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Малононитрил структурированное изображение

Малононитрил

  • английское имяMalononitrile
  • CAS №109-77-3
  • CBNumberCB2259712
  • ФормулаC3H2N2
  • мольный вес66.06
  • EINECS203-703-2
  • номер MDLMFCD00001883
  • файл Mol109-77-3.mol
химическое свойство
Температура плавления 30-32 °C (lit.)
Температура кипения 220 °C (lit.)
плотность 1.049 g/mL at 25 °C (lit.)
давление пара 1 hPa (50 °C)
показатель преломления 1.4150
Fp 234 °F
температура хранения 2-8°C
растворимость 133g/l
пка 11(at 25℃)
форма Crystalline Low Melting Mass
цвет White to yellow-brown
Удельный вес 1.049
РН pH : 4.5
Растворимость в воде 13.3 g/100 mL (20 ºC)
Мерк 14,5711
БРН 773697
Пределы воздействия TLV-TWA 8 mg/m3 (3 ppm) (NIOSH).
Диэлектрическая постоянная 46.0
ИнЧИКей CUONGYYJJVDODC-UHFFFAOYSA-N
Справочник по базе данных CAS 109-77-3(CAS DataBase Reference)
Рейтинг продуктов питания EWG 1-4
FDA UNII EBL1KKS93J
Справочник по химии NIST Malononitrile(109-77-3)
Система регистрации веществ EPA Malononitrile (109-77-3)
больше
Заявления об опасности и безопасности
Коды опасности T,N
Заявления о рисках 23/24/25-50/53
Заявления о безопасности 23-27-45-60-61
РИДАДР UN 2647 6.1/PG 2
OEB B
OEL TWA: 3 ppm (8 mg/m3)
WGK Германия 3
RTECS OO3150000
F 8
Температура самовоспламенения 365 °C
TSCA Yes
Класс опасности 6.1
Группа упаковки II
кода HS 29269090
Банк данных об опасных веществах 109-77-3(Hazardous Substances Data)
Токсичность LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel)
NFPA 704:
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рисовальное письмо(GHS)

  • рисовальное письмо(GHS)

    GHS hazard pictogramsGHS hazard pictograms

  • сигнальный язык

    опасность

  • вредная бумага

    H319:При попадании в глаза вызывает выраженное раздражение.

    H317:При контакте с кожей может вызывать аллергическую реакцию.

    H410:Чрезвычайно токсично для водных организмов с долгосрочными последствиями.

    H300:Смертельно при проглатывании.

    H311+H331:Токсично при попадании на кожу или при вдыхании.

  • оператор предупредительных мер

    P273:Избегать попадания в окружающую среду.

    P280:Использовать перчатки/ средства защиты глаз/ лица.

    P301+P310:ПРИ ПРОГЛАТЫВАНИИ: Немедленно обратиться за медицинской помощью. Прополоскать рот.

    P302+P352+P312:ПРИ ПОПАДАНИИ НА КОЖУ: Промыть большим количеством воды. Обратиться за медицинской помощью при плохом самочувствии.

    P304+P340+P311:ПРИ ВДЫХАНИИ: Свежий воздух, покой. Обратиться за медицинской помощью.

    P305+P351+P338:ПРИ ПОПАДАНИИ В ГЛАЗА: Осторожно промыть глаза водой в течение нескольких минут. Снять контактные линзы, если Вы ими пользуетесь и если это легко сделать. Продолжить промывание глаз.

Малононитрил химические свойства, назначение, производство

Описание

Malonitrile, also known as Malononitrile, is an aliphatic nitrile that can release cyanide through chemical or biological transformation. It was also used decades ago for treating certain forms of mental illness.

Химические свойства

Malononitrile is a white powder or colorless, odorless crystalline substance. It may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.

Использование

Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamin (vitamin B1), pesticides dyestuffs for color photography and synthetic fibers (e.g. vinylidene cyanide). Product Data Sheet

Определение

ChEBI: Malononitrile is a dinitrile that is methane substituted by two cyano groups. It is a dinitrile and an aliphatic nitrile.

Методы производства

Malononitrile can be synthesized by a continuous method where preheated acetonitrile and cyanogen chloride are introduced into a tube reactor until the reaction mixture reaches a temperature of about 780°C. Another way to prepare malononitrile is by reacting phosphorus pentachloride with cyanoacetamide, or by using phosphorus pentoxide to react with malonamide or cyanoacetamide.
DOI: 10.15227/orgsyn.010.0066

Общее описание

A white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.

Реакции воздуха и воды

Soluble in water.

Профиль реактивности

Malononitrile is a white, low-melting powder (m. p. 30.5° C), toxic, combustible. Violent polymerization on contact with strong bases (sodium hydroxide, potassium hydroxide) or when heated above 130° C. When stored at 70-80° C for 2 months, spontaneous explosion (decomposition) occurred [Bretherick, 5th ed., 1995, p. 394].

Опасность

Toxic by ingestion and inhalation.

Пожароопасность

When heated to decomposition, Malononitrile emits highly toxic fumes (cyanide). May polymerize violently on prolonged heating. Avoid heat. Hazardous polymerization may occur, at prolonged heating at 266F or contact with strong bases at lower temperatures.

Промышленное использование

Malononitrile is used primarily as an intermediate in the synthesis of drugs and vitamins (thiamine). It has also been employed in the manufacture of photosensitizes, acrylic fibers and dyestuffs and as an oil-soluble polar additive in lubricating oil.
Malononitrile was used formerly in treatment of various forms of mental illness such as alteration of psychic functions and schizophrenic disorders.

Профиль безопасности

Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. A severe eye irritant. Combustible when exposed to heat or flame. Polymerizes violently when heated to 130°C or on contact with strong base. May spontaneously explode when stored at 70-80°C. To fight fire, use water, fog, spray, foam. When heated to decomposition it emits toxic fumes of NOx and CN-. See also NITRILES.

Экологическая судьба

When heated to decomposition, nitriles may release cyanide. Malonitrile appears to decompose rapidly in contact with soil and sediment.

Метаболизм

The in vitro metabolsim of malononitrile has been described by Stern et al. In the presence of thiosulphate, brain, liver and kidney slices metabolized malononitrile to thiocyanate. The formation of thiocyanate from malononitrile and thiosulphate was greatest in the presence of liver slices, lowest in brain, and intermediate with kidney slices. The liver enzyme system was saturated at a concentration of 3.3 mM malononitrile and a pH optimum of 7.0. This enzyme system was inhibited by cysteine and glutathione and inactivated by boiling. Stern et al indicated that thiosulphate increased cyanide and thiocyanate formed from malononitrile in tissue slices.

Методы очистки

Crystallise the nitrile from water, EtOH, *benzene or chloroform. Distil it in a vacuum from, and store over, P2O5. [Bernasconi et al. J Am Chem Soc 107 7692 1985, Gratenhuis J Am Chem Soc 109 8044 1987, Beilstein 2 IV 1892.]

Несовместимости

Incompatible with strong bases. May polymerize violently on prolonged heating @ 129C, or in contact with strong bases at lower temperatures. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

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