Knowledge of o-phenylphenol
About Sodium cyanoborohydride
15 10 月, 2021Sodium bromide
17 11 月, 2021Knowledge of o-phenylphenol
Ortho-phenylphenol, also known as 2-hydroxyphenyl or 2-phenyl phenol, is a white or light yellow or light red powder, flake or block with a weak phenolic taste. The melting point is 55.5~57.5℃, the boiling point is 283~286℃ (0.1MPa), the relative density is 1.213 (20℃), and the flashpoint is 123.9℃. Slightly soluble in water, easily soluble in organic solvents such as methanol, acetone, benzene, xylene, trichloroethylene, and dichlorobenzene. Sodium o-phenyl phenol is referred to as SOPP, which is white flakes or lumps or light red powder, which is easily soluble in water.
The role of Ortho-phenylphenol
Used as a carrier for hydrophobic synthetic fibers such as chlorinated fiber and polyester in the carrier dyeing method, surfactants, bactericidal preservatives, and dye intermediates.
Ortho-phenylphenol is an organic chemical product with a very wide range of uses. It is widely used in the fields of sterilization and corrosion protection, printing and dyeing auxiliaries and surfactants, as well as stabilizers and flame retardants for the synthesis of new plastics, resins, and polymer materials. Its specific uses are as follows :
Antiseptic and antiseptic
O-Phenylphenol and its sodium salt have high weed-killing activity, broad-spectrum sterilization, and mildew removal ability, low toxicity and tastelessness, and are good preservatives. They can be used for anti-mildew and fresh-keeping of fruits and vegetables, especially suitable for citrus. It can also be used to treat lemons, pineapples, melons, fruits, pears, peaches, tomatoes, cucumbers, etc., to minimize rot. Countries such as the United Kingdom, the United States, and Canada are allowed to use a wider range of fruits, including apples.
Ortho-phenylphenol and its sodium salt can be used as preservatives and fungicides in cosmetics, wood, leather, fiber, and paper, etc. The general use concentration is 0.15-1.5%. The U.S. Environmental Protection Agency (EPA) allows the use of nearly two hundred varieties of antiseptic soaps, antiseptic and deodorant lotions, and antiseptic preservatives with o-phenyl phenol or its sodium salt as the main ingredient, and it is considered that these products are non-toxic Yes, the annual consumption of o-phenyl phenol in this field alone exceeds 1 million pounds.
Dyeing carrier for synthetic fibers
Ortho-phenylphenol and its water-soluble sodium salt can be used as a dye carrier for polyester fibers, and can also be used as a carrier when dyeing hydrophobic synthetic fibers such as chlorinated fiber and polyester.
Synthesize new phosphorus-containing flame-retardant materials
When the polymer material containing organic phosphorus compounds is burned, a graphite-like carbonized film will be formed on the surface of the material to isolate the polymer from the air. It has good flame-retardant properties, high flame-retardant efficiency, low volatility, oil and hydrolysis resistance It has good performance and is more and more widely used, and will gradually replace the inorganic and halogen-containing flame-retardant materials used today. Using o-phenyl phenol as a raw material, a new type of phosphorus-containing flame-retardant intermediate DOPO can be synthesized, mainly for the following applications:
(1) Synthetic flame-retardant polyester
DOPO is a raw material that reacts with itaconic acid to produce intermediate ODOP-BDA, which can partially replace ethylene glycol to obtain a new type of phosphorus-containing flame-retardant polyester. Studies have shown that when the phosphorus content in PET and PEN reaches 0.75% and 0.5%, respectively, polyester exhibits a good flame retardant effect. In 2012, the world's annual production of polyester has reached more than 30 million tons. If 5% of it is phosphorus-containing flame-retardant polyester, more than 50,000 t/a of o-phenyl phenol is required.
(2) Synthetic flame-retardant epoxy resin
Epoxy resin has excellent bonding properties, electrical insulation properties, and other advantages. It is widely used in adhesives, electronic instruments, aerospace, coatings, and advanced composite materials. In 2004, the consumption of epoxy resin in the world reached more than 200,000 tons. /year. DOPO reacts with benzoquinone to form ODOPB, which partially replaces bisphenol A and forms a new flame-retardant epoxy resin. Studies have shown that the newly synthesized phosphorus-containing flame-retardant epoxy resin has a better flame-retardant effect than the Br flame-retardant epoxy resin containing 17.26% when the P content is 2.1% and does not produce smoke, and the thermal stability is also excellent. For epoxy resin without flame retardant.
(3) Improve the organic solubility of polymers
Using DOPO as raw material, the synthesis of 2DOPO-A partially replaces the synthetic polyamide monomer DABP. The resulting new polyamide is soluble in solvents such as NMP, DMAc, DMF, and DMSO. At the same time, it has thermal stability and resistance at high temperatures. The flammability is also significantly improved.
(4) As an intermediate in the synthesis of antioxidants
The Taiwan patent reported the use of DOPO to synthesize phosphorus-containing antioxidants, antioxidants for unsaturated polyesters, phenols, and greases, and Formosa Plastics Group for copper-based sheets for computers, and it has good thermal stability.
(5) Stabilizer for synthetic polymer materials
The Japanese patent reported the stabilizer of polymer materials synthesized by DOPO. Adding this compound during the processing of polyethylene, polypropylene, and polyvinyl chloride can improve the stability of polymer compounds during thermal processing.
(6) Synthetic luminescent matrix
Organic light-emitting diodes are important optoelectronic materials. Sun et al. used DOPO derivatives as monomers to synthesize polymers with light-emitting properties. DOPO derivatives act as emission groups and can emit blue light with a wavelength of 325-350nm, which can be applied to organic light-emitting diodes.
As a monomer for the synthesis of new polymers
Phenolic resin has the advantages of high mechanical strength, good electrical insulation performance, excellent heat resistance, and flame retardancy. It is widely used in the preparation of glass fiber reinforced plastics, molding compounds, coatings, adhesives, etc. However, phenolic resins also have disadvantages, such as heat resistance. Poor performance, etc. Replace phenol with o-phenyl phenol to synthesize a new phenolic resin. This resin has high thermal stability and low water absorption and can be used to prepare paints with excellent water and alkali stability.
Ortho-phenylphenol and its water-soluble sodium salt can be used as a dye carrier for polyester fibers, and can also be used as a carrier when dyeing hydrophobic synthetic fibers such as chlorinated fiber and polyester.
Synthesize new phosphorus-containing flame-retardant materials
When the polymer material containing organic phosphorus compounds is burned, a graphite-like carbonized film will be formed on the surface of the material to isolate the polymer from the air. It has good flame-retardant properties, high flame-retardant efficiency, low volatility, oil and hydrolysis resistance It has good performance and is more and more widely used, and will gradually replace the inorganic and halogen-containing flame-retardant materials used today. Using o-phenyl phenol as a raw material, a new type of phosphorus-containing flame-retardant intermediate DOPO can be synthesized, mainly for the following applications:
(1) Synthetic flame-retardant polyester
DOPO is a raw material that reacts with itaconic acid to produce intermediate ODOP-BDA, which can partially replace ethylene glycol to obtain a new type of phosphorus-containing flame-retardant polyester. Studies have shown that when the phosphorus content in PET and PEN reaches 0.75% and 0.5%, respectively, polyester exhibits a good flame retardant effect. In 2012, the world's annual production of polyester has reached more than 30 million tons. If 5% of it is phosphorus-containing flame-retardant polyester, more than 50,000 t/a of o-phenyl phenol is required.
(2) Synthetic flame-retardant epoxy resin
Epoxy resin has excellent bonding properties, electrical insulation properties, and other advantages. It is widely used in adhesives, electronic instruments, aerospace, coatings, and advanced composite materials. In 2004, the consumption of epoxy resin in the world reached more than 200,000 tons. /year. DOPO reacts with benzoquinone to form ODOPB, which partially replaces bisphenol A and forms a new flame-retardant epoxy resin. Studies have shown that the newly synthesized phosphorus-containing flame-retardant epoxy resin has a better flame-retardant effect than the Br flame-retardant epoxy resin containing 17.26% when the P content is 2.1% and does not produce smoke, and the thermal stability is also excellent. For epoxy resin without flame retardant.
(3) Improve the organic solubility of polymers
Using DOPO as raw material, the synthesis of 2DOPO-A partially replaces the synthetic polyamide monomer DABP. The resulting new polyamide is soluble in solvents such as NMP, DMAc, DMF, and DMSO. At the same time, it has thermal stability and resistance at high temperatures. The flammability is also significantly improved.
(4) As an intermediate in the synthesis of antioxidants
The Taiwan patent reported the use of DOPO to synthesize phosphorus-containing antioxidants, antioxidants for unsaturated polyesters, phenols, and greases, and Formosa Plastics Group for copper-based sheets for computers, and it has good thermal stability.
(5) Stabilizer for synthetic polymer materials
The Japanese patent reported the stabilizer of polymer materials synthesized by DOPO. Adding this compound during the processing of polyethylene, polypropylene, and polyvinyl chloride can improve the stability of polymer compounds during thermal processing.
(6) Synthetic luminescent matrix
Organic light-emitting diodes are important optoelectronic materials. Sun et al. used DOPO derivatives as monomers to synthesize polymers with light-emitting properties. DOPO derivatives act as emission groups and can emit blue light with a wavelength of 325-350nm, which can be applied to organic light-emitting diodes.
As a monomer for the synthesis of new polymers
Phenolic resin has the advantages of high mechanical strength, good electrical insulation performance, excellent heat resistance, and flame retardancy. It is widely used in the preparation of glass fiber reinforced plastics, molding compounds, coatings, adhesives, etc. However, phenolic resins also have disadvantages, such as heat resistance. Poor performance, etc. Replace phenol with o-phenyl phenol to synthesize a new phenolic resin. This resin has high thermal stability and low water absorption and can be used to prepare paints with excellent water and alkali stability.
Ortho-phenylphenol production method
It can be recovered from the distillation residue of phenol produced by the sulfonation method. The distillation residue of phenol contains about 40% phenyl phenol, and the other components are phenol, inorganic salts, water, etc. After vacuum distillation, the mixed-position phenyl phenol fraction is separated, the vacuum degree is 53.3-66.7kPa, and the temperature is 65-75℃ and cut to above 100℃, but not more than 1345℃. The difference in solubility of ortho- and para-hydroxyphenyl in trichloroethylene is used to separate the two into pure products. The mixed position (mainly 2-hydroxyphenyl and 4-hydroxyphenyl) is heated and dissolved in trichloroethylene. After cooling, 4-hydroxyphenyl crystals are first precipitated, and 4-hydroxyphenyl is obtained by centrifugal filtration and drying. . The mother liquor is washed with sodium carbonate solution, and dilute lye is added to make 2-hydroxyphenyl salt. After standing for stratification, take the upper layer of 2-hydroxyphenyl sodium salt to dehydrate under reduced pressure to obtain the finished sodium salt. The sodium salt of 2-hydroxyphenyl is white to light red powder. Easily soluble in water, 122g can be dissolved in 100g of water, and the pH of a 2% aqueous solution is 11.1-12.2. It is also easily soluble in acetone and methanol, soluble in glycerin, but insoluble in fats. The 2-Hydroxybiphenyl sodium salt is acidified to produce 2-hydroxyphenyl, both of which are food additives.
It is obtained by heating dibenzofuran and sodium metal to about 200°C, and the product is decomposed by acid.
It is obtained by hydrolysis of 2-aminobiphenyl after diazotization.