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Quinoline

Quinoline structure

Quinoline 

structure
  • CAS No:

    91-22-5

  • Formula:

    C9H7N

  • Chemical Name:

    Quinoline

  • Synonyms:

    Quinoline;1-Azanaphthalene;1-Benzazine;Benzo[b]pyridine;Leucol;Leukol;Benzopyridine;Quinolin;B 500;Leucoline;NSC 3396;20214-07-7

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

colourless to brown liquid Quinoline is a colorless liquid with a penetrating amine odor. Turns brown on exposure to light. Quinoline has a heavy, penetrating and nauseating, yet sweet odor of good tenacity.


Quinoline appears as 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.|Liquid|COLOURLESS HYGROSCOPIC LIQUID WITH CHARACTERISTIC ODOUR. TURNS BROWN ON EXPOSURE TO LIGHT.


Quinoline appears as 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.|Quinoline is 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. It is a mancude organic heterobicyclic parent, a member of quinolines, an azaarene and an ortho-fused heteroarene.|Quinoline is used mainly as an intermediate in the manufacture of other products. Potential exposure to quinoline may occur from the inhalation of cigarette smoke. Quinoline breaks down quickly in the atmosphere and water. Acute (short-term) inhalation exposure to quinoline vapors irritates the eyes, nose, and throat and may cause headaches, dizziness, and nausea in humans. Information on the chronic (long- term), reproductive, developmental, or carcinogenic effects of quinoline in humans is not available. Liver damage has been observed in rats chronically exposed to quinoline by ingestion. An increased incidence of liver vascular tumors has been observed in rats and mice orally exposed to quinoline. EPA has provisionally classified quinoline as a Group C, possible human carcinogen

Quinoline Basic Attributes

129.16

129.16

107477

202-051-6

E66400VT9R

0071

3396

2656

DTXSID1021798

COLORLESS TO BROWN /SRP: TECHNICAL GRADE/|Highly refractive/darkens with age|Colorless liquid

2933499090

Characteristics

12.9

2.06

Purple to dark grey Liquid

1.0900 g/cm3 @ Temp: 25 °C

-14.78 °C

237.7 °C @ Press: 760 Torr

214 °F

n20/D 1.625(lit.)

H2O: slightly soluble

Store below +30°C.

Vapour pressure, Pa at 20°C: 8

Relative vapour density (air = 1): 4.5

Oral-Rat  LD50: 331 mg/kg

Open flame is flammable; high heat decomposes toxic nitrogen oxide gas

vol% in air: 1.2

Penetrating odor, not as offensive as pyridine

Weak tertiary base

1.16e-11 cm3/molecule*sec

pKa= 4.90

1 MG/L= 189 PPM; 1 PPM= 5.28 MG/CU M|Hygroscopic liquid, absorbs as much as 22% water. ... Forms water sol salts with strong acids: pK 9.5|Hydroxyl radical reaction rate constant = 1.16X10-11 cu cm/molecule-sec @ 24 °C

Hygroscopic. Soluble in water.

Amines, Phosphines, and Pyridines

QUINOLINE is hygroscopic. It absorbs as much as 22% water. It is sensitive to light and moisture. It darkens on storage. This chemical is a weak base. A potentially explosive reaction may occur with hydrogen peroxide. It reacts violently with dinitrogen tetraoxide. It also reacts violently with perchromates. It is incompatible with (linseed oil + thionyl chloride) and maleic anhydride. It is also incompatible with strong oxidizers and strong acids. This chemical can be unpredictably violent. It dissolves sulfur, phosphorus and arsenic trioxide. It may attack some forms of plastics. It is a preparative hazard. (NTP, 1992)

896 °F (USCG, 1999)|896 °F|480 °C

-8710 cal/g

May attack some forms of plastic

Critical temperature: 509 °C

Safety Information

III

6.1

UN 2656 6.1/PG 3

2

21/22-38-41-68-40-37/38-51/53-36/38-45

26-36/37/39-36-23-61-45-53

VA9275000

Xn,N,T

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

Explosive when mixed with air

Stable. Incompatible with strong acids, strong oxidizing agents. May discolour on exposure to light. Hygroscopic - protect from moisture. Reacts violently and unpredictably with some materials, especially strong oxidizing agents.

P201-P273-P280-P301 + P310-P305 + P351 + P338-P308 + P313

H301-H312-H315-H319-H341-H350-H411

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Dissolve in such combustible solvent as alcohols, etc. Spray the solution into the furnace with afterburner and scrubber. Pour into a mixture of sand and soda ash (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in the furnace and stand or position oneself on upwind side.|A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.|Quinoline is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.

VIOLENT REACTION WITH DINITROGEN TETRAOXIDE; PERCHROMATES.|Potentially explosive reaction with hydrogen peroxide. ... Incompatible with linseed oil + thionyl choride; maleic anhydride.|Pyridine and quinoline are attacked violently by the liquid oxide.

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires. Behavior in Fire: Heat exposure may cause pressure build-up in closed containers. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 101 °C explosive vapour/air mixtures may be formed.|Carcinogens, Mutagens, Flammable - 2nd degree

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, P405, and P501|H302 (90.78%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 1996 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|P201, P202, P260, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P309+P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P405, and P501|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

U. S. Bu. Mines approved vapor unit; chemical safety goggles; face shield; rubber gloves; coveralls and/or rubber apron; rubber shoes and boots. (USCG, 1999)|Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologues, and derivatives/|Wear boots, protective gloves, and goggles.

IT IS MODERATELY FLAMMABLE BUT DOES NOT EVOLVE A FLAMMABLE CONCN OF VAPOR AT TEMP OF BELOW 99 °C.|It will burn though it may take some effort to ignite.|Combustible when exposed to heat or flame.

HEAT EXPOSURE MAY CAUSE PRESSURE BUILD UP IN CLOSED CONTAINERS.|Its preparation has caused many industrial explosions. Potentially explosive reaction with hydrogen peroxide. ... Unpredictably violent.|Explosive limits , vol% in air: 1.2-7

EXTINGUISH WITH WATER, DRY CHEMICALS, FOAM, OR CARBON DIOXIDE.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide.

Spread over with the 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton, stuffed with ruffled paper.|Environmental considerations: Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. Apply "universal" gelling agent to immobilize spill.|Environmental considerations: Water spill: If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concentration. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors.

Wash the contaminated areas of skin with powerful soap solution. The contaminated clothing should be removed and dried followed by washing with powerful soap solution disposed of. The contaminated shoes should be incinerated.|Personnel protection: Avoid breathing vapors or dusts. ... Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear self-contained breathing apparatus when fighting fires involving this material.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.|/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for QUINOLINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

... IRRITATING TO THE SKIN ...|Moderately toxic by skin contact. A skin & severe eye irritant. ... It can cause retinitis similar to that caused by naphthalene but without causing opacity of the lens.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from strong oxidants, acids, acid anhydrides and food and feedstuffs. Dry. Keep in the dark. Well closed. Store in an area without drain or sewer access.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is irritating to the eyes and skin.

The substance may have effects on the liver. This substance is possibly carcinogenic to humans.

NO open flames. Above 101 °C use a closed system and ventilation.

AVOID ALL CONTACT!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Quinoline is included on this list.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Quinoline is used mainly as an intermediate in the manufacture of other products. Potential exposure to quinoline may occur from the inhalation of cigarette smoke. Quinoline breaks down quickly in the atmosphere and water. Acute (short-term) inhalation exposure to quinoline vapors irritates the eyes, nose, and throat and may cause headaches, dizziness, and nausea in humans. Information on the chronic (long- term), reproductive, developmental, or carcinogenic effects of quinoline in humans is not available. Liver damage has been observed in rats chronically exposed to quinoline by ingestion. An increased incidence of liver vascular tumors has been observed in rats and mice orally exposed to quinoline. EPA has provisionally classified quinoline as a Group C, possible human carcinogen

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

With 260 mg quinoline per kg creosote-pentachlorophenol, quinoline was detected in wastewater from an on-site storage pond in central Texas(1). The compound was qualitatively identified in CO and UT shale oil wastewaters during 1981-2(2). A quinoline concn of 20 ng/l was estimated to be present in synthetic coal conversion wastewater(3). A baseline study of gaseous emissions from polystyrene combustion indicate that quinoline represents 2.08% of the total gas-phase PAH emissions(4). Quinoline was tentatively identified in the base fraction of wastewater from gasification of Indian Head lignite coal at an estimated concentration of 0.49 mg/l(5). Gasoline and diesel-powered vehicle exhaust emissions have been shown to contain quinoline at concns ranging from 5.3 (noncatalyst) and 0.57 ug/km (catalyst), and 0.46 (diesel) ug/km, respectively(6).

SEDIMENTS: Monitoring results from the Puget Sound, WA are as follows: 39 sediment samples from 6 cores 0-47 cm deep Sept 1978, 74% were positive with respect to quinoline at a range of 160-6600 ng/g organic carbon, 1430 ng/g organic carbon avg. with 11% recovery efficiency(1). Lake Washington sediment core samples taken in September 1978, resulted in 100% pos detections with 260, 1300 and 120 ng/g organic carbon at 0-2 cm, 2-6 cm and 35-37 cm deep, respectively, with 11% recovery efficiency(1). Less than 5% of the total bed-sediment samples from 443 sites in 19 major US river basins collected from 1992-95 tested positive for quinoline(2).

URBAN/SUBURBAN: A study was conducted in which the outdoor air of 8 homes in Columbus, OH, during the winter heating season of 1986/1987, were analyzed for contaminants(1). The results were (min, max, avg in ug/cu m): 0.78, 5.5, 3.3, respectively(1). Ambient data collected in 1988 indicate that the mean concn of quinoline of 3 samples from 2 US urban locations was 0.34 ug/cu m, with concns ranging from not detected to 1.0 ug/cu m(2).|INDOOR: A study was conducted in which the indoor air of 8 homes in Columbus, OH, during the winter heating season of 1986/1987, were analyzed for contaminants(1). The results were as follows (area, min, max, avg in ug/cu m): kitchen - 8.5, 640, 140; living room - 9.1, 1,100, 240(1). Average indoor concns of these 8 sample homes occupied by smokers were 93, 560, 250 ug/cu m in homes having electric, gas, and a combination electric/gas heating and cooking systems, respectively(1); those not occupied by smokers were 26, 10, and 11 ug/cu m, respectively(1).|SOURCE DOMINATED: Outdoor air samples from a Logan Wash, CO Shale oil wastewater treatment facility collected in Nov 1982, contained 1 ug/cu m quinoline(1). A Dupont site in Deepwater, NJ tested during 1977, contained 4 ng/cu m(2). Quinoline was found to be adsorbed onto particulate matter in the air above New York City in 2 samples at 22 and 69 ng/cu m air, respectively(3).

Quinoline has been detected in cigarette smoke in the following concentrations: 19.67 ug/cigarette for 85 mm non-filtered, 0.62 ug/cigarette for 100 mm, 5 mm smoked filtered and 1.2 ug/cigarette for 100 mm, 55 mm smoked non-filtered(1). Indoor concentrations of quinoline and isoquinoline correlate very closely with those of nicotine and can be used to indicate indoor levels of environmental tobacco smoke(2).

Toxicity

highly toxic

LD50 Rat oral 460 mg/kg|LD50 Rat oral 331 mg/kg|LD50 Rabbit skin 540 mg/kg

Quinoline, isoquinoline and other derivatives of quinoline are present in coal and in slightly decomposed sphagnum peats(1).

QUINOLINE MAY BE EXTRACTED FROM BONE OIL ... .|... FOUND IN TOBACCO SMOKE.|The main basic components in coke oven tars are quinoline (16-20% of the total), isoquinoline (4-5%), and methylquinolines. Those dicyclic bases are less prominent in continuous vertical retort (CVR) and low temperature tars ...|Quinoline's production and use as a chemical intermediate, corrosion inhibitor(1), in the manufacture of pharmaceuticals, and as a solvent(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Kocs ranging from 2.84 to 10.9(2,3), indicates that quinoline is expected to have very high mobility in soil(SRC). Volatilization of the neutral species of quinoline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.67X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 0.06 mm Hg(4), and water solubility, 6,110 mg/l(5). The potential for volatilization of quinoline from dry soil surfaces may exist(SRC) based upon its vapor pressure(4). However, the pKa of quinoline is 4.90(6), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(7). Quinoline was degraded in a Danish sandy soil from Lundgaard, Jutland, characterized by 2.47% organic carbon content, 80.2% sand, 13.2% silt, 4.8% clay, and a pH of 5.8; using batch experiments at pH 5.8 and 7 with concns of 10 and 50 mg/kg quinoline, 14CO2 production was 21%/day after 3-4 days in all experiments(8); observed biodegradation to hydroxylated products was reported using freshwater sediment slurries incubated under methanogenic conditions(9). Therefore, biodegradation may be a slow environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 2.84 to 10.9(2,3), indicates that quinoline is not expected to adsorb to suspended solids and sediment(SRC). However, the pKa of quinoline is 4.90(7), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(8). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.7X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.06 mm Hg(5), and water solubility, 6,110 mg/l(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 25 and 186 days, respectively(SRC). Quinoline may be susceptible to photolysis as indicated by strong UV absorption in water at wavelengths >290 nm with maximum at 312.5 nm(9). According to a classification scheme(10), a BCF range of <0.1 to 3.8(11), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation may be a slow environmental fate process in water based upon a measured 0.2% theoretical BOD in 2 weeks using the Japanese MITI test(11) and observed biodegradation to hydroxylated products using freshwater sediment slurries incubated under methanogenic conditions(12).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), quinoline, which has a vapor pressure of 0.006 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase quinoline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 days(SRC), calculated from its rate constant of 1.16X10-11 cu cm/molecule-sec at 25 °C(3). Strong absorption of UV light wavelenghts >290 nm with an absorption maximum at 312.5 nm in water(4), suggests the potential for direct photolysis of quinoline in the atmosphere(SRC). This compound may be removed from the atmosphere by wet and dry deposition as indicated by the identification of quinoline sorbed to atmospheric particulates(5) and in rainwater samples(6).

The rate constant for the vapor-phase reaction of quinoline with photochemically-produced hydroxyl radicals is 1.16X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.4 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constants for the vapor-phase reaction of quinoline with NO2 and ozone are <1.6X10-20 cu cm/molecule sec and <1.0X10-19 cu cm/molecule sec, respectively(1). Evidence was obtained indicating that quinoline reacts with gas-phase nitric acid. The second order rate constant for the reaction of quinoline with nitrite ions in aqueous solution is 7.09X10+9 l/mole second(2).|Quinoline will not hydrolyze in environmental aquatic systems(1). Oxidation half-life was calculated to be >10+4 hours in all surface waters(1). Quinoline will be susceptible to photolysis as indicated by strong UV absorption in water at wavelengths >290 nm with maximum at 312.5 nm(3). During late June, the aquatic near surface half-life with sunlight, pH = 6.9, has been estimated to be 21 days(1), or 25 days(2); at wavelength = 313 nm (artificial irradiation) the photolysis reaction rate, Kp, is about 5.9X10-6 sec-1(1). Photolysis rates in natural sunlight vary with pH, presence of humic acids, depth of water and season(1,2). Calculated half-life = 160 days in winter and the calculated Kp summer/Kp winter ratio is 7.2(2). Measured Kp at pH = 6.9 is greater than Kp at pH = 4.4(3). Under late June sunlight, humic acids photosensitize quinoline, increasing the rate of photolysis by 3.9 times, but decreasing by 0.38 times under artificial lighting (wavelength = 313 nm)(2). Tropospheric half-lives of quinoline in water droplets have been approximated at 9 and 20 minutes at neutral and acidic pHs, respectively(4).

3.80|At an initial concentration of 0.8 and 0.08 mg/l, quinoline had a BCF ranging from <0.1-2.5 and <1.0-3.8, respectively, in orange red killifish(1). Rainbow trout swimup fry, ranging from 0.21-0.41 g in size, were exposed to quinoline at 1 mg/l for 48 hours and analyzed for bioconcentration(2). Whole body levels of quinoline increased rapidly during the first 4 hours of exposure and reached an apparent plateau after about 24 hours. Quinoline had a calculated bioconcentration factor of 3.73. After 48 hours, the fish were placed in non-quinoline contaminated water for 24 hours and monitored for depuration(2). Less than 2% of unmetabolized quinoline remained after the 24-hour depuration period. Metabolites found within fish tissues included hydroxyquinolines and quinolinethiols(2). In a static exposure study using fathead minnows, Pimephales promelas, a bioconcentration factor (BCF) of 8 was measured(3). According to a classification scheme(4), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

1.26e+03 L/kg|The measured log Koc for quinoline is 2.84(1). The adsorption coefficients of quinoline to Ca-montmorillonite and creek sediments are 7.3 and 10.9, respectively(2). A Koc of 43 was reported using low-organic-carbon subsurface materials(11). According to a classification scheme(3), these Koc values suggest that quinoline is expected to have very high mobility in soil. Quinoline was found to be relatively mobile using a Danish sandy soil(10). Intensity of quinoline added to a natural sand aquifer on the Canadian Air Force Base Borden, Ontario, Canada via a field study using coal tar creosote were found to increase after 278 days, about 25 m from the croesote source, added at an initial concn of 10.1 g/kg creosote(4). Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(7,8), suggesting that mobility may be much lower in some soils(SRC). The pKa of quinoline is 4.90(5), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(6); therefore, adsorption increases with increasing soil acidity(11). Sorption onto airborne particulates has been observed(9). A Kd value of 0.83 was measured using a Danish sandy soil from Lundgaard, Jutland, characterized by 2.47% organic carbon content, 80.2% sand, 13.2% silt, 4.8% clay, and a pH of 5.8(10).

The Henry's Law constant for quinoline is estimated as 1.7X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 0.06 mm Hg(1), and water solubility, 6,110 mg/l(2). This Henry's Law constant indicates that quinoline is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 25 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 186 days(SRC). Quinoline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Samples taken near two different underground coal gasification sites in Hoe Creek, Wyoming had levels of quinoline plus isoquinoline concentrations of 0.45 ppb, 7.1 ppb, 14 ppb(1). Intensity of quinoline added to a natural sand aquifer on the Canadian Air Force Base Borden, Ontario, Canada via a field study using coal tar creosote were found to increase after 278 days from an initial concn of 10.1 g/kg creosote(4). Quinoline was detected in groundwater samples collected from Pensacola, FL (June, 1986) and St. Louis Park, MN (October, 1986) at concentrations of 11,200 ug/l and <15 ug/l, respectively(2). Both of these sites have been contaminated as a result of creosote wood treatment activities(2).|SURFACE WATER: Quinoline was qualitatively identified in River Waal at Brakel, Germany during 1974(1).|RAIN/SNOW/FOG: 3 samples Los Angeles rainwater collected 12/81-2/82, contained concentrations of quinoline plus isoquinoline and their substituted compounds 0.7-2 ug/l, 1.6 ug/l avg, respectively(1).

PRIMARY ROUTES OF EXPOSURE ARE SKIN CONTACT WITH THE LIQUID OR INHALATION OF THE VAPOR OR AEROSOL.|NIOSH (NOES Survey 1981- 1983) has statistically estimated that 4,241 workers (810 of these are female) are potentially exposed to quinoline in the US(1). Occupational exposure to quinoline may occur through inhalation and dermal contact with this compound at workplaces where quinoline is produced or used(SRC). Quinoline is a possible marker compound for exposure to cigarette smoke(2). The general population is likely to be exposed via inhalation of cigarette smoke(2) and quinoline sorbed onto particulate matter in urban air(3).|The most probable route of worker exposure to quinoline would be inhalation of particulates or vapors due to petroleum processing, shale oil processing and production or use of coal derived products(1). Other possible routes are ingestion of coarse airborne particulates or particulates in the upper respiratory system and contamination of the skin during maintenance work(1). The impregnation and handling of creosote impregnated wood resulted in worker exposure to quinoline via inhalation at concns of <0.1 mg/cu m(2). Samples from Logan Wash, Co. shale oil wastewater treatment facility collected in Nov 1982, showed a concentration of 6 ug/cu m in indoor air(3).

Drug Information

Salmo gairdneri (rainbow trout) readily absorb & metabolize (14)C quinoline when exposed to 1 mg/l concn in water. Juvenile fish accumulated over 60% of the total radiolabel body burden in the gall bladder as quinoline metabolites after 48 hr exposure, followed by 24 hr in clean water. Hydrolysis products of the metabolites, isolated by alkaline digestion & base-catalysed acetylation, were found to be hydroxyquinolines & quinolinethiols. There is evidence that the hydroxy form was present in the gall bladders as the glucuronide was obtained from thin layer chromatographic experiments, & by cleavage with beta-glucuronidase. The thiols, identified by high & low resolution mass spectrometry, predominated over the hydroxy derivative in most tissues examined. Relative body burdens of quinoline plus metabolites after 48 hr were in the order of: gall bladder >muscle >gut >eyes >liver.|Quinoline is absorbed percutaneously.|Rainbow trout were fed pelleted food containing (14)C-quinoline to assess the relationship of digestive processes to pharmacokinetics. The pH of material in the stomach of rainbow trout ranged from 2.7 to 5.2. ... At 2 hr after feeding, 67% of the quinoline was estimated to be non-ionized & available for absorption across gastric epithelium. Quinoline was >99% non-ionized in the alkaline environment of the intestine; however, relative concns in the intestine were about 8% of those measured in the stomach. Gastric absorption was consistent with known serum profiles & excretion patterns of dietary quinoline. Rates of gallbladder emptying appeared to exceed rates of hepatic bile secretion until about 8 hr after a single feeding. Time since feeding influenced both the amount & concn of quinoline-derived radioactivity in the bile. ...|The primary routes of exposure to quinoline are through skin contact with the liquid & inhalation of the vapor or aerosol.|Elimination half-lives of quinoline & its metabolites showed considerable variability among tissues, with a range of 0.3 days for gallbladder to 8.7 days for muscle. Biliary/fecal excretion was significant & glucuronide conjugates made up 14% of the radioactivity in the bile /in trout/.

WITH AROMATIC HETEROCYCLIC NITROGEN CMPD ... HYDROXYLATION OCCURS AT THE 3-POSITION, & IF A BENZENOID RING IS ATTACHED TO HETEROCYCLE, HYDROXYLATION OCCURS ALSO AT POSITIONS ORTHO & PARA TO THE N ATOM, IE QUINOLINE YIELDS 3-, 6- & 8-HYDROXYQUINOLINE. QUINOLINE IS ... METABOLIZED INTO 6-HYDROXYCARBOSTYRIL; INITIAL OXIDATION TO 2-HYDROXYQUINOLINE (CARBOSTYRIL) IS CATALYZED BY A SOL ENZYME OF RABBIT LIVER, & SUBSEQUENT HYDROXYLATION ... IS CATALYZED BY A MICROSOMAL ENZYME.|QUINOLINE YIELDS CIS-7,8-DIHYDRO-7,8-DIHYDROXYQUINOLINE PROBABLY IN PSEUDOMONAS. QUINOLINE YIELDS 5,6-DIHYDROXYQUINOLINE & 3-HYDROXYQUINOLINE IN RABBIT. QUINOLINE YIELDS 2-HYDROXYQUINOLINE IN RABBITS. /FROM TABLE/|FIVE FRACTIONS WERE SEPARATED AFTER METABOLISM OF (3)H-LABELED QUINOLINE BY RAT LIVER MICROSOMES. IDENTIFIED METABOLITES WERE 5,6-TRANS-DIHYDROXY-5,6-DIHYDROQUINOLINE, QUINOLINE 1-OXIDE, & 3-HYDROXYQUINOLINE. RELATIVE AMT OF METABOLITES WERE DEPENDENT ON ENZYME INDUCER PRETREATMENT. METABOLIC PATHWAY IS PROPOSED ON BASIS OF ENZYME INDUCER STUDIES.|... The metabolites of quinoline and isoquinoline, as formed in vitro with rat liver homogenate, were identified to investigate possible molecular bases for the differences in their biological activity. The ethyl acetate extractable metabolites of quinoline and isoquinoline were analyzed directly by high pressure liquid chromatography after silylation, and by capillary gas chromatography. The major metabolite of quinoline was 5,6-dihydroxy-5,6-dihydroquinoline. Lesser amounts of 2- and 3-hydroxyquinoline and quinoline-N-oxide were also identified as metabolites. 1-, 4- and 5-hydroxyisoquinoline and isoquinoline-N-oxide were detected as metabolites of isoquinoline. 5,6-Dihydroxy-5,6-dihydroisoquinoline was detected as only a minor metabolite. This difference in the extent to which these isomers are ultimately metabolized to dihydrodiols may be associated with their differences in biological activity.|For more Metabolism/Metabolites (Complete) data for QUINOLINE (8 total), please visit the HSDB record page.|Quinoline has known human metabolites that include 3OHQ, Q-8,6-epoxide, and Quinoline 1-oxide.

0.05 Days

QUINOLINE BINDS TO RNA, DNA & CERTAIN POLYRIBONUCLEOTIDES IN PRESENCE OF NADPH & RAT LIVER MICROSOMES. BINDING WAS PRONOUNCED WITH HELP OF SOME INDUCERS OF MICROSOMAL MONOOXYGENASE SYSTEM. BINDING REACTION REQUIRED NADPH & WAS INHIBITED BY CARBON MONOXIDE, ANILINE, 7,8-BENZOFLAVONE, METHYRAPONE OR SKF 525A. QUINOLINE BOUND PREFERENTIALLY TO POLY(A), POLY(C), POLY(G) & POLY(X), BUT NEGLIGIBLY TO POLY(U) & POLY(I). MOST OF QUINOLINE RESIDUES OF THE ADDUCTS, REGARDLESS OF KIND OF POLYNUCLEOTIDES USED WERE RELEASED BY ACID OR ALKALI AT 100 °C IN FORM OF 3-HYDROXYQUINOLINE. THE 2,3- OR 3,4-EPOXY DERIVATIVE OF QUINOLINE APPARENTLY IS THE REACTIVE INTERMEDIATE FOR NUCLEIC ACID MODIFICATION.

Monomethylquinolines, 2,8-dimethylquinoline, and some homologues of isoquinoline.

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. (USCG, 1999)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

CLINICAL SIGNS OF TOXICITY INCLUDE LETHARGY, RESPIRATORY DISTRESS, & PROSTRATION LEADING TO COMA. ... IRRITATING TO SKIN & MAY CAUSE PRONOUNCED PERMANENT CORNEAL INJURY.|... Quinoline paralyzes the respiratory muscles.|... (Presumably in humans), "absorption of quinoline into the body may lead to nausea, vomiting, gastro-intestinal cramps, fever, & a feeling of dizziness, an irregular rapid pulse & collapse."|Quinoline & many of its derivatives have been reported to be toxic to the retina or optic nerve in man ... .|Quinoline has been shown to inhibit competitively the activity of type A monoamine oxidase isolated from human placental & human brain synaptosomal mitochondria. Type B MAO was noncompetitively inhibited.

quinoline

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Cough. Sore throat.


Redness.


Redness. Pain.

Quinoline Use and Manufacturing

Methods of Manufacturing

Prepd by the Skaup synthesis of heating aniline with glycerol and nitrobenzene in presence of sulfuric acid: Clarke, Davis, Org. Syn. coll. vol. I, 478 (2nd ed., 1941) 478: alternate syntheses: Manske, Chem Rev. 20, 113 (1942); Bergstrom, ibis, 35, 150 (1944). Process based on interaction of aniline with acetaldehyde and a formaldehyde hemiacetal: Cislak, Wheeler, US 3020281 (1962 to Reilly Tar & Chem.).|QUINOLINE MAY BE EXTRACTED FROM BONE OIL ... .|Isolation from the chemical oil fraction of coal tar distillates.|Skraup synthesis by heating aniline with glycerol and nitrobenzene in presence of sulfuric acid.

Uses

Solvent. Determine the refractive index of the mineral. Separation of vanadate and arsenate. Test lignin. Determination of arsenic acid by micro-crystallization method. Precipitating agent for zirconium, thorium, cerium, lanthanum, neodymium and praseodymium. Test bismuth, antimony, nickel, rhenium, titanium, platinum, palladium, iridium, osmium and gold. Organic Synthesis. Dye manufacturing. Medical antimalarial drugs. Specimen preservation.

Production

(1978) AT LEAST 4.54X10+7 G|(1982) PROBABLY GREATER THAN 2.27X10+6 G

GRADES: REAGENT; TECHNICAL|Commercial quinoline is at least 90% pure. Chromatographic composition of this product is typically 92% quinoline and 5% isoquinoline by weight.

Quinoline: ACTIVE|World production of quinoline is more than 2000 tons annually.|A basic heterocyclic nitrogenous compound typically occurring in coal tar and obtained from it, but more frequently by synthesis.

GAS CHROMATOGRAPHY/MASS SPECTROMETRY DETECTED QUINOLINE & OTHER POLYNUCLEAR AROMATIC HYDROCARBONS IN EMISSIONS FROM COKE QUENCH TOWER IN QUANTITY SUFFICIENT TO POSE POTENTIAL HEALTH HAZARD.|TRACE ORGANIC COMPOUNDS (SUCH AS QUINOLINE) IN VARIOUS ENVIRONMENTAL SAMPLES OF TAP WATER, RIVER WATER, SEWAGE, RAIN WATER, SEAWATER & SEDIMENT TAKEN FROM THE KITAKYIUSHU AREA (JAPAN) WERE ANALYZED BY COMPUTERIZED GAS CHROMATOGRAPHY-MASS SPECTROMETRY.|ASTM Method D4763. Standard Practice for Identification of Organic Chemicals in Water by Fluorescence Spectroscopy.

Hazardous Air Pollutants (HAPs)|Fire Hazards -> Carcinogens, Mutagens, Flammable - 2nd degree

Computed Properties

Molecular Weight:129.16
XLogP3:2
Hydrogen Bond Acceptor Count:1
Exact Mass:129.057849228
Monoisotopic Mass:129.057849228
Topological Polar Surface Area:12.9
Heavy Atom Count:10
Complexity:111
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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