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2-피롤리디논

2-피롤리디논
2-피롤리디논 구조식 이미지
카스 번호:
616-45-5
한글명:
2-피롤리디논
동의어(한글):
2-피로리돈;2-피롤리디논;피롤리돈;2-피롤리디논(2-PYRROLIDINONE)
상품명:
2-Pyrrolidinone
동의어(영문):
2-P;α-PVR;2-Pyrol;Pyrrolidon;Soluphor P;Pyrrolidone;-Pyrrolidone;2-pyrolidone;BUTYROLACTAM;2-PYRROLIDON
CBNumber:
CB4453929
분자식:
C4H7NO
포뮬러 무게:
85.1
MOL 파일:
616-45-5.mol

2-피롤리디논 속성

녹는점
23-25 °C(lit.)
끓는 점
245 °C(lit.)
밀도
1.12 g/mL at 25 °C(lit.)
증기 밀도
2.9 (vs air)
증기압
0.04 hPa (20 °C)
FEMA
4829 | 2-PYRROLIDONE
굴절률
n20/D 1.487(lit.)
인화점
>230 °F
저장 조건
2-8°C
용해도
H2O: miscible (completely)
물리적 상태
Liquid or Low Melting Mass
색상
Clear colorless to pale yellow
수소이온지수(pH)
9-11 (100g/l, H2O, 20℃)
폭발한계
1.8-16.6%(V)
수용성
miscible
감도
Hygroscopic
Merck
14,8016
BRN
105241
InChIKey
HNJBEVLQSNELDL-UHFFFAOYSA-N
CAS 데이터베이스
616-45-5(CAS DataBase Reference)
NIST
2-Pyrrolidinone(616-45-5)
EPA
2-Pyrrolidinone(616-45-5)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험 카페고리 넘버 22
안전지침서 24/25
유엔번호(UN No.) 2810
WGK 독일 1
RTECS 번호 UY5715000
자연 발화 온도 395 °C
TSCA Yes
위험 등급 6.1(b)
포장분류 III
HS 번호 29339980
유해 물질 데이터 616-45-5(Hazardous Substances Data)
독성 LD50 orally in Rabbit: > 3200 mg/kg
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
예방조치문구:
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P337+P313 눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.

2-피롤리디논 C화학적 특성, 용도, 생산

용도

2- 피 롤리 돈은 중요한 화학 원료 및 고 극성 유기 용매입니다. 그것은 널리 제약, 섬유, 화장품, 용제, 전자 청소 및 기타 산업에 사용됩니다.

포장, 보관 및 운송

시원하고 바람이 잘 통하는 곳에 보관; 멀리 불 및 열에서; 조심히 다루세요; 파손이없고 누출을 피하십시오. 적절한 조건에서 3 년 동안 유효합니다.

화학적 성질

Clear colorless liquid or low melting solid

화학적 성질

2-Pyrrolidone undergoes the reactions of a typical lactam, e.g. ring opening, attack on the carbonyl group, and replacement of hydrogens alpha to the carbonyl group. Strong acids and bases catalyze the hydrolysis of 2-pyrrolidone to 4-aminobutanoic acid (GABA). The hydrogen atom on the nitrogen atom is easily replaced by alkylation reactions with alkyl halide or sulfates, or reaction with acid anhydrides, acyl halides, ethylene oxide, and styrene. Condensation reactions with secondary amines and alcohols, and O-alkylation reactions occur at the carbonyl group. In the presence of anionic catalyst systems, 2-pyrrolidone is polymerized to polypyrrolidone, nylon-4 (Hort and Anderson 1978).

화학적 성질

Pyrrolidone occurs as a colorless or slightly grayish liquid, as white or almost white crystals, or colorless crystal needles. It has a characteristic odor.

용도

2-Pyrrolidinone is a widely used organic polar solvent for various applications. 2-Pyrrolidinone is also an intermediate in the manufacture of polymers.

정의

ChEBI: 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 gamm -aminobutyric acid (GABA).

생산 방법

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).

생산 방법

Pyrrolidone is prepared from butyrolactone by a Reppe process, in which acetylene is reacted with formaldehyde.

건강위험

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).

Pharmaceutical Applications

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.

공업 용도

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).

Safety

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

효소 저해제

This toxic lactam (FW = 85.106 g/mol), also called 2-pyrrolidinone, is soluble in water and many organic solvents. Target(s): cholinesterase, weakly inhibited; prolyl-tRNA synthetase; and pyroglutamylpeptidase I.

신진 대사

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).

저장

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.

비 호환성

Pyrrolidone is incompatible with oxidizing agents and strong acids.

2-피롤리디논 준비 용품 및 원자재

원자재

준비 용품


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