Furfuryl acrylates

The furfuryl esters of acrylic and methacrylic acid polymerize via a free-radical mechanism without apparent retardation problems arising from the presence of the furan ring. Early reports on these systems described hard insoluble polymers formed in bulk polymerizations and the cross-linking ability of as little as 2% of furfuryl acrylate in the solution polymerization of methylacrylate121. ... 

Finally, addition polymerization of suitably substituted furans allows incorporation of the furan nucleus into heterocyclic polymers (77MH1102). 2-Vinylfuran apparently exhibits free radical polymerizability comparable with that of styrene, although rates, yields and degrees of polymerization are low under all conditions except for emulsion polymerization. Cationic polymerization is quite facile and leads not only to the poly(vinylfuran) structure (59), as found in free radically produced polymers, but also to structures such as (60) and (61) in which the furan nucleus has become involved. Furfuryl acrylate and methacrylate undergo free radical polymerization in the manner characteristic of other acrylic esters. 

Furfural — see Furan-2-carbaldehyde, 532 Furfuryl acetate, a-(butoxycarbonyl)-anodic oxidation, 1, 424 Furfuryl acrylate polymerization, 1, 279 Furfuryl alcohol configuration, 4, 544 2-Furfuryl alcohol polycondensation, 1, 278 reactions, 4, 70-71 Furfuryl alcohol, dihydro-pyran-4-one synthesis from, 3, 815 Furfuryl alcohol, tetrahydro-polymers, 1, 276 rearrangement, 3, 773 Furfuryl chloride reactions... 

Jap. Kokai Tokkyo Koho JP 82 14,670 1982 Hitachi Similar to above but 5-40% tetrahydro-furfuryl acrylate or methacrylate. 

Secondary C—H bonds attached to a single furan ring do not display such a pronounced lability, as shown by polymers like furfuryl acrylates which do not suffer substantial aging. 

Uses are the manufacture of - furan ( tetrahy-drofuran), - furfuryl alcohol, ->methylfuran and nitrofurans, which are intermediates for making antimicrobial reagents. It is also used as a selective solvent in the separation of saturated and unsaturated compounds in lubricating oils, gas oil and diesel fuels, as well as in extractive distillation of CVCs hydrocarbons for manufacturing S3mthetic rubbers. Other uses are as reactive solvent in corrosion-resistant - furfuryl alcohol resins and in high-carbon phenol resins (abrasive wheels and brake linings). Furfuryl acrylate is used as monomer in vinyl-polymerization. 

The versatility of this reaction is extended to a variety of aldehydes. The bisphenol derived from 2,6-di-/ f2 -butylphenol and furfural, (25) where R = furfuryl (13), is also used as an antioxidant. The utility of the 3,5-di-/ f2 -butyl-4-hydroxyben2yl moiety is evident in stabili2ets of all types (14), and its effectiveness has spurred investigations of derivatives of hindered alkylphenols to achieve better stahi1i2ing quaUties. Another example is the Michael addition of 2,6-di-/ f2 -butyl phenol to methyl acrylate. This reaction is carried out under basic conditions and yields methyl... 

Ethoxyethanol 2-Ethoxyethyl acetate Ethyl acrylate Ethylene dinitrate 4-Ethylmorpholine 2-Furaldehyde Furfuryl alcohol Glycerol trinitrate Heptachlor... 

Substituted 3-hydroxy-2-pyrrolidinones were synthesised via 1,3-DC reactions of furfuryl nitrones with acrylates and subsequent intramolecular cyclisation after N-0 bond reduction. Addition of iV-acryloyl-(2/()-bomane-10,2-sultam to Z-nitrone 83 gave the endo/exo cycloadducts in 85 15 ratio with complete stereoface discrimination <00JOC1590>. The 1,3-DC of pyrroline A-oxide to chiral pentenoates using (-)-/rans-2-phenylcyclohexanol and (-)-8-phenylmenthol as chiral auxiliaries occurred with moderate stereocontrol (39% de and 57% de, respectively) and opposite sense of diastereoselectivity <00EJO3595>. The... 

The use of C-furfuryl nitrones by Merino and co-workers (201) as latent carboxylate functionality (see Section 1.7) has inspired the development of an analogous C-thiazolyl nitrone. Thus, after reaction of this dipole with acrylate esters, the authors take advantage of the thiazolyl-to-formyl synthetic equivalence to reveal aldehyde functionality after reduction with sodium cyanoborohydride. 

Furfural Pentose Furfuryl alcohol, furfuryl amine, furan-acrylic acid, tetrahydrofuran, levulinic acid, maleic anhydride Chheda etal., 2007 Corma etal., 2007... 

Whereas 2-hydroxymethylthiophene reacts normally with hydrogen halides to give 2-halomethylthiophenes, reaction of 2-hydroxymethylfuran (furfuryl alcohol) with hydrochloric acid results in formation of levulinic acid 391 via the SN intermediate 390. The conversion of 3-(furan-2-yl)acrylic acid 392 into an ester of -oxopimelic acid 393 by ethanolic hydrochloric acid is a related reaction involving an analogous intermediate. 

Triforine cure accelerator Dipentaerythrityl acrylate cure activator, oxidation butyl rubber Benzothiazyl disulfide cure inhibitor, RTV systems Dimethicone, vinyidimethyl-terminated cure moderator, RTV systems Dimethicone, vinyidimethyl-terminated cure promoter, polyesters Benzene phosphinic acid cure promoter amine-cured epoxies Furfuryl alcohol curing agent... 

In order to study elastomeric networks, simulating the type of polymers used for tires, we switched to polymers with low glass transition temperatures and oligoether bis-maleimides. A typical random copolymer structure, built from the radical copolymerization of n-hexyl acrylate and 2-furfuryl methacrylate, is shown below. These reactions were conducted in toluene at 80°C with AIBN as initiator. After 8 h, the copolymers were recovered by precipitation in 70 to 80% yields. The compositions varied fi om 2 to 30% of the furanic monomer (monomer feed and copolymer composition were always very similar, suggesting that ri and ti must have both been close to unity). The corresponding Tgs went from -70 to 30°C for molecular weights of about 20,000. Both homopolymers were also prepared as reference materials. 

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