2,4-디클로로톨루엔

Log Kow= 4.24

4.24

4.09

1.2498 (NTP, 1992) - Denser than water; will sink

1.2476 @ 20 °C/20 °C

1.25 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.02

INSOL IN WATER

Solubility in water, g/100ml at 20 °C: (very poor)

93 °C

199 °F, open cup

87 °C c.c.

385 to 387 °F at 760 mmHg (NTP, 1992)

201 °C @ 760 mm Hg

at 101.3kPa: 200 °C

7.7 °F (NTP, 1992)

-13.5 °C

-13.5 °C

0.45 [mmHg]

0.458 mm Hg at 25 °C

Vapor pressure, kPa at 50 °C: 0.4

This chemical does not meet GHS hazard criteria for 5.8% (4 of 69) of reports.

Warning

H315 (27.5%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P271, P273, P280, P302+P352, P304+P340, P318, P319, P321, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: Benzene, 2,4-dichloro-1-methyl-

Status: Active Update: 06-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13164

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 87 °C explosive vapour/air mixtures may be formed.

COMBUSTIBLE /DICHLOROTOLUENE/

Fire point: 383 °F, open cup

May be a strong irritant; [HSDB] In high-dose animal studies, causes somnolence, elevation of liver enzymes, fatty liver degeneration, and acute tubular necrosis; [RTECS]

The major hazards encountered in the use and handling of 2,4-dichlorotoluene stem from its toxicologic properties and flammability. Exposure to 2,4-dichlorotoluene may occur via inhalation or dermal routes, primarily resulting from occupational activities including those associated with its use as a high boiling solvent and as an intermediate in organic synthesis. Because it is a strong irritant, personnel involved with 2,4-dichlorotoluene should wear boots, protective gloves, and goggles, at a minimum. Avoid breathing vapor or, to enter a contaminated area freely, wear full face mask self-contained breathing apparatus which provides eye protection. Broken packages containing 2,4-dichlorotoluene should not be handled without protective equipment. Any of this material which contacts the body must be washed away with copious amounts of water. While substance must be moderately heated before ignition occurs (flashpoint: 199 °F, open cup), 2,4-dichlorotoluene is, nevertheless, considered a combustion hazard. Normal fire fighting procedures may be employed, which includes the use of "alcohol" foam, or dry chemical extinguishing agents. Water also may be used in flooding quantities as a fog or spray (solid streams may be ineffective) to extinguish the fire or cool containers. Application of water should be from as far a distance as possible. This substance is considered to be normally stable, even under fire exposure conditions. Nonetheless, it should be stored away from sparks, flames, or other sources ignition. Shipping regulations and other DOT regulatory requirements should be consulted before transport. If 2,4-dichlorotoluene spills, keep material out of water sources and sewers; building dikes to contain the flow as necessary. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.

Shafer KH et al; Anal Chem 56 (2): 237-40 (1984). Detection of aromatic hydrocarbons in hazardous waste, by gas chromatography-Fourier transform IR spectometry and by gas chromatography-mass spectometry.

Sixt S et al; Chemosphere 30 (12): 2397-414 (1995). The acute toxicity to Photobacterium phosphoreum (Microtox test) of a set of 80 chlorinated compounds, containing aliphatics, benzenes, toluenes, phenols and anilines, was investigated using 'Theoretical Linear Solvation Energy Relationship' parameters. Quantitative Structure Activity Relationships were developed for chemical and toxicological subsets. Molecular volume revealed to be the most important Theoretical Linear Solvation Energy Relationship descriptor. For the complete data set and for the phenols the Theoretical Linear Solvation Energy Relationship descriptors are superior to log P alone. In the case of the phenols this is related to electronic information being inherent in the electrostatic parameter q-, which is correlated to the pKa of the compounds. For the benzenes a quadratic term in Vmc was very useful for the description of the toxicity, Many of the chlorinated aliphatics do not fit the narcosis II Quantitative Structural Activity Relationship. Enhanced chemical reactivity due to the chlorine substitution may lead to activation or biodegradation of these compounds. The attempt to establish narcosis II Quantitative Structural Activity Relationships for the polar narcotic chloroanilines and -phenols was unsuccessful. It seems that some chloroanilines interact directly with the bioluminescence system of P. phosphoreum. The authors emphasize that the concept of baseline narcosis implies that the pure narcosis II mechanism decreases with increasing log P. The site of toxic action for narcosis II is therefore thought to be hydrophilic. Uncoupling of oxidative phosphorylation seems to play a minor role in the photobacterium than it does in fish. Reasons for this may be the ability of bacteria to crack and detoxify aromatic rings or the relative robustness of oxidative phosphorylation in bacteria.

Simple aromatic halogenated organic compounds, such as 2,4-DICHLOROTOLUENE, are very unreactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

To extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)

Use carbon dioxide, powder, water spray.

Fresh air, rest.

Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth.

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.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Chlorotoluenes/

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

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. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Remove vapour with fine water spray.

AVOID PROLONGED BREATHING OF VAPOR. USE WITH ADEQUATE VENTILATION. /4-Chlorotoluene/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Chlorotoluenes/

Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Chlorotoluenes/

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4,800(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 2,4-dichlorotoluene will have only slight mobility in soil(SRC). 2,4-Dichlorotoluene was found to be susceptible to anaerobic biodegradation in soil slurry microcosms under methanogenic conditions; complete degradation required 130 days(4). The predominant product of this reaction was 4-chlorotoluene, a small amount of 2-chlorotoluene was also produced(4). Volatilization of 2,4-dichlorotoluene may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.2X10-3 atm-cu m/mole(SRC), using a recommended regression equation(5) and from dry soil surfaces(SRC) based on a measured vapor pressure of 0.458 mm Hg(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4,800(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that 2,4-dichlorotoluene may adsorb to suspended solids and sediment in water(SRC). Based on limited data, this compound may biodegrade under anaerobic conditions(SRC). 2,4-Dichlorotoluene was found to be susceptible to anaerobic biodegradation in soil slurry microcosms under methanogenic conditions; complete degradation required 130 days(3). The predominant product of this reaction was 4-chlorotoluene, a small amount of 2-chlorotoluene was also produced(3). 2,4-Dichlorotoluene may volatilize from water surfaces based on an estimated Henry's Law constant of 4.2X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 4 hours and 5 days, respectively(1,SRC), although adsorption to sediment or suspended material in water may attenuate this process(SRC). An estimated BCF value of 1000(1,SRC), from a measured log Kow(2), suggests that 2,4-dichlorotoluene will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5). The half-life of 2,4-dichlorotoluene in the Rhine River in The Netherlands is 1 day as determined by measuring concentration differences over a reach of the river(6,SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-dichlorotoluene, which has a measured vapor pressure of 0.458 mm Hg at 25 °C(2), should exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dichlorotoluene 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 12 days(3,SRC).

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, 2,4-dichlorotoluene was identified in discharges of the following industrial categories (frequency of occurrence, median concn in ppb): rubber processing (1; 314.9), organic chemicals (11; 20.9), publicly owned treatment works (5; 40.4)(1). The highest effluent concn was 1424 ppb in the paint and ink industry(1). 2,4-Dichlorotoluene has been detected, but not quantified, in water samples at the Love Canal(2).

The Koc of 2,4-dichlorotoluene is estimated as approximately 4,800(SRC), using a measured log Kow of 4.24(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 2,4-dichlorotoluene will have only slight mobility in soil(SRC).

2,4-Dichlorotoluene (CAS # 95-73-8) was evaluated for acute oral toxicity. The test substance was administered by oral intubation to male albino rats (2/group) at dosage levels of 100, 215, 464, 1000, 2150, and 4640 mg/kg of body weight. No mortality occurred. At 4640 mg/kg, toxic effects included prostration and tremors followed by depression, ataxia, labored respiration, blood-like crust around nostril, urine stains, and rough haircoat at 24- hours. Toxic effects gradually subsided, but rough coat persisted until termination.

2,4-Dichlorotoluene's production and use as an intermediate in the manufacture of fungicides, dyes, pharmaceuticals, preservatives, and peroxides(1) or for the manufacture of 2,4-dichlorobenzyl chloride and 2,4-dichlorobenzoyl chloride(2) may result in its release to the environment through various waste streams(SRC).

2,4-Dichlorotoluene was found to be susceptible to anaerobic metabolism in soil slurry microcosms under methanogenic conditions. 2,4-Dichlorotoluene, at an initial concentration of 800 uM was completely degraded after 130 days; 50% degradation required about 90 days. The predominant product of this reaction was 4-chlorotoluene, a small amount of 2-chlorotoluene was also produced(1).

Used as a high-boiling solvent and an intermediate (pesticides, fungicides, dyes, pharmaceuticals, preservatives, and peroxides); [HSDB]

HIGH BOILING SOLVENT; INTERMEDIATE FOR ORG SYNTHESIS /DICHLOROTOLUENE/

2,4-Dichlorotoluene is used as a herbicide intermediate & for the manufacture of 2,4-dichlorobenzyl chloride and 2,4-dichlorobenzoyl chloride.

2,4-Dichlorotoluene is used via its side-chain-chlorinated intermediates to produce fungicides, dyes, pharmaceuticals, preservatives, and peroxides (curing agents for silicones and polyesters).

2,4-Dichlorotoluene represents 80-85% of the dichlorotoluene fraction in chlorination of p-chlorotoluene with antimony trichloride or zirconium tetrachloride catalysts. It is separated from 3,4-dichlorotoluene by fractional distillation.

Chlorination of 4-chlorotoluene in the presence of ring chlorination catalysts (eg chlorides of iron, antimony, or zirconium) leads to 2,4- and 3,4-dichlorotoluene in a ratio of ca. 4:1; the two can be separated by fractional distillation. Only traces of other dichlorotoluenes are formed. ... 2-Chlorotoluene is converted primarily into 2,4-dichlorotoluene when sulfuryl chloride is used as the chlorinating agent.