Phenolic hydrogens

Caprolactam [105-60-2] (2-oxohexamethyleiiiiriiQe, liexaliydro-2J -a2epin-2-one) is one of the most widely used chemical intermediates. However, almost all of the aimual production of 3.0 x 10 t is consumed as the monomer for nylon-6 fibers and plastics (see Fibers survey Polyamides, plastics). Cyclohexanone, which is the most common organic precursor of caprolactam, is made from benzene by either phenol hydrogenation or cyclohexane oxidation (see Cyclohexanoland cyclohexanone). Reaction with ammonia-derived hydroxjlamine forms cyclohexanone oxime, which undergoes molecular rearrangement to the seven-membered ring S-caprolactam. 

By-product processing CO, H2S, methane, ammonia, H2, phenols, hydrogen cyanide, N2, benzene, xylene, etc. Electrostatic precipitator, scrubber, flaring... 

The assumed transition state of this reaction is shown in Scheme 5.3. Yb(OTf)3, (J )-(-h)-BINOL, and DBU form a complex with two hydrogen bonds, and the axial chirality of (J )-(-h)-BINOL is transferred via the hydrogen bonds to the amine parts. The additive would interact with the phenolic hydrogen of the imine, which is fixed by bidentate coordination to Yb(III). Because the top face of the imine is shielded by the amine, the dienophiles approach from the bottom face to achieve high levels of selectivity. 

Solochrome dark blue or calcon ( C.1.15705). This is sometimes referred to as eriochrome blue black RC it is in fact sodium l-(2-hydroxy-l-naphthylazo)-2-naphthol-4-sulphonate. The dyestuff has two ionisable phenolic hydrogen atoms the protons ionise stepwise with pK values of 7.4 and 13.5 respectively. An important application of the indicator is in the complexometric titration of calcium in the presence of magnesium this must be carried out at a pH of about 12.3 (obtained, for example, with a diethylamine buffer 5 mL for every 100 mL of solution) in order to avoid the interference of magnesium. Under these conditions magnesium is precipitated quantitatively as the hydroxide. The colour change is from pink to pure blue. 

Studies with simple radicals show that carbon-centered radicals react with phenols by abstracting a phenolic hydrogen (Scheme 5.14). The phenoxy radicals may then scavenge a further radical by C -C or C-O coupling or (in the case of hydroquinones) by loss of a hydrogen atom to give a quinone. The quinone may then react further (Section 5.4.4). Thus two or more propagating chains may be terminated for every mole of phenol.I9j... 

This study shows that the optimization of process conditions could be achieved rapidly by a judicious use of statistics and parallel reactors. A two-level factorial method with two center points was used to limit the total number of experiments to ten. Using two identical high-pressure reactors in parallel further shortened the time required to conduct these experiments. For the model reaction of phenol hydrogenation over a commercially available Pd/C, it was experimentally determined that the optimal yield was 73% at 135 °C, 22.5 bar, and 615 ppm w/w NaOH... 

Keywords Phenol, Hydrogen peroxide, Ceramization, WHPCO, OOMW, Zeolite. 

The thermolysis of 2-methoxyphenol in the presence of cumene as a radical scavenger occurs via two possible pathways. A homolytic cleavage of the methoxyl 0-C bond leads to methane and 1,2-dihydroxybenzene whereas an induced route starting with abstraction of the phenolic hydrogen by cumyl radicals leads, after a cascade of reactions, to phenol, 2-hydroxybenzaldehyde, and 2-hydroxybenzyl alcohol. ... 

When an aqueous solution containing chlorobenzene (190 pM) and a nonionic surfactant micelle (Brij 58, a polyoxyethylene cetyl ether) was illuminated by a photoreactor equipped with 253.7-nm monochromatic UV lamps, phenol, hydrogen, and chloride ions formed as major products. It was reported that aromatic aldehydes, organic acids, and carbon dioxide would form from the photoreaction of chlorobenzene in water under similar conditions. A duplicate experiment was conducted using an ionic micelle (triethylamine, 5 mM), which serves as a hydrogen source. Products identified were phenol and benzene (Chu and Jafvert, 1994). 

The oxonium salt (122) reacts with phenylhydrazine to give the 1-phenyltriazole (123), the x-ray structure of which shows intramolecular hydrogen bonding between the phenol hydrogen and N(4) (Equation (47)) <89CHE94>. 

Aqueous solutions of NaOH or KOH are very effective at removing a variety of compounds from fuel. Components removed by extracting or washing the fuel with either of these caustic solutions include mercaptans, phenols, hydrogen sulfide, and naphthenic acids. Removal of these compounds can improve the color, odor,... 

Figure 8.4 Influence of the position of a nitro substituent on the pKa of a phenolic hydrogen.

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