Butylphenols

Organic sulfur compounds such as sulfurized spermaceti oil, terpene sulfides, and aromatic disulfides have been used. Encumbered phenols such as di-tertiary-butylphenols and amines of the phenyl-alphanaphthylamine type are effective stopping the kinetic oxidation chain by creating stable radicals. 

Treatment of 2 4 6 tn tert butylphenol with bromine in cold acetic acid gives the compound CigH29BrO in quantitative yield The infrared spectrum of this compound contains absorptions at 1630 and 1655 cm Its H NMR spectrum shows only three peaks (all singlets) at 8 1 2 13 and 6 9 in the ratio 9 18 2 What is a reasonable structure for the compound" ... 

In the 1960—1980 period, the use of more economical synthetic isopropyl- and /-butylphenols as alternatives to cresols was developed (98,99). Commercial triaryl phosphates such as FMC s Kronitex 100 and Ak2o s Phosflex 31P and 41B are based on partially isopropylated or /-butylated phenol. The relative volatihties and oxidative stabiUties of these phosphates have been compared the /-butylphenyl phosphates are the most oxidatively stable of the alkylphenyl phosphates (100). 

Substituted Phenols. Phenol itself is used in the largest volume, but substituted phenols are used for specialty resins (Table 2). Substituted phenols are typically alkylated phenols made from phenol and a corresponding a-olefin with acid catalysts (13). Acidic catalysis is frequendy in the form of an ion-exchange resin (lER) and the reaction proceeds preferentially in the para position. For example, in the production of /-butylphenol using isobutylene, the product is >95% para-substituted. The incorporation of alkyl phenols into the resin reduces reactivity, hardness, cross-link density, and color formation, but increases solubiHty in nonpolar solvents, dexibiHty, and compatibiHty with natural oils. 

Gas chromatography (gc) has been used extensively to analyze phenoHc resins for unreacted phenol monomer as weU as certain two- and three-ring constituents in both novolak and resole resins (61). It is also used in monitoring the production processes of the monomers, eg, when phenol is alkylated with isobutylene to produce butylphenol. Usually, the phenoHc hydroxyl must be derivatized before analysis to provide a more volatile compound. The gc analysis of complex systems, such as resoles, provides distinct resolution of over 20 one- and two-ring compounds having various degrees of methylolation. In some cases, hemiformals may be detected if they have been properly capped (53). 

Phenol. Phenol monomer is highly toxic and absorption by the skin can cause severe blistering. Large quantities can cause paralysis of the central nervous system and death. Ingestion of minor amounts may damage kidneys, Hver, and pancreas. Inhalation can cause headaches, dizziness, vomiting, and heart failure. The threshold limit value (TLV) for phenol is 5 ppm. The health and environmental risks of phenol and alkylated phenols, such as cresols and butylphenols, have been reviewed (66). 

Substituted heat-reactive resins are most widely used in contact-adhesive appHcations and, to a lesser extent, in coatings (77,78) -butylphenol, cresol, and nonylphenol are most frequendy used. The alkyl group increases compatibiHty with oleoresinous varnishes and alkyds. In combination with these resins, phenoHcs reduce water sensitivity. Common appHcations include baked-on and electrical insulation varnishes, and as modifiers for baking alkyds, rosin, and ester gum systems. Substituted heat-reactive resins are not used for air-dry coatings because of theh soft, tacky nature in the uncured state substituted nonheat-reactive phenoHcs are the modifying resin of choice in this case. 

Neoprene—phenohc contact adhesives, known for thein high green strength and peel values, contain a resole-type resin prepared from 4-/-butylphenol. The alkyl group increases compatibiHty and reduces cross-linking. This resin reacts or complexes with the metal oxide, eg, MgO, contained in the formulation, and increases the cohesive strength of the adhesive. In fact, the reactivity with MgO is frequently measured to determine the effectiveness of heat-reactive phenoHcs in the formulation. 

Dialkylphenols employ locants to designate the position of the alkyl groups on the ring. Thus, 2,6-bis(l,l-dimethylethyl)phenol, 2,6-di-/ f2 -butylphenol, and 2,6-DTBP each refer to stmcture (2). 

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