1-メチル-2-ピロリドン 化学特性,用途語,生産方法
外観
無色〜ほとんど無色, 澄明の液体
定義
本品は、次の化学式で表される複素環式化合物である。
溶解性
水に可溶 (＞100g/L水)。エタノール, エーテルに易溶。水、エタノール及びアセトンに極めて溶けやすい。
用途
ペプチド合成用溶媒。
用途
有機合成原料。
用途
農薬、医薬品などの製造中間体
用途
樹脂溶剤、アセチレン溶剤、MOS半導体製造用溶剤、化粧品基剤 (化学工業日報社)
用途
樹脂溶剤、アセチレン溶剤
化粧品の成分用途
溶剤
特徴
N-メチル-2-ピロリドン (NMP)は窒素を含む5員環化合物で、次のような優れた特性を持っているので、非常に広い範囲に使用されます。
■ 極性が大きく殆どの有機溶媒（アルコール、エーテル、ケトン、芳香族炭化水素、塩素化炭化水素など）と完全に混合し、また有機物、無機物に対する溶解度が大きい。
■ 水と任意の割合で混合する。
■ 類似の他の溶剤に比して引火点が高い。
■ 沸点が高く凝固点が低く取り扱いが容易である。
■ 化学的及び熱的に安定であり、また腐食性がない。
主な用途
N-メチル-2-ピロリドン（NMP）は優れた特性を持つ極性溶媒です。非常に高い溶解性を持ち、且つ高沸点?低凝固点であるため取扱いが容易で非常に広い範囲で使用されています。
■ NMPはマスケミカルからファインケミカル製造まで幅広く使用されています。
■ 近年NMPの極性の大きさ、溶解力等の特性と弊社製品の高純度、高品位に起因した高性能溶剤としての用途が情報電子分野を中心に拡大しています。
■ 溶剤型接着剤に使用される。
■ フロン溶剤と同等以上の有機物、無機物に対する溶解力を持ち、工業各分野において、洗浄剤や剥離剤として使用されています。
１）情報電子
ワックス、フラックス除去
バリ除去
電子部品洗浄
半導体部品洗浄
リチウム2次電池部材製造用溶剤
半導体用フォトレジストシンナー
カラーフィルター用フォトレジストシンナー
２）自動車
成形金型洗浄
金属（部品）洗浄
３）化学
抽出剤（アセチレン、BTX、ブタジエン）
合成樹脂の表面コーティング溶剤
反応溶媒（PPS、ポリイミド等）
装置洗浄
４）光学
プラスティックレンズ製造用型枠冶具洗浄
５）医薬?農薬
水溶化溶媒
洗浄
抽出
使用上の注意
不活性ガス封入
説明
N-Methyl-2-pyrrolidone is an aprotic solvent with a
wide range of applications: petrochemical processing,
surface coating, dyes and pigments, industrial and
domestic cleaning compounds, and agricultural and
pharmaceutical formulations. It is mainly an irritant,
but has also caused several cases of contact dermatitis
in a small electrotechnical company.
化学的特性
N-Methyl-2-pyrrolidone is a colourless or light yellow liquid with an amine odour. It can undergo a number of chemical reactions even though it is accepted as a stable solvent. It is resistant to hydrolysis under neutral conditions, but strong acid or base treatment results in ring opening to 4-methyl aminobutyric acid. N-Methyl-2-pyrrolidone can be reduced to 1-methyl pyrrolidine with borohydride. Treatment with chlorinating agents results in amide formation,an intermediate which can undergo further substitution, while treatment with amyl nitrate yields the nitrate. Olefins can be added to the 3 position by treatment first with oxalic esters, then with appropriate aldehyes (Hort and Anderson 1982).
使用
N-Methyl-2-pyrrolidone is a polar solvent that is used in organic chemistry and polymer chemistry. Large scale applications include the recovery and purification of acetylenes, olefins, and diolefins, gas purification, and aromatics extraction from feedstocks.N-Methyl-2-pyrrolidone is a versatile industrial solvent. NMP is currently approved for use only in veterinary pharmaceuticals. The determination of the disposition and metabolism of NMP in the rat will contribute toward understanding the toxicology of this exogenous chemical which man may likely be exposed to in increasing amounts.
調製方法
N-Methyl-2-pyrrolidone is manufactured by the reaction of buytrolactone with methylamine (Hawley 1977). Other processes include preparation by hydrogenation of solutions of maleic or succinic acids with methylamine (Hort and Anderson 1982). Manufacturers of this chemical include Lachat Chemical, Inc, Mequon, Wisconsin and GAF Corporation, Covert City, California.
定義
ChEBI: N-methylpyrrolidin-2-one is a member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group. It has a role as a polar aprotic solvent. It is a N-alkylpyrrolidine, a lactam and a member of pyrrolidin-2-ones.
一般的な説明
N-Methyl-2-Pyrrolidone (NMP) is a powerful, aprotic solvent with high solvency, and low volatility. This colorless, high boiling, high flash point and low vapor pressure liquid carries a mild amine-like odor. NMP has high chemical and thermal stability and is completely miscible with water at all temperatures. NMP can serve as a co-solvent with water, alcohols, glycol ethers, ketones, and aromatic/chlorinated hydrocarbons. NMP is both recyclable by distillation and readily biodegradable. NMP is not found on the Hazardous Air Pollutants (HAPs) list of the 1990 Clean Air Act Amendments.
空気と水の反応
Soluble in water.
反応プロフィール
This amine is a very mild chemical base. N-Methyl-2-pyrrolidone does tend to neutralize acids to form salts plus water. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
危険性
Severe skin and eye irritant. Explosive lim-its 2.2–12.2%.
健康ハザード
Inhalation of hot vapors can irritate nose and throat. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Repeated and prolonged skin contact produces a mild, transient irritation.
火災危険
Special Hazards of Combustion Products: Toxic oxides of nitrogen may be formed in fire.
工業用途
1) N-Methyl-2-pyrrolidone is used as a general dipolar aprotic solvent, stable and unreactive;
2) for extraction of aromatic hydrocarbons from lubricating oils;
3) for carbon dioxide removal in ammonia generators;
4) as a solvent for polymerization reactions and polymers;
5) as a paint stripper;
6) for pesticide formulations (USEPA 1985).
Other non-industrial uses of N-Methyl-2-pyrrolidone are based on its properties as a dissociating solvent suitable for electrochemical and physical chemical studies (Langan and Salman 1987). Pharmaceutical applications make use of the properties of N-Methyl-2-pyrrolidone as a penetration enhancer for a more rapid transfer of substances through the skin (Kydoniieus 1987; Barry and Bennett 1987; Akhter and Barry 1987). N-Methyl-2-pyrrolidone has been approved as a solvent for slimicide application to food packaging materials (USDA 1986).
接触アレルゲン
N-Methyl-2-pyrrolidone is an aprotic solvent with a wide range of applications: petrochemical processing, surface coating, dyes and pigments, industrial and domestic cleaning compounds, and agricultural and pharmaceutical formulations. It is mainly an irritant, but it can cause severe contact dermatitis due to prolonged contact.
安全性プロファイル
Poison by intravenous
route. Moderately toxic by ingestion and
intraperitoneal routes. Mildly toxic by skin
contact. An experimental teratogen.
Experimental reproductive effects. Mutation
data reported. Combustible when exposed
to heat, open flame, or powerful oxidizers.
To fight fire, use foam, CO2, dry chemical.
When heated to decomposition it emits
toxic fumes of NOx.
発がん性
Rats were exposed to N-Methyl-2-pyrrolidone vapor at 0, 0.04, or 0.4 mg/L for 6 h/day, 5 days/week for 2 years.Male rats at 0.4 mg/L showed slightly reduced mean body weight. No life-shortening toxic or carcinogenic effects were observed in rats exposed for 2 years to either 0.04 or 0.4mg/L of N-Methyl-2-pyrrolidone. By the dermal route, a group of 32 mice received an initiation dose of 25mg of N-Methyl-2-pyrrolidone followed 2 weeks later by applications of the tumor promoter phorbol myristate acetate, three times a week, for more than 25 weeks. Dimethylcarbamoyl chloride and dimethylbenzanthracene served as positive controls. Although the N-Methyl-2-pyrrolidone group had three skin tumors, this response was not considered significant when compared with that of the positive controls.
代謝経路
Rats are administered radio-labeled N-methyl-2-
pyrrolidinone (NMP), and the major route of excretion
by rats is via the urine. The major metabolite,
representing 70-75% of the administered dose, is
4-(methylamino)butenoic acid. This unsaturated intact
product may be formed from the elimination of water,
and a hydroxyl group may be present on the
metabolite prior to acid hydrolysis.
代謝
Male Sprague-Dawley rats were given a single intraperitoneal injection (45 mg/kg) of radiolabeled 1-methyl-2-pyrrolidone. Plasma levels of radioactivity and compound were monitored for six hours and the results suggested a rapid distribution phase which was followed by a slow elimination phase. The major amount of label was excreted in the urine within 12 hours and accounted for approximately 75% of the labelled dose. Twenty-four hours after dosage, cumulative excretion (urine) was approximately 80% of the dose. Both ring- and methyl-labeled species were used, as well as both [
14C]- and [3H]-labeled l-methyl-2-pyrrolidone. The initial labeled ratios were maintained during the first 6 hours after dosage. After 6 hours, the liver and intestines were found to contain the highest accumulations of radioactivity, approximately 2-4% of the dose. Little radioactivity was noted in the bile or respired air. High performance liquid chromatography of urine showed the presence of one major and two minor metabolites. The major metabolite (70-75% of the administered radioactive dose) was analyzed by liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry and was proposed to be a 3- or 5-hydroxy-l-methyl-2-pyrrolidone (Wells 1987).
純化方法
Dry the pyrrolidone by removing water as the *benzene azeotrope. Fractionally distil at 10 torr through a 100-cm column packed with glass helices. [Adelman J Org Chem 29 1837 1964, McElvain & Vozza J Am Chem Soc 71 896 1949.] The hydrochloride has m 86-88o (from EtOH or Me2CO/EtOH) [Reppe et al. Justus Liebigs Ann Chem 596 1 1955]. [Beilstein 21 II 213, 21 III/IV 3145, 21/6 V 321.]
1-メチル-2-ピロリドン 上流と下流の製品情報
原材料
準備製品