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Пирролидин структурированное изображение

Пирролидин

  • английское имяPyrrolidine
  • CAS №123-75-1
  • CBNumberCB9852978
  • ФормулаC4H9N
  • мольный вес71.12
  • EINECS204-648-7
  • номер MDLMFCD00005249
  • файл Mol123-75-1.mol
химическое свойство
Температура плавления -63 °C
Температура кипения 87-88 °C/760 mmHg (lit.)
плотность 0.852 g/mL at 25 °C (lit.)
плотность пара 2.45 (vs air)
давление пара 128 mm Hg ( 39 °C)
показатель преломления n20/D 1.443(lit.)
FEMA 3523 | PYRROLIDINE
Fp 37 °F
температура хранения Store below +30°C.
растворимость water: miscible
форма Liquid
пка 11.27(at 25℃)
цвет Colorless to Almost colorless
Запах at 0.10 % in propylene glycol. ammoniacal animal egg amine
РН 12.9 (100g/l, H2O, 20℃)
Пределы взрываемости 1.6-10.6%(V)
Odor Type ammoniacal
Растворимость в воде Miscible with alcohol, ether, chloroform and water.
Чувствительный Air Sensitive
Мерк 14,8015
Номер JECFA 1609
БРН 102395
Диэлектрическая постоянная 8.3000000000000007
Стабильность Stable; flammable. Incompatible with strong acids, strong oxidizing agents.
ИнЧИКей RWRDLPDLKQPQOW-UHFFFAOYSA-N
LogP 0.22 at 25℃
Вещества, добавляемые в пищу (ранее EAFUS) PYRROLIDINE
Справочник по базе данных CAS 123-75-1(CAS DataBase Reference)
Рейтинг продуктов питания EWG 1
FDA UNII LJU5627FYV
Справочник по химии NIST Pyrrolidine(123-75-1)
Система регистрации веществ EPA Pyrrolidine (123-75-1)
больше
Заявления об опасности и безопасности
Коды опасности F,T,C
Заявления о рисках 11-22-23-34-35-20/21/22-20/22-R35-R20/21/22-R11
Заявления о безопасности 16-26-36/37/39-45-33-S45-S36/37/39-S26-S16
РИДАДР UN 1922 3/PG 2
WGK Германия 2
RTECS UX9650000
F 34
Температура самовоспламенения 653 °F
TSCA Yes
кода HS 2933 99 80
Класс опасности 3
Группа упаковки II
Банк данных об опасных веществах 123-75-1(Hazardous Substances Data)
Токсичность LD50 orally in Rabbit: 433 mg/kg
NFPA 704:
3
2 1

рисовальное письмо(GHS)

  • рисовальное письмо(GHS)

    GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms

  • сигнальный язык

    опасность

  • вредная бумага

    H302+H332:Вредно при проглатывании или при вдыхании.

    H314:При попадании на кожу и в глаза вызывает химические ожоги.

    H225:Легковоспламеняющаяся жидкость. Пары образуют с воздухом взрывоопасные смеси.

  • оператор предупредительных мер

    P210:Беречь от тепла, горячих поверхностей, искр, открытого огня и других источников воспламенения. Не курить.

    P280:Использовать перчатки/ средства защиты глаз/ лица.

    P301+P312:ПРИ ПРОГЛАТЫВАНИИ: Обратиться за медицинской помощью при плохом самочувствии.

    P303+P361+P353:ПРИ ПОПАДАНИИ НА КОЖУ (или волосы): Снять/удалить немедленно всю загрязненную одежду. Промыть кожу водой.

    P304+P340+P310:ПРИ ВДЫХАНИИ: Свежий воздух, покой. Немедленно 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.

Пирролидин химические свойства, назначение, производство

Химические свойства

Pyrrolidine appears as a colorless to pale yellow liquid with an ammonia-like odor. It is infinitely miscible with water and conventional organic solvents such as methanol, acetone, ether, and chloroform. It acts as a lachrymator.
Chemically, pyrrolidine behaves like a secondary amine in every respect. For example, it undergoes Leuckart –Wallach and Mannich reactions and is readily converted into an enamine. In the presence of a catalyst, such as platinum at 360°C or rhodium at 650°C, pyrrole is formed. In the presence of a copper catalyst, N-methylpyrrolidone is converted into N-methylpyrrolidine.

Физические свойства

Pyrrolidine has a penetrating amine-type odor, reminiscent of ammonia and piperidine. It is easy to turn yellow when exposed to light or humid air, easily soluble in water and ethanol. It is nauseating and diffusive.

Вхождение

Reported found in beer, bread, wheat bread, salmon caviar, fish, milk, leaves and stalks of celery, Camembert cheese, Limburger cheese, Russian cheeses, tilsit cheese, other cheeses, caviar, raw fatty fish, beer, Finnish whiskey, white wine, red wine, coffee, radish, malt, roasted peanut, sweet corn and roasted barley.

Использование

Pyrrolidine is a flammable alkaline liquid that undergoes reactions typical of secondary amines. It is used to prepare pesticides and rubber accelerators and as a chemical intermediate (usually the hydrochloride form) in the pharmaceutical industry. There is relatively limited industrial exposure to this material.

Определение

ChEBI: Pyrrolidine is a cyclic amine whose five-membered ring contains four carbon atoms and one nitrogen atom; the parent compound of the pyrrolidine family. It is a saturated organic heteromonocyclic parent, a member of pyrrolidines and an azacycloalkane. It is a conjugate base of a pyrrolidinium ion.

прикладной

Pyrrolidine is a heterocyclic compound used as a building block in the synthesis of wide range of pharmaceutical compounds, namely matrix metalloprotein inhibitors (MMPIs) and aminopeptidase N inhibitors (APNIs). It has been used for the synthesis of N-benzoyl pyrrolidine from benzaldehyde via oxidative amination. It may be used as a catalyst for the synthesis of N-sulfinyl aldimines from carbonyl compounds and sulfonamides.
Pyrrolidine can also be used to synthesize:
Taddol-pyrrolidine phosphoramidite, a ligand for rhodium-catalyzed [2+2+2] cycloaddition of pentenyl isocyanate and 4- ethynylanisole.
H,4 PyrrolidineQuin-BAM (′PBAM′), a selective catalyst for the aza-Henry addition of nitroalkanes to aryl aldimines.
1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline by reacting with o-aminobenzaldehyde.

Подготовка

Pyrrolidine is formed by reduction of pyrrole. Via overall 5-endo-trig cyclizations of homoallylic tosylamides. Pyrrolidine can be produced from butanediol and ammonia, e.g., over an aluminum thorium oxide catalyst at 300°C or over a nickel catalyst at 200°C and 20 MPa under hydrogenation conditions. It can also be produced from THF and ammonia over aluminum oxide at 275-375°C.

Общее описание

Pyrrolidine is a saturated heterocycliccompound having one nitrogenatom in a five-membered ring. It is a colorless to pale yellow liquid with an ammonia-like odor. It is found in certain plants andthe ring structure is present in manyalkaloids. Flash point 37°F. Density 0.85 g / cm3. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.

Реакции воздуха и воды

Highly flammable. Very soluble in water.

Профиль реактивности

Tetrahydro pyrrole neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. An explosion occurred when a mixture of Tetrahydro pyrrole, benzaldehyde, and propionic acid was heated in an attempt to form porphyrins.

Опасность

Flammable, dangerous fire risk. Toxic by ingestion and inhalation.

Угроза здоровью

The acute toxicity of pyrrolidine is moderateon test animals. It is somewhat less toxicthan pyrrole. The vapors are an irritant tothe eyes and respiratory tract. The liquid iscorrosive to the skin. Contact with the eyescan cause damage. The oral LD50 value inrats is 300 mg/kg, while the inhalation LC50value in mice is 1300 mg/m3/2 h (NIOSH1986).

Пожароопасность

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Профиль безопасности

Poison by ingestion and intravenous routes. Moderately toxic by inhalation. Dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits hghly toxic fumes of NOx.

Методы очистки

Dry pyrrolidine with BaO or sodium, then fractionally distil it, under N2, through a Todd column (p 11) packed with glass helices. [Beilstein 20 H 159, 20 I 36, 20 II 79, 20 III/IV 2072, 20/1 V 162.]

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