HSDB 184
Naphthalene
CAS: 91-20-3;72931-45-4
Molecular Formula: C10H8
HSDB 184 - Names and Identifiers
| Name | Naphthalene |
| Synonyms | Naftalen HSDB 184 AI3-00278 NAPHTHENE Naphthene NSC 37565 White tar NAPTHALIN NCI-C52904 Naphthalin NAPTHALENE Naphtalene CCRIS 1838 Albocarbon Mighty 150 Mighty RD1 Moth balls Naphthaline Naphthalene Camphor tar Dezodorator Moth flakes TAR CAMPHOR NAPHTHALENE Tar camphor 'LGC' (2402) 'LGC' (2603) 1-NAPHTHALENE Naphthalene, pure Naftalen [Polish] Naphthalene, molten Naphthalene (molten) RCRA waste number U165 Naphthalene, crude or refined EPA Pesticide Chemical Code 055801 Naphthalene, molten [UN2304] [Flammable solid] Naphthalene, crude or refined [UN1334] [Flammable solid] |
| CAS | 91-20-3 72931-45-4 |
| EINECS | 202-049-5 |
| InChI | InChI=1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H |
| InChIKey | UFWIBTONFRDIAS-UHFFFAOYSA-N |
HSDB 184 - Physico-chemical Properties
| Molecular Formula | C10H8 |
| Molar Mass | 128.17 |
| Density | 0.99 |
| Melting Point | 80-82 °C (lit.) |
| Boling Point | 218 °C (lit.) |
| Flash Point | 174°F |
| Water Solubility | 30 mg/L (25 ºC) |
| Solubility | methanol: soluble50mg/mL, clear, colorless |
| Vapor Presure | 0.03 mm Hg ( 25 °C) |
| Vapor Density | 4.4 (vs air) |
| Appearance | Faint beige to brown to salmon red powder |
| Specific Gravity | 1.145 |
| Color | White to almost white |
| Exposure Limit | TLV-TWA 10 ppm （～50 mg/m3) (ACGIH,MSHA, and OSHA); STEL 15 ppm(～75 mg/m3) (ACGIH); IDLH 500 ppm. |
| Merck | 14,6370 |
| BRN | 1421310 |
| Storage Condition | Store below +30°C. |
| Explosive Limit | 0.9-5.9%(V) |
| Refractive Index | 1.5821 |
| Physical and Chemical Properties | Colorless and lustrous monoclinic crystals. There is a strong smell of tar. Easy sublimation at room temperature. insoluble in water, soluble in ether, ethanol, chloroform, carbon disulfide, benzene, etc. |
| Use | Mainly used for the production of phthalic anhydride, but also the production of dyes, pharmaceuticals and other raw materials |
HSDB 184 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R38 - Irritating to the skin R11 - Highly Flammable R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R20 - Harmful by inhalation |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S46 - If swallowed, seek medical advice immediately and show this container or label. 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. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. S33 - Take precautionary measures against static discharges. S25 - Avoid contact with eyes. S9 - Keep container in a well-ventilated place. |
| UN IDs | UN 1334 4.1/PG 3 |
| WGK Germany | 3 |
| RTECS | QJ0525000 |
| TSCA | Yes |
| HS Code | 29029010 |
| Hazard Class | 4.1 |
| Packing Group | III |
| Toxicity | Acute oral LD50 for guinea pigs 1,200 mg/kg, mice 533 mg/kg, rats 1,250 mg/kg (quoted, RTECS, 1985). |
HSDB 184 - Nature
Open Data Verified Data
colorless and lustrous monoclinic crystals. Flammable. Camphor ball smell, at room temperature is also quite volatile, can sublimate. The relative density is 1. 145 and the melting point is 80. 29 ℃. Boiling point 218 °c. Ignition point 86. Spontaneous ignition point was 526. 11 ℃. Refractive index (12~5)1. 5898. Flash point (Open Cup) 78. 89 °c. Insoluble in water, soluble in ether, ethanol, chloroform, carbon disulfide, benzene, etc. It can also volatilize with water vapor. Form an explosive mixture with air; Explosive limit of 0.9% to 5.9% by volume.
Last Update：2024-01-02 23:10:35
HSDB 184 - Preparation Method
Open Data Verified Data
- by the separation of coal tar, high temperature coal tar in naphthalene accounted for about 8 ~ 12%, the coal tar distillation, cut kerosene, dephenolization, dequinoline, distillation to get the finished naphthalene. lOt Coal tar is consumed per ton of naphthalene.
- from petroleum hydrocarbons: catalytic heavy reforming oil, catalytic cracking light cycle oil, cracking to produce ethylene by-product tar and so on.
Last Update：2022-01-01 10:39:54
HSDB 184 - Use
Open Data Verified Data
for the basic chemical raw materials, mainly used for the production of phthalic anhydride, various naphthol, naphthylamine, etc., is the production of synthetic resin, plasticizer, rubber antioxidant, surfactant, synthetic fiber, dye, coating, pesticides, medicines and spices and other raw materials.
Last Update：2022-01-01 10:39:53
HSDB 184 - Safety
Open Data Verified Data
- naphthalene is less water-soluble and less likely to be absorbed, so it is less toxic. Inhalation of concentrated naphthalene vapor or naphthalene powder, can promote people Vomit, discomfort, Head Pain. In particular, damage to the cornea, causing small blisters and punctate turbidity, but also can make the skin inflammation, sometimes can cause pathological changes in the lungs, but also damage the kidneys, causing hematuria, but no carcinogenicity. The maximum allowable concentration of naphthalene in the workplace is 10 x 10-6. Production equipment and containers should be closed to prevent the evaporation of vapor powder, and the operation site should be forced ventilation. If poisoning occurs, immediately move to the fresh air, drink hot water, so that Vomit, artificial respiration, severe cases sent to the hospital for treatment.
- liquid naphthalene is transported by tank car, and solid fine naphthalene is packed in kraft paper with a net weight of 25kg. During transport and storage, fire shall be prevented.
Last Update：2022-01-01 10:39:54
HSDB 184 - Reference Information
| Henry's Law Constant | 5.64 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| LogP | 3.7 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 2B (Vol. 82) 2002 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| fused ring aromatic hydrocarbon | naphthalene is the simplest fused ring aromatic hydrocarbon composed of two benzene rings, commonly known as "sanitary ball". It is one of the main products of coal tar processing. Naphthalene appears in industry as crude naphthalene (industrial naphthalene and pressed naphthalene) and refined naphthalene. The molecular formula of naphthalene is C10H8, and the molecular weight is 128.17. The melting point is 80.28 ℃, the solid density is 1.145g/cm3, the liquid density (85 ℃) is 0.9752g/cm3, the specific heat capacity (100 ℃) is 1809j/(kg k), and the refractive index (85 ℃) is 1.5898. Naphthalene is a colorless monoclinic crystal, volatile, sublimated, has a special smell, flammable, and can form an explosive mixture with air; its petroleum ether solution is red-purple fluorescent under a mercury lamp, almost insoluble in water, and soluble in ether, Alcohol, benzene and other solvents. Naphthalene vapor and dust can be inhaled into the human body or absorbed through the skin, and the limit allowable concentration in the air is 20mg/m3. Naphthalene is one of the basic raw materials in dyes, plastics, paints, medicines and pesticides. It has been directly used as a sanitary ball for clothing and fur moth-proof. Naphthalene is more prone to substitution reactions than benzene-halogenation, nitration, sulfonation and Fourier reaction. The electron density on the α-carbon atom is higher, and the rate of generating α-substituted products is faster; the stability of β-substituted products is greater. The ratio of α-and β-substituted products in the substitution reaction depends on the nature of the reagent, catalyst, solvent, temperature and other factors. For example, the halogenation and nitration reactions are irreversible, and generally mainly generate α-substituted products, and the bromination reaction can occur without a catalyst. |
| Molecular structure | The molecular structure of naphthalene is made up of two benzene rings sharing two adjacent carbon atoms. Modern physical methods prove that the diphenyl ring is in the same plane, each carbon atom is sp2 hybrid, and the p orbitals of all carbon atoms are parallel to each other and overlap to form a closed conjugated system. Unlike the benzene ring, the overlap of the p orbitals of the naphthalene molecular structure is not exactly the same, the electron density is not completely averaged, and the bond lengths between carbon atoms are not equal. The position of the substituent on the naphthalene ring can be represented by α,β, and can also be represented by Arabic numerals. For example: According to the molecular orbital method, the electron density in the naphthalene molecule is the highest at the α position, and the β position is the second. naphthalene is a white flake crystal with a melting point of 80.6 ℃, a boiling point of 218 ℃, a relative density of 0.9625(100/4 ℃), a special smell, volatilization, easy sublimation, and insecticidal effect of steam, which can be used as an anti-moth agent. The chemical properties of naphthalene are more active than benzene, and it can undergo substitution, addition, oxidation and other reactions, and the α position is more prone to reaction than the β position. |
| refined naphthalene | refined naphthalene refers to a naphthalene product containing more than 98.45% naphthalene obtained by further purification of crude naphthalene (industrial naphthalene or pressed naphthalene). The production methods of refined naphthalene mainly include melting-crystallization method (see naphthalene melting-crystallization refining), hydrogenation method (see naphthalene hydrogenation refining), pickling distillation method, solvent crystallization method, sublimation method and formaldehyde method. The pickling distillation method has simple process and convenient operation, but it has more naphthalene loss, serious equipment corrosion, difficult treatment of waste acid, and poor production environment, and has been gradually eliminated. Sublimation products have low purity and are not commonly used. Pickling distillation method: wash crude naphthalene with 96 ~ 98% concentrated sulfuric acid, sulfonate and polymerize thiazene and unsaturated compounds into resinous substances (commonly known as acid tar), combine basic compounds with sulfuric acid and transfer into sulfuric acid layer, and acids are removed during subsequent alkaline washing to obtain refined naphthalene. The process flow is as follows: crude naphthalene (industrial naphthalene or pressed naphthalene) is heated and melted, and the temperature continues to rise to 90~95 ℃, concentrated sulfuric acid with a total amount of 4% (for industrial naphthalene) is added into the pickling tank several times, stirred and then standing for separation, sulfate base is discharged from the bottom, and the liquid naphthalene discharged from the upper part is washed with hot water and 10 ~ 12% sodium hydroxide solution in turn. The liquid naphthalene flowing out of the alkali washing separator enters the vacuum distillation tower, and the vacuum degree at the top of the tower is kept at 8.0~10.7kPa. The refined naphthalene produced from the top of the tower is sent to the naphthalene drum crystallization machine through the refined naphthalene receiving tank to make flakes, and its crystallization point is above 79.3 ℃. The loss of naphthalene during pickling is about 4 ~ 5% (for pressed naphthalene) and 4 ~ 9% (for industrial naphthalene). In order to improve the pickling effect and reduce the loss of naphthalene, the Soviet Union used sulfuric acid formaldehyde method to wash and purify. Formaldehyde method: unsaturated compounds in crude naphthalene and sulfur indene and other impurities in acidic medium condensation and formaldehyde into resin-like substances, after separation and removal. The molten crude naphthalene is first dehydrated and polycondensed with concentrated sulfuric acid, and then further polycondensation with formaldehyde sulfuric acid solution to separate and remove the resin layer, and then neutralized with alkali, washed with water, rectified and sliced to obtain refined naphthalene with a crystallization point greater than 79.3 ℃. The refining rate of naphthalene is about 90%. It can also be directly refined with formaldehyde sulfuric acid solution without the process of concentrated sulfuric acid dehydration and polycondensation. |
| important chemical raw material | naphthalene is an important chemical raw material. coal tar contains about 10% naphthalene, which can be obtained from the middle oil fraction of coal tar or the high boiling point fraction obtained from the cracking of petroleum products by crystallization. Its output can be used as one of the indicators to measure the development level of organic chemical industry. About 80% of naphthalene is used to prepare phthalic anhydride, which is an important organic chemical raw material, and further synthesizes plasticizers and some dyes. The rest are used as dye intermediates and the production of tanning and surfactants. A small amount is used to replace camphor to make sanitary pills, and use its special smell for home clothing to repel insects and moth. But naphthalene vapor or dust inhalation can cause headache, nausea, large amount of corneal opacity and optic neuritis, myocarditis and so on. The chemical properties of naphthalene are more active than benzene, and sodium metal is reduced to 1, 4-dihydronaphthalene in boiling anhydrous ethanol; in boiling pentanol, it is all reduced to 1,2,3, 4-Tetrahydronaphthalene; oxidized to 1, 4-naphthoquinone by chromic acid. Phthalic anhydride can be obtained by high-temperature catalytic oxidation of vanadium pentoxide, which is an important organic chemical intermediate. Naphthalene is more prone to substitution reactions than benzene, and the α position is more active than the β position. Nitrification can yield high-yield α-nitronaphthalene and a small amount of β-nitronaphthalene; under the action of catalysts such as ferric chloride, it reacts with halogen, The main product is also α-halogenated naphthalene. There are two products in sulfonation reaction. α-naphthalenesulfonic acid is mainly obtained at lower temperature (60 ℃). At higher temperature (160 ℃), β-naphthalenesulfonic acid is mainly obtained. Because sulfonation is a deliverable reaction, the increase in temperature converts the generated α-naphthalenesulfonic acid into β-naphthalenesulfonic acid. Acylation reaction can be carried out under the catalysis of anhydrous aluminum trichloride to form a mixture of α and β-acylnaphthalene. Naphthalene is flammable whether it is solid or liquid. Crude naphthalene may spontaneously ignite at high temperatures. Steam or fine powder is explosive when mixed in a certain proportion in the air. Pure naphthalene is generally not corrosive, but it contains impurities, especially when it contains phthalic anhydride. Reference materials: Yuan Yunkai, edited by Gu Mingyuan. Science and Technology Social Dictionary · Chemistry. Hangzhou: Zhejiang Education Press. |
| naphthalene melting-crystallization refining | using the principle of redistribution of components between liquid and solid phases during cooling crystallization of molten crude naphthalene, the process of purifying naphthalene through multiple melting crystallization. It is one of the processes for refining crude naphthalene obtained from the processing of naphthalene oil fractions. The impurities in crude naphthalene generally reduce the melting point of naphthalene, so when the liquid crude naphthalene is slowly cooled, the naphthalene first crystallizes and precipitates, and the impurities accumulate in the liquid phase. If the precipitated naphthalene melts and crystallizes again, the crystallization purity of the precipitated naphthalene is further improved. Strictly control the temperature and speed of the melting and crystallization process, and finally obtain high-purity refined naphthalene products. Naphthalene melting-crystallization refining can be carried out continuously, semi-continuously or intermittently. The main impurity in industrial naphthalene is thioindene. The boiling point of thioindene is only 2 ℃ different from the boiling point of naphthalene, which is difficult to remove by distillation, and their crystallization points differ by 48 ℃, so it is more appropriate to separate them by melting-crystallization method to refine naphthalene. A brief history of development: In 1952, W.G. Pfann first proposed the melting-crystallization refining technology (regional melting), which is mainly used for the purification of semiconductors and metal materials, and can also be used for the purification of organic compounds. The French company Probeud used this method to carry out experiments to purify naphthalene, and realized industrial production in the UK in 1962. Later, melting-crystallization refining processes for purifying naphthalene such as the Brody method of the Australian Union Carbide Company and the Sulzer method of Switzerland appeared. In 1985, China built the Brody process refined naphthalene device, and later built some Proabud-type devices. Process flow: There are three types of Brody method, Sulzer method and Prooud method. |
| Use | Used as solvent and analytical reagent, also used in organic synthesis Synthetic medicine, insecticides, spices, dyes, rubber antioxidant Mainly used in the production of phthalic anhydride, but also a raw material for the production of dyes, medicines, etc. Naphthalene is a raw material in the production of pesticides, which can be made into methyl naphthol and ethyl naphthol, it can also be oxidized to phthalic anhydride to further form phthalimide, and it can also be used with chloroacetic acid to form naphthalene acetic acid. It can be used as an intermediate for insecticides such as imidothion, carbaryl, herbicide methoxane, dioxalamine, plant growth regulator naphthalene acetic acid and naphthoxyacetic acid. Naphthalene is the most important polycyclic hydrocarbon in industry. It is mainly used to produce phthalic anhydride, various naphthols, naphthylamines, etc. It is a raw material for the production of synthetic resins, plasticizers, dyes, surfactants, synthetic fibers, coatings, pesticides, medicines, spices, rubber additives and pesticides. The use distribution of naphthalene varies from country to country. About 70% are used to produce phthalic anhydride, about 15% are used to dye intermediates and rubber additives, about 6% are pesticides, and about 4% are tanning agents. A large proportion of pesticides are used in the United States, mainly for the production of carbaryl. Using naphthalene as raw material, through unit operations such as sulfonation, nitration, reduction, amination, and hydrolysis, a variety of intermediates can be produced. The application of refined naphthalene is still expanding. The new product "super plastic material" is naphthalene sulfonate formaldehyde condensate, which can be used as a cement additive to increase the plastic deformation of concrete without reducing its strength. Demand will grow at a rate of 5-10% in the next few years. It is used for anti-mildew and anti-corrosion of leather. It is mainly used for the production of phthalic anhydride, and is also the basic raw material for the preparation of dyes, medicines, plastics, etc. It can be used for the manufacture of dye intermediates, diffusive agents, water reducing agents, etc. The available dyes of refined naphthalene, medicine and other fields, such as the production of 2-naphthol, 1-naphthol and methylnaphthol, etc., are also the main raw materials for the production of camphor. Used in the production of phthalic anhydride, dye intermediates, rubber additives and pesticides Solvents for crystallization of insoluble dyes in organic analysis. Determination of molecular weight. Colorimetry standard. Standard for the determination of carbon and hydrogen by organic microanalysis. Crystal organic scintillator in liquid scintillation counting. Correct the thermometer. Organic synthesis. |
| production method | crude naphthalene is refined from clay to obtain refined naphthalene. 1. separated from coal tar, naphthalene in high-temperature coal tar accounts for about 8%-12%. the coal tar is distilled, kerosene is cut, dephenolized, dequinoline, and distilled to obtain finished naphthalene. Consumption of 10t coal tar per ton of naphthalene. 2. Made from petroleum hydrocarbons: catalytic heavy reforming oil, catalytic cracking light cycle oil, by-product tar for cracking ethylene, etc. Its composition is as follows: total amount of coal tar aromatics (m),% 90-95 45-65 70-95 95-100 aromatics composition (m),% alkylbenzene 20 25 20 5 dihydroindene and tetrahydronaphthalene 15 25 10 5 alkyl indene 2 7 18 3 alkyl naphthalene 55 35 45 75 biphenyl and alkyl 6 5 10 tricyclic compound 2 2 2 2 total, naphthalene can be produced by catalytic dealkylation and thermal release of aromatic hydrocarbons over% 100 100 100. the preparation method is in high temperature coal tar (naphthalene accounts for about 8% ~ 12%), the tar is distilled to remove light oil fraction and phenol oil fraction, and then cut the fraction at 210~230 ℃ to obtain naphthalene oil fraction. The naphthalene oil fraction is cooled and crystallized to obtain crude naphthalene with a naphthalene content of 75%, and then the crude naphthalene is filtered, dried and pressed to obtain a squeeze block with a naphthalene content of 96% ~ 98%, and the pressed naphthalene is melted, Add sulfuric acid to wash and purify, then use 10% sodium hydroxide to neutralize and dephenolate, then distill and evaporate water, collect 100~130 ℃ fractions, and finally crystallize to form the finished product. If it is made from petroleum hydrocarbons, its raw materials come from catalytic heavy recombination oil, catalytic cracking fine cycle oil, by-product tar of cracking ethylene, etc. |
| category | flammable solids |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 490 mg/kg; Oral-mouse LD50: 316 mg/kg |
| stimulation data | skin-rabbit 495 mg/24 hours mild; Eye-rabbit 100 mg/24 hours mild |
| explosive hazard characteristics | blastable when mixed with air |
| flammability hazard characteristics | flammability in case of open flame, high temperature and oxidant; Combustion produces stimulating smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants and acids |
| fire extinguishing agent | water, foam, carbon dioxide, dry powder |
| occupational standard | TWA 10 PPM (50 mg/m3); STEL 15 PPM (75 mg/m3) |
| auto-ignition temperature | 978 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-threatening and health concentration | 250 ppm |
Last Update：2024-04-09 21:32:01
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