Dodecylbenzene is an aromatic hydrocarbon compound with the molecular formula of C6H5CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3, CAS 123-01-3. The appearance is colorless transparent liquid, slightly purple fluorescence, with aromatic fragrance. It is insoluble in water, but can dissolve petroleum hydrocarbons well. Because the dodecyl on the benzene ring is a long-chain alkyl, there are normal isomers and different isomers, which can produce linear and various branched it. Sulfonation reaction, acylation reaction and thermal cracking reaction can occur. In industry, benzene and long-chain alkenes are mainly condensed to produce it in the presence of acidic catalysts. The alkenes used include α- Olefins, normal olefins and isomers. Mainly used as raw material of surfactant.
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Chemical Formula |
C18H30 |
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Exact Mass |
246 |
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Molecular Weight |
246 |
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m/z |
246 (100.0%), 247 (19.5%), 248 (1.8%) |
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Elemental Analysis |
C, 87.73; H, 12.27 |
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1. Preparation of plasticizer:
Alkyl sulfonyl chloride has a wide range of applications in industry, such as the production of synthetic detergent sodium alkyl sulfonate, the plasticizer alkyl sulfonate phenyl ester of PVC resin, etc., especially the alkyl sulfonate resin (known as T-50 petroleum ester in industry) has excellent electrical properties, weather resistance and low heat consumption, which has been widely used as plasticizer in various PVC products, especially in wire and cable formulations. The method of synthesizing dodecylbenzene sulfonate from product is as follows: it 1200kg, specific gravity 0.871 (15 ℃), in a reactor made of vinyl chloride, the reactor is equipped with lead coil for cooling, mercury arc lamp, gas distributor, thermometer and gas discharge pipe, etc., and chlorine and sulfur dioxide with a ratio of 1:1.1 are introduced. After mixing, they are introduced at room temperature, and the light is turned on at the same time, with a wavelength of 280nm, The ratio of light power and dodecyl benzene amount is 0.8 W/kg. The reaction is exothermic. The temperature is controlled at 25 ℃~32 ℃ with cooling water, and the amount of mixed gas is 30 kg/h. The reaction generates hydrogen chloride and a small amount of unreacted gas is recovered by spraying hydrochloric acid with water through the exhaust pipe. When the specific gravity of the reactant is 0.996, the gas is stopped, and the dissolved residual gas is blown away with dry compressed air, and the dodecyl benzene sulfonyl chloride is 1440kg, with a saponification value of 163, The conversion rate is 45%.
2. Preparation of surfactant:
Dodecylbenzen can be used to synthesize dodecyl benzene sulfonates, such as sodium dodecyl benzene sulfonate, which is a common anionic surfactant and widely used in detergents and detergents. Add 35 mL (34.6 g) of dodecyl benzene into a 250 mL four-mouth bottle equipped with a stirrer, thermometer, drip funnel and reflux condenser, slowly add 35 mL of 98% sulfuric acid with stirring, and the temperature shall not exceed 40 ℃. After adding, raise the temperature to 60~70 ℃, and react for 2 h. Lower the temperature of the sulfonation mixture to 40~50 ℃, slowly add an appropriate amount of water (about 15mL), pour it into the separating funnel, stand still for a moment, layer by layer, drain the lower layer (water and inorganic salt), and retain the upper layer (organic phase). Prepare 80mL of 10% sodium hydroxide solution, add it into a 250mL four-mouth bottle, about 60-70mL, stir and slowly drip the above organic phase, control the temperature to 40-50 ℃, use 10% sodium hydroxide to adjust pH=7-8, and record the total amount of 10% sodium hydroxide. In the above reaction system, add a small amount of sodium chloride, filter after the percolation ring test is clear, and obtain a white paste product, namely sodium dodecyl benzene sulfonate.
Dodecylbenzen is an aromatic hydrocarbon compound with 12 carbon linear alkyl groups, with a molecular formula of C18H30. It is a colorless and transparent liquid at room temperature and pressure, with purple fluorescence. As an important basic raw material in the field of fine chemical engineering, its unique chemical structure and physical properties make it widely applicable in multiple industrial fields.
Application of sulfonated products:
Dodecylbenzenesulfonic acid (DBSA): After neutralization with sodium hydroxide, sodium dodecylbenzenesulfonate (SDBS, CAS number 25155-30-0) is generated, which is the second largest synthetic surfactant in the world.
Performance advantages:
The critical micelle concentration (CMC) is low and the surface activity is strong.
Resistant to hard water and high electrolyte concentration, suitable for industrial cleaning.
The biodegradation rate is greater than 90% (OECD 301 standard), which meets environmental requirements.
Industrial production case:
Sulfonation process: using sulfur trioxide air mixture sulfonation method, the sulfonation rate can reach over 98%.
Neutralization process: Recovering unreacted benzene through a dual membrane process (ultrafiltration+reverse osmosis) to reduce wastewater COD.
Pharmaceutical intermediates
Acylation product development:
Example of Friedel Crafts Acylation Reaction:
Raw materials: n-dodecylbenzene+acetyl chloride (catalyst AlCl ∝)
Product: 4-Dodecylphenylacetophenone (yield approximately 75%)
Pharmacological activity: Some acylation products have anti-inflammatory and antibacterial activities and can be used as drug side chain modifying groups.
Application example:
Antifungal drug intermediates: Long chain alkylbenzene structures can enhance the lipophilicity of drug molecules and improve targeted delivery efficiency.
Liquid crystal material monomer: The combination of rigid benzene rings and flexible long-chain alkyl groups endows the material with unique phase transition properties.
Dyes and functional materials
Dye dispersant:
Mechanism of action: SDBS acts as a dispersant, with long-chain alkyl groups adsorbed on the surface of pigment particles, and benzenesulfonic acid groups extending into the aqueous phase, forming a spatially hindered stable system.
Typical applications: Preparation of water-based colorants such as phthalocyanine blue and carbon black.
Polymer material modification:
Polymer blending: as a compatibilizer to improve the compatibility between polyolefins and polar polymers.
Nano material dispersion: used for surface modification of carbon nanotubes and graphene to enhance their dispersibility in epoxy resins.
Other industrial uses
Thermal oil:
Performance advantages: high boiling point (>330 ℃), low vapor pressure, suitable for closed heat transfer systems.
Application areas: Heating media for plastic processing and petrochemicals.
Organic synthetic solvents:
As a non-polar solvent, Dodecylbenzene is used for Grignard reagent reactions and synthesis of metal organic compounds.
Lubricant additives:
The long-chain alkylbenzene structure can enhance the extreme pressure and anti-wear performance of lubricating oil.
1. It contains impurities such as dialkyl benzene, alkyl indene, alkyl tetrahydronaphthalene, etc., which are dehydrated by molecular sieve during refining, and then distilled in a packed tower with glass single ring.
2. In industry, benzene and long-chain alkenes are mainly used to condense under acidic catalyst to produce dodecylbenzen. The alkenes used include α- Olefins, normal olefins and isomers. The industrialized method is alkane dehydrogenation method, which uses normal alkanes as raw materials, dehydrogenates to olefins on Pt-Al2O3 catalyst, and then alkylates with benzene to produce n-dodecyl and other finished products.
3. Propylene tetramerization takes propene-propane fraction as raw material, generates propylene tetramer under the action of phosphoric acid - diatomite catalyst, and then generates branched alkylbenzene with benzene under the action of aluminum trichloride catalyst, and then obtains the finished product after rectification.
In addition, alkylbenzene can also be produced by paraffin cracking and chloroalkane and benzene condensation. Most of the commercially available it is a mixture, and its alkyl chain range is mostly C11 to C13. It is mainly used as raw material of surfactant, and is used for production of detergent, emulsifier, dispersant, industrial detergent, etc.
Chemical property:
1. It is not easy to catch fire. It is easy to react with fuming sulfuric acid or SO3 to form dodecylbenzene sulfonic acid.
2. Generally, aromatic hydrocarbons are more toxic, and benzene has the strongest effect on the central nervous system and blood. When the alkyl side chain is carried, the irritation and anesthesia to the mucosa are enhanced, but in the organism, because the side chain is oxidized into alcohol and then into carboxylic acid, there is no damage to the hematopoietic function.
Melting point 3 ° C (lit.), Boiling point 185-188 ° C/15 mmHg (lit.) 331 ° C (lit.), Density 0.856 g/mL at 25 ° C (lit.), Vapor pressure 0.1 hPa (50 ° C), Refractive index n20/D 1.482 (lit.), Flash point>230 ° F, Storage condition Store below+30 ° C, Solubility Acetonitrile (Slightly), Chloroform (Slightly), Acidity coefficient (pKa) 50 (at 25 ℃), Form Liquid, Colorless
adverse reaction
Dodecylbenzene (chemical formula C18H30) is a colorless and transparent liquid with an aromatic odor. It is insoluble in water and easily soluble in organic solvents. As an important chemical raw material, it is widely used in the synthesis of detergents, surfactants, lubricant additives, and other fields. However, its chemical properties and environmental behavior may have adverse effects on human health and the ecological environment.
Health hazards: potential risks of direct contact and long-term exposure
Skin and mucosal irritation
Dodecyl benzene is irritating to the skin and mucous membranes, and direct contact may cause the following reactions:
Skin irritation
Contact may cause redness, itching, burning sensation, and in severe cases, contact dermatitis. The mechanism may be related to the breakdown of the skin barrier by lipophilic properties, leading to inflammatory reactions.
Eye irritation
Splashing into the eyes can cause conjunctival congestion, tearing, photophobia, and even corneal damage. Animal experiments have shown that a 0.1% concentration of dodecylbenzene solution can cause significant eye irritation in rabbits.
Respiratory irritation
Inhaling its vapor or aerosol may irritate the respiratory mucosa, causing symptoms such as cough, sore throat, and chest tightness. Long term exposure may trigger chronic bronchitis.
Acute poisoning symptoms
High concentration exposure or ingestion may lead to acute poisoning, with typical symptoms including:
Digestive system
Nausea, vomiting, abdominal pain, diarrhea, and in severe cases, gastrointestinal bleeding.
Nervous system
Dizziness, headache, fatigue, blurred consciousness, and even coma. In animal experiments, the oral LD ₅₀ of rats was 9200mg/kg, indicating low acute toxicity, but high doses may still be life-threatening.
Liver and kidney damage
Long term exposure may damage liver and kidney function, leading to elevated transaminase levels and abnormal biochemical indicators such as proteinuria.
Chronic health effects
Long term low-dose exposure may cause chronic health problems
Allergy
Some individuals may experience allergic reactions to it, manifested as recurrent rash, asthma, and other symptoms.
Potential carcinogenicity
Although there is currently no conclusive evidence to suggest that dodecylbenzene is carcinogenic, its metabolites (such as epoxides) may have genetic toxicity and require further research.
Reproductive toxicity
Animal experiments have shown that high-dose exposure may affect reproductive system function, but human data is limited.
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