91-22-5 Usage
Description
Quinoline is a colourless hygroscopic liquid with characteristic odour. On exposure
to light, it turns brown in colour. Quinoline decomposes on heating, and on burning
produces toxic fumes including nitrogen oxides. Quinoline reacts with strong oxidants,
acids, and anhydrides. Quinoline is only slightly soluble in cold water but dissolves readily
in hot water and most organic solvents. Quinoline is combustible. It gives off irritating
or toxic fumes (or gases) in a fire. Quinoline is incompatible with strong acids, oxidisers,
dinitrogen tetroxide, linseed oil, thionyl chloride, maleic anhydride, and perchromates
and reacts violently with most incompatibles. Quinoline is used extensively in the manufacturing
of dyes, preparation of hydroxyquinoline sulphate and niacin, as a solvent for
resins and terpenes, and as an intermediate in the manufacture of other products.
Quinoline is used mainly as an intermediate in the manufacture of other several products,
as a catalyst, as a corrosion inhibitor, in metallurgical processes, in the manufacture of
dyes, as a preservative for anatomical specimens, in polymers and agricultural chemicals,
and as a solvent for resins and terpenes. Quinoline is also used as an anti-malarial medicine.
Because of its solubility in water, quinoline has significant potential for mobility in the
environment, which may promote water contamination. Potential exposure to quinoline
also occurs from the inhalation of cigarette smoke. Quinoline breaks down quickly in the
atmosphere and water.
Chemical Properties
Different sources of media describe the Chemical Properties of 91-22-5 differently. You can refer to the following data:
1. Quinoline is a colorless liquid with a penetrating
amine odor. Turns brown on exposure to light.
2. Quinoline has a heavy, penetrating and nauseating, yet sweet odor of good tenacity.
Occurrence
Quinoline was discovered in coal tar distillate in 1834 by Runge. It is released to
the environment through natural combustion processes and has been isolated from
air particulates (Dong et al 1977). Quinoline may be a significant aqueous
byproduct of synthetic fuel production (shale oil, coal processing) and from wood
preservation production and use facilities. Small amounts also have been detected
in tobacco smoke (Schmeltz and Hoffmann 1977).
Uses
Different sources of media describe the Uses of 91-22-5 differently. You can refer to the following data:
1. Preserving anatomical specimens; manufac-
ture of quinolinol sulfate; niacin and copper-8-
quinolinolate; flavoring.
2. Quinoline is used in the manufacture of dyesand hydroxyquinoline salts; as a solvent forresins and terpenes; and therapeutically as anantimalarial agent. It occurs in coal tar insmall amounts.
3. Quinoline is used as an intermediate in the production of
quinoline-related compounds (e.g., 8-hydroxyquinoline). Its
multiple uses include solvent, preservative, flavoring agent in
medicine, colorant in dyes and paints, and also a component of
some fungicides. It is also a solvent for resins and terpenes and
is used in the production of paint. Quinoline used as a coloring
additive in foods, such as Quinoline Yellow, has increased the
concern that quinoline that is found in these processes may contribute to the development of cancers later in life. Quinoline
is also an antimalarial agent. Sources of quinoline include
petroleum and coal processing, wood preservation, and the use
of shale oil.
Definition
Different sources of media describe the Definition of 91-22-5 differently. You can refer to the following data:
1. A
colorless two-ring heterocyclic compound
with an unpleasant odor, which acts as a
base and forms salts with acids. First made
from the alkaloid quinine, it is found in
bone oil and coal tar and used for making
drugs and dyestuffs.
2. quinoline: A hygroscopic unpleasant-smelling colourless oily liquid,C9H7N; b.p. 240°C. Its molecules consistof a benzene ring fused to a pyridinering. It occurs in coal tar andbone oil, and is made from phenylamineand nitrobenzene. Quinolineis a basic compound, forming saltswith mineral acids and forming quaternaryammonium compounds withhaloalkanes. It is used for makingmedicines and dyes. In quinoline, thenitrogen atom is one atom awayfrom the position at which the ringsare fused. In an isomer, isoquinoline,the nitrogen atom is positioned twoatoms away from the fused ring.
3. ChEBI: The simplest member of the quinoline class of compounds, comprising a benzene ring ortho fused to C-2 and C-3 of a pyridine ring.
Production Methods
Quinoline may be synthesized by heating aniline with glycerol and nitrobenzene in
sulfuric acid (Skraup method) or by reacting aniline, acetaldehyde, and a formaldehyde
hemiacetal (Windholz et al 1983). Commercial production is by isolation
from coal tar with greater than 100,000 lbs being produced in 1977. Production of
refined quinoline has almost ceased due to low demand (Parris et al 1983).
Aroma threshold values
Detection: 710 ppb
Taste threshold values
Taste characteristics at 2 to 10 ppm: earthy, musty, nutty, coumarinic with a chemical nuance.
Synthesis Reference(s)
Tetrahedron Letters, 29, p. 953, 1988 DOI: 10.1016/S0040-4039(00)82491-0Chemical and Pharmaceutical Bulletin, 26, p. 1015, 1978 DOI: 10.1248/cpb.26.1015
General Description
A colorless liquid with a peculiar odor. Slightly denser than water. Contact may irritate to skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
Reactivity Profile
Quinoline is hygroscopic. Quinoline absorbs as much as 22% water. Quinoline is sensitive to light and moisture. Quinoline darkens on storage. Quinoline is a weak base. A potentially explosive reaction may occur with hydrogen peroxide. Quinoline reacts violently with dinitrogen tetraoxide. Quinoline also reacts violently with perchromates. Quinoline is incompatible with (linseed oil + thionyl chloride) and maleic anhydride. Quinoline is also incompatible with strong oxidizers and strong acids. Quinoline can be unpredictably violent. Quinoline dissolves sulfur, phosphorus and arsenic trioxide. Quinoline may attack some forms of plastics. Quinoline is a preparative hazard.
Health Hazard
Different sources of media describe the Health Hazard of 91-22-5 differently. You can refer to the following data:
1. Vapors are irritating to nose and throat and may cause headaches, dizziness, and nausea if inhaled. Ingestion causes irritation of mouth and stomach; vomiting may occur. Contact with eyes or skin causes irritation.
2. No industrial injuries from quinoline exposure have been reported. Handling
precautions similar to those taken for pyridine are recommended (EOHS 1971).
Clinical signs of toxicity include lethargy, respiratory distress, and coma; cause
of death is respiratory paralysis.
Quinoline is a skin and eye irritant; it may cause permanent corneal injury
(EOHS 1971).
Routine occupational exposure to quinoline probably constitutes low risk for
acute toxicity. Long-term exposure to low concentrations may increase cancer
risk.
3. There is little information in the publishedliterature on the toxic properties of quinoline.The acute toxicity is moderate in rodentsfrom oral and dermal administration. Thereported oral LD50 values in rats showinconsistent values ranging between 300 and500 mg/kg. Its irritant action was mild onrabbits’ skin and severe in the animals’ eyes.Quinoline exhibited carcinogenicity inrats and mice, causing liver cancer. There isno evidence of its carcinogenicity in humans.It tested positive to the histidine reversion–Ames test for mutagenicity.
Flammability and Explosibility
Nonflammable
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: Attacks some forms of plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Industrial uses
Quinoline is used as a solvent for resins and terpenes. It also is used as an
antimalarial, an antioxidant, a catalyst and as an intermediate in the manufacture
of various products (Parris et al 1983).
Safety Profile
Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic by skin contact. A skin and severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. It can cause retinitis sdar to that caused by naphthalene but without causing opacity of the lens. Combustible when exposed to heat or flame. Its preparation has caused many industrial explosions. Potentially explosive reaction with hydrogen peroxide. Violent reaction with dmtrogen tetraoxide, perchromates. Incompatible with linseed oil + thionyl chloride, maleic anhydride, Unpredctably violent. When heated to decomposition it emits toxic fumes of NOx.
Potential Exposure
In manufacture of quinoline deriva-
tives (dyes and pesticides); in synthetic fuel manufacture.
Occurs in cigarette smoke.
Carcinogenicity
Liver tumors were observed in
rats administered diets containing 0.05–0.25% quinoline.
The incidence of hepatocellular carcinomas was 3/11 at
0.05%, 3/16 at 0.1%, and 0/19 at 0.25% versus 0/6 in controls.
At 0.25%, most of the rats died within 40 weeks. The
incidences of hemangioendotheliomas were 6/11, 12/16,
18/19, and 0/6, respectively. Hepatocellular carcinomas
and hemangioendotheliomas were seen in livers of rats
fed 500, 1000, or 2500 ppm for 16–40 weeks. Typical
hyperplasias were also observed in the liver.
Environmental Fate
biodegradative processes occur under aerobic conditions. Anaerobic degradation
is minimal (Mill et al 1981). Breakdown of quinoline in natural waters has been
correlated with bacterial concentration (Rogers et al 1984). Adsorption was high in
acidic soils (pH<6) and low in basic soils (pH>7). The presence of pyridine
decreased quinoline adsorption on acidic, but not basic, soils. Sorption did not
correlate with organic carbon or clay content (Felice et al 1984). Soil bacteria have
been grown with quinoline as the sole carbon source (Grant and Al-Najjar 1976).
Quinoline did not bioconcentrate to a significant extent in fathead minnows
(Southworth et al 1980).
Shipping
UN2656 Quinoline, Hazard Class: 6.1; Labels:
6.1-Poisonous materials.
Purification Methods
Dry quinoline with Na2SO4 and distil it from zinc dust in a vacuum. It has also been dried by boiling with acetic anhydride, then fractionally distilled. Calvin and Wilmarth [J Am Chem Soc 78 1301 1956] cooled redistilled quinoline in ice and added enough HCl to form its hydrochloride. Diazotization removed aniline, the diazo compound being broken down by warming the solution to 60o. Non-basic impurities were removed by ether extraction. Quinoline was then liberated by neutralising the hydrochloride with NaOH, then dried with KOH and fractionally distilled at low pressure. Addition of cuprous acetate (7g/L of quinoline) and shaking under hydrogen for 12hours at 100o removed impurities due to the nitrous acid treatment. Finally the hydrogen was pumped off, and the quinoline was distilled. Other purification procedures depend on conversion to the phosphate (m 159o, precipitated from MeOH solution, filtered, washed with MeOH, then dried at 55o) or the picrate (m 201o) which, after recrystallisation, were reconverted to quinoline. The method using the picrate [Packer et al. J Am Chem Soc 80 905 1958] is as follows: quinoline is added to picric acid dissolved in the minimum volume of 95% EtOH, giving yellow crystals which were washed with EtOH, air-dried and crystallised from acetonitrile. These were dissolved in dimethyl sulfoxide (previously dried over 4A molecular sieves) and passed through a basic alumina column, onto which the picric acid is adsorbed. The free base in the effluent is extracted with n-pentane and distilled under vacuum. Traces of solvent can be removed by vapour-phase chromatography. [Moonaw & Anton J Phys Chem 80 2243 1976.] The ZnCl2 and dichromate complexes have also been used [Cumper et al. J Chem Soc 1176 1962]. [Beilstein 20 H 339, 20 I 134, 20 II 222, 20 III/IV 3334, 20/7 V 276.]
Toxicity evaluation
Quinoline undergoes Phase I metabolism to form an enamine
oxide, a rapid transitional epoxide, which can then form DNA
adducts. This epoxide is formed on the pyridine moiety of
quinoline. Fluorination at position 3 completely prevents the
mutagenicity of quinoline. The major metabolic enzyme is the
CYP2E1 isoform with the primary end product from this
reaction being 3-hydroxyquinoline. Refer to the sections on ‘Genotoxicity’ and ‘Carcinogenicity’ for more specific descriptions
of quinoline toxicity. The primary and most severe, toxic
outcome following quinoline exposure is genotoxicity followed
by tumor formation.
Incompatibilities
Reacts, possibly violently, with strong
oxidants, strong acids; perchromates, nitrogen tetroxide;
and maleic anhydride. Keep away from moisture, steam,
and light. Contact with hydrogen peroxide may cause
explosion. Unpredictably violent, this substance has been
the source of various plant accidents.
Check Digit Verification of cas no
The CAS Registry Mumber 91-22-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 91-22:
(4*9)+(3*1)+(2*2)+(1*2)=45
45 % 10 = 5
So 91-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
91-22-5Relevant articles and documents
Microwaves under pressure for the continuous production of quinoline from glycerol
Saggadi,Polaert,Luart,Len,Estel
, p. 66 - 74 (2015)
Abstract Microwave heating is an interesting technology for chemical engineering, since it can provide effective volumetric heating of the reaction medium and reduce energy costs. Many commercially available laboratory-scale microwave reactors have already been used to carry out chemical reactions on a small scale (a few milliliters), and at high temperatures and pressures. Some research has been undertaken to scale-up microwave processes and make them suitable for a larger scale production. Indeed, combining wave propagation through the walls of a reactor with resistance toward high pressure and temperature as well, is not an easy task. For these reasons, this work focuses on the development of a pilot scale microwave apparatus used for the heating of larger reaction volumes under pressure, and under controlled conditions. The specially designed microwave apparatus allows chemical reactions in batch or continuous mode. The applicator operates in single mode enabling a uniform electromagnetic field, and well controlled operating conditions. The main advantage of the setup is the quite large reactor volume that permits either relatively long residence times or relatively high mass flowrates (up to 1 kg/h). The developed microwave apparatus was then used for quinoline synthesis from glycerol via a modified Skraup reaction. The major advantage of our system is the ability to carry out continuous chemical synthesis, at a large pilot scale, and high temperatures (200-220 °C), while ensuring a better control of the pressure (max. 19 bar) through the control of the power absorbed by the reaction medium.
Copper-Catalyzed Direct Oxidative α-Functionalization of Tetrahydroquinoline in Water under Mild Conditions
Ramana, Daggupati V.,Chandrasekharam, Malapaka
, p. 4080 - 4083 (2018)
An efficient one-step α-functionalization of tetrahydroquinoline under mild conditions is achieved. The direct oxidative copper-catalyzed dehydrogenative cross C(sp3)?C(sp2) couplings of tetrahydroquinolines and indoles produced the products in aqueous and open air medium. The use of inexpensive copper catalyst, water solvent, easy to operate open air condition combined with the most step and atom economic features qualify the CDC reaction for a green process. (Figure presented.).
A Novel Gemini Sulfonic Ionic Liquid Immobilized MCM-41 as Efficient Catalyst for Doebner-Von Miller Reaction to Quinoline
Li, An,Wang, Xinyang,Li, Yuhang,Luo, Caiwu,Zhang, Jiance,Liu, Kun,Zhang, Cen,Zhou, Congshan
, p. 3772 - 3780 (2021)
A novel 2,2′-bipyridine-based gemini sulfonic ionic liquid was first synthesized and then immobilized on MCM-41 support (named IL1/MCM-41), which was further characterized using XRD, FT-IR, SEM, TEM, N2-physisorption, XPS and TG techniques. These characterization results revealed that the IL1/MCM-41 presented a whole ordered mesoporous structure, excellent thermal stability as well as the interaction between ionic liquid with MCM-41. Catalytic activity of the obtained IL1/MCM-41 was systematically evaluated for the Doebner-Von Miller reaction to generate quinoline. Compared to conventional imidazole-type single sulfonic ionic liquid supported on MCM-41 (named IL2/MCM-41), IL1/MCM-41 exhibited higher catalytic activity and better reusability, which was probably due to the synergistic catalytic effect of the dual sulfonic acid group on IL2 and the stronger interaction between dipyridine ring of ionic liquid with MCM-41 support, respectively. Meanwhile, a plausible reaction routes for the synergistic catalytic action of dual sulfonic acid to quinoline over the IL1/MCM-41 catalyst was also proposed in this paper.
-
Closs,Schwartz
, p. 2609 (1961)
-
Zn-promoted Hβ zeolite for gas-phase catalyzed aza-heterocyclic-aromatization of acrolein dimethyl acetal and aniline to quinolines
Li, An,Li, Lijun,Lin, Ying,Liu, Kun,Liu, Yong,Luo, Caiwu,Zhou, Congshan
, (2020)
Catalytic activities of Zn-promoted Hβ zeolite for gas-phase aza-heterocyclic-aromatization of acrolein dimethyl acetal and aniline to quinolines were investigated. the Zn/Hβ catalyst showed better selectivity to quinoline than the parent Hβ one. Characterization results demonstrated that the Zn/Hβ catalyst prepared via deposition precipitation method existed the isolated Zn2+ cations as well as the highly dispersed ZnO clusters, which not only decreased concentration of strong acid sites but also enhanced enhance aromatization process. As a result, the decrease of strong acid sites restrained the cracking of acrolein to acetaldehyde as well as the alkylation of quinoline to ethylquinoline effectively; and the Zn species of catalyst further improved aromatization process of dihydroquinoline to quinoline. Moreover, the Zn/Hβ catalyst presented relatively enhanced ability of anti-activation and excellent regenerability, owing to decrease strong acid-induced polymerization of active intermediates to form the coking. Under the optimized operating conditions, more than 51 % yield of quinoline was achieved over Zn/Hβ catalyst; which far exceeded quinoline yield (28 %) over the pure Hβ one. Besides, a plausible reaction routes in vapor-phase acrolein diethyl acetal with aniline to quinolines were suggested in this paper.
Bioinspired Atomic Manganese Site Accelerates Oxo-Dehydrogenation of N-Heterocycles over a Conjugated Tri- s-Triazine Framework
Zhang, Zhou,Liu, Wengang,Zhang, Yuanyuan,Bai, Jingwen,Liu, Jian
, p. 313 - 322 (2021)
Herein, taking inspirations from metalloenzymes, we constructed atomically dispersed manganese sites anchored onto conjugated tri-s-triazine units of graphitic carbon nitride as a bioinspired photocatalyst (Mn1/tri-CN) for the oxo-dehydrogenation of N-heterocycles. The primary coordination sphere of atomic Mn-N2 sites (role i: oxygen activation) as well as the π-πstacking interactions between tri-s-triazine units and substrate mimicking the secondary coordination sphere (role ii: substrate adsorption) synergistically realized high-efficiency electron transfer/utilization in photocatalytic oxidation reactions, as was demonstrated experimentally and theoretically. The Mn1/tri-CN catalyst exhibited impressive oxo-dehydrogenation activity and selectivity toward a broad scope of N-heterocycles in an air atmosphere. The current work suggests that simultaneously engineering the metal active sites of catalysts and the adaptive local environment of the matrix may open an avenue for the synthesis of fine chemicals.
A biomass-derived N-doped porous carbon catalyst for the aerobic dehydrogenation of nitrogen heterocycles
Cui, Fu-Jun,Guo, Fu-Hu,Liu, Jing-Jiang,Liu, Xiao-Yu,Quan, Zheng-Jun,Ullah, Arif,Wang, Xi-Cun,Zhu, Ji-Hua
supporting information, p. 1791 - 1799 (2022/01/31)
N-doped porous carbon (NC) was synthesized from sugar cane bagasse, which is a sustainable and widely available biomass waste. The preferred NC sample had a well-developed porous structure, a graphene-like surface morphology and different N species. More
Solvothermal fabrication of Bi2MoO6 nanocrystals with tunable oxygen vacancies and excellent photocatalytic oxidation performance in quinoline production and antibiotics degradation
Fan, Qizhe,Liu, Xingqiang,Liu, Zhen,Tian, Jian,Yu, Changlin
, p. 472 - 484 (2022/01/22)
Novel Bi2MoO6 nanocrystals with tunable oxygen vacancies have been developed via a facile low-cost approach with the assistance of a glyoxal reductant under solvothermal conditions. With the introduction of oxygen vacancies, the optical absorption of Bi2MoO6 is extended and its bandgap narrowed. Oxygen vacancies not only lead to the appearance of a defect band level in the forbidden band but can also result in a minor up-shift of the valence band maximum, promoting the mobility of photogenerated holes. Moreover, oxygen vacancies can act as electron acceptors, temporarily capturing electrons excited by light and reducing the recombination of electrons and holes. At the same time, oxygen vacancies help to capture oxygen, which reacts with the captured photogenerated electrons to generate more superoxide radicals (?O2?) to participate in the reaction, thereby significantly promoting the redox performance of the photocatalyst. From Bi2MoO6 containing these oxygen vacancies (OVBMO), excellent photocatalytic performance has been obtained for the oxidation of 1,2,3,4-tetrahydroquinoline to produce quinoline and cause antibiotic degradation. The reaction mechanism of the oxidation of 1,2,3,4-tetrahydroquinoline to quinoline over the OVBMO materials is elucidated in terms of heterogeneous Catal. via a radical pathway.
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
