A Sulfonation Method Targeting Low Electron Density Aromatics
An electron cloud and aromatic hydrocarbon technology, applied in chemical instruments and methods, organic chemistry, sulfonic acid preparation, etc., can solve the problems of low sulfonation yield, severe reaction, insufficient sulfonation ability, etc. The effect of reducing waste acid production and dosage
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Embodiment 1
[0030]Example 1. A method for sulfonation of low electron cloud density aromatic hydrocarbons, followed by the following steps:
[0031]In a three-neck flask equipped with a stirrer and a thermometer, add 15.8g (0.1mol) of o-chloronitrobenzene, 50mL of DMF, and 0.1g of silver sulfate. Add 14.0g (0.12mol) of chlorosulfonic acid while stirring, and heat to 95℃ , Keep warm for 1 hour.
[0032]After the completion of the sulfonation reaction, the solvent DMF was distilled off under reduced pressure (-0.09MPa pressure, 90°C), the residue was poured into 100ml ice water, the pH was adjusted to 1 with 5% (mass%) hydrochloric acid, filtered, and the cake After drying (90°C to constant weight), the sulfonated product was obtained, and the product yield was 96.7%.
[0033]The structural formula of the sulfonated product is as follows:
[0034]
Embodiment 2
[0035]Example 2. A method for sulfonation of aromatic hydrocarbons with low electron cloud density, followed by the following steps:
[0036]In a three-neck flask equipped with a stirrer and a thermometer, add 12.3 g (0.1 mol) of nitrobenzene, 50 mL of chloroform, and 0.1 g of rhodium sulfate. Add 17.5 g (0.15 mol) of chlorosulfonic acid under stirring. The temperature is raised to 60°C and kept warm. 5 hours.
[0037]After the sulfonation reaction is completed, the solvent chloroform is distilled off under reduced pressure, the residue is poured into 100 mL ice water, the pH is adjusted to 1 with 5% hydrochloric acid, filtered, and the filter cake is dried to obtain the sulfonated product. The product yield is 95.3% .
[0038]The structural formula of the sulfonated product is as follows:
[0039]
[0040]In Example 3-1, the rhodium sulfate in Example 2 was changed to mercury sulfate, palladium sulfate, and thallium sulfate, and the dosage remained unchanged at 0.1 g; the rest was the same as in ...
Embodiment 4
[0044]Example 4. The chloroform in Example 2 was changed to DMSO, acetic acid, and carbon tetrachloride, respectively, and the dosage remained unchanged at 50 mL; the rest was equivalent to Example 2.
[0045]The corresponding yields of the obtained products were 95.1%, 95.2%, and 95.8%.
[0046]Comparative Example 1-1: The chloroform in Example 2 was changed to ethanol and ethyl acetate, respectively; the dosage was unchanged, still at 50 mL; the rest was the same as in Example 2.
[0047]The corresponding yield of the obtained product is only 25.3% and 33.9%.
[0048]That is, the use of ethanol and ethyl acetate as solvents will lead to the disadvantages of low yield, low conversion of raw materials, and a lot of waste acid.
[0049]Comparative Example 1-2, the use of chloroform (50 mL) as a solvent in Example 2 is eliminated, and the rest is the same as Example 2.
[0050]The yield of the resulting product is only 9.6%.
[0051]That is, if the solvent is eliminated, the viscosity increases, which is ...
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