Resorcinol Resorcinol
Structural formula
| Business number | 02X8 |
|---|---|
| Molecular formula | C6H6O2 |
| Molecular weight | 110.11 |
| label |
1,3-dihydroxybenzene, Raysulfonate, 1,3-Benzodiphenol, Reisosin, m-dihydroxybenzene, resin phenol, 1,3-Dihydroxybenzene (Resorcinol), 3-Hydroxycyclohexadien-1-One, Alpha-Resorcinol, Resorcinol, 1,3-Benzenediol, m-Dihydroxybenzene, Pesticide intermediates; phenols, aromatic alcohols and their derivatives |
Numbering system
CAS number:108-46-3
MDL number:MFCD00002269
EINECS number:203-585-2
RTECS number:VG9625000
BRN number:906905
PubChem number:24899381
Physical property data
1. Characteristics: White needle-like crystals with an unpleasant odor and gradually turn red when placed in the air. [1]
2. pH value: 5.2[2]
3. Melting point (℃): 110.7[3]
4. Boiling point (℃): 276.5[4]
5. Relative density (water=1): 1.27[5]
6. Relative vapor density (air=1): 3.79[6]
7. Saturation Vapor pressure (kPa): 0.13 (108.4℃)[7]
8. Heat of combustion (kJ/mol): -2847.8[8]
9. Critical pressure (MPa): 7.49[9]
10. Octanol/water partition coefficient: 0.8[10]
11. Flash point (℃): 127 (CC) [11]
12. Ignition temperature (℃): 608[12]
13. Explosion upper limit (%): 9.8[13]
14. Explosion lower limit (%): 1.4[14]
15. Solubility: Easily soluble in water, ethanol, ether, slightly soluble in chloroform. [15]
16. Relative density (20℃, 4℃): 1.165131
17. Relative density ( 25℃, 4℃): 1.110184
18. Crystal phase standard combustion heat (enthalpy) (kJ·mol-1): – 2850.6
19. Crystal phase standard claim heat (enthalpy) (kJ·mol-1): -368.0
20. Gas phase standard entropy (J· mol-1·K-1): 344.51
21. Gas phase standard formation free energy (kJ·mol-1): -189.1
22. Gas phase standard hot melt (J·mol-1·K-1): 123.75
23. Gas phase standard combustion heat (enthalpy) (kJ·mol-1): -2943.9
24. Gas phase standard claimed heat (enthalpy) (kJ·mol-1):-274.7
Toxicological data
1. Acute toxicity[16] LD50: 301mg/kg (rat oral); 3360mg/kg (rabbit dermal )
2. Irritation[17]
The operation steps are: add benzene, 60% fuming sulfuric acid and sodium sulfate into the reaction pot, control the reaction temperature to 75°C, and the resulting sulfonate contains 75% benzenesulfonic acid, 1% diphenyl sulfone, and 20% sulfuric acid. , 4% sodium sulfate. Then add anhydrous sodium sulfate, stir and heat to 175°C, add sulfur trioxide and react for 1.5 hours. The resulting product consists of 75% benzene disulfonic acid, 4% diphenyl sulfone disulfide, and 17% sulfuric acid. , 4% sodium sulfate. After neutralization with dilute alkali and removal of excess sulfate, the benzene disulfonic acid sodium salt is obtained. Add it to molten sodium hydroxide at 290°C and raise the temperature to 325°C within 15 minutes. Dissolve the alkali soluble material into water, acidified with sulfuric acid, and then extracted with ether or butanol. The crude product is obtained after the extract is distilled to recover the solvent. The crude product is distilled under reduced pressure and the 178°C fraction is collected to obtain the Resorcinol.
3. m-dicumyl oxidation method (HOP method): m-dicumyl oxidation method is a method similar to the oxidation of cumene to produce phenol and acetone. Benzene and propylene are in The alkylation reaction is carried out under the action of a catalyst to generate m-dicumylbenzene. m-dicumylbenzene is oxidized under 80-90°C and weakly alkaline conditions by introducing oxygen and air to generate dihydroperoxym-dicumyl and m-dicumyl. The by-product m-dicumyl hydroxyperoxide is crystallized and filtered to separate m-dicumyl dihydroperoxide, and then dissociated with sulfuric acid or phosphoric acid at 80°C to obtain resorcinol and acetone. As environmental protection requirements become increasingly stringent, this method will become the development direction for industrial synthesis of resorcinol.
Purpose
1. Resorcinol is mainly used in rubber adhesives, synthetic resins, dyes, preservatives, pharmaceuticals and analytical reagents. Resorcinol is similar to phenol and cresol and forms a condensation polymer with formaldehyde. It can be used to make tire cord adhesives for viscose yarn and nylon, to prepare wood adhesives, and to bond vinyl materials and metals. Resorcinol is an intermediate for many azo dyes and fur dyes. Raw material of pharmaceutical intermediate p-nitrogen-based salicylic acid. Resorcinol has a bactericidal effect and can be used as a preservative and added to cosmetics and dermatological pastes and ointments. The derivative of resorcin, β-methylumbelliferone, is an intermediate of optical bleach, trinitroresorcin is a detonator, and a considerable amount of resorcin is used to produce benzophenone. UV absorber. This product can irritate the skin and mucous membranes and can be rapidly absorbed through the skin, causing poisoning symptoms. The minimum lethal dose for subcutaneous injection in rats is 450mg/kg.
2. Used for the determination of nitrite and nitrate. Colorimetric methods can be used to detect zinc, lead, furandehyde, sugars and ketones in the presence of ammonia. Also used in organic synthesis and pharmaceutical industry.
3. Used as an accelerator for epoxy resin curing and a UV absorber for synthetic resins, adhesives, dyes, and medicines (para-aminosalicylic acid). Also used in the synthesis of resorcinol-formaldehyde resin adhesives. Resorcinol is an important organic chemical product and synthetic intermediate. In tires, hoses and tapes, resorcinol-formaldehyde tree (RF resin) is used to impregnate rayon and polyamide fiber cords to increase the number of cords. Bonding between wire and rubber. Treating steel cords with resorcin-triaryl cyanurate-formaldehyde resin can improve the bonding properties of steel wires to rubber. Adding resorcinol, hexamethylenetetramine and silica to rubber compounds can improve the reinforcing effect of short fibers in the rubber matrix. Bis(diphenylphosphonate)resorcin ester synthesized from resorcinol is a non-halogen flame retardant with high thermal stability and is suitable for modified polyether, polycarbonate, ABS resin and various thermoplastic resins and polyurethane and other plastics. Resorcin also has a certain bactericidal effect.
4. Used in the manufacture of a variety of organic drugs and dyes, and is an intermediate for fur dyes. In medicine, it is used externally to treat skin diseases such as eczema and psoriasis. In the cosmetics industry, used in hair dye formulations (as compound dyes). Resorcinol has a bactericidal effect and can be used as a preservative and added to cosmetics and dermatological pastes and ointments.
5. Used in medicine, dyes, rubber, plastics, photosensitive materials, chemical fibers, and explosives industries, such as synthetic aminosalicylic acid, dye eosin, benzophenone UV absorbers, etc., and also used in Preparation of tire cord dipping, foaming agent solution of urea-formaldehyde resin, pharmaceutical additives for anti-acne cosmetics, bactericides in hair restorers, etc.
6. Used in making dyes, plastics, drugs, synthetic fibers, etc. [28]
