Indene
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Indene
structure -
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CAS No:
95-13-6
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Formula:
C9H8
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Chemical Name:
Indene
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Synonyms:
1H-Indene;Indene;Indonaphthene;Inden;NSC 9270
- Categories:
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CAS No:
Description
Yellow green clear liquid
Indene appears as a colorless liquid derived from coal tar. Fp: -2°C; bp:182°C. Density 0.997 g cm-3. Insoluble in water but soluble in organic solvents.|Colorless liquid derived from coal tar.|Colorless liquid. [Note: A solid below 29°F.]
Indene appears as a colorless liquid derived from coal tar. Fp: -2°C; bp:182°C. Density 0.997 g cm-3. Insoluble in water but soluble in organic solvents.|1H-indene is an ortho-fused bicyclic arene comprising of benzene and cyclopentene rings. It is an ortho-fused bicyclic arene and an indene.
Indene Basic Attributes
116.16
116.16
635873
202-393-6
67H8Y6LB8A
62567|9270
1993
DTXSID8042052
LIQUID|Colorless liquid|Colorless liquid [Note: A solid below 29 degrees F].
29029000
Characteristics
0
2.9
White to pale yellow Crystalline Powder
0.9968 g/cm3 @ Temp: 20 °C
-1.8 °C
181.6 °C @ Press: 760 Torr
138 °F
1.596
H2O: INsoluble ;organic solvents: miscible
2-8°C
1.7 hPa (20 °C)
Inhalation-Rat LC50: 14000 mg/m3
Combustible in case of open flame, high temperature and strong oxidant; burning emits irritating smoke
5.10e-11 cm3/molecule*sec
Peroxide formation with air with initiation of polymerization No rapid reaction with water
Hydrocarbons, Aromatic
Polymerizable
INDENE is combustible (flash point between 140°F and 200°F). Polymerizes and oxidizes on standing in the air. This reaction is accelerated by heating, acids, and catalysts, including peroxides. Has exploded during nitration with a mixture of H2SO4 and HNO3.
4.13X10+7 J/Kg at 25 °C
8.81 eV
Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.
Safety Information
Ⅲ
3
UN 3295 3/PG 3
1
10-65-36/37/38-20
23-24/25-62-37/39-26
NK8225000
Xn
Completely packed, lightly placed; storeroom ventilated, away from open flames, high temperature, and stored separately from oxidants
Stable, but air and light sensitive; may polymerize upon exposure to light. Typically contains aroung 80 - 100 ppm of p-tert-butylcatechol as inhibitor. Refrigerate. Flammable. Incompatible with strong oxidizing agents.
P301 + P310-P331
H226-H304
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.
Polymerizes & oxidizes on standing. It has exploded during nitration with (H2SO4 + HNO3).
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)|Flammable - 2nd degree
|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P301+P310, P303+P361+P353, P331, P370+P378, P403+P235, P405, and P501|Aggregated GHS information provided by 284 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P303+P361+P353, P304+P340, P307+P311, P312, P321, P370+P378, P403+P233, P403+P235, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P309+P311, P312, P314, P321, P332+P313, P333+P313, P337+P313, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective. SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). 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 128 [Flammable Liquids (Water-Immiscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|(See protection codes)
DEFLAGRATES ON HEATING. /INDENE PICRATE/
The worker should wash daily at the end of each work shift.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 ppm (45 mg/cu m).
Indene was qualitatively identified in effluents from a POTW facility in Sauget, Illinois(1). On October 24, 1974, indene was qualitatively found in advanced waste treatment concentrates from Lake Tahoe, CA(2). During August and September of 1979, indene was found at a concn range of 0.08-0.4 ug/cu-m in the Allegheny Mountain Tunnel in Pennsylvania(3). Indene was identified at a concn range of 10.3-137.6 ng/L in paper-mill effluents being discharged into the Rainy River(4). Indene was identified in a plume of contaminated water moving through sand away from creosote waste disposal lagoons(5). Indene was found at a concn of 1.28 in an air sample taken near an oil fire(6).|Indene was found in a groundwater sample prior to coal gasification (0.03 ppm), process water during gasification (272 and 72 ppm), and aqueous condensate from low-BTU coal gasification (363 ppm)(1). Indene was found at a concn of 15 ng/L in a canal to a harbor of a freshwater lake before any boat traffic was observed; after 1,293 boats passed through the canal, the concn of indene was 74 ng/L(2). Indene has been detected in wastewater effluents from the timber products industry at a concn of 8,252 ng/ul extract(3).
Indene was found at an average concn of 10 ppb in water and sediment samples from the lower Tennessee River below Calvert City, KY(1).
In 1977, indene was qualitatively identified in the air of six industrial cities of the former USSR(1). Indene was qualitatively found in the air of three South African cities during the summer of 1975-winter of 1976(2). Indene was qualitatively identified in air taken at Homebush Bay, Australia on June 3, 1975(3). Indene was qualitatively identified in Paris air on October 24, 1972(4).
Toxicity
moderately
Indene is found in high-temperature coal tar at an average concn of 1 percent(1). It can be released to the environment in emissions from biomass combustion(2).
Indene is released to the environment in emissions from auto exhaust, polymer combustion, polymer manufacture, tobacco smoke(4), ethylene combustion(5), and waste incineration(8). Indene emission rates are about 0.1 and 0.15 mg/km from gasoline-powered vehicles and diesel trucks, respectively(1). Indene is released in wastewater from paper-mills(2), creosote waste disposal sites(3), and coal-tar distillation and wood treatment facilities(6). Indene may be released to surface water from motor-boat emissions(7). The annual loadings of indene in runoff from land in the Canadian Ontario and Great Lakes water basins are estimated to be 1,053 and 2,271(kg/yr, respectively(9).
TERRESTRIAL FATE: The estimated Koc value of 540(1-2,SRC) suggests that indene will have low mobility in soil(3). If spilled on soil surfaces, some indene may photolyze(4,SRC) or volatilize into the air (estimated Henry's Law constant of 1.59X10-3 atm-cu m/mol at 25 °C(5)). However, adsorption may limit these processes(SRC). Limited data suggest indene is biodegradable in soil(6-7).|AQUATIC FATE: Based on the estimated Koc value of 540(1-2,SRC), indene may adsorb to sediment; indene was found in a river sediment(3). Oxidation via reaction with sunlight produced alkyl peroxy radicals is very slow (estimated half-life of 1,100 days(4)). Limited data suggest indene is biodegradable. Indene may be susceptible to some direct photolysis in sunlight(5); however, this is not expected to be an important removal process(SRC). Indene is not expected to hydrolyze in the aquatic environments(SRC). Volatilization from water is fast with estimated half-lives of 3.7 hrs and 4.4 days from a model river and model lake, respectively(1,SRC).|ATMOSPHERIC FATE: Based upon a measured vapor pressure of 1.1 mm Hg at 25 °C(1), indene is expected to exist almost entirely in the vapor phase in the ambient atmosphere(2,SRC). Vapor-phase indene will degrade rapidly in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 6.2 hours(3,SRC).
The rate constant for the vapor phase reaction of indene with photochemically produced hydroxyl radicals can be estimated to be 6.2X10-11 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 6.2 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). In methanol solution, indene very weakly absorbs some UV radiation above 300 nm; no absorbance above 310 nm(2). Therefore, indene may photolyze, but it is not expected to be an important removal process(SRC). The rate constant for the reaction of indene with sunlight-produced alkyl peroxy radicals in water at 30 °C was measured to be 7 L/mol-sec(3) which corresponds to an oxidation half-life of about 1,100 days at an alkyl peroxy concn of 1X10-9 M in water(4,SRC); therefore, oxidation will not be important in water(SRC).
Based on a measured log Kow of 2.92(2) and a regression derived equation(1), the BCF for indene can be estimated to be about 57(SRC). Therefore, bioconcentration of indene in aquatic organisms is not expected to be important(SRC).
Based on a measured log Kow of 2.92(2) and a regression derived equation(1), the Koc for indene can be estimated to be about 540(SRC). According to a suggested classification scheme(3), this Koc value suggests low mobility in soil.
The Henry's Law constant for indene can be estimated to be 1.59X10-3 atm-cu m/mole at 25 °C using a structure estimation method(1,SRC). According to a suggested classification scheme(2), this value of Henry's Law constant suggests that volatilization from water is rapid(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 3.7 hours(2,SRC). The volatilization half-life from a model lake (1 m deep) can be estimated to be about 4.4 days(2,SRC).
SURFACE WATER: Indene was found at an average concn of 10 ppb in water and sediment samples from the lower Tennessee River below Calvert City, KY(1). Indene was qualitatively identified in water from the Black Warrior River in Tuscaloosa, AL(2). Indene was quantified at a concn range of 2.9-59.4 ng/L in water from the Rainy River which forms an international boundary between the U.S. and Canada(3). Indene was qualitatively identified in water at various locations of the Detroit River(4).|GROUNDWATER: Indene was found at a concn range of 0.01-1.31 mg/L in groundwater in the vicinity of a wood treatment facility in Pensacola, FL(1). Indene was found at a concn range of 36-190 ppb in three groundwater samples near an underground coal gasification site in Northeastern Wyoming(2). Indene was qualitatively identified in a contaminated aquifer near a coal-tar distillation and wood preserving facility in St. Louis Park, MN(3). In 1986, indene was found at a concn range of 0.01-13 mg/L in groundwater at Gas Works Park, Seattle, WA, the site of a coal and oil gasification operation that ceased operation in 1956(4).|DRINKING WATER: Indene was found at a concn of 18 ppb in potable water from a contaminated well in Ames, IA(1).|RAIN/SNOW: Indene was found at a concn of >0.05 ug/L in a snow pack from a rural area located east of Sault Ste Marie, Canada(1).
Indene was qualitatively identified as a volatile component of roasted filberts(1).
In occupational settings, workers may be exposed to indene via inhalation of vapor and dermal contact(1). The general population may be exposed to indene via inhalation of contaminated air, especially in industrialized areas(4-7). The general population may also be exposed to indene via consumption of contaminated drinking water and food(2-3).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 753 workers are potentially exposed to indene in the USA(1). The mean indene exposure to workers in a factory that impregnates wood with creosote was 0.4 ug/cu m(2).
Indene was detected in respiratory gas from 7 of 8 male volunteers (3 smokers) at a concn range of 0.14-83 ug/hr-expired air; according to this study, indene may result from or be related to normal human metabolism(1). Indene was found at an average concn of 0.138 ng/L in 59 of 387 expired air samples obtained from 54 nonsmoking-volunteers(2).
Drug Information
YIELDS CIS-1,2-DIHYDROXYINDANE & TRANS-1,2-DIHYDROXYINDANE IN RABBITS. /FROM TABLE/|RAT-LIVER MICROSOMES SUPPLEMENTED WITH NADPH CONVERTED INDENE INTO TRANS-INDANE-1,2-DIOL ...|THE OXIDATION OF INDENE TO TRANS-1,2-DIHYDROXYINDANE IN LIVER PREPN IN VITRO WAS DEMONSTRATED. THE REACTION WAS MEDIATED BY LIVER MICROSOMES OF RATS & RABBITS IN THE PRESENCE OF NADPH-GENERATING SYSTEMS.
3.00 Days
Exposure Routes: inhalation, ingestion, skin and/or eye contact Target Organs: Eyes, skin, respiratory system, liver, kidneys, spleen (NIOSH, 2016)
Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, wash the contaminated skin with soap and water. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)
BY ANALOGY BETWEEN CHEMICAL STRUCTURE & TOXICOLOGICAL EFFECTS OF RELATED MONOAROMATIC HYDROCARBONS, INHALATION OF INDENE VAPORS CAN BE EXPECTED TO CAUSE IRRITATION OF MUCOUS MEMBRANES.|THERE ARE ... SENSITIZING ACTIONS OF COUMARONE & INDENE, USED IN COPOLYMERIZATION WHEN MAKING COUMARONE-INDENE RESINS. USE OF THESE RESINS CONTAMINATED WITH TRACES OF MONOMERS CAN CAUSE ALLERGIC DERMATITIS.
indene
inhalation, ingestion, skin and/or eye contact
In Animals: irritation eyes, skin, mucous membrane; dermatitis, skin sensitization; chemical pneumonitis (aspiration liquid); liver, kidney, spleen injury
Eyes, skin, respiratory system, liver, kidneys, spleen
Indene Use and Manufacturing
In high-temperature tar, the content of indene is 0.25%-0.3%, mainly in coal tar and crude benzene fractions with a boiling point of 168-175℃. In heavy benzene before 200℃, coumarone and indene account for more than 40% . The heavy benzene is used as the raw material for rectification on a fractionation tower with 44 theoretical trays, the reflux ratio is controlled to be 15-20:1, and the fraction with a top temperature of 180.6-181.1°C is cut, and the indene content can reach 98%. Another method of extracting indene is to use heavy benzene and crude solvent oil as raw materials, and use furfural as an azeotropic agent for azeotropic distillation. Since furfural or formaldehyde can form an azeotrope with the hydrocarbon components in heavy benzene, but does not form an azeotrope with indene, pure products can be prepared.
Mainly used to produce indene-gumarone resin. The raw material of indene-gumarone resin is the 160-215°C distillate cut from the heavy benzene and light oil fractions, which roughly contains 6% styrene, 4% coumarone, 40% indene, and 4-methylstyrene 5 % And a small amount of xylene, toluene and other compounds, the total amount of resin accounts for 60-70% of the raw materials. Under the action of catalysts such as aluminum chloride, boron fluoride or concentrated sulfuric acid, the indene and coumarone fractions are polymerized under or without pressure to form indene-gumarone resin. Can be mixed with other liquid hydrocarbons as coating solvents. It can also be used as an intermediate for pesticides or mixed with other liquid hydrocarbons as a coating solvent.
1H-Indene: ACTIVE
CONCENTRATION OF INDENE IN THE AIR CAN BE SEPARATED BY TLC.|A modified variant of the purge-and-trap gas chromatographic analysis of volatile organic carbon compounds in water was designed. Samples collected in 1-l glass bottles are purged at 60 C for 1 hr in an ultrapure helium gas stream using an open loop arrangement. Volatile eluates are trapped onto selective adsorbents packed inside stainless steel tubes connected in series. After stripping at a flow rate of 100 mg/min for 60 min, the adsorbent tubes are disconnected, fitted with analytical desorption caps and sequentially desorbed for 10 min on a thermal desorber. The desorbed organics are trapped at 30 C on a packed cold trap prior to flash volatilization of the volatiles across a fused silica transfer line onto a capillary column. The method separated over 200 organic compounds within 40 min using flame ionization and ion trap detection and is capable of quantitation down to 5 ng/l per component. The recoveries of indene from water at 30 and 60 C were 71 and 100%, respectively. A specimen purge seawater standard chromatogram (Tenax-TA tube) revealed the presence of indene. Indene was also seen in chromatograms of water samples taken from Solent estuary in southern England.|ASTM D4763 Standard Practice for Identification of Chemicals in Water by Fluorescence Spectroscopy. FLuorescence, Detection Limit 0.12 ppm
Fire Hazards -> Flammable - 2nd degree
Computed Properties
Molecular Weight:116.16
XLogP3:2.9
Exact Mass:116.062600255
Monoisotopic Mass:116.062600255
Heavy Atom Count:9
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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