1,2,4-Trichlorobenzene CAS 120-82-1 is an aromatic hydrocarbon consisting of a benzene ring substituted with three chlorine atoms at the 1, 2, and 4 positions. It is one of the three isomers of trichlorobenzene and is the most commercially significant and thermally stable among them. It is a chlorinated solvent and chemical intermediate with a characteristic, sharp, aromatic odor.1,2,4-Trichlorobenzene (1,2,4-TCB) is a high-performance, high-boiling chlorinated aromatic solvent and intermediate prized for its exceptional thermal stability and powerful solvating ability. Its primary advantage lies in enabling industrial processes that require a robust, inert medium under demanding temperature and chemical conditions where common solvents fail.
Nome :
1,2,4-TrichlorobenzeneNº CAS. :
120-82-1MF :
C₆H₃Cl₃MW :
181.45Pureza :
99%Aparência :
Colorless to pale yellow, clear, oily liquid.Condição de armazenamento :
Store in a cool, well-ventilated area away from heat and ignition sources.Chemical Properties
IUPAC Name: 1,2,4-Trichlorobenzene
Chemical Formula: C₆H₃Cl₃
Molecular Weight: 181.45 g/mol
Structure: A benzene ring with chlorine atoms on carbons 1, 2, and 4.
Appearance: Colorless to pale yellow, clear, oily liquid.
Melting Point: 17 °C (62.6 °F) - often a liquid at room temperature.
Boiling Point: 213 °C (415.4 °F)
Density: 1.46 g/cm³ at 20 °C (heavier than water)
Vapor Pressure: 0.3 mmHg at 20 °C
Solubility: Very low in water (approx. 30 mg/L at 25 °C). Miscible with most common organic solvents (e.g., ethanol, diethyl ether, benzene).
Stability: Chemically stable under normal conditions. Resistant to strong acids and alkalis. Can be oxidized under extreme conditions. Does not polymerize.
Flammability: Combustible liquid with a flash point of 110 °C (230 °F).
Key Reactivity: The chlorine atoms, especially the one at the 4-position (para to two chlorines), can be displaced by nucleophiles under harsh conditions (high temperature, strong base, or catalysis), making it a useful intermediate. It undergoes electrophilic aromatic substitution with difficulty due to the deactivating chlorine substituents.
Biological Activities
Toxicity: Classified as harmful. Acute exposure primarily affects the central nervous system (CNS), causing symptoms like dizziness, headache, and incoordination. It is also a skin and eye irritant.
Chronic Effects: Long-term exposure can lead to liver and kidney damage. It is considered a potential occupational hazard for these organs.
Environmental Fate & Ecotoxicity: Highly persistent in the environment due to its chemical stability and low biodegradability. It is bioaccumulative and toxic to aquatic life with long-lasting effects. It adsorbs strongly to soil and sediment.
Carcinogenicity: Not classifiable as to its carcinogenicity to humans (Group 3) by IARC. However, some animal studies have shown evidence of tumorigenicity.
Metabolism: In mammals, it is metabolized primarily in the liver via cytochrome P450-mediated oxidation to phenolic derivatives, which can be conjugated and excreted.
Biosynthesis
Natural Occurrence: Not known to be produced by natural biological processes. It is a xenobiotic compound (human-made).
Industrial Production: Produced exclusively by chemical synthesis.
1.Chlorination of Benzene or Monochlorobenzene: The primary method involves the direct chlorination of benzene or monochlorobenzene in the presence of a Lewis acid catalyst (e.g., iron(III) chloride). The reaction produces a mixture of di-, tri-, and higher chlorinated benzenes, which are separated by fractional distillation.
2.Isomer Separation: The crude trichlorobenzene fraction is distilled to isolate the 1,2,4-isomer from the less stable 1,2,3- and 1,3,5-isomers.
Applications
Key Advantages & Benefits
1. Exceptional High-Temperature Stability & Inertness
Benefit: Maintains chemical integrity and solvating power at temperatures exceeding 200°C, with a high flash point (110°C) that enhances safety in hot processes.
Application Scenario: As a high-temperature heat transfer fluid in a closed-loop system for chemical manufacturing, it efficiently carries thermal energy to reactors without decomposing or forming gums, ensuring consistent process control and long fluid life.
2. Powerful, Selective Solvency for Demanding Formulations
Benefit: Excellently dissolves a wide range of non-polar to moderately polar materials (waxes, resins, dyes, sulfur) while being immiscible with water, allowing for clean phase separations.
Application Scenario: In the specialized dyeing of high-performance polyester fibers for automotive airbags, 1,2,4-TCB acts as a carrier solvent under pressure at 120-130°C. It swells the fiber, allowing deep and uniform dye penetration to achieve the critical color fastness and durability standards required.
3. Superior Dielectric Properties for Electrical Applications
Benefit: Possesses high dielectric strength and resistivity, making it an effective insulating and cooling fluid that is non-flammable under typical operating conditions.
Application Scenario: Used as a dielectric impregnating fluid in high-voltage underground power cable splices. Its fluidity allows it to fill voids, while its electrical properties prevent corona discharge and dissipate heat, significantly extending the splice's operational lifetime in demanding utility networks.
4. Effective Intermediate for Synthesis
Benefit: The chlorine atoms, particularly the one at the 4-position, can be selectively displaced under controlled conditions to synthesize more complex chlorinated aromatics.
Application Scenario: Serves as a key starting material in the multi-step synthesis of advanced herbicides and agrochemicals, where its specific substitution pattern provides the necessary molecular backbone for biological activity and metabolic stability.
1,2,4-Trichlorobenzene (CAS 120-82-1) is a specialist's chemical whose advantages are defined by a specific set of performance properties—high boiling point, thermal stability, and potent solvency. Its use is justified primarily in niche, often legacy industrial applications where its technical performance outweighs its significant environmental, health, and regulatory liabilities. While safer, more sustainable alternatives like silicone oils or specialized esters have replaced it in many areas, 1,2,4-TCB remains relevant in carefully controlled, closed-system processes where its unique physical-chemical profile is difficult to replicate. For engineers and chemists, it represents a powerful but constrained tool, necessitating a rigorous cost-benefit analysis that includes compliance and lifecycle disposal.
FAQs
Q1: What are the main advantages of 1,2,4-TCB as a solvent or fluid?
A: Its key advantages are its high boiling point (213°C), chemical inertness, excellent solvating power for non-polar materials, and good dielectric strength. These make it suitable for high-temperature processes and specialized electrical applications where common solvents fail.
Q2: How should it be stored and handled safely?
A: Store in a cool, well-ventilated area away from heat and ignition sources. Use containers made of stainless steel or lined steel. Keep tightly closed. Handle with appropriate PPE: chemical-resistant gloves (nitrile, Viton), safety goggles, and vapor respirators if ventilation is inadequate. Ground containers to prevent static discharge.
Q3: Is it compatible with common metals and plastics?
A: It is compatible with stainless steel, glass, and fluorinated polymers (e.g., Teflon, Viton). It can attack some elastomers and plastics like polyvinyl chloride (PVC) or polyethylene, causing swelling or degradation. Always conduct compatibility tests.
Q4: What are the key regulatory and compliance considerations?
A: It is strictly regulated due to its Persistence, Bioaccumulation, and Toxicity (PBT) profile.
REACH (EU): Subject to authorization; its use is restricted.
EPA (USA): Regulated under TSCA. Listed as a Priority Pollutant under the Clean Water Act.
Transport: Classified as an Environmental Hazard (Marine Pollutant) and Harmful for transport (UN 2321).
Disposal: Must be treated as hazardous waste. Incineration in a hazardous waste incinerator equipped with acid gas scrubbers is the typical method.
Q5: What are the main alternatives, and why might 1,2,4-TCB still be chosen?
A:
Solvent Alternatives: Higher-boiling hydrocarbon solvents (e.g., heavy aromatic naphtha) or ester-based solvents. 1,2,4-TCB is chosen when superior solvating power for specific dyes/polymers or higher thermal stability is critical.
Dielectric Fluid Alternatives: Silicone oils, perfluorocarbons, or biodegradable ester-based fluids. 1,2,4-TCB may still be used in legacy equipment or where its specific combination of dielectric constant, thermal conductivity, and cost is unmatched for a niche application.
Q6: What analytical methods are used for quality control and environmental monitoring?
A: Common methods include:
Gas Chromatography (GC) with electron capture (ECD) or mass spectrometric (MS) detection for purity and trace analysis.
High-Performance Liquid Chromatography (HPLC) with UV detection.
For environmental samples (water, soil), EPA Methods 8121 or 8270 are standard.
Q7: Can it be recycled or reclaimed?
A: Yes, through distillation. Used solvent or dielectric fluid can be purified by fractional distillation to remove impurities and degradation products. This is both an economic and environmental imperative to reduce waste and virgin material use, but must be done in compliance with all hazardous waste regulations.
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