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Para Toluenesulfonyl Chloride CAS 98-59-9

Molecular Formula: C7H7ClO2S

Formula Weight: 190.65

ZSpharmac: Para Toluenesulfonyl Chloride Supplement

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Product Name: Para Toluenesulfonyl Chloride
CAS No: 98-59-9
Purity: 99%

Basic Info

Product Name:Para Toluenesulfonyl Chloride
Other Names:Tosyl Chloride
CAS:98-59-9
Place of Origin:Shandong, China
Brand Name:ZSpharmac
Type:Organic Chemical Raw Materials
Appearance:White Crystalline Powder
EINECS No.:202-684-8
Storage:Store Below +30°C.
Provide:Para Toluenesulfonyl Chloride MSDS;
Para Toluenesulfonyl Chloride COA

What is Para Toluenesulfonyl Chloride?

p-Toluenesulfonyl chloride is an important fine chemical product, which is widely used in dye and pharmaceutical industries. It can be used as a basic raw material for the preparation of ice dyes, disperse dyes and intermediates of organic pigments. It is an important raw material for organic synthesis of drugs, mainly used for the synthesis of chloramphenicol, chloramine-T, thiamphenicol and other drugs. In the pharmaceutical industry, it is used as an intermediate for the synthesis of more than ten antibacterial and anti-inflammatory drugs such as betamethasone and metsulfuron. It can also be used in the synthesis of plastic plasticizers, resins, coatings, pesticides and photosensitive materials.In the pesticide market, it is primarily utilized for the manufacturing of mesotrione, sulcotrione, sulfapyr, etc. With the constant development of the dyestuff, pharmaceutical as well as pesticide markets, the worldwide need for this range is raising, specifically the European and also American markets have broad leads.

Para Toluenesulfonyl Chloride Properties:

Melting point 65-69 °C(lit.)
Boiling point 134 °C10 mm Hg(lit.)
density 1,006 g/cm3
vapor pressure 1 mm Hg ( 88 °C)
RTECS DB8929000
Fp 128 °C
storage temp. Store below +30°C.
solubility methylene chloride: 0.2 g/mL, clear
form Crystalline Powder
color White
Water Solubility hydrolyses

 

Para Toluenesulfonyl Chloride Uses

  1. Para Toluenesulfonyl Chloride is made use of as a logical reagent and is also used in molecular rearrangement reactions in natural synthesis, dye prep work as well as hormone synthesis.
  2. Para Toluenesulfonyl Chloride is utilized in organic synthesis, sulfonamide medicines and chemical intermediates.
  3. Para Toluenesulfonyl Chloride is used in natural synthesis, dyes, resolution of main and also second amines, phenols.

Factors Affecting The Yield of Para Toluenesulfonyl Chloride

Effect of temperature: The sulfonation reaction of Para Toluenesulfonyl Chloride is an electrophilic substitution reaction. Theoretically, increasing the reaction temperature can improve the yield of the para-product, but in actual operation, the color of the reaction system becomes darker when the temperature increases. , some high-boiling products (sulfones) are formed, but the yield of the main product has not been improved. At the same time, carbon tetrachloride evaporates rapidly, and it is difficult to control the condensation and reflux. After comparing the experimental data, a more suitable reaction temperature is selected to be 60℃~ 65°C.
Feeding ratio: Toluene and chlorosulfonic acid carry out chlorosulfonation reaction, and the theoretical reaction molar ratio is toluene:chlorosulfonic acid=1:2. However, since the reaction is an equilibrium reaction, increasing the amount of chlorosulfonic acid is beneficial for the reaction to balance toward the product. After repeated experiments, it is found that it is more appropriate to increase the ratio of raw materials to 1:2.7. Continue to increase the amount of chlorosulfonic acid, and the product yield does not change much. . Introducing a diluent: it is beneficial for the reaction to be more adequate. For the traditional process, no solvent is used in the reaction system, and the product yield is 78%. In the improved process, carbon tetrachloride is introduced as a diluent in the chlorosulfonation reaction, and the product yield is It can reach 88%. In terms of the molecular structure of chlorosulfonic acid, due to the large electronegativity of the chlorine atom, the sulfur atom has a large part of the positive charge, its electrophilic reaction ability is strengthened, and the reaction speed is very fast. , local overheating is easy to produce by-products. In order to stabilize the reaction system, carbon tetrachloride is introduced as a diluent to slow down its reaction speed, and chlorosulfonic acid can be well dissolved in carbon tetrachloride, especially tetrachloride tetrachloride. The reflux condensation of carbon can remove the reaction heat well and make the reaction more stable. On the other hand, its melting point was 67°C due to the product Para Toluenesulfonyl Chloride.
The effect of catalyst on the yield: adding a composite catalyst in the reaction, mainly the front-end reaction of toluene and chlorosulfonic acid, in order to improve the para-position yield, it is necessary to increase the reaction temperature, and the increase of the reaction temperature is beneficial to the sulfone in the sulfonation reaction. In order to reduce the generation of sulfone, a sulfonated polymerization inhibitor is added. At the same time, the composite catalyst contains a certain salt, which reacts with the reaction by-product sulfuric acid to form sulfate and hydrogen chloride, so that the reversible reaction of generating Para Toluenesulfonyl Chloride moves to the right, and the yield is significantly improved. Introducing a solvent: it can improve the purity of the product in the first separation. In order to realize the safety and reliability of industrial operation, carbon tetrachloride is used in the process design to remove by vacuum distillation, and then a low-toxic solvent is added to refine and separate the product. From the experimental results , the effect is good, the product can reach more than 98% of the content in one separation.Effect of temperature: The sulfonation reaction of Para Toluenesulfonyl Chloride is an electrophilic substitution reaction. Theoretically, increasing the reaction temperature can improve the yield of the para-product, but in actual operation, the color of the reaction system becomes darker when the temperature increases. , some high-boiling products (sulfones) are formed, but the yield of the main product has not been improved. At the same time, carbon tetrachloride evaporates rapidly, and it is difficult to control the condensation and reflux. After comparing the experimental data, a more suitable reaction temperature is selected to be 60℃~ 65°C.
Feeding ratio: Toluene and chlorosulfonic acid carry out chlorosulfonation reaction, and the theoretical reaction molar ratio is toluene:chlorosulfonic acid=1:2. However, since the reaction is an equilibrium reaction, increasing the amount of chlorosulfonic acid is beneficial for the reaction to balance toward the product. After repeated experiments, it is found that it is more appropriate to increase the ratio of raw materials to 1:2.7. Continue to increase the amount of chlorosulfonic acid, and the product yield does not change much. . Introducing a diluent: it is beneficial for the reaction to be more adequate. For the traditional process, no solvent is used in the reaction system, and the product yield is 78%. In the improved process, carbon tetrachloride is introduced as a diluent in the chlorosulfonation reaction, and the product yield is It can reach 88%. In terms of the molecular structure of chlorosulfonic acid, due to the large electronegativity of the chlorine atom, the sulfur atom has a large part of the positive charge, its electrophilic reaction ability is strengthened, and the reaction speed is very fast. , local overheating is easy to produce by-products. In order to stabilize the reaction system, carbon tetrachloride is introduced as a diluent to slow down its reaction speed, and chlorosulfonic acid can be well dissolved in carbon tetrachloride, especially tetrachloride tetrachloride. The reflux condensation of carbon can remove the reaction heat well and make the reaction more stable. On the other hand, its melting point was 67°C due to the product Para Toluenesulfonyl Chloride.
The effect of catalyst on the yield: adding a composite catalyst in the reaction, mainly the front-end reaction of toluene and chlorosulfonic acid, in order to improve the para-position yield, it is necessary to increase the reaction temperature, and the increase of the reaction temperature is beneficial to the sulfone in the sulfonation reaction. In order to reduce the generation of sulfone, a sulfonated polymerization inhibitor is added. At the same time, the composite catalyst contains a certain salt, which reacts with the reaction by-product sulfuric acid to form sulfate and hydrogen chloride, so that the reversible reaction of generating Para Toluenesulfonyl Chloride moves to the right, and the yield is significantly improved. Introducing a solvent: it can improve the purity of the product in the first separation. In order to realize the safety and reliability of industrial operation, carbon tetrachloride is used in the process design to remove by vacuum distillation, and then a low-toxic solvent is added to refine and separate the product. From the experimental results , the effect is good, the product can reach more than 98% of the content in one separation.

The Preparation Method of Para Toluenesulfonyl Chloride

report one,
The reactor is a three-necked flask with a volume of 250 ml, equipped with a thermometer, mechanical stirring, a reflux condenser and a drying tube. 18.9 g of Para Toluenesulfonyl Chloride (100 mmol), 0.73 g of N,N-dimethylformamide (10 mmol) and 50 g of dichloroethane were added in one portion to the flask. Start stirring, at room temperature, the dichloroethane solution (which contains 10g triphosgene (34mmol), 50g dichloroethane) dissolved with triphosgene is slowly and uniformly added dropwise to the reaction flask, and the time for adding is 30min. Incubate for 30min after adding. After the heat preservation, the temperature was raised to an obvious reflux phenomenon in the system, and the reaction was maintained under reflux conditions for three hours. After the reaction solution was cooled, the filter cake ammonium chloride was removed by filtration, and the obtained filtrate was subjected to vacuum distillation. After 92 g of methylene chloride was recovered, the remaining filtrate was placed in a cold storage with a temperature of -10 ℃ – 0 ℃ for 24 hours, 16.5 g of white needle-like crystals were obtained, and the purity of Para Toluenesulfonyl Chloride was 98.5% by chromatographic analysis, and the yield was 85.31%.
report two,
In a 250mL reaction flask equipped with a constant pressure funnel, a stirrer and a condenser, add 30g (0.082mol, 1.0eq) of magnesium p-toluenesulfonate, add 30mL of N,N-diformylformamide solvent, and stir to make p-toluene Magnesium sulfonate was uniformly suspended in N,N-diformylformamide, 10.7g SOCl2 (0.090mol, 1.1eq) was added dropwise under argon protection, the dropping was completed, the temperature was raised to 75°C, and the reaction was maintained until the system was dissolved ( About 2 to 4 hours); add 60 mL of toluene dropwise to the system, keep stirring for 30 minutes, then cool to room temperature, add 60 mL of water, stir and separate the liquid, wash the collected organic layer with saturated saline, anhydrous sodium sulfate Dry and concentrate under reduced pressure to obtain 30.1 g of solid Para Toluenesulfonyl Chloride (purity 99.7%, molar yield 96%).
report three.
Dissolve 0.1mol (19.02g) p-toluenesulfonic acid (with crystal water, the same below) and 0.38g [BuPy]EtOSO3 in 47.55g chloroform, stir evenly, and add 0.15mol (17.48g) chlorine dropwise at 25°C Sulfonic acid. After 2.5 hours of constant temperature reaction, 0.1 mol (1.8 g) of distilled water was added to remove excess chlorosulfonic acid. The reaction solution was layered, and the waste acid and the organic phase were obtained by separating liquids through a separatory funnel. The organic phase was washed with 10 g of distilled water, and the residual p-toluenesulfonic acid in the organic phase was removed. The partition coefficient of p-toluenesulfonic acid is the ratio of the concentration of p-toluenesulfonic acid in the organic phase to the concentration in the spent acid. Analysis by liquid chromatography showed that the partition coefficient of p-toluenesulfonic acid was 0.0494; chloroform was recovered by distilling the organic phase to obtain 16.67 g of Para Toluenesulfonyl Chloride with a yield of 87.51%.
report four.
At room temperature, add 100 g of crude sodium p-toluenesulfonate salt, 200 ml of toluene, 1 ml of N,N-dimethylformamide and 67 g of thionyl chloride to a round-bottomed flask (500 mL), mix and stir for 5 minutes Then, the temperature was raised to 65°C and reacted for 8 hours, the reaction was changed to a vacuum distillation device, toluene was evaporated from the reaction solution, and after evaporation to dryness, the temperature was lowered to room temperature, 40 ml of cyclohexane was added, and the product was obtained by filtration after heating and cooling. 93 g, 95% yield.
report five.
In a 2000-liter reactor, a stirrer, a dropping funnel, a thermometer, a gas exporter, and a water absorption device for exporting the gas were installed, and 7.5 moles of chlorosulfonic acid were firstly added to the flask, and heated to about 50 °C under stirring. 2 moles of ammonium chloride were added in portions, then the temperature of the reaction content was raised to 79-86 °C, 5 moles of toluene was added dropwise, after dropping, the temperature was lowered to 35-40 °C, the other half of chlorosulfonic acid was added, and the reaction was continued for 1 After 2 hours, the temperature of the contents was lowered to 20-25°C and placed for 2 hours. At this time, almost all the para-chlorine crystals were precipitated. The crystals were separated by filtration, washed with water, and then the ortho-isomer was separated to obtain the final product pair. Para Toluenesulfonyl Chloride , the content is more than 95%, the water content is about 4.0%, the melting point is about 65°C, the yield (calculated in toluene) is 78%, and the total yield including the ortho-isomer is 86-87%.

About Us

The production base is located in Zhangqiu chemical industry park and Tai’an high-tech chemical industry park. laboratory and workshop in strict accordance with the GMP standard and the product fit national ISO9001 and ISO2000 standards.

“Zhishang” products are exported to Europe, North and South America, the Middle East, Asia Pacific and Africa area, so as to establish a long-term and stable cooperation relationship with customer in the world.

Company Info
  • Business Type: Manufacturer
  • Product Range: Additive , Chemical Auxiliary & Catalyst , Organic Chemicals
  • Products/Service: Organic Intermediate,Inorganic Chemistry, APIs, Dyestuffs And Pigments, Fragrance And Spices, Food Additives
  • Total Employees: 51~100
  • Capital (Million US $): 10000000RMB
  • Year Established: 2016
Production Capacity
  • No. of Production Lines : 8
  • No. of QC Staff : 5 -10 People
  • OEM Services Provided : yes
  • Factory Size (Sq.meters) : 3,000-5,000 square meters
  • Certificate: ISO9001 , CE , GMP , API , MSDS
  • Factory Location : Diao Town Industry Park, Zhangqiu City, Jinan City, Shandong Province, China.

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FAQ

Do you accept sample order?

We will make samples before mass production, and after sample approved, we’ll begin mass production. Doing 100% inspection during production, then do random inspection before packing.

 

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Our MOQ is 1kg. But usually we accept less quantity such as 100g on the condition that sample charge is 100% paid.

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Different quantity has different discount.

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1. ≤50kg, Express delivery recommended, usually called as DDU service;

2. ≤500kg, Air shipping recommended, usually called as FOB, CFR, or CIF service;

3. >500kg, sea shipping recommended, usually called as FOB, CFR, or CIF service;

4. For high value products, please select air shipping and express delivery for safe.

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