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109-99-9

Basic Information
CAS No.: 109-99-9
Name: Tetrahydrofuran
Article Data: 381
Molecular Structure:
Molecular Structure of 109-99-9 (Tetrahydrofuran)
Formula: C4H8O
Molecular Weight: 72.1069
Synonyms: NCI-C60560;Polytetrahydrofuran;Oxacyclopentane;Tetramethylene oxide;Hydrofuran;Tetrahydrofuraan;Tetraidrofurano;Butane .alpha.,.delta.-oxide;Oxolane;Tetrahydrfuran;Furan, tetrahydro-;Tetrahydrofuranne;THF;Cyclotetramethylene oxide;Furan,tetrahydro-;Furanidine;Diethylene oxide;Butane, 1,4-epoxy-;Tetra hydro furan;
EINECS: 203-726-8
Density: 0.904 g/cm3
Melting Point: 33-36 ºC
Boiling Point: 68.3 ºC at 760 mmHg
Flash Point: -21 ºC
Solubility: miscible with water
Appearance: Colorless liquid
Hazard Symbols: IrritantXi,FlammableF
Risk Codes: 36/37/38-19-11
Safety: 26-36-33-29-16
Transport Information: UN 2924 3/PG 2
PSA: 9.23000
LogP: 0.79680
Synthetic route
109-99-9

tetrahydrofuran

Conditions
ConditionsYield
With 3% Pd/C; hydrogen In isopropyl alcohol at 219.84℃; under 25858.1 Torr; for 5h; Inert atmosphere;100%
With hydrogen; acetic acid In water at 39.84℃; for 2h; Inert atmosphere;98%
With ruthenium; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; under 22502.3 Torr; for 36h; Autoclave; chemoselective reaction;95%
5371-52-8

2-hydroxytetrahydrofuran

109-99-9

tetrahydrofuran

Conditions
ConditionsYield
With phosphoric acid; 5%-palladium/activated carbon; hydrogen at 100℃; under 3750.38 - 13501.4 Torr; for 7h; Reagent/catalyst; Pressure; Temperature; Autoclave;100%
110-63-4

Butane-1,4-diol

109-99-9

tetrahydrofuran

Conditions
ConditionsYield
Trichlorbutylstannan at 80 - 84℃; for 9h;99%
Trichlorbutylstannan at 80 - 84℃; for 19h; Mechanism; different molar ratios, different times;99%
zirconium(IV) sulfate at 200℃; under 760.051 Torr; Product distribution / selectivity; Gas phase;99.5%
106-97-8

n-butane

109-99-9

tetrahydrofuran

Conditions
ConditionsYield
Stage #1: n-butane With oxygen at 403℃; under 2175.22 Torr;
Stage #2: With hydrogen In Phthalic acid dibutyl ester Product distribution / selectivity;
99.5%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

110-63-4

Butane-1,4-diol

D

110-15-6

succinic acid

E

64-19-7

acetic acid

Conditions
ConditionsYield
With hydrogen; 0.5 percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.37%
B 0.28%
C 0.37%
D 98.89%
E 0.08%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

67-56-1

methanol

D

110-63-4

Butane-1,4-diol

E

617-48-1

malic acid

F

110-15-6

succinic acid

G

64-19-7

acetic acid

H

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.45%
B 0.06%
C 0%
D 0.21%
E 0.36%
F 98.73%
G 0.04%
H 0.08%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

110-63-4

Butane-1,4-diol

D

591-81-1

4-hydroxybutanoic acid

E

110-15-6

succinic acid

F

64-19-7

acetic acid

G

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.77%
B 0.38%
C 0.24%
D 0.05%
E 98.28%
F 0.02%
G 0.26%

O-methyltetrahydrofuranium perchlorate

A

109-99-9

tetrahydrofuran

B

67-56-1

methanol

C

111-32-0

4-methoxybutanol

Conditions
ConditionsYield
With perchloric acid; sodium perchlorate; water at 25℃;A n/a
B n/a
C 98%
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

A

109-99-9

tetrahydrofuran

B

13436-45-8

2-methoxytetrahydrofuran

C

96-48-0

4-butanolide

D

71-23-8

propan-1-ol

E

64001-06-5

2-(4'-hydroxybutoxy)-tetrahydrofuran

F

110-63-4

Butane-1,4-diol

G

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich at 150 - 280℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);A 1%
B n/a
C 0.4%
D n/a
E n/a
F 98%
G 0.5%

(naphthalene)Yb(THF)3

A

109-99-9

tetrahydrofuran

B

ytterbium hydroxide

Conditions
ConditionsYield
With water In toluene byproducts: hydrogen, dihydronaphthalene; reaction time: 20 h; centrifuged, decanted, pptn. (Yb(OH)3) washed with toluene, soln. contains THF and C10H10 (82%)(detn. by GLC);A 112 %
B 98%
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Consensus Reports

NTP Carcinogenesis Bioassay (feed); Clear Evidence: mouse, Some Evidence: rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-475 ,1998. . Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 200 ppm; STEL 250 ppm
ACGIH TLV: TWA 200 ppm; STEL 250 ppm; BEI: 8 mg/L tetrahydrofuran in urine at end of shift
DFG MAK: 50 ppm (150 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

  Tetrahydrofuran (CAS NO.109-99-9), its  occupational chemical analysis use NIOSH: Tetrahydrofuran, 1609.

Specification

Tetrahydrofuran (THF) is an organic compound with the formula (CH2)4O. It is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. The compound is heterocyclic. As one of the most polar ethers with a wide liquid range, it is a useful solvent. With the CAS NO.109-99-9, it is also called 1,4-Epoxybutane ; AI3-07570 ; Agrisynth THF ; Butane, 1,4-epoxy- ; Butane, alpha,delta-oxide ; Butylene oxide ; CCRIS 6276 ; Cyclotetramethylene oxide ; Diethylene oxide.

Physical properties about Tetrahydrofuran are: (1)ACD/LogP: 0.473; (2)ACD/LogD (pH 5.5): 0.47; (3)ACD/LogD (pH 7.4): 0.47; (4)ACD/BCF (pH 5.5): 1.35; (5)ACD/BCF (pH 7.4): 1.35; (6)ACD/KOC (pH 5.5): 43.07; (7)ACD/KOC (pH 7.4): 43.07; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.417; (10)Molar Refractivity: 20.052 cm3; (11)Molar Volume: 79.76 cm3; (12)Polarizability: 7.949 10-24cm3; (13)Surface Tension: 28.8099994659424 dyne/cm; (14)Density: 0.904 g/cm3; (15)Flash Point: -17.222 °C; (16)Enthalpy of Vaporization: 29.81 kJ/mol; (17)Boiling Point: 68.278 °C at 760 mmHg; (18)Vapour Pressure: 152.442993164063 mmHg at 25°C

Preparation of Tetrahydrofuran: Tetrahydrofuran (CAS NO.109-99-9) can be manufactured from butane by using circulating solids technology in which butane is oxidized to maleic acid and thence to tetrahydrofuran
Manufacture of tetrahydrofuran from butane

Uses of Tetrahydrofuran:  The main application of Tetrahydrofuran (CAS NO.109-99-9) is as an industrial solvent for PVC and in varnishes.
Tetrahydrofuran(CAS NO.109-99-9) can be polymerized by strong acids to give a linear polymer called poly(tetramethylene ether) glycol (PTMEG), also known as PTMO, polytetramethylene oxide. The primary use of this polymer is to make elastomeric polyurethane fibers like Spandex. THF can be used in hydroboration reactions to synthesize primary alcohols, and as a solvent for organometallic compounds such as organolithium and Grignard reagents. It is often used in polymer science. It can be used to liquefy old PVC cement, and is often used industrially to degrease metal parts.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Take precautionary measures against static discharges;
4. Do not empty into drains;
5. Keep away from sources of ignition - No smoking;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2;
(2)InChIKey=WYURNTSHIVDZCO-UHFFFAOYSA-N;
(3)SmilesC1CCOC1

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 2300mg/kg (2300mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(9), Pg. 114, 1969.
guinea pig LDLo intraperitoneal 500mg/kg (500mg/kg) LIVER: FATTY LIVER DEGERATION American Industrial Hygiene Association Journal. Vol. 35, Pg. 21, 1974.
 
human TCLo inhalation 25000ppm (25000ppm) BEHAVIORAL: GENERAL ANESTHETIC "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 580, 1969.
mouse LCLo inhalation 24000mg/m3/2H (24000mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE WEAKNESS
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 5, Pg. 21, 1963.
mouse LD50 intraperitoneal 1900mg/kg (1900mg/kg)   Sangyo Igaku. Japanese Journal of Industrial Health. Vol. 24, Pg. 373, 1982.
 
rabbit LC inhalation > 1200ppm/4H (1200ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Sumitomo Sangyo Eisei. Sumitomo Industrial Health. Vol. 18, Pg. 89, 1982.
rat LC50 inhalation 21000ppm/3H (21000ppm) BEHAVIORAL: SLEEP

GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Sumitomo Sangyo Eisei. Sumitomo Industrial Health. Vol. 20, Pg. 141, 1984.
rat LD50 intraperitoneal 2900mg/kg (2900mg/kg)   Sangyo Igaku. Japanese Journal of Industrial Health. Vol. 24, Pg. 373, 1982.
 
rat LD50 oral 1650mg/kg (1650mg/kg)   GAF Material Safety Data Sheet.