7719-09-7 Usage
Chemical Description
Thionyl chloride is a colorless to yellowish liquid that is used as a chlorinating agent.
Chemical Description
Thionyl chloride is a reactive chemical used as a chlorinating agent.
Chemical Description
Thionyl chloride is an inorganic compound used as a chlorinating agent.
Chemical Description
Thionyl chloride is used to convert the acids into ethyl esters.
Chemical Description
Thionyl chloride is used to generate the acid chloride for the amidation step, and mCPBA is used to oxidize the acylanilide to the sulfone.
Chemical Description
Thionyl chloride is used for the synthesis of 1,1'-sulfinylditriazole.
Chemical Description
Thionyl chloride is used to convert the carboxylic acids into acid chlorides.
Uses
Thionyl chloride is an important intermediate in organic chemistry and is widely used in various industries due to its versatile reactivity. It is primarily used as a chlorinating agent in the production of various organic compounds.
Used in Pharmaceutical Industry:
Thionyl chloride is used as a chlorinating agent for the synthesis of pharmaceutical intermediates such as tetramisole hydrochloride and synthomycin palmitate. It is also used in the production of isocarbophos, sumicidin, propargite, and vitamin A.
Used in Pesticide Industry:
Thionyl chloride is extensively used in the pesticide industry, accounting for 50% of its consumption. It is utilized for the production of inabenfide, valerate, fenvalerate, mosquito-killing dimerthrin, flucythrinate, diflubenzuron, isocarbophos, fenpropathrin, endosulfan, deltamethrin, a (b) group chlorpyrifos, oxazolidinone, quizalofop, and warfarin.
Used in Dye Industry:
In the dyestuff industry, thionyl chloride is used for the synthesis of various dyes, accounting for 5% of its consumption.
Used in Industrial Organic Synthesis:
Thionyl chloride is used as a chlorinating agent in the industrial organic synthesis industry, accounting for 20% of its consumption.
Used in Lithium Battery Manufacturing:
Thionyl chloride is used as a solvent in high-energy lithium batteries.
Used in Herbicide Synthesis:
It is also used in the synthesis of herbicides, surfactants, drugs, vitamins, and dyestuffs.
Used in Organic Synthesis:
Thionyl chloride is widely used for converting alcohols and carboxylic acids into the corresponding acid chlorides and chlorinated hydrocarbons. It is often the preferred reagent due to the gaseous nature of the reaction products, sulfur dioxide and hydrogen chloride, which are easily separated. The excess thionyl chloride can be removed by distillation.
Used as a Dehydrating Agent or Solvent:
Thionyl chloride can also be used as a dehydrating agent or solvent in various chemical reactions.
Outline
Thionyl 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.
Purification
Thionyl 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.
Synthesis method
Currently 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
Toxicity
Thionyl 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 affected
It 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 storage
Packaging: 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.
Production method
It 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".
Professional standards
TWA 1 PPM (5 mg/cubic meter); STEL 1 PPM (5 mg/m3)
Preparation
Sulfurous oxychloride can be prepared by oxidation of sulfur dichloride with sulfur trioxide: SCl2 + SO3 → SOCl2 + SO2 Also, the compound can be prepared by reacting sulfur dioxide with phosphorus pentachloride: SO2 + PCl5 → SOCl2 + POCl3.
Reactivity Profile
Thionyl 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.).
Hazard
Strong irritant to skin, tissue, and upper
respiratory tract.
Health Hazard
CORROSIVE 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 Hazard
EXCEPT 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.
Flammability and Explosibility
Nonflammable
Safety Profile
Moderately toxic by
inhalation. The material itself is more toxic
than sulfur dioxide. Has a pungent odor
similar to that of sulfur dioxide; it fumes
upon exposure to air. Violent reaction with
water releases hydrogen chloride and sulfur
dioxide. Both these decomposition products
constitute serious toxicity hazards. A
corrosive irritant that causes burns to the
skin and eyes. A powerful chlorinating
agent. Potentially explosive reaction with
ammonia, bis(dimethy1amino)sulfoxide -
(above 80℃), chloryl perchlorate, 1,2,3-
cyclohexanetrione trioxime + sulfur dioxide,
dimethyl sulfoxide, hexafluoroisopropylideneaminolithium.
Violent reaction or
ignition with 2,4-hexadiyn-1-6-di01, onitrobenzoyl
acetic acid, o-nitrophenylacetic
acid, sodum (ignites at 300℃).
Incompatible with ammonia, dimethyl
formamide + trace iron or zinc, linseed oil +
quinoline, toluene + ethanol + water. When
heated to decomposition it emits toxic
fumes of SOx and Cl-. See also
HYDROGEN CHLORIDE and SULFUR
DIOXIDE.
Potential Exposure
Thionyl chloride is used as specialty chlorinating agent, particularly in preparation of organic acid chlorides; in organic synthesis; as a catalyst.
Shipping
UN1836 Thionyl chloride, Hazard class: 8; Labels: 8-Corrosive material.
Purification Methods
Crude SOCl2 can be freed from sulfuryl chloride, sulfur monochloride and sulfur dichloride by refluxing it with sulfur and then fractionally distilling twice. [The SOCl2 is converted to SO2 and sulfur chlorides. The S2Cl2 (b 135.6o) is left in the residue, whereas SCl2 (b 59o) passes over in the forerun.] The usual purification is to distil it from quinoline (50g SOCl2 to 10g quinoline) to remove acid impurities, followed by distillation from boiled linseed oil (50g SOCl2 to 20g of oil). Precautions must be taken to exclude moisture. Thionyl chloride is used extensively in organic syntheses and can be prepared by distillation of technical SOCl2 in the presence of diterpene (12g/250mL SOCl2), and avoiding overheating. Further purification is achieved by redistillation from linseed oil (1-2%) [Rigby Chem Ind (London) 1508 1969]. Gas chromatographically pure material is obtained by distillation from 10% (w/w) triphenyl phosphite [Friedman & Wetter J Chem Soc (A) 36 1967, Larsen et al. J Am Chem Soc 108 6950 1986]. HARMFUL VAPOURS.
Incompatibilities
Reacts violently with water releasing sulfur dioxide and hydrogen chloride. Keep away from water, acids, alcohols, alkalis, ammonia, chloryl perchlorate.
Waste Disposal
Spray on a thick layer of a (1:1) mixture of dry soda ash and slaked lime behind a shield. After mixing, spray water from an atomizer with great precaution. Transfer slowly into a large amount of water. Neutralize and drain into the sewer with sufficient water.
Check Digit Verification of cas no
The CAS Registry Mumber 7719-09-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,7,1 and 9 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 7719-09:
(6*7)+(5*7)+(4*1)+(3*9)+(2*0)+(1*9)=117
117 % 10 = 7
So 7719-09-7 is a valid CAS Registry Number.
InChI:InChI=1/Cl2OS/c1-4(2)3
7719-09-7Relevant articles and documents
The ultraviolet spectra of matrix isolated disulfur monoxide and sulfur dioxide
Phillips, L.F,Smith, J.J,Meyer, B
, p. 230 - 243 (1969)
The absorption spectrum of disulfur monoxide was observed in matrices at 20°K. All 18 observed bands of the (0, 0, ν3) - (0, 0, 0) progression fit the equation G(ν3′) = 29 070 + 426 (ν3′ + 1 2) - 4.80 (ν3′ + 1 2)2 + 0.075 (ν3′ + 1 2)3. The matrix data was used to reassign the reported gas-phase data and to deduce ν2′ and ν2″. The absorption spectrum of sulfur dioxide in a krypton matrix at 20°K is tentatively assigned to a progression A(ν1, ν2, 0) ← X(0, 0, 0). The SO2 a-X phosphorescence, excited by absorption of light in either the C or A system, is strongly enhanced in the matrix. T00, ν1 and ν2 shifts are listed for solid argon, krypton, xenon, nitrogen, methane, SF6, and C4F8. The phosphorescence intensity is strongly temperature dependent. The temperature-intensity curves are consistent with an energy transfer model involving interaction of the SO2 triplet state with the lattice vibration.
7H-pyrrolo[2,3-d]pyrimidine derivatives
-
, (2008/06/13)
The invention relates to 7H-pyrrolo[2,3-d]pyrimidine derivatives of formula I wherein the symbols and substituents are as defined in the description, to processes for the preparation thereof, to pharmaceutical compositions comprising such derivatives and to the use of such derivatives—alone or in combination with one or more other pharmaceutically active compounds—for the preparation of pharmaceutical compositions for the treatment especially of a proliferative disease, such as a tumour.
Hydroxamic acid derivatives as proteinase inhibitors
-
, (2008/06/13)
Compounds of formula (I) are matrix metalloprotemase inhibitors wherein X represents a carboxylic acid group —COOH, or a hydroxamic acid group —CONHOH;R2represents a radical of formula (II): R3—(ALK)m—(Q)p—(ALK)n., and W represents a cyclic amino radical of formula (IIIA) or (IIIB):
Method for the preparation of 2-chloro sulfinyl azetidinones
-
, (2008/06/13)
An improved method for the preparation of 2-chloro sulfinyl azetidin-4-one of the formula: STR1 wherein R is: hydrogen; C1 -C3 alkyl; halomethyl; cyanomethyl; phenyl; substituted phenyl; phenoxy, benzyloxy- or substituted benzyl; a group of the formula R2 --O--wherein R2 is t-butyl, 2,2,2-trichloroethyl, benzyl or substituted benzyl; a group of the formula R3 --(O)n --CH2 wherein R3 is phenyl or substituted phenyl. The 2-chlorosulfinylazetidin-4-one is prepared by reacting a penicillin sulfoxide ester of the general formula STR2 wherein R and R1 have the meanings defined above with an N-chloro halogenating agent in an inert organic solvent. The reaction is carried out in the presence of an acid scavenging amount of a phosphate or hydrogen phosphate of an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or mixtures thereof. These compounds find application as intermediates in the production of cefaclor which are powerful anti-bacterial compounds.
Synthesis, Crystal Structure, and Properties of 1,1,3,3,3-Pentaamino-1-oxo-1λ5,3λ 5-diphosphaz-2-ene, (NH2)2(O)P-N=P(NH2)3
Stock,Schnick
, p. 1079 - 1083 (2007/10/03)
Coarse crystalline (NH2)2(O)P-N=P(NH2)3 is obtained from a NH3 saturated CH2Cl2 suspension of (NH2)2(O)P-N=P(NH2)3·NH 4Cl at room temperature. (NH2)2(O)P-N=P(NH2)3·NH 4Cl is synthesized by slow addition of Cl2(O)P-N=PCl3 to a solution of NH3 in CH2Cl2 at -78 °C. Excess NH4Cl is removed by treatment with HNEt2 followed by extraction with CH2Cl2. The crystal structure of (NH2)2(O)P-N=P(NH2)3 has been determined by single crystal X-ray methods (P21/c; a = 1462.8(3) b = 944.8(2), c = 1026.9(2) pm, β= 110.69(3)°; Z = 8). In the unit cell there are two crystallographically unique molecules. They form a three dimensional network by intermolecular hydrogen bonding interactions (N-H...N ≥ 313 pm, N-H-...O ≥ 293 pm). The investigation of the thermal properties shows decomposition with evolution of NH3 above 80°C.
Silicate compounds for DNA purification
-
, (2008/06/13)
The present invention relates to a silicon-containing material which exhibits sufficient hydrophilicity and sufficient electropositivity to bind DNA from a suspension containing DNA and permit elution of the DNA from the material. Generally, the hydrophilic and electropositive characteristics are expressed at the surface of the silicon-containing material. Preferred silicon-containing materials of the present invention include boron silicate, aluminum silicate, phosphosilicate, silica carbonyl, silica sulfonyl and silica phosphonyl. The silicon-containing materials of the present invention are particularly useful in processes for purification of DNA from other cellular components. In these processes, a suspension of cellular components is placed in contact with the silicon-containing material, the silicon-containing material is washed to remove all cellular components other than DNA which are bound to the material, and the bound DNA is eluted from the material. Several of the silicon-containing materials are capable of binding and eluting DNA using only water.
Sulfonamides of phenylalkylamines or phenoxyalkylamines processes for their preparation and medicaments containing these compounds
-
, (2008/06/13)
Compounds of the formula I STR1 in which R1 signifies an aryl, aralkyl or an aralkenyl group, the aryl radical of which can, in each case, be substituted one or more times by halogen, cyano, alkyl, trifluoromethyl, alkoxy, alkylthio, trifluoromethoxy, hydroxyl or carboxyl, m a whole number from 1 to 3, n a whole number from 1 to 5, R2 hydrogen, an alkyl, aralkyl or acyl group, Q a bond or an oxygen atom, R3 hydrogen or a lower alkyl radical which is possibly terminally substituted by carboxyl or by a hydroxyl group and R4 hydrogen, a lower alkyl group with 1-4 C-atoms, which is possibly terminally substituted by carboxyl or hydroxyl, a possibly substituted phenyl, heteroaryl, cycloalkyl or acyl group or a group STR2 in which R5 represents a straight-chained or branched alkyl chain with 1-4 C-atoms which is possibly terminally substituted by carboxyl, alkoxycarbonyl, aminocarbonyl, hydroxyl, mercapto, alkylthio or imidazolyl and Y a carboxyl, an alkoxycarbonyl, aminocarbonyl or cyano, formyl, hydroxymethyl, aminomethyl or ortho ester group, whereby R3 and R4 can also be component of a 5- or 6-membered saturated or unsaturated possibly substituted heterocycle with 1-4 heteroatoms which can be annellated with further ring compounds via one or more bonds, as well as their salts, esters and amides, processes for their preparation and medicaments with thromboxane-antagonistic action which contain these compounds.
5-azolylacetoxymilbemycins as ecto- and endoparasites
-
, (2008/06/13)
The present invention relates to milbemycin derivatives of the formula I STR1 wherein X is hydrogen or β-halogen, R is methyl, ethyl, isopropyl or sec-butyl and Az is a 5 membered heterocyclic aromatic ring which contains 2-4 nitrogen atoms and is attached in the 1-position and which is unsubstituted or substituted by one or two C1 -C6 alkyl groups. These compounds, and the acid addition salts and metal complexes thereof, are effective pesticides for controlling endo-and ectoparasites, especially for controlling neamatodes which are parasites of animals. The may be obtained by appropriate esterification in 5-position of milbemycin derivatives. The selective β-halogenation of 14,15-epoxymilbemycin derivatives can be effected via the intermediate Δ13,14 -15-hydroxymilbemycins with appropriate halogenating agents.
THE LOWER OXIDES OF SULFUR AND RELATED ORGANIC SULFOXIDES
Steudel, Ralf
, p. 33 - 64 (2007/10/02)
The preparation, structures, spectra and other properties of organic sulfane oxides, R2SnO (n = 3,4), and dioxides, R2SnO2 (n = 3,4), as well as of the homocyclic sulfur oxides SnO (n=6...10) and SnO2 (n = 7,12) are discussed.All compounds are sulfoxides and contain two or more homonuclear S-S bonds.
Reversible Isomerization of Cyclo-octasulfur Monoxide; Preparation and X-Ray Crystal Structure of S8O*SbCl5
Steudel, Ralf,Sandow, Torsten,Steidel, Juergen
, p. 180 - 181 (2007/10/02)
The reaction of S8O and SbCl5 in CS2 gave S8O*SbCl5 (71percent yield) which was shown by X-ray crystallography to contain S8O in an isomeric conformation compared with pure S8O which can be recovered from the adduct in its usual conformation by recrystall
