ベンズアルデヒド 化学特性,用途語,生産方法
外観
無色〜わずかにうすい黄褐色, 澄明の液体
定義
本品は、次の化学式で表される芳香族アルデヒドである。
溶解性
水に微溶 (0.33g/100ml水, 20℃), アルコールに可溶。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
ベンズアルデヒド，クヘントウに似た香りをもつ無色または淡黄色の液体．融点－26 ℃，沸点179 ℃．1.049．1.544．エタノール，エーテルなどに易溶，水に難溶．空気中で酸化されて安息香酸になりやすい．
用途
ベンズアルデヒドは、大半がアミノ酸製剤などの医薬品の合成原料として使用されており、 アミノ酸製剤などになる。また、シンナムアルデヒド (石鹸・洗剤用及び食品用の合成香料) な どの合成原料、トリフェニルメタン系染料の合成原料として使用されている。さらに、ベンズ アルデヒド単体でも香料として使用されている (シーエムシー, 1999)。
用途
有機合成原料、染料、溶剤、香料原料。
合成
工業的には，トルエンの塩素化によって得られる塩化ベンザルを，アルカリで加水分解するか，あるいは酸化モリブデンなどを触媒として，トルエンを直接空気酸化してつくられる．
化粧品の成分用途
変性剤、香料、香味剤
効能
香料
製法
ベンズアルデヒド，天然には，クヘントウ，モモ，アンズなどの精油中に存在する．工業的には，トルエンの塩素化によって得られる塩化ベンザルを，アルカリで加水分解するか，あるいは酸化モリブデンなどを触媒として，トルエンを直接空気酸化してつくられる．
急性毒性
経口投与での LD 50 は、マウスで 1,200 mg/kg、ラットで 1,300～2,850 mg/kg、モルモットでは 1,000 mg/kg である。経皮投与での LD 50 は、ウサギで 1,250 mg/kg 超である。
マウスに致死量のベンズアルデヒドを腹腔内投与した試験で、振戦、鎮静、呼吸困難等の症 状が認められている。
ヒト健康への影響
ベンズアルデヒドは実験動物において、主として安息香酸に酸化された後、グリシン抱合や グルクロン酸抱合を受け、最終的には大部分が馬尿酸に代謝され、尿中へ排泄される。
ヒトに対しては、ベンズアルデヒドに暴露した場合、皮膚、眼、呼吸器等に刺激症状が認め られており、またパッチテストで一部のボランティアに陽性を示す報告が得られている。
実験動物に対するベンズアルデヒドの急性毒性については、経口投与での LD 50 はマウスで 1,200 mg/kg、ラットで 1,300～2,850 mg/kg、モルモットでは 1,000 mg/kg である。経皮投与での LD 50 は、ウサギで 1,250 mg/kg 超である。マウスに致死量のベンズアルデヒドを腹腔内投与し た試験で、振戦、鎮静、呼吸困難等の症状が認められている。
ベンズアルデヒド有害性評価書
使用上の注意
空気中で酸化されて安息香酸を生成する。
化学的特性
Benzaldehyde is a colorless to yellow, oily liquid with an odor of bitter almonds. Benzaldehyde is commercially available in two grades: (i) pure benzaldehyde and (ii) and double-distilled benzaldehyde. The latter has applications in the pharmaceutical, perfume, and fl avor industries. Benzaldehyde may contain trace amounts of chlorine, water, benzoic acid, benzyl chloride, benzyl alcohol, and/or nitrobenzene. Benzaldehyde is ignited relatively easily on contact with hot surfaces. This has been attributed to the property of very low auto-ignition temperature. Benzaldehyde also undergoes autoxidation in air and is liable to self-heat. It is used as a food flavoring and in the manufacture of dyes and antibiotics, and can be readily manufactured by the chlorination of methylbenzene and the subsequent hydrolysis of (dichloromethyl) benzene: C6H5CH3 + Cl2 →C6H5CHCl2C6H5CHCl2 + 2H2O →C6H5CH(OH)2+ 2HCl C6H5CH(OH)2 →C6H5CHO + H2O.
天然物の起源
Benzaldehyde exists in nature, occurring in combined and uncombined forms in many plants. It is also the main constituent of the essential oils obtained by pressing the kernels of peaches, cherries, apricots, and other fruits. Benzaldehyde is released into the environment in emissions from combustion processes, such as gasoline and diesel engines, incinerators, and wood burning. It is formed in the atmosphere through photochemical oxidation of toluene and other aromatic hydrocarbons.
使用
Benzaldehyde is a flavoring agent which is liquid and colorless, and
has an almond-like odor. it has a hot (burning) taste. it is oxidized
to benzoic acid when exposed to air and deteriorates under light.
it is miscible in volatile oils, fixed oils, ether, and alcohol; it is spar-
ingly soluble in water. it is obtained by chemical synthesis and by
natural occurrence in oils of bitter almond, peach, and apricot
kernel. it is also termed benzoic aldehyde.
定義
ChEBI: Benzaldehyde is an arenecarbaldehyde that consists of benzene bearing a single formyl substituent; the simplest aromatic aldehyde and parent of the class of benzaldehydes. It has a role as a flavouring agent, a fragrance, an odorant receptor agonist, a plant metabolite, an EC 3.5.5.1 (nitrilase) inhibitor and an EC 3.1.1.3 (triacylglycerol lipase) inhibitor.
製造方法
Benzaldehyde is prepared by hydrolysis of benzal chloride, for example, in acidic media in the presence of a catalyst such as ferric chloride or in alkaline media with aqueous sodium carbonate. Part of the commercially available benzaldehyde originates from a technical process for phenol. In this process, benzaldehyde is a by-product in the oxidation, in air, of toluene to benzoic acid.
一般的な説明
Benzaldehyde appears as a clear colorless to yellow liquid with a bitter almond odor. Flash point near 145 °F. More denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. The primary hazard is to the environment. Immediate steps should be taken to limit spread to the environment. Easily penetrates the soil to contaminate groundwater and nearby waterways. Used in flavoring and perfume making.
空気と水の反応
Oxidizes in air to form benzoic acid, which is moderately toxic by ingestion. Insoluble in water.
反応プロフィール
A nontoxic, combustible liquid, reacts with oxidizing reagents. Benzaldehyde must be blanketed with an inert gas at all times since Benzaldehyde is oxidized readily by air to benzoic acid [Kirk-Othmer, 3rd ed., Vol. 3, 1978, p. 736]. In contact with strong acids or bases Benzaldehyde will undergo an exothermic condensation reaction [Sax, 9th ed., 1996, p. 327]. A violent reaction was observed on contact with peroxyacids (peroxyformic acid) [DiAns, J. et al., Ber., 1915, 48, p. 1136]. An explosion occurred when pyrrolidine, Benzaldehyde, and propionic acid were heated to form porphyrins.
危険性
Highly toxic.
健康ハザード
Benzaldehyde exhibited low to moderate toxicityin test animals, the poisoning effectdepending on dosage. Ingestion of 50–60 mLmay be fatal to humans. Oral intake of a largedose can cause tremor, gastrointestinal pain,and kidney damage. Animal experimentsindicated that ingestion of this compoundby guinea pigs caused tremor, bleeding fromsmall intestine, and an increase in urine volume;in rats, ingestion resulted in somnolenceand coma.
LD50 value, oral (guinea pigs): 1000 mg/kg
LD50 value, oral (rats): 1300 mg/kg
A 500-mg amount for a 24-hour periodresulted in moderate skin irritation in rabbits.Because of its low toxicity, high boilingpoint, and low vapor pressure, the healthhazard to humans from exposure to benzaldehydeis very low.
火災危険
HIGHLY FLAMMABLE: Will be easily 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.
化学反応性
Reactivity with Water: No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
安全性プロファイル
Poison by ingestion
and intraperitoneal routes. Moderately
toxic by subcutaneous route. An allergen.
Acts as a feeble local anesthetic. Local
contact may cause contact dermatitis.
Causes central nervous system depression in
small doses and convulsions in larger doses.
A skin irritant. Questionable carcinogen
with experimental tumorigenic data.
Mutation data reported. Combustible liquid.
To fight fire, use water (may be used as a
blanket), alcohol, foam, dry chemical. A
strong reducing agent. Reacts violently with
peroxyformic acid and other oxidizers. See
also ALDEHYDES.
職業ばく露
In manufacture of perfumes, dyes, and
cinnamic acid; as solvent; in flavors.
代謝
Benzaldehyde was among 300 volatile constituents detected in the urine of ten adults . It is commonly converted to hippuric acid in vivo. In the rabbit and dog, hippuric acid appears to be the only metabolite there being practically no formation of benzoyl glucuronide. The conversion of benzaldehyde to benzoic acid in the rabbit follows first-order reaction kinetics
貯蔵
Benzaldehyde should be kept stored in a tightly closed container and protected against
physical damage. Storage of the chemical substance outside or in a detached area is preferred, whereas inside storage should be in a standard flammable liquids storage room or
cabinet. Benzaldehyde should be kept separated from oxidizing materials. Also, storage
and use areas should be no smoking areas. Containers of this material may be hazardous
when empty since they retain product residues (vapors, liquid); observe all warnings and
precautions listed for the product
輸送方法
UN1990 Benzaldehyde, Hazard class: 9; Labels:
9—Miscellaneous hazardous material.
純化方法
To diminish its rate of oxidation, benzaldehyde usually contains additives such as hydroquinone or catechol. It can be purified via its bisulfite addition compound but usually distillation (under nitrogen at reduced pressure) is sufficient. Prior to distillation it is washed with NaOH or 10% Na2CO3 (until no more CO2 is evolved), then with saturated Na2SO3 and H2O, followed by drying with CaSO4, MgSO4 or CaCl2. [Beilstein 7 IV 505.]
不和合性
The substance reacts with air, forming
explosive peroxides. Reacts violently with performic acid,
oxidants, aluminum, iron, bases, and phenol, causing fire
and explosion hazard. May self-ignite if absorbed in combustible
material with large surface area, or otherwise dispersed
over large areas. Reacts with rust, amines, alkalies, strong
bases, reducing agents such as hydrideds and active metals.
廃棄物の処理
Incineration; add combustible
solvent and spray into incinerator with afterburner.
予防処置
Workers should be careful when using benzaldehyde because there is a risk of spontaneous combustion. It may ignite spontaneously if it is absorbed onto rags, cleaning cloths,
clothing, sawdust, diatomaceous earth (kieselguhr), activated charcoal, or other materials with large surface areas in workplaces. Workers should avoid handling the chemical
substance and should not cut, puncture, or weld on or near the container. Exposure of
benzaldehyde to air, light, heat, hot surfaces such as hot pipes, sparks, open flames, and
other ignition sources should be avoided. Workers should wear proper personal protective
clothing and equipment
ベンズアルデヒド 上流と下流の製品情報
原材料
準備製品
rac-(R*)-α-ヒドロキシベンゼン酢酸
フラバノン
2-アミノ-5-クロロベンズヒドロール
プロパフェノン·塩酸塩
trans-2-フェニル-1-シクロプロパンカルボン酸
whitener WG for wool
Benzenemethanol, ar-methyl-, acetate
ベンジルヒドラジン二塩酸塩
α-ヘキシルシンナムアルデヒド
ジアベリジン
ブリリアントブルーG
2,4,5-トリフェニルイミダゾール
L-2-フェニルグリシン
3,4-ジクロロベンジルアミン
Magentagreencrystals
Reactive Blue BRF
ベンザルアセトン
5,5-ジフェニルヒダントイン
1-アミノ-4-メチルピペラジン二塩酸塩一水和物
α-アセトアミド桂皮酸
インドール-2-カルボン酸メチル
N-エチル-N-[4-[[4-[エチル[[3-スルホフェニル]メチル]アミノ]フェニル](2-スルホナトフェニル)メチレン]-2,5-シクロヘキサジエン-1-イリデン]-3-スルホベンゼンメタンアミニウムジアンモニウム
4-フルオロ-α-(2-メチル-1-オキソ-プロピル)-γ-オキソ-N-β-ジフェニルベンゼン ブタンアミド
N,N'-ジベンジルエチレンジアミンジアセタート
ビス(ジベンジリデンアセトン) パラジウム(0)
アストラゾンブリリアントレッド4G
C.I.リアクティブブルー104
ニフェジピン
エパルレスタット
4-(4-ヒドロキシフェニル)-3-ブテン-2-オン
(2-フェニル-1,3-ジオキソラン-4-イル)メタノール
3,5-ジフェニル-1H-ピラゾール
2-((E)-2-Hydroxy-3-phenylacryloyl)benzoic acid ,97%
(R)-(+)-N-ベンジル-1-フェニルエチルアミン
N,N'-ビスベンジリデンベンジジン
ニトロブルーテトラゾリウム
L-アルギニン/塩酸,(1:x)
(E)-3-Benzylidene-3H-isochromene-1,4-dione ,97%
2,3,5-トリフェニルテトラゾリウムクロリド
トリス(ジベンジリデンアセトン)ジパラジウム(0)