1,3-Dichlorobenzene

Flammable agents - 2nd degree

Volatile Organic Compound (VOC) (Volatile Organic Compound (VOC)/Semi-Volatile Organic Compound (SVOC))

log Kow = 3.53

3.53

3.44

1.2884 at 68 °F (USCG, 1999) - Denser than water; will sink

1.2884 at 20 °C/4 °C

Relative density (water = 1): 1.288

1.2884 @ 20°C

less than 1 mg/mL at 70 °F (NTP, 1992)

Sol in ethanol, ether; very soluble in acetone

In water, 125 mg/L at 25 °C

Solubility in water: none

146 °F (NTP, 1992)

63 °C

63 °C

343 °F at 760 mmHg (NTP, 1992)

173 °C

173 °C

173 °C @760 [mm Hg]

Warning

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

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P319, P321, P330, P332+P317, P333+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Benzene, 1,3-dichloro-

Hazard Traits - Endocrine Toxicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System

Status: Active Update: 13-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/18076

1,3-Dichlorobenzene: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Irritating vapors including hydrogen chloride are produced. (USCG, 1999)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 63 °C explosive vapour/air mixtures may be formed.

Combustible

m-Dichlorobenzene is ignitable only with difficulty.

INHALATION: Causes headache, drousiness, unsteadiness. Irritating to mucous membranes. EYES: Severe irritation. SKIN: Severe irritation. INGESTION: Irritation of gastric mucosa, nausea, vomiting, diarrhea, abdominal cramps and cyanosis. (USCG, 1999)

An eye, nose, and throat irritant; [HSDB] Severely irritating to eyes and skin; A mucous membrane irritant; Can cause drowsiness and unsteadiness after inhalation; [CAMEO] A skin, eye, and respiratory tract irritant; May cause liver and kidney injury; [ICSC] An irritant; [MSDSonline]

USEPA; Ambient Water Quality Criteria Doc: Dichlorobenzenes (1980) EPA 440/5-80-039

Dangerous Prop Ind Mater Rept 5 (1): 56-63 (1985). Review of 1,3-dichlorobenzene toxicology, health hazards, and safety measures.

Dichlorobenzenes, Dangerous Prop Ind Mater Rpt 6 (2): 50-7 (1986). Review of dichlorobenzene toxicology, health hazards and safety measures.

USEPA; Drinking Water Criteria Doc: ortho-Dichlorobenzene, meta-Dichlorobenzene, para-Dichlorobenzene (Draft) 174p (1986)

For more Special Reports (Complete) data for 1,3-DICHLOROBENZENE (6 total), please visit the HSDB record page.

U071; As stipulated in 40 CFR 261.33, when 1,3-dichlorobenzene, 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).

Fire Extinguishing Agents: Water, foam, carbon dioxide or dry or dry chemical. (USCG, 1999)

Use water spray, powder, 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 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. Refer for medical attention .

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.

WATER, FOAM, CARBON DIOXIDE, DRY CHEM ...

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.). Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /o-Dichlorobenzene/

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. 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. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ /o-Dichlorobenzene/ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /p-Dichlorobenzene/

Environmental considerations: Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved in region of 10 ppm or greater concn, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /o-Dichlorobenzene; p-Dichlorobenzene/

Evacuate and restrict persons not wearing protective equipment for the area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand,earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped.

[40 CFR 240-280, 300-306, 702-799 (7/1/2006)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U071, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U071, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

... Halogenated compounds may be disposed of by incineration provided they are blended with other compatible wastes or fuels so that the composite contains less than 30% halogens and the heating value is from 7000 to 9000 BTU/lb. Liquid injection, rotary kiln, and fluidized bed incinerators are typically used to destroy liquid halogenated wastes. ... Temperatures of at least 2000-2200 °F and residence times /of more than 2 sec/ ... are required for the destruction of halogenated aromatic hydrocarbons. /Halogenated aromatic hydrocarbons/

Potential candidate for rotary kiln incineration, with a temperature range of 820 to 1,600 °C, and a residence time of seconds. Also a potential candidate for liquid injection incineration, with a temperature range of 650 to 1,600 °C, and a residence time of 0.1 to 2 seconds.

For more Disposal Methods (Complete) data for 1,3-DICHLOROBENZENE (6 total), please visit the HSDB record page.

Personal protection: filter respirator for organic gases and particulates 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.

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.

Contact lenses should not be worn when working with this chemical.

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /o-Dichlorobenzene/

Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /o-Dichlorobenzene/

Dichlorobenzene isomers were detected in human blood samples taken from residents of Love Canal, NY at concns of 1-68 ng/L(1). The combined 1,3-, 1,4-dichlorobenzene concn in the breath of Los Angeles, CA residents was 3.5 and 2.8 ug/cu m and residents of Contra Costa, CA had a concn of 2.5 ug/cu m(2).

A survey of human milk from the general population of Canada found 1,3-dichlorobenzene residues in 17 percent of the samples at an avg concn of 2 ppb(1). 1,3-Dichlorobenzene was detected in human milk at less than 5 ug/kg(2).

Acute (short-term) exposure to 1,4-dichlorobenzene, via inhalation in humans, results in irritation of the skin, throat, and eyes. Chronic (long-term) 1,4-dichlorobenzene inhalation exposure in humans results in effects on the liver, skin, and central nervous system (CNS). No information is available on the reproductive, developmental, or carcinogenic effects of 1,4-dichlorobenzene in humans. A National Toxicology Program (NTP) study reported that 1,4-dichlorobenzene caused kidney tumors in male rats and liver tumors in both sexes of mice by gavage (experimentally placing the chemical in their stomachs).

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 19000 ug/L for 48 hr; Effect: population biomass

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 30000 ug/L for 48 hr; Effect: general population changes

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, renewal, 25 °C, pH >7; Concentration: 7 mg/L for 24 hr; Effect: behavior, equilibrium

EC50; Species: Daphnia magna (Water flea, age <24 hr); Conditions: freshwater, static, 25 °C, pH > or =7.0, dissolved oxygen > or = 58%; Concentration: 7000 ug/L for 24 hr; Effect: intoxication, immobilization

For more Ecotoxicity Values (Complete) data for 1,3-DICHLOROBENZENE (33 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), a Koc value of 300(2) indicates 1,3-dichlorobenzene is expected to have moderate mobility in soil(SRC). Volatilization of 1,3-dichlorobenzene is expected from moist soil surfaces given its Henry's Law constant of 2.8X10-3 atm-cu m/mole at 20 °C(3). Volatilization of 1,3-dichlorobenzene from dry soil surfaces is expected based on a vapor pressure of 2.15 mm Hg at 25 °C(4). A 0% theoretical BOD in sludge over a 4 week incubation period(5) suggests that biodegradation is expected to be slow in soil(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), a Koc value of 300(2) indicates that 1,3-dichlorobenzene is expected to adsorb to suspended solids and sediment in water(SRC). 1,3-Dichlorobenzene is expected to volatilize from water surfaces(3) given its Henry's Law constant of 2.8X10-3 atm-cu m/mole at 20 °C(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 and 120 hours, respectively(SRC). According to a classification scheme(5), BCF values in the range of 60 to 740, measured in carp(6) and trout(7), suggest that bioconcentration in aquatic organisms is moderate to high. A theoretical BOD of 0% in sludge over a 4 week incubation period(6) suggests that biodegradation is expected to be slow in water under aerobic conditions. 1,3-Dichlorobenzene was slowly biodegraded by an acclimated anaerobic sediment slurry obtained from the Tsurumi River, Japan(8). The first-order biodegradation rate constant was 0.0016 days-1, corresponding to a half-life of about 433 days(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-dichlorobenzene, which has a vapor pressure of 2.15 mm Hg at 25 °C(2), is expected to exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,3-dichlorobenzene 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 about 22 days(SRC), calculated from its rate constant of 7.2X10-13 cu cm/molecule-sec at 25 °C(3). 1,3-Dichlorobenzene does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to undergo direct photolysis by sunlight(4).

1,3-Dichlorobenzene was identified, not quantified in 6 of 234 table ready foods in the US at an avg concn of 7.36 ppb(1). 1,3-Dichlorobenzene was detected in fruits (0.0044 ug/g) and vegetables and potatoes (0.0011 ug/g)(2). 1,3-Dichlorobenzene was detected in potato core at a concn of 0.096 ug/kg and pea seeds at a concn of 0.087 ug/kg(3).

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

Inhalation

Trace concn (less than 5 ug/kg) of 1,3-dichlorobenzene were detected in Yugoslavian human milk.

ENVIRONMENTAL: A survey of human milk from the general population of Canada found 1,3-dichlorobenzene residues in 17 percent of the samples at an avg concn of 2 ppb(1). 1,3-Dichlorobenzene was detected in human milk at less than 5 ug/kg(2).

1,3- and 1,4-DCB were detected together in whole human milk with mean and maximum concentrations of 6 and 75 ppb, respectively. These isomers were detected in milkfat samples at a mean concentration of 161 ppb and a maximum concentration of 4,180 ppb. 1,2-, 1,3-, and 1,4-DCB measured separately in whole human milk samples had concentrations of 9, <5, and 25 ppb, respectively, while the milk fat of these samples contained 230 ppb of 1,2-DCB and 640 ppb of 1,4-DCB.

The liver damage caused in rats by 1,3-dichlorobenzene is accompanied by induction of xenobiotic metabolizing enzymes of the phenobarbital type. In rats, a disturbance in thyroid homoeostasis can develop by hepatic enzyme induction: 1,3-dichlorobenzene induces glucuronosyl transferases. The conjugation of the thyroid hormones thyroxine (T4) and triiodothyronine (T3) is increased by the induction of glucuronosyl transferases. This leads to an increased release of T4 and T3 in the thyroid follicles.

Based on monitoring data at three USA urban sites (Los Angeles, Phoenix, Oakland), the AVDI for 1,3-dichlorobenzene has been estimated to be 0.8-1.1 ug/day(1). The AVDI (via inhalation exposure only) of combined 1,2-, 1,3- and 1,4-dichlorobenzene isomers in the Netherlands is 7.0 ug/day(2).

/AQUATIC SPECIES/ ... For fathead minnows, chronic toxicities were estimated from 32-33 day embryo through early juvenile development exposures. The ranges between the highest no observable effect concentrations and lowest observed effect concentrations were 1000-2300, 570-1000, and 240-410 ug/L for 1,3-dichlorobenzene, 1,4-dichlorobenzene, 1,2,3,4-tetrachlorobenzene, respectively. The tissue concentrations associated with the no observable effect concentration and lowest observed effect concentration for 1,3-dichlorobenzene, 1,4-dichlorobenzene, and 1,2,3,4-tetrachlorobenzene were 120-160, 70-100, and 640-1000 ug/g, respectively. Mean bioconcentration factors obtained in these tests were 97, 10, 2400, 8400, and 22,000 for 1,3-dichlorobenzene, 1,4-dichlorobenzene, 1,2,3,4-tetrachlorobenzene, pentachlorobenzene, and hexachlorobenzene, respectively. 96 hr median lethal concentration values, obtained for juvenile fish, for 1,3-dichlorobenzene, 1,4-dichlorobenzene, and 1,2,3,4-tetrachlorobenzene were 7800, 4200, and 1100 ug/L, respectively.

/AQUATIC SPECIES/ A test was developed using Tetrahymena pyriformis in order to determine the toxicity of various chemicals. Precultured Tetrahymena pyriformis was exposed for 24 hr at 30 °C to various concentrations of chemicals. The concentration of the chemical, at which the proliferation of Tetrahymena pyriformis was restricted to one-half of the blank test (EC50), was determined. The method, applied to 57 chemicals, demonstrated that it could be used to detect the chemicals at low concentrations rapidly and with ease. The EC50 values showed a good relationship with 48 hr LC50 values for Himedaka (Oryzias latipes), and could be explained on the basis of the partition coefficient between water and n-octanol. EC50 for m-dichlorobenzene was 130 mg/L (880 umol/L).

/AQUATIC SPECIES/ Developmental, genetic, and reproductive toxicities of benzene, chlorobenzene, and o-, m-, and p-dichlorobenzenes were investigated in sea urchin, Paracentrotus lividus. Toxicity order depended on whether the target organ was embryo or sperm. Benzene was active in sea urchin sperm causing developmental and mitotic abnormalities in offspring. Benzene also showed a significant increase in developmental defects following embryo exposure. For chlorobenzene, developmental defects were seen when the concentration was increased to 10(-4). M-Dichlorobenzene caused a strong increase in developmental defects and also in mitotic abnormalities.

U071; As stipulated in 40 CFR 261.33, when 1,3-dichlorobenzene, 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 promulagated 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. Benzene, 1,3-dichloro- is included on this list. Effective date 10/4/82; Sunset date 10/4/92.

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. m-Dichlorobenzene is produced, as an intermediate or a 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 100 lb or 45.4 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).

(AZ) ARIZONA 620 ug/l

(CT) CONNECTICUT 210 ug/l

(ME) MAINE 60 ug/l

(WI) WISCONSIN 1250 ug/l

Study of the relationship between the formation of 2,4- and 3,5- dichlorophenyl methyl sulfones, metabolites of m-dichlorobenzene (m-DCB), and their inducing effect on hepatic microsomal drug-metabolizing enzymes in rats. When m-DCB was injected ip into bile duct cannulated rats, little or no methyl sulfones were detected in blood, liver, kidneys, adipose tissue, or bile. In the antibiotic pretreated rats dosed with m-DCB, metabolite concentrations in the blood and the three tissues markedly decreased. These findings suggest that the formation of methylsulfonyl metabolites from m-DCB depends largely upon the metabolism by intestinal microflora. The increasing effects of m-DCB administration on the activities of aminopyrine and aniline metabolizing enzymes and the contents of cytochromes p450 and b5 in hepatic microsomes were scarcely observed in the bile duct cannulated and antibiotic pretreated rats, in which the drug metabolism enzymes were able to be induced by phenobarbital treatment. On the other hand, in rats administered 2,4- or 3,5-dichlorophenyl methyl sulfone, hepatic distribution of each methyl sulfone was similar to that in intact rats, and the degree of increase of the above four parameters was nearly the same as that in the intact rats. These findings provide evidence that the induction of drug metabolizing enzymes by m-DCB is not due to the action of m-DCB but is due to its methylsulfonyl metabolites.

M-Dichlorobenzene yields N-acetyl-S-(2,4-dichlorophenyl)-L-cysteine, 2,4-dichlorophenol, and 3,5-dichlorophenol in rabbit. /from table/

When fed to rabbits, m-dichlorobenzene yielded glucuronides (31%, sulfates (11%), mercapturic acid (9%) and catechols (4%). ...2,4-Dichlorophenylmercapturic acid and 3,5-dichlorocatechol were also observed...

1,3-Dichlorobenzene was reported to be among several metabolites of gamma-pentachloro-1-cyclohexane in corn and pea seedlings.

The S-containing metabolites of m-dichlorobenzene (m-DCB) were identified by using gas chromatography-mass spectrometry and disposition of m-DCB metabolites studied. In the blood, urine and feces of rats dosed with m-DCB, 2,4- and 3,5-dichlorophenyl methylsulfoxide and 3,5- and 2,4-dichlorophenyl methanesulfonate emerged, while their possible precursors, 3,5- and 2,4-dichlorophenyl methyl sulfide were not detected in the blood, urine, and feces. However, after heating the alkalinized urine and feces, the methyl sulfides appeared. ...

For more Metabolism/Metabolites (Complete) data for 1,3-DICHLOROBENZENE (8 total), please visit the HSDB record page.

1,3-Dichlorobenzene is readily absorbed after ingestion.

The dichlorobenzenes may be absorbed through the lung, gastrointestinal tract, and intact skin. Relatively low water solubility and high lipid solubility favor their penetration of most membranes by diffusion, including pulmonary and GI epithelia, the brain, hepatic parenchyma, renal tubules, and the placenta. /Dichlorobenzenes/

Information on the quantitative absorption of 1,3-DCB in humans and animals is not available for any route of exposure; however, absorption of the compound can be inferred from studies that have detected 1,3-DCB or metabolites in the breast milk, blood, and fat of humans and in the bile and urine of exposed animals. Distribution is believed to be similar to the other DCB isomers, but data demonstrating this are not presently available. Similar to the other DCB isomers, 1,3-DCB is initially metabolized by cytochrome P-450 enzymes, followed by extensive conjugation, primarily to glutathione, has been reported. 1,3-DCB is eliminated mainly in the urine, similar to the other DCB isomers.

Children can be exposed to DCBs prenatally, as indicated by the detection of all three isomers in placenta samples, as well as through breast feeding. 1,2-DCB concentrations measured in whole human milk range from 3 to 29 ppb. 1,3- and 1,4-DCB were detected together in whole human milk with mean and maximum concentrations of 6 and 75 ppb, respectively. These isomers were detected in milkfat samples at a mean concentration of 161 ppb and a maximum concentration of 4,180 ppb. 1,2-, 1,3-, and 1,4-DCB measured separately in whole human milk samples had concentrations of 9, <5, and 25 ppb, respectively, while the milk fat of these samples contained 230 ppb of 1,2-DCB and 640 ppb of 1,4-DCB.

Used as a fumigant, insecticide, and chemical intermediate; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Fumigant and insecticide /Former use/

/REACTED WITH/ POTASSIUM HYDROXIDE OR SODIUM HYDROXIDE TO PRODUCE CHLOROPHENOLS; USED IN THE PREPARATION OF ARYLENE SULFIDE POLYMERS IN THE PPS POLYMERIZATION PROCESS

... Used in the production of various herbicides and insecticides. It is also important in the production of pharmaceuticals and dyes.

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1489]

1,3-Dichlorobenzene is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Chlorination of monochlorobenzene.

... By Sandmeyer procedure from the appropriate chloroaniline, along with o- and p-dichlorobenzenes, by chlorination of chlorobenzene.

Pure 1,3-dichlorobenzene can be obtained by working up the unavoidable 1,3-dichlorobenzene-containing mother liquor that results from p-dichlorobenzene crystallization. Combined crystallization/distillation processes, extractive distillation, or separation on zeolites are feasible.

... Synthetic processes which lead directly to 1,3-dichlorobenzene: 1) Chlorination of benzene in the gas phase at 200 - 500 °C in a tube or in molten salt; 2) Sandmeyer reaction of 3-chloroaniline or direct replacement of the amino group by chlorine; 3) Reaction of 1,3,5-trialkylbenzene with chlorine in the presence of I2 or ferric chloride to give 2,6-dichloro-1,3,5-trialkylbenzene, the alkyl groups then being cleaved in the presence of aluminum chloride; 4) Chlorination of 1,3-dinitrobenzene or chloronitrobenzene at a temperature above 200 °C; 5) Two-step chlorination of benzenesulfonyl chloride or diphenyl sulfone, with sulfur dioxide being eliminated; 6) Cleavage of sulfur dioxide or carbon dioxide from the corresponding disulfonyl chlorides or dicarbonic acid chlorides at temperatures above 200/300 °C in the presence of catalysts; 7) Catalytic dechlorination of 1,2,4-trichlorobenzene with hydrogen in the vapor phase; 8) Isomerization of 1,2- and 1,4-dichlorobenzene at a temperature of 150 - 200 °C in the presence of catalysts containing aluminum chloride. The conversion to 1,3-dichlorobenzene is said to be quantitative if the isomerization is carried out in an antimony pentafluoride - hydrogen fluoride system at 20 °C.

Benzene, 1,3-dichloro-: ACTIVE

Separation of mixt containing m-, o-, and p-dichlorobenzenes by distillation and crystallization: Mueller, Wolz, French patent 1,374,863 (1964 to Bayer), CA 62, 493e (1965), corresponding to British patent 999,845.