Cumene

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Use powder, AFFF, foam, 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).

Rinse mouth. Do NOT induce vomiting. Refer immediately 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.

· 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.

Excerpt from NIOSH Pocket Guide for Cumene:

General First Aid:

General First Aid:

(General first aid procedures)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

10.0 [ppm]

To fight fire, use foam, carbon dioxide, dry chemical.

Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool.

... Precautions ... such as mounds around storage tanks, sills at doorways or especially designed floors /are needed/ to limit spread of escaping liquid. Open flames & other sources of ignition should be excluded where cumene is stored.

Outside or detached storage is preferred. Inside storage should be in a standard flammable liquids storage warehouse, room, or cabinet. Separate from oxidizing materials, nitric acid, sulfuric acid.

Storage temperature: Ambient.

Personal protection: filter respirator for organic gases and vapors adapted to the airborne concentration of the substance. 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. Do NOT let this chemical enter the environment.

Remove all ignition sources; ventilate /the/ area of spill or leak. For small quantities absorb on paper towels /and/ evaporate in a safe place (such as a fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U055, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Cumene is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.

A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. 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.

... Large quantities can be collected and atomized in a suitable combustion chamber. Combustion may be improved by mixing with a flammable liquid. Cumene liquid should not be allowed to enter a confined space, such as a sewer, because of the possibility of an explosion.

For more Disposal Methods (Complete) data for Isopropylbenzene (6 total), please visit the HSDB record page.

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. 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. Do NOT let this chemical enter the environment.

Isopropylbenzene has been detected at 0.13 ug/hour(1) and detected but not quantified(2) in human expired air from non-smoking individuals.

Isopropylbenzene concentration in air samples from non-smoking married females residing in New Jersey and Pennsylvania, in both smoking and nonsmoking homes and nonsmoking workplaces(1).[Table#628]

Endocrine

Eyes, skin, respiratory system, central nervous system

LC50; Species: Daphnia magna (Water flea); Concentration: 0.6 ppm for 48 hr /Conditions of bioassay not specified/

LD50; Species: Agelaius phoeniceus (red-winged blackbird) oral 98 mg/kg

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 25.4 °C, dissolved oxygen 6.6 mg/L, hardness 44.3 mg/L calcium carbonate, alkalinity 42.1 mg/L calcium carbonate, and pH 7.58; Concentration: 6.32 mg/L for 96 hr (confidence limit 6.04-6.61 mg/L)

EC50; Species: Pimephales promelas (fathead minnow); Condtions: flow-through bioassay with measured concentrations, 25.4 °C, dissolved oxygen 6.6 mg/L, hardness 44.3 mg/L calcium carbonate, alkalinity 42.1 mg/L calcium carbonate, and pH 7.58; Concentration: 6.32 mg/L for 96 hr (confidence limit 6.04-6.61 mg/L); Effect: loss of equilibrium. Affected fish lost schooling behavior and swam in a corkscrew/spiral pattern. They were hyperactive and darkly colored, had increased respiration, and lost equilibrium prior to death.

For more Ecotoxicity Values (Complete) data for Isopropylbenzene (14 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 700(SRC), determined from a structure estimation method(2), indicates that isopropylbenzene is expected to have low mobility in soil(SRC). Volatilization of isopropylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.15X10-2 atm-cu m/mole(3). Isopropylbenzene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.5 mm Hg at 25 °C(4). A biodegradation half-life of 2 days (rate constant = 0.322/day) was calculated for isopropylbenzene added to soil microcosms from a weathered petroleum spill site(5), indicating that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 700(SRC), determined from a structure estimation method(2), indicates that isopropylbenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.15X10-2 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hrs and 4 days, respectively(SRC). According to a classification scheme(5), a BCF of 35.5(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Isopropylbenzene, incubated in a sediment/freshwater ecocore, exhibited a mineralization rate of 0.02/day, corresponding to a half-life of 34.6 days(7), indicating that biodegradation may be an important environmental fate process in water(SRC).

AQUATIC FATE: In an experiment to study the disappearance of organic compounds found in crude oil during an oil spill, isopropylbenzene was found to disappear (combination of evaporation and dissolution) within 90 minutes of being spilled into seawater(1). In a similar experiment, water samples taken from an oil spill in the Canadian Arctic waters in the Ragged Channel revealed that after 6 hours, isopropylbenzene could not be detected in the aromatic fraction(2). Isopropylbenzene has a reported volatilization half-life in water ranging from 3.2 to 5.8 hrs(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropylbenzene, which has a vapor pressure of 4.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropylbenzene 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 1.5 days(SRC), calculated from its rate constant of 6.5X10-12 cu cm/molecule-sec at 25 °C(3). Isopropylbenzene exhibits a UV absorption of 258 nm in cyclohexane(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Trace quantities of isopropylbenzene have been detected in the total volatiles of Sapodilla fruit (Achras sapota)(1) and Australian honey(2). Isopropylbenzene was detected not quantified in fried chicken(3), Concord grapes (Vitis labrusca) and Zinfandel wine(4), cooked rice(5), oat groats (Avena sativa)(6), Idaho Russet Burbank baked potatoes(7), Beaufort cheese from the French Alps(8), and fried bacon(9). Isopropylbenzene has been identified as one of several volatile hydrocarbons found in chicken and pork(10).

Seventy foods were analyzed for volatiles from 1996-2000 as part of the US FDA Total Diet Program(1).

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

inhalation, skin absorption, ingestion, skin and/or eye contact

Oral (L400) ; inhalation (L400) ; dermal (L400)

IDENTIFICATION: Cumene is a water insoluble petrochemical used in the manufacture of several chemicals, including phenol and acetone. HUMAN EXPOSURE: In humans, cumene is metabolized primarily to the secondary alcohol. 2-phenyl-2-propranol. This alcohol and its conjugates are readily excreted by humans. No data are available with which to quantify human exposure. It is not possible to assess its potential for carcinogenicity in humans, because long term carcinogenicity studies with the chemical have not been performed. ANIMAL/PLANT STUDIES: Cumene is metabolized primarily to the secondary alcohol, 2-phenyl-2-propanol in animals. This alcohol and its conjugates are readily excreted by rodents. Increases in organ weights, primarily the kidney weughts are the most prominent effects observed in rodents readily exposed to cumene by either the oral or inhalation route. No adverse effects were observed in rat or rabbit fetuses whose mothers had been exposed to cumene during fetal development. Although no multigenerational reproductive studies have been performed using cumene, the rapid metabolism and excretion, coupled with the lack of effects on sperm morphology in a subchronic study, suggest that it has a low potential for reproductive toxicity. Most genotoxicity test data with cumene are negative. Inadequate data, especially measured exposure information, exist to allow a quantitative evaluation of the risk to populations of aquatic ot terrestrial organisms from exposure to cumene. Values indicate a slight potential for bioconcentration in fish. There are no data on the bioaccumulation in fish.

Petroleum distillates are central nervous system depressants and cause pulmonary damage. (A600)

U055; As stipulated in 40 CFR 261.33, when cumene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Cumene is included on this list. Effective date: 12/28/84; Sunset date: 12/28/94.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Cumene is produced, as an intermediate or a final product, by process units covered under this subpart.

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. Cumene 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. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

(CA) CALIFORNIA 770 ug/l

(FL) FLORIDA 700 ug/l

(MN) MINNESOTA 300 ug/l

(NH) NEW HAMPSHIRE 800 ug/l

Cumene is used as a thinner for paints, lacquers, and enamels and as a component of high octane fuels. Cumene is also used in the manufacture of phenol, acetone, acetophenone, and methylstyrene.

In occupational settings, the main route of exposure to cumene is via inhalation during cumene manufacturing, processing, and use, primarily in the manufacture of phenol and acetone. [ACGIH]

Painting (Solvents) [Category: Paint]

Used primarily in the production of phenol and acetone

Used as a thinner for paints, enamels, and lacquers and as a solvent for fats and resins and as such has been suggested as a replacement for benzene.

Component of high octane aviation fuel used in WWII; in production of styrene /Former/

(1972) NEGLIGIBLE

(1975) 2.07X10+10 GRAMS

(1984) 2.24X10+9 g

Exports totaled 465 million lbs in 1998.

(1972) 2.02X10+11 GRAMS

(1975) 9.50X10+10 GRAMS

2023: 4,000,000,000 - <5,500,000,000 lb

(1972) 1.04X10+12 GRAMS

(1975) 9.09X10+11 GRAMS

(1984) 1.70X10+12 g

(1988) 4.5X10+9 lb

For more U.S. Production (Complete) data for Isopropylbenzene (13 total), please visit the HSDB record page.

For phenol; 34% for acetone; 1% for alpha-methylstyrene and misc applications (1972)

Oxidation for phenol/acetone production; 1.8% polymerization for alpha-methylstyrene; 0.2% exports (1985)

CHEMICAL PROFILE: Cumene. Demand: 1986: 3.7 billion lb; 1987: 4.0 billion lb; 1991 /projected/: 4.3 billion lb. (Includes exports; in addition, 328 billion lb were imported in 1986).

More than 95% of the cumene produced is used as feedstock for the production of phenol and acetone.

Demand: 1998, 6.7 billion lbs; 1999, 6.9 billion lbs; 2003, 8.0 billion lbs

In the UOP /Universal Oil Products/ process a fixed bed consisting of polyphosphoric acid on a silica support is used as the catalyst. The reaction takes place mainly in the gas phase at greater than or equal to 200 °C and greater than or equal to 2 MPa. Pure propene or propene with a propane content greater than or equal to 5% is used as raw material, together with benzene (minimum purity 99.5%) in up to 12-fold molar excess; this leads to high distillation costs in the product work-up. The yield of cumene is 97% based on benzene and 90% based on propene. The losses are caused by overalkylation and oligomerization of the propene. The high-boiling residue contains 50 - 60% diisopropylbenzenes (o- : m- : p- ratio 1 : 2 : 2 - 3) and numerous other byproducts. It is not possible to recycle these products to the alkylation reactor, because polyphosphoric acid has no transalkylation properties.

The second industrial process works in the liquid phase at 50 - 80 °C; aluminum chloride or the liquid double compound formed from aluminum chloride, (isopropyl-)benzene, and hydrogen chloride is employed as the catalyst. This complex is separated from the product stream, as a heavy phase and is returned to the alkylation reactor. Except for a small purge stream higher alkylated byproducts are recycled to the alkylation step, whereby essentially complete use of both benzene and propene bound in di- and triisopropylbenzenes is achieved by transalkylation. The yield of cumene, referred to benzene and propene, is 99% and 98 %, respectively.

(1) Alkylation of benzene with propylene (phosphoric acid catalyst), (2) distillation from coal tar naptha fractions or from petroleum.

Manufactured from propylene and benzene utilizing an acidic catalyst, eg, solid phosphoric acid.

High purity cumene can be easily produced from either refining or steam cracker-derived propylene.

Grades: Technical, research, pure.

0.16% wt in gasoline

99.9% MIN ASSAY

Cosmetics product ingredient: Cumene

Information on 118 consumer products that contain Cumene in the following categories is provided:

Oil and Gas Drilling, Extraction, and Support activities

Benzene, (1-methylethyl)-: ACTIVE

Occurs in a variety of petroleum distillates and commercial solvents

Union Carbide's 640 million lb per yr Penuelas, PR and Marathon Oil's 210 million lb per yr Texas City, TX plant are on standby; Monsanto closed its Alvin, TX plant IN 1983

Isopropylbenzene forms a charge-transfer complex with ozone in a number of solvents. When this charge-transfer complex was photolyzed at -75 °C or warmed greater than -40 °C, reactions formed cumyl hydrotrioxide and ring-ozonated products (in a ratio of 70/30).

Thirty-second highest-volume chemical produced in U.S. (1991).