4-nonylphenol structure

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

Fig. 2.11.15. General structural formulae of (I) di-nonylphenolethoxy carboxylates (di-NPEC CnIIl9)2-C6H3-0-(CIl2-CH2-())I-CIl2-C02), (II) nonylphenoldiethoxysulfo-nates (NP(EO)2-S03 C9H19-C6H4-0-(CH2-CH2-0)2-CH2-S03), (III) nonylphenol-ethoxy sulfates (NPEO-SO4 C -Ce -O-fCHa-CHa-O -SOgH), and (IV) nonylphenolethoxy phosphate (NPEO-PO4 O9II19—CBII/ —G—(CH2-CH2-0)x-...

The commercially available nonylphenol diethoxysulfonate NP(EO)2-S03 (Triton X-200, formula C9H19-C6H4-0-(CH2-CH2-0)2-CH2-SO3, and shown with its structural formula in Fig. 2.11.15(11) (m = 2) was studied using API-FIA-MS. Negative APCI-mode spectra contained the signal of one compound that could be ionised in the form of a [M - H] ion at mlz 401. Positive ionisation of NP(EO)2-S03 resulted in a [M + NH4]+ ion at mlz 420 besides impurities with ions at mlz 356... 

In view of the inherent resistance of some surfactant metabolite isomers to complete mineralisation, efforts have to be mounted in order to obtain further insight into the reasons behind the persistence of these, such as the SPC and nonylphenol ethoxy carboxylates (NPECs). In order to achieve this, it would thus be indispensable to be able to fully elucidate the chemical structure of individual components, e.g. after isolation from environmental samples. Through the application of, for example, LC-ESI-MS-MS in combination with NMR analyses, this is now possible. 

In contrast, raspberry and core shell structures are formed when in both stages a non ionic surfactant, i.e., nonylphenol ethoxylated poly(ethylene glycol) and sodium persulfate are used. 

Fig. 8.5 Chemical structures of EDCs (a) bisphenol-A (b) triclosan (c) nonylphenol (d) 17b-estradiol (e) genistein (f) b-sitosterol...

Pumiliotoxin B has both cardiotonic and myotonic activity in isolated atrial or rat phrenic nerve diaphragm preparations (97). The cardiotonic activity is markedly dependent on the structure of the pumiliotoxin (95). Subsequent studies on the activity of pumiliotoxin B in neuromuscular preparations were interpreted as due to an apparent facilitation of calcium translocation from internal storage sites (99 see review in Ref. 5). Inhibitory effects on the calcium-dependent ATPase of sarcoplasmic reticulum were shown to be due not to pumiliotoxin B, but to phenolic impurities, namely, fcis(2-hydroxy-3-terf-butyl-5-methylphenyl)methane, 3,5-di-/ert-butyl-4-hydroxytoluene (BHT), and nonylphenols (100). 

This formulation is laid down by electrophoresis over the material to be coated, acting as the cathode, and finally heat cured. The process requires molecules with chemical structure suitably designed for different applications, and the chemistry of Mannich bases may represent a convenient tool for preparing variously substituted derivatives. In fact, as depicted in Fig. 187, the reactive functions leading to the final crosslinked material may be bound to several different positions of the oligomeric epoxy resin. The Mannich derivatives of bisphenol A (572)2 " - > -2 and nonylphenol (573)202.2a i.2()6 con-... 

Nonylphenol (Figure 5.28), a surfactant intermediate, has an -OH substituted ring structure similar to estradiol but with a long carbon chain attached. Nonylphenol does have estrogenic activity but only 9.0 X 10 6 that of estradiol (Pait and Nelson 2002). 

Recently, the hazardous effects of endocrine disruptors (environmental hormones) such as bisphenol A and nonylphenol on the human body have been reported, and led to the initiation of many studies concerning the detection and structural determination of these compounds present in tiny amounts [57]. As one of the QSAR analyses of environmental hormones, the relationship between their biological activity and chemical hardness has been reported [16]. By applying these analytical methods, the molecular toxicity and estrogen-like activity of environmental hormones have been found... 

The presence of liquid crystal structures at both the w-o and o-w interfaces in multiple emulsions has been investigated by Kavaliunas and Frank (31). Microscopic examination of w/o/w emulsions between crossed polarizers revealed the presence of liquid crystal phases at both inner (w-o) and outer (o-w) interfaces in a w/o/w system composed of water, p-xylene and nonylphenol diethylene glycol ether. Liquid crystalline phases were also detected in o/w/o emulsions at both interfaces. The presence of these liquid crystal structures was found to improve the stability of the emulsions markedly. Matsumoto (32, 33) have concluded that the oil layers in w/o/w systems are likely to be composed of or contain,at least in proximity to the aqueous phase,multilamellar layers of the lipophilic surfactant used in the formulation this is postulated in part to explain the rate of volume flux of water through the oily layer. 

Fig. 1. Structures of the alkylphenols and related compounds discussed in this review. Technical nonylphenol consists of up to 22 isomers, most of them having a branched alkyl side-chain in the para position.

The xs are the molar fraction of the two base surfactants in the mixture, but if they are relatively close products, e.g. nonylphenols with EON = 4 and 6, the weight fraction, which is easier to calculate, maybe used instead with insignificant error. In practice, it is preferable to use a relatively high total surfactant concentration to avoid fractionation effects, say, 2-3 wt.% at least. Note that EONbm only depends on all the other formulation variables, e.g. salinity, oil, alcohol and temperature, which are fixed in all experiments. Since neither the structure nor the a value is known, the correlation to be used for the unknown non-ionic surfactant is the one including characteristic parameter (3. 

Fig. 5 Molecular structures of selected xenoestrogens 1 - Ethynylestradiol, 2 - Bisphenol A, 3 - Phthalates, 4 - Nonylphenols...

Some of the important structures arising, a brief note of their properties and some of their many uses are listed in Table 11.1 The C4 and Cg alkylphenols are pure compounds although the latter due to rearrangement can contain a small proportion of the 1,1,2,3-tetramethylbutyl isomer. By contrast the Cg member is a mixture of several isomers as is the C 2> dodecylphenol a less well known material which is not listed in the Table. Nevertheless the vast number of uses of nonylphenol are partly attributable to this very lack of homogeneity. An extensive list of alkylphenols with their properties has been descrbed (ref.1)... 

In recent years considerable attention has been given to the biodegradability of polyethoxylates and the role of their structure in this process. In consequence, there has been a move away from multi-branched alkyl side-chain in the starting alkylphenolic raw material towards more linear chains, a circumstance already adopted in the use of kerylbenzenes for the manufacture of alkylaryl sulphonates. Another practice adopted has been that of sulphation of the terminal hydroxyl group in the polyalkoxylate. Recent studies on a comparison of ethoxylates derived from the natural alkenylphenol, cardanol and from nonylphenol have indicated a considerable difference in biodegradability (ref. 24). 

Prior reaction of nonylphenol with a variety of different aliyiic, allylglycidyl and glycidylacrylate intermediates and glycidol itself has been used to provide structures, containing unsaturation in a side-chain, which were then ethoxylated. Vinylic polymerisation proceeding through the double bond in the side-chain could finally be employed to obtain further structurally modified products. The final products from these transformations almost certainly are mixtures. 

The tungsten salt resulting from treatment of nonylphenol with tungstic hexachloride has found an application as a catayst for the metathetical copolymerisation of dicyclopentadiene and 5,5,6-trlchloronorbornene (ref. 43). Antimony and lead salts of alkyidithiophosphates are important additives for lubricating greases. In the nonylphenyl series such compounds are considered to have the dimeric structure shown (where M = Pb and Sb) (ref. 44). 

Whereas the 1,1,3,3-tetramethylbutyl side chain structure in t-octylphenol derived from diisobutene is usually the sole contributor, that in t-nonylphenol comprises a complex but nevetheless extremely useful mixture. Recent work on the separation of the isomers present on a cross-linked methylsilcone column by capillary GLC (ref. 47) could be useful in indicating the connection between structure and the properties in this valuable technical product. 

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