Article pubs.acs.org/jced
Measurement and Correlation Studies of the Saturated Vapor Pressure, Density, Refractive Indices, and Viscosity of Methyl 4-tertButylbenzoate Vineet Aniya,†,‡ Ramesh Tangirala,† Prathap K. Thella,†,‡ and Bankupalli Satyavathi*,†,‡ †
Chemical Engineering Division, and ‡Academy of Scientific and Innovative Research (AcSIR), CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, 500007, India S Supporting Information *
ABSTRACT: The saturated vapor pressure of methyl 4-tertbutylbenzoate was measured from (1.21 to 34.66) kPa in the temperature range from (398.3 to 492.4) K using a Swietoslawski-type ebulliometer. The experimental data were fitted with the Antoine and Clarke−Glew equations, which yielded Antoine parameters (A = 18.031, B = 7261.445, C = 8.857 K) and standard vaporization enthalpy (Δgl Hθm (298.15 K) = 57.49 kJ mol−1), respectively. The critical properties were estimated on the basis of group contribution method. The acentric factor was calculated using these critical parameters and the saturated vapor pressures with the Antione equation. Furthermore, density, refractive indices, and viscosity of methyl 4tert-butylbenzoate were also measured in the temperature range of 293.15 to 353.15 K. Temperature-dependence correlation equations for the density (second-order polynomial equation) and viscosity (Vogel−Tamman−Fulcher) were proposed. Modified Rackett equation was used with group contribution methods to predict the density of methyl 4-tert-butylbenzoate. Group contributions and group interactions method of Nannoolal et al. were used to predict the viscosity in the temperature range of 293.15 to 353.15 K.
1. INTRODUCTION Methyl 4-tert-butylbenzoate (benzoic acid, p-tert-butyl-, methyl ester) is a useful synthetic chemical of commercial importance that finds applications in the pharmaceuticals, perfumes, flavor, cosmetics, and fragrance industries. It is used specifically for the preparation of valuable products such as Avobenzone (Claisen condensation of 4-methoxyacetophenone and methyl 4-tertbutylbenzoate), 2,3-dihydrobenzofuran-3-ylacetic acid (aryl radical cyclization-carboxylation of 2-allyloxybromobenzenes using methyl 4-tert-butylbenzoate) and tris(4-tert-butylphenyl) methyl chloride (reaction of methyl 4-tert-butylbenzoate with the Grignard reagent).1−3 Methyl 4-tert-butylbenzoate can be synthesized from methyl aromatics (4-tert-butyltoluene) by aerobic photo-oxidation using anthraquinone-2,3-dicarboxylic acid as an organophotocatalyst.4 Synthesis based on electrochemical oxidation of the corresponding methylbenzenes or benzaldehyde dialkyl acetals in the presence of an alkanol (4tert-butyl toluene) and of a halogenated triarylamine (tris(2,4dibromophenyl)-amine) derivative are also reported.5 In general, methyl 4-tert-butylbenzoate is produced by esterification of para-tert-butyl benzoic acid with methanol in the presence of acidic catalysts such as titanium sulfate, paratoluene sulfonic acid, ferric chloride, and dimethyl piperazine.6−9 The esterification reaction is followed by purification of the product via a distillation process. In the design and operation of such multicomponent separations, the pure thermodynamic and transport properties such as saturated © XXXX American Chemical Society
vapor pressure, molar enthalpy of vaporization, density, and viscosity plays a vital role. However, limited data have been reported on the properties of methyl 4-tert-butylbenzoate which is insufficient and inconsistent with larger differences found among the reported data. Bryan et al.10 reported a vapor pressure of 2 mmHg at 378−379 K. Van Zanten et al.11 reported 409−411 K as the equilibrium temperature for a vapor pressure of 16 mmHg. Ikuzo et al.12 and Barbara Roth et al.13 reported an equilibrium temperature of 383−385 K and 403 K at a vapor pressure 5 and 10 mmHg, respectively. Furthermore, Bryan et al.10 reported the density and refractive index at 293 K only. Also, in the Chemical Abstracts Service database only predicted results of parameters calculated from Advanced Chemistry Development (ACD) software have been provided.14 A comparison of experimental data and that predicted by ACD software indicates that significant differences exist for almost all high boiling point chemicals. For example, the experimental normal boiling point of ethylphenyldiethoxysilane (CAS RN: 16522-50-2) is in the range (512.35−512.59) K, whereas the predicted result is given by ACD software is 526.75 ± 9.0 K. Therefore, for precision in the design of industrial applications involving methyl 4-tert-butylbenzoate, the accurate Received: June 8, 2016 Accepted: November 7, 2016
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DOI: 10.1021/acs.jced.6b00470 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Journal of Chemical & Engineering Data
Article
Table 1. General Information of Methyl 4-tert-Butylbenzoate Used in the Present Study density g·cm−3 (293.15 K)
chemical name Methyl 4-tertbutylbenzoate a
molecular weight 192.25
CAS registry number 26537-19-9
source SigmaAldrich
initial mass purity 0.990
final mass fraction purity
purification method vacuum distillation
0.9980
water content mass fraction
