Aromatic acids from hydrocarbons

Schorigin P. A new synthesis of aromatic carboxylic acid from hydrocarbons. II. Annoimcement. Ber Dtsch Chem Ges. 1910 43 1938-1942. 

Fig. 20. Proposed photochemical mechanisms for the generation of acid from sulfonium salt photolysis. Shown ate examples illustrating photon absorption by the onium salt (direct irradiation) as well as electron transfer sensitization, initiated by irradiation of an aromatic hydrocarbon.

The fluids have reasonably good chemical resistance but are attacked by concentrated mineral acids and alkalis. They are soluble in aliphatic, aromatic and chlorinated hydrocarbons, which is to be expected from the low solubility parameter of 14.9 MPa. They are insoluble in solvents of higher solubility parameter such as acetone, ethylene glycol and water. They are themselves very poor solvents. Some physical properties of the dimethylsilicone fluids are summarised in Table 29.2. 

Uintaite is described in Kirk-Othmer [1329]. Typical uintaite used in drilling fluids is mined from an area around Bonanza, Utah and has a specific gravity of 1.05 with a softening point ranging from 190° C to 205° C, although a lower softening point (165° C) material is sometimes used. It has a low acid value, a zero iodine number, and is soluble or partially soluble in aromatic and aliphatic hydrocarbons, respectively. 

MERIFINING A process for extracting aromatic mercaptans and organic acids from cracked hydrocarbon fractions by aqueous alkali, using a bundle of hollow fibers. Developed by the Merichem Company, Houston, TX. Twelve units were operating as of 1991. 

The prediction of retention times in a given eluent from log P has been proposed for aromatic hydrocarbons.19 The log A values of phenols21 and nitrogen-containing compounds22 were also related to their logP, and the calculated log P was used for the qualitative analysis of urinary aromatic acids, i.e. for the identification of metabolites in urine from the differences of log P in reversed-phase liquid chromatography.23,24... 

Possible slight effects from carboxylic acids, anhydrides, aromatic and aliphatic hydrocarbons, alcohols, aldehydes, ketones, esters, chlorinated solvents... 

Organic aerosols formed by gas-phase photochemical reactions of hydrocarbons, ozone, and nitrogen oxides have been identified recently in both urban and rural atmospheres. Aliphatic organic nitrates, such dicarboxylic acids as adipic and glutaric acids, carboxylic acids derived from aromatic hydrocarbons (benzoic and phenylacetic acids) and from terpenes emitted by vegetation, such as pinonic acid from a pinene, have been identified. The most important contribution in this held has been that of Schuetzle et al., who used computer-controlled... 

Reaction XCI. (b) Oxidation of Aromatic Hydrocarbons to Aldehydes by the action of Chromic Acid in Acetic Anhydride Solution. (A., 311, 353 D.R.P., 121788.)—In the ordinary way, chromic acid oxidises hydrocarbons to aldehydes and then to acids. But if acetic anhydride and cone, sulphuric acid is present, the di-acetyl derivative of the aldehyde is formed and this does not undergo further oxidation. The aldehyde is obtained from the di-ester by hydrolysis. (Cf. the preparation of salicylaldehyde, p. 105.)... 

The acid, base, and neutral Lewis base fractions consist of polar molecules capable of hydrogen bonding and, therefore, of intermolecular association. These polar fractions, which constitute nearly two-thirds of the 675°C+ residuum, have high concentrations of heteroelements in comparison to the nonpolar aromatic and saturate hydrocarbons, as shown in Table IX for the residuum from a Russian crude oil. Infrared spectroscopy of the acid fraction revealed mostly pyrroles with phenols but only traces of... 

From the selectivity point of view, LC-NMR coupling is especially suited to the analysis of compound classes such as nitroaromatics, phenols, aromatic amines, aromatic carboxylic acids, polyaromatic hydrocarbons (PAHs), polychlorinated biphenyls (PCBs), and azo- and anthraquinone dyes. Another advantage of LC-NMR coupling for the investigation of aromatic compounds in environmental samples is that the position of substituents on the aromatic ring, e.g. in unknown metabolites or degradation products, can best be determined by NMR spectroscopy. 

Sulfonation is the introduction of a sulfonic acid group (-S03H) into an organic compound as, for example, in the production of an aromatic sulfonic acid from the corresponding aromatic hydrocarbon. 

Functionalization of hydrocarbons from petroleum sources is mainly concerned with the introduction of oxygen into the hydrocarbon molecule. In general, two ways are open to achieve oxygen functionalization oxidation and carbonylation. Oxidation is commonly encountered in the synthesis of aromatic acids, acrolein, maleic anhydride, ethene oxide, propene oxide, and acetaldehyde. Hydroformylation (CO/H2) (older literature and the technical literature refer to the oxo reaction) is employed for the large-scale preparation of butanol, 2-ethylhexanol, and detergent alcohols. The main use of 2-ethylhexanol is in phthalate esters which are softeners in PVC. The catalysts applied are based on cobalt and rhodium. (For a general review see ref. 3.)... 

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