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N-메틸-2-피롤리디논

N-메틸-2-피롤리디논
N-메틸-2-피롤리디논 구조식 이미지
카스 번호:
872-50-4
한글명:
N-메틸-2-피롤리디논
동의어(한글):
1-메틸-2-피롤리딘온;1-메틸피롤리딘온;M-피롤;N-메틸피롤리돈;N-메틸피롤리딘온;피롤-M;1-메틸-2-피롤리디논;1-메틸피롤리돈;2-피롤리돈-메틸-;N-메틸-2-피롤리돈;N-메틸-2-피롤리디논;N-메틸피로리돈;엔엠피(NMP)중국;엔엠피(N.M.P)-공업용
상품명:
1-Methyl-2-pyrrolidinone
동의어(영문):
NMP;NMP-T;0131;NMP-EL;N-0131;M-Pyrol;gsolex 1;m-Pyrrole;AgsolEx 1;M-PYROL(R)
CBNumber:
CB2402488
분자식:
C5H9NO
포뮬러 무게:
99.13106
MOL 파일:
872-50-4.mol

N-메틸-2-피롤리디논 속성

녹는점
−24 °C(lit.)
끓는 점
202 °C(lit.)
밀도
1.028 g/mL at 25 °C(lit.)
증기 밀도
3.4 (vs air)
증기압
0.29 mm Hg ( 20 °C)
굴절률
n20/D 1.479
인화점
187 °F
저장 조건
2-8°C
용해도
ethanol: miscible0.1ML/mL, clear, colorless (10%, v/v)
물리적 상태
Liquid
색상
≤20(APHA)
수소이온지수(pH)
8.5-10.0 (100g/l, H2O, 20℃)
폭발한계
1.3-9.5%(V)
수용성
>=10 g/100 mL at 20 ºC
감도
Hygroscopic
최대 파장(λmax)
283nm(MeOH)(lit.)
Merck
14,6117
BRN
106420
안정성
Stable, but decomposes upon exposure to light. Combustible. Incompatible with strong oxidizing agents, strong acids, reducing agents, bases.
InChIKey
SECXISVLQFMRJM-UHFFFAOYSA-N
CAS 데이터베이스
872-50-4(CAS DataBase Reference)
NIST
2-Pyrrolidinone, 1-methyl-(872-50-4)
EPA
2-Pyrrolidinone, 1-methyl-(872-50-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,Xi
위험 카페고리 넘버 45-65-36/38-36/37/38-61-10-46
안전지침서 41-45-53-62-26
유엔번호(UN No.) UN 1268 3/PG 3
WGK 독일 1
RTECS 번호 UY5790000
F 고인화성물질 3-8-10
자연 발화 온도 518 °F
TSCA Y
HS 번호 29339900
유해 물질 데이터 872-50-4(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 3598 mg/kg LD50 dermal Rabbit 8000 mg/kg
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H227 가연성 액체 인화성 액체 구분 4 경고 P210, P280, P370+P378, P403+P235,P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H360 태아 또는 생식능력에 손상을 일으킬 수 있음 생식독성 물질 구분 1A, 1B 위험
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.

N-메틸-2-피롤리디논 C화학적 특성, 용도, 생산

화학적 성질

colourless or light yellow liquid with an amine odour

화학적 성질

l-Methyl-2-pyrrolidone 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. l-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).

용도

It 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.

정의

ChEBI: 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.

생산 방법

l-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.

일반 설명

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.

공기와 물의 반응

Soluble in water.

반응 프로필

This amine is a very mild chemical base. 1-Methyl-2-pyrrolidinone 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.

위험도

Severe skin and eye irritant. Explosive lim-its 2.2–12.2%.

건강위험

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.

화재위험

Special Hazards of Combustion Products: Toxic oxides of nitrogen may be formed in fire.

공업 용도

l-Methyl-2-pyrrolidone is used: 1) 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; and 6) for pesticide formulations (USEPA 1985).
Other non-industrial uses of l-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 l-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). l-Methyl-2-pyrrolidone has been approved as a solvent for slimicide application to food packaging materials (USDA 1986).

색상 색인 번호

1-Methylpyrrolidone 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.

Safety Profile

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.

신진 대사 경로

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.

신진 대사

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).

Purification Methods

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.]

N-메틸-2-피롤리디논 준비 용품 및 원자재

원자재

준비 용품


N-메틸-2-피롤리디논 공급 업체

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