Z/E Isomerization of Acetylene Oxidative Carbmethoxylation Products and the Proposed Process Mechanism

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

A new catalytic system for the production of dimethyl maleate (DMM) and dimethyl fumarate (DMF) by acetylene oxidative carbomethoxylation is proposed. It is shown that in the PdBr2-LiBr – РсСо – MeOH system, DMM is predominantly formed. The effect of HBr, thiourea (Tu) and solvent additives on the rate of DMM Z/E isomerization reaction is studied. It is shown that the use of an additional organic solvent and a decrease in the methanol concentration increase in Z/E isomerization rate and leads to DMF formation. A mechanism for DMM, DMF and dimethyl succinate formation is proposed (DMS).

Texto integral

Acesso é fechado

Sobre autores

S. Prokhorov

MIREA – Russian Technological University

Autor responsável pela correspondência
Email: oshanina_i@mail.ru
Rússia, Moscow

Yu. Matrosova

MIREA – Russian Technological University

Email: oshanina_i@mail.ru
Rússia, Moscow

I. Oshanina

MIREA – Russian Technological University

Email: oshanina_i@mail.ru
Rússia, Moscow

Bibliografia

  1. Темкин О.Н. Гомогенный металлокомплексный катализ. Кинетические аспекты. Москва: ИКЦ “Академкнига”. 2008. 918 c. (Temkin O.N. Homogeneous Catalysis with Metal Complexes. Wiley, 2012. 806 р.)
  2. Темкин О.Н. “Золотой век” гомогенно-каталитической химии алкинов: димеризация и олигомеризация алкинов // Кинетика и катализ. 2019. Т. 60. № 6. С. 683. (Temkin O.N. “Golden Age” of Homogeneous Catalysis Chemistry of Alkynes: Dimerization and Oligomerization of Alkynes // Kinet. Catal. 2019. V. 60. № 6. P. 689.)
  3. Мехрякова Н.Г., Брук Л.Г., Калия О.Л., Темкин О.Н., Прудников А.Ю. О механизмах карбонилирования ацетилена в растворах комплексов палладия // Кинетика и катализ. 1979. Т. 20. № 3. С. 629.
  4. Темкин О.Н. О кинетических моделях многомаршрутных реакций в гомогенном металлокомплексном катализе. // Кинетика и катализ. 2012. Т. 53. № 3. С. 326. (Temkin O.N. Kinetic Models of Multi-Route Reactions in Homogeneous Catalysis with Metal Complexes (A Revew) // Kinet. Catal. 2012. V. 53. № 3. P. 313.)
  5. Брук Л.Г., Гарбузюк И.А., Маркина С.В., Отараку Д.И., Ошанина И.В., Паздерский Ю.А., Присяжнюк С.М., Романюк И.М., Темкин О.Н. Способ получения янтарного ангидрида. Патент RU 2044731 C1, 1995.
  6. Bruk L.G., Oshanina I.V., Kozlova A.P., Vorontsov E.V., Temkin O.N. Mechanistic Study of Acetylene Carbonylation to Anhydrides of Dicarboxylic Acids in Solutions of Palladium Complexes // J. Mol. Catal. A: Chem. 1995. V. 104. № 1. P. 9.
  7. Bruk L.G., Oshanina I.V., Kozlova A.P., Temkin O.N., Odintsov K.Yu. Mechanism of Synthesis of Maleic and Succinic Anhydrides by Carbonylation of Acetylene in Solutions of Palladium Complexes // Russ. Chem. Bull. 1998. V. 47. № 6. P. 1071.
  8. Temkin O.N., Bruk L.G. Palladium(II, I, 0) Complexes in Catalytic Reactions of Oxidative Carbonylation // Kinet. Catal. 2003. V. 44. № 5. P. 601.
  9. Bruk L.G., Oshanina I.V., Zakieva A.S., Kozlova A.P., Temkin O.N. Critical Phenomena in Homogeneous Catalytic Reaction of Acetylene Carbonylation to Maleic Anhydride // Kinet. Catal. 1998. V. 39. № 2. P. 167.
  10. Bruk L.G., Kozlova A.P., Marshakha O.V., Oshanina I.V., Temkin O.N., Kaliya O.L. New Catalytic Systems for Oxidative Carbonylation of Acetylene to Maleic Anhydride // Russ. Chem. Bull. 1999. V. 48. № 10. P. 1875.
  11. Емельянова Г.Р. Каталитический синтез янтарной кислоты и ее эфиров карбонилированием ацетилена. Дисс. …канд. хим. наук. Москва: МИТХТ, 1985.
  12. Roxanne P.S. Tecfidera: an Approach for Repurposing // Pharm. Pat. Anal. 2014. V. 3. № 2. P. 183.
  13. Рыжакова Е.Н., Шилов М.С., Лаврентьев В.В. Лекарственная форма в виде капсулы, содержащая таблетки с диметилфумаратом. Патент RU 2742745 C1, 2021.
  14. Kawashiri T, Miyagi A., Shimizu S., Shigematsu N., Kobayashi D., Shimazoe T. Dimethyl fumarate ameliorates chemotherapy agent-induced neurotoxicity in vitro // J. Pharmacol. Sci. 2018. V. 137. P. 202.
  15. Cai Z., Wan Y., Becker M.L., Long Y.-Z., Dean D. Poly(propylene fumarate)-based materials: Synthesis, functionalization, properties, device fabrication and biomedical applications // Biomaterials. 2019. V. 208. P. 45.
  16. Эльман А.Р., Корнеева Г.А., Носков Ю.Г., Хан В.Н., Шишкина Е.Ю., Негримовский В.М., Пономаренко Е.П., Кононов Л.О., Брук Л.Г., Ошанина И.В., Тёмкин О.Н., Кузьмин С.Г. Синтез продуктов, меченных изотопом 13С, для медицинской диагностики // Российский химический журнал. 2013. Т. 57. № 5. С. 3.
  17. Jensen P.R., Karlsson M., Meier S., Duus J.Ø., Lerche M.H. Hyperpolarized Amino Acids for In Vivo Assays of Transaminase Activity // Chem. Eur. J. 2009. V. 15. P. 10010.
  18. Takeuchi K., Ng E., Malia T.J., Wagner G. 1-13C amino acid selective labeling in a 2H15N background for NMR studies of large proteins // J. Biomol. NMR. 2007. V. 38. P. 89.
  19. Karlsson M., Jensen P.R., Duus J.Ø., Meier S., Lerche M.H. Development of Dissolution DNP-MR Substrates for Metabolic Research // Appl. Magn. Reson. 2012. V. 43. P. 223.
  20. Tadashi K., Isaburo H., Junko O., Asuka I., Kunihiko S. 13C-containing diagnostic agent for diabetes. EP913161A2, 1999.
  21. Alper H., Despeyroux B., Woell J.B. Selective Hydroesterification of Alkynes to Mono-or Diesters // Tetrahedron Lett. 1983. V. 24. P. 5691.
  22. Cassar L., Chiusoli G.P., Guerrieri F. Synthesis of Carboxylic Acids and Esters by Carbonylation Reactions at Atmospheric Pressure Using Transition Metal Catalysts // Synthesis. 1973. V. 509. P. 21.
  23. Gabriele B., Costa M., Salernoe G., Chiusoli G.P. An Efficient and Selective Palladium-catalysed Oxidative Dicarbonylation of Alkynes to Alkyl- or Arylmaleic Esters // J. Chem. Soc. Perkin Trans. 1994. V. 1. P. 83.
  24. We X., Ma Z., Lu J., Mu X., Hu B. The highly efficient and selective dicarbonylation of acetylene catalysed by palladium nanosheets supported on activated carbon // New J. Chem. 2020. V. 44. P. 11835.
  25. Li X., Feng S., Song X., Yuan Q., Li B., Ning L., Chen W., Li J., Ding Y. The Evolution of Single-Site Pd1/AC Catalyst During the Process of Acetylene Dialkoxycarbonylation // J. Catal. 2022. V. 413. P. 762.
  26. Li X., Feng S., Hemberger P., Bodi A., Song X., Yuan Q., Mu J., Li B., Jiang Z., Ding Y. Iodide-Coordinated Single-Site Pd Catalysts for Alkyne Dialkoxycarbonylation // ACS Catal. 2021. V. 11. P. 9242.
  27. Wei X., Ma Z., Lu J., Mu X. Hu B. Strong Metal-Support Interactions between Palladium Nanoclusters and Hematite Toward Enhanced Acetylene Dicarbonylation at Low Temperature // New J. Chem. 2020. V. 44. P. 2121.
  28. Wei X., Ma Z., Mu X., Zhanga Q., Hu B. Synergistic effect of hematite facet and Pd nanocluster for enhanced acetylene dicarbonylation // Mol. Catal. 2021. V. 499. P. 111303.
  29. Ошанина И.В., Голобородько С.И., Робинова Е.А., Руснак И.Н., Никифоров С.А., Прохоров С.А., Темкин О.Н., Калия О.Л. Окисление монооксида углерода кислородом в водно-ацетонитрильных растворах бромидных комплексов палладия(II) в присутствии фталоцианинатов Сo(II), Fe(II) и Mn(III) // Тонкие химические технологии. 2019. Т. 14. № 6. С. 76.
  30. Путин А.Ю., Кацман Е.А., Брук Л.Г. Кинетика и механизм реакции окисления СО В СО2 в каталитической системе PdBr2–CuBr2–ТГФ–Н2О // Кинетика и катализ. 2023. Т. 64. № 4. С. 408. (Putin A.Yu., Katsman E.A., Bruk L.G. Kinetics and Mechanism of the Oxidation of CO to CO2 in the PdBr2–CuBr2–THF–H2O Catalytic System // Kinet. Catal. 2023. V. 64. № 4. P. 412.)
  31. Ma Y.-L., Zhou R.-J., Zeng X.-Y., An Y.-X., Qiu S.-S., Nie L.-J. Synthesis, DFT and antimicrobial activity assays in vitro for novel cis/trans-but-2-enedioic acid esters // J. Mol. Struct. 2014. V. 1063. P. 226.
  32. Lima M.T., Finelli F.G., de Oliveira A.V.B., Kartnaller V., Cajaiba J.F., Leão R.A.C., de Souza R.O.M.A. Continuous-flow synthesis of dimethyl fumarate: a powerful small molecule for the treatment of psoriasis and multiple sclerosis // RSC Adv. 2020. V. 10. P. 2490.
  33. Putin A.Y., Katsman E.A., Bruk L.G. State of Palladium Complexes in the PdBr2–LiBr–CH3CN–H2O Catalytic System, Used to Obtain Succinic Anhydride // Russ. J. Phys. Chem. A. 2019. V. 93. № 2. P. 222.
  34. Tan E.H.P., Lloyd-Jones G.C., Harvey J.N., Lennox A.J.J., Mills B.M. [(RCN)2PdCl2]-Catalyzed E/Z Isomerization of Alkenes: A Non-Hydride Binuclear Addition–Elimination Pathway // Angew. Chem. Int. Ed. 2011. V. 50. P. 9602.
  35. Sakaki S., Kanai H., Tarama K. Isomerization of 1-Olefins by Dihalogenobis(nitrile)palladium Complexes [PdX2(RCN)2] // Can. J. Chem. 1974. V. 52. P. 2857.
  36. Zargarian D., Alper H. Palladium Chloride Catalyzed Dicarbonylation of Terminal Alkynes // Organometallics. 1991. V. 10. P. 2914.
  37. Gabriele B., Salernoe G., Costa M., Chiusoli G.P. //Combined Oxidative and Reductive Carbonylation of Terminal Alkynes with Palladium Iodide-Thiourea Catalysts // J. Organomet. Chem. 1995. V. 503. P. 21.
  38. Marcotrigiano G., Battistuzzi R., Peyronel G. Binuclear Halogen-bridged Complexes of Palladium(II) with Thiourea: Pd2Tu2X4 and their Bridge-Splitting Reactions // J. Inorg. Nucl. Chem. 1973. V. 5. P. 2265.

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Fig. 1

Baixar (12KB)
Metadados
3. Scheme 1. The junction of the stages of formation of MA and JA from the common intermediate HPd(MA)

Baixar (28KB)
Metadados
4. Fig. 2

Baixar (15KB)
Metadados
5. Fig. 3

Baixar (33KB)
Metadados
6. Fig. 1. Accumulation of products during oxidative carbmethoxylation of acetylene using PdBr2-LiBr-PcCo-MeOH catalytic system. Conditions: CPdBr2 = 0.03 M, CLiBr = 0.1 M, CPcCo = 0.03 M, gas composition in the reactor: PCO ≈ 54-56 kPa, PC2H2 ≈ 3-5 kPa, PO2 ≈ 5-6 kPa

Baixar (94KB)
Metadados
7. Fig. 2. Dependence of the initial rate of DMM and DMF formation during oxidative carbmethoxylation of acetylene using PdBr2-LiBr-PcCo-AN-MeOH catalytic system on the concentration of palladium bromide. Conditions: CLiBr = 0.1 M, CPcCo = 0.03 M, αMeOH = 0.55, reactor gas composition: PCO ≈ 42-49 kPa, PC2H2 ≈ 7-12 kPa, PO2 ≈ 6.5-8 kPa

Baixar (76KB)
Metadados
8. Fig. 3. Dependence of the initial rate of DMM and DMF formation in the process of oxidative carbmethoxylation of acetylene using PdBr2-LiBr-PcCo-AN-MeOH catalytic system on the content of cobalt phthalocyanine complex. Conditions: CPdBr2 = 0.03 M, CLiBr = 0.1 M, αMeOH = 0.55, gas composition in the reactor: PCO ≈ 46-50 kPa, PC2H2 ≈ 5-10 kPa, PO2 ≈ 7-8 kPa

Baixar (72KB)
Metadados
9. Fig. 4. Variation of the initial rate of product formation during oxidative carbmethoxylation of acetylene using PdBr2-LiBr-PcCo-AN-MeOH catalytic system, depending on αMeOH in the AN-MeOH solution. Conditions: CPdBr2 = 0.03 M, CLiBr = 0.1 M, CPcCo = 0.03 M, reactor gas composition: PCO ≈ 47-50 kPa, PC2H2 ≈ 11-15 kPa, PO2 ≈ 4-7 kPa

Baixar (90KB)
Metadados
10. Fig. 5. Product accumulation and gDMF/gDMM ratio during oxidative carbmethoxylation of acetylene using PdBr2-LiBr-PcCo-AN-MeOH catalytic system. Conditions: CPdBr2 = 0.03 M, CLiBr = 0.1 M, CPcCo = 0.03 M, αMeOH = 0.13, reactor gas composition: PCO ≈ 59-62 kPa, PC2H2 ≈ 1-4 kPa, PO2 ≈ 6.5 kPa

Baixar (97KB)
Metadados
11. Fig. 6. Comparison of product concentrations obtained during oxidative carbmethoxylation of acetylene in experiments with and without MA addition. Conditions: system PdBr2-LiBr-PcCo-AN-MeOH, CPdBr2 = 0.03 M, CLiBr = 0.1 M, CPcCo = 0.03 M, αMeOH = 0.13, gas composition in the reactor: PCO ≈ 47-51 kPa, PC2H2 ≈ 11-15 kPa, PO2 ≈ 4-7 kPa

Baixar (139KB)
Metadados
12. Fig. 4

Baixar (12KB)
Metadados
13. Fig. 5

Baixar (17KB)
Metadados
14. Scheme 2. Mechanism of formation of DMM, DMF and DMC in the process of oxidative carbmethoxylation of acetylene

Baixar (223KB)
Metadados