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Para-tert-butylcumene synthesis

https://doi.org/10.32362/2410-6593-2020-16-1-26-35

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Abstract

Objectives. This study describes a new approach to obtain para-tert-butylcumene by alkylation of cumene with isobutylene in the presence of catalysts, such as Amberlyst 36 Dry, KU-2-8, aluminum chloride, and tert-butyl alcohol and concentrated sulfuric acid.

Methods. To determine the qualitative and quantitative composition of the compounds and reaction masses, the following analysis methods were used: gas–liquid chromatography (on the Kristall 2000M hardware-software complex), chromatomass spectrometry on an Agilent 6850 instrument equipped with an Agilent 19091S-433E capillary column (30 m × 250 μm × 0.25 μm), and nuclear magnetic resonance spectroscopy (on a Bruker DRX 400 instrument with an operating frequency of 400 MHz).

Results. A significant quantity of meta-tert-butylcumene was obtained by the alkylation of cumene with isobutylene using several catalysts, along with para-tert-butylcumene. This study also showed that the use of the catalysts Amberlyst 36 Dry and KU-2-8 during alkylation in a closed system (autoclave) led to the formation of isobutylene oligomers, often in quantity greater than the target reaction product. Simultaneously, the alkylation of cumene with tert-butyl alcohol in the presence of concentrated sulfuric acid enabled the obtainment of only one isomer, para-tertbutylcumene, which is essential for the further production of high-purity para-tert-butyl phenol.

Conclusions. Sulfuric acid alkylation of cumene with tert-butyl alcohol enabled the obtainment of an individual para-isomer of tert-butylcumene with a yield of 87–89% for the loaded tert-butyl-alcohol with a cumene conversion of ~30%.

About the Authors

E. M. Yarkina
Yaroslavl State Technical University
Russian Federation

Elizaveta M. Yarkina, Postgraduate Student, Department of General and Physical Chemistry

88, Moskovskii pr., Yaroslavl, 150023



E. A. Kurganova
Yaroslavl State Technical University
Russian Federation

Ekaterina A. Kurganova, Dr. Sci. (Chem.), Professor, Department of General and Physical Chemistry. ResearherID B-4021-2018, Scopus Author ID 24338325800

88, Moskovskii pr., Yaroslavl, 150023



A. S. Frolov
Yaroslavl State Technical University
Russian Federation

Aleksandr S. Frolov, Cand. Sci. (Chem.), Senior Lecturer, Department of General and Physical Chemistry. ResearherID I-8533-2018, Scopus Author ID 56412435400

88, Moskovskii pr., Yaroslavl, 150023



G. N. Koshel
Yaroslavl State Technical University
Russian Federation

Georgiy N. Koshel, Dr. Sci. (Chem.), Professor, Department of General and Physical Chemistry. ResearherID I-7782-2017, Scopus Author ID 6506863584

88, Moskovskii pr., Yaroslavl, 150023



T. N. Nesterova
Samara State Technical University
Russian Federation

Tatyana N. Nesterova, Cand. Sci. (Chem.), Associate Professor, Professor, Department of Technology of Organic and Petrochemical Synthesis. Scopus Author ID 15045158000

244, Molodogvardeiskaya ul., Samara, 443100



V. A. Shakun
Samara State Technical University
Russian Federation

Vladimir A. Shakun, Assistant, Department of Technology of Organic and Petrochemical Synthesis. Scopus Author ID 56829536300

244, Molodogvardeiskaya ul., Samara, 443100



S. A. Spiridonov
Samara State Technical University
Russian Federation

Stanislav A. Spiridonov, Master Student, Department of Technology of Organic and Petrochemical Synthesis

244, Molodogvardeiskaya ul., Samara, 443100



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Supplementary files

1. Fig. 1. Alkylation reactor: (1) molybdenum glass reactor, (2) metal bearing, (3) swivel nut, (4) copper ring, (5) gasket seal.
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2. This is to certify that the paper titled Para-tert-butylcumene synthesis commissioned to us by Elizaveta M. Yarkina, Ekaterina A. Kurganova, Aleksandr S. Frolov, Georgiy N. Koshel, Tatyana N. Nesterova, Vladimir A. Shakun and Stanislav A. Spiridonov has been edited for English language and spelling by Enago, an editing brand of Crimson Interactive Inc.
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  • A significant quantity of meta-tert-butyl was formed by the alkylation of cumene with isobutylene using Amberlyst 36 Dry, KU-2-8 catalysts, and aluminum chloride, along with para-tert-butylcumene.
  • The use of Amberlyst 36 Dry and KU-2-8 catalysts during alkylation in a closed system (autoclave) led to the formation of isobutylene oligomers, often in quantity greater than the target reaction product.
  • The alkylation of cumene with tert-butyl alcohol in the presence of concentrated sulfuric acid enabled the obtainment of only one isomer, para-tert-butylcumene, which is essential for the further production of high-purity para-tert-butyl phenol.

For citation:


Yarkina E.M., Kurganova E.A., Frolov A.S., Koshel G.N., Nesterova T.N., Shakun V.A., Spiridonov S.A. Para-tert-butylcumene synthesis. Fine Chemical Technologies. 2021;16(1):26-35. https://doi.org/10.32362/2410-6593-2020-16-1-26-35

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