1,4-Нафтохинон химические свойства, назначение, производство
Химические свойства
1,4-Naphthoquinone is a yellow to greenish yellow crystalline solid that has pungent odor like benzoquinone. It is slightly soluble in water, soluble in ether, chloroform, benzene, glacial acetic acid. In alkaline solutions it produces a reddish-brown color.
Использование
1,4-Naphthoquinone is used as a strong dienophile in Diels-Alder reaction. It is also used as a precursor to anthroquinone and 5-nitro-1,4-naphthalenedione, which finds application in the preparation of aminoanthroquinone and is also used as a dye precursor. It is a basic component of Vitamin K.
Определение
ChEBI: 1,4-naphthoquinone is the parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties. It derives from a hydride of a naphthalene.
Общее описание
Yellow needles or brownish green powder with an odor of benzoquinone.
Реакции воздуха и воды
Insoluble in water.
Профиль реактивности
1,4-Naphthoquinone may react with many acids and bases liberating heat and flammable gases (e.g., H2). The heat may be sufficient to start a fire in the unreacted portion of the ketone. May react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. May react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Опасность
Irritant
Угроза здоровью
ACUTE/CHRONIC HAZARDS: When heated to decomposition 1,4-Naphthoquinone emits toxic fumes and smoke.
Пожароопасность
Flash point data for 1,4-Naphthoquinone are not available; however, 1,4-Naphthoquinone is probably combustible.
Профиль безопасности
Poison by ingestion,
intravenous, subcutaneous, and
intraperitoneal routes. Experimental
reproductive effects. Questionable
carcinogen with experimental tumorigenic
data. When heated to decomposition it
emits acrid smoke and irritating fumes.
Синтез
1,4-Naphthoquinone is prepared by reacting naphthalene with molecular oxygen in a gaseous phase in the presence of a catalyst containing vanadium.
Prior to reacting the naphthalene with oxygen, the catalyst is pre-treated with molecular oxygen at 300° to 400° C in the absence of organic compounds and immediately thereafter a gas mixture containing naphthalene and molecular oxygen is passed over the pretreated catalyst at temperatures in the range of 300° to 400° C. The catalyst pre-treatment can be carried out in the presence of water vapor and the subsequent reaction of naphthalene with molecular oxygen can also be carried out in the presence of water vapor.
Возможный контакт
1,4-Naphthoquinone is used as a polymerization
regulator for rubber and polyester resins; in the
synthesis of dyes and pharmaceuticals; and as a fungicide
and algicide.
Перевозки
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
Методы очистки
Crystallise the quinone from diethyl ether (charcoal). It distils in steam. It also crystallises from *benzene or aqueous EtOH and sublimes in a vacuum. [Beilstein 7 IV 2422.]
Несовместимости
Ketones are incompatible with oxidizers
(chlorates, nitrates, peroxides, permanganates, perchlorates,
chlorine, bromine, fluorine, etc.); contact may cause fires
or explosions. Keep away from alkaline materials, strong
bases, strong acids, oxoacids, epoxides, nitrated amines,
azo, diazo, azido compounds, carbamates, organic cyanates.
May react with many acids and bases liberating heat and
flammable gases (e.g., hydrogen) generating heat may be
sufficient to start a fire in the unreacted portion of the
ketone. May react with reducing agents such as hydrides,
alkali metals, and nitrides to produce flammable gas
(e.g., hydrogen) and heat. Incompatible with isocyanates,
aldehydes, cyanides, peroxides, and anhydrides. May react
violently with aldehydes.
Утилизация отходов
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal.
1,4-Нафтохинон препаратная продукция и сырье
сырьё
препарат
Нильский красный
2-гидрокси-1 ,4-нафтохинона
2,3-дихлор-1 ,4-нафтохинона
Atovaquone
Натрий силикат
2,3-DIMETHYLANTHRAQUINONE
3,3'-Dichlorobenzidine dihydrochloride
2-Chloro-1,4-naphthoquinone
1H-[1]-BENZAZEPHE-2,5(3H, 4H)-DIONE
4-метокси-1-нафтол
2-HYDROXYANTHRAQUINONE
1,4-Dihydroxynaphthalene
MFCD00666862
1,4-Naphthalenedione, 2-chloro-3-[[4-(1,1-dimethylethyl)cyclohexyl]methyl]-
4-МЕТОКСИ-2-ФЕНИЛАЗО-1-НАФТОЛ