Quinoline

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

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.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

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.

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.

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.

LC50 Xenophus laevis (South African clawed toad) embryo 26.3 mg/l/96 hr /Conditions of bioassay not specified/

LC100 Tetrahymena pyriformis (ciliate) 6.19 mmole/l/24 hr /Conditions of bioassay not specified/

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

Oral (L10) ; inhalation (L10)

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

Cough. Sore throat.

Redness.

Redness. Pain.

Sore throat.

Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)

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).

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.

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).

Quinoline is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

Quinoline is used mainly as an intermediate in the manufacture of other products.

Used to make paints, dyes, and other chemicals; Also used as a preservative for anatomical specimens, solvent for resins and terpenes, fungistat, corrosion inhibitor, antimalarial drug, flavoring agent, and decarboxylation reagent; [HSDB] Extracted from coal-tar distillates; occurs in polluted air and cigarette smoke; [AIHA]

Using Disinfectants or Biocides [Category: Clean]

Manuf dyes; prepn hydroxyquinoline sulfate, q.v., niacin. As preservative for anatomical specimens. Solvent for resins abd terpenes.

Chem int for 8-hydroxyquinoline, a fungistat; chem int for pharmaceuticals-e.g., antiinfectives; corrosion inhibitor

Used as ... a decarboxylation reagent.

(1978) 3.13X10+7 G (PRINCPL CUSTMS DISTS)

(1982) 3.96X10+7 G (PRINCPL CUSTMS DISTS)

2023: 100,000 - <250,000 lb

(1978) AT LEAST 4.54X10+7 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Quinoline

1-Benzazine; 2,3-Benzopyridine; Benzo(b)pyridine; Chinoleine; Leucoline; Quinoleine

IFRA_STD_178.pdf

45

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient

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.

GRADES: REAGENT; TECHNICAL

Commercial quinoline is at least 90% pure. Chromatographic composition of this product is typically 92% quinoline and 5% isoquinoline by weight.

All Other Chemical Product and Preparation Manufacturing

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.