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四氢呋喃
四氢呋喃 · 无水四氢呋喃 · 超干四氢呋喃 · 超干THF · 无水THF · 氧杂环戊烷 · 四氢呋喃(THF) · 四氫呋喃
标识与物理属性
| CAS No. | 109-99-9 |
|---|---|
| 分子式 | C4H8O |
| 平均分子量 | 72.11 g/mol |
| 单同位素质量 | 72.05751487 g/mol |
| SMILES | C1CCOC1 |
| InChIKey | WYURNTSHIVDZCO-UHFFFAOYSA-N |
| PubChem CID | 8028 |
| ChEMBL | CHEMBL276521 |
| ChEBI | CHEBI:26911 |
| EC No. | 203-726-8 |
| DTXSID | DTXSID1021328 |
| 中文名 | 四氢呋喃 |
化学与物理性质
| XLogP | 0.5 |
|---|---|
| 极性表面积 | 9.2 |
| 氢键供体 | 0 |
| 氢键受体 | 1 |
| 可旋转键 | 0 |
| 重原子 | 5 |
| 形式电荷 | 0 |
| 复杂度 | 22 |
| LogP（油水分配系数） | log Kow = 0.460.46 (estimated) |
| 气味 | Ether-like odorFAINT FRUITY ODOREthereal, detectable at 2 to 50 ppm |
| 味道 | PUNGENT TASTE |
| 密度 | 0.888 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8833 g/cu cm at 25 °CSaturated liquid density: 55.230 lb/cu ftsaturated vapor pressure: 2.913 lb/sq insaturated vapor density: 0.03660 lb/cu ft (all at 75 °F)Relative density (water = 1): 0.890.8833 @25 °C0.887 g/mL at 20 °C |
| Viscosity | 0.53 cP at 20 °C0.5 mPa*s at 20 °C |
| Color/Form | Colorless, mobile liquidWater-white liquidColorless liquid |
| 溶解性 | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)Miscible with alcohols, ketones, esters, hydrocarbons, and ethers.Very soluble in acetone, benzene, ether, ethanol, and chloroform30% IN WATER AT 25 °CMiscible in water at 25 °C1000.0 mg/mLwater: soluble |
| Corrosivity | Tetrahydrofuran will attack some forms of plastics, rubber, and coatings. |
| 闪点 | 6 °F (NTP, 1992)-14 °C6 °F (closed cup)-4 °F (open cup)-14.5 °C (closed cup)-14.5 °C c.c.>230 °F |
| 沸点 | 151 °F at 760 mmHg (NTP, 1992)65 °C65.00 °C. @ 760.00 mm Hg66 °C65 °C @760 [mm Hg] |
| Decomposition | When heated to decomposition it emits acrid smoke & irritating fumes.Upon contact with air, THF may decompose into explosive peroxides & carbon monoxide. |
| 熔点 | -163.3 °F (NTP, 1992)-108.44 °C-108.3 °C-108.5 °C-108°C |
| 蒸气密度 | 2.5 (vs air) |
| 蒸气压 | <0.01 mm Hg ( 25 °C) |
| 折射率 | n20/D 1.465 |
| 储存条件 | Store at +5°C to +30°C. |
| 形态 | Liquid |
| 比重 | 0.89 |
| 颜色 | <10(APHA) |
| 相对极性 | 0.207 |
| pH | 7-8 (200g/l, H2O, 20℃) |
| 酸碱指示剂变色ph值范围 | 7 |
| 爆炸极限 | 1.5-12.4%(V) |
| 比热容 | Cp(liquid): 1.72 J/(g·K)Cp(gas): 1.06 J/(g·K), at 25℃ |
| 凝固点 | -108℃ |
| 热导率 | 0.145 W/(m·K) at 25 ℃ |
| 敏感性 | Air Sensitive & Hygroscopic |
| 最大波长(λmax) | λ: 245 nm Amax: ≤0.26λ: 275 nm Amax: ≤0.046λ: 315 μm Amax: ≤0.0044 |
| Merck | 14,9211 |
| BRN | 102391 |
| 亨利常数 | 1.54 (static headspace-GC, Welke et al., 1998) |
| 暴露限值 | ACGIH:TLV-TWA 50 ppm (147 mg/m3)TLV-STEL 100 ppm (295 mg/m3)OSHA:PEL-TWA 200 ppm (590 mg/m3)NIOSH:REL-TWA 200 ppmREL-STEL 250 ppm |
| 介电常数 | 11.6(-70℃) |
| 稳定性 | 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. Store at room temperature under nitrogen. Hazardous polymerisation may occur. Light sensitive. May contain 2,6-di-tertbutyl-4-methylphenol (BHT) as a stabilizer. |
| InChI | 1S/C4H8O/c1-2-4-5-3-1/h1-4H2 |
| InChIKey | WYURNTSHIVDZCO-UHFFFAOYSA-N |
| SMILES | C1CCOC1 |
| LogP（油水分配系数） | 0.45 at 25℃ |
| 表面张力 | 27.31mN/m at 293.15K |
| CAS 数据库 | 109-99-9(CAS DataBase Reference) |
| NIST化学物质信息 | Furan, tetrahydro-(109-99-9) |
| (IARC)致癌物分类 | 2B (Vol. 119) 2019 |
| EPA化学物质信息 | Tetrahydrofuran (109-99-9) |
| Absorption | ≤0.0044 at 315nm≤0.005 at 350nm≤0.005 at 400nm≤0.02 at 300nm≤0.046 at 275nm≤0.18 at 250nm≤0.26 at 245nm≤1.0 at 212nm |
化学性质
无色透明液体，有乙醚气味。 与水、醇、酮、苯、酯、醚、烃类混溶。
安全与法规
| GHS 分类 | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H351: Suspected of causing cancer [Warning Carcinogenicity]P203, P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P318, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.1% (2 of 1661) of reports. |
|---|---|
| 法规信息 | Chemical: Furan, tetrahydro-Hazard Traits - CarcinogenicityEnvironmental toxNeurotoxicityAuthoritative List - CWA 303(d)IARC Carcinogens - 2BIRIS NeurotoxicantsProp 65Report - regardless of intended function of ingredient in the productFuran, tetrahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Furan, tetrahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 30-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15474Status: Active Update: 16-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22931Furan, tetrahydro-: HSNO Approval: HSR001224 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 其他安全信息 | IMAP assessments - Furan, tetrahydro-: Human health tier III assessmentIMAP assessments - Furan, tetrahydro-: Human health tier II assessment |
| 运输标签（DOT） | Flammable Liquid |
| 火灾危害 | Special Hazards of Combustion Products: Irritating vapor is generated when heated.Behavior in Fire: May explode. Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.CAUTION: Ethanol (UN1170) can burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.)· Vapors may form explosive mixtures with air.· Vapors may travel to source of ignition and flash back.· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).· Vapor explosion hazard indoors, outdoors or in sewers.· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.· Runoff to sewer may create fire or explosion hazard.· Containers may explode when heated.· Many liquids will float on water.Highly flammable. Vapour/air mixtures are explosive. |
| 火灾可能性 | Flammable liquid. A very dangerous fire hazard when exposed to heat, flames, oxidizers. |
| 健康危害 | Vapors cause nausea, dizziness, headache, and anesthesia. Liquid can de-fat the skin and cause irritation. Liquid also irritates eyes. (USCG, 1999)· Inhalation or contact with material may irritate or burn skin and eyes.· Fire may produce irritating, corrosive and/or toxic gases.· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.· Runoff from fire control or dilution water may cause environmental contamination. |
| 危害概述 | Anesthesia produced in animal inhalation studiesToxic hepatitis has been reported in exposed workers. TLV Basis is irritation, CNS impairment, and kidney damage. [ACGIH] A skin, eye, and respiratory tract irritantInhalation of high concentrations can cause CNS depression[ICSC]Tetrahydrofuran (THF) is a very hazardous substance due primarily to its flammable and explosive properties. Toxicity is also of concern and must be considered in the safe handling and storage of THF. Irritation from dermal contact with THF warrants the wearing of gloves and safety glasses for protection during the routine handling of this substance. Toxic, as well as flammable, concentrations of THF in air can be avoided by compliance with the TLV of 200 ppm. When this TLV is exceeded, respiratory protection is needed. Protection above the TLV of 50 ppm up to 500 ppm can be provided by a respirator mask using an approved organic vapor cartridge. For emergency situations, such as fires or involving exposure above 500 ppm, a self-contained breathing apparatus would be needed. THF is highly volatile with a low flash point (1 °F) and flammability limit of 2%. Its heavier-than-air vapors can travel at low profile for considerable distances and flash back to the point of origin. Further, unstabilized THF forms peroxides upon exposure to air or light, which, if allowed to accumulate above 1% become thermally explosive. THF also reacts explosively with lithium-aluminum alloys. In consideration of the above, THF should be contained in tightly sealed dark glass bottles or steel drums affixed with the DOT-required label, "Flammable Liquid". Should THF leak from containment vessels, its faint, fruity smell, is detectable at 50 ppm and may serve as a warning. Containers should be stored in cool, dark, well-ventilated areas, away from ignition sources and oxidizing materials. Should a THF fire occur, it may be combated with dry chemical or CO2 extinguishers. Water may be ineffective in firefighting. However, if a leak or spill has not ignited, it may be flushed with water for cooling and diluting if conditions of ignition threaten. Knock down vapors with water spray. Spills or leaks should be absorbed with paper or dissolved in petroleum ether or alcohol (of a higher molecular w |
| 运输编号与指南（DOT） | 2056 127 |
| FDA 要求 | Tetrahydrofuran is an indirect food additive for use only as a component of adhesives. |
| 反应性基团 | Ethers |
| 联合国分类 | UN Hazard Class: 3UN Pack Group: II |
| Special Reports | Health & Safety ExecutiveCriteria Document Summaries-Synopses of the Data Used in Setting Occupational Exposure Limits. HSE Books, PO Box 1999, Sudbury, Suffolk, UK C010 6FS (1995) This document contains summaries of the data considered by the Health and Safety Commission of the United Kingdom in setting occupational exposure standards. ...European CommissionOccupational Exposure Limits. Recommendations of the Scientific Expert Group 1991-1992. Office for Official Publications of the European Communities, 2985 Luxembourg. 85pp. (1994). This document contains recommendations of the Scientific Advisory Group for a series of 26 substances ... /which include/ ... proposed occupational exposure limits. ...Toxicology & Carcinogenesis Studies of Tetrahydrofuran in F344/N Rats and B6C3F1 Mice p.6 Technical Report Series No. 475 (1998) NIH Publication No. 98-3965 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709 |
| 消防 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For fire involving UN1170, UN1987 or UN3475, alcohol-resistant foam should be used. CAUTION: Ethanol (UN1170) can burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.).SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam.LARGE FIRE: Water spray, fog or alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzlesif this is impossible, withdraw from area and let fire burn. (ERG, 2024)Use alcohol-resistant foam, water spray, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| 急救措施 | Fresh air, rest. Refer immediately for medical attention.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.Rinse mouth. Refer for medical attention . |
| 泄漏应急措施 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· Keep unauthorized personnel away.· Stay upwind, uphill and/or upstream.· Ventilate closed spaces before entering, but only if properly trained and equipped.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.· All equipment used when handling the product must be grounded.· Do not touch or walk through spilled material.· Stop leak if you can do it without risk.· Prevent entry into waterways, sewers, basements or confined areas.· A vapor-suppressing foam may be used to reduce vapors.· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.· Use clean, non-sparking tools to collect absorbed material.Large Spill· Dike far ahead of liquid spill for later disposal.· Water spray may reduce vapor, but may not prevent ignition in closed spaces. |
| 急救 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)General First Aid:· Call 911 or emergency medical service.· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.· Move victim to fresh air if it can be done safely.· Administer oxygen if breathing is difficult.· If victim is not breathing:-- DO NOT perform mouth-to-mouth resuscitationthe victim may have ingested or inhaled the substance.-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.· Remove and isolate contaminated clothing and shoes.· For minor skin contact, avoid spreading material on unaffected skin.· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.· For severe burns, immediate medical attention is required.· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.· Keep victim calm and warm.· Keep victim under observation.· For further assistance, contact your local Poison Control Center.· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.Specific First Aid:· Wash skin with soap and water.(General first aid procedures)Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.Skin: Water flush promptly - If this chemical contacts the skin, flush the contaminated skin with water promptly. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water promptly. If irritation persists after washing, get medical attention.Breathing: Respiratory supportSwallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately. |
| 安全储存 | Fireproof. Well closed. Separated from : see Chemical Dangers. |
| Firefighting Hazards | Tetrahydrofuran (THF) is extremely flammable (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." A 5% solution of THF in water is flammable.Vapor is heavier than air and may travel considerable distance to source of ignition and flash back. |
| 暴露控制与个人防护 | · Wear positive pressure self-contained breathing apparatus (SCBA).· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.Biological Exposure Indices (BEI) [ACGIH] - Tetrahydrofuran in urine = 2 mg/Lsample at end of shift20.34 [ppm] |
| 灭火程序 | Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.Closed containers may rupture violently when heated.Wear full protective clothing and positive pressure self-contained breathing apparatus. Teflon barrier recommended. |
| 储存条件 | Store in a cool, dry, well-ventilated location. Store away from heat, oxidizing materials, and sunlight. Outside or detached storage is preferred. Inside storage should be in a standard flammable liquids storage warehouse, room, or cabinet.Purified tetrahydrofuran should not be stored for more than a few months after its container has been opened if it contains no oxidation inhibitor. In this case, it is potentially explosive because of peroxide formation.NO open flames, NO sparks, and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT use compressed air for filling, discharging, or handling.Distillation or alkali treatment of stabilized tetrahyrofuran removes the involatile anti-oxidant, and the solvent must be restabilized or stored under nitrogen to prevent formation during storage, which should not exceed a few days duration in the absence of stabilizer.THF can be stored in the usual steel containers. |
| 清理方法 | Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations.Shut off all possible sources of ignition. Instruct others to maintain a safe distance. Wear breathing apparatus, eye protection, laboratory coat, and butyl rubber gloves. Cover with a 1:1:1 mixture by weight of sodium carbonate or calcium carbonate, clay cat litter (bentonite), and sand. Transfer to a large dish and let evaporate in fume hood. Ventilate area well to evaporate remaining liquid and dispel vapor. Treat solid residue as normal refuse.Absorb with paper. Evaporate completely all spilled surface. Dispose by burning the paper after complete ventilation of vapor. |
| 非火灾泄漏应对 | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024) |
| 处置方法 | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U213, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A good candidate for liquid injection incineration at a temperture range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. Also, a good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. Also, a good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.Tetrahydrofuran is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. In controlled waste containing peroxides, perforation of a container of the waste form a safe distance is followed by open burning./In laboratories/ excess tetrahydrofuran and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.For more Disposal Methods (Complete) data for Tetrahydrofuran (6 total), please visit the HSDB record page. |
| 体内负荷 | In 4 urban areas, tetrahydrofuran was detected in Mother's milk in 1 of 12 samples(1). |
| 靶器官 | DevelopmentalHepaticNervousEyes, respiratory system, central nervous system |
| 生态毒性数值 | LC50Species: Daphnia magna (Water flea, age < or = 24 hr)Conditions: freshwater, static, 20-22 °C, pH 7.6-7.7Concentration: >10,000,000 ug/L for 24 hr /formulated product/Species: Daphnia magna Straus (water flea)Concentration: 5930 mg/L for 24 hrConditions: DIN 38412 Section 11Species: Moina macrocopa (water flea)Concentration: 9800 mg/L for 3 hr /Conditions of bioassay not given/Species: Carassius auratus (goldfish)Concentration: 2400 mg/L for 48 hrConditions: staticFor more Ecotoxicity Values (Complete) data for Tetrahydrofuran (9 total), please visit the HSDB record page. |
| 环境归趋 | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 18 and 23(2), indicate that tetrahydrofuran is expected to have very high mobility in soil(SRC). Volatilization of tetrahydrofuran from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 7.05X10-5 atm-cu m/mole(3). Tetrahydrofuran is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 162 mm Hg at 25 °C(4). Tetrahydrofuran, added to the surface of 2 different soil samples which had been sterilized to prevent microbial degradation, had a disappearance half-life of 5.7 days(5). A 100% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in soil(SRC)however, the EEC manometric respirometric method, tested in 22 different laboratories, gave a mean of 34% of the theoretical BOD within 28 days(7).AQUATIC FATE: Based on a classification scheme(1), Koc values of 18 and 23(2), indicate that tetrahydrofuran is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 7.05X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 13 hours and 6.6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.46(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In the modified MITI screening test, tetrahydrofuran at 100 mg/L was completely biodegraded in 14 days using an activated sludge inoculum(8)however, the EEC manometric respirometric method, tested in 22 different laboratories, gave a mean of 34% of the theoretical BOD within 28 days(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetrahydrofuran, which has a vapor pressure of 162 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tetrahydrofuran is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is 21 to 24 hours(3), calculated from its measured rate constants of 1.62X10-11 to 1.8X10-11 cu cm/molecule-sec(4). Butyrolactone and alpha-hydroxytetrahydrofuran were formed as products during the photooxidation of tetrahydrofuran(5). Tetrahydrofuran will also react with nitrate radicalsthe half-life for this reaction in air is 3 days(SRC), calculated from its measured rate constant of 4.88X10-15 cu cm/molecule-sec(6). Tetrahydrofuran is moderately reactive in photochemical smog conditions where nitrogen oxides are presentreactions occur in time scales of hours(7-9). |
| 食品调查数值 | Tetrahydrofuran has been identified in coffee aroma.Constituent of roasted coffeeTetrahydrofuran was detected as a volatile compound, isolated from floured chickpea seed(1). This compound was identified in the volatile component of cooked chicken(2). |
| 不良影响 | Neurotoxin - Acute solvent syndromeOccupational hepatotoxin - Primary hepatotoxins: the toxic effect to the liver is the principal adverse effect of the chemical.Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.ACGIH Carcinogen - Confirmed Animal. |
| 暴露途径 | The substance can be absorbed into the body by inhalation of its vapour, by ingestion and through the skin.inhalation, skin and/or eye contact, ingestion |
| Milk Concentrations | ENVIRONMENTAL: In 4 urban areas, tetrahydrofuran was detected in Mother's milk in 1 of 12 samples(1). |
| 毒性概述 | HUMAN TOXICITY: Data pertaining to the toxicity of tetrahydrofuran (THF) in humans is quite limited. The probable oral lethal dose in humans is 50-500 mg/kg. Severe occipital headaches were reported in the testing for pharmacological properties of THF & among technicians performing animal experiments. Toxicity (TCLo) is expected following exposure to a 2.5% concn of THF. ANIMAL TOXICITY: Animal studies indicate that THF is only "MODERATELY TOXIC" from acute exposure with the lowest reported LD50's of 1900-2900 mg/kg by oral route. Median lethal concns by inhalation varied with the duration of exposure but were >20,000 ppm with all species for exposures of 1 hr or less. Reports of animal studies document irritation of the skin & mucous membranes, including the eyes, nose, & upper respiratory tract, as the predominant effect from lower exposures (about 100-200 ppm). High acute doses (about 25,000 ppm) produced anesthesia with delayed induction & recovery periods, accompanied by a fall in blood pressure & strong respiratory stimulation. The margin of safety between anesthesia & death is small. Other effects recorded are those of damage to liver, kidneys, & lung after prolonged exposures to levels of THF >1000 ppm. Toxic manifestations varied somewhat with the route of exposure with irritation of upper respiratory tract observed with inhaled THF & inflammation of the GI tract following oral ingestion. The only report on carcinogenicity is that of a test for skin tumors in which THF was applied to the skin of mice twice/wk for 25 exposures with an observation period of 17.5 months. No carcinogenic effect was observed. THF was negative when tested for mutagenicity using the Ames testhowever, it would appear to enhance the mutagenicity of certain tryptophan-pyrolysate substances. No information is presented on metabolism, absorption, & distribution. The only report on excretion is the finding of THF in mother's milk. |
| Signs and Symptoms | Cough. Burning sensation in the throat and chest. Dizziness. Headache. Nausea. Unconsciousness.Dry skin. Redness. Pain.See Inhalation.irritation eyes, upper respiratory systemnausea, dizziness, headache, central nervous system depression |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=109-99-9] |
| Effluent Concentrations | Thirty samples taken between 1973-1976 ranged from 0 ug/L (Olin Corp, Brandenbury, KY, Ohio River/Wabash River) to 450,000 ug/L (General Electric, Mt Vernon, IN, Ohio River). Other notably high concentration were 1000 ug/L (M/T Chem, Carrloton, KY, Ohio River), 850 ug/L (Olin Corp, IN, Ohio River/ Wabash River), and 318 ug/L (Ashtabula, OH).Leachate from the Rochester Municipal Landfill contained tetrahydrofuran at 0.43 mg/L(1). Effluent samples taken from a plant that finished polyester fabrics contained tetrahydrofuran at unreported concentrations(2). Tetrahydrofuran was reported in the vehicle exhaust gases from a gasoline engine at unreported concentrations(3). Effluent from a sewage treatment plant in Barceloneta, Puerto Rico, receiving waste from several pharmaceutical industries contained tetrahydrofuran at unreported concentrations(4). Ambient air samples from 2 of 5 hazardous waste sites in New Jersey contained tetrahydrofuran at unreported concentrations(5).Tetrahydrofuran was detected in 20 of 1043 common household products at unreported concentrations(1). Tetrahydrofuran was identified but not quantified as a volatile organic compound released from textile floor coverings(2). Tetrahydrofuran was identified as a major constituent of polyvinyl chloride primer and adhesive and was found to be leached into the water surrounding bonded joints at concentrations ranging from 215-63,000 ug/L (concentrations given for the first wash for 7 different products)(3)6 and 8 months following polyvinyl chloride pipe installation tetrahydrofuran concentrations in the surrounding water were 13 and 7.5 ppm, respectively(4). Volatile organic compounds measured from a sludge landfill simulator contained tetrahydrofuran at unreported concentrations(5). The concentration of tetrahydrofuran in landfill leachate ranges from 18 to 1,400 ug/L(6). Groundwater sampled under two waste disposal sites in Minnesota contained tetrahydrofuran at concentrations from 24-3900 ug/L(7). Leachates from 3 of 5 landfill sites in Connecticut contained tetrahydrofuranCheshire site at 60 ug/L, Norwich site at 20 ug/L, Danbury site at 330 ug/L(8). |
| RCRA 要求 | U213As stipulated in 40 CFR 261.33, when tetrahydrofuran, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| TSCA 要求 | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 3/11/94Reporting date: 5/10/95.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Tetrahydrofuran is included on this list. Effective date 3/11/94Sunset date: 6/30/98.A testing consent order is in effect for tetrahydrofuran for health effects testing. FR citation: 1/23/95. |
| CERCLA 应报告数量 | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b). |
| 州饮用水指南 | (MA) MASSACHUSETTS 600 ug/L(NH) NEW HAMPSHIRE 150 ug/L(WI) WISCONSIN 50 ug/L(ME) MAINE 70 ug/L(FL) FLORIDA 4.6 ug/L |
| F | 3-10-23 |
| 水危害等级（WGK） | 1 |
| TSCA 清单状态 | TSCA listed |
| 毒性 | 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) |
| RTECS 号 | MD0916000 |
| 包装类别 | II |
| 危险类别 | 3Acute Tox. 4 OralCarc. 2Eye Irrit. 2Flam. Liq. 2STOT SE 3 |
| 储存类别 | 3 - Flammable liquids |
| 安全说明（S） | 26-36-33-29-16-46-37-13 |
| 海关编码 | 29321100 |
| 自燃温度 | 610 °F |
| 危险品标志 | Xi,F,Xn |
| 危险类别码（R） | 36/37/38-36/37-19-11-40 |
| 毒害物质数据 | 109-99-9(Hazardous Substances Data) |
| 职业暴露等级（OEB） | A |
| 职业暴露限值（OEL） | TWA: 200 ppm (590 mg/m3), STEL: 250 ppm (735 mg/m3) |
| 运输编号（UN） | UN 2056 |
| 立即危及生命和健康浓度 | 2,000 ppm [10% LEL] |
急性毒性
口服-大鼠LD50:1650毫克/公斤; 吸入-小鼠LCL0: 24000毫克/立方米/2小时
职业标准
TWA 590 毫克/立方米; STEL 640 毫克/立方米
爆炸物危险特性
与空气混合可爆; 在空气中能形成可爆的过氧化物
可燃性危险特性
遇明火、高温、氧化剂易燃; 燃烧产生刺激烟雾
储运特性
库房通风低温干燥; 与氧化剂、酸碱类分开存放
灭火剂
干粉、干砂、二氧化碳、泡沫
用途与应用
概述
四氢呋喃，英文缩写为THF，是一个杂环有机化合物。属于醚类，是芳香族化合物呋喃的完全氢化产物。 四氢呋喃是最强的极性醚类之一，在化学反应和萃取时用做一种中等极性的溶剂，常温下为无色易挥发液体，有类似乙醚的气味。溶于水、乙醇、乙醚、丙酮、苯等多数有机溶剂，被称为“万能溶剂”。室温下与水能部分混溶，部分不法试剂商就是利用这一点对四氢呋喃试剂兑水牟取暴利。由于THF在贮存中有形成过氧化物的趋势，工业品一般加抗氧剂BHT。水分含量≦0.2%。具有低毒、低沸点、流动性好的特点。 目前，国内的四氢呋喃主要生产商包括巴斯夫中国、大连仪征（DCJ）、山西三维、中化国际、中石油前郭炼油厂等，另外一些PBT工厂也副产一部分。 美国LyondellBasell工业公司在美国和欧洲的四氢呋喃销售指标为：纯度99.90%，色度（APHA）10，水分0.03%，THF氢过氧化物0.005%，杂质总量0.05%，氧化抑制剂0.025%～0.035%。 在聚氨酯行业中最主要的用途是作为聚四氢呋喃二醇（PTMEG）的单体原料，这也是THF的主要用途之一。
用途
氨基酸和肽的纸层析。溶剂。有机合成。高效液相色谱,紫外发光光度分析。
用途
四氢呋喃又名一氧五环、氧杂环戊烷、四亚甲基氧，是合成农药苯丁锡的中间体，另外，可直接用于制合成纤维、合成树脂、合成橡胶，也是许多聚合材料、精密磁带和电镀工业的溶剂，还用于制己二腈、己二酸、己二胺、丁二酸、丁二醇、γ-丁内酯等，在医药工业上，可用于生产咳必清、黄体酮、利复霉素和用作制药溶剂等。
制备与合成方法
生产方法
工业生产最早以糖醛为原料，将糖醛与蒸气的混合物通入填充锌-铬-锰金属氧化物（或钯）催化剂的反应器，于400-420℃脱去羰基而成呋喃；然后以骨架镍为催化剂，于80-120℃呋喃加氢制得四氢呋喃。该法生产1吨四氢呋喃，约需消耗3吨多糖醛。后来发展的生产方法有许多种，工业化的方法有1,4-丁二醇催化脱水环合法，因为丁二醇是由乙炔和甲醛制得的，此法称雷由法（Reppe法）；利用氯丁橡胶单体氯丁二烯的副产物1,4-二氯丁烯生产四氢呋喃，称为二氯丁烯法；近年来发展了以顺酐为原料的催化加氢法。
生产方法
四氢呋喃的生产工艺有以下5种。(1)糠醛法由糠醛脱羰基生成呋喃，再加氢而得。这是工业上最早生产四氢呋喃的方法之一。糠醛主要由玉米芯等农副产品水解制造。该法污染严重，不利于大规模生产，已逐步被淘汰。(2)顺酐催化加氢法顺酐和氢气从底部进入内装镍催化剂的反应器，产物中四氢呋喃与γ-丁内酯比例可通过调整操作参数加以控制。反应产物与原料氢气冷却至50℃左右进入洗涤塔底部，使未反应的氢气及气态与液态产物分离，未反应的氢气及气态产物经洗涤后循环到反应器，液态产物经蒸馏而得四氢呋喃产品。该工艺可在0～(5∶1)范围内任意调整γ-丁内酯与四氢呋喃的比例，顺酐的单程转化率达100%，四氢呋喃选择性为85％～95％，产品含量达99.97%。该工艺具有催化剂性能好、流程简单、投资少等特点。(3)1，4-丁二醇脱水环化法其工艺过程为：向反应器中加入1087kg 22%的硫酸水溶液，在100℃以110kg/h的速度加入1，4-丁二醇，塔顶温度维持在80℃，以大约110kg/h的速度从塔顶得到含有80%四氢呋喃的水溶液。加入50t 1，4-丁二醇后，从反应器中排除约70kg焦质。将焦质进行过滤，得到的硫酸水溶液可以重新使用，这一过程的四氢呋喃收率可以达到99％以上。硫酸是四氢呋喃工业生产中使用最早的催化剂，也是现今生产中应用较多的催化剂。此工艺技术成熟，工艺比较简单，反应温度较低，四氢呋喃收率较高，但硫酸易腐蚀设备，污染环境。(4)二氯丁烯法以1，4-二氯丁烯为原料，经水解生成丁烯二醇，再经催化加氢而得。1，4-二氯丁烯在氢氧化钠溶液中水解，110℃下生成丁烯二醇，离心分离去掉氯化钠，滤液在蒸发结晶器中浓缩，分离出碱金属羧酸盐，再在蒸馏塔中除去高沸物。将精制后的丁烯二醇送入反应器，以镍为催化剂，在80～120℃及一定压力下，丁烯二醇加氢生成丁二醇，蒸馏后进人环合反应器，在常压及120～140℃下于酸性介质中生成粗四氢呋喃，蒸馏脱水和脱高沸物，最后蒸馏得高纯四氢呋喃。此法操作简便，条件温和，收率高，催化剂用量少，可连续使用。(5)丁二烯氧化法以丁二烯为原料，经氧化得呋喃，再加氢而得。此法在国外已工业化。