Resorcinol (or resorcin) is a dihydroxy benzene. It is the 1,3-isomer of benzenediol with the formula C6H4(OH)2. The key component of an adhesive system used in producing tyres and other mechanical items made of rubber reinforced with fibers is resorcinol. Resorcinol-formaldehyde resin-based adhesives or phenol-modified resorcinol-formaldehyde resin-based adhesives meet the requirements for room-temperature curing, structural integrity, and waterproof properties in wood bonding applications. In producing specialized chemicals, such as light screening agents that shield polymers from UV radiation, resorcinol is a crucial chemical intermediary. Resorcinol is used to produce agricultural chemicals, flame retardants, dyestuffs, antioxidants, urethane elastomer chain extenders, explosive primers, and treatments to increase the mechanical and chemical resilience of textiles used in paper machines.
An overview of resorcinol
The structure of the dihydroxybenzene molecule has three isomeric compounds, each with a traditional name. Catechol is the ortho (1,2) isomer that forms clear crystals and is used as a starting material to synthesize synthetic catecholamines, which have important physiological effects as neurotransmitters and hormones (epinephrine, adrenaline, dopamine, and norepinephrine). It is also known by the names catechin, pyrocatechol, and pyrocatechuic acid. The resorcinol, or resorcin, is the meta (1,3) isomer that crystallizes into transparent needles that are utilized to make diazo dyes and plasticizers. It is made by combining fuming sulfuric acid with benzene to sulfonate it, then adding caustic soda to the resultant benzene sulfonic acid.
Resorcinol is a UV absorber found in resins. It is employed in the production of adhesives and fluorescent and leather dyes. Resorcinol formaldehyde resins, which are used to manufacture nylon and rayon, are produced by reacting with formaldehyde. As a pharmaceutical, it is used in conjunction with sulfur and other acne therapies to treat oily skin problems and acne. It is a component of shampoo and sunscreen cosmetics that fights dandruff. In addition, it serves as a chemical intermediary in the manufacture of various organic molecules and medications. Hydroquinone, also referred to as quinol, is the para (1,4) isomer that produces transparent prisms that are employed as a developer and reducer in photography (apart from color film). It is created when benzoquinone is chemically reduced in high amounts. This substance functions as an antioxidant, stabilizer, inhibitor, and intermediary in general. Hydroquinone is widely used as an intermediary in the synthesis of several compounds used in agriculture, dyes, stabilizers, inhibitors, and antioxidants. UV absorbers in resins are made of resorcinol and its derivatives. They are employed in the production of adhesives (resorcinol formaldehyde resins) and fluorescent and leather dyes. As medicines, they are used in conjunction with sulfur and other acne therapies to treat oily skin problems and acne. They are a component of shampoo and sunscreen cosmetics that prevent dandruff.
Production of resorcinol
The production process involves either melting a variety of resins, such as galbanum, asafoetida, etc., with potassium hydroxide or distilling Brazilwood extract. It may be made synthetically by melting phenol-3-sulfonic acid, benzene-1,3-sulfonic acid, or 3-iodophenol with potassium carbonate; it can also be made by nitrous acid reacting with 3-aminophenol or 1,3-diaminobenzene. When potassium hydroxide is fused with several ortho- and para-compounds from the aromatic family, such as the bromophenols and benzene-para-sulfonic acid, resorcinol is also produced.
The synthesis of resorcinol involves sulfonating benzene in a way that encourages disubstitution in the meta position, then fusing it with anhydrous caustic. Resorcinol is the end product, which is refined under controlled circumstances to provide a technical-grade product that is usually 99.8 percent pure. For industries like medicines and cosmetics where ultra-high purity is necessary, INDSPEC also provides a U.S.P. grade of resorcinol that complies with US Pharmacopoeia.
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Environmental fate and exposure potential
Resorcinol may be released into the environment through a variety of waste streams as a result of its manufacture and usage in the rubber industry, tanning, and the production of resins, resin adhesives, chemical intermediates, and colors. Resorcinol can only exist as a vapor in the surrounding environment if it is discharged into the air, as indicated by its vapor pressure of 4.9X10-4 mm Hg at 25 degrees Celsius. The half-life of the reaction between vapor-phase resorcinol and photochemically generated hydroxyl radicals in the environment is predicted to be 1.9 hours. Although the rate of this reaction is unknown, the vapor-phase reaction of resorcinol with nitrate radicals may also be a significant atmospheric removal mechanism in metropolitan areas at night. Resorcinol is anticipated to have a high mobility when released into soil. A Henry’s Law constant of 9.9X10-11 atm-cu m/mole is used to indicate that volatilization from damp soil surfaces is not likely to be a significant fate process.
An essential environmental destiny mechanism for resorcinol is anticipated to be biodegradation. In an aerobic screening test, resorcinol’s half-life varied from 0.16 to 0.24 days using activated sludge. In contrast, complete degradation of resorcinol happened in 8 days (as indicated by a 100% UV absorbancy loss) in a mineral salt medium utilizing a silt loam soil inocula. Presumably, resorcinol’s predicted Koc will prevent it from attaching to silt and suspended particles if it is discharged into water. Based on the anticipated Henry’s Law constant of this molecule, volatilization from water surfaces is not considered to be a significant fate process. A BCF value of 2 indicates that there is little chance of bioconcentration in aquatic creatures. Due to a deficiency of hydrolyzable functional groups, hydrolysis is not anticipated to constitute a significant environmental destiny process. Resorcinol exposure at work can happen through skin contact at locations where the substance is generated or used as a chemical intermediary in the production of other compounds. The usage of consumer goods like some hair dyes that can contain this ingredient could expose the general public.
Applications of resorcinol
Resorcinol is a UV absorber found in resins. Resorcinol formaldehyde resins, which are used to make fluorescent and leather dyes and adhesives, are made with it. As a pharmaceutical, it is used in conjunction with sulfur and other acne therapies to treat oily skin problems and acne. It is a component of shampoo and sunscreen cosmetics that fights dandruff. In addition, it serves as a chemical intermediary in the manufacture of various organic molecules and medications. One of the parent substances of topical keratolytic agents is résorcinol.
Medical applications
It is an antiseptic and disinfectant used topically, and it is used 5–10% in ointments to treat chronic skin conditions such as hidradenitis suppurativa, psoriasis, and sub-acute eczema. It can be found in concentrations of 2% or less in over-the-counter topical acne treatments and at greater concentrations in prescription therapies. For erythematous eczema, resorcinol solutions that are weak and watery (25 to 35 g/kg) work well to relieve itching. Spraying a 2% solution is effective in treating whooping cough and hay fever. 0.6 mL of the 2% solution has been administered intravenously for the latter ailment. It can be added to shampoo or sunscreen cosmetics as an anti-dandruff ingredient. Its analgesic and hemostatic properties have led to its use in the treatment of stomach ulcers at dosages ranging from 125 to 250 mg in tablet form. It is poisonous in high dosages, producing convulsions, perspiration, salivation, deafness, and giddiness. Additionally, it is incorporated into certain medicated soaps. The compound monoacetylresorcinol, C6H4(OH)(O-COCH3), is marketed as euresol. One of the active components of medications like Resinol, Vagisil, and Clearasil is resorcinol.
Chemical applications
Resorcinol is also used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. It is used in the production of diazo dyes and plasticizers and as a UV absorber in resins. An emerging use of resorcinol is as a template molecule in supramolecular chemistry. The -OH groups on resorcinol form hydrogen bonds to target molecules, holding them in the proper orientation for a reaction. Many such reactions can be carried out in the solid state, thereby reducing or eliminating the use of solvents that may be harmful to the environment. Resorcinol is an analytical reagent for the qualitative determination of ketoses (Seliwanoff’s test). Resorcinol is the starting material for resorcinarene molecules and the initiating explosive lead styphnate. Resorcinol reacts with formaldehyde to form a thermoset resin which can form the basis of an aerogel. Resorcinol reacts with formaldehyde to form a thermoset resin which can form the basis of an aerogel.
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