Tetrahydrofurfurylalkohol

Tetrahydrofurfuryl alcohol

HCID 7360CAS 93842-55-8

Grundinformationen

Standard-SMILES
OCC1CCCO1
InChIKey
BSYVTEYKTMYBMK-UHFFFAOYSA-N
Summenformel
C5H10O2
Durchschnittliche Molmasse
102,13 g/mol
Monoisotopische Masse
102,06807956

Namen und Bezeichner

Bevorzugter Name
Tetrahydrofurfuryl alcohol
IUPAC
oxolan-2-ylmethanol
Lokaler Name
Tetrahydrofurfurylalkohol
Englischer Name
Tetrahydrofurfuryl alcohol
Summenformel
C5H10O2
Molmasse
102.13

Namen und Synonyme

TETRAHYDROFURFURYL ALCOHOL97-99-4Tetrahydro-2-furanmethanolTHFATetrahydro-2-furanylmethanol2-Furanmethanol, tetrahydro-QO ThfaFurfuryl alcohol, tetrahydro-Tetrahydro-2-furancarbinolTetrahydrofuryl carbinol2-(Hydroxymethyl)tetrahydrofuranTetrahydro-2-furfuryl alcohol
Weitere Namen anzeigen
TetrahydrofurfurylFEMA 3056Oxolane-2-methanol2-Hydroxymethyl oxolaneTetrahydrofuran methanol
TetrahydrofurylalkoholTetrahydro-2-furylmethanolTetrahydrofurfurylalkoholFEMA No. 3056DTXSID1029128XD95821VF9NSC-15434DTXCID909128

Datenbank-Bezeichner

CAS
93842-55-8、97-99-4
PubChem CID
7360
DTXSID
DTXSID1029128
ChEMBL
CHEMBL2287521
ChEBI
CHEBI:137944
UNII
XD95821VF9
EC Number
202-625-6
Nikkaji
J4.733C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,1
Polarare Oberfläche (TPSA)
29,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
7

Experimentelle und physikochemische Eigenschaften

Odor · 2 Einträge

Mild odor

Odorless

Density · 3 Einträge

1.0544 @ 20 °C/20 °C

Relative density (water = 1): 1.05

1.050-1.052

Viscosity6.24 centipoises @ 20 °C
Color/FormColorless liquid
Solubility · 5 Einträge

Miscible with water, alcohol, ether, acetone, chloroform, benzene

1000 mg/mL at 25 °C

Solubility in water: miscible

Soluble in water, fats

Soluble (in ethanol)

Flash Point · 4 Einträge

167 °F (NFPA, 2010)

75 °C

167 °F (75 °C) (OPEN CUP)

74 °C c.c.

Physikochemische Eigenschaften

Schmelzpunkt
-80 °C · -80 °C (lit.)
Siedepunkt
178 °C · 178 °C (lit.)
Dichte
1.054 g/mL · 1.054 g/mL at 25 °C (lit.)
Dampfdichte
3.52 · 3.52 (vs air)
Dampfdruck
2.3 mm · 2.3 mm Hg ( 39 °C)
Brechungsindex
20 · n20/D 1.452(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation];H360Df: May damage the unborn child; Suspected of damaging fertility [Danger Reproductive toxicity]

P203, P264+P265, P280, P305+P351+P338, P318, P337+P317, P405, and P501 (click each P-code to see the statement)

Danger

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 2-Furanmethanol, tetrahydro-

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Furanmethanol, tetrahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Furanmethanol, 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: 05-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13371

2-Furanmethanol, tetrahydro-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Furanmethanol, tetrahydro-: Human health tier II assessment
DOT LabelCombustible Liquid
Fire Hazards · 2 Einträge

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 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. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion or sodium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2024)

Combustible. Above 74 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with strong oxidants.

Fire PotentialCombustible when exposed to heat or flame.
Health Hazards · 1 Eintrag

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas. 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. (ERG, 2024)

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.;LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use 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. For petroleum crude oil, do not spray water directly into a breached tank car. This can lead to a dangerous boil over. 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 nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use water in large amounts, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 Einträge

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.

Rinse mouth. Give nothing to drink. Do NOT induce vomiting. Refer for medical attention .

First Aid · 1 Eintrag

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;Refer to the "General First Aid" section. Specific First Aid: 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. (ERG, 2024)

Safe StorageSeparated from strong oxidants. Dry. Well closed. Ventilation along the floor.
Fire Fighting Procedures · 1 Eintrag

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.

Storage ConditionsFURFURAL & ITS DERIVATIVES SHOULD BE STORED IN WELL-VENTILATED AREAS, SHELTERED FROM DIRECT SUNLIGHT & AWAY FROM HEAT & OTHER SOURCES OF IGNITION. /FURFURAL & IT DERIVATIVES/

Toxikologische Informationen

Environmental Fate · 3 Einträge

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).

Food Survey ValuesTetrahydrofurfuryl alcohol has been identified as a constituent of coffee aroma(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Signs and Symptoms · 4 Einträge

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

Redness.

Redness. Pain.

See Inhalation.

Soil Adsorption/Mobility · 1 Eintrag

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).

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: 2-Furanmethanol, tetrahydro-

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Furanmethanol, tetrahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Furanmethanol, 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: 05-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13371

2-Furanmethanol, tetrahydro-: Does not have an individual approval but may be used under an appropriate group standard

FDA Requirements · 2 Einträge

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.

FIFRA Requirements · 1 Eintrag

Residues of tetrahydrofurfuryl alcohol are exempted from the requirement of a tolerance when used as a solvent or cosolvent in accordance with good agricultural practices as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
NA 1993 / PGIII
hs_code
29321300
RTECS-Nr.
LU2450000
risk_code
36-62-61

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm;Extracellular

Verwendung und Herstellung

Uses · 6 Einträge

Used as a solvent (fats, waxes, and resins) and in organic synthesis; [Merck Index] Used as a cleaner, paint stripper, and solvent (replacement for chlorinated solvents); Also used in crop sprays, water-based paints, and to make pharmaceuticals and elastomers; [HSDB]

Metal Degreasing [Category: Clean];Painting (Solvents) [Category: Paint]

Solvent for fats, waxes, resins; in organic synthesis

Solvent for dyes for leather; chlorinated rubber; cellulose esters; solvent-softener for nylon; vegetable oils; coupling agent

Plasticizer, synthesis of lysine; paint and varnish ingredient.

Specialty organic solvent; cleaner and paint stripper; replacement for chlorinated solvents; crop sprays; water-based paints; dyeing and finishing of textiles and leathers; intermediate in pharmaceutical applications; co- reactive viscosity depressant for vinyl terminated epoxy systems; in elastomer production.

U.S. Production2023: 7,000,000 - <8,500,000 lb;2022: 10,000,000 - <25,000,000 lb;2021: 10,000,000 - <25,000,000 lb;2020: 8,500,000 - <10,000,000 lb
Industry UsesSolvent;Intermediate
Methods of ManufacturingMfr by catalytic hydrogenation of furfural or furfuryl alcohol.
Formulations/Preparations · 2 Einträge

Grades: commercial; industrial (80%).

98% GRADE

Household ProductsInformation on 1 consumer products that contain Tetrahydrofurfuryl alcohol in the following categories is provided:;• Home Maintenance
Anwendungen · 2 Einträge

OccurrenceReported found in shoyu (fermented soya hydrolysate), coffee and fresh mango.

VerwendenTetrahydrofurfuryl alcohol is used extensively in various industries as a high-purity, water miscible solvent, and as a chemical intermediate. It was used as Solvent for vinyl resins; dyes for leather; chlorinated rubber; cellulose esters; solvent softener for nylon; vegetable oils; coupling agent; organic synthesis.

Darstellung

synthetischeTetrahydrofurfuryl alcohol is produced by catalytic reduction of furfural with Raney-Ni; also by destructive hydrogenation of lignin.

Anbieter50 Anbieter

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.

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