Furfural and derivs

Orcinol—sulphuric acid 200 mg orcinol in 100 ml 10% sulphuric acid Spray Formation of furfural and derivatives with heat and acid which condense with a phenol... 

Uses. Furfural is primarily a chemical feedstock for a number of monomeric compounds and resins. One route produces furan by decarbonylation. Tetrahydrofuran is derived from furan by hydrogenation. Polytetramethylene ether glycol [25190-06-1] is manufactured from tetrahydrofuran by a ring opening polymeri2ation reaction. Another route (hydrogenation) produces furfuryl alcohol, tetrahydrofurfuryl alcohol, 2-methylfuran, and 2-methyltetrahydrofuran. A variety of proprietary synthetic resins are manufactured from furfural and/or furfuryl alcohol. Other... 

Table 3. Toxic Effects of Furfural and Main Derivatives ...

In the acid hydrolysis process (79—81), wood is treated with concentrated or dilute acid solution to produce a lignin-rich residue and a Hquor containing sugars, organic acids, furfural, and other chemicals. The process is adaptable to all species and all forms of wood waste. The Hquor can be concentrated to a molasses for animal feed (82), used as a substrate for fermentation to ethanol or yeast (82), or dehydrated to furfural and levulinic acid (83—86). Attempts have been made to obtain marketable products from the lignin residue (87) rather than using it as a fuel, but currently only carbohydrate-derived products appear practical. 

In some cases, the hydrolysis reaction liberates the sugars from the biomass and converts them directly into derivatives such as furfural, hydroxymethyl furfural and/or levulinic acid. These derivatives can be further converted into various chemical intermediates. We will not discuss these further conversions as they are extensively reported in the literature, e.g., for furfural [15, 44], hydroxymethyl furfural [15, 44, 50] and levulinic acid [15, 44-47]. 

When heated with a strong acid, pentoses and hexoses are dehydrated to form furfural and hydroxymethylfurfural derivatives respectively (Figure 9.20), the aldehyde groups of which will then condense with a phenolic compound to form a coloured product. This reaction forms the basis of some of the oldest qualitative tests for the detection of carbohydrates, e.g. the Molisch test using concentrated sulphuric acid and a-naphthol. 

Among the monomers given in Scheme 1, several possess sufficient nucleophilicity to undergo cationic polymerization (7,8), namely 2-vinyltetrahydrofiiran 1, the alkenylfiirans 2, the furfurylidene ketones 3, 2-furyl oxiranes 4 and the furfuryl vinyl ethers 6, Moreover, furfural and its 5-methyl derivative can act as comonomers in certain cationic copolymerizations. 

The Miner Laboratories, Furfural and its Derivatives, Bull(1928), Chicago, 111... 

Furfurals and its derivatives (except those generally recognised as highly toxic)... 

Of the substances studied the most abundant in the Paleozoic rocks of the area are furfurals presumably derived from carbohydrates, higher molecular weight hydrocarbons, and in a few samples, amino acids. Acid and base soluble, low boiling substances having some properties of heterocyclic compounds, phenols, and organic acids exist in smaller amounts. 

The Dreywood100 anthrone reagent, which gives a positive qualitative test for a large variety of carbohydrates, as well as for furfural and its 5-hydroxymethyl derivative, gives a negative test for 2-desoxyribose.101... 

Pyrroles are derived from heating sugars and amino acids or Amadori intermediates or by heating furfural and a-amino acids. 

The complexes of zinc and cadmium with Schiff bases derived from salicylaldehyde and propan-2-olamine or 2-aminomethylpropanol have been reported,57 as well as their complexes with ethanolamine and propan-2-olamine.58,59 Zinc complexes of stoicheiometry ZnL2X2 have been obtained where L = benzoyl- and salicyl-hydra-zones of vanilline. furfural, and cinnamaldehyde. Zinc complexes of several substituted o-bydroxybutyrophenones and their oximes have been reported.60-62 Complexes of stoicheiometery ZnL2U have been reported where L = the a-nitroketonato-anion obtained from nitroacetone, 3,3-dimethyl-l-nitrobutan-2-one or 3-nitrocam-phor and L — bipyridyl or 1,10-phenanthroline.63... 

Apart from dehydration of glucose or fructose in the presence of alcohols and acid catalysts, synthesis strategies via 5-(chloromethyl)furfural and subsequent heating in the desired alcohol or utilizing furfuryl alcohol as feedstock have been demonstrated [89-98], While 5-(chloromethyl)furfural may be derived in one step based on cellulose, a synthesis procedure starting from furfuryl alcohol utilizes hemicellulose as feedstock, bridging the C5 and C6 carbohydrate value chain. 

Furans. The last statement is certainly true of furans derived from sugars (142,143), particularly furfural and furfuryl alcohol, which is readily derived from furfural (144)- Dr. McKillip of QO Chemicals discusses furan resin chemistry and furan polymers in Chapter 29. Dr. Stanford and his colleagues at the University of Manchester Institute of Science and Technology discuss the use of a diisocyanate derived from furfural for polyurethane production in Chapter 30. 

Furfural (1), derived from annually renewable agricultural byproducts, is an important industrial chemical manufactured and used throughout the world. It is the feedstock for a number of derivative chemicals generically known as furans -the structural characteristic of which is the five-membered oxygen-containing heterocyclic ring. Furfuryl alcohol (2) is the most important derivative of commerce, where it is used primarily in synthesis of adhesive polymers. 

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