Organization of Coupled Processes of Hydrocarboxylation of Alkenes of Various Nature

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The regularities of the alkene hydrocarboxylation process in conjugation with the carbon monoxide oxidation reaction in the PdBr2–CuBr2–THF–H2O catalytic system were studied. Cyclohexene, styrene, 1-hexene, 1-octene, 4-vinylcyclohexene, ethylene, propylene, vinyl acetate, vinyl butyl ether were used as substrates. The obtained products were identified by gas chromatography and chromatograph mass spectrometry.

Full Text

Restricted Access

About the authors

А. Y. Putin

MIREA – Russian Technological University, Lomonosov Institute of Fine Chemical Technologies

Author for correspondence.
Email: putinalekse@yandex.ru
Russian Federation, 86 Vernadsky Ave., Moscow, 119571

D. N. Novak

MIREA – Russian Technological University, Lomonosov Institute of Fine Chemical Technologies

Email: putinalekse@yandex.ru
Russian Federation, 86 Vernadsky Ave., Moscow, 119571

L. G. Bruk

MIREA – Russian Technological University, Lomonosov Institute of Fine Chemical Technologies

Email: putinalekse@yandex.ru
Russian Federation, 86 Vernadsky Ave., Moscow, 119571

References

  1. Badea G.-I., Radu G.L. Carboxylic acid: key role in life sciences. IntechOpen, 2018. 94 p.
  2. Фальбе Ю. Синтезы на основе окиси углерода. Ленинград: Химия, 1971. 216 с.
  3. Yuan Q., Song X., Feng S., Jiang M., Yan L., Li J., Ding Y. // Chem. Commun. 2021. V. 57. № 4. P. 472.
  4. Брук Л.Г., Темкин О.Н. // Кинетика и катализ. 2016. Т. 57. № 3. С. 275. (Bruk L.G., Temkin O.N. // Kinet. Catal. 2016. V. 57. № 3. P. 277.)
  5. Севостьянова Н.Т., Баташев С.А., Родионова А.С. // Тонкие химические технологии. 2023. Т. 18. № 1. С. 29. (Sevostyanova N.T., Batashev S.A., Rodionova A.S. // Tonk. Khim. Tekhnol. (Fine Chem. Technol.) 2023. V. 18. № 1. P. 29.)
  6. Путин А.Ю., Кацман Е.А., Брук Л.Г. // Кинетика и катализ. 2023. Т. 64. № 4. С. 408. ( Putin A.Yu., Katsman E.A., Bruk L.G. // Kinet. Catal. 2023. V. 64. № 4. P. 412.)
  7. Тимашова Е.А., Путин А.Ю., Бычкова Е.Ю., Брук Л.Г., Темкин О.Н., Ошанина И.В. // Вестн. МИТХТ. 2014. Т. 9. № 3. С. 57.
  8. Путин А.Ю., Бычкова Е.Ю., Трунилина К.В., Закгейм А.Ю., Кацман Е.А., Шишилов О.Н., Ахмадуллина Н.С., Ошанина И.В., Темкин О.Н., Брук Л.Г. // Журн. физ. химии. 2015. Т. 89. № 3. С. 373. (Putin A. Yu., Bychkova E.Yu., Trunilina K.V., Zakgeim A.Y., Katsman E.A., Shishilov O.N., Oshanina I.V., Temkin O.N., Bruk L.G., Akhmadullina N.S. // Russ. J. Phys. Chem. A. 2015. V. 89. № 3. P. 359.)
  9. Справочник химика. Под ред. Б.П. Никольского. Москва–Ленинград: Химия, 1965. Т. 3.
  10. Патент US4377708A, 1983.
  11. Брук Л.Г., Темкин О.Н., Абдуллаева А.С., Тимашова Е.А., Букина Е.Ю., Одинцов К.Ю., Ошанина И.В. // Кинетика и катализ. 2010. Т. 51. № 5. С. 702. (Bruk L.G., Temkin O.N., Abdullaeva A.S., Timashova E.A., Bukina E.Yu., Odintsov K.Yu., Oshanina I.V. // Kinet. Catal. 2010. V. 51. № 5. P. 678.)

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Fig. 1. Effect of ethylene introduction on the rate of CO2 formation. Conditions: THF, 30°C, [PdBr2] = 0.005 M, [CuBr2] = 0.015 M, [H2O] = 0.6 M, initial ratio CO : O2 : C2H4 ≈ 1 : 1 : 1.

Download (12KB)
Indexing metadata
3. Fig. 2. Evolution of the IR spectra of the contact solution during the process of propylene hydrocarboxylation. Conditions: [PdBr2] = 0.005 M; [CuBr2] = 0.015 M; [H2O] = 0.2 M, PCO : PO2 ≈ 1 : 1.

Download (36KB)
Indexing metadata
4. Fig. 3. Dependences of the formation rates of CO2 (a), isobutyric acid (b) and n-butyric acid (c) on the polar effect.

Download (23KB)
Indexing metadata
5. Fig. 4. Dependences of the rates of formation of CO2 (a), isobutyric acid (b) and n-butyric acid (c) on the steric effect.

Download (23KB)
Indexing metadata
6. Scheme 1. Proposed scheme of the coupled process of vinyl acetate hydrocarboxylation and subsequent production of lactic acid.

Download (19KB)
Indexing metadata
7. Scheme 2. Probable mechanism of formic acid formation.

Download (9KB)
Indexing metadata
8. Scheme 3. Proposed mechanism of formation of acrylic and propionic acids.

Download (17KB)
Indexing metadata
9. Scheme 4. Proposed scheme of the coupled process of hydrocarboxylation of vinyl butyl ether and subsequent formation of lactic acid.

Download (15KB)
Indexing metadata