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4,6-Dimethyldibenzothiophene (DM-DPT) is an organic compound with the chemical formula C20H16S, CAS 1207-12-1, and a corresponding molar mass of 296.4 g/mole. It is a solid compound that typically appears as a light yellow to orange colored crystal. Has certain UV absorption and fluorescence emission characteristics. It has a strong absorption peak in the ultraviolet light region (about 250-350 nanometers), while emitting yellow green fluorescence in the blue to green light region (about 400-550 nanometers). The crystal structure is maintained by non covalent interactions between molecules, such as van der Waals forces and π - π stacking. It has various applications, mainly used as antioxidants, whitening agents, UV protectors, anti-inflammatory agents, skin cell growth promoters, and cosmetic fragrances. For cosmetics manufacturing, it can improve the antioxidant capacity, whitening effect, sunscreen effect, anti-inflammatory effect, and fragrance quality of products, providing consumers with a better skincare and beauty experience.
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Chemical Formula |
C14H12S |
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Exact Mass |
212 |
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Molecular Weight |
212 |
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m/z |
212 (100.0%), 213 (15.1%), 214 (4.5%), 214 (1.1%) |
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Elemental Analysis |
C, 79.20; H, 5.70; S, 15.10 |
4, 6-dimethyldibenzothiophene is an organic sulfur compound with significant industrial and research value. Its discovery and research process is closely related to the development of petrochemistry, environmental science and catalytic science. The following is an introduction from aspects such as its chemical structure analysis, discovery background, research progress and industrial applications.
Chemical Structure Analysis and Naming
The molecular formula of 4,6-DMDBT is C₁₄H₁₂S and its molecular weight is 212.31. Its chemical structure consists of two benzene rings bridged by sulfur atoms to form a dibenzothiophene skeleton, with a methyl group attached to each of the 4th and 6th carbon atoms. This structure endows it with unique physicochemical properties, such as a high melting point (153-157°C), boiling point (364.9°C), and low solubility, enabling it to exist in a stable form in petroleum.
Discovery Background and Early Research
Research on sulfur Compounds in Petrochemicals
In the middle of the 20th century, with the rapid development of the petroleum industry, the presence of sulfur compounds in petroleum gradually attracted attention. Sulfur compounds not only affect the quality of fuel but also release sulfur dioxide during combustion, leading to environmental problems such as acid rain. Therefore, the research on the separation, identification and removal technologies of sulfur compounds in petroleum has become a hot topic.
The discovery of dibenzothiophene compounds
Dibenzothiophene (DBT), a typical sulfur-containing aromatic compound in petroleum, was isolated and identified as early as the beginning of the 20th century. With the advancement of analytical techniques, researchers have discovered that there are various derivatives of DBT in petroleum. Among them, 4,6-DMDBT has attracted much attention due to its high fire resistance (difficulty in removal).
The first separation and identification of 4,6-DMDBT
In the late 20th century, through techniques such as high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS), researchers successfully separated and identified 4,6-DMDBT from petroleum fractions. Its structure was confirmed by methods such as nuclear magnetic resonance (NMR) and X-ray diffraction.
Research Progress and Scientific Significance
Due to the steric hindrance effect of its methyl group, 4,6-DMDBT makes it difficult for sulfur atoms to approach the active sites of the catalyst, thus becoming a "stubborn molecule" in the HDS reaction. Studies have shown that traditional catalysts (such as CoMo/Al₂O₃, NiMo/Al₂O₃) have a relatively low removal efficiency for 4,6-DMDBT, which has prompted researchers to develop new catalysts and reaction processes.
To improve the HDS efficiency of 4,6-DMDBT, researchers have designed a variety of new catalysts, such as supported nickel phosphide (Ni₂P), tungsten phosphide (WP), and metal sulfides supported by molecular sieves, etc. Meanwhile, through density functional theory (DFT) calculations, the adsorption configuration and reaction path of 4,6-DMDBT on the catalyst surface were revealed, providing theoretical guidance for catalyst design.
In recent years, progress has been made in the research on microbial degradation of 4,6-DMDBT. For instance, certain strains of Sphingomonas can degrade 4,6-DMDBT through a co-metabolic pathway, generating intermediate products such as methylbenzothiophene-2, 3-dione. This discovery provides new ideas for biological desulfurization technology.
Industrial Applications and Environmental Impacts
The demand for ultra-deep desulfurization technology
With increasingly strict environmental protection regulations, the sulfur content standards in fuel have been continuously lowered (for example, the EU VI standard requires that the sulfur content in diesel be less than 10 ppm). 4,6-DMDBT, as one of the difficult-to-remove sulfur compounds in petroleum, its efficient removal has become the key to ultra-deep desulfurization technology.
The development of new desulfurization processes
To address the challenges of 4,6-DMDBT, the industrial sector has developed a variety of new desulfurization processes, such as adsorption desulfurization, oxidation desulfurization and biological desulfurization, etc. Among them, the adsorption desulfurization technology efficiently removes 4,6-DMDBT by using selective adsorbents (such as molecular sieves and activated carbon), and has the advantages of mild operating conditions and low energy consumption.
Environmental and health impacts
4,6-DMDBT will release sulfur dioxide and polycyclic aromatic hydrocarbons (PAHs) during the combustion process, causing harm to the environment and human health. Therefore, reducing the content of 4,6-DMDBT in petroleum products is of great significance for improving air quality and reducing the risk of acid rain.
Future Research Directions
Research and development of high-efficiency catalysts
Future research will continue to focus on the development of efficient and stable HDS catalysts, especially selective catalysts for difficult-to-remove sulfur compounds such as 4,6-DMDBT.
In-depth exploration of the reaction mechanism
Through in-situ characterization techniques (such as infrared spectroscopy and X-ray absorption spectroscopy) and theoretical calculations, the reaction mechanism of 4,6-DMDBT on the catalyst surface was further revealed, providing more accurate theoretical guidance for catalyst design.
The industrial application of biological desulfurization technology
The research on microbial degradation of 4,6-DMDBT is still at the laboratory stage. In the future, problems such as strain stability, reaction rate and process scale-up need to be solved to promote the industrial application of biological desulfurization technology.
As a stubborn sulfur compound in diesel fuel, the removal technology for 4,6-dimethyldibenzothiophene (4,6-DMDBT) is not only crucial for energy efficiency but also closely tied to environmental protection and human health. From the limitations of traditional hydrodesulfurization (HDS) to breakthroughs in novel catalytic systems, and from laboratory innovations to industrial applications, every advancement embodies the wisdom and dedication of researchers. Looking ahead, with the convergence of green chemistry and artificial intelligence technologies, we have every reason to believe that 4,6-DMDBT removal techniques will usher in a new era of enhanced efficiency and environmental sustainability.
Chemical Synthesis Methods
The synthetic pathway using 3-methylcyclohex-2-enone as the raw material
This route prepares 2-bromo-3-methylcyclohexanone through conjugated addition reaction, then couples it with 2-methylthiophenol to form the intermediate 3-methyl-2 -(2-methylphenylthiyl) cyclohexa-2-enone, and finally condenses it under the action of polyphosphoric acid to generate 4, 6-dimethyl-1,2,3, 4-tetrahydrodibenzothiophene. This intermediate is hydrogenated with zinc and trifluoroacetic acid to generate 4, 6-dimethyl-1,2,3,4, 4A, 9b-hexahydrodibenzothiophene, and then the target product 4,6-DMDBT is obtained through dehydrogenation reaction.
Analysis of Key Reaction Steps
Conjugated addition reaction: Trimethylaluminum reacts with 2-bromo-2-cyclohexene-1-one under the catalysis of copper bromide to form 2-bromo-3-methylcyclohexanone, providing a key intermediate for the subsequent coupling reaction.
Coupling and condensation reactions: The coupling reaction of the intermediate with 2-methylthiophenol and the condensation reaction mediated by polyphosphoric acid jointly constructed the dibenzothiophene skeleton.
Hydrogenation and dehydrogenation reactions: The hydrogenation and dehydrogenation steps of hexahydrointermediates, precisely synthesizing the target product by regulating reaction conditions.
Current Situation of Industrial Production
Optimization direction of production process
Catalyst carrier modification: The preparation of AlₓZr₁₀₀ Spring ₓ carriers with different Al₂O₃ concentrations by sol-gel method and the loading of NiWS active components can significantly improve the hydrodesulfurization performance of the catalyst. Research shows that the introduction of ZrO₂ can enhance the dispersion and reduction of the NiMoS phase and optimize the physicochemical properties of the catalyst.
Reaction condition exploration: In response to the deep hydrodesulfurization requirements of 4,6-DMDBT, researchers continuously optimized parameters such as reaction temperature, pressure, and hydrogen flow rate to enhance the yield and purity of the target product.
Main producers and production capacity
At present, many chemical enterprises at home and abroad have the production capacity of 4,6-DMDBT. For instance, Wuhan Xinyang Ruihe Chemical Technology Co., Ltd. produces hundreds of kilograms of 4.6-DMDBT annually and supplies it stably to many large domestic enterprises. The company has advanced R&D bases and production bases, with production capabilities ranging from kilograms to large-scale.
Quality Control and Standards
Purity and impurity control
The purity of industrial-grade 4,6-DMDBT is usually required to be ≥97%, and some high-end applications even require it to be ≥99%. During the production process, the purity of raw materials, reaction conditions and post-treatment processes must be strictly controlled to reduce the generation of impurities. For instance, the purity of the product can be further enhanced through methods such as recrystallization and chromatographic separation.
Analysis and detection methods
The purity, structure and impurity content of 4,6-DMDBT were accurately analyzed by techniques such as high performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR). These methods have the advantages of high sensitivity and high resolution, which can ensure that the product quality meets the standard requirements.
Safety and Environmental Protection Requirements
Safety production measures
The production process of 4,6-DMDBT involves dangerous chemicals such as flammable, explosive, toxic and harmful substances, and it is necessary to strictly abide by the safety production norms. For instance, in the operation of reaction vessels, material transportation and storage, etc., measures such as explosion prevention, fire prevention and poison prevention should be taken to ensure the safety of personnel and the environment.
Environmental protection governance and waste treatment
The wastewater, waste gas and waste residue generated during the production process need to be properly treated. For instance, wastewater can be discharged up to standard through biochemical treatment, membrane separation and other technologies. Waste gas can be purified and treated through methods such as adsorption and catalytic combustion. Waste residue can be entrusted to qualified units for safe disposal.
adverse reaction
4,6-Dimethyldibenzothiophene (CAS number: 1207-12-1) is a sulfur-containing organic compound with the molecular formula C ₁₄ H ₂ S and a molecular weight of 212.31 g/mol. Its appearance is a white to light yellow crystalline solid, with a melting point of 153-157 ° C, a boiling point of about 312 ° C, and a density of 1.14-1.18 g/cm ³. This substance has been widely studied as a sulfur-containing compound model in the petroleum industry. Due to the spatial shielding effect of its two methyl substituents on sulfur atoms, it is difficult to remove it through conventional hydrogenation desulfurization processes, making it a challenging substance in the field of petroleum desulfurization.
Adverse reactions under acute exposure
Oral toxicity
Animal experiments have shown that the acute oral toxicity of 4,6-dimethyldibenzothiophene is relatively low
Rat model: The LD of a single oral administration is 2000 mg/kg, which belongs to low toxicity substances.
Symptom presentation: The high-dose group (≥ 1000 mg/kg) showed reduced activity and shortness of breath, which recovered within 24 hours without any deaths.
Mechanism speculation: The interaction between sulfur atoms and digestive mucosa may trigger mild inflammation, but methyl substituents reduce its reactivity.
Inhalation exposure
At present, there is no direct inhalation toxicity study on 4,6-dimethyldibenzothiophene dust or vapor, but reference can be made to similar sulfur-containing compound data:
Model prediction: Based on molecular weight and volatility, its vapor pressure is extremely low (about 0.0001 mmHg at 25 ° C), and the inhalation risk mainly comes from dust.
Analogical study: Exposure to dust from dibenzothiophene (DBT) can lead to pulmonary alveolar proteinosis in rats, but 4,6-dimethyldibenzothiophene may reduce the pulmonary alveolar deposition rate due to methyl substitution.
Skin eye contact
Skin irritation: Patch tests showed that a 0.1% concentration solution did not cause erythema or edema on rabbit skin, but long-term exposure may lead to mechanical damage due to crystal friction.
Eye irritation: After splashing into the eyes, 0.5% solution caused mild conjunctival congestion in rabbit eye experiments, which subsided within 24 hours without corneal damage.
Frequently Asked Questions
What is 4,6-DMDBT?
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4,6-Dimethyldibenzothiophene is an organic sulfide with the chemical formula C₁₄H₁₂S and a molecular weight of 212.31 g/mol. It is a methyl derivative of dibenzothiophene (DBT), featuring two methyl groups (at positions 4 and 6) in its structure. These groups protect the central sulfur atom through steric hindrance, making it difficult to remove via desulfurization reactions.
What are the specific applications of 4,6-DMDBT in the petroleum industry?
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Model Compound: Used to simulate hard-to-desulfurize sulfides in petroleum, evaluating the performance of hydrodesulfurization catalysts.
Research Focus: Exploring the desulfurization efficiency of novel catalysts (such as molecular sieves and metal phosphides) toward 4,6-DMDBT to optimize petroleum refining processes and reduce sulfur emissions.
What are the environmental impacts of 4,6-DMDBT?
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Environmental Persistence:
Due to its chemical stability, 4,6-DMDBT is difficult to degrade in the environment. It may enter water bodies and soil through fuel combustion or industrial emissions, posing potential risks to ecosystems.
Significance in Desulfurization Research:
Studying its removal methods helps reduce sulfur content in petroleum products and lower sulfur dioxide emissions during combustion, thereby mitigating air pollution and acid rain issues.
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