Phenols 4-nonylphenol

Substituted phenols nonylphenol, pentachlorophenol (PCP), phenol, p-nitrophenol... 

Manuf./Distrib. Acres Org. Alfa Aesar Chemos GmbH SI Group p-Nonylphenol, branched. See p-Nonyl phenol Nonylphenol Nonylphenol 4 EO... 

NPE degradation products lower ethoxylates, phenol, 4-n-propyl-phenol, nonylphenol, CO2... 

Nonene, or propylene tetramer, is used to alkylate phenol, which is subsequently ethoxylated to produce nonylphenol ethoxylate, an efficient, rehable industrial surfactant. 

Alkylphenols undergo a carboxylation reaction known as the Kolbe Schmidt reaction. In the following example, the phenolate anion of /)-nonylphenol (15) reacts with carbon dioxide under pressure. Neutralization generates a sahcyhc acid (16) (10). 

Linear novolac resins prepared by reacting para-alkylphenols with paraformaldehyde are of interest for adhesive tackifiers. As expected for step-growth polymerization, the molecular weights and viscosities of such oligomers prepared in one exemplary study increased as the ratio of formaldehyde to para-nonylphenol was increased from 0.32 to 1.00.21 As is usually the case, however, these reactions were not carried out to full conversion, and the measured Mn of an oligomer prepared with an equimolar phenol-to-formaldehyde ratio was 1400 g/mol. Plots of apparent shear viscosity versus shear rate of these p-nonylphenol novolac resins showed non-Newtonian rheological behavior. 

Ethoxylated methylcarboxylates Propoxyethoxy glyceryl sulfonate Alkylpropoxyethoxy sulfate as surfactant, xanthan, and a copolymer of acrylamide and sodium 2-acrylamido-2-methylpropane sulfonate Carboxymethylated ethoxylated surfactants (CME) Polyethylene oxide (PEG) as a sacrificial adsorbate Polyethylene glycols, propoxylated/ethoxylated alkyl sulfates Mixtures of sulfonates and nonionic alcohols Combination of lignosulfonates and fatty amines Alkyl xylene sulfonates, polyethoxylated alkyl phenols, octaethylene glycol mono n-decyl ether, and tetradecyl trimethyl ammonium chloride Anionic sodium dodecyl sulfate (SDS), cationic tetradecyl trimethyl ammonium chloride (TTAC), nonionic pentadecylethoxylated nonylphenol (NP-15), and nonionic octaethylene glycol N-dodecyl ether Dimethylalkylamine oxides as cosurfactants and viscosifiers (N-Dodecyl)trimethylammonium bromide Petrochemical sulfonate and propane sulfonate of an ethoxylated alcohol or phenol Petrochemical sulfonate and a-olefin sulfonate... 

As to the main limitation of MS vs. FTIR detection, namely the inability to distinguish closely related isomers, this rarely plays a role in additive analysis. Notable examples of isomeric additives are the bifunctional stabilisers C22H30O2S as 4,4 -thio-bis-(6-t-butyl-m-cresol), 2,2 -thio-bis-(4-methyl-6-f-butylphenol) and 4,4 -thio-bis-(2-methyl-6-f-butylphenol) (Section 6.3.6), the bisphenolic antioxidants C23H32O2 (Plastanox 2246 and Ethanox 720) and the phenolic antioxidants C15H24O (nonylphenol and di-f-butyl-p-cresol). 

Schnaak et al. [4] Polychlorinated terphenyls, naphthalenes, chloropesticides, halogenated hydrocarbon solvents, aromatic hydrocarbon solvents (BTEX), chlorobenzenes, poly aromatic hydrocarbons (EPA 610), phenols, chlorophenols, phthalates, petroleum hydrocarbons, LAS and nonylphenol (NP), organotin compounds and 2,4-dichloroaniline 1 pg/kg to 10 mg/kg for chlorine-contained compounds 10 pg/kg to 1 g/kg for solvent and phenols 1 mg/kg to 10 g/kg for EPA610, DEHP, LAS, and mineral oils Sewage sludge... 

Fig. 10 Composition and spatial distribution of the main patterns of contamination identified in sediment of the Ebro River basin from year 2004 to 2006. Different temporal distribution of the PAHs pattern of contamination over the territory and constant distribution in time of the APs and heavier PAHs as well as the OCs pattern. Big circles representing higher levels of pattern contribution than small circles. Variables identification 1, naphthalene 2, acenaphtylene 3, acenapthene 4, fluorene 5, phenanthrene 6, anthracene 7, fluoranthene 8, pyrene 9, benzo(a) anthracene 10, chrysene 11, benzo(b)fluoranthene 12, benzo(k)fluoranthene 13, benzo(a)pyr-ene 14, indeno(l,2,3-cd)pyrene 15, dibenzo(a,h)anthracene 16, benzo(g,h,i)perylene 17, octyl-phenol 18, nonylphenol 19, tributylphosphate 20, a-HCH 21, HCB 22,2,4-DDE 23,4,4-DDE 24, 2,4-DDD 25, 4,4-DDD 26, 2,4-DDT 27, 4,4-DDT...

Nonwoven manufacturing, cotton, 3 18 Nonwoven materials, 24 620. See also Nonwoven fabrics Nonwoven processes, 17 496-497 Nonwovens. See also Nonwoven fabrics air-laid, 17 503 defined, 17 495-496 foam-bonded, 17 510 needled, 17 506, 507 thermal-bonded, 17 511-512 Nonwoven textile materials, 11 178-180 4-Nonylphenol (PNP), 2 225-226 health and safety data, 2 220t physical properties of, 2 205t Nonyl phenol, 10 429 8-Nonynoic acid, 5 34t... 

The synthesis of commercial nonylphenols generally proceeds through an alkylation reaction of phenols with propylene trimer [124], which itself has a spread of isomers [47]. The alkylation occurs preferentially at the para position of the phenol, but 3-6% of ortho-nonylphenol can be found in commercial products [125]. Also meta and disubstituted species have been mentioned [47]. A common feature of the isomers appears to be a dimethyl substitution of the a-carbon atom [83]. 

Fig. 2.1.7. Possible structures for the nonylphenol isomers 2(p-phenol)-methyloctane. indicates asymmetric carbon atom.

This includes bioremediation cases of contaminated sites with several toxic and carcinogenic pollutants, such as petroleum hydrocarbons, PAHs, dichlorobenzene, chlorinated hydrocarbons, carbon tetrachloride, Dicamba, methyl bromide, trinitrotoluene, silicon-based organic compounds, dioxins, alkyl-phenol polyethoxylates, nonylphenol ethoxylates, and polychlorinated biphenyls. The following is a brief summary of each case. 

Xie, Z Le Calve, S Feigenbrugel, V., Preup, T.G., Vinken, R., Ebinghaus, R., and Ruck, W. Henry s law constants measurements of nonylphenol isomer 4(3, 5-dimethyl-3-heptyl)phenol, fertia/y-octylphenol and y-hexachlorocyclohexane between 278 and 298 K, Atmos. Environ., 38(29) 4859-4868, 2004. 

Alkylphenol Ethoxylates (APE). The hydrophobes of most commercial APE are made by reacting phenol with either propylene trimer or diisobutylene to form nonylphenol or octylphenol. These products contain an aromatic moiety and extensive branching in their alkyl chains. It has been shown that APE biodegrade more slowly and less extensively than LPAE (3.15-20). The difference is more pronounced when the treatment system is operating under stress conditions such as low temperatures and high surfactant loadings. 

Source identification for several of the phenols, notable p-(l,l,3,3-tetramethylbu-tyl) phenol, and the nonylphenol isomers is more difficult. Concentration data shows highest levels around Philadelphia, implicating general urban activity as the primary source however, there are several high production chemical companies in the area, one of which produces these phenols commercially (10). Under these circumstances no definite source can be Identified. 

Phenol ethoxylates differ from the previous four categories in that they are non-ionic materials. Although not widely used, they are very effective at low addition levels and solutions of 2-4% by weight in water perform satisfactorily at low dosage level. The most common material is nonylphenol ethoxylate, and limited studies [12] have indicated that the higher value of n in Fig. 3.4 is the most effective. 

In general, there is no correspondence between the value of K obtained from the fit of kinetic data through Eqs. (la)—(If) and dark adsorption measurements. The degradation rate of phenol (ph, poorly adsorbed) and nonylphenol (nph, strongly adsorbed) differs only by a factor of 3 [23], Because it was demonstrated that the aromatic moiety is more susceptible of attack than the aliphatic chain, A lh would be almost identical in the two cases. Owing to the large ratio of A npij/T ph (>>3), it follows that the LH equation is inadequate. 

La Guardia MJ, Hale RC, Harvey E, et al. 2000. Endocrine disruptors (octylphenol, nonylphenol, nonyl phenol ethoxylates and polybrominated diphenyl ethers) in land applied sewage sludge biosolids. In Preprints of extended abstracts. American Chemical Society, Division of Envrionmental Chemistry. 

Phenols. Phenolic compounds are used in very large quantities for a variety of industrial purposes. They may also be formed in the environment by abiotic (e.g., hydroxylation in the atmosphere see Chapter 16) or biological processes (Chapter 17). A prominent example for the latter case is the formation of 4-nonylphenol from the microbial... 

Antioxidants. Phenolic antioxidants, added at about 0.1—0.5 phr, are usually chosen from among butylated hydroxytoluene [128-37-0] (BHT), and -nonylphenol [104-40-5] for liquid stabilizer formulations and bisphenol A [80-05-7] (2,2-bis-(p-hydroxyphenyl)propane) for the solid systems. Low melting thioesters, dilauryl thiodipropionate [123-28A] (DLTDP) or distearyl thiodipropionate [693-36-7] (DSTDP) are commonly added along with the phenolics to enhance their antioxidant performance. Usually a 3 1 ratio of thiodipropionate to phenolic antioxidant provides the desired protection. Most mixed metal stabilizer products contain the antioxidant ingredient. 

Other detergent alkylates which are gaining acceptance are benzene alkylated by pentamer and phenol alkylated by polypropylene, of which trimer is the preferred polymer. The pentadecylbenzene alkylate is sulfo-nated, while the nonylphenol alkylate is further reacted with ethylene oxide, the latter product going into the production of liquid non-ionic detergents. 

Phenolic compounds are used in commercial or consumer products or building materials (Rudel et al., 2001), especially ethoxylated alkylphenols of octylphenol and nonylphenol, which are widely used in surfactants (Ying, Williams and Kookana, 2002). They are known as endocrine disrupting compounds (EDC) as they bear hormonally active properties. Other EDCs found indoors include phthal-ates (Section 11.2.7), certain pesticides, organotin compounds (Section 11.2.5) and polybrominated diphenyl ethers (Section 11.2.8) (Rudel et al., 2001, 2003). 

Rudel et al. (2001) reported concentrations of nonylphenol and its mono- and di-ethoxylates up to 14 mg kg 1 in house dust for a 7-sample pilot study in the USA. Concentrations of ethoxylated octylphenols did not exceed 5 mg kg"1. Of the more than 30 phenols analyzed only 4-nonylphenol was found in air with concentrations up to 0.118pgm"3. Wilson, Chuang and Lyu (2001) reported the nonylphenol content of dust samples from 10 child care centers (USA) to be 4.16-13. Smgkg 1 the Bisphenol A content to be 1.04—4.51 mgkg 1, respectively. In their study concentrations in air amounted to 0.052-0.527 ggm 3 for nonylphenol and up to 0.0018ggm 3 for Bisphenol A. 

Results for endocrine disrupting phenols in house dust as reported by Rudel et al. (2003) and Butte et al. (2001) are compiled in Table 11.1. Rudel et al. (2003) sampled indoor air in 120 homes as well. They analyzed both house dust and air for 89 organic chemicals identified as EDCs. The most abundant compounds in air included 4-nonylphenol and 4-t-butylphenol with typical concentrations in the range of 0.050-1.500ggm 3. Saito, Onuki and Seto (2004) collected air samples from houses, offices, and outdoor points. 4-t-butylphenol, 4-t-octylphenol and 4-nonylphenol were detected in both indoor and outdoor air. Concentrations and detection frequencies were higher in indoor air than outdoor air. The maximum levels of 4-t-butylphenol, 4-t-octylphenol and 4-nonylphenol in indoor air were 0.387, 0.0457 and 0.680 ggm 3, respectively. 4-t-butylphenol and 4-nonylphenol were detected with high frequencies (more than 97%) in the indoor air samples. Wilson, Chuang and Lyu (2001) reported a mean of 0.0007 gg m"3 Bisphenol A in the air of 10 child care centers and a mean of 0.203 gg m 3 for the sum of nonylphenol and its ethoxylates. 

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