Aromatic Substitution: Part Viii. Some Aspects of the Mechanism of the Tschitschibabin Reaction

Abramovitch, R. A.; Helmer, Friederike; Saha, J. G.

doi:10.1139/v65-097

Cited by 23 publications

(5 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Abramovitch et al reported a boiling temperature range of (373.15 to 376.15) K at a reduced pressure of 1.47 kPa. Buckingham et al reported two boiling temperatures, (375.15 to 376.15) K at 1.47 kPa and 495 K at 99.73 kPa, which are in good agreement with the data of this work, 374.67 K at 1.47 kPa and 495.13 K at 99.74 kPa.…”

Section: Resultsmentioning

confidence: 99%

“…Materials. 2-Amino-3-methylpyridine was prepared using o -xylene as solvent according to the literature. , It was purified prior to use by distillation under reduced pressure. Its mass fraction purity, determined by gas chromatography equipped with a flame ionization detector (FID), was higher than 99.5 %.…”

Section: Methodsmentioning

confidence: 99%

“…The product of 2-amino-3methylpyridine with high purity is obtained by vacuum distillation. 4,5 Unfortunately, a literature survey revealed that only limited vapor pressure data 5,6 on this compound were available. In addition, there is no report on the enthalpy of vaporization of 2-amino-3-methylpyridine as far as we know.…”

Section: Introductionmentioning

confidence: 99%

“…2-Amino-3-methylpyridine (CASRN 1603-40-3) is used as an intermediate for manufacturing pharmaceuticals. − It is usually prepared by the Chichibabin reaction between 3-methylpyridine (CASRN 108-99-6) and sodium amide (CASRN 7782-92-5) in an organic solvent. The product of 2-amino-3-methylpyridine with high purity is obtained by vacuum distillation. , Unfortunately, a literature survey revealed that only limited vapor pressure data , on this compound were available. In addition, there is no report on the enthalpy of vaporization of 2-amino-3-methylpyridine as far as we know.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Vapor Pressure and Enthalpy of Vaporization of 2-Amino-3-methylpyridine

et al. 2007

View full text Add to dashboard Cite

The vapor pressure of 2-amino-3-methylpyridine was measured in the temperature range of (328.70 to 499.88) K using the boiling point method. The Antoine equation was used to describe the vapor pressure data, and the parameters in the equation were determined by means of the least-square regression method. The deviation of experimental data from the corresponding calculated values was within 0.30 %. On the basis of the equation, the enthalpy of vaporization of 2-amino-3-methylpyridine at normal boiling point (T b ) was obtained from the slope of the plot of ln p vs 1/T. The standard enthalpy of vaporization ∆ vap H(298.15 K) was estimated by Othmer's method. Using 3-methylpyridine as the standard substance, the value of ∆ vap H(298.15 K) was found to be 62.58 kJ‚mol -1 . A parallel value of ∆ vap H(298.15 K) was also obtained using benzene as the standard substance. Additionally the Watson relation was employed to verify the value of ∆ vap H(298.15 K), from which it was shown that the value of the standard enthalpy of vaporization was acceptable.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Vapor Pressure and Enthalpy of Vaporization of 2-Amino-3-methylpyridine

et al. 2007

View full text Add to dashboard Cite

show abstract

“…2-Amino-3-methylpyridine (boiling point, (221 to 222) °C) is a useful intermediate for manufacturing pharmaceuticals. − It is usually prepared by the Chichibabin reaction between 3-methylpyridine and sodium amide in N , N -dimethylaniline. − The yield of 2-amino-3-methylpyridine is more than 80 % by analyzing the composition of the reacted mixture, which contains some solvent and other byproducts. Therefore, the separation of 2-amino-3-methylpyridine from the binary mixture becomes an essential problem.…”

Section: Introductionmentioning

confidence: 99%

Vapor−Liquid Equilibrium for the Binary System ofN,N-Dimethylaniline with 2-Amino-3-methylpyridine

Zeng¹,

Kong²,

Xue³

et al. 2011

J. Chem. Eng. Data

View full text Add to dashboard Cite

The isobaric vapor−liquid equilibrium (VLE) data of the binary system N,N-dimethylaniline + 2-amino-3-methylpyridine were collected at (5.158 and 8.041) kPa. The activity coefficients of the system were correlated with the Van Laar and UNIQUAC models. The results showed that the calculated values of the vapor phase mole fraction and boiling temperature by the two models agreed well with the experimental data. Furthermore, the activity coefficients at infinite dilution were also presented. The VLE data were shown to be thermodynamically consistent by both the Herington consistency and point consistency tests.

show abstract

Pyridine and Pyridine Derivatives

Shimizu¹,

Watanabe²,

Kataoka³

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

View full text Add to dashboard Cite

The article contains sections titled: 1. Introduction 2. Pyridine and Alkylpyridines 2.1. Properties 2.2. Production 2.2.1. Separation from Tar 2.2.2. Synthesis from Aldehydes or Ketones with Ammonia 2.2.3. Synthesis from Acrylonitrile and Ketones 2.2.4. Synthesis from Dinitriles 2.2.5. Dealkylation of Alkylpyridines 2.2.6. Synthesis of 5‐Ethyl‐2‐Methylpyridine from Paraldehyde and Ammonia 2.2.7. Synthesis from Nitriles and Acetylene 2.2.8. Other Synthetic Methods 2.3. Quality Specifications, Storage, and Transportation 2.4. Uses 2.5. Economic Aspects 3. Pyridine Derivatives 3.1. Vinylpyridines 3.2. Bipyridines 3.3. Quaternary Pyridinium Salts 3.4. Pyridine N ‐Oxides 3.5. Piperidines 3.6. Halopyridines 3.7. Pyridinecarbonitriles, Carboxylic Acids, and Carboxamides 3.8. Aminopyridines 3.8.1. 2‐Aminopyridine 3.8.2. Other Aminopyridines 3.9. Pyridinols 3.10. Pyridyl Alcohols 3.11. Pyridinecarbaldehydes 3.12. Pharmaceuticals and Agrochemicals 4. Toxicology 4.1. Acute Toxicity 4.2. Subacute and Chronic Toxicity 4.3. Mutagenicity and Ecotoxicity

show abstract

Aromatic Substitution: Part Viii. Some Aspects of the Mechanism of the Tschitschibabin Reaction

Cited by 23 publications

References 17 publications

Vapor Pressure and Enthalpy of Vaporization of 2-Amino-3-methylpyridine

Vapor Pressure and Enthalpy of Vaporization of 2-Amino-3-methylpyridine

Vapor−Liquid Equilibrium for the Binary System ofN,N-Dimethylaniline with 2-Amino-3-methylpyridine

Pyridine and Pyridine Derivatives

Contact Info

Product

Resources

About