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Thionyl chloride

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Products Intro:Product Name:Thionyl chloride
CAS:7719-09-7
Purity:Standard for GC,>99.7% Package:5ml
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Products Intro:Product Name:Thionyl chloride
CAS:7719-09-7
Purity:Standard for GC,>99.7% Package:119RMB/5ML
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Products Intro:Product Name:Thionyl chloride, 1M soln. in dichloroMethane
CAS:7719-09-7
Package:100Ml Remarks:H31857
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Products Intro:Product Name:Thionyl chloride
CAS:7719-09-7
Purity:98% Package:1kg,5kg,25kg
Thionyl chloride Chemical Properties
Melting point -105 °C
Boiling point 79 °C(lit.)
density 1.64 g/mL at 20 °C
vapor pressure 97 mm Hg ( 20 °C)
refractive index n20/D 1.518(lit.)
Fp 105°C
storage temp. Store at RT.
solubility Miscible with toluene, chloroform, benzene, carbon tetrachloride and diethyl ether.
form Liquid
color ≤50(APHA)
Water Solubility REACTS
Sensitive Moisture Sensitive
Merck 14,9348
Stability:Reacts violently with water. Incompatible with most common metals, strong reducing agents, strong bases, alcohols, amines.
CAS DataBase Reference7719-09-7(CAS DataBase Reference)
NIST Chemistry ReferenceThionyl chloride(7719-09-7)
Safety Information
Hazard Codes C
Risk Statements 14-20/22-29-35-40-34-20/21/22
Safety Statements 26-36/37/39-45-28-27
RIDADR UN 1836 8/PG 1
WGK Germany 1
RTECS XM5150000
19
TSCA Yes
HazardClass 8
PackingGroup I
HS Code 28121095
Hazardous Substances Data7719-09-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Thionyl chloride English
SigmaAldrich English
ACROS English
ALFA English
Thionyl chloride Usage And Synthesis
OutlineThionyl chloride, at room temperature and pressure, is a colorless or pale yellow liquid with a pungent odor. It has a relative density of 1.676, melting point of-104.5 ℃ and the boiling point of 78.8 ℃. Upon coming across water, it is easily decomposed into sulfur dioxide and hydrogen chloride. It is soluble in benzene, chloroform and carbon tetrachloride. It begins to decompose upon being heated to 150 °C with complete decomposition at 500°C. Thionyl chloride sometimes can be easily confused with thionyl chlorine (SO2Cl2). However, these two compounds actually have a large difference in their chemical nature with its chlorine atom having a strong substitution capacity on hydroxyl group or sulfur group. Thionyl chloride can form corresponding chlorides with hydroxyl-containing phenol or hydroxyl-containing alcohol to form the corresponding chlorides; it can have reaction with Grignard reagent to generate the corresponding sulfoxide compound. The molecular structure of thionyl chloride is cone type wherein the sulfur (VI) center contains one lone pair of electrons. However, COCl2 has planar configuration. Owing to the strong reaction between the thionyl chloride and water, SOCl2 does not exist in nature.
PurificationThionyl chloride crude product often contains impurities including sulfuryl chloride, sulfur monochloride and sulfur dichloride. In order to obtain a higher purity of thionyl chloride, sulfur powder has to be added for refluxing and distillation to obtain high-purity chloride sulfoxide. The detailed mechanisms of reactions remain to be unclear. According to my analysis, it may be that it can prevent the thionyl chloride being decomposed into sulfur dichloride, sulfur dioxide and chlorine during the process of distillation. The detailed purification method is that: put together of 450 ml of thionyl chloride with 12.5g of sulfur powder for being heated under reflux for 4.5 hours, followed by efficient fractionating column for twice to obtain pure colorless. Alternatively, you can also apply distillation purification in the presence of triphenyl phosphite. The removed impurities should be sulfuryl chloride, sulfur monochloride and sulfur dichloride.
UsesThionyl chloride is an important intermediate of organic chemistry and is mainly used in medicine, pesticides, dyes and industrial organic synthesis industry as chlorinating agent. Consumption structure: the pharmaceutical industry accounted for 25%, pesticide industry accounted for 50%, dyestuff industry accounted for 5% and other industries accounted for 20%. The pesticide industry contributes the major part for consumption of thionyl chloride and is mainly used for the production of inabenfide, valerate, fenvalerate, mosquito-killing dimerthrin, flucythrinate, diflubenzuron, isocarbophos, fenpropathrin, endosulfan, deltamethrin, a (b) group chlorpyrifos, oxazolidinone, quizalofop and warfarin.
Because thionyl chloride can have fierce reaction with water, it is able to have reaction with metal chloride hydrated salt for production with anhydrous metal chlorides. MCln • xH2O + x SOCl2 → MCln + x SO2 + 2x HCl
Thionyl chloride was subjected heating reflux with a transition metal oxide and can further generate the corresponding oxychloride of the metal: WO3 + 2SOCl2 → WOCl4 + 2SO2
Thionyl chloride has been widely used for converting alcohol and the carboxylic acid into the corresponding acid chloride and chlorinated hydrocarbons. Compared with other agents (such as phosphorus penta-chloride), thionyl chloride is often the preferred reagents, because both the reaction product of sulfur dioxide and hydrogen chloride are gaseous and is easily to be separated. The excess amount of 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. Sulfoacid can react with thionyl chloride to generate sulfonyl chloride. Sulfinic acid can have reaction with thionyl chloride to generate sulfinyl chloride. Phosphonic acid can have reaction with thionyl chloride to generate phosphine chloride.
Thionyl chloride can react with mono-substituted formamide to generate the corresponding isonitriles. Amide can react with thionyl chloride to generate imine acyl chloride. Primary amide, upon co-heating with thionyl chloride, will be further dehydrated to become nitrile.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
Synthesis methodCurrently there are major approaches for industrial production of thionyl chloride including chlorosulfonic acid method, sulfur dioxide gas-phase method and phosphorus oxychloride cogeneration.
Fixed consumption amount:
Production methods raw material and specifications consumption quota/t • t-1
Chlorosulfonic acid method chlorosulfonic acid (95%) 1.1
Liquid chlorine (99%) 0.91
Sulfur powder (99.5%) 0.42
Fumed sulfur dioxide (99.5%) 0.22
Liquid chlorine (99%) 0.88
Sulfur dioxide (99%) 0.44
Cogeneration phosphorus oxychloride, phosphorus trichloride (98%) 1.3
Liquid chlorine (99%) 0.66
Sulfur dioxide (99%) 0.64
ToxicityThionyl chloride is toxic and is corrosive and has tearing property.
Pathways: inhaled, ingested, percutaneous absorption.
Health hazard: inhalation, oral administration or percutaneous absorption is harmful to our health. The eyes, skin, mucosa and respiratory tract have a strong stimulating effect and can cause burn wound. After inhalation, it may be lethal due to causing the spasm and dropsy of throat and bronchial. Poisoning performance includes burning sensation, coughing, wheezing, and dizziness, and laryngitis, shortness of breath, headache, nausea and vomiting.
Acute toxicity: LC50: 2435 mg/m3 (rat inhalation)
Irritation: a rabbit eyes: 1380 μg, severe stimulation.
Protective: This product can burn the skin and is irritable to the mucous membrane. During operation, the worker should wear protective equipment and should wash immediately with plenty of water if being splashed on skin.
First-aid
Skin contact: Immediately remove contaminated clothing, rinse with plenty of water for at least 15 minutes. Then go for medical treatment.
Eye contact: immediately lift up eyelid; wash with large flows of water or saline thoroughly for at least 15 minutes. Then go for medical treatment.
Inhalation: rapidly leave the scene to place with fresh air. Keep the airway open. If breathing is difficult, give oxygen. If breathing stops, immediately apply artificial respiration and send for medical treatment.
Ingestion: for misusage people, immediately rinse the mouth with water and drink milk or egg white. Then go for medical treatment.
How to deal with the wasted thionyl chloride so that the environment is not affectedIt is recommended for distillation recycling. If you want to deal with it, you can add it slowly into ice water for decomposition into SO2 and HCL which are subject to further treatment.
If the amount of the wasted thionyl chloride is large, you can consider recycle or sold outside for treatment. If the amount is small, you can add it drop wise into the alkaline water for decomposition and neutralization.
Packing and storagePackaging: glass or plastic barrels (tank) full open drums; glass or plastic bucket (cans); outside: the ordinary wooden box or wooden grille half; frosted glass bottles or threaded glass; outside: the ordinary wooden box; ampoules; outside: ordinary wooden box.
Storage precautions: for railway transport, it should be subject to package strictly in accordance with the dangerous cargo form in the <> (Ministry of railway of china). Upon the shipment, the packaging should be complete and the loading should be safe. During the process of transport, we should ensure that the container does not leak, does not fall off and does not been broken. It is not allowed to mix it with alkali or edible chemicals for operation and transport. During the transport, the transport vehicles should be equipped with spill response equipment. During the transport process, we should prevent sunshine exposure, rain and high temperature. During the road transport, the vehicles should be driven according to the provided routes with no stopping in residential areas and densely populated areas. It should be stored in a cool, ventilated warehouse with the storage temperature being not exceed 25 ℃ and the relative humidity being less than 75%. Keep the container closed. Moreover, we should store it separately from bases and avoid mixing for storage. Storage areas should be equipped with spill response equipment and suitable host materials.
Chemical PropertiesIt is colorless or light yellow volatile liquid with a strong suffocating odor. It can also be miscible with benzene, chloroform and carbon tetrachloride.
UsesIt can be applied to medicine, pesticide and dye industries and mainly used for the production of isocarbophos, sumicidin, propargite tetramisole hydrochloride, indomethacin, and vitamin A, etc.
It can be used as the chlorinating agents for organic synthesis such as chlorination of alcoholic hydroxyl group, chlorination of carboxylic acid, chlorination of acid anhydride and the chlorine displacement of organic sulfonic acid or carboxylic acid. It can also be used for making acyl chloride as well as being used for the manufacture of pharmaceutical intermediates such as tetramisole hydrochloride and synthomycin palmitate. It can also be used as a dehydrating agent or solvent.
Production methodIt can be produced with the reaction between sulfur trioxide and sulfur dichloride.
Chlorosulfonic acid method: first add sulfur powder to the reactor, put through the chlorine gas for reaction to generate sulfur monochloride. Then add a certain amount of chlorine acid and sulfur monochloride to the reactor; put through chlorine gas at below 50 ℃ for reaction; the resulted mixture was further subject to the crude distillation and condensation; further collect the material liquid below 130 ℃ and feed to the distillation pot; in order to make the low-boiling sulfur dichloride be convert to sulfur chloride for further being left in the pot, then you have to add 15% to 20% the amount of the crude product of sulfur and then send for distillation; reflux for 4h until giving normal color; collect the fraction between 75-80 ℃ to obtain the finished product. The reaction equation is:
2ClSO3H + S2C12 + C12 → 2SOC12 + 2SO2 + 2HCl
Sulfur dioxide method: take sulfur, liquid chlorine and liquid sulfur dioxide as raw material; apply whole-cycle and liquid circulation method for production of high-purity alumina thionyl chloride with a purity of 99%; this method has advanced technology, high product quality and releases less "three wastes".
Categorycorrosive materials
Toxicity gradinghighly toxic
Acute toxicityinhalation-rat LC50: 500 PPM/1 hour
Chemical PropertiesColorless to slightly yellow liquid
Flammability and hazard characteristicsirritation; meeting with water can emit toxic sulfur dioxide, hydrogen chloride, chlorine and other gases; thermal decomposition can generate toxic fumes of sulfur oxides and chlorides
Storage characteristicsTreasury ventilation low-temperature drying; and bases, food additives stored separately;
Extinguishing agentdry sand, dry powder; water ban
Professional standardsTWA 1 PPM (5 mg/cubic meter); STEL 1 PPM (5 mg/m3)
General DescriptionA colorless to yellow fuming liquid with a suffocating pungent odor. Boiling point 79°C. A lachrymator. Highly corrosive and toxic. Long-term inhalation of low concentrations or short-term inhalation of high concentrations has adverse health effects.
Reactivity ProfileThionyl chloride reacts, potentially explosively, with dimethyl sulfoxide or dimethylformamide containing traces of iron or zinc [Spitulnik, M. J., Chem. Eng. News, 1977, 55(31), p. 31]. Undergoes violent reactions with bases (ammonia, sodium hydroxide, potassium hydroxide, amines), alkali metals (sodium, potassium), esters (ethyl acetate), toluene mixed with ethanol / water [Bretherick, 5th ed., 1995, p. 1325]. Has an expansion ratio from gas to liquid of nearly 1000:1. Hence may cause an explosion if heated while contained [MCA Case History No. 1808]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Perchloric acid ignites on contact with sulfinyl chloride. (Bailar, 1973, Vol. 2, 1442). SOCl2 reacts with esters, such as ethyl acetate, forming toxic SO2 gas and water soluble/toxic acyl chlorides, catalyzed by Fe or Zn (Spagnuolo, C.J. et al. 1992. Chemical and Engineering News 70(22):2.).
Health HazardCORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Fire will produce irritating, corrosive and/or toxic gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control or dilution water may cause pollution.
Fire HazardEXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily. May ignite combustibles (wood, paper, oil, clothing, etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Flammable/toxic gases may accumulate in confined areas (basement, tanks, hopper/tank cars, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. Substance may be transported in a molten form.
Thionyl chloride Preparation Products And Raw materials
Preparation Products1-Naphthoyl chloride-->3-Thiophenecarbonyl chloride-->(2-FLUORO-PHENYL)-METHANESULFONYL CHLORIDE-->2-NITRO-ALPHA-TOLUENESULFONYL CHLORIDE-->METHYL 3-AMINOBENZOATE-->O-TOLYL-METHANESULFONYL CHLORIDE-->ETHYL 6-(HYDROXYMETHYL)PYRIDINE-2-CARBOXYLATE-->2-Naphthoyl chloride-->H-DL-PRO-OME HCL-->3,4,5-TRICHLOROTHIOPHENE-2-CARBONYL CHLORIDE-->ethyl 2-[2-(diethylamino)ethyl]acetoacetate -->ETHYL 2-ACETYLOXY-A-(1-HYDROXYETHYLIDENE)-B-OXOBENZENE PROPANOATE-->N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE-->CHLORDIMEFORM-->1-(1-2-HYDROXYPHENYL)ETHENYL)-1H-IMIDAZOLE-->ALPHA-ACETYL-2-HYDROXY-BETA-OXO-BENZENEPROPANOIC ACID MONO SODIUM SALT-->(2-HYDROXY-PHENYL)-ACETIC ACID METHYL ESTER-->NICLOFOLAN-->Reactive Turquoise Blue Kn-G-->QUINOLINE-2-CARBONYL CHLORIDE-->M-TOLYL-METHANESULFONYL CHLORIDE-->2,6-Pyridinedicarboxylic acid chloride-->Cyclopentanecarbonyl chloride-->Ethyl 6,8-dichloro caprylate-->5-Amino-2,4,6- triiodisophthaloyl acid dichloride-->2-(Chloromethyl)-5-propoxypyridine-->(2,5-DIMETHOXYPHENYL)ACETYL CHLORIDE-->3-Chloropropanesulfonyl chloride-->4,6-DIMETHOXYPYRIMIDINE-2-CARBONYL CHLORIDE-->4-Fluorophenylacetyl chloride-->3-(2-METHOXY-PHENYL)-PROPIONYL CHLORIDE-->M-TOLYL-ACETYL CHLORIDE-->2,3-DICHLOROPYRIDINE-5-CARBONYL CHLORIDE-->Z-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carbonyl chloride-->Cinnamamide-->4-Ethylbenzoyl chloride-->2-CHLOROETHYL METHYL SULFIDE-->1-PHENOXY-2-CHLOROPROPANE-->Ethyl 6,8-dichlorooctanoate-->(Chloromethylene)dimethyliminium chloride
Raw materialsChlorine-->Sulfur-->Chlorosulfonic acid-->Sulfur trioxide-->Disulfur dichloride-->Sulfur dichloride
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