Name | Catechol |
Synonyms | Catechol C.I. 76500 Pyrocatechol ai3-03995[qr] 1,2-Benzenediol 2-Hydroxyphenol benzene-1,2-diol 2-hydroxyphenol[qr] 1,2-benzenediol[qr] Benzene, o-dihydroxy- C.I. Oxidation Base 26 benzene,1,2-dihydroxy- 1,2-dihydroxybenzene[qr] 1,2-Benzenediol (pyrocatechol) |
CAS | 120-80-9 |
EINECS | 204-427-5 |
InChI | InChI=1/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H |
Molecular Formula | C6H6O2 |
Molar Mass | 110.11 |
Density | 1,371 g/cm3 |
Melting Point | 100-103 °C (lit.) |
Boling Point | 245 °C (lit.) |
Flash Point | 279°F |
Water Solubility | 430 g/L (20 ºC) |
Solubility | 430g/l |
Vapor Presure | 1 mm Hg ( 75 °C) |
Vapor Density | 3.8 (vs air) |
Appearance | Crystalline Flakes |
Color | white to faintly beige |
Exposure Limit | TLV-TWA 5 ppm (~22 mg/m3) (ACGIH). . |
Merck | 14,7999 |
BRN | 471401 |
pKa | 9.85(at 20℃) |
PH | 6 (100g/l, H2O, 20℃) |
Storage Condition | Store below +30°C. |
Stability | Stable. Substances to be avoided include acid chlorides, acid anhydrides, bases, oxidizing agents, nitric acid. Light sensitive; may discolour on exposure to air. Combustible. |
Sensitive | Air & Light Sensitive |
Explosive Limit | 1.97%(V) |
Refractive Index | 1.6120 (estimate) |
Physical and Chemical Properties | Character: colorless crystals. Discoloration in air and light. Its solution in the air into a tan, see light or open air discoloration, can sublimate. soluble in 2.3 times water, soluble in ethanol, ether, benzene, chloroform, soluble in pyridine and caustic liquid. |
Use | Is an important chemical intermediate, can be used as rubber hardening agent, electroplating additives, skin antiseptic, hair dye, photo developer, color photo antioxidant |
Hazard Symbols | Xn - Harmful |
Risk Codes | R21/22 - Harmful in contact with skin and if swallowed. R36/38 - Irritating to eyes and skin. R68 - Possible risk of irreversible effects R43 - May cause sensitization by skin contact |
Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37 - Wear suitable gloves. S39 - Wear eye / face protection. |
UN IDs | UN 2811 6.1/PG 3 |
WGK Germany | 2 |
RTECS | UX1050000 |
TSCA | Yes |
HS Code | 2907 29 00 |
Hazard Class | 6.1 |
Packing Group | III |
Toxicity | LD50 in mice (mg/kg): 260 orally; 190 i.p. (Lehman) |
Downstream Products | 3-Ethoxy-4-hydroxybenzaldehyde |
colorless crystals. Discoloration in air and light. The solution turned tan in air. Flammable. The relative density was 1. 37. The melting point of 1 05 deg C (104~1 05 deg C). Boiling point 246 °c (look kPa). Flash point (Open Cup) 127 °c. Can sublimate. Ignition point (in a closed kettle) 127 °c. Soluble in 2.3 times water, soluble in ethanol, ether, benzene, chloroform, soluble in pyridine and caustic liquid.
prepared by hydrolysis of O-chlorophenol in alkaline medium.
An important pharmaceutical intermediate for the preparation of berberine (berberine) and isoproterenol. Can also be prepared spices (piperonal), dyes, photosensitive materials, electroplating materials, special inks, antioxidants, light stabilizers, preservatives and accelerators.
LogP | 0.93 |
(IARC) carcinogen classification | 2B (vol. 15, Sup 7, 71) 1999 |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
use | is an important chemical intermediate, which can be used to make rubber hardener, electroplating additive, skin antiseptic fungicide, hair dye, photographic developer, etc. used as analytical reagent catechol is an intermediate of fungicide ethamarb, insecticide propoxel and carbofuran. As an important pharmaceutical intermediate, it is used to make berberine and isoproterenol. It can also be used to produce 4-tert-butylcatechol as a polymerization inhibitor for styrene, butadiene and vinyl chloride. Or used in the manufacture of antioxidants, developers, fungicides, rubber additives, electroplating additives, special inks, light stabilizers, dyes, spices, etc. is an important pharmaceutical intermediate, which can be used to make cough, eugenol, berberine and isoprenaline. It is an important chemical intermediate, which can be used as rubber hardener, electroplating additive, skin antiseptic, hair dye, photographic developer, color antioxidant, etc. It is used for photography, dyes, antioxidants, light stabilizers, and is an important pharmaceutical intermediate Color reaction or colorimetric analysis to determine titanium, molybdenum, tungsten, vanadium, iron and cerium. |
Production method | Catechol mostly exists in nature in the form of derivatives. For example, o-methoxyphenol and 2-methoxy-4-methylphenol are important for beech creosote oils. Catechol was first obtained by distilling protocatechuic acid or distilling catechu extract: it was later discovered that catechol can also be obtained by dry distillation of certain plants or alkali melting of certain resins. In industry, in the past, it was generally extracted from tar by low-temperature dry distillation of coal. There are many processes for the synthesis of catechol. (1) Using phenol as raw material, it is obtained by chlorination of chlorine, hydrolysis of copper sulfate and sodium hydroxide, and acidification of hydrochloric acid. (2) Direct oxidation by benzene or phenol and hydrogen peroxide. The direct oxidation of phenol with hydrogen peroxide to produce catechol includes Ube Kechang Company of Japan and Rhone-Planck Company of France. (3) It is prepared by pressure hydrolysis of o-chlorophenol in alkaline medium. its preparation methods are as follows: 2,4-disulfophenol alkali fusion hydrolysis method; o-chlorophenol hydrolysis method; phenol direct oxidation method; phenol oxidation method; o-hydroxycyclohexanone dehydroaromatization method. Among them, (1) and (2) processes are complicated, and the three wastes are polluted more, which are gradually replaced by new processes, while methods (4) and methods (5) are undergoing industrial tests abroad. The direct oxidation of phenol uses hydrogen peroxide as the oxidant, and the hydroxylation reaction occurs directly at the o-and para-positions of phenol in the presence of a catalyst. After entering the 2070s, this method has achieved great success. France's Rhône-Planck Company built a set of 10800t/a catechol and 7200t/a hydroquinone industrial plant in 1973, and Japan's Yuduxing Industrial Company also built a set of 600t/a catechol plant. Direct oxidation has become the simplest method to produce catechol. Methyl isobutyl ketone is used as extractant for extraction and separation of o-hydroquinone and unreacted phenol. The process is directly oxidized by phenol and hydrogen peroxide. This method has been industrialized abroad and in China in recent years. Phenol and methyl ethyl ketone, 60% H2O2, activated clay VH and 85% H3PO4 were added into the reactor, stirred at 100 ℃ for 30min, and phenol was converted into catechol and hydroquinone. |
category | pesticide |
toxicity classification | highly toxic |
acute toxicity | oral-rat LD50: 260 mg/kg; Oral-mouse LD50: 260 mg/kg |
Explosive hazard characteristics | Severe reaction with oxidant |
flammability hazard characteristics | when heated, open flames are combustible; burning produces stimulating smoke |
storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants and food additives |
fire extinguishing agent | mist water, carbon dioxide, sand |
occupational standard | TWA 20 mg/m3 |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |