4-メチル-3-ペンテン-2-オン 化学特性,用途語,生産方法
外観
無色～黄色、液体
解説
メシチルオキシド，4-methyl-3-penten-2-one．C6H10O(98.15)．(CH3)2CCHCOCH3．イソプロピリデンアセトンともいう．アセトンに硫酸を作用させるか，イソブチレンに臭化アルミニウムを触媒にして塩化アセチルを作用させると得られる．ハッカに似た香りをもつ液体．融点－52.8 ℃，沸点130 ℃．0.8510．1.4484．水に微溶，有機溶媒に易溶．溶解力が強く，ニトロセルロース，ビニル樹脂，ポリスチレン，ネオプレンゴムなどの溶剤に用いられる．
用途
セルロースや樹脂の溶媒、4-メチル-2-ペンタノンの原料 ラッカー、インキ、標本用染料、浮遊選鉱、ペンキ、ワニスの除去剤、昆虫の忌避剤、溶剤
説明
The commercial grade of 4-methyl-3-penten-2-one exhibits an unpleasant grassy-green or pungent, acrylic odor. The pure material has a pleasant, honey-like odor. This substance may be prepared by reacting acetone or diacetone alcohol with iodine or other dehydrating agent; by condensation of acetone over sulfonated polystyrene-divinylbenzene resin used as an ion exchange catalyst.
化学的特性
Mesityl oxide is a clear, pale yellow, or colorless liquid with a strong peppermint odor. The odor threshold is 0.05 ppm.
物理的性質
Clear, pale yellow liquid with a strong, peppermint, or honey-like odor. Experimentally
determined detection and recognition odor threshold concentrations were 70 μg/m
3 (17 ppb
v) and
200 μg/m
3 (50 ppb
v), respectively (Hellman and Small, 1974).
天然物の起源
Reported found in orange juice, baked potato, bell pepper, sauerkraut, tomato, crisp bread, parmesan cheese,
milk, chicken fat, hop oil, rum, coffee, tea, peanut, passion fruit, mushroom, tamarind, prickly pear, buckwheat, basil, elder flower,
rosemary, shrimp, nectarine, clam and maté
使用
4-Methyl-4-penten-2-one is used to a
small extent as an intermediate in synthesis. Most
of it is converted to 4-methyl-2-pentanone by
selective hydrogenation. Although 4-methyl-2-
pentanone has excellent solvent properties for
nitrocellulose, cellulose esters and ethers, copolymers of vinyl chloride – vinyl acetate and
other synthetic resins, as well as natural and
synthetic rubber, its use as a solvent is limited
as a result of its toxicity and chemical instability.
The fraction of 4-methyl-4-penten-2-one permitted in solvent systems has been set at 5 vol%
(Rule 66 of the Los Angeles, California, Air
Pollution Control District).
Some of the numerous possible reactions that
mesityl oxide may undergo have been used for
the synthesis of products such as Budralazine, an
antihypertensive agent.
製造方法
4-Methyl-4-penten-2-one is the precursor of methyl isobutyl ketone (see Section 2.2) and can be produced from acetone in a single- or a two-step process . Pure mesityl oxide is obtained by azeotropic distillation of the crude watercontaining product. Subsequent purification by removal of the accompanying impurities, such as mesitylene and phorone [504-20-1], is effected by distillation.
一般的な説明
Mesityl oxide appears as a colorless, oily liquid with a pungent honey-like odor. Flash point 87 °F. Less dense than water and slightly soluble in water. Vapors heavier than air. Used in paint removers, as a solvent for plastics, and as an insect repellent.
空気と水の反応
Highly flammable. Slightly soluble in water
反応プロフィール
Mixing MESITYL OXIDE in equal molar proportions with any of the following substances in a closed container caused the temperature and pressure to increase: 2-aminoethanol, chlorosulfonic acid, ethylene diamine, nitric acid, oleum, or sulfuric acid [NFPA 1991].
危険性
Flammable, moderate fire risk. Toxic by
ingestion, inhalation, and skin absorption. Eye and
upper respiratory tract irritant, central nervous system impairment.
健康ハザード
Mesityl oxide is a moderately toxic substance, more toxic than the saturated ketones.Inhalation of its vapors can cause irritationto the eyes, skin, and mucous membranes. Inhumans, the irritation effect on the eyes andnose are reported to be 25 and 50 ppm. Athigh concentrations narcosis can result. Otherthan narcosis, prolonged exposure to highconcentrations can injure the lungs, liver, and kidney. A concentration of 2500 ppm waslethal to rats.
LD50 value, oral (rats): 1120 mg/kg.
火災危険
Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back.
安全性プロファイル
Poison by
intraperitoneal route. Moderately toxic by
ingestion. Mildly toxic by inhalation and skin
contact. Human systemic effects by
inhalation: conjunctiva irritation. This
compound is highly irritating to all tissues
on contact; its vapors also are irritating.
High concentrations are narcotic. It is
readdy absorbed through intact skin. Single
exposures tend to indicate that ths ketone
has greater acute and narcotic action than
isophorone. It can have harmful effects
upon the hdneys and liver, and may damage
the eyes and lungs to a serious degree.
Prolonged exposure can injure liver, kidneys,
and lungs. It can cause opaque cornea,
keratoconus, and extensive necrosis of
cornea. Dangerous fire hazard when
exposed to heat, sparks, or flame; can react
with oxidzing materials. Reacts violently
with 2-amino ethanol, chlorosulfonic acid,
ethylene diamine, HNO3, oleum, H2SO4. An
insect repellent. To fight fire, use alcohol
foam, CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also KETONES.
職業ばく露
Mesityl oxide is used as a solvent for
cellulose esters and ethers and other resins in lacquers and
inks. It is used in paint and varnish removers and as an
insect repellent
輸送方法
UN1229 Mesitly oxide, Hazard Class: 3; Labels:
3-Flammable liquid.
純化方法
Purify it by distillation, preferably in a vacuum or via the semicarbazone (m 165o) which is decomposed to pure ketone. The 2,4-dinitrophenylhydrazone (m 205-206o) crystallises from EtOH. [Johnson J Am Chem Soc 73 5888 1951, Johnson J Am Chem Soc 75 2720 1953, Erskine & Waight J Chem Soc 3425 1960, Beilstein 1 H 736, 1 I 382, 1 II 793, 1 III 2995, 1 IV 3471.]
不和合性
May form explosive mixture with air.
May be able to form explosive peroxides. May react
violently with nitric acid; aliphatic amines; alkanolamines, 2-
aminoethanol, ethylene diamine; chlorosulfonic acid; oleum
(fuming sulfuric acid). Not compatible with oxidizers, strong
acids; strong bases; reducing agents; halogens. Dissolves
some forms of plastics, resins and rubber. Attacks copper.
廃棄物の処理
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be observed.
4-メチル-3-ペンテン-2-オン 上流と下流の製品情報
原材料
準備製品
1-(2-ブテノイル)-2,6,6-トリメチル-1,3-シクロヘキサジエン
メチルネオペンチルケトン
4-メチル-4-アミノペンタン-2-オン
1-（2，6，6-トリメチル-3-シクロヘキセン-1-イル）ブタ-2-エン-1-オン
ADS
2,2,3,3-テトラメチルヘキサン
2,2,4,4,6-pentamethyl-hexahydropyrimidine
7-Quinolinol, 1-ethyl-1,2-dihydro-2,2,4-trimethyl-