Phenol sources

SHAHIDI F and NACZK M (1995) Food Phenolics. Sources, chemistry, effects, applications. Technomics Publ Co, Basel. 

Shahidi, F. and Naczk, M., Pood Phenolics Sources Chemistry Effects Applications, Technomic Publishing Inc., Lancaster, PA, 1995. 

Shahidi F. Naczk M. In Food Phenolics Sources, Chemistry, Effects, Application Lancaster PA Technomic Publishing Co. Inc., 1995 pp. 75-101. 

F. Shahidi and M. Naczk, Food Phenolics Sources, Chemistry, Ejfects and Applications, CRC Press, Boca Raton, Florida, 1994, pp. 9, 53, 75, 109. 

Synonym 2-(1,1-Dimethylethyl)phenol Source Walther, D. Maurer, G. 

Synonym 5-Methyl-2-(1 -methylethyl)phenol Source Mukhopadhyay, M. De, S. K. 

Thiophenols can be readily derived from phenolic sources by a number of processes (ref, 120). They are reactive and are susceptible to a variety of reactions either at the sulphur atom or the ring. 

The phenolic lipids of Anacardieum occidentale have been commercially exploited (ref. 174) and those in Rhus vernicifera to a lesser extent. Most of the technical cashew nut shell liquid (CNSL) which results from industrial processing is and has been employed as a phenolic source for formaldehyde polymerisation the products from which in compounded form have been the basis for friction dusts widely used throughout the world in vehicle brake and clutch linings (ref.175). Urushiol has had use over many centuries in the art of Japanese lacquering (ref. 176) and in more recent years has been sometimes supplemented with CNSL. Chemical uses are referred to later. 

Table 1. Summary of trivial and scientific names, and various physical data of selected substituted phenols (source refs. [21,22]) ...

Shahidi F, Nacsk M (1995) Food phenolics sources, chtanistry, effects and application. Technomic Publ, Lancastru... 

As expected, suitable selection of a metal combination for each targeted reaction was important to achieve high stereoselectivity. For a sy -selective nitro-Maimich-type reaction, a heterobimetallic complex prepared from Cu(OAc)2, Sm(0-/Pr)3, and dinucleating Schiff base la was the best [12]. Other metal combinations resulted in much lower selectivity. Either Cu or Sm alone also resulted in poor reactivity and selectivity. Thus, both Cu and Sm are essential for high catalytic activity and selectivity. After optimization studies, the addition of achiral phenol source and the use of oxo-samarium alkoxide, Sm50(0-jPr)i3, with a well-ordered structure, gave the superior reactivity and stereoselectivity. Under the optimized reaction cmiditions, 1-10 mol% of the Cu/Sm catalyst promoted asymmetric... 

The controlled thermal decomposition of dry aromatic diazonium fluoborates to yield an aromatic fluoride, boron trifluoride and nitrogen is known as the Schiemann reaction. Most diazonium fluoborates have definite decomposition temperatures and the rates of decomposition, with few exceptions, are easily controlled. Another procedure for preparing the diazonium fluoborate is to diazotise in the presence of the fluoborate ion. Fluoboric acid may be the only acid present, thus acting as acid and source of fluoborate ion. The insoluble fluoborate separates as it is formed side reactions, such as phenol formation and coupling, are held at a minimum temperature control is not usually critical and the temperature may rise to about 20° without ill effect efficient stirring is, however, necessary since a continuously thickening precipitate is formed as the reaction proceeds. The modified procedure is illustrated by the preparation of -fluoroanisole ... 

Phenol was first isolated m the early nineteenth century from coal tar and a small por tion of the more than 4 billion lb of phenol produced m the United States each year comes from this source Although significant quantities of phenol are used to prepare aspirin and dyes most of it is converted to phenolic resins used m adhesives and plastics... 

One-Stage Resins. The ratio of formaldehyde to phenol is high enough to allow the thermosetting process to take place without the addition of other sources of cross-links. 

Two-Stage Resins. The ratio of formaldehyde to phenol is low enough to prevent the thermosetting reaction from occurring during manufacture of the resin. At this point the resin is termed novolac resin. Subsequently, hexamethylenetetramine is incorporated into the material to act as a source of chemical cross-links during the molding operation (and conversion to the thermoset or cured state). 

Bromination can be conveniently effected by transfer of bromine from one nucleus to another. As the Friedel-Crafts isomerization of bromoaromatic compounds generally takes place through an intermolecular mechanism, the migrating bromine atom serves as a source of positive bromine, thus effecting ring brominations (161,162). 2,4,6-Tribromophenol, for example, has been prepared by bromination of phenol with dibromobenzene. 

The conditions of pyrolysis either as low or high temperature carbonization, and the type of coal, determine the composition of Hquids produced, known as tars. Humic coals give greater yields of phenol (qv) [108-95-2] (up to 50%), whereas hydrogen-rich coals give more hydrocarbons (qv). The whole tar and distillation fractions are used as fuels and as sources of phenols, or as an additive ia carbonized briquettes. Pitch can be used as a biader for briquettes, for electrode carbon after coking, or for blending with road asphalt (qv). 

Polymers. AH nitro alcohols are sources of formaldehyde for cross-linking in polymers of urea, melamine, phenols, resorcinol, etc (see Amino RESINS AND PLASTICS). Nitrodiols and 2-hydroxymethyl-2-nitro-l,3-propanediol can be used as polyols to form polyester or polyurethane products (see Polyesters Urethane polymers). 2-Methyl-2-nitro-l-propanol is used in tires to promote the adhesion of mbber to tire cord (qv). Nitro alcohols are used as hardening agents in photographic processes, and 2-hydroxymethyl-2-nitro-l,3-propanediol is a cross-linking agent for starch adhesives, polyamides, urea resins, or wool, and in tanning operations (17—25). Wrinkle-resistant fabric with reduced free formaldehyde content is obtained by treatment with... 

Ammonia is used in the fibers and plastic industry as the source of nitrogen for the production of caprolactam, the monomer for nylon 6. Oxidation of propylene with ammonia gives acrylonitrile (qv), used for the manufacture of acryHc fibers, resins, and elastomers. Hexamethylenetetramine (HMTA), produced from ammonia and formaldehyde, is used in the manufacture of phenoHc thermosetting resins (see Phenolic resins). Toluene 2,4-cHisocyanate (TDI), employed in the production of polyurethane foam, indirectly consumes ammonia because nitric acid is a raw material in the TDI manufacturing process (see Amines Isocyanates). Urea, which is produced from ammonia, is used in the manufacture of urea—formaldehyde synthetic resins (see Amino resins). Melamine is produced by polymerization of dicyanodiamine and high pressure, high temperature pyrolysis of urea, both in the presence of ammonia (see Cyanamides). 

Quinone dioximes, alkylphenol disulfides, and phenol—formaldehyde reaction products are used to cross-link halobutyl mbbers. In some cases, nonhalogenated butyl mbber can be cross-linked by these materials if there is some other source of halogen in the formulation. Alkylphenol disulfides are used in halobutyl innerliners for tires. Methylol phenol—formaldehyde resins are used for heat resistance in tire curing bladders. Bisphenols, accelerated by phosphonium salts, are used to cross-link fluorocarbon mbbers. 

Dyes. Sodium nitrite is a convenient source of nitrous acid in the nitrosation and diatozation of aromatic amines. When primary aromatic amines react with nitrous acid, the intermediate diamine salts are produced which, on coupling to amines, phenols, naphthols, and other compounds, form the important azo dyes (qv). The color center of the dye or pigment is the -N=N- group and attached groups modify the color. Many dyes and pigments (qv) have been manufactured with shades of the entire color spectmm. 

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