アクリル酸エチル

外観

無色澄明の液体

種類

アクリル酸エチルには、産業用の大型容量製品や、試薬用途の小型製品があります。化学分野における試薬用の小型製品の主な容量規格は、1g, 5g, 25g, 50g, 100g, 100mL, 500mL, 1L等です。産業用製品では、15kg缶、180kgドラム缶、ローリーなどの荷姿で流通しています。

定義

本品は、次の化学式で表される有機化合物である。

溶解性

エタノール及びアセトンに溶け、水に溶ける。

用途

アクリル酸エチル（EA）はアクリル酸とエタノールをエステル化した製品で、繊維処理剤、粘接着剤、塗料、合成樹脂、アクリルゴム、エマルション(エマルジョン)等の原料として使用されます。

用途

アクリル繊維、塗料

用途

塗料?粘着剤?接着剤?成型用共重合樹脂 (MMA:メチルメタクリレート、MBS: MMA/ブタジエン/スチレン)?アクリルゴム等の重合原料、凝集剤?加工剤(皮革加工?紙加工?繊維加工)?化粧品原料,NITE初期リスク評価書;アクリル繊維原料、塗料?接着剤原料 (化学工業日報社)

用途

有機合成原料。

化粧品の成分用途

可塑剤

合成

実験室などにおけるアクリル酸エチルの一般的な合成方法は、酸触媒存在下におけるとのエステル化反応です。アクリル酸はもっとも簡単な不飽和カルボン酸であり、化学式はCH2=CHCOOHです (IUPAC命名法では2-プロペン酸 (2-propenoic acid)) 。アクリル酸の工業的合成法は、の酸化が挙げられます。

工業的には、レッペ反応及びその改良反応を用いて合成されることもあります。、、エタノールを原料とし、臭化ニッケル (II) 触媒によって合成を行う方法です。

そのままでは保管中に発生したラジカルによってポリマー化してしまうため、市販品には、通常ヒドロキノンやヒドロキノンモノメチルエーテルなどの重合禁止剤などが添加されています。

使用上の注意

重合禁止剤:Hydroquinone monomethyl ether 約 0.01%添加。

説明

Ethyl acrylate is an organic compound with the formula CH₂CHCO₂CH₂CH₃. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers . It is also a reagent in the synthesis of various pharmaceutical intermediates.

化学的特性

Ethyl acrylate is a colorless liquid. Sharp, acrid odor. The Odor Threshold is 0.00024
0.0009 ppm

物理的性質

Clear, colorless liquid with a penetrating and pungent odor. Leonardos et al. (1969) and Nagata and Takeuchi (1990) reported odor threshold concentrations of 0.47 and 0.26 ppb_v, respectively. Experimentally determined detection and recognition odor threshold concentrations were 1.0 μg/m³ (0.24 ppb_v) and 1.5 μg/m³ (0.37 ppb_v), respectively (Hellman and Small, 1974).

天然物の起源

Reported found in pineapple, yellow passion fruit and durian (Durio zibethinus).

使用

Ethyl Acrylate is a flavoring agent that is a clear, colorless liquid. its odor is fruity, harsh, penetrating, and lachrymatous (causes tears). it is sparingly soluble in water and miscible in alcohol and ether, and is obtained by chemical synthesis.

製造方法

By esterification of acrylic acid; by heating acetylene with HCl in alcoholic solution in the presence of Ni(CO)4; also from ethyl-3-chloropropionate passed over activated carbon at high temperature.

調製方法

Ethyl acrylate is manufactured via oxidation of propylene to acrolein and then to acrylic acid. The acid is treated with ethanol to yield the ethyl ester .
Vinyl chloride reacts at 270 °C at >6895 kPa (68 atm) with ethanol in the presence of a cobalt and palladium catalyst to give ethyl acrylate in a yield of 17% .

安全性

アクリル酸エチルは、下記の危険性が指摘されているため、正しく取り扱うことが重要です。

• 眠気又はめまいのおそれ
• 長期又は反復ばく露による神経系、呼吸器の障害
• 水生生物に毒性
• 長期的影響により水生生物に毒性

ラットとマウスでの実験により発がん性も示唆されていますが、ヒトで発がん性があるかどうかはまだ結論が出ていません。

一般的な説明

A clear colorless liquid with an acrid odor. Flash point 60°F. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. Auto ignition temperature 721°F (383°C) (NTP). Less dense than water. Vapors heavier than air. Used to make paints and plastics.

空気と水の反応

Highly flammable. Insoluble in water.

反応プロフィール

A flammable liquid, confirmed carcinogen. Ethyl acrylate can react vigorously with oxidizing reagents, peroxides,strong alkalis and polymerization initiators. [NTP] Ethyl acrylate reacts violently with chlorosulfonic acid [Sax, 9th ed., 1996, p. 1515]. When an inhibited monomer was placed in a clear glass bottle exposed to sunlight, exothermic polymerization set in and caused the bottle to burst. The use of brown glass or metal containers and increase in inhibitor concentration (to 200 ppm; tenfold) was recommended [MCA Case History No. 1759]. Ethyl acrylate may polymerize when exposed to light and Ethyl acrylate is subject to slow hydrolysis. Inhibitors do not function in the absence of air. Solutions in DMSO are stable for 24 hours under normal lab conditions. [NTP].

危険性

Toxic by ingestion, inhalation, skin absorption; irritant to skin and eyes. Flammable, dangerous fire and explosion hazard. Possible carcinogen.

健康ハザード

Ethyl acrylate is a strong irritant to the eyes,skin, and mucous membranes. The liquid orits concentrated solutions can produce skinsensitization upon contact. It is toxic by allroutes of exposure. The toxicity is low inrats and mice and moderate in rabbits. Thetoxic effects from inhalation noted in animalswere congestion of lungs and degenerativechanges in the heart, liver, and kidney. Mon key exposed to 272 ppm for 28 days showedlethargy and weight loss; while exposure to1024 ppm caused death to the animals after2.2 days (Treon et al. 1949). By compari son, guinea pigs died of exposure to about1200 ppm for 7 hours. Ingestion of the liq uid may result in irritation of gastrointestinaltracts, nausea, lethargy, and convulsions
The LD50 values varied significantly indifferent species of animals. The oral LD50values in rabbits, rats, and mice are in therange 400, 800, and 1800 mg/kg, respectively. Animals administered ethyl acrylateshowed increased incidence of tumors inforestomach. However, there is no evidenceof carcinogenicity caused by this compoundin humans.

使用用途

アクリル酸エチルは、反応性が高いことから、各種化学反応の反応剤として汎用性の高い化合物です。そのため、他のアクリル酸エステル一般と同様に、広範な産業分野において製品原料として活用されています。

具体的には、繊維処理剤、粘接着剤、塗料、合成樹脂、アクリルゴム、エマルジョン等の原料です。更に、皮革や紙などの加工剤や自動車部品、衣料、マスカラなどへも応用されています。また、種々の医薬品中間体の合成試薬として広く活用されています。

その他、香料としても使用が可能です。自然界では、パイナップルおよびボーフォールチーズの揮発性成分として検出されています。

化学反応性

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: May occur; exclude moisture, light; avoid exposure to high temperatures; store in presence of air; Inhibitor of Polymerization: 13-17 ppm monomethyl ether of hydroquinone.

安全性プロファイル

Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion and inhalation. Moderately toxic by skin contact and intraperitoneal routes. Human systemic effects by inhalation: eye, olfactory, and pulmonary changes. A skin and eye irritant. Characterized in its terminal stages by dyspnea, cyanosis, and convulsive movements. It caused severe local irritation of the gastroenteric tract; and toxic degenerative changes of cardiac, hepatic, renal, and splenic tissues were observed. It gave no evidence of cumulative effects. When applied to the intact skin of rabbits, the ethyl ester caused marked local irritation, erythema, edema, thickening, and vascular damage. Animals subjected to a fairly high concentration of these esters suffered irritation of the mucous membranes of the eyes, nose, and mouth as well as lethargy, dpspnea, and convulsive movements. A substance that migrates to food from packagmg materials. Flammable liquid. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with chlorosulfonic acid. To fight fire, use CO2, dry chemical, or alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

安全性

It is an acute toxin with an LD50 (rats, oral) of 1020 mg / kg and a TLV of 5 ppm. The International Agency for Research on Cancer stated, "Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B)." The United States Environmental Protection Agency (EPA) states, "Human studies on occupational exposure to ethyl acrylate... have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papillomas and carcinomas of the fore stomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity since humans do not have a fore stomach, and removed ethyl acrylate from its list of carcinogens." (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time.)
One favorable safety aspect is that ethyl acrylate has good warning properties; the odor threshold is much lower than any level of health concern. In other words, the bad odor warns people of ethyl acrylate's presence long before the concentration reaches a level capable of creating a serious health risk.

職業ばく露

This material is used in emulsion polymers for paints, textiles, adhesives, coatings and binders; as a monomer in the manufacture of homopolymer and copolymer resins for the production of paints and plastic films

概要

アクリル酸エチル (Ethyl Acrylate) とは、アクリル酸エステルの一種である有機化合物です。

EAと省略形で表記されることもあります。常温において、無色透明の液体であり、水への溶解度は1.5g/100mLです。揮発性を呈し、エステル臭と言われる果実などの香りに似た強い匂いを有します。

化学式はCH2＝CHCOOC2H5であり、分子量は100.1、CAS No.は140-88-5です。引火性があるため、消防法では危険物第4類 第1石油類 非水溶性液体として指定されています。

発がん性

A retrospective study found an excess of colorectal cancers in one exposed population of workers; however, the data were confounded by other exposures and lack of association of causality and risk in similarly exposed populations from other locations. Therefore, there was inadequate evidence based on the study that ethyl acrylate is a human carcinogen . Ethyl acrylate is listed as USEPA group B2, “Probable human carcinogen”; IARC group B2, “Possibly carcinogenic in humans”; NIOSH, “Carcinogen with no further categorization”; NTP group 2, “Reasonably anticipated to be a carcinogen” and listed as a carcinogen by California Proposition 65 .
Dermal studies of acrylic acid, ethyl acrylate, and n-butyl acrylate using mice did not result in local carcinogenesis, but several mice in the ethyl acrylate-treated group did exhibit dermatitis, dermal fibrosis, epidermal necrosis, and hyperkeratosis .

環境運命予測

Chemical/Physical. Polymerizes on standing and is catalyzed by heat, light, and peroxides (Windholz et al., 1983). Slowly hydrolyzes in water forming ethanol and acrylic acid. The reported rate constant for the reaction of ethyl acrylate with ozone in the gas phase was determined to be 5.70 x 10^-18 cm³ mol/sec (Munshi et al., 1989).
At an influent concentration of 1,015 mg/L, treatment with GAC resulted in an effluent concentration of 226 mg/L. The adsorbability of the carbon used was 157 mg/g carbon (Guisti et al., 1974).

輸送方法

UN1917 Ethyl acrylate, Hazard Class: 3; Labels: 3-Flammable liquid

純化方法

Wash the ester repeatedly with aqueous NaOH until free from inhibitors such as hydroquinone, then wash it with saturated aqueous CaCl2 and distil it under reduced pressure. Hydroquinone should be added if the ethyl acrylate is to be stored for extended periods. [Beilstein 2 IV 1460.] LACHRYMATORY.

不和合性

May form explosive mixture with air. Atmospheric moisture and strong alkalies may cause fire and explosions unless properly inhibited (Note: Inert gas blanket not recommended). Heat, light or peroxides can cause polymerization. Incompatible with oxidizers (may be violent), peroxides, polymerizers, strong alkalis; moisture, chlorosulfonic acid, strong acids; amines. May accumulate static electrical charges, and may cause ignition of its vapors. Polymerizes readily unless an inhibitor, such as hydroquinone is added. Uninhibited vapors may plug vents by the formation of polymers.

廃棄物の処理

Incineration or by absorption and landfill disposal