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Home > Encyclopedia > Furfuryl alcohol

Furfuryl alcohol

Furfuryl alcohol structure

Furfuryl alcohol 

structure
  • CAS No:

    98-00-0

  • Formula:

    C5H6O2

  • Chemical Name:

    Furfuryl alcohol

  • Synonyms:

    2-Furanmethanol;Furfuryl alcohol;2-Furancarbinol;Furfuralcohol;α-Furylcarbinol;2-Furylcarbinol;Furylcarbinol;2-Furfuryl alcohol;2-(Hydroxymethyl)furan;5-Hydroxymethylfuran;α-Furfuryl alcohol;2-Furylmethanol;2-Furanylmethanol;Chem-Rez 200;Furfuranol;NSC 8843;2-Furylmethyl alcohol;Chem-Rez Fury 454;1262335-14-7

  • Categories:

    Organic Chemistry  >  Alcohols, Phenols, Phenol Alcohols

Description

clear yellow liquid Furfural alcohol is a colorless to amber liquidthat darkens on exposure to light. It has a faint, burning odor. Furfuryl alcohol has a very mild, warm, oily, “burnt” odor and a cooked sugar taste.


Furfuryl alcohol appears as a clear colorless liquid. Flash point 167°F. Boiling point 171°F. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion and skin contact and moderately toxic by inhalation.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR. TURNS RED OR BROWN ON EXPOSURE TO LIGHT AND AIR.|Colourless or pale yellowish liquid, mild, warm oily, "burnt" odour|Colorless to amber liquid with a faint, burning odor.|Colorless to amber liquid with a faint, burning odor. [Note: Darkens on exposure to light.]


Furfuryl alcohol appears as a clear colorless liquid. Flash point 167°F. Boiling point 171°F. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion and skin contact and moderately toxic by inhalation.|Furfuryl alcohol is a furan bearing a hydroxymethyl substituent at the 2-position. It has a role as a Maillard reaction product. It is a primary alcohol and a member of furans.

Furfuryl alcohol Basic Attributes

98.09990

98.10

202-626-1

D582054MUH

0794

8843

2874

DTXSID2025347|DTXSID9049742

Colorless to yellow liquid|Colorless, mobile liquid (becomes brown to dark-red on exposure to light and air)

2932130000

Characteristics

33.37000

0.7719

Transparent yellow liquid

1.1296 g/cm3 @ Temp: 20 °C

-15 °C

171 °C @ Press: 750 Torr

149 °F

n20/D 1.486(lit.)

Miscible

Packing intact、handling with care,Warehouse ventilation、Keep away from open flames、 high temperature、Separate storage with oxidant and acid

Vapour pressure, Pa at 20°C: 53

3.4 (vs air)

LC50 (4 hr) in rats: 233 ppm (Jacobson)

Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.

vol% in air: 1.86.3

Faint burning odor

Bitter

Henry's Law constant = 7.9X10-8 atm cu m/mol at 25 °C (est)

pKa = 9.55

Detectable concentration in atmosphere by odor = 8 ppm|Easily resinified by acids|Heat of formation = -276.2 kJ/mol at 25 °C; Heat capacity = 204.0 J/mol-K at 25 °C|Heat of fusion = 13.13 kJ/mol|For more Other Experimental Properties (Complete) data for FURFURYL ALCOHOL (8 total), please visit the HSDB record page.

Slightly soluble in water.

Alcohols and Polyols

Acetyl bromide reacts violently with alcohols or water, [Merck 11th ed., 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid, [Chem. Eng. News 45(43):73(1967); J, Org. Chem. 28:1893(1963)]. FURFURYL ALCOHOL will polymerize rapidly and at times with explosive force in the presence of strong mineral acids, [NFPA 491M, 1991]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites, [NFPA 491 M, 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)]. 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 heat applied, [MCA Case History 858(1963)]. In the attempt to prepare furfuryl formate from furfuryl alcohol and concentrated formic acid an explosion occurred, [Chem. Eng. News 18:72(1940)].

736 °F (USCG, 1999)|+490 °C (915 °F)|390 °C

-2548 kJ/mol

LOWER 1.8%, UPPER 16.3% BY VOL|Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.

53.6 kJ/mol at 171 °C

Safety Information

III

6.1

UN 2874 6.1/PG 3

1

R21/22; R23; R36/37; R40; R48/20

S23-S36/37/39

LU9100000

T

Separated from strong oxidants, strong acids and food and feedstuffs. Well closed. Ventilation along the floor.

Turns amber due to autoxidation and intermolecular dehydration during storage and turns black in presence of air

P260-P280-P284-P301 + P310 + P330-P304 + P340 + P310-P403 + P233

H301 + H311-H315-H319-H330-H335-H351-H373

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.

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.|For more Hazardous Reactivities and Incompatibilities (Complete) data for FURFURYL ALCOHOL (10 total), please visit the HSDB record page.

Furfuryl alcohol is an indirect food additive for use only as a component of adhesives.

Toxicology & Carcinogenesis Studies of Furfuryl Alcohol in F344/N Rats and B6C3F1 Mice p.6 Technical Report Series No. 482 (1999) NIH Publication No. 99-3972 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. (ERG, 2016)|Combustible. Above 75 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree, Reactive - 1st degree

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P322, P330, P337+P313, P363, P403+P233, P405, and P501|H301 (11.57%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P320, P321, P322, P330, P337+P313, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2117 companies from 40 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P322, P330, P333+P313, P337+P313, P363, P403+P233, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P260, P261, P264, P270, P271, P272, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: 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.] (NIOSH, 2016)|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.|For more Personal Protective Equipment (PPE) (Complete) data for FURFURYL ALCOHOL (6 total), please visit the HSDB record page.|(See protection codes)

Moderate, when exposed to heat; can react with oxidizing materials.

Explosive limits: Lower 1.8%; Upper 16.3%, both between 72-122 °C.|Explosion hazard: moderate, when exposed to heat or flame.|Explosive limits , vol% in air: 1.8-16.3

To fight fire use alcohol foam, carbon dioxide, dry chemical ... .

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.

/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)/ 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)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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.|For more DOT Emergency Guidelines (Complete) data for FURFURYL ALCOHOL (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

The material is markedly irritating & injurious to the eyes.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 50 ppm (200 mg/cu m).|Vacated 1989 OSHA PEL TWA 10 ppm (40 mg/cu m); STEL 15 ppm (60 mg/cu m), skin designation, is still enforced in some states.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 ppm (40 mg/cu m), skin.|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 15 ppm (60 mg/cu m), skin.

Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking liquid in sealable non-plastic containers. Absorb remaining liquid in inert absorbent. Wash away remainder with plenty of water. Do NOT wash away into sewer.

Separated from strong oxidants, acids and food and feedstuffs. Well closed. Ventilation along the floor.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

The substance is irritating to the eyes and respiratory tract.

The substance defats the skin, which may cause dryness or cracking. Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the upper respiratory tract and kidneys. This substance is possibly carcinogenic to humans.

NO open flames. Above 75 °C use a closed system and ventilation.

STRICT HYGIENE! PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Wastewater leachate collected from the Love Canal, Niagara Falls, NY landfill in 1978 contained an estimated 76.7 mg/L of furfuryl alcohol(1). Mean emission factors of furfuryl alcohol in smoldering smoke from wood and from the self-sustained smoldering smoke from bark, litter, and duff (collected from ponderosa pine in northwestern Montana) fires were 0.28, 0.87, 0.1, and 0.044 g/kg dry mass of fuel consumed, respectively(2). No furfuryl alcohol was detected in the smoldering smoke from needles, bark, litter, duff, and humus fires(2). Furfuryl alcohol was qualitatively detected in kitchen waste exudate from household waste collected in Denmark(3). Furfuryl alcohol was qualitatively detected in 4 of >4000 samples of effluent from 4 of 46 industrial categories (pulp and paper, synfuels, publicly-owned treatment works, and rum industries)(4).

INDOOR: Furfuryl alcohol was qualitatively detected in 1 of 44 air samples taken from a chamber simulating indoor conditions containing wood-based furniture with different coatings(1).

Toxicity

LC50 Rat inhalation 233 ppm/ 4 hr|LD50 Rat oral 275 mg/kg fed as 2 % aq. soln|LD50 Rat ip 650 mg/kg|LD50 Rat sc 85 mg/kg|For more Non-Human Toxicity Values (Complete) data for FURFURYL ALCOHOL (7 total), please visit the HSDB record page.

Groups of 50 male and 50 female F344/N rats were exposed to furfuryl alcohol by inhalation, 6 hr/day 5 days/wk for 105 wk at concn of 0, 2, 8 or 32 ppm. Groups of 50 male and 50 female mice were exposed to furfuryl alcohol by inhalation, 6 hr/day 5 days/wk for 105 wk, at concn of 0, 2, 8 or 32 ppm. CONCLUSIONS: Under the conditions of these 2 yr inhalation studies, there was some evidence of carcinogenic activity of furfuryl alcohol in male F344/N rats based on incr incidences of combined neoplasms of the nose. There was equivocal evidence of carcinogenic activity in female F344/N rats based on marginally incr incidences of neoplasms of the nose and renal tubule. There was some evidence of carcinogenic activity of furfuryl alcohol in male B6C3F1 mice based on incr incidences of renal tubule neoplasms. There was no evidence of carcinogenic activity of furfuryl alcohol in female B6C3F1 mice exposed to 2, 8 or 32 ppm.

Furfuryl alcohol is found in the smoke from burning wood(1).

Furfuryl alcohol's production and use as a solvent, in the manufacture in resins, as a wetting agent, a gel retarder, a diluent, a liquid propellant, in flavoring, and in foundry cores(1-3) may result in its release to the environment through various waste streams(SRC).

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 °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 °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).

The rate constant for the vapor-phase reaction of furfuryl alcohol with photochemically-produced hydroxyl radicals has been estimated as 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Furfuryl alcohol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Furfuryl alcohol absorbs light at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(1). Reaction with photochemically generated singlet oxygen may be a significant removal process in surface water based upon a measured rate constant for this process of 1.2X10+8/mole-sec at 19 °C which corresponds to a half-life of 40 hours at a singlet oxygen concentration of 4X10-14 mole/L(4).

An estimated BCF of 3.2 was calculated for furfuryl alcohol(SRC), using a log Kow of 0.28(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Koc of furfuryl alcohol is estimated as 34(SRC), using a log Kow of 0.28(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that furfuryl alcohol is expected to have very high mobility in soil. The pKa of furfuryl alcohol is 9.55(4), indicating that this compound will primarily exist in its neutral form in the environment(5).

The Henry's Law constant for furfuryl alcohol is estimated as 7.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 0.609 mm Hg(1), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(2). This Henry's Law constant indicates that furfuryl alcohol is expected to be essentially nonvolatile from water surfaces(3). Furfuryl alcohol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Furfuryl alcohol may volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Furfuryl alcohol was found in canned cream, canned kernel, frozen kernel, and fresh kernel forms of cooked sweet corn at concentrations of 1000, 350, 8, and 5 ppb, respectively(1). Concentrations of 500 and 5,900 ug/kg furfuryl alcohol were detected in microwave-oven produced popcorn volatiles(2). Furfuryl alcohol was detected at 2,000 and 2,300 ppb in rice cake volatiles(3). Furfuryl alcohol was detected in the volatiles of three commercial fermented soybean curd brands collected at local markets in Hong Kong at concentrations of 382.5, 412.7, and 1927.6 ug/kg dry sample(4). Furfuryl alcohol was qualitatively detected in the volatiles of raw beef(5). The volatile flavor components of roasted peanuts contained furfuryl alcohol concentrations ranging from 9.54X10-4 to 4.93X10-3 ug/g(6). Furfuryl alcohol was detected at concentrations of 0.19, 1.21, 1.93, and 8.89 ppb in the volatiles of water-boiled duck meat, duck fatty tissue, Cantonese style roasted duck, and Cantonese style roasted duck gravy, respectively(7). Furfuryl alcohol was detected at a concentration of less than the quantitation limit of 10 ppb in nectarine volatiles(8). It was qualitatively detected in the mixture of volatile components from roasted filberts(9), fried bacon, pork, and smoke flavors(10), heated sukyaki mixture (beef, vegetables, and sugar and soy sauce seasonings) and individual sukyaki ingredients (beef and soy sauce)(11), fried chicken (12), and mountain Beaufort cheese(13). It has been listed as a constituent of the compounds which contribute to the aroma of coffee(14).

Furfuryl alcohol was detected in 2 of 8 samples of mother's milk volatiles with two samples collected at each of four sites, Bayonne, NJ, Jersey City, NJ, Pittsburgh, PA, and Baton Rouge, LA; positive samples were from Jersey City and Baton Rouge(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 77,710 workers (14,624 of these are female) are potentially exposed to furfuryl alcohol in the US(1). Occupational exposure to furfuryl alcohol may occur through inhalation and dermal contact with this compound at workplaces where furfuryl alcohol is produced or used(SRC). The daily, time-weighted average air concentration of furfuryl alcohol ranged from 0.80 to 23 mg/ cu m in the work rooms of two aluminum sand foundries collected from 1992 to 1995(2). Monitoring data indicate that the general population may be exposed to furfuryl alcohol via inhalation of ambient air, ingestion of food, and dermal contact with this compound and other products containing furfuryl alcohol(SRC).

Furfuryl alcohol was detected in 2 of 8 samples of mother's milk volatiles with two samples collected at each of four sites, Bayonne, NJ, Jersey City, NJ, Pittsburgh, PA, and Baton Rouge, LA; positive samples were from Jersey City and Baton Rouge(1).

Drug Information

... /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.

Furfuryl alcohol is oxidized to furoic acid, which is excreted as the glycine conjugate furoyl glycine ... . Furoyl glycine was the major end product in the urine of rats after feeding furfuryl alcohol.|Furfuryl alcohol is first metabolized by oxidation to the aldehyde (furfural) and then to the corresponding acid (furoic acid), followed by decarboxylation to CO2, excreted as the unchanged acid, conjugated with glycine, or condensed with acetic acid. Furoylglycine was identified as the major urinary metabolite in rats after an oral dose of furfuryl alcohol. Furoic acid and furanacrylic acid were also identified as minor metabolites.|Following oral administration of 0.275, 2.75, and 27.5 mg/kg (14)Cfurfuryl alcohol in rats, at least 86 to 89% was absorbed. ... No furfuryl alcohol was identified in the urine. Furoylglycine was the major urinary metabolite (73 to 80% of dose), and furoic acid (1 to 6%) and furanacrylic acid (3 to 8%) were the minor metabolites.|... The major metabolite was furoylglycine and the minor metabolites were furoic-acid and furanacrylic-acid for both FAL and FOL. The extent and rate of excretion of the metabolites were unaffected by dose.|Furfuryl alcohol has known human metabolites that include 2-Sulfoxymethylfuran.

Inhalation causes headache, nausea, and irritation of nose and throat. Vapor irritates eyes; liquid causes inflammation and corneal opacity. Contact of skin with liquid causes dryness and irritation. Ingestion causes headache, nausea, and irritation of mouth and stomach. (USCG, 1999)

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: 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. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. 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)|(See procedures)


Fresh air, rest. Refer immediately for medical attention.


Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.

Basic Treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/|Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques, with a bag-valve-mask device, may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam (Valium) ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/

/CASE REPORTS/ Three workers exposed for 15 min up to 43 mg/cu m (11ppm) did not report discomfort.|/CASE REPORTS/ Two studies of foundries in which furfuryl alcohol vapor was given off during core preparation were reviewed. /Investigators/ noted no discomfort from concentrations up to 10.8 ppm for 15 minutes, but at 15.8 ppm, severe lacrimation occurred; 0.33 ppm of formaldehyde was present. In another foundry, however, /investigators/ found no ocular irritation, headache, nausea, or dizziness in three workers exposed at 8-hour TWA concentrations of 5 or 6 ppm. Other workers were exposed for unspecified periods at concentrations up to 8 ppm (in one case 16 ppm) without apparent ill effects.|/HUMAN EXPOSURE STUDIES/ /Investigators/ reported that single, oral doses of 0.6 to 1.0 g furfuryl alcohol in 5% aqueous solution given to three men stimulated the rate of respiration.|/SIGNS AND SYMPTOMS/ ... Small doses ... stimulated respiration ... larger doses depressed respiration, reduced body temperature, produced nausea, salivation, diarrhea, dizziness and diuresis.|For more Human Toxicity Excerpts (Complete) data for FURFURYL ALCOHOL (9 total), please visit the HSDB record page.

2-furancarbinol

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, mucous membrane; dizziness; nausea, diarrhea; diuresis; resp, body temperature depression; vomiting; dermatitis


Cough. Sore throat. Dizziness. Headache. Nausea.


MAY BE ABSORBED! Dry skin. Redness.


Redness. Pain.

Eyes, skin, respiratory system, central nervous system

Furfuryl alcohol Use and Manufacturing

Methods of Manufacturing

1. Refining method: anhydrous sodium sulfate or anhydrous potassium carbonate after fractionation. Fractionation is preferably carried out under a stream of nitrogen. Alternatively, the distillate may be distilled under reduced pressure to remove the tar-like substance, and the resulting mixture may be shaken with an aqueous sodium bisulfite solution, dried over anhydrous sodium sulfate and fractionated by distillation under reduced pressure in the presence of sodium carbonate. 2. Furfural alcohol industrial system is derived from hydrogenation of furfural: hydrogenation is divided into two kinds of liquid hydrogenation and gas phase hydrogenation. Liquid hydrogenation method: furfural and hydrogen gas are mixed at a ratio of 1: 42 (mol ratio) in the presence of a Cu-Cr-Ca catalyst at 190-210C and 5-8 MPa (or 10 MPa or more, 170C, -Cr catalyst). After the reaction, the solid catalyst is precipitated and removed, and the obtained liquid is crude furfuryl alcohol. Gas phase hydrogenation: In a tubular reactor, furfural is reacted with hydrogen at a molar ratio of 1: 42 in the presence of a Ni-Cu or Cr-Cu catalyst at 80 to 170 ° C and 0.1 to 0.39 MPa Too. The obtained crude furfuryl alcohol is distilled under the pressure of 80-87 kPa to remove the tar-like substance, and then washed with sodium bisulfite, dried and dehydrated, then added sodium carbonate to vacuum distillation to obtain pure furan-methanol. 3. Disproportionation method to furfural as raw material, the furfural in the presence of caustic soda disproportionation reaction, the advantages of this method is simple equipment, does not require reducing agent, the drawback is the low utilization of raw materials. 4. Tobacco: BU, 56; OR, 18; FC, 9; FC, BU, OR, 18; FC, 18; FC, 40.

Uses

It is a good solvent and rocket fuel for resins, varnishes and pigments. It can also be used in synthetic fibers, rubber, pesticides and foundry industries. It is also used as a raw material for the synthesis of various furan resins and anticorrosive coatings. It is also a good solvent; GB2761--1997 Specified as permitted food flavors. Mainly used to prepare coke-flavored flavors. FDA, §175.105: It is specified as an indirect food additive (binder). Furfuryl alcohol is used in organic synthesis, and levulinic acid (fruit acid) is obtained by hydrolysis, which is an intermediate of nutritional medicine calcium fructose. Furan resins with various properties (such as furfuryl alcohol resin, furan Ⅰ or furan Ⅱ resins), furfuryl alcohol-urea-formaldehyde resin and phenolic resin can be prepared from furfuryl alcohol; the cold resistance of plasticizers made from furfuryl alcohol is better than that of butyl, Octanol esters are also good solvents for furan resins, varnishes, pigments and rocket fuel. It is also used in synthetic fibers, rubber, pesticides and foundry industries. The product is flammable and toxic. The oral LD50 of mice is 275mg/kg.


Processing aids, not otherwise listed|Adhesives and sealant chemicals


Building/construction materials not covered elsewhere

Production

< 25,000 lb|10,000,000 - 50,000,000 lb|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|For more U.S. Production (Complete) data for FURFURYL ALCOHOL (7 total), please visit the HSDB record page.

CLOSE TO 100% AS A REACTANT IN FURAN RESIN PRODUCTION (1974)

Grade: Technical, refined.

All other basic organic chemical manufacturing|2-Furanmethanol, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|Agriculture, forestry, fishing and hunting|2-Furanmethanol: ACTIVE|The polymer is used as a mortar for bonding acid-proof brick and chemical masonry.

Method: NIOSH 2505, Issue 2; Procedure: gas chromatography with flame ionization detector; Analyte: furfuryl alcohol; Matrix: air; Detection Limit: 0.01 mg/sample.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 2nd degree, Reactive - 1st degree

Flavoring Agents

Computed Properties

Molecular Weight:98.10
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:98.036779430
Monoisotopic Mass:98.036779430
Topological Polar Surface Area:33.4
Heavy Atom Count:7
Complexity:54
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Price Analysis

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  • Data: 2025-04-07
  • Price: 9200.00Yuan/ton
  • Change: 0

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