Benzalchlorid

Other Classes -> Halogenated Monoaromatics

Carcinogens

log Kow= 3.217 (calculated)

3.22

PUNGENT ODOR

FAINT AROMATIC ODOR

1.26 (EPA, 1998) - Denser than water; will sink

1.26

Relative density (water = 1): 1.26

1.26 @25 °C

less than 1 mg/mL at 63 °F (NTP, 1992)

INSOL IN WATER

SOL IN DILUTE ALKALI

> 10% in ethanol

> 10% in ether

Soluble in most org solvents.

198 °F (NTP, 1992)

93 °C

93 °C c.c.

401 °F at 760 mmHg (EPA, 1998)

205 °C

205 °C

205 °C @760 [mm Hg]

2.48 °F (EPA, 1998)

-16.4 °C

-17 °C

-17 °C

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 13.2% (30 of 227) of reports.

Danger

H302 (86.8%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Benzene, (dichloromethyl)-

Chemical: Benzene, dichloromethyl-

Benzene, dichloromethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, dichloromethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Benzene, (dichloromethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, (dichloromethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 06-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/15963

Status: Active Update: 03-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11710

Fire may produce irritating or poisonous gases. Runoff from fire control water may give off poisonous gases and may cause pollution. Cylinder may explode in the heat of fire. Reacts with water to release hydrochloric acid. (EPA, 1998)

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Acute: vapors are highly irritating to eyes. May be fatal if inhaled, swallowed, or absorbed through skin. (EPA, 1998)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

USEPA; Chemical Hazard Information Profile: Benzal chloride (Draft) (1982)

ITC/USEPA; Information Review #204 (Draft) (Dichloromethyl)benzene (1980)

USEPA; Health and Environmental Effects Profile for Benzal Chloride (1988) EPA/600/X-85/046. /Includes/ listings of hazardous constituents of a wide range of waste streams under Section 3001 of the Resource Conservation and Recovery Act (RCRA) and to provide health related limits for emergency actions under Section 101 of the Comprehensive Environmental Response, Compensation and Liability Act (CERCLA).

Keep unnecessary people away and isolate hazard area. Stay upwind and keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing.

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

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. 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.

Signs and Symptoms of Benzal Chloride Exposure: Benzal chloride may be very irritating to the skin, eyes, and mucous membranes. Eye irritation may be severe, and permanent eye damage may result. Lacrimation (tearing) is common. Other signs and symptoms of acute exposure may include headache, dizziness, weakness, fatigue, irritability, itching of the skin, profuse sweating, insomnia, tremors, unsteadiness, and central nervous system excitation or depression. Gastrointestinal effects may include nausea, vomiting, cramps, anorexia, and diarrhea. Pulmonary edema and disturbance of liver function may also occur.

General First Aid:

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.

A potential 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 potential 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.

Personal protection: complete protective clothing including self-contained breathing apparatus. 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.

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.

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Immediate precautionary measure

TERRESTRIAL FATE: Benzal chloride hydrolyzes rapidly in water (half-life of 7.4 minutes at 25 °C;) therefore, hydrolysis is expected to be a dominant fate process in moist soil. A theoretical Koc value of 510 can be estimated based on the molecular structure which indicates medium to low soil mobility; however, leaching in moist soils is not expected to be significant since the compound is expected to hydrolyze first. Evaporation of benzal chloride from dry surfaces is expected to occur. (SRC)

AQUATIC FATE: When released to water, benzal chloride will hydrolyze rapidly (half-life of 7.4 minutes at 25 °C and pH 7) and produce benzaldehyde as a hydrolysis product. Due to the rapid hydrolysis, aquatic volatilization, bioconcentration, and adsorption to sediments are not expected to be significant. (SRC)

ATMOSPHERIC FATE: Benzal chloride will react in the vapor-phase with photochemically produced radicals at an estimated half-life rate of 1.84 days. Hydrolysis in the presence of sufficient atmospheric moisture may be possible. (SRC)

Cough. Laboured breathing. Sore throat.

Redness. Pain.

Redness. Pain.

Burning sensation. Further see Inhalation.

Based on molecular topology and quantitative structure-activity relationship analysis, the Koc value for benzal chloride can be estimated to be about 510(1,SRC) which is indicative of medium to low soil mobility(SRC). Due to the relatively rapid hydrolysis in water, leaching of benzal chloride in moist soils is not expected to be significant since it is expected to hydrolyze first(SRC).

STRONG ... LACRIMATOR.

No data clearly relating cancer to exposure to benzal chloride were available to the /IARC/ Working Group. However, benzoyl chloride manufacturing workers, among whom an excess of respiratory cancer has been reported (6 cases in total), were also potentially exposed to benzal chloride.

... Categorized as moderately toxic /by inhalation and ingestion/.

Benzal chloride is produced as a by-product during the commercial manufacture of benzyl chloride(1,2); currently, this is the only source by which benzal chloride is produced industrially(SRC). Fugitive emissions and waste streams from benzyl chloride manufacture are a potential source of benzal chloride(SRC). Since benzal chloride has no current industrial uses(SRC), commercial use of the compound is not a current source of pollution(SRC).

Based on a computer-calculated log Kow value of 3.217(1), the BCF value for benzal chloride can be estimated to be 164(2,SRC). Due to the relatively rapid hydrolysis of benzal chloride in water, bioconcentration in aquatic organisms is not likely to occur(SRC).

The Henry's Law constant for benzal chloride at 25 °C can be estimated to be 0.0007 atm cu m/mol by a bond-structural contribution method(1,SRC) which can be used to estimate a volatilization half-life of 5.3 hr from a river 1 m deep flowing at 1 m/sec with a wind velocity of 3 m/sec(2,SRC). However, the hydrolysis half-life of 7.4 minutes at 25 °C indicates that volatilization from water is not significant relative to hydrolysis(SRC ). Benzal chloride fumes in air(3) and has a reported vapor pressure of 0.3 mm Hg at 20 °C(4) which suggests that evaporation from dry surfaces will occur(SRC).

Benzal chloride (redistilled commercial material, purity & impurities not specified) has been reported to be mutagenic in reversion assays using Salmonella typhimurium strain TA100 (the only strain tested) & in Escherichia coli strain WP2 hcr; mutagenicity required metabolic activation by a microsomal fraction of the livers of rats induced by Arochlor 1254. It was also positive in a rec-assay Bacillus subtilis.

The LC16, LC50, & LC84 values for 2 hr exposures to benzal chloride were 160, 400, & 1000 mg/cu m (24, 61 & 152 ppm), respectively, for rats, & 80, 210, & 550 mg/cu m (12, 32 & 84 ppm), respectively for mice. The order of decreasing toxicity among the chlorinated toluenes was: benzotrichloride > benzal chloride > benzyl chloride. Thus, in single 2 hr exposure of mice & rats to 100 mg/cu m (15.2 ppm), all 3 cmpd produced central nervous system excitation, irritation of the eyes & respiratory mucosa & slowed respiration in order of activity described above. Hyperemia of the extremities was also noted; at 1000 mg/cu m (152 ppm) mice exhibited motor automatism, & rats showed twitching of peripheral muscles. When rats were exposed to 100 mg/cu m of each of the compounds in inhalation chamber, continuously for 1 mo, the degree of wt loss was related to the same order of activity as in the acute studies.

... Two groups, each consisting of 19 or 20 female ICR mice, 7 wk old ... were given skin applications of 25 ul (22 mg) benzene (controls) or 25 ul of a 9.2% soln of benzal chloride in benzene (vol/vol; 2.9 mg benzal chloride /treatment; about 75-100 mg/kg body weight, assuming body weights of 24-40 g/ twice weekly for 50 wk (total dose, about 289 mg/animal). All mice were killed at wk 82. ... No skin tumor was observed in any control. Of the 19 benzal chloride treated mice, 14 (74%) had died by the end of the experiment; 12 (63%) developed tumors: 9 with squamous cell carcinomas of the skin (p < 0.01), 2 with skin fibrosarcoma, & 1 with a lymphoma; lung adenomas were reported in 5 treated mice & 2 controls. /Fukuda et al, 1981/.

Benzal chloride and benzotrichloride induced mutation and DNA damage in bacteria.

For more Non-Human Toxicity Excerpts (Complete) data for BENZAL CHLORIDE (6 total), please visit the HSDB record page.

As stipulated in 40 CFR 261.33, when dichloromethyl(benzene) 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).

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. Benzyl dichloride is produced, as an intermediate or final product, by process units covered under this subpart.

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).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzal chloride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Used in dyes and to make benzaldehyde and cinnamic acid; [Hawley]

IN DYES /FORMER USE/

MANUFACTURE OF BENZALDEHYDE & CINNAMIC ACID. /FORMER USE/

To prepare benzoyl chloride.

2023: 75,000 - <500,000 lb

2023: 1,000,000 - <5,000,000 lb

(1977) AT LEAST 9.13X10+8 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Processing aids not otherwise specified

Intermediate

CHLORINATION OF TOLUENE IN THE PRESENCE OF LIGHT & IN THE ABSENCE OF CATALYSTS THAT PROMOTE RING CHLORINATION.

Benzal chloride can be manufactured in 70% yield by chlorination with 2.0-2.2 moles of chlorine per mole toluene.

Benzal choride is ... formed by reaction of dichlorocarbene (CCl2) with benzene.

All Other Chemical Product and Preparation Manufacturing

All Other Basic Organic Chemical Manufacturing

Benzene, (dichloromethyl)-: ACTIVE

Benzene, dichloromethyl-: ACTIVE