ベンゾイルクロリド 化学特性,用途語,生産方法
外観
無色澄明の液体
性質
もっとも簡単な芳香族酸ハロゲン化物の一つ。刺激性のある無色の液体で,湿気の多い空気中で白煙を生じる。沸点197.2℃,融点-0.5℃。水と反応し,安息香酸C6H5COOHと塩化水素を生じる。クロロホルムやベンゼンには反応せず溶けるが,メチルアルコールやエチルアルコールとは反応し,安息香酸メチルエステルや安息香酸エチルエステルと塩化水素を生じる。製法は,安息香酸と五塩化リンまたは塩化チオニルSOCl2との反応による。
溶解性
水又はエタノールによって分解する。
解説
C7H5ClO(140.57).C6H5COCl.安息香酸に五塩化リンまたは塩化チオニルを反応させると得られる酸塩化物.刺激臭の強い無色の液体.融点-1 ℃,沸点198 ℃.d15151.219.n20D1.5537.容易に加水分解して安息香酸に戻る.アルコール,フェノール,アミンなどと反応してベンゾイル誘導体をつくるので,ベンゾイル化剤として用いられる.[CAS 98-88-4]
森北出版「化学辞典(第2版)
解説
ベンゾイルクロリドは,カルボン酸塩化物の一つ。刺激臭のある無色液体。安息香酸と塩化チオニルとの反応、または(トリクロロメチル)ベンゼン(α,α,α-トリクロロトルエン)の部分加水分解反応により合成する。水と徐々に反応して安息香酸と塩化水素になる。種々の有機化合物にベンゾイル基C6H5CO-を導入するベンゾイル化剤として、またアントラキノン系染料中間体原料として用いられる。ベンゾイル化試薬,過酸化ベンゾイルの原料として用いられるほか,いろいろな染料,薬品の合成原料,特にアントラキノン系建染め染料の合成中間体として重要である。催涙性があり、皮膚、目、粘膜を刺激する。[谷利陸平]
用途
有機過酸化物原料、染料、その他有機合成用、香料、ベンゾイル基導入剤
用途
医薬品原料、有機合成原料
化学的特性
Benzoyl chloride is a colorless to slight brown liquid with a strong, penetrating odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible. It is a liquid acyl chloride used as a benzoylating agent.
調製方法
Benzoyl chloride can be prepared from benzoic acid by reaction with PCl5 or SOCl2, from benzaldehyde by treatment with POCl3 or SO2 Cl2, from benzotrichloride by partial hydrolysis in the presence of H2SO4 or FeCl3, from benzal chloride by treatment with oxygen in a radical source, and from several other miscellaneous reactions. Benzoyl chloride can be reduced to benzaldehyde, oxidized to benzoyl peroxide, chlorinated to chlorobenzoyl chloride and sulfonated to m-sulfobenzoic acid. It will undergo various reactions with organic reagents. For example, it will add across an unsaturated (alkene or alkyne) bond in the presence of a catalyst to give the phenylchloroketone:
定義
ChEBI: Benzoyl chloride is an acyl chloride consisting of benzene in which a hydrogen is replaced by an acyl chloride group. It is an important chemical intermediate for the manufacture of other chemicals, dyes, perfumes, herbicides and pharmaceuticals. It has a role as a carcinogenic agent. It is an acyl chloride and a member of benzenes. It is functionally related to a benzoic acid.?
一般的な説明
Benzoyl chloride appears as a colorless fuming liquid with a pungent odor. Flash point 162 °F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals.
反応プロフィール
Benzoyl chloride reacts violently with protic solvents such as alcohols, with amines and amides (for example dimethylformamide [Bretherick 1979 p. 6] ) and with inorganic bases. Causes the violent decomposition of dimethyl sulfoxide [Chem. Eng. News 35(9): 87 1957]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Friedel-Crafts acylation of naphthalene using Benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].
危険性
Highly toxic. Strong irritant to skin, eyes,
and mucous membranes, and via ingestion, inhala-
tion. Upper respiratory tract irritant. Probable car-
cinogen.
健康ハザード
INHALATION: may irritate eyes, nose and throat. INGESTION: causes acute discomfort. SKIN: causes irritation and burning.
使用用途
塩化ベンゾイルの使用用途は下記の通りです。
1. 有機化学
塩化ベンゾイルの持つ酸化チオニル部分 (-COCl) は非常に反応性が高いため、さまざまな求核剤と反応を起こします。例えば、やなどのアルコールと反応し、安息香酸メチルエステルや安息香酸エチルエステルと塩化水素を生じるといったエステル化の反応を起こします。やアミン等とも反応し、ベンゾイル誘導体を作ります。
2. 物質の合成
塩化ベンゾイルとを反応させることで、過酸化ベンゾイルに変換することができます。過酸化ベンゾイルは非常に反応性に富むペルオキシドと呼ばれる化合物の一種で、ラジカルを利用した重合反応の開始剤としても用いられます。
不飽和ポリエステル等の橋かけ硬化剤、酸化漂白剤にも使われているほか、様々な染料・薬品・香料等の合成原料、特に、アントラキノン系建染め染料の合成中間体として、重要な物質とされています。
法規情報
塩化ベンゾイルは消防法にて「第4類引火性液体、第三石油類非水溶性液体」に、毒物及び劇物取締法にて「劇物」に指定されています。労働安全衛生法では「名称等を表示すべき危険有害物」「名称等を通知すべき危険有害物」にそれぞれ指定されており、取り扱いには注意が必要です。
参考文献
化学反応性
Reactivity with Water Slow reaction with water to produce hydrochloric acid fumes. The reaction is more rapid with steam; Reactivity with Common Materials: Slow corrosion of metals but no immediate danger; Stability During Transport: Not pertinent; Neutralizing Agents for Acids and Caustics: Soda ash and water, lime; Polymerization: Does not occur; Inhibitor of Polymerization: Not pertinent.
作用機序
Indicative of its high reactivity (relative to alkyl chlorides), benzyl chloride reacts with water in a hydrolysis reaction to form benzyl alcohol and hydrochloric acid. In contact with mucous membranes, hydrolysis produces hydrochloric acid. Thus, benzyl chloride is a lachrymator and has been used in chemical warfare. Theoretically, for every mole of benzyl chloride reacted, one mole of hydrochloric acid is released[1].
毒性学
Benzoyl chloride is of low acute oral toxicity in
rats (LD
50 2529 mg/kg). It is more toxic by
inhalation (LC
50 230 ppm, 4 h in male rats and
314 ppm, 4 h in female rats). The compound is
irritating to skin, mucous membranes, eyes, and
the respiratory tract.
When benzoyl chloride or solutions of benzoyl chloride in benzene were applied to the skin of
mice for up to 10 months irritation and keratinization resulted, and to some extent, ulceration
and necrosis of the skin occurred. A few tumors
(skin, lung) were observed in those mice.
There is no clear evidence that benzoyl chloride
is mutagenic.
For humans, benzoyl chloride is classified as a
lachrymator. It is irritating to the skin, eyes, and
mucous membranes. The available data are
inadequate to evaluate the carcinogenic potential
of benzoyl chloride to humans.
職業ばく露
Benzoyl chloride is used as a chemical
intermediate; in organic synthesis; to produce other chemicals,
dyes, perfumes, herbicides, and medicines.
輸送方法
UN 1736 Benzoylchloride, Hazard class: 8;
Labels: 8—Corrosive material.
純化方法
A solution of benzoyl chloride (300mL) in *C6H6 (200mL) is washed with two 100mL portions of cold 5% NaHCO3 solution, separated, dried with CaCl2 and distilled [Oakwood & Weisgerber Org Synth III 113 1955]. Repeated fractional distillation at 4mm Hg through a glass helices-packed column (avoiding porous porcelain or silicon-carbide boiling chips, and hydrocarbon or silicon greases on the ground joints) gave benzoyl chloride that did not darken on addition of AlCl3. Further purification is achieved by adding 3 mole% each of AlCl3 and toluene, standing overnight, and distilling off the benzoyl chloride at 1-2mm [Brown & Jenzen J Am Chem Soc 80 2291 1958]. Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used. [Beilstein 9 IV 721.] Strong IRRITANT. Use in a fume cupboard.
不和合性
May form explosive mixture with air.
Contact with heat, hot surfaces, and flames causes decomposition,
forming phosgene and hydrogen chloride. Water
contact may be violent; forms hydrochloric acid. Reactions
with amines, alcohols, alkali metals, dimethyl sulfoxide,
strong oxidizers, and metal salts may be violent, causing
fire and explosions. Attacks metals in the presence of
moisture, forming explosive hydrogen gas. Attacks some
plastics, rubber or coatings.
廃棄物の処理
Pour into sodium bicarbonate
solution and flush to sewer.
ベンゾイルクロリド 上流と下流の製品情報
原材料
準備製品