Thionyl chloride химические свойства, назначение, производство
Химические свойства
Thionyl chloride is a pale yellow to reddish liquid. Suffocating odor like sulfur dioxide. Fumes form when exposed to moist air.
Физические свойства
Pale yellow to red fuming liquid; suffocating odor; refractive index 1.517 at 20°C; density 1.631 g/mL at 20°C; freezes at -101°C; boils at 75.6°C; decomposes at 140°C; decomposes in water; soluble in benzene, chloroform, and carbon tetrachloride.
Использование
Thionyl chloride (SOCl2) is used as a chlorinating agent in
manufacturing organic compounds. It is also used as a
solvent in high-energy lithium batteries.
Подготовка
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.
Определение
ChEBI: Thionyl chloride is a sulfinyl halide in which both of the halide atoms are chorines. It is a sulfinyl halide and a chlorine molecular entity.
Общее описание
Thionyl chloride appears as a 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.
Профиль реактивности
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.).
Опасность
Strong irritant to skin, tissue, and upper
respiratory tract.
Угроза здоровью
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.
Пожароопасность
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.
Профиль безопасности
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.
Возможный контакт
Thionyl chloride is used as specialty chlorinating agent, particularly in preparation of organic acid chlorides; in organic synthesis; as a catalyst.
Перевозки
UN1836 Thionyl chloride, Hazard class: 8; Labels: 8-Corrosive material.
Методы очистки
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.
Несовместимости
Reacts violently with water releasing sulfur dioxide and hydrogen chloride. Keep away from water, acids, alcohols, alkalis, ammonia, chloryl perchlorate.
Утилизация отходов
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.
Thionyl chloride препаратная продукция и сырье
сырьё
препарат
АЛЬФА-АЦЕТИЛ-2-ГИДРОКСИ-БЕТА-ОКСО-БЕНЗЕНПРОПАНОВАЯ КИСЛОТА МОНОНАТРИЯ
Хлорид циклопентанкарбонил
QUINOLINE-2-CARBONYL CHLORIDE
2,6-пиридиндикарбоновая кислота хлорид
1-ФЕНОКСИ-2-ХЛОРОПРОПАН
2,3-DICHLOROPYRIDINE-5-CARBONYL ХЛОРИД
Циннамамид
(хлорметилен)диметиламмоний хлорид
Reactive Turquoise Blue Kn-G
1-(1-2-HYDROXYPHENYL)ETHENYL)-1H-IMIDAZOLE
M-TOLYL-METHANESULFONYL CHLORIDE
(2-HYDROXY-PHENYL)-ACETIC ACID METHYL ESTER
Никлофолан
Хлорид 4-этилбензоил
H-DL-PRO-OME HCL
(2-метилфенил)метансульфанил хлорид
3,4,5-TRICHLOROTHIOPHENE-2-CARBONYL CHLORIDE
ЭТИЛ-2-АЦЕТИЛОКСИ-А-(1-ГИДРОКСИЭТИЛИДЕН)-В-ОКСОБЕНЗОЛА ПРОПАНОАТ
Метил 3-аминобензоа
Этил 6,8-дихлороктаноат
Хлорид 2-нафтоил
ETHYL 6-(HYDROXYMETHYL)PYRIDINE-2-CARBOXYLATE
3-Thiophenecarbonyl chloride
Z-cis-3-(2-chloro-3，3，3-trifluoro-1-propenyl)-2，2-dimethylcyclopropane carbonyl chloride
2-CHLOROETHYL METHYL SULFIDE
N, N-БИС (2-ХЛОРОЭТИЛ) -P-ТОЛУОЛСульфонамид
2-(Хлорметил)-5-пропоксипиридин
ХЛОРДИМЕФОРМ
Этил 6,8-дихлоркаприлат
3-хлорпропансульфонилхлорида
(2-фторфенил)метансульфанил хлорид
5-Amino-2,4,6-triiodoisophthaloyl dichloride
(2,5-DIMETHOXYPHENYL)ACETYL CHLORIDE
2-NITRO-ALPHA-TOLUENESULFONYL CHLORIDE
1-нафтoил хлорид
4-фторфенилацетил хлорид
3-(2-METHOXY-PHENYL)-PROPIONYL CHLORIDE
М-ТОЛИЛ-АЦЕТИЛХЛОРИД
4,6-DIMETHOXYPYRIMIDINE-2-CARBONYL CHLORIDE
ethyl 2-[2-(diethylamino)ethyl]acetoacetate
CARBETAPENTANE CITRATE