Showing papers on "Benzoic acid published in 1978"

Decarboxylation by SO˙4− Radicals

Abstract: Decarboxylation by the reaction of SO/sub 4//sup -/ radical with aliphatic and aromatic carboxylic acids has been examined. Most aliphatic acids undergo efficient decarboxylation by SO/sub 4//sup -/ whereas their reactions with hydroxyl radical result in little decarboxylation. Aromatic acids decarboxylate to varying degrees depending on the other substituents. For example, benzoic and the phthalic acids undergo efficient decarboxylation, while o-toluic, p-hydroxybenzoic, and p-methoxybenzoic acid show only a small degree of decarboxylation. The findings support the conclusion that SO/sub 4//sup -/ reacts by electron transfer oxidation while OH either adds or abstracts H. Decarboxylation by H/sub 2/PO/sub 4/ radicals was also examined in a few cases and found to be less efficient than that by SO/sub 4//sup -/.

Arene oxides in styrene metabolism, a new perspective in styrene toxicity?

Abstract: The metabolism of styrene was studied in the rat after intraperitoneal administration of the cold and the 14C-labeled compound. In addition to phenylethylene glycol, mandelic acid, benzoic acid and hippuric acid, phenolic metabolites, namely, 4-vinylphenol, p-hydroxymandelic acid, p-hydroxybenzoic acid, and p-hydroxyhippuric acid, were identified in the urine of the treated animals. These biotransformation products were characterized by mass spectrometry and by comparative thin layer chromatography with standard compounds. Results of covalent binding studies of 14C-phenylethylene glycol to rat liver microsomal proteins suggest that these phenolic compounds may be formed as a result of chemical rearrangements of unstable arene oxides, reactive intermediates possibly implicated in styrene toxicity.

The mechanism of reaction of sulfate radical anion with some derivatives of benzoic acid

Abstract: The products of the reactions of SO/sub 4//sup -/ with some benzoic acid derivatives have been examined by ESR using steady-state radiolysis and photolysis to produce SO/sub 4//sup -/ and by optical absorption spectrophotometry in pulse radiolysis experiments. The optical absorption spectrum of the hydroxycyclohexadienyl radical following reaction of benzene with SO/sub 4//sup -/ is shown to be formed with <0.1 ..mu..s delay. Thus it appears that a cation is formed which reacts very rapidly with water. Similarly, pulse ESR methods have been used to show that the p-carboxyphenyl radical is formed within <1 ..mu..s of the reaction of SO/sub 4//sup -/ with terephthalate. With benzoate, most of the reaction leads to the phenyl radical but about 30% gives hydroxycyclohexadienyl radicals. The three isomeric toluates give different products. The ortho isomer gives mainly the o-carboxybenzyl radical while the para isomer gives approximately equal amounts of p-carboxybenzyl, p-methylphenyl, and a mixture of hydroxycyclohexadienyl radicals. The meta isomer gives mainly a mixture of hydroxycyclohexadienyl radical isomers. Several carboxyphenols were studied by ESR and all gave phenoxyl radicals. All reactions observed are consistent with the oxidation of the benzene ring to a cationic species which then reacts in parallel reactions by either hydroxylation,more » loss of a proton (from OH or CH/sub 3/ groups), or loss of CO/sub 2/.« less

Metal corrosion inhibitor

Abstract: Metal corrosion inhibitor comprising (a) benzoic acid and/or a benzoate, (b) nitrous acid and/or a nitrite, (c) phosphoric acid and/or a phosphate, and (d) at least one selected from mercaptobenzothiazole, its salts, benzotriazole and tolyltriazole, which can exhibit excellent anti-corrosive property to various metals for a long term and can be diluted with an aqueous liquor and can be employed in combination with usual anti-freezing agents.

Absolute rate constants for reactions of phenyl radicals

Abstract: The absolute rate constant for the addition of p-carboxyphenyl radical to p-bromobenzoate anion in aqueous solution has been determined by optical pulse radiolysis and time-resolved ESR (electron spin resonance) experiments to be 7.6 x 10/sup 6/ M/sup -1/ s/sup -1/ (corrected to zero ionic strength). The rate constants for addition of phenyl radicals to typical aromatic systems should be of this same magnitude. Addition of p-carboxyphenyl radical to benzene occurs with a similar rate constant and results in the formation of a substituted cyclohexadienyl radical that can be quantitatively oxidized to biphenyl-4-carboxylic acid. Abstraction from hydrogen donors results in the quantitative formation of benzoic acid. By reference to the absolute rate for addition to p-bromobenzoate the rate constant for H abstraction from isopropyl alcohol has been determined from competitive measurements of benzoic acid formation to be 5.2 x 10/sup 6/ M/sup -1/ s/sup -1/. Measurements by optical pulse radiolysis and time-resolved ESR methods give comparable values. H atom abstraction from other alcohols is found to be only modestly slower. It is clear from these measurements that the lifetime of phenyl radicals in the presence of most organic materials will usually be very low so that reactions second order in phenylmore » radicals will not normally be important.« less

The anaerobic decomposition of benzoic acid during methane fermentation. IV. Dearomatization of the ring and volatile fatty acids formed on ring rupture.

Abstract: A possible pathway for the anaerobic utilization of benzoic acid by a methanogenic consortium is suggested. Cyclohexane carboxylic acid and 1-cyclohexene-1-carboxylic acid have been identified as intermediates before ring rupture. Suprisingly, 3-cyclohexene-1-carboxylic acid interferes with utilization of other cyclic acids. In addition, isobutyric acid or short chain acids containing carbon-carbon double bonds could not be used without induction periods of a week or longer. A number of volatile fatty acids (heptanoic, valeric, butyric, propanoic, and acetic) have been identified and are suggested intermediates.

Textile treatment compositions

Abstract: A textile treatment composition in emulsion form which is based on a mixture of cationic and nonionic softener includes an aromatic mono- or di-carboxylic acid as a viscosity modifier The presence of a carboxylic acid such as benzoic acid or salicylic acid in emulsified mixtures of a di-higher alkyl quaternary ammonium salt and a nonionic material having at least one higher alkyl chain gives a significant increase in viscosity

Radiation Chemistry of the Ferrous Sulfate-Benzoic Acid-Xylenol Orange System

Abstract: GUPTA, B. L., BHAT, R. M., GOMATHY, K. R., AND SUSHEELA, B. Radiation Chemistry of the Ferrous Sulfate-Benzoic Acid-Xylenol Orange System. Radiat. Res. 75, 269-277 (1978). In the dosimetric system containing 0.20 mM ferrous ammonium sulfate, 5.0 mM benzoic acid, and 0.20 mM xylenol orange in 0.05 N sulfuric acid (FBX system), benzoic acid increases the G(Fe3+) value and ferric ions form a complex with xylenol orange. This paper presents the investigations carried out regarding the reactions of H202, OH, and H in the FBX system. The OH radicals were generated by the reaction of ferrous ions with H202. In the FBX system, each H202, OH, and H leads to the oxidation of 8, 7, and 11 ferrous ions, respectively. In the absence of xylenol orange, the above values respectively are 12, 11, and 13. The rate constant of the reaction of OH radical with xylenol orange in 0.05 N H2SO4 has been measured by competition kinetics using benzoic acid and its value has been found to be 7.9 X 109 M-' sec-L. In the absence of oxygen there is no radiolytic oxidation of ferrous ions in FBX system.

Bifunctionalized resins. Applications to the synthesis of insect sex attractants

Abstract: A 2% crosslinked divinylbenzene–styrene copolymer, incorporating benzoyl chloride groups, was used to monoprotect the symmetrical diol 1,10-decanediol. The corresponding monotrityl ether and cis-10-tetradecen-1-ol were prepared by this system, the latter by a Wittig reaction of a polymer-bound ylide with an aldehyde in the solution phase. A series of bifunctionalized resins containing proximally located trityl alcohol and benzoic acid groups was prepared in an attempt to prepare diol linked to the polymer via both a trityl ether and a benzoate linkage. It was established that these polymers bound 1,10-decanediol exclusively at one end only. Polymers, containing both trityl alcohol and benzoic acid groups in a random array or polymers containing proximally located trityl alcohol groups, gave mixtures of both monoprotected and doubly protected diol.

Polyimide-esters and filaments prepared from 4-(4'-carboxyphthalimido)benzoic acid or 4-(4'-hydroxyphthalimido)phenol

Abstract: High modulus filaments are melt-spun from polyimide-esters derived from 2,6-naphthalene dicarboxylic acid and either a substituted diphenol and 4-(4'-carboxyphthalimido)benzoic acid or terephthalic acid and 4-(4'-hydroxyphthalimido)phenol. The polyimide esters are optically anisotropic in the melt. As-spun filaments from these polymers can be heat treated while free from tension to increase their tenacity.

Process for preparing epoxy resins from hydroxy benzoic acid and bisphenol

Abstract: A process for preparing an epoxy resin, which comprises reacting p-hydroxybenzoic acid and bisphenol A with an epihalohydrin in the presence of a base using a quaternary ammonium salt as a catalyst, the amount of the p-hydroxybenzoic acid being 10 to 90 mole% and the amount of the bisphenol A being 90 to 10 mole%, both based on the total amount of the hydroxybenzoic acid and bisphenol A.

Hydrogen migrations in mass spectrometry. VI—the chemical ionization mass spectra of substituted benzoic acids and benzyl alcohols†

Abstract: The H2 and CH4 chemical ionization mass spectra of a series of series of substituted benzoic acids and substituted benzyl alcohols have been determined. For the benzoic acids the major fragmentation reactions of the protonated molecule involve elimination of H2O or elimination of CO2, the latter reaction involving migration of the carboxylic hydrogen to the aromatic ring. For the benzyl alcohols the major fragmentation reactions of [MH]+ involve loss of H2O or CH2O, analogous to the CO2 elimination reaction for the benzoic acids. It is shown that the CO2 and CH2O elimination reactions occur only when a conjugated aromatic ring system is present, and that for the carboxylic acid systems, methyl groups and, to a lesser extent, phenyl groups are capable of migrating. The only discernible effect of substituents on the fragmentation of [MH]+ is an enhancement of the H2O loss reaction in the benzoic acid system when an amino, hydroxyl, or halogen substituent is ortho to the carboxyl function. This ‘ortho’ effect, which differs in scope from that observed in electron impact mass spectra, is attributed to an intramolecular catalysis by the ortho substituent of the 1,3 hydrogen migration in the carbonyl protonated acid followed by H2O elimination. Apparently, this route is favoured over the direct elimination of H2O from the carbonyl protonated acid, since the latter has a high activation energy barrier because of unfavourable orbital symmetry restrictions.

Taurine Conjugation in Metabolism of 3-Phenoxybenzoic Acid and the Pyrethroid Insecticide Cypermethrin in Mouse

Abstract: 1. A substantial proportion of the radioactivity of an oral dose (1-20 mg/kg) of 3-phenoxy[14C]benzoic acid and the pyrethroid insecticide trans- and cis-[aryl-14C]cypermethrin (an α-cyano-3-phenoxybenzyl ester) is eliminated rapidly in urine of mice.2. The major urinary metabolite of these compounds in two strains of mice is N-(3-phenoxybenzoyl)taurine.3. Neither 3-phenoxybenzoic acid nor cypermethrin gives a taurine conjugate in rats.4. Benzoic acid gives no taurine conjugate in mice.

Taurine Conjugates as Metabolites of Arylacetic Acids in the Ferret

Abstract: 1. The pattern of conjugation in the ferret of 8 arylacetic acids and, for comparison, benzoic acid and 4-nitrobenzoic acid was examined.2. The arylacetic acids, phenylacetic, 4-chloro- and 4-nitro-phenylacetic, α-methylphenylacetic (hydratropic), 1- and 2-naphthylacetic and indol-3-ylacetic acids, were excreted in the urine as taurine and glycine conjugates. Diphenylacetic acid did not form an amino acid conjugate and was excreted as a glucuronide.3. The taurine conjugate was the major metabolite of 4-nitrophenylacetic, α-methylphenylacetic, 1- and 2-naphthylacetic and indol-3-ylacetic acids, whereas the glycine conjugate was the major metabolite of phenylacetic and 4-chlorophenylacetic acids. Taurine conjugation did not occur with benzoic and 4-nitrobenzoic acids which were excreted as glycine and glucuronic acid conjugates.4. Phenacetylglutamine and 4-hydroxyphenylacetic acid were minor urinary metabolites of phenylacetic in the ferret.5. A number of taurine conjugates of aliphatic and aromatic acids w...

Solvent effect on the dimerization and hydration constant of benzoic acid

Abstract: The hydration and dimerization of benzoic acid have been studied at 25°C by partition and solubility measurement of water in organic phase containing benzoic acid. Organic solvents used include n-hexane, cyclohexane, toluene, benzene, chlorobenzene and 1,2-dichloroethane. The benzoic acid being denoted as HA, the following associated species have been found in the organic phase: HA · H2O, (HA)2, (HA)2· H2O and (HA)2·(H2O)2. The hydration constants of these hydrated species together with hydration-corrected dimerization and partition constants were evaluated. Possible structures of the hydrated species have been elucidated.

The anaerobic decomposition of benzoic acid during methane fermentation. III. The fate of carbon four and the identification of propanoic acid.

Abstract: Anaerobic rupture of the benzoic acid ring was investigated. Carbon 4 was converted primarily to carbon dioxide. Following ring rupture during methane fermentation, propanoic acid is an intermediate, and carbon 4 of benzoate becomes its carboxyl.

Solubilization of benzoic acid derivatives by polyoxyethylene lauryl ether.

Abstract: The solubilization of 34 benzoic acid derivatives by polyoxyethylene lauryl ether micelles was quantitatively studied by solubility measurement and equilibrium dialysis. The logarithms of partition coefficients (K) of solubilizates between aqueous and micellar phases were directly related to the logarithms of their partition coefficients between aqueous solution and n-octanol (Poetanol). The plots could be grouped in four parallel linear relationships, each of which was characterized by the intercept b value. When the b value is connected with the positional distribution of hydrophilicity of the palisade layer with reference to n-octanol water content, the physical meaning of the value is probably related to the site of incorporation of solutes within the polyoxyethylene mantle. The results show that benzoic acid derivatives examined are classified into dicarboxylic acids, nitro and cyano compounds, the majority of compounds, and salicylic acids group, which are located in order from the outer layer of the mantle toward the hydrocarbon core.

Interphenylene 11,12-secoprostaglandins

Abstract: Novel interphenylene derivatives of 11,12-secoprostaglandins are prepared by the stepwise alkylation of the ethyl ester or the t-butyl ester of acetoacetic acid. One such method involves treatment of the t-butyl ester of acetoacetic acid with a strong base to form the anion followed by treatment with ethyl p-(3-bromopropyl)benzoate to produce ethyl 4-(4-tert-butoxycarbonyl-5-oxo-hexyl)benzoate, subsequently reacting the anion of the thus-formed benzoate with 1-chloro-4-acetoxynonane to produce ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridecyl)benzoate followed by decarboxylation and alkaline hydrolysis to produce the desired product 4-(4-acetyl-8-hydroxytridecyl)benzoic acid which is useful as a pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.

Thermally developable light-sensitive material with a benzoic acid

Abstract: A thermally developable light-sensitive material with improved storage stability and a minimized thermal fog without an increase in both light discoloration and dark discoloration which comprises a support and having therein or in at least one layer thereon at least (a) an organic carboxylic acid silver salt comprising about 50 mol% or more of silver behenate, (b) a photocatalyst and (c) a reducing agent, and with the material containing (d) at least one compound (1) represented by the following general formula (I): ##STR1## wherein R1, R2 and R3, which may be the same or different, each represents a hydrogen atom or a substituent selected from the group consisting of a nitro group, a cyano group and a halogen atom, with the proviso that R1, R2 and R3 are not all simultaneously a hydrogen atom, and (2) having a half-neutralization point of from about 40 mV to about 140 mV above the half-neutralization point of benzoic acid in isopropanol.

Production of modified phenolic resin

Abstract: PURPOSE: A phenolic resin is modified with a modifier that is prepared by reacting an organic carboxylic acid or its derivative with both terminal hydroxyl groups of polyethylene glycol, thus producing said modified phenolic resin having high insulation property and not causing the formation of bulge. CONSTITUTION: To (A) a phenol and (B) an aldehyde is added (C) a modifier that is prepared by heating a polyethylene glycol of 300W1000 average molecular weight and a stoichiometric amount, based on the terminal hydroxyl groups, of an organic carboxylic acid or its derivative as benzoic acid, hydroxybenzoic acid or acetic acid at 150W160°C to effect dehydration until the theoretical amount of water is distilled off and the mixture is made to react in the presence of an alkaline catalyst. The amount of the modifier added is 20W150g per mol the phenol used. COPYRIGHT: (C)1980,JPO&Japio

Biosynthesis of benzaldehyde, benzyl alcohol and benzyl benzoate from benzoic acid in cranberry (vaccinium macrocarpon)

Abstract: The aroma complex of cranberry contains benzaldehyde, benzyl alcohol and benzyl benzoate as major components, and [7-14C] benzoic acid was converted into benzaldehyde, benzyl alcohol, benzyl benzoate, and minor amounts of other benzyl and benzoate esters in tissue slices of ripe cranberry. Hydrolysis of the benzyl benzoate indicated that label was about equally distributed between benzoic acid and benzyl alcohol. [7-14C] benzaldehyde was converted in tissue slices into benzyl alcohol and benzyl benzoate, and hydrolysis of the ester indicated that only the alcohol moiety was labeled. Incubation of cranberry tissue slices with [7-14C] benzyl alcohol yielded primarily benzyl benzoate, and only the alcohol portion of the ester was labeled. All biosynthetic products were identified by radio chromatographic analysis and by preparation of derivatives, and the direct incorporation of precursors into biosynthetic products was demonstrated by chemical degradation studies. These results strongly suggest that, in the biosynthesis of benzyl benzoate, benzoic acid is first reduced to benzaldehyde, followed by reduction of the aldehyde to benzyl alcohol which is subsequently esterified. None of the aforementioned transformations of [14C] benzoic acid and its derivatives could be demonstrated in tissue slices from unripe (green) cranberry, suggesting that development of the ability to synthesize volatile benzenoid compounds is associated with ripening.