Aromatic compounds, removal

Byker HJ. Halogenated aromatic compound removal and destruction process. United States Patent 4,659,443, 1987. 

The potential use of enzymes for trace aromatic compound removal has been shown on the laboratory scale. This type of examination can screen compounds for which the enzyme may be useful. 2-CP, a compound of organoleptic concern, has... 

In addition to sensory evaluation, free fatty acid analysis (the content is usually below 0.05%) and analysis of possible contaminants are carried out. The data given in Table 14.15 illustrate the amounts of pesticides and polycyclic aromatic compounds removed hy deodorization. However, this refining step also removes the highly desirable aroma substances which are characteristic of some cold-pressed oils such as olive oil. 

In practice superheated steam is generally employed for substances with a low vapour pressure (< 5-1 mm.) at 100°. Thus in the recovery of the products of nitration or aromatic compounds, the ortho derivative e.g., o-nitrophenol) can be removed by ordinary steam distillation the... 

For electrophilic substitutions in general, and leaving aside theories which have only historical interest, two general processes have to be considered. In the first, the 5 3 process, a transition state is involved which is formed from the aromatic compound, the electrophile (E+), and the base (B) needed to remove the proton ... 

The chemical oil contains ca 50 wt % naphthalene, 6 wt % tar acids, 3 wt % tar bases, and numerous other aromatic compounds. The chemical oil is processed to remove the tar acids by contacting with dilute sodium hydroxide and, in a few cases, is next treated to remove tar bases by washing with sulfuric acid. 

Acidic Hydrolysis. Hydrolysis of esters by use of water and a mineral acid leads to an equiUbrium mixture of ester, alcohol, and free carboxyHc acid. Complete reaction can only be achieved by removal of alcohol or acid from the equiUbrium. Because esters have poor solubiUty in water, the reaction rate in dilute acids is fairly low. Therefore, emulsifiers such as sulfonated oleic acid or sulfonated aromatic compounds (TwitcheU reagent) are added to facihtate the reaction. 

Solvent extraction removes harmful constituents such as heavy aromatic compounds from lubricating oils to improve the viscosity-temperature relationship. The usual solvents for extracting lubricating oil are phenol and furfural. 

Molecular sieves are available with a variety of pore sizes. A molecular sieve should be selected with a pore size that will admit H2S and water while preventing heavy hydrocarbons and aromatic compound.s from entering the pores. However, carbon dioxide molecules are about the same size as H2S molecules and present problems. Even thougli die COi is non-polar and will not bond to the active sites, the CO2 will entci the pores. Small quantities of CO2 will become trapped in the pores In this way small portions of CO2 are removed. More importantly, CO ih obstruct the access of H2S and water to active sites and decrease the eflectiveness ot the pores. Beds must be sized to remove all water and to pi ovitte for interference from other molecules in order to remove all H i.S. 

This last result bears also on the mode of conversion of the adduct to the final substitution product. As written in Eq. (10), a hydrogen atom is eliminated from the adduct, but it is more likely that it is abstracted from the adduct by a second radical. In dilute solutions of the radical-producing species, this second radical may be the adduct itself, as in Eq. (12) but when more concentrated solutions of dibenzoyl peroxide are employed, the hydrogen atom is removed by a benzoyloxy radical, for in the arylation of deuterated aromatic compounds the deuterium lost from the aromatic nucleus appears as deuterated benzoic acid, Eq. (13).The over-all reaction for the phenylation of benzene by dibenzoyl peroxide may therefore be written as in Eq, (14). 

It is of interest that both the methyl affinities and the reactivities of aromatic compounds toward the pheny radical are correlated both by Froax and by atom localization energies. Dewar has shown that the energy required to remove one atom from conjugation (in a hydrocarbon containing an even number of carbon atoms) is greater... 

The second step is nearly always faster than the first, so the first is rate determining and the reaction is second order (unless the formation of the attacking species is slower still, in which case the aromatic compound does not take part in the rate expression at all). If Y" " is lost, there is no net reaction, but if is lost, an aromatic substitution has taken place. If X" " is a proton, a base is necessary to help remove it. 

The study of the catalytic wet peroxide oxidation of p-coumaric acid over (Al-Fe)PILC has shown a complete removal of aromatic compounds and high TOC reduction (ca.50%) in 4 hours of reaction, leading at the end to total mineralization products (C02 and H20) and traces of oxalic acid. 

There are several chemical compounds found in the waste waters of a wide variety of industries that must be removed because of the danger they represent to human health. Among the major classes of contaminants, several aromatic molecules, including phenols and aromatic amines, have been reported. Enzymatic treatment has been proposed by many researchers as an alternative to conventional methods. In this respect, PX has the ability to coprecipitate certain difficult-to-remove contaminants by inducing the formation of mixed polymers that behave similarly to the polymeric products of easily removable contaminants. Thus, several types of PX, including HRP C, LiP, and a number of other PXs from different sources, have been used for treatment of aqueous aromatic contaminants and decolorization of dyes. Thus, LiP was shown to mineralize a variety of recalcitrant aromatic compounds and to oxidize a number of polycyclic aromatic and phenolic compounds. Furthermore, MnP and a microbial PX from Coprinus macrorhizus have also been observed to catalyze the oxidation of several monoaromatic phenols and aromatic dyes (Hamid and Khalil-ur-Rehman 2009). 

Trimethylgermyl substituents in aromatic compounds are easily removed with halogen, yielding the corresponding aryl halide, as shown in reaction 8119. Another example of phenyl group displacement was carried out with bromine as in reaction 2 (see end of Table 2)64. 

Sandmeyer s synthesis of aromatic nitriles is far more elegant than the removal of water from the ammonium salts of carboxylic acids, which latter reaction is also applicable to benzene derivatives. In particular, the former synthesis permits of the preparation of carboxylic acids via the nitriles, and so provides a complete substitute for Kolbe s synthesis (alkyl halide and potassium cyanide), which is inapplicable to aromatic compounds. The simplest example is the conversion of aniline into benzoic add. The converse transformation is Hofmann s degradation (benzamide aniline, see p. 152). 

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