Hydrocarbons, hydrocarbon sulfonic acid esters

Hydrocarbons from sulfonic acid esters OSOgR -> H... 

Mechanisms of Carbon-Oxygen Alkylations. Kinetic studies have been made of reactions between chlorinated hydrocarbons and sodium or potassium alcoholates. The rate data indicate second-order equations between the reactants. Phenol and substituted phenols were alkylated using sulfonic acid esters. The rates of the reactions depend on the substituent on the aromatic ring. The relative velocities were as follows p-creso], 1.58 2-naphthol, 1.46 phenol, 1.0 salicyclic acid, about 0.3 p-chlorophenol, 0.16 and o-cresol, less than 0.12. Electronic considerations are probably the cause of the different reaction rates. 

To overcome these difficulties, drilling fluids are treated with a variety of mud lubricants available from various suppHers. They are mostly general-purpose, low toxicity, nonfluorescent types that are blends of several anionic or nonionic surfactants and products such as glycols and glycerols, fatty acid esters, synthetic hydrocarbons, and vegetable oil derivatives. Extreme pressure lubricants containing sulfurized or sulfonated derivatives of natural fatty acid products or petroleum-base hydrocarbons can be quite toxic to marine life and are rarely used for environmental reasons. Diesel and mineral oils were once used as lubricants at levels of 3 to 10 vol % but this practice has been curtailed significantly for environmental reasons. 

Reactions of the hydrocarbon chain in alkanoic acids include a-sulfonation and halogenation (51—54). The a-sulfonated fatty ester salts have excellent lime-dispersing properties and are valuable surface-active agents. 

Types of compounds are arranged according to the following system hydrocarbons and basic heterocycles hydroxy compounds and their ethers mercapto compounds, sulfides, disulfides, sulfoxides and sulfones, sulfenic, sulfinic and sulfonic acids and their derivatives amines, hydroxylamines, hydrazines, hydrazo and azo compounds carbonyl compounds and their functional derivatives carboxylic acids and their functional derivatives and organometallics. In each chapter, halogen, nitroso, nitro, diazo and azido compounds follow the parent compounds as their substitution derivatives. More detail is indicated in the table of contents. In polyfunctional derivatives reduction of a particular function is mentioned in the place of the highest functionality. Reduction of acrylic acid, for example, is described in the chapter on acids rather than functionalized ethylene, and reduction of ethyl acetoacetate is discussed in the chapter on esters rather than in the chapter on ketones. 

Olefins - [FEEDSTOCKS - COALCHEMICALS] (Vol 10) - [FEEDSTOCKS-PETROCHEMICALS] (VollO) - [HYDROCARBONS - SURVEY] (Vol 13) -m automobile exhaust [EXHAUSTCONTROL, AUTOMOTIVE] (Vol 9) -catalyst for stereospeafic polymerization [TITANIUMCOMPOUNDS - INORGANIC] (Vol 24) -esters from [ESTERIFICATION] (Vol 9) -hydroxylation using H202 [HYDROGEN PEROXIDE] (Vol 13) -luminometer ratings [AVIATION AND OTHER GAS TURBINE FUELS] (Vol 3) -osmium oxidations of [PLATINUM-GROUP METALS, COMPOUNDS] (Vol 19) -polymerization [SULFONIC ACIDS] (Vol 23) -reaction with EDA [DIAMINES AND HIGHER AMINES ALIPHATIC] (Vol 8) -silver complexes of [SILVER COMPOUNDS] (Vol 22)... 

Fat- and oil-soluble dyes are also soluble in waxes, resins, lacquers, hydrocarbons, halogenated hydrocarbons, ethers, and alcohols, but not in water. It is not possible to differentiate clearly between them and the alcohol- and ester-soluble dyes. With the exception of blue anthraquinone derivatives, fat- and oil-soluble dyes are azo dyes, generally based on simple components. According to their degree of solubility they usually contain hydroxyl and/or amino groups, but not sulfonic acid and carboxylic acid groups. Examples of fat- and oil-soluble azo dyes are C.I. 

Sulfonic acids and sulfonate salts contain the -S03H and -SO) groups, respectively, attached to a hydrocarbon moiety. The structural formulas of benzene sulfonic acids and of sodium 1 -(p-sulfophenyl)decane, a biodegradable detergent surfactant, are shown in Figure 1.19. The common sulfonic acids are water-soluble strong acids that lose virtually all ionizable H+ in aqueous solution. They are used commercially to hydrolyze fat and oil esters to produce fatty acids and glycerol used in chemical synthesis. 

Two earlier studies (Kenar et al., 2005 Knothe et al., 2000) were conducted on the effects of compounds synthesized with hydrocarbon tail-group structures resembling those of FAME with attached bulky moieties. These studies examined novel fatty diesters made from reaction of diols with acids and diacids with 2-octanol in toluene solvent with p-toluene sulfonic acid catalyst and branched-chain esters of carbonic acid (carbonates) synthesized in nonyl alcohol with n-dibutyltin oxide catalyst. None of the synthesized compounds demonstrated effectiveness in decreasing CP or PP of SME. 

Some work [5] has been performed on the photochemical reaction between sulfur dioxide and hydrocarbons, both paraffins and olefins. In all cases, mists were found, and these mists settled out in the reaction vessels as oils with the characteristics of sulfuric acids. Because of the small amounts of materials formed, great problems arise in elucidating particular steps. When NO and O2 are added to this system, the situation is most complex. Bufalini [3] sums up the status in this way The aerosol formed from mixtures of the lower hydrocarbons with NO , and SO2 is predominantly sulfuric acid, whereas the higher olefin hydrocarbons appear to produce carbonaceous aerosols also, possibly organic acids, sulfuric or sulfonic acids, nitrate-esters, etc. ... 

Nonaqueous organic solvents consist of the following classes of compounds aliphatic and aromatic hydrocarbons and their halogenated and nitro derivatives, alcohols, carboxylic acids, esters, ethers, ketones, aldehydes, amines, nitriles, unsubstituted and substituted amides, sulfoxides, and sulfones. In general, a compound... 

The addition takes place according to Markownikoff s rule. The addition of carbo lic acida to the double bonds of isobutylene and trimethyl-ethylene gives tertiary esters. A true equilibrium independent of sulfuric acid concentrations is established in the exothermic reaction. The addition does not go well with ethylene, but goes well with many of the higher alkenes, particularly with some of the terpenes. To avoid the polymerizing effects of sulfuric acid, various other catalysts, such as sulfonic acids, triethylamine, hydrofluoric acid, boron trifluoride, and cuprous chloride have been used. The addition may take place at room temperature or higher and is aided by pressure. The vapors of the acid and hydrocarbon may be passed over catalysts, such as activated carbon, heteropoly acids, or metal phosphates. ... 

At present, PTC is a common methodology for alkylation of a large variety of carbanions of nitriles, esters, ketones, sulfones, acidic hydrocarbons, aldehydes, etc. The upper limit of the pAla value for C—H acids able to form carbanions and undergo alkylation under PTC conditions is around 24. In the alkylation of carbanions with alkyl iodides often the inhibitory effect of iodide anions is observed, similarly as in the case of reactions of inorganic anions. For more detailed discussion see Section IV.C. 

Reaction of cyanuric chloride with amines to give reactive dyes 2. Sulfonation and nitration of naphthalene at low temperatures 3. Reaction between terephthalic acid and ethylene oxide in a solvent in the presence of dissolved catalysts 4. Manufacture of diisocyanate by reaction between phosgene and hydrochlorides of amines 5. Alkaline hydrolysis of solid esters such as di-/3-chloroelhyl oxalate and nitrobenzoic acid esters Venkatraman (1972) Groggins (1958) Hydrocarbon Proc. Petrol. Refiner (1971) Bhatia et al. (1976) Sharma and Sharma (1969, I970a,b)... 

Mixtures of hydrocarbons with calcium alkyl phosphate particles are known to be effective antifoams in the context of domestic textile machine washing where wash cycles can last for up to 1 h and involve temperature ranges from 30°C to 95°C (see Section 8.2.4.1) [43, 44]. Under these circumstances, little or no deactivation of antifoam effectiveness is apparent. Mixtures of hydrocarbons with alkyl phosphoric acid esters also function as antifoams in this context provided the aqueous phase has a high enough pH and calcium ions are present [43, 44] so that the calcium salts can precipitate as particles in situ at the relevant hydrocarbon-water interface. This behavior is of course analogous to that shown by mixtures of oleic acid and hexadecane when dispersed in an aqueous phase under similar conditions [45]. As with the preformed calcium alkyl phosphate particles, no deactivation of antifoam effectiveness is observed in the case of in situ formation of the precipitates. Indeed, it has been observed that continuous aeration for several hours, using a circulating Ross-Miles apparatus at 90°C (see Section 2.2.3), of an aqueous solution of a blend of a commercial sodium dodecylbenzene sulfonate and an ethoxylated alcohol in the presence of mixtures of a hydrocarbon and an alkyl phosphoric acid ester (dispersed... 

Trimellitates, paraffinic sulfonic acid and phenyl esters, poly(es-ter)s, chlorinated hydrocarbons, aliphatic or aromatic monocarbox-ylic acid esters such as benzoates, and a variety of elastomers are common plasticizers. 

Effluents from the manufacture of Pb(CH3)4 can be treated with an alkali metal borohydride, e.g., NaBH4 at pH 8 to 11 to substantially reduce the level of dissolved lead compounds, like [Pb(CH3)3][145, 146]. Zn can also be used [147]. Liquid NH3 and toluene are used to remove solid NH4Clfrom the apparatus for producing Pb(CH3)4 by the NH3- or amine-catalyzed reaction of CH3CI with a PbNa alloy [148]. Stabilization of Pb(CH3)4, and of antiknock fluids containing Pb(CH3)4, is accomplished by addition of compounds, like toluene [149], xylene [141, 150], styrenes [151], naphthalenes [149, 151, 152], anthracenes [152], substituted phenols [141, 152 to 155], olefinic hydrocarbons [152], alcohols [141, 152], amines [155], hydroquinones [156], ethers [141], saturated or unsaturated carboxylic acids [141, 152], esters of phosphoric acid [152], or of sulfuric acid [157], or of sulfonic acids [141], imidazoles [158], alkyl halides and alkyl thiocyanates [141], or tall oil [159] see also Organolead Compounds , Vol. 2, Section 1.1.1.2, to be published. 

Continuing with the example of dodecane—based surfactant materials, the parent hydrocarbon can be sulfated to yield dodecane sulfonic acid (path 5), which closely resembles the sulfuric acid ester discussed previously and has similar water solubility ... 

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