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피리딘

피리딘
피리딘 구조식 이미지
카스 번호:
110-86-1
한글명:
피리딘
동의어(한글):
피리딘;아자벤젠;아진
상품명:
Pyridine
동의어(영문):
AA;PY;PYR;cp32;Azine;Piridina;Pirydyna;PYRIDINE;FEMA 2966;FEMA 2932
CBNumber:
CB8852825
분자식:
C5H5N
포뮬러 무게:
79.1
MOL 파일:
110-86-1.mol

피리딘 속성

녹는점
-42 °C
끓는 점
96-98 °C(lit.)
밀도
0.983 g/mL at 20 °C
증기 밀도
2.72 (vs air)
증기압
23.8 mm Hg ( 25 °C)
굴절률
n20/D 1.509(lit.)
FEMA
2966 | PYRIDINE
인화점
68 °F
저장 조건
Store at RT.
용해도
H2O: in accordance
산도 계수 (pKa)
5.25(at 25℃)
물리적 상태
Liquid
색상
colorless
상대극성
0.302
수소이온지수(pH)
8.81 (H2O, 20℃)
냄새
Nauseating odor detectable at 0.23 to 1.9 ppm (mean = 0.66 ppm)
폭발한계
12.4%
수용성
Miscible
어는점
-42℃
최대 파장(λmax)
λ: 305 nm Amax: 1.00
λ: 315 nm Amax: 0.15
λ: 335 nm Amax: 0.02
λ: 350-400 nm Amax: 0.01
Merck
14,7970
BRN
103233
노출 한도
TLV-TWA 5 ppm (~15 mg/m3) (ACGIH, MSHA,and OSHA); STEL 10 ppm (ACGIH), IDLH 3600 ppm (NIOSH).
안정성
Stable. Flammable. Incompatible with strong oxidizing agents, strong acids.
InChIKey
JUJWROOIHBZHMG-UHFFFAOYSA-N
CAS 데이터베이스
110-86-1(CAS DataBase Reference)
NIST
Pyridine(110-86-1)
EPA
Pyridine(110-86-1)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N,F,Xn
위험 카페고리 넘버 11-20/21/22-39/23/24/25-23/24/25-52-36/38
안전지침서 36/37/39-38-45-61-28A-26-28-24/25-22-36/37-16-7
유엔번호(UN No.) UN 1282 3/PG 2
WGK 독일 2
RTECS 번호 UR8400000
F 고인화성물질 3-10
자연 발화 온도 482 °C
위험 참고 사항 Highly Flammable/Harmful
TSCA Yes
HS 번호 2933 31 00
위험 등급 3
포장분류 II
유해 물질 데이터 110-86-1(Hazardous Substances Data)
독성 LD50 orally in rats: 1.58 g/kg (Smyth)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 삼키면 유독함 급성 독성 물질 - 경구 구분 3 위험 P264, P270, P301+P310, P321, P330,P405, P501
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H311 피부와 접촉하면 유독함 급성 독성 물질 - 경피 구분 3 위험 P280, P302+P352, P312, P322, P361,P363, P405, P501
H312 피부와 접촉하면 유해함 급성 독성 물질 - 경피 구분 4 경고 P280,P302+P352, P312, P322, P363,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
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H332 흡입하면 유해함 급성 독성 물질 흡입 구분 4 경고 P261, P271, P304+P340, P312
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P311 의료기관(의사)의 진찰을 받으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
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.
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P403+P235 환기가 잘 되는 곳에 보관하고 저온으로 유지하시오.

피리딘 C화학적 특성, 용도, 생산

물성

약한 염기성을 가지고 있으므로 산에는 염을 만들며 녹는다. 물 ·에탄올 ·에테르와 섞인다. 콜타르를 묽은 황산으로 처리하면 수용액이 되어 분리된다.

용도

피리딘은 다양한 공업적 용도로 사용되는 화합물이다. 주요한 분야로는 제초제와 고엽제가 있다. 파라쾃(paraquat)은 피리딘으로부터 합성되는 초강력 제초제다. 아예 환원시켜서 비방향족 헤테로고리 화합물인 피페리딘을 합성하는데 사용되기도 한다. 그 외에 드물게 유기용매로 사용되기도 하고, 유기금속화학분야에서 유용한 고부가가치 화합물을 합성하는데 리간드로 이용되기도 한다. 여담이지만 니코틴 분자를 구성하는 주요 파트를 이루기도 한다. 오각형 비방향족 헤테로고리 화합물인 N-메틸피롤리딘과 연결된 형태가 바로 니코틴이다. 파란색이 피리딘 파트.

용도

고무나 도료의 용제로 사용되며, 합성원료 ·분석시약으로도 사용된다.

화학적 성질

Pyridine, C5H5N, is a yellowish, flammable, poisonous organic solvent with a very distinctive and penetrating odor. Pyridine is soluble in water, alcohol, benzene, and ether.It has a boiling point of 116°C (240 OF). Pyridine is used in paints,medicine,and textile dyeing.

화학적 성질

Pyridine is a colorless liquid. Nauseating, sickening fish-like odor. The Odor Threshold is 0.17 ppm.

화학적 성질

Pyridine is a weak base (pKa= 5.25); a 0.2 M solution has a pH of 8.5 (HSDB 1988). Its carbon atoms are deactivated towards electrophilic substitution. This is especially true in acidic media, where salts form at the nitrogen. It does, however, readily undergo nucleophilic substitution, preferentially at the C-2 and also at the C-4 position (Jori et al 1983). Being a tertiary amine, pyridine reacts with alkylating agents to form quaternary salts (Santodonato et al 1985). Because of its reduced capacity to donate electrons, it is more resistant to oxidation than benzene. Oxidation with peroxy acids forms pyridine N-oxide which is then capable of undergoing electrophilic substitution (Jori et al 1983). Pyridine reacts violently with a number of compounds, including nitric acid, sulfuric acid, maleic anhydride, perchromate, beta-propiolactone and chlorosulfonic acid. Thermal decomposition can liberate cyanides (Gehring 1983). Both the pyridinium ion and pyridine itself are readily reduced to the commercially important compound, piperidine (Jori et al 1983).

화학적 성질

Pyridine has a characteristic, penetrating odor and a sharp taste.

출처

Pyridine was discovered by Anderson in coal tar in 1846 (Windholz et al 1983). It is found in tobacco smoke (Vohl and Eulenberg 1871; Lehmann 1909) and roasted coffee (Bertrand and Weisweiller 1913). Pyridine is found in wood oil and in the leaves and roots of Atropa belladonna (HSDB 1988), and is also a component of creosote oil (Krone et al 1986).

용도

Used as solvent; complexing agent.

용도

As solvent for Anhydrous mineral salts. Synthetic intermediate in laboratory and industry.

용도

Pyridine is used as a solvent in paint andrubber industries; as an intermediate in dyesand pharmaceuticals; for denaturing alcohol;and as a reagent for cyanide analysis. Itoccurs in coal tar.

제조 방법

From coal tar distillation

정의

ChEBI: An azaarene comprising a benzene core in which one -CH group is replaced by a nitrogen atom. It is the parent compound of the class pyridines.

정의

An organic liquid of formula C5H5N. The molecules have a hexagonal planar ring and are isoelectronic with benzene. Pyridine is an example of an aromatic heterocyclic compound, with the electrons in the carbon–carbon pi bonds and the lone pair of the nitrogen delocalized over the ring of atoms. The compound is extracted from coal tar and used as a solvent and as a raw material for organic synthesis.

정의

azine: An organic heterocyclic compoundcontaining a six-memberedring formed from carbon and nitrogenatoms. Pyridine is an examplecontaining one nitrogen atom(C5H5N). Diazines have two nitrogenatoms in the ring (e.g. C4H4N2), andisomers exist depending on the relativepositions of the nitrogen atoms.Triazines contain three nitrogenatoms.

정의

pyridine: A colourless liquid with astrong unpleasant smell, C5H5N (seeformula); r.d. 0.98; m.p. –42°C; b.p.115°C. Pyridine is an aromatic heterocycliccompound present in coaltar. It is used in making other organicchemicals.

생산 방법

Pyridine is produced from the gases obtained by the coking of coal and by direct synthesis. The light-oil fraction of coal tar is treated with sulfuric acid to produce water-soluble pyridine salts and then the pyridine bases are recovered from the aqueous phase by sodium hydroxide or ammonia (Jori et al 1983). The majority of U.S. production is through synthetic means. This process uses a vapor-phase reaction of acetaldehyde, formaldehyde and ammonia, which yields a mixture of pyridine and 3-methylpyridine (Santodonato et al 1985). The product ratio depends on the relative amounts of acetaldehyde and formaldehyde. Added methanol increases the yield. The U.S. production of pyridine was estimated at 32 to 47 million pounds in 1975 (Reinhardt and Brittelli 1981). Pyridine is commercially available in technical, 2° and 1° grades, the latter two referring to their boiling ranges. Major impurities are higher boiling homologues, such as picolines, lutidines and collidines, which are mono-, di-, and trimethylpyridines (Santodonato et al 1985; Jori et al 1983).

Aroma threshold values

Detection: 0.079 to 790 ppb; recognition: 7.9 to 40 ppm

일반 설명

A clear colorless to light yellow liquid with a penetrating nauseating odor. Density 0.978 g / cm3. Flash point 68°F. Vapors are heavier than air. Toxic by ingestion and inhalation. Combustion produces toxic oxides of nitrogen.

공기와 물의 반응

Highly flammable. Soluble in water.

반응 프로필

Azabenzene is a base. Reacts exothermically with acids. During preparation of a complex of Azabenzene with chromium trioxide, an acid, the proportion of chromium trioxide was increased. Heating from this acid-base reaction led to an explosion and fire [MCA Case History 1284 1967]. A 0.1% solution of Azabenzene (or other tertiary amine) in maleic anhydride at 185°C gives an exothermic decomposition with rapid evolution of gas [Chem Eng. News 42(8); 41 1964]. Mixing Azabenzene in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, nitric acid (70%), oleum, sulfuric acid (96%), or propiolactone [NFPA 1991]. The combination of iodine, Azabenzene, sulfur trioxide, and formamide developed a gas over pressurization after several months. This arose from the slow formation of sulfuric acid from external water, or from dehydration of the formamide to hydrogen cyanide. Ethylene oxide and SO2 can react violently in Azabenzene solution with pressurization if ethylene oxide is in excess (Nolan, 1983, Case History 51).

위험도

Flammable, dangerous fire risk, explosive limits in air 1.8–12.4%. Toxic by ingestion and inhalation. Skin irritant, liver and kidney damage. Questionable carcinogen.

건강위험

The acute toxicity of pyridine is low. Inhalation causes irritation of the respiratory system and may affect the central nervous system, causing headache, nausea, vomiting, dizziness, and nervousness. Pyridine irritates the eyes and skin and is readily absorbed, leading to systemic effects. Ingestion of pyridine can result in liver and kidney damage. Pyridine causes olfactory fatigue, and its odor does not provide adequate warning of the presence of harmful concentrations.
Pyridine has not been found to be carcinogenic or to show reproductive or developmental toxicity in humans. Chronic exposure to pyridine can result in damage to the liver, kidneys, and central nervous system.

건강위험

Vapor irritates eyes and nose. Liquid irritates skin and is absorbed through the skin. Overexposure causes nausea, headache, nervous symptoms, increased urinary frequency.

건강위험

The toxic effects of pyridine include headache,dizziness, nervousness, nausea, insomnia,frequent urination, and abdominal pain.The symptoms were transient, occurred inpeople from subacute exposure to pyridinevapors at about 125 ppm for 4 hours a dayfor 1–2 weeks (Reinhardt and Brittelli 1981).The target organs to pyridine toxicity are thecentral nervous system, liver, kidneys, gastrointestinaltract, and skin.
The routes ofexposure are inhalation of vapors, and ingestionand absorption of the liquid throughthe skin. Serious health hazards may arisefrom chronic inhalation, which may causekidney and liver damage, and stimulationof bone marrow to increase the productionof blood platelets. Low-level exposureto 10 ppm may produce chronic poisoningeffects on the central nervous system. Ingestionof the liquid may produce the samesymptoms as those stated above. Skin contactcan cause dermatitis. Vapor is an irritantto the eyes, nose, and lungs. Because of itsstrong disagreeable odor, there is always asufficient warning against any overexposure.A concentration of 10 ppm is objectionableto humans.
LCLO value, inhalation (rats): 4000 ppm/4 h
LD50 value, oral (mice): 1500 mg/kg.
Huh and coworkers (1986) have investigatedthe effect of glycyrrhetinic acid on pyridine toxicity in mice. Pretreatmentwith glycyrrhetinic acid decreaseddepression of the central nervous system andmortality in animals induced by pyridine.Such pretreatment markedly decreased theactivity of the enzyme serum transaminase, and increased the activity of hepaticmicrosomal aniline hydroxylase [9012-90-0], a pyridine- metabolizing enzyme.

건강위험

The toxic effects of pyridine are mainly centered on the central nervous system (CNS), gastrointestinal (GI) tract, liver and kidneys. When men were treated orally with 1.8-2.5 ml of pyridine daily for up to two months, in an aborted attempt at Northwestern University to treat epilepsy, they experienced anorexia, nausea, vomiting, gastric distress, headache, fatigue, faintness and depression (Pollock et al 1943). Two cases of liver and kidney damage and one death occurred. Another reported fatality was caused by the accidental swallowing of one-half cup of commercial pyridine. The patient experienced abdominal pain, inability to swallow, lung congestion and bronchitis and died two d later (Helme 1893; Pollock et al 1943). The probable oral lethal dose is 0.5-5.0 g/kg (HSDB 1988) and a LDLo dose for man was 500 mg/kg p.o. (Jori et al 1983). Exposures to doses that are too low to produce overt clinical symptoms can cause hepatic damage and repeated low-level exposures can cause cirrhosis (Gehring 1983). Many of the cases of human poisoning have been due to inhalation of pyridine vapor. The vapor is irritating to mucous surfaces and causes eye and nasal irritation (HSDB 1988). Chronic exposures of 6-13 p.p.m. have caused toxic effects related to both the CNS and GI tract, such as headache, vertigo, nervousness, insomnia, nausea and vomiting. Other symptoms caused by pyridine vapor include abdominal or lower back pain with urinary frequency and nervous system affliction with speech disorders (Reinhardt and Brittelli 1981; HSDB 1988). The maximum long-term exposure is estimated to be 1-5 p.p.m. (Santodonato 1985; Teisinger 1948).

화재위험

Behavior in Fire: Vapor is heavier than air and may travel considerable distance to source of ignition and flash back.

화재위험

Pyridine is a highly flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance and "flash back." Pyridine vapor forms explosive mixtures with air at concentrations of 1.8 to 12.4% (by volume). Carbon dioxide or dry chemical extinguishers should be used for pyridine fires.

인화성 및 폭발성

Pyridine is a highly flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance and "flash back." Pyridine vapor forms explosive mixtures with air at concentrations of 1.8 to 12.4% (by volume). Carbon dioxide or dry chemical extinguishers should be used for pyridine fires.

공업 용도

Pyridine is a good solvent for a large number of compounds, both organic and inorganic (Windholz et al 1983). About 50% of pyridine used in the U.S. is for the production of agricultural chemicals, such as the herbicides paraquat, diquat and triclopyr and the insecticide chlorpyrifos. Other uses are in the production of piperidine; the manufacture of pharmaceuticals, such as steroids, vitamins and antihistamines; and as a solvent. Solvent uses are found in both the pharmaceutical and polycarbonate resin industries. It is particularly useful as a solvent in processes where HC1 is evolved (Santodonato et al 1985). Minor uses for pyridine are for the denaturation of alcohol and antifreeze mixtures, as a dyeing assistant in textiles and as a flavoring agent (Jori et al 1983; Furia 1968; HSDB 1988).

색상 색인 번호

Pyridine (unsubstituted pyridine) and its derivative (substituted pyridines) are widely used in chemistry. Pyridine is a solvent used for many organic compounds and anhydrous metallic salt chemicals. Contained in Karl Fischer reagent, it induced contact dermatitis in a laboratory technician. No cross-sensitivity is observed between those different substances.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion, skin contact, intravenous, and subcutaneous routes. Mildly toxic by inhalation. A skin and severe eye irritant. Mutation data reported. Can cause central nervous system depression, gastrointestinal upset, and liver and kidney damage. A flammable liquid and dangerous fire hazard when exposed to heat, flame, or oxidizers. Severe explosion hazard in the form of vapor when exposed to flame or spark. Reacts violently with chlorosulfonic acid, chromium trioxide, dinitrogen tetraoxide, HNO3, oleum, perchromates, ppropiolactone, AgClO4, H2SO4. Incandescent reaction with fluorine. Reacts to form pyrophoric or explosive products with bromine trifluoride, trifluoromethyl hypofluorite. Mixtures with formamide + iodine + sulfur trioxide are storage hazards, releasing carbon dioxide and sulfuric acid. Incompatible with oxidizing materials. Reacts with maleic anhydride (above 150°C) evolving carbon dioxide. To fight fire, use alcohol foam. When heated to decomposition it emits highly toxic fumes of NOx.

잠재적 노출

Pyridine is used as a solvent in the chemical industry and as a denaturant for ethyl alco- hol; as an intermediate in the production of pesticides; in pharmaceuticals; in the manufacture of paints, explosives, dyestuffs, rubber, vitamins, sulfa drugs; and disinfectants.

효소 저해제

This aromatic nitrogen heterocycle (FW = 79.101 g/mol; CAS 110-86-1; colorless; M.P. = –41.5° C; B.P. = 115.25° C; unpleasant odor; weak base; pKa = 5.23 at 25° C, with dpKa/dT = –0.014) has many uses in organic synthesis and analytical chemistry. Pyridine should only be used in a fume hood or where there is sufficient ventilation. Miscible with water, pyridine has a larger dipole moment (2.37 versus 1.87 for water), and a dielectric constant of 12.4 (a sixth that of water). Target (s) : acid phosphatase; adenain; alcohol dehydrogenase; D-amino-acid oxidase, weakly inhibited; aromatase, or CYP19; carbonic anhydrase, or carbonate dehydratase, Ki ≈ 0.5 M; catechol 2,3-dioxygenase; chymotrypsin; dimethylaniline-N-oxide aldolase; glucose dehydrogenase, weakly inhibited; histidine decarboxylase, Ki = 1.4 mM; lipase, or triacylglycerol lipase; nicotinate phosphoribosyltransferase; and xyloglucan:xyloglucosyl transferase .

응급 처치

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, includ- ing resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

신진 대사

Pyridine is absorbed through the gastrointestinal tract, skin and lungs and is eliminated via the urine, feces, skin and lungs, both as metabolites and as the parent compound (Jori et al 1983). Uptake by tissues increases with dose and the elimination is biphasic in nature (Zharikov and Titov 1982; HSDB 1988). Elimination is rapid and there appears to be no tissue accumulation (Jori et al 1983). The observation by His (1887) of the urinary excretion of Af-methylpyridine by pyridine-dosed animals was the first example of Af-methylation. Known urinary metabolites of pyridine in mammals now include pyridine N-oxide, N-methyl pyridine, 4-pyridone, 2-pyridone and 3-hydroxypyridine. Some metabolites still remain to be identified (Damani et al 1982). The relative amounts of the metabolites are highly dependent on the species and dose (Gorrod and Damani 1980). For example, the rat has been shown to excrete 70% of a 1 mg/kg dose in the urine in the first 24 h after dosing, but that figure drops to only 5.8% for a 500 mg/kg dose (D'Souza et al 1980). Although urinary excretion of pyridine and its metabolites appears to be a major route for elimination, non-urinary excretion has not been extensively studied (Santodonato et al 1985). In rabbits, the pyridine N-methyltransferase activity has been shown to be highest in lung cytosol and it has been found to utilize 5-adenosyl methionine as the methyl donor (Damani et al 1986). This pathway is saturable in both the rat and the guinea pig (D'Souza et al 1980). The product of this reaction, N-methyl pyridine, is less chronically toxic but more acutely toxic than pyridine (Williams 1959). Pyridine N-oxide is produced by the cytochrome P-450 system and the activity is induced by phenobarbital or pyridine pretreatment but not by 3-methylcholanthrene (Gorrod and Damani 1979; Kaul and Novak 1987). In the rabbit, the alcohol-inducible (and pyridine inducible) P-450 LM3A appears to be the low Km isozyme which catalyzes pyridine Af-oxide production (Kim and Novak 1989). The N-oxidation of pyridine may represent a pathway for bioactivation (Santodonato et al 1985) and this pathway becomes more important as the pyridine dose is increased (Damani et al 1982).

저장

Pyridine should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

운송 방법

UN1992 Flammable liquids, toxic, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous mate- rials, Technical Name Required.

Purification Methods

Likely impurities are H2O and amines such as the picolines and lutidines. Pyridine is hygroscopic and is miscible with H2O and organic solvents. It can be dried with solid KOH, NaOH, CaO, BaO or sodium, followed by fractional distillation. Other methods of drying include standing with Linde type 4A molecular sieves, CaH2 or LiAlH4, azeotropic distillation of the H2O with toluene or *benzene, or treated with phenylmagnesium bromide in ether, followed by evaporation of the ether and distillation of the pyridine. A recommended [Lindauer & Mukherjee Pure Appl Chem 27 267 1971] method dries pyridine over solid KOH (20g/Kg) for 2weeks and fractionally distils the supernatant over Linde type 5A molecular sieves and solid KOH. The product is stored under CO2-free nitrogen. Pyridine can be stored in contact with BaO, CaH2 or molecular sieves. Non-basic materials can be removed by steam distilling a solution containing 1.2 equivalents of 20% H2SO4 or 17% HCl until about 10% of the base has been carried over along with the non-basic impurities. The residue is then made alkaline, and the base is separated, dried with NaOH and fractionally distilled. Alternatively, pyridine can be treated with oxidising agents. Thus pyridine (800mL) has been stirred for 24hours with a mixture of ceric sulfate (20g) and anhydrous K2CO3 (15g), then filtered and fractionally distilled. Hurd and Simon [J Am Chem Soc 84 4519 1962] stirred pyridine (135mL), water (2.5L) and KMnO4 (90g) for 2hours at 100o, then stood for 15hours before filtering off the precipitated manganese oxides. Addition of solid KOH (ca 500g) caused pyridine to separate. It was decanted, refluxed with CaO for 3hours and distilled. Separation of pyridine from some of its homologues can be achieved by crystallisation of the oxalates. Pyridine is precipitated as its oxalate by adding it to the stirred solution of oxalic acid in acetone. The precipitate is filtered, washed with cold acetone, and pyridine is regenerated and isolated. Other methods are based on complex formation with ZnCl2 or HgCl2. Heap, Jones and Speakman [J Am Chem Soc 43 1936 1921] added crude pyridine (1L) to a solution of ZnCl2 (848g) in 730mL of water, 346mL of conc HCl and 690mL of 95% EtOH. The crystalline precipitate of ZnCl2.(pyridine)2 was filtered off, recrystallised twice from absolute EtOH, then treated with a conc NaOH solution, using 26.7g of solid NaOH to 100g of the complex. The precipitate was filtered off, and the pyridine was dried with NaOH pellets and distilled. Similarly, Kyte, Jeffery and Vogel [J Chem Soc 4454 1960] added pyridine (60mL) in 300mL of 10% (v/v) HCl to a solution of HgCl2 (405g) in hot water (2.3L). On cooling, crystals of pyridine-HgCl2 (1:1) complex separated and were filtered off, crystallised from 1% HCl (to m 178.5-179o), washed with a little EtOH and dried at 110o. The free base was liberated by addition of excess aqueous NaOH and separated by steam distillation. The distillate was saturated with solid KOH, and the upper layer was removed, dried further with KOH, then BaO and distilled. Another possible purification step is fractional crystallisation by partial freezing. Small amounts of pyridine have been purified by vapour-phase chromatography, using a 180-cm column of polyethyleneglycol-400 (Shell 5%) on Embacel at 100o, with argon as carrier gas. The Karl Fischer titration can be used for determining water content. A colour test for pyrrole as a contaminant is described by Biddiscombe et al. [J Chem Soc 1957 1954]. The 1:1-hydrochloride crystallises from EtOH with m 144o, b 218-219o/760mm (see below) and is hygroscopic. The 1:2-hydrochloride has m 46o [58888-58-7] and the picrate has m 165-166o [1152-90-5]. [Beilstein 20 H 181, 20 I 54, 20 II 96, 20 III/IV 2205, 20/5 V 160.] § Polystyrene-supported pyridine is commercially available.

비 호환성

Violent reaction with strong oxidizers; strong acids; chlorosulfonic acid; maleic anhydride; oleum iodine.

폐기물 처리

Controlled incineration whereby nitrogen oxides are removed from the effluent gas by scrubber, catalytic or thermal devices .

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