2-ピロリドン 化学特性,用途語,生産方法
外観
白色/無色～ほとんど白色/ほとんど無色粉末～塊～透明液体
溶解性
水, エタノール, アセトン, 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
溶剤、有機合成原料
特徴
2-ピロリドン(２Ｐ)は窒素を含む５員環化合物で次のような特徴があります。
- ほとんどの有機溶媒（アルコール、エーテル、エステル、芳香族炭化水素、塩素化炭化水素、二硫化炭素など）と完全に混合する。
- 水と任意の割合で混合する。
- 沸点が高い。
- 化学的、熱的に安定で腐食性がない。
主な用途
2-ピロリドン（2P）は優れた特性を持つ溶媒で、殆どの有機溶剤と完全に混合し、高沸点であることから、非常に広い範囲で使用されています。
主な用途
■ 医薬、化粧品原料
γ－アミノ酪酸原料
ポリビニルピロリドン原料
■ 抽出剤
芳香族化合物の抽出
■ 高分子ベース床ポリッシャーの可塑剤
アクリル系
アクリル－スチレン系
■ 脱色剤
灯油
ロジン
脂肪酸
■ 溶剤
合成樹脂
農薬（クロルダン他）
多価アルコール（グリセリン、ソルビトール）
その他（印刷インク等）
■ 有機合成の出発原料
N－メチロール化合物
γ－アミノ酸誘導体
■ 高分子原料
化学的特性
2-Pyrrolidinone occurs as a colorless or slightly grayish liquid, as white or almost white crystals, or colorless crystal needles. It has a characteristic odor. miscible with water, alcohol, ether, chloroform, benzene, ethyl acetate and carbon disulfide, insoluble in petroleum ether.
定義
ChEBI: 2-Pyrrolidinone is the simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group. The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamma-aminobutyric acid (GABA). It has a role as a polar solvent and a metabolite.
調製方法
The synthesis of 2-pyrrolidone was first reported in 1889 as the product of
dehydration of 4-aminobutanoic acid. It is produced commercially by condensation
of butyrolactone with ammonia, a method first described in 1936. Other
synthetic routes include carbon monoxide insertion into allylamine, hydrolytic
hydrogenation of succinonitrile, and hydrogenation of ammoniacal solutions of
maleic and succinnic acids (Hort and Anderson 1978).
健康ハザード
Exposure to 2-pyrrolidone produces irritation to the eyes, mucous membranes, and
skin. Although reported to be a skin sensitizer in animal tests, there is no indication
that 2-pyrrolidone is a skin sensitizer in human exposures (Anon 1975). 2-Pyrrolidone
has been reported to enhance the permeability of human skin for methanol,
but reduced the permeability for octanol (Southwell et al 1983).
応用例（製薬）
Pyrrolidone and N-methylpyrrolidone are mainly
used as solvents in veterinary injections. Pyrrolidone has been
shown to be a better solubilizer than glycerin, propylene glycol, or
ethanol. They have also been suggested for use in human
pharmaceutical formulations as solvents in parenteral, oral, and
topical applications. In topical applications, pyrrolidones appear to
be effective penetration enhancers. Pyrrolidones have also been
investigated for their application in controlled-release depot
formulations.
工業用途
2-Pyrrolidone is used as an intermediate for synthesis of l-vinyl-2-pyrrolidone and
various TV-methylol derivatives used as textile-finishing agents; as a solvent for
various polymers, chlordane and DDT, d-sorbitol, glycerin, and sugars; and as a
decolorizing agent for kerosene, fatty oils, and rosins. N-methyl-2-pyrrolidone and
2-pyrrolidone are utilized in petroleum refining to selectively extract aromatics
from paraffinic hydrocarbons. 2-Pyrrolidone is used as a plasticizer and coalescing
agent for acrylic latices and acrylic/styrene copolymers in emulsion coatings, i.e.
floor waxes. A linear high molecular weight polyamide polymer of 2-pyrrolidone,
nylon-4, is used as a textile fiber, injection molding compound, and film-forming
polymer (Anon. 1975; Hort and Anderson 1978).
安全性
Pyrrolidones are mainly used in veterinary injections and have also
been suggested for use in human oral, topical, and parenteral
pharmaceutical formulations. In mammalian species, pyrrolidones
are biotransformed to polar metabolites that are excreted via the
urine. Pyrrolidone is mildly toxic by ingestion and subcutaneous
routes; mutagenicity data have been reported.
LD50 (guinea pig, oral): 6.5 g/kg
LD50 (rat, oral): 6.5 g/kg
代謝
A metabolite of 2-pyrrolidone, 4-aminobutanoic acid has been identified in
animals (Lundgren et al 1980). 2-Pyrrolidone has been reported to be an endogenous
constituent in the brains of mice (Callery et al 1978) and bovine (Mori et al
1975). The aliphatic polyamine putrescine has been demonstrated to be metabolized
to 2-pyrrolidone in rat liver slices (Lundgren and Hankins 1978; Lundgren et
al 1985) and to lesser extent by slices of spleen and lung, but not in tissue slices
from kidney, brain, heart, or rear leg muscle (Lundgren and Hankins 1978). The
metabolism of putrescine is catalyzed by the microsomal enzyme diamine oxidase
(EC 1.4.3.6) to 4-aminobutyraldehyde, which is subsequently oxidized to the
neurotransmitter 4-aminobutanoic acid (4-aminobutyric acid, GAB A) or is cyclized
to delta1-pyrroline (Seiler 1980; Lundgren et al 1980; Callery et al 1980),
which is in turn oxidized to 5-hydroxy-2-pyrrolidone (Lundgren and Fales 1980).
There is evidence that 5-hydroxy-2-pyrrolidone is further metabolized to succinimide,
malimide, 2- and 3-hydroxysuccinamic acids, maleamic acid, and carbon
dioxide (Bandle et al 1984). An enzyme system residing in the soluble fraction of
rabbit liver catalyzes the conversion of delta'-pyrroline to ?-aminobutyric acid and
its lactam, 2-pyrrolidone (Callery et al 1982). 2-Pyrrolidone has been identified as a urinary metabolite of N-nitrosopyrrolidine (Cottrell et al 1980) and the drug
methadone (Kreek 1980).
貯蔵
Pyrrolidone is chemically stable and, if it is kept in unopened
original containers, the shelf-life is approximately one year.
Pyrrolidone should be stored in a well-closed container protected
from light and oxidation, at temperatures below 20°C.
不和合性
Pyrrolidone is incompatible with oxidizing agents and strong acids.
2-ピロリドン 上流と下流の製品情報
原材料
準備製品