1,3-ジクロロベンゼン 化学特性,用途語,生産方法
外観
無色～わずかにうすい黄色, 澄明の液体
性質
m-体はCAS番号541-73-1、無色透明の液体で、匂いのデータはありません。引火性は低いですが、エアロゾルとおよびとの接触により爆発の危険性があります。
融点・凝固点は-24.8℃、沸点、初留点および沸騰範囲は173℃、引火点は63℃ (密閉式) です。m-体は吸引すると有害で、呼吸器への刺激の危険性があるため、グローブボックスや局所排気など換気の良い環境で取り扱います。
溶解性
水に不溶 (83mg/L水), エタノール, エーテルに可溶。エタノール及びジエチルエーテルに極めて溶けやすく、水にほとんど溶けない。
解説
ジクロロベンゼンの異性体の一つ。無色の板状結晶。衣類の防虫剤や殺虫剤として広く用いられる。化学式C6H4Cl2 1,3-ジクロロベンゼン。p-DCB。染料合成の中間体にも用いられるが、強力な衣服用の防虫剤として広く用いられている。小学館 デジタル大辞泉について 情報 | 凡例
用途
有機溶媒、医薬?染料中間体 (化学工業日報社)
物理的性質
1,3-Dichlorobenzene is a clear, colorless liquid with a disinfectant or musty-type odor. Soluble in alcohol, ether, insoluble in water. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 170 and 177 μg/L, respectively. At 25 °C, the lowest concentration at which a taste was detected was 190 μg/L, respectively (Young et al., 1996).
使用
1,3-Dichlorobenzene is used in organic synthesis that can synthesize fungicides imazalil, propiconazole, epiconazole, and insecticides insectaphos. It is also used in the synthesis of 1,2-diaminobenzene, in addition, it is also used as a solvent in the fields of dyes, medicine, resin, rubber and so on.
使用
1,3-Dichlorobenzene is used in medicine, and dyes. And it is also used to study the effect of solvent vapor pressure on the vertical nanowire of C60 molecules1. 1,3-Dichlorobenzene, a chlorinated aromatic hydrocarbon, can be detected in environmental samples using an advanced Fourier transform infrared spectroscopy-attenuated total reflectance (FTIR-ATR) sensor.
定義
ChEBI: 1,3-dichlorobenzene is a dichlorobenzene carrying chloro substituents at positions 1 and 3. Used as a fumigant, insecticide, and chemical intermediate.
製造方法
1,3-Dichlorobenzene is prepared from o-chloroaniline through diazotization and displacement reaction.
Add o-chloroaniline and hydrochloric acid into the reaction pot, mix evenly below 25°C, cool to 0°C, drop in sodium nitrite solution, control the temperature at 0-5°C, stop adding when the potassium iodide starch indicator turns blue, and obtain diazonium salt solution. Then add the diazonium salt solution into the hydrochloric acid solution of cuprous chloride at 0～5℃, stir well, heat up to 60～70℃ and react for 1h, after cooling, let stand for stratification, and use 5% sodium hydroxide for the oil layer. Repeated washing with water, dehydration with anhydrous calcium chloride, fractional distillation, and collection of fractions at 177-183 °C to obtain the product 1,3-dichlorobenzene.
一般的な説明
Colorless liquid. Sinks in water.
空気と水の反応
1,3-Dichlorobenzene is sensitive to moisture. Insoluble in water.
反応プロフィール
1,3-Dichlorobenzene is incompatible with oxidizing agents and aluminum and its alloys. Above the flash point, explosive vapor-air mixtures may be formed.
健康ハザード
INHALATION: Causes headache, drousiness, unsteadiness. Irritating to mucous membranes. EYES: Severe irritation. SKIN: Severe irritation. INGESTION: Irritation of gastric mucosa, nausea, vomiting, diarrhea, abdominal cramps and cyanosis.
火災危険
Special Hazards of Combustion Products: Irritating vapors including hydrogen chloride are produced.
使用用途
m-ジクロロベンゼンは、農薬や染料、顔料、医薬の合成中間体として用いられています。
取扱方法
取り扱う際は、適切な呼吸器保護具、保護手袋、保護眼鏡 (普通眼鏡型、側板付き普通眼鏡型、ゴーグル型) を着用して作業します。また、o-体は皮膚および身体への接触を避けるため、適切な保護衣のほか、顔面用保護具、長靴の着用が推奨されています。
作業場所は洗眼器と安全シャワーを設置し、全体換気または局所排気のある環境で作業を行います。
保管方法
炎および熱などから離して保管し、酸化剤との接触を避けます。容器は密閉し、換気の良い冷所で保管します。
応急措置
吸入した場合、気分が悪くなった際は、医師の診断、手当てを受けます。皮膚に付着した場合は、大量の水で洗浄し、症状が継続する場合は医師に連絡します。眼に入った場合は、水で15−20分間注意深く洗います。
万が一飲み込んだ場合は、水で口をすすぎ、直ちに医師の診断を受けます。
安全性プロファイル
Moderately toxic by
intraperitoneal route. Mutation data
reported. When heated to decomposition it
emits toxic fumes of Cl-. See also oDICHLOROBENZENE and p
DICHLOROBENZENE.
職業ばく露
The major uses of o-DCB are as
a process solvent in the manufacturing of toluene diisocyanate and as an intermediate in the synthesis of dyestuffs,
herbicides, and degreasers. p-Dichlorbenzene is used
primarily as a moth repellant, a mildew control agent;
space deodorant; and in insecticides, which accounts for
90% of the total production of this isomer. Information is
not available concerning the production and use of m-DCB.
However, it may occur as a contaminant of o-or p-DCB
formulations. Both o-and p-isomers are produced almost
entirely as by-products during the production of
monochlorobenzene
環境運命予測
Biological. When 1,3-dichlorobenzene was statically incubated in the dark at 25 °C with yeast
extract and settled domestic wastewater inoculum, significant biodegradation with gradual
acclimation was followed by a deadaptive process in subsequent subcultures. At a concentration of
5 mg/L, 59, 69, 39, and 35% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively. At a concentration of 10 mg/L, percent losses were virtually unchanged. After 7, 14,
21, and 28-d incubation periods, percent losses were 58, 67, 31, and 33, respectively (Tabak et al.,
1981).
Photolytic. The sunlight irradiation of 1,3-dichlorobenzene (20 g) in a 100-mL borosilicate
glass-stoppered Erlenmeyer flask for 56 d yielded 520 ppm trichlorobiphenyl (Uyeta et al., 1976).
Chemical/Physical. Anticipated products from the reaction of 1,3-dichlorobenzene with
atmospheric ozone or OH radicals are chlorinated phenols, ring cleavage products, and nitro
compounds (Cupitt, 1980). Based on an assumed base-mediated 1% disappearance after 16 d at 85
oC and pH 9.70 (pH 11.26 at 25 oC), the hydrolysis half-life was estimated to be >900 yr
(Ellington et al., 1988). 1,3-Dichlorobenzene (0.17–0.23 mM) reacted with OH radicals in water
(pH 8.7) at a rate of 5.0 x 10
9/M·sec (Haag and Yao, 1992).
輸送方法
m-DCB: UN2810 Toxic liquids, organic, n.o.s.,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
Technical Name Required. United States DOT Regulated
Marine Pollutant. UN3077 Environmentally hazardous
substances, solis, n.o.s., Hazard class: 9; Labels:
9-Miscellaneous hazardous material, Technical NameRequired. UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
純化方法
Wash it with aqueous 10% NaOH, then with water until neutral, dry and distil it. Conductivity material (ca 10-10 mhos) has been prepared by refluxing over P2O5 for 8hours, then fractionally distilling, and storing with activated alumina. m-Dichlorobenzene dissolves rubber stoppers. [Beilstein 5 IV 657.]
不和合性
For o-DCB and m-DCB: acid fumes,
chlorides, strong oxidizers; hot aluminum, or aluminum
alloys. For p-DCB: Strong oxidizers; although, incompatibilities for this chemical may also include other materials
listed for o-DCB.
廃棄物の処理
Incineration, preferably
after mixing with another combustible fuel. Care must be
exercised to assure complete combustion to prevent
the formation of phosgene. An acid scrubber is necessary
to remove the halo acids produced. 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
1,3-ジクロロベンゼン 上流と下流の製品情報
原材料
準備製品
4-(4-chlorophenoxy-2‘-chlorophenyl-α-bromo ethanone)
2',4'-ジクロロバレロフェノン
1-[[2-(2,4-ジクロロフェニル)-4-エチル-1,3-ジオキソラン-2-イル]メチル]-1H-1,2,4-トリアゾール
2,4-ジクロロベンゾトリフルオリド
Tracid Brilliant Red 10b
イソフタロニトリル
エニルコナゾール
2,4-ジクロロフェナシルブロミド
イトラート
2',4'-ジクロロアセトフェノン
2,4-ジフルオロアニリン
2,4-ジクロロベンゼンスルホニルクロリド
2,4-ジクロロニトロベンゼン
1,4-ジクロロベンゼン
1,3-ジフルオロ-2-ニトロベンゼン