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Tetramethylene oxide or oxolane, is an organic compound with the formula (CH2)4O.
The compound is classified as heterocyclic compound, specifically a cyclic ether.
CAS Number: 109-99-9
EC Number: 203-726-8
IUPAC Name: 1,4-Epoxybutane
Chemical Formula: C4H8O
Other names: TETRAHYDROFURAN, 109-99-9, Oxolane, Furan, tetrahydro-, Furanidine, Hydrofuran, Tetramethylene oxide, Oxacyclopentane, 1,4-Epoxybutane, Tetrahydrofuranne, Tetraidrofurano, Tetrahydrofuraan, Tetrahydrofurane, Cyclotetramethylene oxide, THF, tetrahydro-furan, Butane, 1,4-epoxy-, Cyclotetramethylene, RCRA waste number U213, 24979-97-3, NCI-C60560, NSC 57858, Butane .alpha.,.delta.-oxide, Butane alpha,delta-oxide, MFCD00005356, 3N8FZZ6PY4, DTXSID1021328, CHEBI:26911, NSC-57858, Tetrahydrofuran, anhydrous, Agrisynth THF, tetrahydofurane, Tetrahydrofuraan [Dutch], Tetraidrofurano [Italian], Butane, alpha,delta-oxide, Tetrahydrofuranne [French], Tetrahydrofuran, Spectrophotometric Grade, CCRIS 6276, HSDB 125, EINECS 203-726-8, UN2056, RCRA waste no. U213, Tetrahydrofuran(Stabilized), UNII-3N8FZZ6PY4, terahydrofuran, terahydrofurane, terahyrofuran, tetrahydofuran, tetrahydorfuran, tetrahyrdofuran, tetrahyrofuran, tetraliydrofuran, tetra hydrofuran, tetra-hydrofuran, tetrahy-drofuran, tetrahydro furan, tetrahydrof uran, tetrahydrofu ran, tetrahydrofura n, tetrahydrofuran-, AI3-07570, tet-rahydrofurane, tetra-hydrofurane, tetrahydro furane, tetrahydro-furane, tetrahydrofurane-, Tetrahydrofuran, contains 250 ppm BHT as inhibitor, ACS reagent, >=99.0%, tetra hydro-furan, tetra- hydrofuran, tetrahydro- furan, Butane a,d-oxide, Butane,4-epoxy-, Dynasolve 150, Tetrahydrofuran ACS, 1,4-epoxy-Butane, c0019, tetrahydrofuran solvent, THF (tetrahydrofuran), Tetrahydrofuran, 99%, Tetrahydrofuran, Biograde, WLN: T5OTJ, EC 203-726-8, TETRAHYDROFURAN [MI], Tetrahydrofuran Ultra LC-MS, Tetrahydrofuran, ACS reagent, Tetrahydrofuran, >=99.5%, TETRAHYDROFURAN [HSDB], TETRAHYDROFURAN [IARC], Tetrahydrofuran, p.a., 99%, CHEMBL276521, DTXCID501328, TETRAHYDROFURAN [USP-RS], Diethylene oxide 1,4-Epoxybutane, Tetrahydrofuran, UV, HPLC Grade, NSC57858, Tetrahydrofuran, analytical standard, Tox21_201026, STL264218, AKOS000119982, UN 2056, Tetrahydrofuran, for HPLC, >=99.9%, NCGC00090740-01, NCGC00090740-02, NCGC00258579-01, BP-30232, CAS-109-99-9, Tetrahydrofuran, anhydrous, inhibitor free, Tetrahydrofuran, purum, >=99.0% (GC), 1ST001504, DB-038044, NS00009145, T0104, T0856, T2394, EN300-21322, Tetrahydrofuran, SAJ first grade, >=99.0%, Tetrahydrofuran, Selectophore(TM), >=99.5%, Tetrahydrofuran [UN2056] [Flammable liquid], Tetrahydrofuran HPLC grade stabilized with BHT, Tetrahydrofuran, JIS special grade, >=99.5%, Tetrahydrofuran, HPLC grade stabilized with BHT, A802124, InChI=1/C4H8O/c1-2-4-5-3-1/h1-4H, Q278332, Tetrahydrofuran, for HPLC, contains No stabilizer, Tetrahydrofuran, inhibitor-free, purification grade, Tetrahydrofuran, puriss. p.a., >=99.9% (GC), J-002358, Tetrahydrofuran, for luminescence, >=99.5% (GC), Tetrahydrofuran, inhibitor-free, for HPLC, =99.9%, Tetrahydrofuran, anhydrous, >=99.9%, inhibitor-free, Tetrahydrofuran, for HPLC, >=99.9%, inhibitor-free, Tetrahydrofuran, inhibitor-free, for HPLC, >=99.9%, Tetrahydrofuran, anhydrous stabilized, Max. water 20ppm, Tetrahydrofuran, anhydrous stabilized, Max. water 25ppm, Tetrahydrofuran, HPLC grade, >=99.9%, inhibitor-free, Tetrahydrofuran, non-UV, HPLC grade stabilized with BHT, Tetrahydrofuran, biotech. grade, >=99.9%, Inhibitor-free, Tetrahydrofuran, for amino acid analysis, without stabilizer, Tetrahydrofuran, p.a., 99%, contains 200-300 ppm BHT, Tetrahydrofuran, HPLC, UV-IR, isocratic grade, unstabilized, Tetrahydrofuran, anhydrous, inhibitor-free, ZerO2(TM), >=99.9%, Tetrahydrofuran, AR, contains 250 ppm BHT as stabilizer, 99.5%, Tetrahydrofuran, LR, contains 250 ppm BHT as stabilizer, >=99%, Tetrahydrofuran, spectrophotometric grade, >=99.5%, inhibitor-free, Tetrahydrofuran, ACS reagent, >=99.0%, contains 250 ppm BHT as inhibitor, Tetrahydrofuran, anhydrous, >=99.9%, contains 250 ppm BHT as inhibitor, Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, >=99.9%, Tetrahydrofuran, anhydrous, contains 250 ppm BHT as stabilizer, >=99.5%, Tetrahydrofuran, UV HPLC spectroscopic, 99.8%, contains 200-300 ppm BHT, Tetrahydrofuran, Pharmaceutical Secondary Standard; Certified Reference Material, Tetrahydrofuran, ReagentPlus(R), >=99.0%, contains 250 ppm BHT as inhibitor, FU1, Tetrahydrofuran, absolute, over molecular sieve (H2O <=0.005%), contains ~0.025% 2,6-di-tert-butyl-4-methylphenol as stabilizer, >=99.5% (GC), Tetrahydrofuran, contains 250 ppm BHT as inhibitor, puriss. p.a., ACS reagent, Reag. Ph. Eur., >=99.9%, Tetrahydrofuran, Vetec(TM) reagent grade, anhydrous, contains 100 ppm BHT as inhibitor, >=99.8%
Tetramethylene oxide is a colorless, water-miscible organic liquid with low viscosity.
Tetramethylene oxide is mainly used as a precursor to polymers.
Being polar and having a wide liquid range, THF is a versatile solvent.
Production
About 200,000 tonnes of Tetramethylene oxide are produced annually.
The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. Ashland/ISP is one of the biggest producers of this chemical route.
The method is similar to the production of diethyl ether from ethanol.
The butanediol is derived from condensation of acetylene with formaldehyde followed by hydrogenation.
DuPont developed a process for producing THF by oxidizing n-butane to crude maleic anhydride, followed by catalytic hydrogenation.
A third major industrial route entails hydroformylation of allyl alcohol followed by hydrogenation to 1,4-butanediol.
Other methods
THF can also be synthesized by catalytic hydrogenation of furan.
This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced.
THF is thus derivable from renewable resources.
Applications
Polymerization
In the presence of strong acids, THF converts to a linear polymer called poly(tetramethylene ether) glycol (PTMEG), also known as polytetramethylene oxide (PTMO):
n C4H8O → −(CH2CH2CH2CH2O)n−
This polymer is primarily used to make elastomeric polyurethane fibers like Spandex.
About Tetramethylene oxide
Helpful information
Tetramethylene oxide is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 000 tonnes per annum.
Tetramethylene oxide is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses
Tetramethylene oxide is used in the following products: adhesives and sealants, coating products, washing & cleaning products, anti-freeze products, fillers, putties, plasters, modelling clay, finger paints and lubricants and greases.
Other release to the environment of Tetramethylene oxide is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Manufacture
Release to the environment of Tetramethylene oxide can occur from industrial use: manufacturing of the substance and formulation of mixtures.
Tetramethylene oxide appears as a clear colorless liquid with an ethereal odor. Less dense than water. Flash point 6°F. Vapors are heavier than air.
General description
Tetramethylene oxide (THF) is a saturated cyclic ether with a potential use as a biofuel. Its combustion studies have been investigated.
Reports suggest that it is a better promoter than 1,3 dioxolane for CO2-hydrate formation.
THF is used as a component in mobile phases for reversed-phase liquid chromatography. It has a greater elution strength than methanol or acetonitrile, but is less commonly used than these solvents.
THF is used as a solvent in 3D printing when using PLA plastics.
Tetramethylene oxide can be used to clean clogged 3D printer parts, as well as when finishing prints to remove extruder lines and add a shine to the finished product.
Recently THF is used as co-solvent for lithium metal batteries, helping to stabilize the metal anode.
Laboratory use
In the laboratory, THF is a popular solvent when its water miscibility is not an issue.
Tetramethylene oxide is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.
Tetramethylene oxide is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.
Thus, while diethyl ether remains the solvent of choice for some reactions (e.g., Grignard reactions), THF fills that role in many others, where strong coordination is desirable and the precise properties of ethereal solvents such as these (alone and in mixtures and at various temperatures) allows fine-tuning modern chemical reactions.
Commercial THF contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds.
Although THF is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.
Reaction with hydrogen sulfide
In the presence of a solid acid catalyst, THF reacts with hydrogen sulfide to give tetrahydrothiophene.
Precautions
THF is a relatively nontoxic solvent, with the median lethal dose (LD50) comparable to that for acetone.
Reflecting its remarkable solvent properties, it penetrates the skin, causing rapid dehydration.
THF readily dissolves latex and thus should be handled with nitrile rubber gloves.
Tetramethylene oxide is highly flammable.
As a solvent
The other main application of THF is as an industrial solvent for polyvinyl chloride (PVC) and in varnishes.
Tetramethylene oxide is an aprotic solvent with a dielectric constant of 7.6.
Tetramethylene oxide is a moderately polar solvent and can dissolve a wide range of nonpolar and polar chemical compounds.
THF is water-miscible and can form solid clathrate hydrate structures with water at low temperatures.
THF has been explored as a miscible co-solvent in aqueous solution to aid in the liquefaction and delignification of plant lignocellulosic biomass for production of renewable platform chemicals and sugars as potential precursors to biofuels.
Aqueous THF augments the hydrolysis of glycans from biomass and dissolves the majority of biomass lignin making it a suitable solvent for biomass pretreatment.
THF is often used in polymer science. For example, it can be used to dissolve polymers prior to determining their molecular mass using gel permeation chromatography.
THF dissolves PVC as well, and thus it is the main ingredient in PVC adhesives. It can be used to liquefy old PVC cement and is often used industrially to degrease metal parts.
Tetramethylene oxide (THF) is a colorless, volatile liquid with an ethereal or acetonelike smell and is miscible in water and most organic solvents.
Tetramethylene oxide is highly flammable and may thermally decompose to carbon monoxide and carbon dioxide.
Prolonged storage in contact with air and in the absence of an antioxidant may cause THF to decompose into explosive peroxides.
Molar mass: 72.107g
Appearance: Colorless liquid
Odor: Ether-like
Density: 0.8876 g/cm3 at 20 °C, liquid
Melting point: −108.4 °C (−163.1 °F; 164.8 K)
Boiling point: 66 °C (151 °F; 339 K)
Solubility in water: Miscible
Vapor pressure: 132 mmHg (20 °C)
Refractive index (nD): 1.4073 (20 °C)
Viscosity: 0.48 cP at 25 °C
XLogP3: 0.5
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count: 1
General description
Tetramethylene oxide (THF) is a saturated cyclic ether with a potential use as a biofuel.
Tetramethylene oxides combustion studies have been investigated.
Reports suggest that Tetramethylene oxide is a better promoter than 1,3 dioxolane for CO2-hydrate formation.
What is Tetramethylene oxide used for?
Industry Uses
Tetramethylene oxide has many industry uses as a solvent including in natural and synthetic resins, high polymers, fat oils, rubber, polymer and protective coating, adhesives, inks, tetramethyl lead, PVC and in the production of nylon and adipic acid.
Tetramethylene oxide is also used as a reaction medium, primarily in the pharmaceutical industry, in processes such as Grignard syntheses or lithium aluminium hydride reductions.
Grignard synthesis examples include butyrolactone and succinic acid.
Tetramethylene oxide is also used as a Grignard reagent in the synthesis of synthetic perfumes, pharmaceuticals, motor fuels and insecticides.
Tetramethylene oxide is a valuable chemical intermediate as Tetramethylene oxide is a precursor to polymers, such as poly (tetramethylene ether) glycol.
The primary use of this polymer is the production of elastomeric polyurethane fibres like Spandex.
Tetramethylene oxide is also an intermediate in the natural gas industry where Tetramethylene oxide is a natural gas odorant.
Other industry uses include in intermediates, processing aids and plasticisers.
Commercial Uses
Commercial uses of Tetramethylene oxide include in adhesives, paints and coatings and solvents.
Application
Tetramethylene oxide was used as a solvent in the formation of diacetylinic polymers.
Exact Mass: 72.057514874
Monoisotopic Mass: 72.057514874
Topological Polar Surface Area: 9.2 Ų
Heavy Atom Count: 5
Complexity: 22.8
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Adhesives features/benefits:
Rapid uniformbit into substrates, hogh volatile, solvency, minimize gelling and contributes to bonding strength
coatings & inks application
magnetic recording media - used as solvent for magnetizable oxide and binder for resin for polyester and cellulose acetate tapes
vinyl fabric and sheeting coatings - solvent for high molecular PVC resins
PVC printing inks - use as co-solvent for promote adhesion of inks
coatings and inks features/benefits
provides uniform coating thickness and rapid drying
forms solution with high solids and practical woking viscosities
provides good viscosity and rheology control, reduces smearing
Tetramethylene oxide (THF, oxolane) is a versatile solvent used in laboratory organic synthesis and in industrial products such as varnishes. It is colorless and miscible in water, with a boiling point of 66 ºC. It is highly flammable but relatively nontoxic. When stored in air, it can form explosive peroxides, but this can be prevented by adding an inhibitor such as butylated hydroxytoluene (BHT).
In 1956, W. W. Gilbert and B. W. Howk at Du Pont patented the catalytic hydrogenation of maleic anhydride to produce THF.
Du Pont later patented a process for hydrogenating furan to THF. Today the predominant THF manufacturing process is the acid-catalyzed dehydration of 1,4-butanediol.
More than two dozen US patents on this process were issued between 1975 and 2007.
Tetramethylene oxide — CH2CH2CH2CH2O — is a cyclic organic compound known for its solvency and cyclic ether structure.
It is also known as THF, Oxolane, Furan, Butylene oxide, Cyclotetramethylene oxide, Diethylene oxide, and Tetra-methylene oxide.
THF is typically a colorless organic liquid that is both water-miscible and low viscosity. Because of its polar nature and broad liquid range, THF serves as one of the most useful organic solvents on the market today.
Tetramethylene oxide (THF) is produced by dehydration of 1,4-butanediol. It is a neutral, colorless, volatile cycloaliphatic ether.
It is highly polar and miscible with water. As an aprotic and medium polarity solvent, Tetramethylene oxide is an excellent solvent for many organic substances. The chemical formula of this cyclic ether is (CH2)4O.
Tetramethylene oxide (THF) is a contaminant of exposure and appears in human biofluids.
The Food and Drug Administration (FDA) has announced recommendations to revise the permitted daily exposures for THF, and so has the International Conference on Harmonisation.
THF oxidizes readily, which can lead to instability and result in cytotoxicity.
It is a colourless low-viscosity liquid with a smell similar to diethyl ether and is one of the most polar ethers.
Tetramethylene oxide is essentially considered in occupational toxicology, and acute poisoning cases are extremely rare. THF is often used for hydroborations used to synthesize primary alcohols.
THF is often used as a solvent for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent (an organometallic chemical reaction involving alkyl- or aryl-magnesium halides).
THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. THF tends to form peroxides on storage in air.
How is Tetramethylene oxide produced?
Reppe Process
Tetramethylene oxide was traditionally produced using the Furfural process where furfural, extracted from corn husks, is used as the raw material in production.
However, the disadvantage of this method is that supply depended on agricultural conditions and could not therefore be relied upon, so a move was made to the fully synthetic Reppe process.
In the Reppe process, ethyne and formaldehyde are used as the raw materials that produce 1,4-butanediol, at the first step.
Tetramethylene oxide can then be obtained via the acid-catalyzed dehydration of 1,4-butanediol in the presence of an acidic ion exchange resin.
This is currently the main method of extraction employed throughout the world.
A second major industrial method of manufacturing THF is the hydroformylation of allyl alcohol followed by the subsequent hydrogenation to resulting in 1,4-butanediol.
Oxidisation of n-butane
Another method is a two-step butadiene chlorination process that yields 70-75% THF.
Developed by DuPont, Tetramethylene oxide involves oxidising n-butane to create maleic anhydride followed by catalytic hydrogenation over a palladium catalyst.
Tetramethylene oxide is a relatively simple process and one that is of interest to chemical producers.
Catalytic hydrogenation of furan
Tetramethylene oxide can also be produced, or synthesised, via catalytic hydrogenation of furan.
This process involves converting certain sugars into THF by digesting to furfural.
An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.
Other methods include the decarboxylation of furfural and the oxidisation of butadiene.
The world annual production of Tetramethylene oxide is approximately 200,000 tonnes and Tetramethylene oxide is predicted that demand and production will grow as the Chinese economy continues to expand.
Tetramethylene oxide is used in the manufacture of polymers as well as agricultural, pharmaceutical, and commodity chemicals.
Manufacturing activities commonly occur in closed systems or under engineering controls that limit worker exposure and release to the environment.
THF is also used as a solvent (e.g., pipe fitting) that may result in more significant exposures when used in confined spaces without sufficient ventilation.
Although THF is naturally present in coffee aroma, floured chickpeas, and cooked chicken, natural exposures are not anticipated to pose a significant hazard.
Chemical Properties
Tetramethylene oxide (THF) is an industrial solvent widely recognized for its unique combination of useful properties.
DuPont THF is better than 99.9% pure with a small (0.025-0.040 wt % ) amount of butylated hydroxytoluene (BHT, 4-methyl-2,6-di-tertbutyl phenol) added as an antioxidant.
Tetramethylene oxide is a cycloaliphatic ether and is not "photochemically reactive" as defined in Section k of Los Angeles County's Rule 66 (equivalent to Rule 442 of the Southern California Air Pollution Control District).
THF has an ethereal odor.
The Odor Threshold is listed @ 3.8 (3M), 20-50ppm, and 31ppm.
Tetramethylene oxide is also a common laboratory reagent and an intermediate in chemical syntheses of consumer and industrial products such as nutritionals, pharmaceuticals, and insecticides.
Physical properties
Tetramethylene oxide is a clear, colourless liquid with a strong ether-like odour.
Odor threshold concentration is 2 ppm.
Tetramethylene oxide is highly flammable. Contact of Tetramethylene oxide with strong oxidising agents may cause explosions.
Tetramethylene oxide may polymerise in the presence of cationic initiators.
Contact with lithium–aluminium hydride, with other lithium–aluminium alloys, or with sodium or potassium hydroxide can be hazardous.
Uses
Butylene oxide is used as a fumigant and inadmixture with other compounds.
Tetramethylene oxide is usedto stabilize fuel with respect to color andsludge formation.
Uses
Tetramethylene oxide is used as a solvent forresins, vinyls, and high polymers; as a Grignardreaction medium for organometallic,and metal hydride reactions; and in the synthesisof succinic acid and butyrolactone.
Uses
Solvent for high polymers, especially polyvinyl chloride.
As reaction medium for Grignard and metal hydride reactions.
In the synthesis of butyrolactone, succinic acid, 1,4-butanediol diacetate.
Solvent in histological techniques.
May be used under Federal Food, Drug & Cosmetic Act for fabrication of articles for packaging, transporting, or storing of foods if residual amount does not exceed 1.5% of the film: Fed. Regist. 27, 3919.
Uses
Tetramethylene oxide is used primarily (80%) to make polytetramethylene ether glycol, the base polymer used primarily in the manufacture of elastomeric fibers (e.g., spandex) as well as polyurethane and polyester elastomers (e.g., artificial leather, skateboard wheels).
The remainder (20%) is used in solvent applications (e.g., pipe cements, adhesives, printing inks, and magnetic tape) and as a reaction solvent in chemical and pharmaceutical syntheses.
Definition
ChEBI: A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.
General Description
A clear colorless liquid with an ethereal odor.
Less dense than water.
Flash point 6°F.
Vapors are heavier than air.
Air & Water Reactions
Highly flammable.
Oxidizes readily in air to form unstable peroxides that may explode spontaneously.
Soluble in water.
Reactivity Profile
Tetramethylene oxide reacts violently with oxidizing agents leading to fires and explosions.
Subject to peroxidation in the air.
Peroxides or their products react exothermically with lithium aluminum hydride.
Thus, use as a solvent for lithium aluminum hydride has led to fires.
Using potassium hydroxide or sodium hydroxide to dry impure Tetramethylene oxide that contains peroxides has resulted in explosions.
A violent explosion occurred during the preparation of sodium aluminum hydride from sodium and aluminum in a medium of Tetramethylene oxide.
THF forms explosive products with 2-aminophenol.
In sequential deposition method of lead-halide perovskite material, the PbI2 layer morphology and remnant PbI2 play an important role in enhancing the power conversion efficiency (PCE) of the perovskite solar cell.
However, humidity levels affect the PbI2 and perovskite film morphology, resulting in defect sites and recombination centers on the surface and within the bulk of the material, thus impeding the overall device performance and stability.
To address this, incorporation of Tetramethylene oxide (THF) additive in PbI2–dimethylformamide (DMF) precursor solution is reported, to improve the quality of PbI2 thin films and to prevent the water interaction directly with PbI2 under high humidity environments.
The O-donor THF interacts with PbI2, resulting in a homogeneous, dense, and pinhole-free layer as compared with the PbI2 layer without additive.
The perovskite layer so obtained from the pinhole-free PbI2 layer is compact, resulting in a significant reduction of defects/traps.
The device is fabricated with modified perovskite in ≈50% humidity atmosphere, resulting in 15% efficiency with high reproducibility.
Moreover, the THF-modified non-encapsulated perovskite device retains 80% PCE after exposure to 50% relative humidity for 20 days.
A strategy to fabricate perovskite solar cells, with reproducible efficiency in high humidity atmosphere viable for large-scale production, is demonstrated.
Tetramethylene oxide (THF) is a versatile chemical that has commercial application as a solvent for the manufacture of plastics and is closely related to 1,4-butanediol (BDO) and γ-butyrolactone (GBL).
Since THF polymers (PolyTHF and PTMEG) are also major commercial products, further investigation into the application of these products will be of great interest, particularly for the potential production of THF from furfural in this co-solvent strategy.
THF owes its excellent solvent properties to the polar oxygen in its ring and dispersive character from the four methylene groups.
In a binary mixture with water, the dispersive character of THF increases with increasing THF content in the aqueous phase.
THF is also an excellent extracting solvent for furfural and 5-hydroxymethylfurfural (HMF), and its affinity for these aldehydes may play a key role in its ability to improve their yields in our single-phase system.
THF can also be used to solubilize extracted lignin products from organosolv or ionic-liquid pretreatment strategies or directly used to fractionate raw biomass as with our single-phase process.
Furfural is typically synthesized by acid-catalyzed dehydration of C5 sugars (arabinoseand xylose) whereas levulinic acid (LA) can be derived from either C529 or C6 sugars1 15 (glucose, galactose, and mannose).
Water-soluble Brønsted acids such as HCl and H2SO4 have typically been used to catalyze such dehydration reactions, but homogeneous and heterogeneous solid acid catalysts have also been applied successfully.
Furfural is targeted in this paper as one of the only natural precursors to furan-based chemicals.
However, Tetramethylene oxides low commercial yields (~50% of theoretical) from xylan-rich lignocellulosic residues23 20 hinder Tetramethylene oxides economic potential, and new approaches are needed to make it economically viable as a fuel precursor.
HMF is an important platform chemical that can be produced from the acid-catalyzed dehydration of hexoses.
HMF will readily hydrolyze to form equimolar amounts of LA and formic acid (FA)1 23 in the presence of
Electronic Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2013 a strong acid.
Since LA is more stable than HMF in an aqueous environment,1 1 higher final yields 2 of LA were observed in single phase reactions with sulfuric acid.
Room temperature liquid densities after the 40 min reactions (0.989 kg L-1 3 with 1:1 THF and 1.015 kg L-1 4 without THF at 21 °C) accounted for a 3% difference in the maximum furfural yield.
For both solvent and non-solvent reactions in Table 1, the highest furfural yield was achieved much sooner (40 min) than the highest LA yield (120 min).
Due to the more acid labile amorphous structure of hemicellulose, the rate of hydrolysis of xylan from hemicellulose was much greater than that of glucan from crystalline cellulose.
By increasing the ratio of THF to 3:1 (density: 0.935 kg L-1 9 ), co-production yields of furfural, HMF, and LA improved with increased solubilisation of biomass without significant furfural losses.
Film Casting
THF is used for vinyl chloride heat-shrinkable film and for desiccant.
Printing Inks
THF is suitable for printing inks, because slightly soluble inorganic compounds can be dissolved and evaporation is quick.
Other Uses
THF is widely used as a solvent for special resins such as photosensitive resins, because even at room temperature it can dissolve various resins, and it is miscible with water and most organic solvents. In, addition, it is used as a solvent for Grignard and Wittig reactions. Also in pharmaceutical and agricultural manufacturing, it is used as a solvent for reaction and purification.
THF (Tetramethylene oxide) is a stable compound with relatively low boiling point and excellent solvency.
Tetramethylene oxide is widely-used for dissolution and reaction of various substances.
Also it is used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.
Storage and Handling
THF is classified under the Japanese Fire Services Act as a hazardous material, Class 4, Petroleums No.1, water soluble, Hazardous Rank II.
Since it is highly volatile and flammable, the storage container should be tightly sealed and stored in a well-ventilated place.
When handling take precautions against fire.
Like other ethers, explosive peroxides will be generated if THF is exposed to oxygen or air.
For this reason the container should be sealed with dry nitrogen.
THF is irritating to the membranes and skin of the eyes, nose, and throat.
Exposure to the vapor for long time periods may cause organic solvent poisoning symptoms such as nausea and dizziness.
Use adequate ventilation to avoid high concentrations of vapor.
When using or handling, always use proper safety equipment such as protective gloves and goggles.
Tetramethylene oxide is an organic, polar, water-miscible, cyclic ether and aprotic solvent with low viscosity.
Available in various quantities, purities, and reagent grades, it has applications including use in polymer science and reversed phase chromatography.
Tetramethylene oxide (THF) solvent is an inert, versatile solvent offering high solvency power for numerous organic substances.
It is used as a starting reagent in many syntheses.
adhesives application
Solvent for PVC, polyurethane, polycarbonate, acetate, thermoplastics for adhesives/cements.
Application
Tetramethylene oxide was used as a solvent in the formation of diacetylinic polymers.
Tetramethylene oxide may be used in the following processes:
Formation of butyrolactone (BTL) by green oxidation method.
Aqueous THF solution to modify the polystyrene surface by swelling process.
As a solvent for lignin depolymerization to isolate phenolic monomer.
Surface Coating
Due to the strong solubility of vinyl chloride, even at a high degree of polymerization, THF is used as a solvent for synthetic leather coatings.
Adhesives
Taking advantage of excellent solubility and diffusion properties, THF is used as a solvent for vinyl and epoxy adhesives.
Other release to the environment of Tetramethylene oxide is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
Tetramethylene oxide can be found in complex articles, with no release intended: electrical batteries and accumulators.
Widespread uses by professional workers
Tetramethylene oxide is used in the following products: coating products, laboratory chemicals, washing & cleaning products, metal surface treatment products, metal working fluids and fuels.
Tetramethylene oxide is used in the following areas: printing and recorded media reproduction, health services and scientific research and development.
Tetramethylene oxide is used for the manufacture of: machinery and vehicles, fabricated metal products, plastic products and chemicals.
Other release to the environment of Tetramethylene oxide is likely to occur from: outdoor use, indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).
Formulation or re-packing
Tetramethylene oxideis used in the following products: washing & cleaning products, pharmaceuticals, coating products, polymers and laboratory chemicals.
Release to the environment of this substance can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industry
Tetramethylene oxide is used in the following products: washing & cleaning products, laboratory chemicals, coating products, polymers, pharmaceuticals and metal working fluids.
Tetramethylene oxide has an industrial use resulting in manufacture of another substance (use of intermediates).
Tetramethylene oxide is used in the following areas: formulation of mixtures and/or re-packaging.
Tetramethylene oxide is used for the manufacture of: chemicals.
Release to the environment of Tetramethylene oxide can occur from industrial use: in processing aids at industrial sites, of substances in closed systems with minimal release and as an intermediate step in further manufacturing of another substance (use of intermediates).
