F-octylphenol

High resolution (HR)-GC chromatograms of NP show a complicated isomer profile [46] with several tens of peaks (see Fig. 2.1.5(b), top). In contrast, commercial standards of OP are usually made up from f-octylphenol [p-(l,l,3,3-tetramethylbutyl)phenol], which is essentially... 

Fig. 2.3.5. Normal-phase HPLC chromatograms of commercial standards of (b) f-octylphenol and (a) 4-nonylphenol (85%). Column 100 X 4.6 mm2 Hypersil 3 NH2 (3 pm), gradient elution with re-hexane-2-propanol-H20, detection fluorescence, excitation 230 nm...

The first reactions concerned (Simons and Archer, 27) alkylation of benzene with propylene to form isopropylbenzene, with isobutene to form f-butylbenzene and di-f-butylbenzene, and trimethylethylene to form amylbenzene. Later on (Simons and Archer, 28) studied these and other reactions in more detail and showed that high yields could be obtained and that the product was not contaminated with tars or other obnoxious impurities. It was shown that the products obtained with trimethylethylene were mono- and di-f-amylbenzene, that phenyl-pentane resulted from the use of pentene-2, and that cyclohexene produced cyclohexylbenzene. Cinnamic acid reacted with benzene (Simons and Archer, 29) to form /3-phenylpropionic acid and allyl benzene reacted with benzene to form 1,2-diphenylpropane. It is interesting to note that although allyl alcohol reacted with benzene to form 1,2-diphenylpropane, the intermediate in the reaction, allylbenzene, was isolated and identified. This shows that in this case the hydroxyl reacted at a more rapid rate than the double bond. Both di- and triisobutylene reacted with phenol (Simons and Archer, 30) at 0°, when using hydrogen fluoride containing only relatively small quantities of water, to form f-butyl-benzene, but diisobutylene with 70% hydrogen fluoride produced p-f-octylphenol. Cyclohexene reacted with toluene to form cyclohexyl-toluene and octene-1 rapidly reacted with toluene to form 2-octyltoluene (Simons and Basler, 31). 

Another use of 4-/ i octylphenol is in the production of uv stabilizers. 4-/ f-Octylphenol reacts with sulfur dichloride to yield the thio-bisphenol derivative, which then reacts with nickel acetate to form 2,2 -thiobis(4-/ octylphenolate)-A -butylamine nickel [14516-71-3]. This type of stabilizer is widely used in the production of outdoor carpeting based on polypropylene fibers. Nickel compounds give a green discoloration which limits their applications. A second class of uv stabilizers based on the benzotriazole stmcture. 2-(2 -hydroxy-5 -/ f2 octylphenyl)benzotriazole [3147-75-9] is produced from 4-/ y-octylphenol (55). 

In later work, Lattimer et al. identified eight oligomeric series in a commercial version of poly-TMDQ by using the LC/FD-MS combination. Components of f-octylphenol/formaldehyde resins were also characterized using this method. In a series of studies, ozonation products of several p-phenylenediamine compoimds (rubber antiozonants) were separated by LC and identified by using FD-MS. In another study, model "efficient vulcanization" products were separated by colunm chromatography and characterized by FD-MS. "... 

Thiobis(4-f-octylphenolate)-W-butyl-amine nickel (Cyasorb UV 1084) n. An ultraviolet absorber used in polyolefins... 

Diisobutylene reacts with phenol to produce para-f-octylphenol, used to synthesize phenolic rubber tackifying resins. 

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