The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effect
Acetophenone is an important by-product for the manufacture of drugs of calming effect. Known methods of its production don't have the future due to technological complexity, harsh synthesis conditions and low processing coefficients of raw materials. Therefore, the development of low-waste, lo...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Zaporizhzhia State Medical and Pharmaceutical University
2020-05-01
|
| Series: | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| Subjects: | |
| Online Access: | http://pharmed.zsmu.edu.ua/article/view/198119/199115 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1839601441359003648 |
|---|---|
| author | A. H. Halstian A. S. Bushuiev V. V. Kotova O. O. Demchenko |
| author_facet | A. H. Halstian A. S. Bushuiev V. V. Kotova O. O. Demchenko |
| author_sort | A. H. Halstian |
| collection | DOAJ |
| description | Acetophenone is an important by-product for the manufacture of drugs of calming effect. Known methods of its production don't have the future due to technological complexity, harsh synthesis conditions and low processing coefficients of raw materials. Therefore, the development of low-waste, low-temperature synthesis of acetophenone with ozone is an urgent task.
The purpose of the work was to study the kinetic regularities of the reaction of ozone with ethylbenzene in acetic acid and to create the ozonolytic synthesis of acetophenone.
Materials and methods. Glacial acetic acid of “Sigma” firm of qualification "Ch. P."; ethylbenzene, acetophenone of “Acros Organics” firm of qualification “Ch. P.”; acetates of metals of qualification “Ch. P.” were applied. The concentration of O3 in the gas phase was determined by a spectrophotometric absorption method in the range of 254–290 nm on spectrophotometer SF-46, which was designed to measure the transmittance of liquid and solid transparent substances in the spectral range from 190 to 1100 nm. Identification of the components of the reaction mass and their quantitative analysis in solution was performed by gas-liquid chromatography.
Results. The kinetic regularities of the oxidation of ethylbenzene with ozone in a solution of glacial acetate have been investigated. It is shown that ozone occurs at a temperature of 15 °C, mainly by the aromatic ring. The addition into the catalyst system - manganese (II) acetate has increased the selectivity of oxidation on the side chain from 34.0 to 87.7 %. Acetophenone (76.5 %) and methylphenylcarbinolacetate (11.2 %) are formed as the main products.
Conclusions. Ozonation of ethylbenzene in acetic acid was taken place mainly on the aromatic ring, and it was not possible to obtain acetophenone in high yield. The addition of transition metals allowed to be directed the process along the side ring to form 76 % acetophenone. |
| format | Article |
| id | doaj-art-69fde553df1b4ea4906f9f8f33df1abf |
| institution | Matheson Library |
| issn | 2306-8094 2409-2932 |
| language | English |
| publishDate | 2020-05-01 |
| publisher | Zaporizhzhia State Medical and Pharmaceutical University |
| record_format | Article |
| series | Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki |
| spelling | doaj-art-69fde553df1b4ea4906f9f8f33df1abf2025-08-02T10:10:43ZengZaporizhzhia State Medical and Pharmaceutical UniversityAktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki2306-80942409-29322020-05-01131233010.14739/2409-2932.2020.1.198119The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effectA. H. Halstian0A. S. Bushuiev1V. V. Kotova2O. O. Demchenko3 Institute of Сhemical Technologies of Dahl East Ukrainian National University, Rubizhne, Ukraine State Enterprise “Lugansk State Medical University”, Rubizhne, Ukraine State Enterprise “Lugansk State Medical University”, Rubizhne, Ukraine State Enterprise “Lugansk State Medical University”, Rubizhne, UkraineAcetophenone is an important by-product for the manufacture of drugs of calming effect. Known methods of its production don't have the future due to technological complexity, harsh synthesis conditions and low processing coefficients of raw materials. Therefore, the development of low-waste, low-temperature synthesis of acetophenone with ozone is an urgent task. The purpose of the work was to study the kinetic regularities of the reaction of ozone with ethylbenzene in acetic acid and to create the ozonolytic synthesis of acetophenone. Materials and methods. Glacial acetic acid of “Sigma” firm of qualification "Ch. P."; ethylbenzene, acetophenone of “Acros Organics” firm of qualification “Ch. P.”; acetates of metals of qualification “Ch. P.” were applied. The concentration of O3 in the gas phase was determined by a spectrophotometric absorption method in the range of 254–290 nm on spectrophotometer SF-46, which was designed to measure the transmittance of liquid and solid transparent substances in the spectral range from 190 to 1100 nm. Identification of the components of the reaction mass and their quantitative analysis in solution was performed by gas-liquid chromatography. Results. The kinetic regularities of the oxidation of ethylbenzene with ozone in a solution of glacial acetate have been investigated. It is shown that ozone occurs at a temperature of 15 °C, mainly by the aromatic ring. The addition into the catalyst system - manganese (II) acetate has increased the selectivity of oxidation on the side chain from 34.0 to 87.7 %. Acetophenone (76.5 %) and methylphenylcarbinolacetate (11.2 %) are formed as the main products. Conclusions. Ozonation of ethylbenzene in acetic acid was taken place mainly on the aromatic ring, and it was not possible to obtain acetophenone in high yield. The addition of transition metals allowed to be directed the process along the side ring to form 76 % acetophenone.http://pharmed.zsmu.edu.ua/article/view/198119/199115ozonolysisethylbenzeneacetophenoneacetic acidoxidationcatalysisozone |
| spellingShingle | A. H. Halstian A. S. Bushuiev V. V. Kotova O. O. Demchenko The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effect Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki ozonolysis ethylbenzene acetophenone acetic acid oxidation catalysis ozone |
| title | The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effect |
| title_full | The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effect |
| title_fullStr | The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effect |
| title_full_unstemmed | The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effect |
| title_short | The ozonolytic synthesis of acetophenone - a by-product for the production of drugs of calming effect |
| title_sort | ozonolytic synthesis of acetophenone a by product for the production of drugs of calming effect |
| topic | ozonolysis ethylbenzene acetophenone acetic acid oxidation catalysis ozone |
| url | http://pharmed.zsmu.edu.ua/article/view/198119/199115 |
| work_keys_str_mv | AT ahhalstian theozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect AT asbushuiev theozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect AT vvkotova theozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect AT oodemchenko theozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect AT ahhalstian ozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect AT asbushuiev ozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect AT vvkotova ozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect AT oodemchenko ozonolyticsynthesisofacetophenoneabyproductfortheproductionofdrugsofcalmingeffect |