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. 2022 May 19;7(21):17670-17678.
doi: 10.1021/acsomega.2c00525. eCollection 2022 May 31.

Vapor-Liquid Equilibrium Study of the Monochlorobenzene-4,6-Dichloropyrimidine Binary System

Eniko Haaz  1 , Daniel Fozer  2 , Ravikumar Thangaraj  3   4 , Milán Szőri  3 , Peter Mizsey  3 , Andras Jozsef Toth  1
Affiliations

Vapor-Liquid Equilibrium Study of the Monochlorobenzene-4,6-Dichloropyrimidine Binary System

Eniko Haaz et al. ACS Omega. .

Abstract

The number of newly synthesized and produced organic chemicals has increased extremely quickly. However, the measurements of their physical properties, including their vapor-liquid equilibrium (VLE) data, are time-consuming. It so happens that there is no physical property data about a brand-new chemical. Therefore, the importance of calculating their physicochemical properties has been playing a more and more important role. 4,6-Dichloropyrimidine (DCP) is also a relatively new molecule of high industrial importance with little existing data. Therefore, their measurements and the comparison with the calculated data are of paramount concern. DCP is a widespread heterocyclic moiety that is present in synthetic pharmacophores with biological activities as well as in numerous natural products. Isobaric VLE for the binary system of 4,6-dichloropyrimidine and its main solvent monochlorobenzene (MCB) was measured using a vapor condensate and liquid circulation VLE apparatus for the first time in the literature. Density functional-based VLE was calculated using the COSMO-SAC protocol to verify the laboratory results. The COSMO-SAC calculation was found to be capable of representing the VLE data with high accuracy. Adequate agreement between the experimental and calculated VLE data was acquired with a minimal deviation of 3.0 × 10-3, which allows for broader use of the results.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Phosgenation of 4,6-dihydroxypyrimidine to produce 4,6-dichloropyrimidine (DCP).
Figure 2
Figure 2
VLE experimental apparatus (1, liquid container; 2, boiler tube; 3, Cotrell pump; 4, thermometer well; 5, equilibrium chamber; 6, vapor condenser; 7, vapor sampler; 8, liquid sampler; 9, condensers with vacuum connections). The photograph was taken by Andras Jozsef Toth. Copyright 2022.
Figure 3
Figure 3
Experimental refractive indexes of the acetonitrile (1)–water (2) system at T = 293.2 K (●). x1: mole fraction of acetonitrile.
Figure 4
Figure 4
y–x Diagram for acetonitrile (1)–water (2) system at 101 kPa: (gray circle solid) experimental and (●) literature.
Figure 5
Figure 5
T–y–x diagram for acetonitrile (1)–water (2) system at 101 kPa: (gray circle solid) experimental and (●) literature.
Figure 6
Figure 6
y–x Diagram for the monochlorobenzene (1)–4,6-dichloropyrimidine (2) system at P = 101 kPa with the experimental data (●), COSMO-SAC data (gray circle solid), and UNIFAC model (−).
Figure 7
Figure 7
T–y–x diagram for the monochlorobenzene (1)–4,6-dichloropyrimidine (2) system at P = 101 kPa with the experimental data (●), COSMO-SAC data (gray circle solid), and UNIFAC model (−).
See this image and copyright information in PMC

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