«Proceedings of Gubkin University»

CATALYTIC SYNTHESIS OF CARBOXYLIC ACIDS BY CARBONYLATION OF OLEFINS AND ALCOHOLS IN IONIC LIQUID MEDIA

UDC: 546.262.3:542.971.2
DOI: -

Authors:

¹ Zelinsky Institute of organic chemistry
² Gubkin Russian State University of Oil and Gas

Keywords: homogeneous catalysis, carbon monoxide, carbonylation, olefins, alcohols, carboxylic acids, palladium

Annotation:

Catalytic carbonylation of ethylene, higher olefins and alcohols produces carbox-ylic acid. We have shown that a comfortable media for these reactions are ionic liquids. Their advantage over standard solvents is the ability to dissolve the palladium catalyst not containing organophosphine ligands. This achieves a substantial simplification and cost reduction of the catalyst system. Also shown is that after extraction of the reaction products, the catalyst remains dissolved in the ionic liquid and can be used repeatedly without loss of activity.

Bibliography:

1. Лапидус А. Л., Пирожков С. Д. Каталитический синтез органических соединений, карбонилирование непредельных углеводородов и спиртов//Успехи химии. - 1989. - Т. 58. - № 2. -С. 197-233.
2. Gordon C.M. New developments in catalysis using ionic liquids//Applied Catalysis A: General. - 2001. V. 222. - P. 101-117.
3. Olivier-Bourbigou H., Magna L. Ionic liquids: perspectives for organic and catalytic reactions//;. Mol. Catal. A: Chem. - 2002. - V. 182-183. - P. 419-437.
4. Wasserscheid P., Welton T. (Eds.) Ionic Liquids in Synthesis. Wiley-VCH, Weinheim, 2002. - 355 p.
5. Welton T. Ionic liquids in catalysis//Coord. Chem. Rev. - 2004. - V. 248. - P. 2459-2477.
6. Zhang Z.C. Catalysis in Ionic Liquids//Adv. Catal. - 2006. - V. 49. - P. 153-237.
7. Liu S., Xiao J. Toward green catalytic synthesis - Transition metal-catalyzed reactions in non-conventional media//J. Mol. Catal. A: Chemical. - 2007. - V. 270. - P. 1-43.
8. Ranke J., Stolte S., Stormann R., Arning J., Jastorff B. Design of Sustainable Chemical Prod-uctssThe Example of Ionic Liquids//Chem. Rev. - 2007. - V. 107. - P. 2183-2206.
9. Лапидус А.Л., Елисеев О.Л., Стёпин Н.Н., Бондаренко Т.Н. Карбоксилирование стирола в системе N(C4H9)4Br/гептан//Известия Академии Наук, Сер. Химия. - 2004. - № 11. -C. 2458-2461.
10. Елисеев О.Л., Стёпин Н.Н., Бондаренко Т.Н., Лапидус А.Л. Бесфосфиновая каталитическая система для карбоксилирования олефинов оксидом углерода//ДАН. - 2005. - Т. 401. -№ 4 - С. 486-488.
11. Lapidus A., Eliseev O., Bondarenko T., Stepin N. Palladium catalysed hydroxycarbonylation of 1-phenylethanol in molten salt media//J. Mol. Catal. A: Chemical. - 2006. - V. 252. - P. 245-251.
12. Zim D., de Souza R.F., Dupont J., Monteiro A.L. Regioselective synthesis of 2-arylpropionic esters by palladium-catalyzed hydroesterification of styrene derivatives in molten salt media//Tetra-hedron Lett. - 1998. - V. 39. - P. 7071-7074.
13. Jang E.J., Lee K.H., Lee J.S., Kim Y.G. Regioselective synthesis of ibuprofen via the palladium complex catalyzed hydrocarboxylation of 1-(4-isobutylphenyl) ethanol//J. Mol. Catal. A: Chemical. - 1999. - V. 138. - P. 25-36.
14. Parshall G.W., Ittel S.D. Homogeneous Catalysis., 2nd Edition. Wiley, New York, 1992. -P. 100.
15. Lapidus A.L., Eliseev O.L., Bondarenko T.N., Chau N.H. Hydroxy- and Alkoxycarbo-nylation of Ethylene in Molten Salt Medium//DGMK/SCI-Conference «Production and Use of Light Olefins», September 28-30, 2009. Dresden, Germany. Proceedings, р. 225-231.
16. Eliseev O.L., Bondarenko T.N., Stepin N.N., Lapidus A.L. Carbonylation of alcohols in the Pd(OAc)2/TsOH/molten salt system//Mendeleev Commun. - 2006. - V. 16. - P. 107-109.
17. Lapidus A.L., Eliseev O.L., Bondarenko T.N., Chau N.H. Hydroxycarbonylation of benzylic derivatives in ionic liquid media//DGMK/SCI-Conference «Future Feedstocks for Fuels and Chemicals». September 29 - October 1, 2008. Berlin, Germany. Proceedings, p. 249-256.