Anthracene
Anthracene
CAS: 120-12-7
Molecular Formula: C14H10
Anthracene - Names and Identifiers
| Name | Anthracene |
| Synonyms | Anthracen Anthracene p-Naphthalene tetraoliven2g Paranaphtalene Crudeanthracene Anthracenepract Tetra Olive N2G anthracene, pure Sterilite hop defoliant Anthracene blue fluorescence Anthracenescintillationgrade |
| CAS | 120-12-7 |
| EINECS | 204-371-1 |
| InChI | InChI=1/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H |
Anthracene - Physico-chemical Properties
| Molecular Formula | C14H10 |
| Molar Mass | 178.23 |
| Density | 1.28 |
| Melting Point | 210-215 °C (lit.) |
| Boling Point | 340 °C (lit.) |
| Flash Point | 121 °C |
| Water Solubility | 0.045 mg/L (25 ºC) |
| Solubility | toluene: soluble20mg/mL, clear, colorless to faintly yellow |
| Vapor Presure | 1 mm Hg ( 145 °C) |
| Vapor Density | 6.15 (vs air) |
| Appearance | powder |
| Color | off-white to yellow |
| Exposure Limit | OSHA: TWA 0.2 mg/m3 |
| Merck | 14,682 |
| BRN | 1905429 |
| pKa | >15 (Christensen et al., 1975) |
| Storage Condition | 2-8°C |
| Explosive Limit | 0.6%(V) |
| Refractive Index | 1.5948 |
| Physical and Chemical Properties | The pure product is colorless prism-like crystals with blue-purple fluorescence. melting point 218 ℃ boiling point 340 ℃ relative density 1.25 refractive index 1.5948 flash point 121.11 ℃ solubility insoluble in water, slightly soluble in ethanol, soluble in ether, benzene, toluene, chloroform, acetone, carbon tetrachloride. |
| Use | For the manufacture of disperse dyes, alizarin, dye intermediates anthraquinone, can be used as raw materials for plastics, insulating materials |
Anthracene - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R67 - Vapors may cause drowsiness and dizziness R36 - Irritating to the eyes R11 - Highly Flammable R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R65 - Harmful: May cause lung damage if swallowed R38 - Irritating to the skin R66 - Repeated exposure may cause skin dryness or cracking R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S24/25 - Avoid contact with skin and eyes. S16 - Keep away from sources of ignition. S9 - Keep container in a well-ventilated place. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S36 - Wear suitable protective clothing. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | CA9350000 |
| TSCA | Yes |
| HS Code | 29029010 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: > 16000 mg/kg |
Anthracene - Upstream Downstream Industry
| Downstream Products | Carbazole Anthraquinone 9-Anthraldehyde |
Anthracene - Nature
Open Data Verified Data
colorless monoclinic plate-like crystals. There is light blue fluorescence, see light color darkening, can sublimate. 1g of the product is dissolved in 67ml of anhydrous ethanol, 70ml of methanol, 62ml of benzene, 85ml of chloroform, 200ml of ether, 31ml of carbon disulfide, 86ml of carbon tetrachloride, 125 ml of toluene. Flammable in case of open flame and high heat. A strong reaction with an oxidizing agent can occur.
Last Update：2024-01-02 23:10:35
Anthracene - Preparation Method
Open Data Verified Data
obtained in the last stage of distillation of coal tar.
Last Update：2022-01-01 09:27:10
Anthracene - Use
Open Data Verified Data
used in anthraquinone production, also used as pesticides, fungicides, gasoline inhibitors.
Last Update：2022-01-01 09:27:11
Anthracene - Safety
Open Data Verified Data
mice were injected intravenously with LD50:430mg/kg. The pure product is basically non-toxic. Industrial products because of containing impurities such as phenanthrene, carbazole, toxicity increased significantly. It is irritant to skin and mucous membrane; It is easy to cause photosensitivity dermatitis.
Last Update：2022-01-01 09:27:11
Anthracene - Reference Information
| color index | 10790 |
| Henry's Law Constant | 1.22 at 4 °C, 6.42 at 25 °C (dynamic equilibrium method, Bamford et al., 1999) |
| LogP | 4.65 at 20℃ |
| (IARC) carcinogen classification | 3 (Vol. 92, Sup 7) 2010 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| fused ring aromatic hydrocarbon | anthracene is a fused ring aromatic compound containing three rings, molecular formula C14H10. It occurs naturally in coal tar. The centers of the three rings of anthracene are on a straight line and are isomers of phenanthrene. Anthracene is a white flake crystal or light yellow needle crystal with light blue fluorescence. Melting point 216 ℃, boiling point 340 ℃, relative density 1.283(25/4 ℃); Easy to sublimate; Insoluble in water, insoluble in ethanol and ether, soluble in hot benzene. The chemical activity of the 9,10 positions in the anthracene molecule is relatively high, and it is oxidized with nitric acid to produce 9, 10-anthraquinone (see anthraquinone for the structural formula). Anthracene is an important intermediate for the synthesis of anthraquinone dyes and tannins; sodium and ethanol are used to reduce to generate 9,10-dihydroanthracene; addition of chlorine to generate 9,10-dichloroanthracene, which loses a molecule of hydrogen chloride when heated and becomes 9-chloranthracene; anthracene can also be used as a conjugated diene, and a Diels-Alder reaction occurs with maleic anhydride at the 9,10 position. In industry, crude anthracene is separated from anthracene oil fractions obtained from fractionating coal tar by crystallization method, and then purified by sublimation. High purity anthracene is used to produce single crystal anthracene and used in scintillation counters. Anthracene can also be used as insecticide, fungicide and gasoline coagulant. |
| anthraquinone | anthraquinone has long been used as a raw material for anthraquinone dyes and occupies an important position in the dye industry. Anthraquinone derivatives have been widely used in hydrogen peroxide production processes and in the pulp industry. anthraquinone is a fused ring organic compound with complex chemical structure, light yellow orthorhombic needle crystal, relative density 1.438 (4 ℃), melting point 286 ℃, boiling point 379.3 ℃, refractive index 1.438 (4 ℃), can be sublimated. Slightly soluble in water, ethanol, ether, chloroform, benzene, soluble in hot benzene, concentrated sulfuric acid, hot carbon tetrachloride. Stable, not easy to be oxidized, not easy to be reduced by weak reducing agents, not easy to be replaced by electrophilic groups, and can be heated and sulfonated with fuming sulfuric acid. Toxic, contact irritates the skin, can cause eczema, rhinitis and bronchial asthma. the preparation method of anthraquinone, in addition to the original anthracene oxidation method and phthalic anhydride (phthalic anhydride) Friedel-Crafts method, has recently reached the practical stage of naphthoquinone Diels-Alder method and styrene dimerization method. From anthraquinone can be derived into many intermediates (especially amino anthraquinone, hydroxyanthraquinone). These anthraquinone derivatives are used to synthesize vat dyes, acid dyes, reactive dyes and other advanced dyes. In addition, the anthracene hydroquinone produced by the hydrogenation of anthraquinone can be rapidly oxidized and reversed to anthraquinone in the air, and hydrogen peroxide is produced at the same time. Using the above principle, it is used in industry to manufacture hydrogen peroxide. In actual production, because a mixed solvent of solvent benzene and higher alcohols is used, the anthraquinone used is 2-ethylanthraquinone or 2-tert-butylanthraquinone with good solubility in this mixed solvent. Many intermediates derived from anthraquinone (especially amino anthraquinone, hydroxyanthraquinone, etc.) can synthesize urn dyes, acid dyes, reactive dyes and many other advanced dyes. Used in the production of hydrogen peroxide. Adding anthraquinone and tetrahydroanthraquinone in the pulp production process can improve the efficiency, so the use as a pulp additive is expanding. Reference material: Editor-in-Chief Wang Daquan. Dictionary of Fine Chemical Industry. Beijing: Chemical Industry Press. 1998. Page 128-129. |
| use | anthraquinone, an intermediate for the manufacture of disperse dyes, alizarin and vat dyes, can be used as raw materials for plastics and insulating materials this product is mainly used for the manufacture of dye intermediate anthraquinone and tannin. It can be used as insecticide, fungicide and gasoline anticoagulant. High purity anthracene is used to produce single crystal anthracene and used in scintillation counters. It is used to extract anthracene, phenanthrene and carbazole, and can also produce anthraquinone dyes, carbon black, synthetic tanning agents and various paints It is used as analytical reagent and scintillator, as well as the synthesis of dyes It is used for anthraquinone production, as well as insecticide, fungicide, gasoline anticoagulant, etc. to verify indene. Manufactures anthraquinone and alizarin dyes, and is also used as insecticide, fungicide, gasoline anticoagulant, etc. |
| production method | in coal tar, the content of anthracene is 1.4%. The I anthracene oil fraction obtained by continuous distillation of tar accounts for 12-14% of tar, the initial distillation point is 300 ℃, and the distillation amount before 350 ℃ is 95%. I anthracene oil is cooled and crystallized, vacuum filtered or part of the oil is removed by centrifuge. The crude anthracene after centrifugation contains more than 20-25%, and the remaining components are: anthracene 25-30%, carbazole 20-25%, phenanthrene 30% or so. The yield of anthracene accounts for 58-87% of the anthracene source in tar. In addition to benzene and naphthalene, anthracene is one of the most important components in coal tar. In the industrial production of anthracene, it is much more difficult to manufacture than naphthalene because phenanthrene and carbazole with similar boiling points must be separated. Even if distillation, crystallization and solvent extraction are skillfully combined, the yield is only 40-50%. The extraction and purification of anthracene from crude anthracene is to use the characteristics of phenanthrene easily soluble in oil to separate phenanthrene from anthracene and carbazole. The methods for further separation of anthracene and carbazole include distillation separation and potassium melting. |
| category | corroded articles |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD>: 17000 mg/kg; Abdominal cavity-mouse LD50: 430 mg/kg |
| stimulation data | skin-mouse 0.118 mg mild |
| explosive hazard characteristics | explosive when mixed with air; corrosive to skin and cornea; allergic substance |
| flammability hazard characteristics | open flame, high temperature, combustible in case of oxidant; Combustion produces stimulating smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidant. |
| fire extinguishing agent | sand, carbon dioxide, foam, mist water |
| occupational standard | TLV-TWA 0.2 mg/m3 |
| spontaneous combustion temperature | 540°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:06
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