2-Chlorophenol 95-57-8

  Uses: p-Chlorophenol is primarily used in industries such as pesticides, pharmaceuticals, dyes, and plastics; it also serves as an alcohol denaturant and a selective solvent for refining mineral oil. Additionally, it is used in microscopic analysis and as a plant growth promoter. In dye synthesis, it reacts with dilute nitric acid to form mono- and di-nitro derivatives, which are dye intermediates; these can be further synthesized into various dyes, such as Neutral Brilliant Green BL. It is used to manufacture dyes and pharmaceuticals, and also functions as an alcohol denaturant and a selective solvent for mineral oil refining. In the pesticide industry, it is mainly used to synthesize Triadimefon, Fenarimol, wool fungicides, 4-CPA (a multifunctional plant growth regulator), Propaphos (a systemic insecticide), Phosacetim, other insecticides, Chlorfenson (a non-systemic acaricide), Chlorfenprop-methyl, and Chlorfenethol. In the pharmaceutical industry, it is used for carboxylation to produce sodium 5-chloro-2-hydroxybenzoate and for the synthesis of Clofibrate, p-chlorophenoxyisobutyric acid, and other drugs; it is also used to synthesize the antioxidant BHA (butylated hydroxyanisole). Production Methods: There are various methods for producing p-chlorophenol, categorized by the raw materials used: (1) Direct chlorination of phenol: Direct chlorination yields three isomers—para-, ortho-, and meta-chlorophenol—with p-chlorophenol obtained through separation. Depending on the chlorinating agent and solvent employed, this method is subdivided into three types: (A) Sulfuryl chloride method: Phenol is heated until molten, then cooled to 40°C. Sulfuryl chloride is added slowly over approximately 40–45 minutes. The mixture is stirred for 4 hours, then held at 30–40°C for 4 hours, followed by 4 hours at 40–45°C. Off-gases are absorbed by an alkaline solution. Upon completion of the reaction, the mixture is cooled to room temperature, washed sequentially with water, 10% sodium carbonate solution, and water, and then subjected to reduced-pressure distillation. The fraction collected at 110–115°C (2.67 kPa) yields p-chlorophenol. This method also produces 25–30% of o-chlorophenol as a by-product. (B) Benzene solvent method: This product is obtained by the direct chlorination of phenol, using benzene as the solvent and chlorine gas as the chlorinating agent. (C) Solvent-free chlorination method: Monochlorophenol is produced by directly chlorinating molten phenol with chlorine gas, using catalysts such as iron or bromine. The reaction mixture is washed and then subjected to reduced-pressure distillation; the fraction containing ≥95% p-chlorophenol is collected. (2) p-Dichlorobenzene hydrolysis method: Produced by the hydrolysis of p-dichlorobenzene (using water or alcohol) with benzene as the solvent. (3) Chlorination of sodium phenolate yields a mixture containing o-chlorophenol, p-chlorophenol, and 2,4-dichlorophenol. Upon fractional distillation under reduced pressure, the high-boiling fraction (85–132°C at 2.0 kPa) is collected and cooled to below 10°C, causing p-chlorophenol to crystallize out; it is then isolated to obtain the product. (4) Produced from p-aminophenol via diazotization followed by substitution with cuprous chloride.

Uses: p-Chlorophenol is primarily used in industries such as pesticides, pharmaceuticals, dyes, and plastics; it also serves as an alcohol denaturant and a selective solvent for refining mineral oil. Additionally, it is used in microscopic analysis and as a plant growth promoter. In dye synthesis, it reacts with dilute nitric acid to form mono- and di-nitro derivatives, which are dye intermediates; these can be further synthesized into various dyes, such as Neutral Brilliant Green BL. It is used to manufacture dyes and pharmaceuticals, and also functions as an alcohol denaturant and a selective solvent for mineral oil refining. In the pesticide industry, it is mainly used to synthesize Triadimefon, Fenarimol, wool fungicides, 4-CPA (a multifunctional plant growth regulator), Propaphos (a systemic insecticide), Phosacetim, other insecticides, Chlorfenson (a non-systemic acaricide), Chlorfenprop-methyl, and Chlorfenethol. In the pharmaceutical industry, it is used for carboxylation to produce sodium 5-chloro-2-hydroxybenzoate and for the synthesis of Clofibrate, p-chlorophenoxyisobutyric acid, and other drugs; it is also used to synthesize the antioxidant BHA (butylated hydroxyanisole). Production Methods: There are various methods for producing p-chlorophenol, categorized by the raw materials used: (1) Direct chlorination of phenol: Direct chlorination yields three isomers—para-, ortho-, and meta-chlorophenol—with p-chlorophenol obtained through separation. Depending on the chlorinating agent and solvent employed, this method is subdivided into three types: (A) Sulfuryl chloride method: Phenol is heated until molten, then cooled to 40°C. Sulfuryl chloride is added slowly over approximately 40–45 minutes. The mixture is stirred for 4 hours, then held at 30–40°C for 4 hours, followed by 4 hours at 40–45°C. Off-gases are absorbed by an alkaline solution. Upon completion of the reaction, the mixture is cooled to room temperature, washed sequentially with water, 10% sodium carbonate solution, and water, and then subjected to reduced-pressure distillation. The fraction collected at 110–115°C (2.67 kPa) yields p-chlorophenol. This method also produces 25–30% of o-chlorophenol as a by-product. (B) Benzene solvent method: This product is obtained by the direct chlorination of phenol, using benzene as the solvent and chlorine gas as the chlorinating agent. (C) Solvent-free chlorination method: Monochlorophenol is produced by directly chlorinating molten phenol with chlorine gas, using catalysts such as iron or bromine. The reaction mixture is washed and then subjected to reduced-pressure distillation; the fraction containing ≥95% p-chlorophenol is collected. (2) p-Dichlorobenzene hydrolysis method: Produced by the hydrolysis of p-dichlorobenzene (using water or alcohol) with benzene as the solvent. (3) Chlorination of sodium phenolate yields a mixture containing o-chlorophenol, p-chlorophenol, and 2,4-dichlorophenol. Upon fractional distillation under reduced pressure, the high-boiling fraction (85–132°C at 2.0 kPa) is collected and cooled to below 10°C, causing p-chlorophenol to crystallize out; it is then isolated to obtain the product. (4) Produced from p-aminophenol via diazotization followed by substitution with cuprous chloride.

Uses: p-Chlorophenol is primarily used in industries such as pesticides, pharmaceuticals, dyes, and plastics; it also serves as an alcohol denaturant and a selective solvent for refining mineral oil. Additionally, it is used in microscopic analysis and as a plant growth promoter. In dye synthesis, it reacts with dilute nitric acid to form mono- and di-nitro derivatives, which are dye intermediates; these can be further synthesized into various dyes, such as Neutral Brilliant Green BL. It is used to manufacture dyes and pharmaceuticals, and also functions as an alcohol denaturant and a selective solvent for mineral oil refining. In the pesticide industry, it is mainly used to synthesize Triadimefon, Fenarimol, wool fungicides, 4-CPA (a multifunctional plant growth regulator), Propaphos (a systemic insecticide), Phosacetim, other insecticides, Chlorfenson (a non-systemic acaricide), Chlorfenprop-methyl, and Chlorfenethol. In the pharmaceutical industry, it is used for carboxylation to produce sodium 5-chloro-2-hydroxybenzoate and for the synthesis of Clofibrate, p-chlorophenoxyisobutyric acid, and other drugs; it is also used to synthesize the antioxidant BHA (butylated hydroxyanisole). Production Methods: There are various methods for producing p-chlorophenol, categorized by the raw materials used: (1) Direct chlorination of phenol: Direct chlorination yields three isomers—para-, ortho-, and meta-chlorophenol—with p-chlorophenol obtained through separation. Depending on the chlorinating agent and solvent employed, this method is subdivided into three types: (A) Sulfuryl chloride method: Phenol is heated until molten, then cooled to 40°C. Sulfuryl chloride is added slowly over approximately 40–45 minutes. The mixture is stirred for 4 hours, then held at 30–40°C for 4 hours, followed by 4 hours at 40–45°C. Off-gases are absorbed by an alkaline solution. Upon completion of the reaction, the mixture is cooled to room temperature, washed sequentially with water, 10% sodium carbonate solution, and water, and then subjected to reduced-pressure distillation. The fraction collected at 110–115°C (2.67 kPa) yields p-chlorophenol. This method also produces 25–30% of o-chlorophenol as a by-product. (B) Benzene solvent method: This product is obtained by the direct chlorination of phenol, using benzene as the solvent and chlorine gas as the chlorinating agent. (C) Solvent-free chlorination method: Monochlorophenol is produced by directly chlorinating molten phenol with chlorine gas, using catalysts such as iron or bromine. The reaction mixture is washed and then subjected to reduced-pressure distillation; the fraction containing ≥95% p-chlorophenol is collected. (2) p-Dichlorobenzene hydrolysis method: Produced by the hydrolysis of p-dichlorobenzene (using water or alcohol) with benzene as the solvent. (3) Chlorination of sodium phenolate yields a mixture containing o-chlorophenol, p-chlorophenol, and 2,4-dichlorophenol. Upon fractional distillation under reduced pressure, the high-boiling fraction (85–132°C at 2.0 kPa) is collected and cooled to below 10°C, causing p-chlorophenol to crystallize out; it is then isolated to obtain the product. (4) Produced from p-aminophenol via diazotization followed by substitution with cuprous chloride.