Benzotrichloride

Description

Exhaustive chlorination of the side-chain of toluene leads to benzotrichloride (trichloromethyl benzene, a,a,a-trichlorotoluene, phenyl chloroform) [98-07-7]. The compound was first synthesized in 1858 by L. SCHISCHKOFF and A. ROSING, using the reaction of PCl5 with benzoyl chloride. Benzotrichloride is now produced on a large scale, since it serves as an important intermediate in the preparation of acid chlorides (benzoyl chloride), dyes, herbicides, pesticides, and other products.

Physical properties

Benzotrichloride is a colorless liquid with a pungent odor and is irritating to the eyes and mucous membranes. It fumes in moist air.Benzotrichloride is freely soluble in alcohol, ether, and chloroform. It is only slightly soluble in water (0.05 g/L at 5 ℃, 0.25 g/L at 39 ℃). The solubility of chlorinein 100 g of benzotrichloride is 5.1 g at 30 ℃, 3.4 g at 50 ℃, 1.3 g at 100 ℃.

Chemical properties

Benzotrichloride is a combustible, colorless to yellow-brown, oily liquid that fumes on contact with air. It has a penetrating odor.

The Uses of Benzotrichloride

α,α,α-Trichlorotoluene was used in determination of chlorinated toluenes in effluents of wastewater treatment plants and textile industries by closed loop stripping analysis.

The Uses of Benzotrichloride

In dye chemistry. In organic syntheses (source of benzenyl group).

The Uses of Benzotrichloride

Chemical intermediate primarily in benzoyl chloride production; dye intermediate

The Uses of Benzotrichloride

Benzotrichloride is used mainly to produce benzoyl chloride, for which purpose it is either partially hydrolyzed with water or else reacted with benzoic acid. It is also of some significance in the production of pesticides (through transformation into benzotrifluoride), ultraviolet stabilizers, and dyes.

Definition

ChEBI: (trichloromethyl)benzene is an organochlorine compound that is toluene in which all three hydrogens of the methyl group have been replaced by chlorines. It is used as an intermediate in organic synthesis and dye chemistry. It has a role as a carcinogenic agent. It is a member of benzenes, a volatile organic compound and an organochlorine compound.

General Description

Benzotrichloride appears as a clear colorless to yellowish colored liquid with a penetrating odor. Denser than water and vapors are heavier than air. May be toxic by inhalation or ingestion. Burns skin, eyes, and mucous membranes. Insoluble in water. Used to make dyes and other chemicals.

Air & Water Reactions

Hydrolyzes in the presence of moisture. The reaction is rather slow due to low solubility in water.

Reactivity Profile

Benzotrichloride hydrolyzes in the presence of moisture. Benzotrichloride reacts with water, lime, ammonia, strong alkalis, organic amines, chlorates and acids.

Hazard

Highly toxic by inhalation, fumes highly irritant. Eye, skin, and upper respiratory tract irri- tant. Probable carcinogen.

Health Hazard

Toxic by inhalation; fumes are highly irritating to skin and mucous membranes. May cause death or permanent injury after very short exposure to small quantities. A suspected carcinogen.

Fire Hazard

Benzotrichloride may react violently with water. Fire may produce irritating or poisonous gases. Flammable/poisonous gases may accumulate in tanks and hopper cars. Materials may ignite combustibles (wood, paper, oil, etc.). Produces toxic and corrosive fumes when Benzotrichloride reacts with water or steam. Similar to hydrochloric acid; material will react with water or steam to produce toxic and corrosive fumes. Hydrolyzes in presence of water forming benzoic and hydrochloric acids.

Toxicology

The acute oral toxicity of benzotrichloride is 2180 mg/kg in male rats and 1590 mg/kg in female rats. The inhalative LC50s are higher than 600 mg/m3 in male rats and about 500 mg/m3 in female rats after a 4-h exposure. Benzotrichloride irritates the skin and eyes. The compound proved to be mutagenic in bacterial test systems. Dermal application of benzotrichloride resulted in elevated tumor incidence in mice.

Potential Exposure

Benzotrichloride is used as a chemical and dye intermediate; extensively used in the dye industry for the production of Malachite green, Rosamine, Quinoline red, and Alizarin yellow A. It can also be used to produce ethyl benzoate. Commercial grades may contain hydrochloric acid, benzylidene chloride, or benzyl chloride.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. If victim is conscious, administer water ormilk. Do not induce vomiting. Medical observation isrecommended for 24
48 h after breathing overexposure, aspulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consideradministering a corticosteroid spray.

Carcinogenicity

Benzotrichloride is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

storage

(1) Color Code—White: Corrosive or ContactHazard; Store separately in a corrosion-resistant location.(2) Color Code—Blue: Health Hazard/Poison: Store in asecure poison location. Before entering confined spacewhere benzotrichloride may be present, check to make surethat an explosive concentration does not exist. Store intightly closed containers in a dark, cool, well-ventilatedarea. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storagecontainers to process containers. Drums must be equippedwith self-closing valves, pressure vacuum bungs, and flamearresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames,are prohibited where this chemical is used, handled, orstored in a manner that could create a potential fire orexplosion hazard. A regulated, marked area should be established where this chemical is handled, used, or stored incompliance with OSHA Standard 1910.1045.

Shipping

UN2226 Benzotrichloride, Hazard class: 8; Labels: 8—Corrosive material.

Incompatibilities

Benzotrichloride decomposes on heating, on contact with acids and/or water, producing toxic and corrosive hydrogen chloride and benzoic acid. Reacts violently with strong oxidizers, iron and other metals, alkali and earth alkali metals; bases and organic substances, and may cause fire and explosions. On contact with air it emits toxic and corrosive hydrogen chloride. Attacks many metals in presence of water. Attacks many plastics.

Waste Disposal

Incineration with flammable solvent added in incinerator with afterburner and alkaline scrubber.