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Furfuryl alcohol ( CASNO:98-00-0 )
Identification and Related Records
- Furfuryl alcohol
- CAS Registry number:
- 2-Furan methanol
2-Furfuryl Alcohol (FA)
- Molecular Formula:
- Molecular Weight:
- Canonical SMILES:
Chemical and Physical Properties
- clear yellow liquid
- Melting Point:
- Boiling Point:
- Refractive Index:
- Flash Point:
- Water Solubility : MISCIBLE
- Colorless to yellow liquid
Colorless, mobile liquid (becomes brown to dark-red on exposure to light and air)
- Storage temp:
- Spectral properties:
- MAX ABSORPTION (WATER): 217 NM (LOG E= 3.9)
Index of refraction = 1.4869 at 20 deg C
IR: 10765 (Sadtler Research Laboratories IR Grating Collection)
UV: 45 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 102 (Varian Associates NMR Spectra Catalogue)
MASS: 68580 (NIST/EPA/MSDC Mass Spectral Database 1990 version); 745 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
- Computed Properties:
- Molecular Weight:98.09994 [g/mol]
Rotatable Bond Count:1
Topological Polar Surface Area:33.4
Heavy Atom Count:7
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:4
Safety and Handling
- Hazard Codes:
- Risk Statements:
- Safety Statements:
- Hazard Codes:?Xn
Risk Statements: 20/21/22?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 23-36/37/39?
S23: Do not breathe vapour
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2874 6.1/PG 3
WGK Germany: 1
- Skin, Eye, and Respiratory Irritations:
- The material is markedly irritating & injurious to the eyes.
- UN 2874
- Fire Fighting Procedures:
- To fight fire use alcohol foam, carbon dioxide, dry chemical ... .
- Fire Potential:
- Moderate, when exposed to heat; can react with oxidizing materials.
- Grade: Technical, refined.
- DOT Emergency Guidelines:
- /GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. 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 engulfed in fire.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
- Exposure Standards and Regulations:
- Furfuryl alcohol is an indirect food additive for use only as a component of adhesives.
- Reactivities and Incompatibilities:
- Strong oxidizers & acids [Note: Contact with organic acids may lead to polymerization].
An explosion occurred in a laboratory when cyanoacetic acid was reacted with furfuryl alcohol in an attempt to form the ester, furfuryl cyanoacetate. The explosion occurred a few minutes after the agitator was turned on and the heat applied.
During an attempt to prepare furfuryl formate from furfuryl alcohol and concentrated formic acid, an explosion occurred.
Furfuryl alcohol will polymerize rapidly, and sometimes with explosive violence, in the presence of strong mineral acids.
Furfuryl alcohol is ignited immediately by concentrated nitric acid.
Combinations of unsymmetrical dimethylhydrazine, aniline, or furfuryl alcohol as fuels with hydrogen peroxide or a mixture of nitric acid-nitrogen tetroxide-sulfuric acid as oxidizers ignite with little delay and are used as propellants.
Mixture of fuming nitric acid and ... /furfuryl alcohol is/ self-igniting ...
Homogeneous mixtures of concentrated peroxide with alcohols or other peroxide-miscible organic liquids are capable of detonation by shock or heat. Furfuryl alcohol ignites in contact with 85% peroxide within 1 sec.
Reaction of sulfur tetrafluoride with 2-hydroxymethylfuran in presence of triethylamine at -50 deg C is explosive in absence of a solvent.
Hypergolic with fuming nitric acid.
- Other Preventative Measures:
- The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The explosion hazards associated with the use of acidic catalysts to polymerize furfuryl alcohol may be avoided by using as catalyst the condensation product of 1,3-phenylenediamine and 1-chloro-2,3-epoxypropane.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
- Protective Equipment and Clothing:
- Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Respirator Recommendations : Up to 75 ppm: (Assigned Protection Factor = 10) Any chemical cartridge respirator with organic vapor cartridge(s). Substance reported to cause eye irritation or damage; may require eye protection./(Assigned Protection Factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister./(Assigned Protection Factor = 25) Any powered, air-purifying respirator with organic vapor cartridge(s). Substance reported to cause eye irritation or damage; may require eye protection./(Assigned Protection Factor = 10) Any supplied-air respirator. Substance reported to cause eye irritation or damage; may require eye protection./(Assigned Protection Factor = 50) Any self-contained breathing apparatus with a full facepiece.
Respirator Recommendations : Emergency or planned entry into unknown concentrations or IDLH conditions: (Assigned Protection Factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode./(Assigned Protection Factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations : Escape: (Assigned Protection Factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.
- ?Furfuryl alcohol?(CAS NO.98-00-0) is also called as 2-Furancarbinol ; 2-Furanmethanol ;?2-Furfuryl alcohol ;?2-Furfurylalkohol [Czech] ; 2-Furylcarbinol?; 5-Hydroxymethylfuran?;?2-Hydroxymethylfuran?;?Furfuranol ; Furfurylcarb ;?Furylcarbinol (VAN) ;?Methanol, (2-furyl)- ;?alpha-Furylcarbinol .?Furfuryl alcohol is an organic compound containing a furan substitited with a hydroxymethyl group. It is a clear amber liquid with a faint burning odor and a bitter taste. It is soluble in common organic solvents. Upon treatment with acids, heat and/or catalysts,?? furfuryl alcohol can be made to polymerize into a resin, poly .
- Octanol/Water Partition Coefficient:
- log Kow= 0.28
- Disposal Methods:
- SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incineration in a mixture with a more flammable solvent. Recommendable method: Incineration. Not recommendable method: Evaporation.
Use and Manufacturing
- Use and Manufacturing:
- Methods of Manufacturing
US 2041184 (to Quaker Oats)
Continuous vapor-phase hydrogenation of furfural.
By the catalytic reduction of furfural using nickel and copper chromium oxide catalysts.U.S. Production
This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
(1974) 2.4X10+10 GRAMS
(1986) >50 million-100 million pounds
(1990) >50 million-100 million pounds
(1994) >10 million-50 million pounds
(1998) >10 million-50 million pounds
(2002) >10 million-50 million poundsConsumption Patterns
CLOSE TO 100% AS A REACTANT IN FURAN RESIN PRODUCTION (1974)
- Sampling Procedures:
- FURFURYL ALCOHOL HAS BEEN COLLECTED FROM AIR BY PASSING IT THROUGH GLACIAL ACETIC ACID.
Biomedical Effects and Toxicity
- Biomedical Effects and Toxicity:
- ... /Investigators/ suggest that furfuryl alcohol is distributed equally through most or all of the body water ... though it appears to have a slight predilection for the brain.
When [C14] furfuryl alcohol at doses up to 27.5 mg/kg bw ... were administered to rats by gavage in corn oil, 83-89% of the radiolabel was excreted in the urine and 2-4% in the feces, and 7% was exhaled as C14-carbon dioxide within 24 hours. Residual radiolabel was distributed primarily to the liver and kidneys, the amount generally being proportional to the dose.
The urine appeared to be the major route of elimination /in rats/ (up to 90%), followed by feces (2.0-4.0% and exhaled CO2 (7.0%).
The comparative metabolism and disposition of furfural (FAL) and furfuryl alcohol (FOL) /in male Fisher 344 rats/ were investigated following oral administration of approximately 0.001, 0.01, and 0.1 of the LD50, corresponding to approximately 0.127, 1.15, and 12.5 mg/kg for FAL and 0.275, 2.75, and 27.5 mg/kg for FOL. At all doses studied, at least 86-89% of the dose of FAL or FOL was absorbed from the gastrointestinal tract. FAL and FOL were extensively metabolized prior to excretion. The major route of excretion was in urine, where 83-88% of the dose was excreted, whereas 2-4% was excreted in the feces. Approximately 7% of the dose from rats treated with FAL at 12.5 mg/kg was exhaled as 14CO2. At 72 hr following administration, the pattern of tissue distribution of radioactivity was similar for both FAL and FOL. Liver and kidney contained the highest, and brain the lowest concentrations of radioactivity. Generally, the concentrations of radioactivity in tissues were proportional to the dose. Almost all of the urinary radioactivity was tentatively identified. No FAL or FOL was detected in urine. [Nomeir AA et al; Drug Metab Dispos 20 (2): 198-204 (1992)] PubMed Abstract
Environmental Fate and Exposure Potential
- Environmental Fate/Exposure Summary:
- TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.28(2) and a regression-derived equation(3), indicates that furfuryl alcohol is expected to have very high mobility in soil(SRC). The pKa of furfuryl alcohol is 9.55(4), indicating that this compound will primarily exist in its neutral form in the environment(5). Volatilization of furfuryl alcohol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.609 mm Hg(6), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(7). Furfuryl alcohol may volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). Furfuryl alcohol may be susceptible to biodegradation in terrestrial environments based on the observed degradation of 75-79% in 2 weeks(8) and 97% in 5 days (acclimated for 20 days)(9) in aerobic screening tests with activated sludge inoculum.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.28(2) and a regression-derived equation(3), indicates that furfuryl alcohol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.609 mm Hg(4), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(5). The pKa of furfuryl alcohol is 9.55(6), indicating that this compound will primarily exist in its neutral form in the environment(7). According to a classification scheme(8), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Furfuryl alcohol may be susceptible to biodegradation in aquatic environments based on the observed degradation of 75-79% in 2 weeks(10) and 97% in 5 days (acclimated for 20 days)(11) in aerobic screening tests with activated sludge inoculum.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), furfuryl alcohol, which has a vapor pressure of 0.609 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase furfuryl alcohol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.7 hours(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Furfuryl alcohol absorbs light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(5).
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