P-toluene sulfonyl chloride
Tosyl chloride
CAS: 98-59-9
Molecular Formula: C7H7ClO2S
P-toluene sulfonyl chloride - Names and Identifiers
| Name | Tosyl chloride |
| Synonyms | PTSC Tosyl chloride p-Tosyl Chloride 4-Tosyl chloride AKOS BBS-00004428 4-toluene sulfochloride 4-Toluene sulfochloride P-Touenesulfonyl choride 4-Toluolsulfonyl chloride 4-Toluenesulfonyl chloride 4-TOLUENESULFONYL CHLORIDE P-toluene sulfonyl chloride Toluene-4-sulfonyl chloride p-Toluenesulfonyl chloride 4-toluene sulfonyl chloride P-toluene Sulphonyl chloride 4-Methylbenzenesulfonyl chloride 4-METHYLBENZENESULFONYL CHLORIDE 4-METHYLBENZENESULPHONYL CHLORIDE p-Toluene Benzyl Sulfonyl Chloride |
| CAS | 98-59-9 |
| EINECS | 202-684-8 |
| InChI | InChI=1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3 |
| InChIKey | YYROPELSRYBVMQ-UHFFFAOYSA-N |
P-toluene sulfonyl chloride - Physico-chemical Properties
| Molecular Formula | C7H7ClO2S |
| Molar Mass | 190.65 |
| Density | 1,006 g/cm3 |
| Melting Point | 65-69°C(lit.) |
| Boling Point | 134°C10mm Hg(lit.) |
| Flash Point | 128 °C |
| Water Solubility | hydrolyses |
| Solubility | methylene chloride: 0.2g/mL, clear |
| Vapor Presure | 1 mm Hg ( 88 °C) |
| Appearance | Crystalline Powder |
| Color | White |
| Merck | 14,9534 |
| BRN | 607898 |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Substances to be avoided include strong bases and strong oxidizing agents and water. Moisture sensitive. |
| Sensitive | Moisture Sensitive |
| Refractive Index | 1.545 |
| Physical and Chemical Properties | character: White rhomboid Crystal, irritating odor |
| Use | Used as analytical reagents, but also for organic synthesis, dye preparation and hormone synthesis in the molecular rearrangement reaction |
P-toluene sulfonyl chloride - Risk and Safety
| Risk Codes | R34 - Causes burns R29 - Contact with water liberates toxic gas R41 - Risk of serious damage to eyes R38 - Irritating to the skin |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S27 - Take off immediately all contaminated clothing. S39 - Wear eye / face protection. |
| UN IDs | UN 3261 8/PG 2 |
| WGK Germany | 1 |
| RTECS | DB8929000 |
| FLUKA BRAND F CODES | 9-21 |
| TSCA | Yes |
| HS Code | 29049020 |
| Hazard Note | Corrosive |
| Hazard Class | 8 |
| Packing Group | II |
| Toxicity | LD50 orally in Rabbit: 4680 mg/kg |
P-toluene sulfonyl chloride - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | as a fine chemical product, P-Toluenesulfonyl chloride (TsCl) is widely used in the dye, pharmaceutical and pesticide industries. In the dye industry is mainly used for the manufacture of disperse, ice dye, acid dye intermediates; In the pharmaceutical industry is mainly used for the production of sulfonamides, sulfamethoxolone; Pesticide industry is mainly used for methyl sulfotridone, fine metalaxyl, etc. With the continuous development of dye, medicine, pesticide industry, the international demand for the product is growing, especially in Europe and the United States, the market prospect is broad. |
| Application | p-Toluenesulfonyl chloride (TsCl) is a white flake crystal with a melting point of 69-71 ℃, is an important intermediate in organic synthesis of drugs, mainly used in the synthesis of chloramphenicol sulfamethoxazole, chloramine-T, thiamphenicol and other drugs. This product is an intermediate of disperse dyes, ice dyes and acid dyes. It is also used in the production of the drug mesosulfuron. used as analytical reagent, also used in organic synthesis, dye preparation and molecular rearrangement reaction in hormone synthesis used in organic synthesis, sulfonamides and pesticide intermediates organic synthesis, dyes, determination of primary, secondary amines, phenols. |
| tosyl chloride | tosyl chloride is an important organic synthesis intermediate dyes, pesticides raw materials, there are three isomers, namely, M-and p-Toluenesulfonyl chlorides. Relative molecular mass 190.65. The three are irritating to the skin and mucous membranes, commonly used for O-toluene sulfonyl chloride and p-toluene sulfonyl chloride. O-Toluenesulfonyl chloride is also called 2-methylbenzenesulfonyl chloride and 2-toluenesulfonyl chloride. Colorless oily liquid. The relative density was 1.3383. Melting Point: 10.2 ° C. Boiling Point: 154 ° C. (4.800 × 103Pa), 126 ° C. (1.333 × 103Pa). Refractive index 1.5565. Insoluble in water, soluble in ether, benzene and ethanol. M-Toluenesulfonyl chloride is also called 3-methylbenzenesulfonyl chloride and 3-toluenesulfonyl chloride. Colorless oily liquid. Melting point 11.7 °c. Boiling point 146 °c (2.933 X 103Pa). Insoluble in water, soluble in ethanol, ether and benzene. p-Toluenesulfonyl chloride is also called 4-methylbenzenesulfonyl chloride and 4-toluenesulfonyl chloride. The precipitates from ether or petroleum ether are triclinic white flaky crystals. The relative density was 1.261. Melting point 71 °c. Boiling Point: 164 °c (4.4 × 103Pa), 151.6 °c (2.666 × 103Pa), 145-146 °c (2.000 × 103Pa), 134.5 °c (1.333 × 103Pa). Insoluble in water, soluble in ethanol, benzene and ether. p-Toluenesulfonyl chloride, referred to as "TsCl", has a strong nucleophilic; And nucleophilic reagent substitution reaction. |
| synthesis process | the traditional process of TsCl mainly has the following two kinds: first, toluene and excess chlorosulfonic acid were obtained by direct acid chlorination at low temperature. This method contains high O-Toluenesulfonyl chloride, P-Toluenesulfonyl chloride as its by-product, and the two are difficult to separate, energy consumption is large, toluene and chlorosulfonic acid in the presence of certain salts and a certain temperature directly with excess chlorosulfonic acid chlorination, although the method of p-toluenesulfonic acid chloride product ratio is higher, purification than the method is easy, low energy consumption, however, due to the relatively high reaction temperature, the sulfonated oil has high sulfone content and low utilization value, and the actual total yield is only about 70%. In addition, these two methods have high consumption of raw material chlorosulfonic acid, and the waste sulfuric acid produced in the production is too dilute, which is not conducive to industrial utilization and treatment. It has also been reported that the method is improved, first, the p-Toluenesulfonyl chloride in the reaction mixture is fully crystallized under certain conditions, and the crystal particles are increased, P-Toluenesulfonyl chloride is separated from the mixture by direct filtration without hydrolysis, but there are some difficulties and large investment in the selection of industrial plants. Improved Process: select the appropriate catalyst, and other optimal process conditions. |
| Influence Factors of yield | Influence of temperature: The sulfonation reaction of p-Toluenesulfonyl chloride is electrophilic substitution reaction, increasing the reaction temperature can improve the yield of the para-position product, but in actual operation, the color of the reaction system becomes darker and some high boiling products (sulfone) are formed, while the yield of the main product has not been improved, at the same time, the rapid evaporation of carbon tetrachloride, condensation reflux control is difficult, by comparison of experimental data, choose a more appropriate reaction temperature of 60 ℃ ~ 65 ℃. Feed ratio: toluene and chlorosulfonic acid chlorosulfonation reaction, the theoretical reaction molar ratio of toluene: chlorosulfonic acid = 1:2. However, because the reaction is an equilibrium reaction, increasing the amount of chlorosulfonic acid is beneficial to the reaction balance in the direction of the product. After repeated experiments, it is found that it is more appropriate to increase the ratio of raw materials to 1:2.7, and continue to increase the amount of chlorosulfonic acid, the yield of the product did not change much. Introduction of diluent: it is beneficial to the reaction more fully to 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 diluent in the chlorosulfonation reaction, the yield of the product can reach 88%, on the molecular structure of chlorosulfonic acid, due to the larger electronegativity of the chlorine atom, the sulfur atom has a larger part of the positive charge, and its electrophilic reaction ability is strengthened, the reaction rate is very fast, and the local overheating is easy to produce by-products. In order to make the reaction system stable, carbon tetrachloride is introduced as a diluent to alleviate the reaction rate, and chlorosulfonic acid can be well dissolved in carbon tetrachloride, in particular, the reflux condensation of carbon tetrachloride can remove the heat of reaction well and make the reaction more stable. On the other hand, due to the product P-Toluenesulfonyl chloride, its melting point was 67 °c. Effect of catalyst on yield: in the reaction, the composite catalyst is added, mainly in the front stage reaction of toluene and chlorosulfonic acid. In order to improve the para-site yield, the reaction temperature needs to be increased, and the reaction temperature is increased, thus, the formation of sulfone in The sulfonation reaction is facilitated, and a sulfonation inhibitor is particularly added in order to reduce the formation of sulfone. At the same time, the composite catalyst contains a certain salt, and reacts with the reaction by-product sulfuric acid to form sulfate and hydrogen chloride, so that the reverse reaction of p-Toluenesulfonyl chloride is generated to move to the right, and the yield is obviously improved. Introduction of solvent: can improve the product once separation purity in order to achieve the safety and reliability of industrial operation, in the process design, carbon tetrachloride vacuum distillation is used to remove, and then low toxic solvent is added to refine and crystallize the product, from the experimental results, the effect is good, the product separation can reach more than 98%. |
| outlook | in the synthesis of p-Toluenesulfonyl chloride, toluene was used as the starting material and carbon tetrachloride was introduced as the diluent, selection of composite catalyst, and chlorosulfonic acid acylation reaction synthesis of p-Toluenesulfonyl chloride, and the use of solvent direct crystallization purification and separation of the new process, this method can be a crystallization of p-Toluenesulfonyl chloride content as high as 98%, the appearance of white needle-like crystals, the consumption of chlorosulfonic acid is low, and the concentration of waste acid is increased, which provides convenience for the comprehensive utilization and treatment of waste acid and is suitable for industrial production. |
| references | [1] Hao Yanxia, Su Tiaoxi. Synthesis of p-Toluenesulfonyl chloride [J]. Hebei chemical industry, 2006,(06):17-18. [2] Chen Zhongxiu, Jiang Linfeng, Ding tongfu, Xu Yun, Sun radium, Yu Xingyuan. Study on the synthesis of p-Toluenesulfonyl chloride [J]. Journal of Chemical Engineering of universities, 2004,(02):254-257. [3] Xu Yun, Wang Hongliang, Jin Xingbei, Song Jianping. Study on the synthesis of p-Toluenesulfonyl chloride by a new process [J]. Zhejiang chemical industry, 2003,(10):12-13. [4] Li Junping. Preparation and analysis of p-Toluenesulfonyl chloride [J]. Shanxi chemical industry, 1996,(03):39. |
| production method | p-Toluenesulfonyl chloride is also produced in the production of O-Toluenesulfonyl chloride by chlorosulfonation of toluene. P-Toluenesulfonyl chloride was purified from the filter cake after the separation of O-Toluenesulfonyl chloride. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:12
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