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Home > Encyclopedia > Tetrahydrofurfuryl alcohol

Tetrahydrofurfuryl alcohol

Tetrahydrofurfuryl alcohol structure

Tetrahydrofurfuryl alcohol 

structure
  • CAS No:

    97-99-4

  • Formula:

    C5H10O2

  • Chemical Name:

    Tetrahydrofurfuryl alcohol

  • Synonyms:

    2-Furanmethanol,tetrahydro-;Furfuryl alcohol,tetrahydro-;Tetrahydro-2-furanmethanol;QO THFA;Tetrahydro-2-furancarbinol;Tetrahydrofurfuryl alcohol;Tetrahydro-2-furylmethanol;THFA;2-(Hydroxymethyl)tetrahydrofuran;Tetrahydro-2-furanylmethanol;Rac-(Tetrahydrofuran-2-yl)methanol;NSC 15434;(Tetrahydrofuran-2-yl)methanol;(±)-Tetrahydrofurfuryl alcohol;(Oxolan-2-yl)methanol;72074-94-3;82853-20-1

  • Categories:

    Cosmetic Ingredient  >  Dissolving Agent

Description

Colorless to light yellow liqui Tetrahydrofurfuryl alcohol has a faint, warm, oily, caramellic odor with a coffee and nut-like flavor at very low levels (0.03 to 1 ppm).


Tetrahydrofurfuryl alcohol appears as a clear colorless liquid with a mild odor. Vapors are heavier than air.|Liquid|COLOURLESS HYGROSCOPIC LIQUID.|Clear colourless liquid; Mild, warm oily caramel aroma


Tetrahydrofurfuryl alcohol appears as a clear colorless liquid with a mild odor. Vapors are heavier than air.|Tetrahydrofurfuryl alcohol is a primary alcohol that is methanol in which one of the hydrogens of the methyl group has been replaced by a tetrahydrofuran-2-yl group. It has a role as a protic solvent. It is a primary alcohol and a member of oxolanes.

Tetrahydrofurfuryl alcohol Basic Attributes

102.132

102.13

202-625-6

1159

15434

1993

DTXSID1029128

Colorless liquid

29321300

Characteristics

29.46

-0.1

Colorless to pale yellow liquid

1.0544 g/cm3 @ Temp: 20 °C

<-80 °C

178 °C @ Press: 760 Torr

74ºC

1.451-1.453

Solubility in water: miscible

Packaging integrity, light loading, warehouse ventilation, away from open flame, high temperature, and oxidants stored separately

Vapour pressure, kPa at 25°C: 0.186

Relative vapour density (air = 1): 3.5

LD50 orally in Rabbit: 1600 mg/kg

Lower flammable limit: 1.5% by volume; Upper flammable limit: 9.7% by volume

vol% in air: 1.5.7

Mild odor

Occurs in two isomeric forms: D-isomer (levorotatory), L-isomer (dextrorotatory).|Octane number: 82.5; Kauributanol value: 71.5|Dilution ratio (lacquer ingredients): 4.5; dielectric constant at 23 °C: 13.6; heat capacity at 30-37 °C: 0.432 cal/g/deg C|In org synth undergoes reactions of primary alc, while ring exhibits characteristics of saturated cyclic ether.|Coefficient of expansion: 0.00052

Denser than water and 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]. 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].

540 °F (282 °C)|280 °C

708.6 cal/g/mole @ constant vol

Lower flammable limit: 1.5% by volume; Upper flammable limit: 9.7% by volume

As a result of flow, agitation, etc., electrostatic charges can be generated.

51.55 kJ/mol

Safety Information

I; II; III

NA 1993 / PGIII

2

R36

S39

LU2450000

Xi

Separated from strong oxidants. Dry. Well closed. Ventilation along the floor.

P201-P280-P305 + P351 + P338-P308 + P313-P337 + P313

H319-H360Df

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Violent or explosive reaction with 3-nitro-N-bromophthalimide. ... Can react with oxidizing materials.

Tetrahydrofurfuryl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.|Tetrahydrofurfuryl alcohol is an indirect food additive for use only as a component of adhesives.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. 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 ground and collect in low or confined areas (sewers, basements, tanks). 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 are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)|Combustible. Above 74 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with strong oxidants.

|Danger|H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P264, P280, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 2316 companies from 16 notifications to the ECHA C&L Inventory.|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). 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 128 [Flammable Liquids (Water-Immiscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in 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, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|PERSONS REQUIRED TO HANDLE FURFURAL & ITS DERIVATIVES SHOULD WEAR PERSONAL PROTECTIVE EQUIPMENT TO AVOID SKIN CONTACT, INCLUDING EYE & FACE PROTECTION & HAND PROTECTION. WHERE BRIEF EXPOSURE TO HIGH ATMOSPHERIC CONCN IS POSSIBLE, WORKERS SHOULD WEAR RESP PROTECTIVE EQUIPMENT. /FURFURAL & DERIVATIVES/

Combustible when exposed to heat or flame.

MANY OF THE REACTIONS OF SEVERAL N-CHLORO- & N-BROMOIMIDES ARE EXTREMELY VIOLENT OR EXPLOSIVE. THOSE OBSERVED INCLUDE ... 3-NITRO-N-BROMOPHTHALIMIDE WITH TETRAHYDROFURFURYL ALCOHOL ... . /N-HALOIMIDES/|Lower explosive limit: 1.5% Upper explosive limit: 9.7% @ 72-122 °F|Violent or explosive reaction with 3-nitro-N-bromophthalimide. ... Explosive in the form of vapor when exposed to heat or flame.|Explosive limits , vol% in air: 1.5-9.7

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 chemial or carbon dioxide.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to disperse vapors and dilute standing pools of liquid.|Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.|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.

... Irritating to human ... eyes.|A severe eye irritant. Irritating to skin & mucous membranes.

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water.

Separated from strong oxidants. Dry. Well closed. Ventilation along the floor.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes. The substance may cause effects on the central nervous system at high concentrations. This may result in lowering of consciousness.

Animal tests show that this substance possibly causes toxic effects upon human reproduction.

NO open flames. Above 74 °C use a closed system and ventilation. Prevent build-up of electrostatic charges (e.g., by grounding).

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual 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.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Tetrahydrofurfuryl alcohol has been identified as a constituent in flue-cured tobacco(1).

Toxicity

LD50 Guinea pig single oral 0.8 to 1.6 g/kg|LD50 Rat single oral 1.6 to 3.2 g/kg|LD50 Mouse oral 2300 mg/kg|LD50 Rabbit iv 725 mg/kg

Persons with existing skin disorders may be more susceptible to the effects /of tetrahydrofuran exposure/. /Tetrahydrofuran/

Tetrahydrofurfuryl alcohol's production and use as a specialty organic solvent(1); as a cleaner and paint stripper(1); in crop sprays(1), in water-based paints(1), in the dyeing and finishing of textiles and leathers(1), and as an intermediate in pharmaceutical applications(1), 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 1(SRC), determined from a structure estimation method(2), indicates that tetrahydrofurfuryl alcohol is expected to have very high mobility in soil(SRC). Volatilization of tetrahydrofurfuryl alcohol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Tetrahydrofurfuryl alcohol is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.80 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that tetrahydrofurfuryl 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 4.1X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.11(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Tetrahydrofurfuryl alcohol was considered readily biodegradable from the results of a screening test using an adapted activated sludge inoculum in which 96.1% of initial tetrahydrofurfuryl alcohol (based upon COD) was degraded in 120 hours of incubation(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetrahydrofurfuryl alcohol, which has a vapor pressure of 0.80 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase tetrahydrofurfuryl 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 13.4 hrs(SRC), calculated from its estimated rate constant of 2.9X10-11 cu cm/molecule-sec at 25 °C(3).

The rate constant for the vapor-phase reaction of tetrahydrofurfuryl alcohol with photochemically-produced hydroxyl radicals has been estimated as 2.9X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 13.4 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). Tetrahydrofurfuryl alcohol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

An estimated BCF of 3 was calculated for tetrahydrofurfuryl alcohol(SRC), using an estimated log Kow of -0.11(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(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tetrahydrofurfuryl alcohol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that tetrahydrofurfuryl alcohol is expected to have very high mobility in soil(SRC).

The Henry's Law constant for tetrahydrofurfuryl alcohol is estimated as 4.1X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tetrahydrofurfuryl alcohol is expected to be essentially nonvolatile from moist soil and water surfaces(2). Tetrahydrofurfuryl alcohol is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.80 mm Hg(3).

Tetrahydrofurfuryl alcohol has been identified as a constituent of coffee aroma(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 79,915 workers are potentially exposed to tetrahydrofurfuryl alcohol in the US(1). Occupational exposure to tetrahydrofurfuryl alcohol may occur through dermal contact and inhalation of vapor(2) with this compound at workplaces where tetrahydrofurfuryl alcohol is produced or used(SRC).

Drug Information

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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 suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. 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. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. (ERG, 2016)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Eye splashes should be copiously flushed with water. Contaminated clothing should be removed and skin washed with soap and water. Oxygen therapy may be given following acute inhalation. /Furfural and derivatives/|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. Provide a low-stimulus environment. Monitor for shock 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. Treat frostbite by rapid rewarming ... . /Ethers and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if 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. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethers and related compounds/

MODERATELY IRRITATING TO SKIN, MUCOUS MEMBRANES.|EFFECTS REPORTED IN ACUTE POISONING WHICH RESULTED IN DEATH WITHIN 2-3 DAYS WERE SWELLING IN THE BRAIN, HEMORRHAGES IN VISCERAL PLEURA & EPICARDIUM, HYPERVOLEMIA OF ORGANS, & EXPANDED LUNG. MUCOSA OF THE UPPER DIGESTIVE TRACT & STOMACH SHOWED SWELLING, HYPERVOLEMIA, HEMORRHAGE, & NECROSIS. IN DEATH OCCURRING AFTER 3 DAYS, LIVER WEIGHT INCREASED & SHOWED YELLOWISH-BROWN CROSS SECTION WITH HEMORRHAGES. HEPATOCYTES WERE NECROTIC & SOME CONTAINED FAT DROPLETS.|... Irritating to human ... eyes.

tetrahydrofurfuryl alcohol

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Sore throat. Cough. Headache. Nausea. Dizziness. Drowsiness. Unconsciousness.


Redness.


Redness. Pain.

Tetrahydrofurfuryl alcohol Use and Manufacturing

Methods of Manufacturing

1. Hydrogenation from furfural. When a nickel-chromium-copper catalyst is used, the reaction temperature is 170 to 180 ° C and the pressure is 7.5 to 10.5 MPa. By the use of furfural in the presence of catalyst Ni, with 170 ~ 180 ℃, 7.355 ~ 7.845MPa under continuous pressure hydrogenation derived. Refining method: fractionation purification.
2. Tobacco: FC, 9, 18.

Uses

Solvent for fats, waxes, resins, in organic synthesis.


Intermediates


Electrical and electronic products

Production

1,000,000 - 10,000,000 lb

Grades: commercial; industrial (80%).|98% GRADE

Agriculture, forestry, fishing and hunting|2-Furanmethanol, tetrahydro-: ACTIVE

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Solvent

Flavoring Agents

Computed Properties

Molecular Weight:102.13
XLogP3:-0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:102.068079557
Monoisotopic Mass:102.068079557
Topological Polar Surface Area:29.5
Heavy Atom Count:7
Complexity:54
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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