Acid-Base Reactions in Non-dissociating Solvents. Acetic Acid and Triethylamine in Carbon Tetrachloride and Chloroform

Barrow, Gordon M.; Yerger, E. Anne

doi:10.1021/ja01649a080

Cited by 133 publications

(65 citation statements)

References 3 publications

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“…This was also theoretically predicted by ab initio calculations for the trimethylamine-formic acid and propylamine-propionic acid systems [22,30]. The ionic nature of the complexes was confirmed by both mid and near infrared spectroscopy [20,21,[24][25], FT-Raman [17], 1 H-NMR and 13 C-NMR [15,31], dielectric spectroscopy, conductivity measurements [18,23], melting and boiling point measurements, ultrasound absorption and relaxation spectroscopy [12,24,[32][33], and combinations of different measurement techniques including density, optical refractive index, and shear viscosity [23].…”

Section: Introductionsupporting

confidence: 67%

“…Amines and carboxylic acid mixtures interact strongly via hydrogen bonding [12,15]. In 1:1 mixtures they form A 1 C 1 molecular complexes in the vapor phase [19][20][21][22][23][24][25][26][27][28][29][30] or ionic complexes in the liquid phase via Brønsted-Lowry acid-base reactions [17]. The A 1 C 1 ionic complex requires stabilization and ab initio calculations showed that, at equimolar mixing ratios, the formation of an A 2 C 2 complex is more likely [17].…”

Section: Introductionmentioning

confidence: 99%

“…Ternary systems comprising amines and carboxylic acids dissolved in non-ionizing or nondissociating solvents such as chloroform, carbon tetrachloride and benzene, have been studied as well [25][26][27][28]. Near UV absorption studies indicated proton transfer from the carboxylic acids to the amine [29].…”

Section: Introductionmentioning

confidence: 99%

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TGA–FTIR study of the vapors released by triethylamine–acetic acid mixtures

2012

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Proprietary mixtures of amines and carboxylic acids are used as volatile corrosion inhibitors (VCIs) for the protection of iron and steel components against atmospheric corrosion. This study was focused on the nature of the vapors they release. VCI model compounds comprising mixtures of triethylamine and acetic acid were studied using thermogravimetric analysis coupled with Fourier-transform infrared spectroscopy (TGA-FTIR) at 50°C. As vaporization progressed, the composition of the remaining liquid and the emitted vapor con v erged to a f i xed ami ne con ten t of ca. 27 m ol e percen t. Thi s was j ust ab ov e th e composition expected for the 1:3 amine to carboxylic acid complex. Mixtures close to this composition also featured the lowest volatility.

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Section: Introductionsupporting

confidence: 67%

Section: Introductionmentioning

confidence: 99%

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TGA–FTIR study of the vapors released by triethylamine–acetic acid mixtures

2012

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“…The first acid molecule interacts directly with the phosphate molecule to form an ion pair, and the OH of the carboxyl group of the second acid molecule forms a hydrogen bond with the conjugate CO of the carboxylate of the first acid molecule to form 2:1 complex, and it is not dependent on the ionisation strength of acid (pK a ). 43 Influence of extractant concentration on equilibrium pH and extraction efficiency Equilibrium pH in the reactive extraction of phenylacetic acid depends on concentration of tri-nbutyl phosphate, and was found to increase up to 3.40-3.44 due to transfer of acid molecule into organic phase. From Figs.…”

Section: Resultsmentioning

confidence: 99%

“…Scare literature is available on spectroscopic studies between acid-extractant complex 20,[33][34][35] and reactive extraction of phenylacetic acid. [36][37][38] In the present work, the data on stoichiometric and spectroscopic analysis of reactive extraction of phenylacetic acid with tri-n-butyl phosphate at interface of aqueous and organic phase the data are presented in terms of extraction efficiency, distribution coefficient, loading factor, and overall equilibrium constant.…”

Section: Stoichiometric and Spectroscopic Study Of Reactive Extractiomentioning

confidence: 99%

Stoichiometric and Spectroscopic Study of Reactive Extraction of Phenylacetic Acid with Tri-n-Butyl Phosphate

Athankar¹

2015

Chem. Biochem. Eng. Q.

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Phenylacetic acid is widely used in the pharmaceutical industry for production of antibiotics. The recovery of phenylacetic acid from dilute aqueous waste with tri-n-butyl phosphate in methyl isobutyl ketone and petroleum ether has been attempted, and the results are presented in terms of distribution coefficient, extraction efficiency, apparent equilibrium constant, and loading ratio. The mechanism of reactive extraction was analyzed and the stoichiometric ratio of phenylacetic acid to tri-n-butyl phosphate in methyl isobutyl ketone and petroleum ether was found to be 1:0.5 and 1:1.2. Mass action law was used to represent the reactive extraction equilibrium for phenylacetic acid−tri-n-butyl phosphate−diluents which satisfied much in the present study. FTIR spectroscopy was studied for confirmation of the formation of a complex between acid and extractant. Further relative basicity approach has been extended to represent the experimental results. The model is best suited to experimental results.

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Hydrogen-bonding-based thermochromic phenol-amine complexes

Mizutani

Takagi

Ueno

et al. 1998

J. Phys. Org. Chem.

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Variable-temperature UV-vis, 13 C NMR and IR studies showed that proton-transferred complexes were formed between phenols and amines in apolar solvents at low temperature. Upon cooling a solution of pnitrophenol and diisopropylamine in toluene, the colour of the solution changed from colourless to yellow. This thermochromism was ascribed to the proton transfer in the hydrogen-bonding complex. Under UV-vis conditions, butylamine and imidazole also caused similar thermochromism upon complexation with p-nitrophenol, while triethylamine, quinuclidine and pyridine did not. The thermochromic behaviour was particularly dependent on the stoichiometry of the amine and the phenol: a solution of 3,3'-dibromo-5,5'-dinitro-2,2'-biphenyldiol and diisopropylamine with a molar ratio of 1:1 showed no thermochromism, while solutions with 1:2 or higher ratios showed thermochromism, indicating that excess amine is required to obtain the proton-transferred species. These results revealed that the proton-transferred species forms in apolar solvents at low temperature if an appropriate hydrogen-bonding network between the phenol and the amine can stabilize it.

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Acid-Base Reactions in Non-dissociating Solvents. Acetic Acid and Triethylamine in Carbon Tetrachloride and Chloroform

Cited by 133 publications

References 3 publications

TGA–FTIR study of the vapors released by triethylamine–acetic acid mixtures

TGA–FTIR study of the vapors released by triethylamine–acetic acid mixtures

Stoichiometric and Spectroscopic Study of Reactive Extraction of Phenylacetic Acid with Tri-n-Butyl Phosphate

Hydrogen-bonding-based thermochromic phenol-amine complexes

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