Organic solvent nanofiltration in asymmetric hydrogenation: Enhancement of enantioselectivity and catalyst stability by ionic liquids

Chemical Communications

Volumn , Issue 19, 2006, Pages 2063-2065

  Wong, Hau To ^a   See Toh, Yoong Hsiang ^a   Ferreira, Frederico Castelo ^a   Crook, Robert ^b,c   Livingston, Andrew G ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c Sittingbourne Research Centre   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IONIC LIQUID; NAPHTHYL GROUP; ORGANIC SOLVENT; PHOSPHONIUM DERIVATIVE; RUTHENIUM; TRIHEXYL(TETRADECYL)PHOSPHONIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; ENANTIOSELECTIVITY; HYDROGENATION; NANOFILTRATION; REACTION TIME; RECYCLING;

EID: 33646542672     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b602184k     Document Type: Article

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12. The single-phase reactions were carried out in a stainless steel reactor (METcell, www.membrane-extraction-technology.com); 8.0 g (50 mM) of DMI and 8.0 g of IL were dissolved in 80 ml of MeOH and degassed via the Schlenk technique with Ar before charging into the reactor. 6.7 mg (0.0084 mM) of Ru-BINAP (CAS: 132071-87-5) was then added to the reactor and heated to 35°C. After each cycle, 80 ml of permeate was taken (in approximately 16 min) and fresh feed was added to make up a feed solution of 100 ml with fresh substrate. The membrane was 'washed' with the reaction solvent between each run
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22. ™ is a trademark of W. R. Grace and Co. Molecular weight cut-off is defined by the molecular weight for which 90% rejection of the solute is achieved by the membrane
23. S/C: Substrate to catalyst ratio: S/C = mol substrate/mol catalyst
24. D. Nair H. T. Wong S. J. Han I. F. J. Vankelecom L. S. White A. T. Boam A. G. Livingston Org. Process Res. Dev. 2006
25. i,rxn = mol of DMMS in permeate/mol of DMI fed to reaction × 100; ee is defined by the equation ([S] - [R])/([S] + [R]) and was determined using a Chiralcel OD-H column with 90:10 (hexane-IPA) as the mobile phase
26. TON is defined by the following equation: TON = Total mol DMMS over all cycles/mol catalyst added
27. R,i is the concentration of i in the retentate
28. Catalyst and IL rejections were determined by first digesting samples in a MARS microwave digester followed by measuring the Ru and P concentrations via ICP-OES