7719-09-7
Thionyl chloride
CAS: 7719-09-7
Molecular Formula: Cl2OS
7719-09-7 - Names and Identifiers
| Name | Thionyl chloride |
| Synonyms | SOCl2 Thionylchlorid THIONYL CHLORIDE Thionyl chloride Sulfinyl chloride thionyl dichloride chloruredethionyle THIONYL DICHLORIDE Sulfinyl dichloride SULFUROUS OXYCHLORIDE SULFUR DICHLORIDE OXIDE Thionylchloridecolorlesspaleyellowliq |
| CAS | 7719-09-7 |
| EINECS | 231-748-8 |
| InChI | InChI=1/Cl2OS/c1-4(2)3 |
7719-09-7 - Physico-chemical Properties
| Molecular Formula | Cl2OS |
| Molar Mass | 118.97 |
| Density | 1.64g/mLat 20°C |
| Melting Point | -105 °C |
| Boling Point | 79°C(lit.) |
| Flash Point | 105°C |
| Water Solubility | REACTS |
| Solubility | Miscible with toluene, chloroform, benzene, carbon tetrachloride and diethyl ether. |
| Vapor Presure | 97 mm Hg ( 20 °C) |
| Vapor Density | 4.1 (vs air) |
| Appearance | Liquid |
| Color | ≤50(APHA) |
| Odor | Characteristic, pungent odor |
| Exposure Limit | ACGIH: TWA 50 ppmOSHA: TWA 25 ppm; STEL 125 ppmNIOSH: IDLH 2300 ppm |
| Merck | 14,9348 |
| Storage Condition | Store at RT. |
| Stability | Reacts violently with water. Incompatible with most common metals, strong reducing agents, strong bases, alcohols, amines. |
| Sensitive | Moisture Sensitive |
| Refractive Index | n20/D 1.518(lit.) |
| Physical and Chemical Properties | Colorless or light yellow volatile liquid, with a strong asphyxiating odor. |
| Use | Used in medicine, pesticides and dyes and other industries, mainly used in the production of isocarbophos, fast killer, deworming, indomethacin, vitamin A and so on |
7719-09-7 - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | R14 - Reacts violently with water R20/22 - Harmful by inhalation and if swallowed. R29 - Contact with water liberates toxic gas R35 - Causes severe burns R40 - Limited evidence of a carcinogenic effect R34 - Causes burns R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| 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.) S28 - After contact with skin, wash immediately with plenty of soap-suds. S27 - Take off immediately all contaminated clothing. |
| UN IDs | UN 1836 8/PG 1 |
| WGK Germany | 1 |
| RTECS | XM5150000 |
| FLUKA BRAND F CODES | 19 |
| TSCA | Yes |
| HS Code | 28121095 |
| Hazard Class | 8 |
| Packing Group | I |
7719-09-7 - 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 | thionyl chloride (SOCl2), also known as thionyl chloride, sulfur oxychloride, sulfur oxychloride, under normal temperature and pressure for colorless or light yellow liquid, irritating odor. Relative density 1.676, melting point -104.5 °c, boiling point 78.8 °c. Water easily decomposed into sulfur dioxide and hydrogen chloride. Dissolved in benzene, chloroform and carbon tetrachloride. Decomposition was initiated by heating to 150°C and complete at 500°C. Thionyl chloride is sometimes confused with sulfuryl chloride (SO2Cl2), but their chemical properties vary widely. The ability of the chlorine atom to replace a hydroxyl group or a sulfur group is significant. Thionyl chloride can react with hydroxy-containing phenols or alcohols to form the corresponding chlorides; And with Grignard reagents to form the corresponding sulfoxide compounds. The molecular configuration of thionyl chloride is pyramidal, in which the sulfur (VI) Center contains a pair of lone pair electrons. COCl2 is in a planar configuration. SOCl2 does not exist in nature due to the strong reaction of thionyl chloride with water. |
| purification | chloride sulfoxide (SOCl2) crude often contains sulfuryl chloride, sulfur chloride and sulfur dichloride and other impurities, such as higher purity of chloride sulfoxide, it is necessary to add sulfur powder, reflux, and resteam to obtain high purity thionyl chloride. The specific reaction is not very clear, with my analysis, may be to prevent the distillation process, the decomposition of thionyl chloride into two sulfur chloride, sulfur dioxide and chlorine. A specific purification method is as follows: after heating and refluxing 4.5 ml of thiosulfonic acid powder together with G of thiosulfonic acid powder, a colorless pure product is obtained by using a high efficiency fractionation column twice. Distillation may also be performed in the presence of triphenyl phosphite. Impurities removed should be sulfuryl chloride, sulfur monochloride and sulfur dichloride |
| Application | thionyl chloride (SOCl2) is an important organic chemical intermediates, mainly used in medicine, pesticide, dye Industry and organic synthesis industry, as a chlorinating agent. Consumption structure: the pharmaceutical industry accounted for 25%, the pesticide industry accounted for 50%, the dye industry accounted for 5%, other industries accounted for 20%, pesticide industry is the main consumption area of thionyl chloride in China, mainly used for the production of anti-inverted Amine, valerate, fenvalerate, demethrin, fenvalerate, urea, isocarbophos, fenpropathrin, endosulfan, deltamethrin, chlorpyrifos, oxazolidinone, quetiapine and warfarin, etc. since thionyl chloride can interact strongly with water, it can react with hydrous salts of metal chlorides to produce anhydrous metal chlorides. MCln · xH2O + x SOCl2 → MCln + x SO2 + 2x HCl The chlorine oxide of the metal can be obtained by heating and refluxing the thionyl chloride and the transition metal oxide: WO3 +2SOCl2 → WOCl4 +2SO2 thionyl chloride is widely used to convert carboxylic acids and alcohols to the corresponding acid chlorides and chlorinated hydrocarbons. Compared with other reagents (such as phosphorus pentachloride), thionyl chloride is often the preferred reagent, because its reaction product sulfur dioxide and hydrogen chloride are gaseous, easy to separate. Excess thionyl chloride can be removed by distillation. RC(= O)-OH + O = SCl2 → RC(= O)-Cl + SO2 + HCl R-OH + O = SCl2 → R-Cl + SO2 + HCl sulfonic acid reacts with thionyl chloride to produce sulfonyl chloride. Sulfinic acid reacts with thionyl chloride to produce sulfinyl chloride. Phosphonic acid reacts with thionyl chloride to produce phosphonyl chloride. thionyl chloride can be reacted with a mono-substituted formamide to form the corresponding isonitrile. The amide can react with thionyl chloride to form iminoyl chloride, and the first-order amide will continue to be dehydrated into nitriles when co-heated with thionyl chloride. used in pharmaceuticals, pesticides and dyes and other industries, mainly used in the production of isocarbophos, fast killer, deworming, indomethacin, vitamin A and so on used as a chlorinating agent for organic synthesis, for example, chlorination of alcohol hydroxyl groups, chlorination of carboxylic acids, chlorination of acid anhydrides, chlorine substitution of organic sulfonic acids or nitro compounds. Production of acyl chloride. Manufacture of pharmaceutical intermediates, such as anthelmintic, odorless, bleomycin. It is also used as a dehydrating agent and a solvent. It is mainly used in the manufacture of acyl chlorides, and also used in the production of pesticides, pharmaceuticals, dyes, etc. |
| Application | acyl chloride is an important carboxylic acid derivative in organic synthesis, drug synthesis and other aspects have important applications. At present, the commonly used raw materials for preparing acyl chloride are thionyl chloride, phosphorus trichloride, phosphorus pentachloride and phosgene, etc. Because of the advantages of mild reaction conditions, good purity and high yield, the synthesis of acyl chloride from thionyl chloride is widely used. Using thionyl chloride to carry out the "acylation reaction" of substituted benzoic acid is a common unit operation. In the existing process, the substituted benzoic acid is added to the organic solvent for dehydration, after completion of the dehydration, an excess of thionyl chloride was added dropwise. In order to ensure the completion of the reaction, the thionyl chloride is generally added dropwise in excess of 15-25%, and the excess thionyl chloride and the solvent are recovered after the completion of the reaction. |
| quenching method | under stirring, add to a large amount of ice water (can not be added back), confirm the reaction and then neutralize with alkali, for phosphorus oxychloride that does not react with ice water immediately, it can be slowly poured into water at room temperature to confirm that the reaction is finished, then it is added, ice cooling is added from time to time, and finally neutralization with alkali under cooling. During the treatment, it can only be slowly added to water (alkali solution), and water must not be added to the above compounds. |
| synthesis method | at present, the industrial production method of thionyl chloride (SOCl2) mainly includes chlorosulfonic acid method, sulfur dioxide gas phase method and three kinds of phosphorus oxychloride production method. consumption quota: production method, raw materials and specifications consumption quota/t · t-1 chlorosulfonic acid process chlorosulfonic acid (95%) 1.1 liquid chlorine (99%) 0.91 sulfur powder (99.5%) 0.42 sulfur dioxide gas phase sulfur (99.5%) 0.22 liquid chlorine (99%) 0.88 sulfur dioxide (99%) 0.44 phosphorus trichloride (98%) 1.3 liquid chlorine (99%) 0.66 sulfur dioxide (99%) 0.64 |
| toxicity | thionyl chloride is toxic, corrosive and tear-inducing. Invasive route: inhalation, ingestion, percutaneous absorption. Health hazards: harmful to the body after inhalation, oral or percutaneous absorption. The eyes, skin, mucous membranes and respiratory tract have a strong stimulating effect, can cause burns. After inhalation may be due to laryngeal, bronchial spasm, edema and death. Poisoning showed burning sensation, Cough, wheezing, dizziness, laryngitis, shortness of breath, Head Pain, Nausea and Vomit. Acute toxicity: LC50 2435 mg/m3 (rat inhalation) irritation: rabbit eye: 1380 µg, severe irritation. Protection: This product can burn the skin, there is stimulation of the mucosa. Wear protective equipment during operation, and immediately rinse with plenty of water if it is spattered on the skin. First aid measures skin contact: Immediately remove contaminated clothing and rinse with plenty of running water for at least 15 minutes. The patient visited hospital. Eye contact: lift the eyelids immediately and rinse thoroughly with plenty of running water or saline for at least 15 minutes. The patient visited hospital. Inhalation: rapid departure from the scene to fresh air. Keep airway unobstructed. Such as Dyspnea, to the delivery of oxygen. If breathing stops, perform artificial respiration immediately. The patient visited hospital. Ingestion: the wrong people with water gargle, to drink milk or egg white. The patient visited hospital. This product is toxic, its vapor irritates eyes and mucous membranes, and the liquid can cause burns when it touches the skin. If it is accidentally spattered on the skin or eyes, it must be quickly rinsed with a large amount of water, in severe cases, the patient should be sent to the hospital for treatment immediately. Staff should wear work clothes, anti-virus masks, protective glasses, latex gloves and other labor protection articles. Production equipment should be closed and the workshop should be well ventilated. |
| waste thionyl chloride should be how to deal with without environmental impact | recommended distillation cycle. If it is to be treated, it can be slowly added to the ice water to decompose into SO2 and HCL, and then the SO2 and HCL are treated. The large amount of waste thionyl chloride is considered to be recovered or sold for treatment, and the small amount can be added dropwise to alkaline water and neutralized after decomposition. |
| packaging and storage | packaging method: glass bottle or plastic barrel (tank) outer full opening steel barrel; Glass bottle or plastic barrel (tank) external ordinary wooden cases or half-flowered wooden cases; External ordinary wooden cases of ground glass bottles or threaded glass bottles; External ordinary wooden cases of ampoules. Precautions for storage and transportation: During railway transportation, the dangerous goods shall be loaded in strict accordance with the dangerous goods loading table in the transport rules for dangerous goods of the Ministry of Railways. The packaging should be complete and the loading should be safe. During transportation, it is necessary to ensure that the container does not leak, collapse, fall or damage. Mixing with alkali and edible chemicals is strictly prohibited. Transport vehicles shall be equipped with emergency treatment equipment for leakage during transportation. During transport should be protected against exposure to sunlight, rain, and high temperature. Road transport should follow the prescribed route, do not stay in residential areas and densely populated areas. Store in a cool, ventilated warehouse. The temperature of the library is not more than 25 degrees C, and the relative humidity is not more than 75%. Keep the container sealed. Should be stored separately from the alkali, etc., not mixed storage. The storage area shall be equipped with emergency treatment equipment for leakage and appropriate containment materials. |
| production method | is prepared by reacting sulfur dichloride with sulfur trioxide. In the chlorosulfonic acid method, sulfur powder is first added into the reactor, and chlorine gas is introduced for reaction to generate sulfur monochloride. Then a certain amount of chlorosulfonic acid and sulfur monochloride are added into the reactor, and chlorine gas is introduced below 50 ℃ for reaction, and the reacted materials are subjected to crude distillation and condensation, collect the feed liquid below 130 ℃ and send it to the distillation pan. In order to convert the low boiling point sulfur dichloride into sulfur monochloride and leave it in the pan, add 15% ~ 20% sulfur of the crude product and send it to distillation, after refluxing for 4H, after the color was normal, the fraction of gas phase 75~80 ℃ was collected, and the finished product of thionyl chloride was obtained. Its 2ClSO3H + S2C12 + C12 → 2SOC12+2SO2 + 2HCl sulfur dioxide method uses sulfur, liquid chlorine and liquid sulfur dioxide as raw materials, and adopts full circulation and liquid phase circulation method to produce high purity sulfoxide alum chloride with a purity of more than 99%, this method has advanced technology, stable product quality and less "three wastes" discharge. |
| category | corrosive article |
| toxicity grade | high toxicity |
| Acute toxicity | inhalation-rat LC50: 500 PPM/1 h |
| flammability hazard characteristics | irritating; Toxic sulfur dioxide, hydrogen chloride, chlorine gas and other gases when exposed to water; thermal decomposition of toxic sulfur oxides and chloride fumes |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from alkalis and food additives |
| fire extinguishing agent | dry sand, dry stone powder; No water |
| Occupational Standard | TWA 1 PPM (5 mg/m3); PEL 1 PPM (5 mg/m3) |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-10-11 10:09:09
7719-09-7 - Nature
Open Data Verified Data
A colorless or light yellow volatile liquid with a strong asphyxiating odor. The relative density was 1. 676; 638. Melting Point -104.5 °c. The boiling point is 76 ℃ and the refractive index is 1. 517. When heated above 140 °c, it decomposes to Cl2, S02, and S2. Can be hydrolyzed to produce S02 and hc1. Miscible with benzene, chloroform and carbon tetrachloride.
Last Update：2024-01-02 23:10:35
7719-09-7 - Preparation Method
Open Data Verified Data
- chlorosulfonic acid method: sulfur powder is first added to the reactor, and chlorine gas is introduced for reaction to generate sulfur monochloride. Then a certain amount of chlorosulfonic acid and sulfur monochloride are added into the reactor, and chlorine gas is introduced for reaction below 50 ℃. The reacted material is subjected to crude distillation and condensation, and the liquid below 130 ℃ is collected and sent to the distillation pan, so that the low boiling point sulfur dichloride is converted into sulfur monochloride and left in the pan, sulfur is added in an amount of 15% to 20% of the crude product, and then sent to Rectification. After refluxing for 4H and having normal color, a fraction of 75 to 80 ° C. In the gas phase is collected to obtain a finished thionyl chloride product.
- sulfur dioxide method: sulfur, liquid chlorine and liquid sulfur dioxide as raw materials, the use of full cycle and liquid phase cycle method, the production of high purity thionyl chloride, purity of more than 99%, the method of advanced technology, product quality and stability, the discharge of "three wastes" was low.
Last Update：2022-01-01 10:37:58
7719-09-7 - Use
Open Data Verified Data
chlorinating agents used in organic synthesis, such as chlorination of alcohol hydroxyl groups, chlorination of carboxylic acids, chlorination of acid anhydrides, chlorine substitution of organic sulfonic acids or nitro compounds. Production of acyl chloride. Manufacture of pharmaceutical intermediates, such as anthelmintic, odorless, bleomycin. It is also used as a dehydrating agent and a solvent.
Last Update：2022-01-01 10:37:58
7719-09-7 - Safety
Open Data Verified Data
- This product has low toxicity. The production workshop should be well ventilated and the equipment should be closed. Operators should wear protective equipment.
- this product should be placed in glass bottles and plastic barrels, tightly sealed, and protected by wooden boxes. Light loading and light unloading to prevent damage.
Last Update：2022-01-01 10:37:59
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