Diphenyl Carbonate CAS 102-09-0

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Diphenyl carbonate (DPC) white crystalline solid. It is insoluble in water and soluble in hot ethanol, benzene, ether, carbon tetrachloride, glacial acetic acid and other organic solvents. It can be decomposed by hot alkali. Diphenylcarbonat and impurities in production can cause skin allergy. Diphenylcarbonat is low toxic, but the raw materials used in the production process are highly toxic. Pay attention to prevent phosgene leakage in the production process. The production site should be well ventilated. Operators shall wear protective equipment. It is mainly used as synthetic raw materials of engineering plastics such as polycarbonate and poly (p-hydroxybenzoate), and also as plasticizer and solvent of nitrocellulose.

Diphenyl carbonate (DPC), as an important organic carbonate compound, has become an indispensable core raw material in modern chemical engineering, materials science, and pharmaceutical pesticide fields due to its unique chemical properties and wide industrial application value. Its molecular formula is C15H12O4, which appears as a white crystalline solid at room temperature. It is insoluble in water but easily soluble in organic solvents such as hot ethanol, benzene, and ether, and has low toxicity and biodegradable environmental characteristics.

It is a key monomer for synthesizing polycarbonate (PC), with applications covering high-end manufacturing fields such as electronics, automotive, and medical. Polycarbonate, as a high-performance engineering plastic, is known as a "transparent metal" due to its transparency, impact resistance, heat resistance, and electrical insulation properties.

 

1. Electronic and electrical field
Polycarbonate is used to manufacture components such as phone cases, laptop cases, LED lampshades, and connectors. For example, the middle frame and back cover of Apple's iPhone series are made of polycarbonate composite material, which ensures structural strength and achieves lightweight design.
2. Automotive industry field
Polycarbonate is widely used in automotive headlight lenses, instrument panels, fenders, and interior parts. Its high temperature resistance (long-term use temperature up to 130 ℃) can meet the requirements of engine compartment peripheral components, while its high light transmittance (over 90%) makes it an ideal material for headlight lenses.

 

3. Medical equipment field
Polycarbonate is used to manufacture infusion bottles, syringes, dialyzers, and surgical instrument casings. Its biocompatibility meets FDA standards and can be treated with steam sterilization to ensure medical safety.
4. Non phosgene process innovation: Traditional polycarbonate production relies on phosgene method, but phosgene is highly toxic and heavily polluting. In recent years, the non phosgene melt ester exchange method using diphenylcarbonat and bisphenol A as raw materials has become mainstream. This process has no wastewater discharge and the product purity reaches 99.9%, significantly improving environmental protection and economic benefits. The diphenylcarbonat slicing project invested and constructed by Sichuan Tianhua Chemical Group adopts this process, with an annual production capacity of 50000 tons, meeting the demand for high-end engineering plastics in China.

It is a core intermediate for synthesizing carbamate insecticides, and its derivatives have important value in the fields of agriculture and medicine.

 

1. Pesticide synthesis
Reacting with methylamine to produce methyl isocyanate, further synthesizing carbamate insecticides such as Carbofuran. Kebaibu can effectively control aphids, nematodes, and underground pests, and is widely used in crops such as corn and cotton. Although some countries have restricted its use due to toxicity issues, it still holds a significant market share in developing countries.
2. Pharmaceutical intermediates
Participate in the synthesis of compounds such as monoisocyanates and diisocyanates for the preparation of anti-inflammatory drugs, anti allergic drugs, and local anesthetics. For example, its derivative 4-isocyanatobenzoate is a key intermediate in the synthesis of nonsteroidal anti-inflammatory drugs.

 

Environmental substitution trend: With the strengthening of global control over highly toxic pesticides, the research and development of diphenylcarbonat based low toxicity pesticides has become a hot topic. For example, insect growth regulators such as Fenoxycarb synthesized from it have high efficiency and low residue characteristics, which meet the needs of green agriculture development.

With its excellent solubility and thermal stability, it plays an important role in the fields of plasticizers, solvents, and heat carriers.

 

1. Plasticizer
As a plasticizer for nitrocellulose, it can enhance its flexibility and cold resistance, and is widely used in coatings, inks, and adhesives. For example, adding diphenyl carbonate based plasticizers to automotive coatings can improve their scratch resistance and weather resistance.
2. Solvent and Heat Carrier
In chemical production, it is used as a high boiling point solvent (boiling point 302 ℃) to dissolve resins, waxes, and polymer materials. Meanwhile, its high specific heat capacity (1.8 J/g · K) makes it an ideal choice for heat transfer in high-temperature reaction systems.
Case: A chemical enterprise uses diphenylcarbonat instead of the traditional solvent dimethylformamide (DMF) to reduce volatile organic compounds (VOC) emissions by 40% in the production of polyurethane foam, while improving the heat resistance of the product.

Diphenylcarbonatexhibits unique value in the synthesis of new polymer materials, promoting the development of materials science towards high performance and functionalization.

 

Polyhydroxybenzoate (PHB)
Diphenylcarbonat reacts with p-hydroxybenzoic acid to form PHB, a biodegradable thermoplastic polyester. PHB is used to manufacture disposable tableware, packaging films, and medical sutures, with a degradation cycle of only 3-6 months, significantly reducing white pollution.
Aliphatic monoisocyanates
Catalytic decarboxylation of diphenylcarbonat to generate aliphatic monoisocyanates for the synthesis of waterborne polyurethane coatings. The VOC content of this coating is less than 50g/L, which meets the EU environmental standards and is widely used in the painting of building exterior walls and furniture.

 

Polyarylcarbonate
Polyarylcarbonate synthesized from diphenylcarbonat as raw material has radiation resistance and chemical corrosion resistance, and is used to manufacture nuclear power plant pipelines, chemical storage tanks, and aerospace components.
Technological breakthrough: The new titanium ester catalyst developed by the Institute of Process Engineering, Chinese Academy of Sciences has increased the yield of synthesizing poly (arylcarbonate) from diphenylcarbonat to 92%, reduced the reaction temperature by 50 ℃, and significantly reduced energy consumption.

The applications in the fields of coatings, inks, electronic materials, and environmental protection are constantly expanding.

 

1. Coatings and inks
Diphenylcarbonat is used as a crosslinking agent to enhance the hardness and wear resistance of UV cured coatings. Adding diphenylcarbonat based dispersants to ink can improve pigment dispersion and prevent printing clogging.
2. Electronic materials
The alignment film material used for manufacturing liquid crystal displays (LCDs) has high purity (≥ 99.9%), which can avoid the interference of impurities on the display effect.

 

Meanwhile, its derivative polycarbonate diol is a key raw material for synthesizing polyurethane elastomers, which are used to manufacture mobile phone vibration motors.

3. Environmental protection field
Diphenylcarbonat is used as a photocatalytic degradation agent to decompose organic pollutants in wastewater treatment. For example, it can efficiently degrade dye wastewater with a COD removal rate of 95% when combined with titanium dioxide composite materials.

There are three common methods for synthesizing diphenyl carbonate, and the specific explanations are as follows:

1. Phosgene method:

It is obtained by the reaction of phenol and phosgene. Add the dissolved phenol into 16-20% sodium hydroxide solution to prepare sodium phenol solution. Stir and cool down, start to inject phosgene at about 10 ℃, control the phosgenation reaction at 20-30 ℃, the reaction tail gas contains hydrogen chloride and phosgene that has not been reacted completely, lead it into the absorption tower, destroy it with dilute alkali solution, and then discharge it from high altitude. At the later stage of the reaction, take the reaction solution to test the pH, and stop using phosgene until it is neutral. Remove phosgene and hydrochloric acid gas from the pot, filter, wash with water, and melt and dehydrate under reduced pressure to obtain crude product. The crude product is distilled under reduced pressure, the narrow fraction is collected, and the liquid product is flaked by the flaker after condensation to obtain refined diphenylcarbonat. Polymerization grade products require high purity, and the melting point should be ≥ 78 ℃. Raw material consumption quota: phenol 963kg/t, sodium hydroxide (30%) 577kg/t, phosgene (≥ 98%) 592kg/t.

2. Transesterification:

The synthesis of diphenylcarbonat from phenol and dimethyl carbonate is usually carried out in two steps: the first step is to convert phenol into methylphenyl carbonate, and the second step is to further react with phenol to obtain diphenylcarbonat. The yield of this route is low, so it is necessary to develop efficient catalyst and improve the process flow.

3. Phenol oxidative carbonylation method:

Diphenylcarbonat was directly synthesized with phenol, carbon monoxide and oxygen in the presence of catalyst. This method is characterized by simple process, cheap raw materials and no pollution. But it has not been industrialized and is in the process of research and development.

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