1,2,3,4-tetrahydro-9H-fluoren-9-one
Tetrahydrofuran
CAS: 109-99-9
Molecular Formula: C4H8O
1,2,3,4-tetrahydro-9H-fluoren-9-one - Names and Identifiers
| Name | Tetrahydrofuran |
| Synonyms | THF oxolane Furanidine Tetrahydrofuran Diethylene oxide Furan, tetrahydro- Butane, alpha,delta-oxide Cyclotetramethylene oxide Sodium tri-sec-butylborohydride 1,2,3,4-tetrahydro-9H-fluoren-9-one TETRAMETHYLENE ETHER GLYCOL 2000 POLYMER |
| CAS | 109-99-9 |
| EINECS | 203-726-8 |
| InChI | InChI=1/C13H12O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1,3,5,7H,2,4,6,8H2 |
| InChIKey | WYURNTSHIVDZCO-UHFFFAOYSA-N |
1,2,3,4-tetrahydro-9H-fluoren-9-one - Physico-chemical Properties
| Molecular Formula | C4H8O |
| Molar Mass | 72.11 |
| Density | 0.887 g/mL at 20 °C |
| Melting Point | -108°C |
| Boling Point | 66 °C |
| Flash Point | 6 °F (-14 ℃) |
| Water Solubility | miscible |
| Solubility | water: soluble |
| Vapor Presure | <0.01 mm Hg ( 25 °C) |
| Vapor Density | 2.5 (vs air) |
| Appearance | Liquid |
| Specific Gravity | 0.89 |
| Color | <10(APHA) |
| Odor | Ethereal, detectable at 2 to 50 ppm |
| Exposure Limit | TLV-TWA 200 ppm (590 mg/m3) (ACGIH,MSHA, and OSHA); STEL 250 ppm(ACGIH); IDLH 20,000 ppm (NIOSH). |
| Maximum wavelength(λmax) | ['λ: 245 nm Amax: ≤0.26', , 'λ: 275 nm Amax: ≤0.046', , 'λ: 315 μm Amax: ≤0.0044'] |
| Merck | 14,9211 |
| BRN | 102391 |
| PH | 7-8 (200g/l, H2O, 20℃) |
| Storage Condition | Store at +5°C to +30°C. |
| Stability | Stable. Incompatible with halogens, strong oxidizing agents, strong reducing agents, strong bases, oxygen. May generate explosive peroxides in storage if in contact with air. Highly flammable. |
| Sensitive | Air Sensitive & Hygroscopic |
| Explosive Limit | 1.5-12.4%(V) |
| Refractive Index | n20/D 1.465 |
| Physical and Chemical Properties | Characteristics of colorless transparent liquid, ether odor. boiling point 67 ℃ freezing point -108 ℃ relative density 0.985 refractive index 1.4050 flash point -17 ℃ solubility, ketone, benzene, Ester, ether, hydrocarbon miscible. |
| Use | Used as solvent, raw material of organic synthesis |
1,2,3,4-tetrahydro-9H-fluoren-9-one - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R36/37 - Irritating to eyes and respiratory system. R19 - May form explosive peroxides R11 - Highly Flammable R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S33 - Take precautionary measures against static discharges. S29 - Do not empty into drains. S16 - Keep away from sources of ignition. S46 - If swallowed, seek medical advice immediately and show this container or label. S37 - Wear suitable gloves. S13 - Keep away from food, drink and animal foodstuffs. |
| UN IDs | UN 2924 3/PG 2 |
| WGK Germany | 1 |
| RTECS | MD0916000 |
| FLUKA BRAND F CODES | 3-10-23 |
| TSCA | Yes |
| HS Code | 29321100 |
| Hazard Class | 3 |
| Packing Group | II |
| Toxicity | LD50 oral (rat) 2880 mg/kg LC50 inhal (rat) 21,000 ppm (3 h) PEL (OSHA) 200 ppm (590 mg/m3) TLV-TWA (ACGIH) 200 ppm (590 mg/m3) STEL (ACGIH) 250 ppm (737 mg/m3) |
1,2,3,4-tetrahydro-9H-fluoren-9-one - Upstream Downstream Industry
1,2,3,4-tetrahydro-9H-fluoren-9-one - Reference Information
| update date: | 2022/11/11 19:50:47 |
| relative polarity | 0.207 |
| pH indicator color change ph range | 7 |
| freezing point | -108 ℃ |
| Henry's Law Constant | 1.54 (static headspace-GC, Welke et al., 1998) |
| LogP | 0.45 at 25℃ |
| (IARC) carcinogen classification | 2B (Vol. 119) 2019 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Tetrahydrofuran, abbreviated as THF, is a heterocyclic organic compound. It belongs to ethers and is the complete hydrogenation product of aromatic compound furan. Tetrahydrofuran is one of the strongest polar ethers. It is used as a moderately polar solvent in chemical reactions and extraction. It is a colorless and volatile liquid at room temperature and has an odor similar to ether. Soluble in most organic solvents such as water, ethanol, ether, acetone, benzene, etc., and are called "universal solvents". It is partially miscible with water energy at room temperature, and some illegal reagent manufacturers use this to make huge profits from tetrahydrofuran reagent mixed with water. Due to the tendency of THF to form peroxides in storage, industrial products generally add antioxidant BHT. Moisture content ≦ 0.2%. It has the characteristics of low toxicity, low boiling point and good fluidity. At present, the main domestic manufacturers of tetrahydrofuran include BASF China, Dalian Yizheng (DCJ), Shanxi Sanwei, Sinochem International, PetroChina Qianguo Refinery, etc., and some other PBT plants also have by-products. the sales indexes of tetrahydrofuran in the United States and Europe of LyondellBasell industry company of the United States are: purity 99.90%, chromaticity (APHA)10, moisture 0.03%,THF hydroperoxide 0.005%, total impurity 0.05%, oxidation inhibitor 0.025% ~ 0.035%. The most important use in the polyurethane industry is as a monomer raw material for polytetrahydrofuranediol (PTMEG), which is also one of the main uses of THF. |
| Main uses | 1. Raw materials for spandex synthesis reaction Tetrahydrofuran itself can be polycondensed (repolymerized by cation-initiated ring opening) to form polytetramethylene ether glycol (PTMEG), also known as tetrahydrofuran homogeneous polyether. PTMEG and toluene diisocyanate (TDI) are made of special rubber with wear resistance, oil resistance, good low temperature performance and high strength. Block polyether polyester elastic material is made of dimethyl terephthalate and 1, 4-butanediol. PTMEG with a relative molecular mass of 2000 and p-methylene bis (4-phenyl) diisocyanate (MDI) are used to prepare polyurethane elastic fibers (spandex, SPANDEX fibers), special rubber and some special purpose coatings. the most important use of THF is to produce PTMEG. according to rough statistics, more than 80% of THF in the world is used to produce PTMEG, while PTMEG is mainly used to produce elastic spandex fiber. 2. solvent with excellent performance tetrahydrofuran is a commonly used excellent solvent, especially suitable for dissolving PVC, polyvinylidene chloride and butaniline. it is widely used as a solvent for surface coating, anticorrosive coating, printing ink, magnetic tape and film coating. when used for electroplating aluminum liquid, the thickness of aluminum layer can be controlled arbitrarily and bright. Tape coating, PVC surface coating, cleaning PVC reactor, removal of PVC film, cellophane coating, plastic printing ink, thermoplastic polyurethane coating, adhesive solvent, commonly used in surface coating, protective coating, ink, extractant and surface treatment agent of artificial synthetic leather. 3. used as raw materials for organic synthesis such as pharmaceuticals used to produce tetrahydrothiophene, 1.4-dichloroethane, 2.3-dichlorotetrahydrofuran, valerolactone, butyrolactone and pyrrolidone, etc. In the pharmaceutical industry, it is used to synthesize Kopiqing, Rifamycin, progesterone and some hormone drugs. Tetrahydrothiophenol is produced by hydrogen sulfide treatment, which can be used as an odor agent (identification additive) in fuel gas and is also the main solvent in the pharmaceutical industry. 4. other uses chromatographic solvent (gel permeation chromatography), used for natural gas flavoring, acetylene extraction solvent, polymer light stabilizer, etc. With the wide application of tetrahydrofuran, especially the rapid growth of China's spandex industry in recent years, the demand for PTMEG in China is increasing day by day, and the demand for tetrahydrofuran is also showing a rapid growth trend. |
| Purification and water removal methods | Tetrahydrofuran is miscible with water and often contains a small amount of water and peroxide. If anhydrous tetrahydrofuran is to be produced, lithium aluminum hydride can be refluxed under moisture isolation (usually about 2~4g lithium aluminum hydride is required for 1000mL) to remove the water and peroxide, and then distilled. Do not evaporate dry when collecting the fraction at 66 ℃ for distillation, and pour out the remaining small amount of residual liquid). The refined liquid is added to the sodium filament and should be stored in a nitrogen atmosphere. When treating tetrahydrofuran, a small amount should be used for testing. Only a small amount of water and peroxide can be purified when it is determined that there is only a small amount of water and peroxide, and the effect is not too intense. The peroxide in tetrahydrofuran can be tested with acidified potassium iodide solution. If there are more peroxides, it should be treated separately. |
| hazard | tetrahydrofuran is a class 3.1 low flash point flammable liquid, extremely flammable, vapor can form an explosive mixture with air, the explosion limit is 1.5% ~ 12% (volume fraction), irritating. Its highly combustible nature is also one of the safety hazards. The biggest safety hazard of THF is that it will slowly form highly explosive organic peroxides when exposed in the air. In order to reduce this hidden danger, 2, 6-di-tert-butyl-p-cresol (BHT) is usually added to commercially available THF to inhibit the production of organic peroxides. At the same time, THF should not be evaporated dry, because organic peroxides will be enriched in the distillation residue. |
| toxicology | rat oral LD50: 1650 mg/kg; Inhalation of LC50: 21000 ppm/3H. Mice inhaled LCLo: 24000 mg/m3/2H. Low toxicity. This product has irritating effect on skin and mucous membrane. High concentration has an anesthetic effect, and the anesthetic concentration is similar to the lethal concentration. High dose fashion can have liver toxicity. Inhaled 590mg/m ^ 3 for 3 hours, the eyes, face and nasal mucosa were red. Inhaled> 147750mg/m ^ 3, corneal edema and turbidity, salivation, runny nose and nosebleeds occurred. Rats, guinea pigs, rabbits and cats were treated at a concentration of 50mg/L for 3 hours, and some animals fell sideways. Deep anesthesia occurred at 100mg/L, and some animals died after 1~4.5 hours of exposure. Anesthesia occurred at 200mg/L for 1 hour, which can cause death if it acts for a long time. Rats with inhalation concentration> 14000mg/m 3, sleep, rigidity, deep coma, convulsions, and epileptiform brain waves. For anesthesia, animals can be tolerated after repeated inhalation. Liver fat infiltration and cytolysis may occur in animals exposed to high doses or repeated exposure. Orotic poisoning can cause gastric bleeding and ulcers. 20% aqueous solution directly applied to rabbit skin can cause moderate skin irritation, 50% aqueous solution can cause serious corrosive damage. 20% aqueous solution can cause severe keratitis in rabbit eyes. Explosive peroxides are formed when THF comes into contact with air, which can increase the stimulating effect of THF. It is reported abroad that the concentration of human anesthesia is 73800mg/m 3. The human olfactory threshold is 88.5 mg/m 3. |
| Use | Used as a solvent and raw material for organic synthesis Used as a chromatographic analysis reagent, organic solvent and nylon intermediate Tetrahydrofuran, also known as monoxia pentacyclo, oxopentane, and tetramethylene oxygen, is an intermediate for the synthesis of the pesticide phenylbutyltin. In addition, it can be directly used to make synthetic fibers, synthetic resins, and synthetic rubber, it is also a solvent for many polymeric materials, precision tapes and electroplating industries. It is also used to make adiponitrile, adipic acid, adipic acid, adipic acid, adipic acid, butanediol, γ-butyrolactone, etc., in the pharmaceutical industry, It can be used to produce Kopiqing, progesterone, rifamycin and pharmaceutical solvents. THF is an important organic synthetic raw material and a solvent with excellent performance. It is especially suitable for dissolving PVC, polyvinylidene chloride and butaniline. It is widely used as a solvent for surface coatings, anticorrosive coatings, printing inks, tapes and film coatings, and as a reaction solvent. When used for electroplating aluminum liquid, the thickness of aluminum layer can be controlled arbitrarily and bright. THF itself can be polycondensed (repolymerized by cation-initiated ring opening) to form polytetramethylene ether glycol (PTMEG), also known as tetrahydrofuran homogeneous polyether. PTMEG and toluene diisocyanate (TDI) are made of special rubber with wear resistance, oil resistance, good low temperature performance and high strength. Block polyether polyester elastic material is made of dimethyl terephthalate and 1, 4-butanediol. PTMEG with a relative molecular mass of 2000 and p-methylene bis (4-phenyl) diisocyanate (MDI) are the raw materials for making polyurethane elastic fibers (spandex, I .e. SPANDEX fibers), special rubber and some special purpose coatings. In organic synthesis, it is used to produce tetrahydrothiophene, 1.4-dichloroethane, 2.3-dichlorotetrahydrofuran, valerolactone, butyrolactone and pyrrolidone. In the pharmaceutical industry, THF is used to synthesize Kopiqing, Rifamycin, progesterone and some hormone drugs. THF is treated with hydrogen sulfide to produce tetrahydrothiophenol, which can be used as an odor agent (identification additive) in fuel gas. THF can also be used as a surface treatment agent for synthetic leather. Paper chromatography of amino acids and peptides. Solvent. Organic synthesis. High performance liquid chromatography, ultraviolet luminescence photometric analysis. |
| Production method | Industrial production was the first to use sugar aldehyde as raw material, and the mixture of sugar aldehyde and steam was passed into a zinc-chromium-manganese metal oxide (or palladium) catalyst In the reactor, the carbonyl group is removed at 400-420 ℃ to form furan; then the skeleton nickel is used as the catalyst, and furan is hydrogenated at 80-120 ℃ to prepare tetrahydrofuran. This method produces 1 ton of tetrahydrofuran and consumes about 3 tons of polysaccharide aldehyde. There are many production methods developed later. The industrialized method is the 1, 4-butanediol catalytic dehydration ring method, because butanediol is made from acetylene and formaldehyde. This method is called the Reppe method; The production of tetrahydrofuran using 1, 4-dichlorobutadiene, a by-product of chloroprene rubber monomer, is called the dichlorobutadiene method; in recent years, a catalytic hydrogenation method using maleic anhydride as a raw material has been developed. There are 5 production processes for tetrahydrofuran. (1) The furfural method is obtained by the furfural decarbonylation to generate furan, which is then hydrogenated. This is one of the first methods to produce tetrahydrofuran in industry. Furfural is mainly produced by hydrolysis of agricultural and sideline products such as corncob. The law has serious pollution, which is not conducive to large-scale production and has been gradually eliminated. (2) Maleic anhydride catalytic hydrogenation method Maleic anhydride and hydrogen enter the reactor containing nickel catalyst from the bottom, and the ratio of tetrahydrofuran to γ-butyrolactone in the product can be controlled by adjusting the operating parameters. The reaction product and the raw material hydrogen are cooled to about 50°C and enter the bottom of the scrubber to separate the unreacted hydrogen and gaseous and liquid products. The unreacted hydrogen and gaseous products are washed and circulated to the reactor, and the liquid product is distilled To obtain tetrahydrofuran products. The ratio of γ-butyrolactone to tetrahydrofuran can be arbitrarily adjusted in the range of 0 ~(5 ∶ 1). The single-pass conversion rate of maleic anhydride reaches 100%, the selectivity of tetrahydrofuran is 85% ~ 95%, and the product content reaches 99.97%. The process has the characteristics of good catalyst performance, simple process and low investment. (3)1, 4-butanediol dehydration cyclization method The process is as follows: adding 1087kg 22% sulfuric acid aqueous solution to the reactor, adding 1,4-butanediol at a speed of 110kg/h at 100°C, maintaining the top temperature at 80°C, and obtaining an aqueous solution containing 80% tetrahydrofuran from the top of the tower at a speed of about 110kg/h. After 50t of 1,4-butanediol was added, about 70kg of coke was removed from the reactor. The coke is filtered, and the obtained aqueous sulfuric acid solution can be reused, and the yield of tetrahydrofuran in this process can reach more than 99%. Sulfuric acid is the earliest catalyst used in the industrial production of tetrahydrofuran, and it is also a catalyst widely used in production today. This process is mature, the process is relatively simple, the reaction temperature is low, the yield of tetrahydrofuran is high, but sulfuric acid is easy to corrode equipment and pollute the environment. (4) Dichlorobutene method uses 1, 4-dichlorobutene as raw material, hydrolyzes to generate butene diol, and then catalyzes hydrogenation. 1, 4-dichlorobutene is hydrolyzed in sodium hydroxide solution to generate butene glycol at 110°C. Centrifugal separation removes sodium chloride, the filtrate is concentrated in an evaporative crystallizer to separate alkali metal carboxylate, and then In the distillation tower to remove high boiling matter. The refined butylene glycol is sent to the reactor, with nickel as the catalyst, at 80~120 ℃ and a certain pressure, the butylene glycol is hydrogenated to form butanediol, after distillation, into the human cyclization reactor, under normal pressure and 120~140 ℃ in acidic medium to generate crude tetrahydrofuran, distillation dehydration and depressurization, and finally distillation to obtain high purity tetrahydrofuran. This method is simple to operate, mild conditions, high yield, less catalyst consumption, and can be used continuously. (5) Butadiene oxidation method using butadiene as raw material, by oxidation of furan, and then hydrogenation. This law has been industrialized abroad. |
| category | flammable liquid |
| toxicity classification | poisoning |
| acute toxicity | oral administration-rat LD50:1650 mg/kg; Inhalation-mouse LCL0: 24000 mg/m3/2 h |
| Explosive hazard characteristics | It can be exploded when mixed with air; it can form explosive peroxide in 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 | dry powder, dry sand, carbon dioxide, foam |
| occupational standard | TWA 590 mg/m3; STEL 640 mg/m3 |
| auto-ignition temperature | 610 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-threatening and health concentration | 2,000 ppm [10% LEL] |
Last Update：2024-06-07 11:19:36
1,2,3,4-tetrahydro-9H-fluoren-9-one - Harm to human body
Tetrahydrofuran, also known as THF, is an organic compound commonly used as a solvent, cleaning agent, and in plastic production. Prolonged and excessive exposure to tetrahydrofuran can pose hazards to the human body, including:
1. Skin irritation and allergic reactions: Tetrahydrofuran may cause skin irritation, pain, redness, and allergic reactions.
2. Respiratory irritation: Inhaling the odor of tetrahydrofuran can lead to respiratory irritation, throat discomfort, headache, and dizziness.
3. Toxicity: Long-term exposure to tetrahydrofuran can result in toxicity, manifesting as headaches, nausea, vomiting, central nervous system damage, and liver function abnormalities.
4. Impact on the reproductive system: Some studies suggest that tetrahydrofuran may have effects on the reproductive system, including impact on fetal development and reproductive function disorders.
Therefore, it is important to avoid prolonged contact with tetrahydrofuran, take necessary personal protective measures, ensure adequate ventilation, and use protective equipment to minimize the hazards to the human body. If any discomfort or symptoms occur, seek medical attention promptly and consult with a healthcare professional.
Last Update：2024-04-09 19:55:45
1,2,3,4-tetrahydro-9H-fluoren-9-one - Nature
Open Data Verified Data
a colorless liquid with an odor similar to that of hexyl ether. Soluble in water and most organic solvents. Vapor can form explosives with air, and can react with acid contact, fire, strong oxidant cause combustion risk, and potassium hydroxide, sodium hydroxide reaction.
Last Update：2024-01-02 23:10:35
1,2,3,4-tetrahydro-9H-fluoren-9-one - Preparation Method
Open Data Verified Data
obtained by hydrogenation of maleic anhydride or by hydrogenation of furan in the presence of a nickel catalyst.
Last Update：2022-01-01 09:24:38
1,2,3,4-tetrahydro-9H-fluoren-9-one - Use
Open Data Verified Data
tetrahydrofuran is an important organic synthesis raw materials and excellent solvent, tetrahydrofuran for many organic matter has good solubility, it can dissolve in addition to polyethylene, all organic compounds other than polypropylene and fluororesin, especially polyvinyl chloride, polyvinylidene chloride and butylaniline, are widely used as reactive solvents. As a common solvent, tetrahydrofuran has been widely used in surface coatings, protective coatings, inks, extractants and surface treatment of artificial leather. Tetrahydrofuran is an important raw material for the production of Polytetramethylene ether glycol (PTMEG), it is also a major solvent in the pharmaceutical industry. It is used as a solvent for natural and synthetic resins (especially vinyl resins), and is also used in the preparation of butadiene, adiponitrile, adipic acid, hexamethylene diamine, etc.
Last Update：2022-01-01 09:24:39
1,2,3,4-tetrahydro-9H-fluoren-9-one - Safety
Open Data Verified Data
toxic! Has an anesthetic effect. Inhalation caused upper respiratory tract irritation, Nausea, dizziness, Head Pain and central nervous system depression. The maximum allowable concentration in air is 200 x lo-6. Polymerization inhibitors are usually added to commercial products. Store in a cool, ventilated warehouse. Keep away from fire and heat source. Protection from direct sunlight. Packaging is required to be sealed and not to be in contact with air. Should be stored separately from the oxidant, acid, alkali.
Last Update：2022-01-01 09:24:39
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