<i>Para-tert</i>-butylcumene synthesis
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...
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| Format: | Article |
| Language: | Russian |
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MIREA - Russian Technological University
2021-03-01
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| Series: | Тонкие химические технологии |
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| Online Access: | https://www.finechem-mirea.ru/jour/article/view/1685 |
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| author | E. M. Yarkina E. A. Kurganova A. S. Frolov G. N. Koshel T. N. Nesterova V. A. Shakun S. A. Spiridonov |
| author_facet | E. M. Yarkina E. A. Kurganova A. S. Frolov G. N. Koshel T. N. Nesterova V. A. Shakun S. A. Spiridonov |
| author_sort | E. M. Yarkina |
| collection | DOAJ |
| description | 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%. |
| format | Article |
| id | doaj-art-d82b1f1d487e430fb7cd6722eabda48a |
| institution | DOAJ |
| issn | 2410-6593 2686-7575 |
| language | Russian |
| publishDate | 2021-03-01 |
| publisher | MIREA - Russian Technological University |
| record_format | Article |
| series | Тонкие химические технологии |
| spelling | doaj-art-d82b1f1d487e430fb7cd6722eabda48a2025-08-20T03:23:07ZrusMIREA - Russian Technological UniversityТонкие химические технологии2410-65932686-75752021-03-01161263510.32362/2410-6593-2020-16-1-26-351623<i>Para-tert</i>-butylcumene synthesisE. M. Yarkina0E. A. Kurganova1A. S. Frolov2G. N. Koshel3T. N. Nesterova4V. A. Shakun5S. A. Spiridonov6Yaroslavl State Technical UniversityYaroslavl State Technical UniversityYaroslavl State Technical UniversityYaroslavl State Technical UniversitySamara State Technical UniversitySamara State Technical UniversitySamara State Technical UniversityObjectives. 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%.https://www.finechem-mirea.ru/jour/article/view/1685para-tert-butylcumeneisobutylenetert-butyl alcoholalkylation |
| spellingShingle | E. M. Yarkina E. A. Kurganova A. S. Frolov G. N. Koshel T. N. Nesterova V. A. Shakun S. A. Spiridonov <i>Para-tert</i>-butylcumene synthesis Тонкие химические технологии para-tert-butylcumene isobutylene tert-butyl alcohol alkylation |
| title | <i>Para-tert</i>-butylcumene synthesis |
| title_full | <i>Para-tert</i>-butylcumene synthesis |
| title_fullStr | <i>Para-tert</i>-butylcumene synthesis |
| title_full_unstemmed | <i>Para-tert</i>-butylcumene synthesis |
| title_short | <i>Para-tert</i>-butylcumene synthesis |
| title_sort | i para tert i butylcumene synthesis |
| topic | para-tert-butylcumene isobutylene tert-butyl alcohol alkylation |
| url | https://www.finechem-mirea.ru/jour/article/view/1685 |
| work_keys_str_mv | AT emyarkina iparatertibutylcumenesynthesis AT eakurganova iparatertibutylcumenesynthesis AT asfrolov iparatertibutylcumenesynthesis AT gnkoshel iparatertibutylcumenesynthesis AT tnnesterova iparatertibutylcumenesynthesis AT vashakun iparatertibutylcumenesynthesis AT saspiridonov iparatertibutylcumenesynthesis |