Furans, properties

The most important physical properties of furfural, as well as similar properties for furfuryl alcohol, tetrahydrofurfuryl alcohol and furan are given in Table 1. The tabulated properties of furfural are supplemented by a plot (Fig. 1) of the vapor—Hquid compositions for the system, furfural—water (15,16). 

Furfural is very thermally stable in the absence of oxygen. At temperatures as high as 230°C, exposure for many hours is required to produce detectable changes in the physical properties of furfural, with the exception of color (17). However, accelerating rate calorimetric data shows that a temperature above 250°C, in a closed system, furfural will spontaneously and exothermically decompose to furan and carbon monoxide with a substantial increase in pressure. The pressure may increase to 5000 psi or more, sufficient to shatter the container (18). 

Corrosion Resistant Fiber-Reinforced Plastic (FRP). Fiber glass reinforcement bonded with furfuryl alcohol thermosetting resias provides plastics with unique properties. Excellent resistance to corrosion and heat distortion coupled with low flame spread and low smoke emission are characteristics that make them valuable as laminating resins with fiber glass (75,76). Another valuable property of furan FRP is its strength at elevated temperature. Hand-layup, spray-up, and filament-win ding techniques are employed to produce an array of corrosion-resistant equipment, pipes, tanks, vats, ducts, scmbbers, stacks, and reaction vessels for industrial appHcations throughout the world. 

The inherent fire resistance and low smoke properties of furan resins appear to be related to the high degree of charring that takes place with minimum evolution of volatiles when exposed to fire. 

Physical Properties. Furan, a colorless Hquid with a strong ethereal odor, is low-boiling and highly flammable. It is miscible with most common organic solvents but only very slightly soluble in water. The physical properties of furan are Hsted in Table 1. 

Pyrrohdine [123-75-1] (tetrahydropyrrole) (19) is a water-soluble strong base with the usual properties of a secondary amine. An important synthesis of pyrrohdines is the reaction of reduced furans with excess amine or ammonia over an alumina catalyst in the vapor phase at 400°C. However, if labde substituents are present on the tetrahydrofurans, pyrroles may form (30). 

As might be anticipated from the behaviour of the parent heterocycles, C-2 of indole, benzo[i]furan and benzo[i]thiophene (Table 13) is shifted to lower field than C-3. However, the shifts for C-2 (O, 144.8 Se, 128.8 S, 126.1 NH, 124.7 Te, 120.8) and C-7a (O, 155.0 Se, 141.3 S, 139.6 NH, 135.7 Te, 133.0) in the benzo[i] heterocycles vary irregularly (80OMR(l3)3l9), and the sequence is different to that observed for C-2 in the parent heterocycles, namely 0>Se>Te>S>NH. Also noteworthy is the upheld position of C-7, especially in indole and benzofuran, relative to the other benzenoid carbons at positions 4, 5 and 6. A similar situation pertains in the dibenzo heterocycles (Table 14), where not only are C-1 and C-8 shifted upheld in carbazole and dibenzofuran relative to the corresponding carbons in dibenzothiophene and fluorene, but similar, though smaller, shifts can be discerned for C-3 and C-6 in the former compounds. These carbon atoms are of course ortho and para to the heteroatom and the shifts reflect its mesomeric properties. Little variation in the carbon-hydrogen coupling constants is observed for these dibenzo compounds with V(qh) = 158-165 and V(c,h) = 6-8 Hz. 

Benzo[b]furan, 2-aryl-2,3-dihydro- H NMR, 4, 570 Benzo[b]furan, 2-bromo-nitration, 4, 604 Benzo[b]furan, 5-cinnamoyl-properties, 4, 708 Benzo[b]furan, 2-cyano-photochemical reactions, 4, 636 Benzo[b]furan, 2,3-dialkyl-synthesis, 4, 710 Benzo[b]furan, 2,3-dihydro-aromaticity... 

Benzo[b]furan, 3-(2-hydroxy-3,5-dichlorophenyl)-5,7-dichloro-properties, 4, 708 Benzo[b]furan, 2-lithio-synthesis, 4, 652 Benzo[i]furan, 3-lithio-ring opening, 4, 79 Benzo[b]furan, methoxy-mass spectrometry, 4, 583 Benzo[b]furan, 6-methoxy-2,3-diphenyl-synthesis, 4, 679... 

Furan-2-carbonyl chloride, 5-alkyl-3,4-dichloro-synthesis, 4, 690 Furancarboxamides rotational isomerism, 4, 543 Furan-2-carboxylic acid, 5-acetylamino-ethyl ester reactions, 4, 647 Furan-2-carboxylic acid, amino-properties, 4, 708 Furan-2-carboxylic acid, 5-bromo-nitration, 4, 603, 711 Furan-2-carboxylic acid, 3-methyl-methyl ester bromination, 4, 604 Furan-2-carboxylic acid, 5-methyl-nitration, 4, 602... 

Because of their favourable price, polyesters are preferred to epoxide and furane resins for general purpose laminates and account for at least 95% of the low-pressure laminates produced. The epoxide resins find specialised uses for chemical, electrical and heat-resistant applications and for optimum mechanical properties. The furane resins have a limited use in chemical plant. The use of high-pressure laminates from phenolic, aminoplastic and silicone resins is discussed elsewhere in this book. 

The principal applications for furan resins are in chemical plant. Specific uses include the lining of tanks and vats and piping and for alkali-resistant tile cements. The property of moisture resistance is used when paper honeycomb structures are treated with furan resins and subsequently retain a good compression strength even after exposure to damp conditions. 

PCBS (polychlorinated biphenyls) Toxic synthetic chemicals with excellent heat resistance and low electrical conductivity properties. Now little used but considerable quantities remain in old electrical equipment. Produces dioxins and polychlorinated dibenzo-furans when burned below 1200°C. PCBs are toxic and bio-accumulative. 

The highest mechanical strengths are usually obtained when the fibre is used in fine fabric form but for many purposes the fibres may be used in mat form, particularly glass fibre. The chemical properties of the laminates are largely determined by the nature of the polymer but capillary attraction along the fibre-resin interface can occur when some of these interfaces are exposed at a laminate surface. In such circumstances the resistance of both reinforcement and matrix must be considered when assessing the suitability of a laminate for use in chemical plant. Glass fibres are most commonly used for chemical plant, in conjunction with phenolic resins, and the latter with furane, epoxide and, sometimes, polyester resins. 

As shown by several investigations [91], the bromine-rich polybromide phase by itself is hardly flammable and fireextinguishing properties have been reported occasionally. The formation of polybrominated dibenzo-dioxins (PBrDD) and furans (PBrDF) due to the plastic-containing housing of a zinc-flow battery cannot be totally neglected in the case of a fire, but their concentrations are far away from the tetrachloro dibenzodioxine (TCDD) toxic equivalents even in a worst-case scenario. 

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