90-12-0
1-Methylnaphthalene
CAS: 90-12-0
Molecular Formula: C11H10
90-12-0 - Names and Identifiers
| Name | 1-Methylnaphthalene |
| Synonyms | FEMA 3193 femanumber3193 1-Methylnaphthalene A-METHYLNAPHTHALENE 1 Methyl Napthalene α-Methylnaphthalene Methyl-1-naphthalene Naphthalene,1-methyl- ALPHA-METHYLNAPHTHALENE naphthalene,alpha-methyl 1-methylnaphthalene (alpha) |
| CAS | 90-12-0 |
| EINECS | 201-966-8 |
| InChI | InChI=1/C11H10/c1-9-5-4-7-10-6-2-3-8-11(9)10/h2-8H,1H3 |
| InChIKey | QPUYECUOLPXSFR-UHFFFAOYSA-N |
90-12-0 - Physico-chemical Properties
| Molecular Formula | C11H10 |
| Molar Mass | 142.2 |
| Density | 1.001g/mLat 25°C(lit.) |
| Melting Point | −22°C(lit.) |
| Boling Point | 240-243°C(lit.) |
| Flash Point | 180°F |
| JECFA Number | 1335 |
| Water Solubility | 0.026 g/L (25 ºC) |
| Solubility | 0.026g/l |
| Vapor Presure | 2 hPa (25 °C) |
| Appearance | Liquid |
| Color | Clear colorless to yellow |
| Exposure Limit | ACGIH: TWA 0.5 ppm (Skin) |
| BRN | 506793 |
| pKa | 37(at 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, oxygen. |
| Explosive Limit | 0.7-6.5%(V) |
| Refractive Index | n20/D 1.615(lit.) |
| Physical and Chemical Properties | Character: colorless oily liquid with naphthalene-like odor. melting point -30.6 ℃ boiling point 244.6 ℃ relative density 1.0202 refractive index 1.6170 flash point 82.2 ℃ solubility insoluble in water, soluble in ether and ethanol. |
| Use | Used as surfactant, water reducing agent, dispersant, drug and other organic synthesis of raw materials |
90-12-0 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R42/43 - May cause sensitization by inhalation and skin contact. R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S7 - Keep container tightly closed. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. 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. S23 - Do not breathe vapour. S36 - Wear suitable protective clothing. |
| UN IDs | UN 3082 9/PG 3 |
| WGK Germany | 2 |
| RTECS | QJ9630000 |
| TSCA | Yes |
| HS Code | 29029080 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 1840 mg/kg |
90-12-0 - Upstream Downstream Industry
| Downstream Products | 1,4-naphthalenedicarboxylic acid |
90-12-0 - Nature
Open Data Verified Data
A colorless oily liquid with a naphthalene-like odor that can volatilize with vapor. Relative density (d;o)1. 0202. Boiling point 244.6 °c. Melting Point -30.6 °c. Refractive index 6170. Flash point 82.2 °c. Spontaneous ignition point 529. Insoluble in water, soluble in ether and ethanol, this product is flammable.
Last Update：2024-01-02 23:10:35
90-12-0 - Preparation Method
Open Data Verified Data
in high-temperature tar containing about 0.8% ~ 1.2%, the wash oil fraction of 230~300 ℃ is dephenolized, pyridine base is removed, and then the methyl naphthalene fraction of 240~245 ℃ is cut by distillation, frozen to -20 ° C., at this time, p-methyl naphthalene precipitates, and the fraction that does not crystallize at -20 ° C is a-methyl naphthalene fraction, which is sulfonated and hydrolyzed to obtain an industrial pure product.
Last Update：2022-01-01 10:39:56
90-12-0 - Use
Open Data Verified Data
can be used for polyvinyl chloride fiber and polyester printing and dyeing carrier, Six Six Six emulsifier, but also can be used as heat carrier and solvent, surfactant, sulfur extraction agent, can also be used as the production of plasticizer, raw materials for fiber dyeing AIDS.
Last Update：2022-01-01 10:39:55
90-12-0 - Safety
Open Data Verified Data
- less toxic than naphthalene. The maximum allowable concentration in air is 20mg/m3. The operator should wear protective gear. This product in case of high fever, fire, oxidant burning danger, stored in a cool and ventilated warehouse, the temperature should not exceed 30 ℃. Throw and impact are not allowed during handling.
- it shall be packed in an asphalt hemp bag or plastic bag, and the bag shall be sealed tightly. The net weight of each bag shall not exceed 50kg. The package shall be marked with "flammable items.
Last Update：2022-01-01 10:39:56
90-12-0 - Reference Information
| FEMA | 3193 | 1-METHYLNAPHTHALENE |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | α-methylnaphthalene is an isomer of α-methylnaphthalene, mainly used in the manufacture of fluorescent brighteners, dyeing carrier vinyl chloride fiber, polyester dyeing carrier surfactant, heat carrier, pharmaceutical intermediates, sulfur extraction agent, can be used for the production of plasticizers, fiber dyeing AIDS. It can also be used as a diesel decane number measuring agent, a reagent for measuring the number of theoretical plates in a distillation column, a solvent for pesticides and insecticides, and a solvent for producing hydrogen peroxide by anthraquinone method. It can also be used to produce the plant growth regulator α-naphthylacetic acid. Fine α-methyl naphthalene can be used for the synthesis of 1 , 4 naphthalene dicarboxylic acid, used as raw materials for the production of fluorescent brightener dyes, also used for the production of engineering plastics resin, synthesis of 1-naphthalene two acid as plant growth hormone, synthesis of 1-naphthoic acid as a raw material for color photographic dyes, can also be used as pharmaceutical intermediates. |
| preparation method | 1.(1) The Industrial methyl naphthalene fraction is washed with 15 ~ 25% H2SO4 solution in a pickling tank, and 3.5~4.0 L H2SO4 solution is added per kg of quinoline, the heating temperature in the tank is controlled at 60~65 ℃, and the stirring is continuously carried out, then it is separated in the static separator, and the water containing quinoline is extracted; (2) the Industrial methyl naphthalene fraction after acid washing enters into the Alkali washing tank, carries on the Alkali washing with 10 ~ 20% KOH solution, and adds 13.0~17.0 liter KOH solution per kg indole, heating and maintaining boiling state in the tank, stirring continuously, and extracting the water separated by evaporation; (3) The Industrial methyl naphthalene fraction after alkali washing enters the filter, the impurities containing indole on the filter screen are extracted; (4) The Industrial methyl naphthalene fraction after alkali washing is passed through the filter to the middle of the rectification column for rectification after removing impurities, extraction of α-methylnaphthalene product in the middle-upper part of the rectification column the β-methylnaphthalene product is extracted near the top of the rectification column. 2.(1) preparation of α-chloromethylnaphthalene In a 1L three-necked round-bottomed flask equipped with a thermometer, condenser and Mercury-sealed stirrer, 64G (0.5mol) of naphthalene was placed, 27.5g(0.92mol) paraformaldehyde, 68.5g(1.1mol) glacial acetic acid, 70g(0.61mol)55% phosphoric acid and 107g(1.1mol) concentrated hydrochloric acid. The mixture was heated to 85 °c on a water bath and stirred vigorously for 6hr. After completion of the reaction, the reaction was cooled to 15 °c, then poured into a 500ml separatory funnel and washed twice with 30ml of water each time. Finally, it is washed with a cold solution of 15 mol of 10% potassium carbonate, the aqueous layer is separated carefully, 50ml of diethyl ether are added, dried with 10g of sodium carbonate for 1hr, and the lower aqueous layer is separated. The ether solution was dried with 20g of potassium carbonate for 8-12hr, and then the ether was distilled off using a Kjeldahl Flask at atmospheric pressure. The residue was subjected to distillation under reduced pressure, unreacted naphthalene was distilled off at 90 to 110 ° C./666.6Pa, and α-chloromethylnaphthalene was further distilled off at 145 to 153 ° C./186.5Pa. (2) preparation of active nickel catalyst under the condition of intense stirring and external cooling, the finely ground aluminum nickel alloy (containing 30 ~ 50% nickel) slowly dissolve in 4 times the amount of 25% sodium hydroxide solution. Then, at a temperature not higher than 90 ° C., it was heated until the hydrogen did not escape. The precipitate was washed with a 10% sodium hydroxide solution and then with distilled water until it was free of OH-ions by dumping. Finally, it was washed with ethanol and the resulting active nickel catalyst was stored in ethanol. The reaction formula is as follows: (3) preparation of α-methylnaphthalene 20g of α-chloromethylnaphthalene, 1g of active nickel, 2g of sodium acetate and 100g of ethanol are put into an autoclave and sealed, hydrogen gas exchange was performed three times. Then, hydrogen gas was passed to 4.5MPa, stirred, and the temperature was raised. The temperature in the kettle was controlled at 85-90 ° C., and the reaction was carried out for 2hr. The temperature was lowered to 50 ° C. And the air was discharged, and the material in the kettle was pressed out and the active nickel was filtered out (recycled) to obtain a filtrate. After concentration and recovery of 1/2 ethanol, hot distilled water is poured, and after cooling, The mixture was allowed to stand and layered to obtain an α-methylnaphthalene product. (4) purification of α-methylnaphthalene The obtained crude α-methylnaphthalene was subjected to a sulfonation reaction with concentrated sulfuric acid at 80 °c. After completion of the reaction, the reaction is hydrolyzed and layered by heating in dilute sulfuric acid, and then washed with 10% NaOH solution and water to obtain a fine product of 98% purity. FIG. 3 reaction principle of synthesis of α-methylnaphthalene |
| Application | 1. It is used in the manufacture of fluorescent brightener, vinyl chloride fiber as dyeing carrier, polyester dyeing carrier surfactant, heat carrier, pharmaceutical intermediate, sulfur extraction agent, 2. For the production of plasticizers, fiber dyeing AIDS 3. It is used as a reagent for determining the decane number of diesel oil, a reagent for determining the number of theoretical plates in a distillation column, a solvent for pesticides and insecticides, and a solvent for producing hydrogen peroxide by anthraquinone method. 4. Used for the production of plant growth regulator α-naphthylacetic acid. 5. Fine α-methyl naphthalene can be used for the synthesis of 1 , 4 naphthalene dicarboxylic acid, used as raw materials for the production of fluorescent brightener dyes, also used for the production of engineering plastics resin, synthesis of 1-naphthalene two acid as plant growth hormone, synthesis of 1-naphthoic acid as a raw material for color photographic dyes, can also be used as pharmaceutical intermediates. |
| primary reference | [1]http://www.chemmade.com/assistant/chemdic/casDetail-90-12-0.html. [2]http://www.sdqfchem.com/products01/id/9.html. [3]http://www.patent-cn.com/C07C/CN1122320.shtml. [4]http://www.doc88.com/p-349518836284.html. [5] Dong Yan. A new process for the synthesis of 1-methylnaphthalene [J]. Ningxia chemical industry, 1997,(02):14-16. |
| Use | 1. Used as raw materials for organic synthesis of surfactants, water reducing agents, dispersants, drugs and so on. It can be used for polyvinyl chloride fiber and polyester dyeing carrier, Six Six Six emulsifier, but also can be used as a heat carrier and solvent, surfactant, sulfur extraction agent, can also be used as a raw material for the production of plasticizers, fiber dyeing AIDS. The standard fuel used for the determination of the octane number and the number of ten alkanes of diesel fuel is also used in organic synthesis. 3. For organic synthesis, used as a printing and dyeing carrier, heat carrier, plasticizer, etc. raw materials for producing high-efficiency whitening agents; Determination of octane number and sixteen Alkane number of diesel oil; Raw materials for pesticide emulsifier and plant growth stimulating hormone α-naphthylacetic acid, solvent |
| production method | 1-methylnaphthalene mainly exists in naphthalene oil fraction (3.45%) and wash oil fraction (about 5.4%). Medium. 1. After the extraction of the residue oil and the wash oil fraction from the bottom of the column after the extraction of the naphthalene oil fraction, the neutral oil after the acid and alkali washing is preliminarily distilled, and the crude methyl naphthalene fraction at 230-270 ℃ is cut out, the cut volume is 25-30% of the raw material, not less than 60 theoretical trays, and the reflux ratio of 20:1 is used. The methyl naphthalene fraction of 240-250 ° C. Is cut. The methyl naphthalene fraction was redistilled once more in a rectification column of the same efficiency, and the crystallizable fraction at 237-241 °c and the fraction that was not crystallized at 241-245 °c were cut out. The crystallizable fractions are frozen to -10-20 °c and 2-methylnaphthalene is prepared by centrifugation or by extrusion crystallization. The filtrate and the above non-crystallized fractions are combined, washed with 95-98% concentrated sulfuric acid of 3-5% of the raw material, neutralized with alkali, washed and removed moisture, the fraction of less than 241 ° C. Was fractionated on the high efficiency distillation column, and the crystallization was removed by low temperature freezing, and more than 95% of technical grade 1-methyl naphthalene was obtained. After repeated sulfonation and hydrolysis, 98% purity of the refined product can be obtained. 2. In high-temperature tar containing about 0.8%-1.2%, dephenolization of the wash oil fraction at 230-300 ℃, depyridinium, rectification, cutting methyl naphthalene fraction at 240-245 ℃, freezing to -20 ℃, at this time, the β-methylnaphthalene precipitates, and the fraction that does not crystallize at -20 ° C. Is the α-methylnaphthalene fraction. After sulfonation and hydrolysis, an industrial pure product can be obtained. |
| category | relatively flammable solid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 1840 mg/kg |
| flammability hazard characteristics | in case of open flame, high temperature, flammable oxidant; Combustion stimulus smoke |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from the oxidant |
| extinguishing agent | water, dry sand, carbon dioxide, foam, 1211 extinguishing agent |
| Occupational Standard | SEL 20 mg/m3 |
| spontaneous combustion temperature | 984 ° F. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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