アセナフチレン 化学特性,用途語,生産方法
外観
黄色～褐色, 結晶～結晶性粉末又は塊
溶解性
エタノールに溶け、水にほとんど溶けない。
解説
C12H8(152.20)．アセナフチレンは，アセナフテンの蒸気を赤熱した酸化鉛(Ⅳ)の上を通して脱水素させると得られる．結晶．融点93 ℃，沸点103～105 ℃(400 Pa)．エタノール，エーテルなどに可溶．加熱すれば重合する．また，紫外線照射により二量体を与える．森北出版「化学辞典（第2版）
用途
有機合成原料。
用途
環境(大気)分析用標準品。
用途
染色原料、殺菌?殺虫剤、電子材料原料
説明
Acenaphthylene is a polycyclic aromatic hydrocarbon (PAH) consisting of three fused aromatic rings. It is used in the production of plastics and serves as an intermediate in the manufacture of dyes, soaps, pigments, pharmaceuticals, insecticides, fungicides, herbicides, and plant growth regulators. It is also a precursor to naphthalic acids, naphthalic anhydride (which is used in pigment production), and can be utilized in the synthesis of resins.
The largest emissions of PAHs originate from the incomplete combustion of organic matter during industrial processes and other human activities. Major sources include:
(a) the processing of coal, crude oil, and natural gas;
(b) coking, coal conversion, petroleum refining, and the production of carbon black, creosote, coal tar, and bitumen;
(c) aluminum, iron, and steel production in plants and foundries;
(d) heating in power plants and households, as well as cooking;
(e) combustion of waste;
(f) motor vehicle emissions;
(g) environmental tobacco smoke.
化学的特性
Acenaphthylene is a flaky yellow crystalline powder that forms prismatic or plate-like crystals. It is freely soluble in organic solvents such as ethanol, methanol, propanol, diethyl ether, petroleum ether, and benzene, but insoluble in water. Additionally, it polymerizes in the presence of strong acids.
物理的性質
Colorless to white prisms or crystalline plates from alcohol with an odor similar to coal tar or
aromatic hydrocarbons.
使用
Acenaphthylene has been used to investigate the photodimerization of acenaphthylene in micellar and hydrogel media.
定義
ChEBI: Acenaphthylene is a ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar. It is an ortho- and peri-fused polycyclic arene, a member of acenaphthylenes and an ortho- and peri-fused tricyclic hydrocarbon.
一般的な説明
Acenaphthylene is a colorless crystalline solid. Insoluble in water. Used in dye synthesis, insecticides, fungicides, and in the manufacture of plastics.
空気と水の反応
Insoluble in water.
反応プロフィール
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as ACENAPHTHYLENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.
健康ハザード
Acenaphthene is irritating to the skin and mucous membranes of rabbits. Subchronic oral administration of acenaphthene adversely affected the kidneys, liver, blood, reproductive system, and lungs in experimental animals. In rats, prolonged inhalation of low doses caused pulmonary effects such as bronchitis, pneumonia, and desquamation of the bronchial and alveolar epithelium.
安全性プロファイル
Moderately toxic by intraperitonealroute. Mutation data reported. When heated todecomposition it emits acrid smoke and irritating fumes.
職業ばく露
PAHs are compounds containing multiple benzene rings and are also called polynuclear aromatic hydrocarbons. Acenaphthylene is an aromatic hydrocarbon used in coal tar processing, as a dye intermediate; making insecticides, fungicides, plastics.
環境運命予測
Biological. When acenaphthylene was statically incubated in the dark at 25 °C with yeast
extract and settled domestic wastewater inoculum, significant biodegradation with rapid
adaptation was observed. At concentrations of 5 and 10 mg/L, 100 and 94% biodegradation,
respectively, were observed after 7 d (Tabak et al., 1981). A Beijerinckia sp. and a mutant strain
were able to cooxidize acenaphthylene to the following metabolites: acenaphthenequinone and a
compound tentatively identified as 1,2-dihydroxyacenaphthylene. When acenaphthylene was
incubated with a mutant strain (Beijerinckia sp. strain B8/36) one metabolite formed which was
tentatively identified as cis-1,2-acenaphthenediol (Schocken and Gibson, 1984). This compound
also formed when acenaphthylene was deoxygenated by a recombinant strain of Pseudomonas
aeruginosa PAO1(pRE695) (Selifonov et al., 1996).
Bossert and Bartha (1986) reported that acenaphthylene in a Nixon sandy loam soil (1
g/kg) completely disappeared in <4 months. They concluded volatilization was more important
than biodegradation in the disappearance of acenaphthylene from soil.
Ozonation in water at 60 °C produced 1,8-naphthalene dialdehyde, 1,8-
naphthalene anhydride, 1,2-epoxyacenaphthylene, 1-naphthoic acid, and 1,8-naphthaldehydic acid
(Calvert and Pitts, 1966).
輸送方法
UN3143 Dye intermediates, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material, Hazard, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
純化方法
Dissolve acenaphthylene in warm redistilled MeOH, filter through a sintered glass funnel and cool to -78o to precipitate the material as yellow plates [Dainton et al. Trans Faraday Soc 56 1784 1960]. Alternatively it can be sublimed in vacuo. [Beilstein 5 H 625, 5 IV 2138.]
不和合性
Keep away from ozone and strong oxidizing agents. 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
廃棄物の処理
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. Product residues and sorbent media may be packaged in epoxy-lined drums, then destroyed by incineration, permanganate oxidation or microwave plasma treatment. The United States Environmental Protection Agency has investigated chemical precipitation for wastewater treatment
アセナフチレン 上流と下流の製品情報
原材料
準備製品
4-アミノナフタルイミド
1-アセトキシアセナフテン
3,4,9,10-ペリレンテトラカルボン酸二無水物
1,2,2a,3,4,5-ヘキサヒドロアセナフチレン
3,9-ペリレンジカルボン酸
1,8,1',8',1'',8''-(1,2,3,4,5,6-ベンゼンヘキサイル)トリスナフタレン
アセナフチレン-1(2H)-オン
1-アセナフテノール
1-nitroacenaphthlene
Acenaphthylene, 5-nitro-
Acenaphthylene, 1,2-dihydro-1,2-dimethoxy-