fall into two categories extractive and reactive. The extractive solvents (decane, perchloroethane, o-dichlorobenzene, and pyrrolidine) had negligible effect on solubility, possibly due to the preferential wetting of the coal by the solvent and exclusion of the ZnCl2 melt. Reactive solvents (anthracene oil, indoline, cyclohexanol, and tetralin) all incorporated strongly. Donor solvents, tetralin and indoline, increase the "corrected solubility, whereas anthracene oil and cyclohexanol have negligible effect. 

Fig. 4. Extraction of pertechnetate from aqueous solutions with cyclohexanol as a function of acid concentration ...

With all solvents studied including cyclohexanol, methyl ethyl ketone and cyclohexanone, heptavalent technetium is extracted most effectively from sodium sulfate and weakest from sodium nitrate or sodium perchlorate solutions. The data in Fig. 5 appear to be consistent with those on the solubilities of various sodium salts in pure tri-H-butyl phosphate. For example, the solubility of Na SO in TBP is extremely small compared with NaClO. ... 

The temperature of the vapour is noted and, as the vapour passes through the condenser, it condenses to a liquid and is collected in the conical flask. The cyclohexanol remains in the round-bottomed flask. The cyclohexene distillate is then further purified by solvent extraction. 

In preparing cyclohexene from cyclohexanol, the impure cyclohexene obtained during the distillation of the reaction mixture can be further purified by solvent extraction. This can be done by adding the crude cyclohexene to a separating funnel along with an equal volume of sodium chloride solution. Impurities in the cyclohexene are extracted into the lower aqueous sodium chloride layer. The cyclohexene layer is then run off and treated with anhydrous magnesium sulfate to remove any remaining water. 

Cydohexanone. 20 g of cyclohexanol is placed in a flask and to it is added a 30° mixture of 41 g of potassium dichromate, 200 c of water and 19 cc of coned sulfuric acid. Shake and cool to keep the temp below 60°, but not less than 55°. After some time, the temp will remain steady, it is then heated to 60° and cooled at room temp for 1 hour. The mixture is then added to 200 cc of water and distilled until 100 cc have been collected. Add about 24 g of sodium chloride and shake. Let stand, separate the lower layer and extract it with ether. The extract is added to the cyclohexanone upper layer, dried over anhydrous sodium sulphate, filtered, and distilled, collecting the fraction at 150-155°. Yield about 12 g of the colorless liquid. 

Gas chromatographic analysis shows that the ethereal extract contains solely cyclohexanol (>98%). 

Dried with MgSC>4, CaSC>4, NajSC or Linde type 13X molecular sieves, then distd. Cyclohexanol and other oxidisable impurities can be removed by treatment with chromic acid or dil KMnC>4. More thorough purification is possible by conversion to the bisulphite addition compound, or the semicarbazone, followed by decompn with Na2CC>3 and steam distn. [For example, equal weights of the bisulphite adduct (crystd from water) and NajCC are dissolved in hot water and, after steam distn, the distillate is saturated with NaCl and extracted with benzene which is then dried and the solvent evaporated prior to further distn]. 

In a 1-1. three-necked round-bottomed flask, equipped with a sealed stirrer, a reflux condenser, a thermometer, and a dropping funnel, is dissolved 5 g. of mercuric oxide (Note 1) in a solution of 8 ml. of concentrated sulfuric acid and 190 ml. of water. The solution is warmed to 60°, and 49.7 g. (0.40 mole) of 1-ethynyl-cyclohexanol (Note 2) is added dropwise over a period of 1.5 hours. After the addition has been completed, the reaction mixture is stirred at 60° for an additional 10 minutes and allowed to cool. The green organic layer which settles is taken up in 150 ml. of ether, and the aqueous layer is extracted with four 50-ml. portions of ether (Note 3). The combined ethereal extracts are washed with 100 ml. of saturated sodium chloride solution (Note 4) and dried over anhydrous sodium sulfate. The drying agent is removed, the ether is evaporated, and the residue is distilled under reduced pressure through a 15-cm. column packed with glass helices. The 1-acetylcyclohexanol is collected at 92-94°/15 mm. as a colorless liquid, 1.4670, dl5 1.0248 (Note 5). The yield is 37-38 g. (65-67%). 

The resulting mixture is stirred for 4 hours at room temperature and then poured, while stirring slowly, into a mixture of 25 g of ammonium chloride, 50 ml of water and 50 g of ice. The layers are separated and the aqueous layer is extracted twice with 50 ml portions of ether. The organic layers are combined, dried with sodium sulfate and evaporated. The residue is distilled, and l-(m-methoxyphenyl)-2-dimethylaminomethyl-cyclohexanol-(l), boiling point at 0.6 mm Hg 138°C to 140°C, is obtained in a yield of 78.6% of theoretical. 

The paraffin oxidation by immobilized Por and Pc complexes is strongly influenced by the polarity of the support. This has been studied in detail for the oxidation of cyclohexane with f-BuOOH by immobilized phthalocyanines. Thus, adsorption of the polar reaction products cyclohexanol and r-butyl alcohol competes with sorption of the cyclohexane reagent, particularly when a polar support such as a zeolite Y is used (124,134). Consequently, the activity decreases rapidly, and it can be restored only by extensive solvent extraction. In contrast, FePc on the apolar support carbon black is much less sensitive to this type of deactivation (121). 

D. (lR,PS,5R)-5-Methyl-Z-(l-methyl-l-phenylethyl)cyclohexanol 3. In a 500-mL round-bottomed reaction flask, fitted with a reflux condenser and Teflon coated magnetic stirring bar, 12.8 g (41 mmol) of 5 (48%) is dissolved in a solution of 300 nt of ethanol, 40 irt. of water and 4.6 g (82 mmol) of potassium hydroxide. This solution is refluxed for 2 hr. The solution is concentrated at reduced pressure to a volume of ca. 50 mL and 20D mL of water and 100 ml of ether are added. After the ether layer is separated, the aqueous phase is saturated with sodium chloride and extracted with three 50-mL portions of ether. The combined organic layers are dried over anhydrous magnesium sulfate, filtered, and the solvent Is evaporated. Kugelrohr distillation of the cloudy residual oil yields 8.9-9.2 g (92-97%) of 3, bp 105-115°C/0.01 mm [a]2°. 26.4° 0.1° (ethanol, a 1.97) (Note 19). 

How could we separate a mixture of benzoic acid and cyclohexanol Both compounds are organic, and as a result, both are soluble in an organic solvent such as CH2CI2 and insoluble in water. If a mixture of benzoic acid and cyclohexanol were added to a separatory funnel with CH2CI2 and water, both would dissolve in the CH2CI2 layer, and the two compounds would not be separated from each other. Is it possible to use extraction to separate two compounds of this sort that have similar solubility properties ... 

This difference in acid—base chemistry can be used to separate benzoic acid and cyclohexanol by the stepwise extraction procedure illustrated in Figure 19.10. This extraction scheme relies on two ba.sic principles ... 

Separation of benzoic acid and cyclohexanol by an extraction procedure... 

Thus, the water-soluble salt, C6H5COO Na (derived from CgHsCOOH by an acid-base reaction) can be separated from water-insoluble cyclohexanol by an extraction procedure. 

Because phenol (CeHsOH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCOa- Using this information, write out an extraction sequence that can be used to separate CeHsOH from cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form. 

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