Scalable Enantioseparation of Amino Acid Derivatives Using Continuous Liquid-Liquid Extraction in a Cascade of Centrifugal Contactor Separators

被引:68
作者
Schuur, Boelo [2 ]
Hallet, Andrew J. [1 ]
Winkelman, Jozef G. M. [2 ]
de Vries, Johannes G. [1 ,3 ]
Heeres, Hero J. [2 ]
机构
[1] DSM Pharmaceut Prod, Innovat Synth & Catalysis, NL-6160 MD Geleen, Netherlands
[2] Univ Groningen, Dept Chem Engn, NL-9747 AG Groningen, Netherlands
[3] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
关键词
CHIRAL SEPARATION; ENANTIOSELECTIVE EXTRACTION; REACTIVE EXTRACTION; OPTICAL RESOLUTION; CO-EXTRACTANTS; ENANTIOMERS; CHROMATOGRAPHY; EQUILIBRIUM; ALCOHOLS; RECOGNITION;
D O I
10.1021/op900152e
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Using a cascade of six centrifugal contactor separators in a countercurrent liquid-liquid extraction mode allowed the separation of one of the enantiomers of 3,5-dinitrobenzoyl-leucine in 55% yield and 98% ee using a catalytic amount of a chiral host compound based on a cinchona alkaloid, This method allows the preparation of kilograms of enantiopure material in table-top-sized equipment that can be operated in a fume cupboard. The methodology can be easily scaled up to ton amounts as large-volume centrifugal contactor separators are commercially available as well.
引用
收藏
页码:911 / 914
页数:4
相关论文
共 38 条
[21]   ENANTIOSELECTIVE EXTRACTION OF DI-O-BENZOYLTARTRATE ANION BY ION-PAIR EXTRACTANT HAVING BINAPHTHYL-UNIT [J].
OHKI, A ;
MIYASHITA, R ;
NAKA, K ;
MAEDA, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (09) :2714-2719
[22]   Equilibrium and kinetic studies of the enantioselective complexation of (D/L)-phenylalanine with copper (II) N-decyl-(L)-hydroxyproline [J].
Pickering, PJ ;
Chaudhuri, JB .
CHEMICAL ENGINEERING SCIENCE, 1997, 52 (03) :377-386
[23]   A practical approach to the resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction with a lipophilic chiral salen-cobalt(III) complex [J].
Reeve, TB ;
Cros, JP ;
Gennari, C ;
Piarulli, U ;
de Vries, JG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) :2449-2453
[24]   Chiral business [J].
Rouhi, AM .
CHEMICAL & ENGINEERING NEWS, 2003, 81 (18) :45-+
[25]   Continuous chiral separation of amino acid derivatives by enantioselective liquid-liquid extraction in centrifugal contactor separators [J].
Schuur, Boelo ;
Floure, Joelle ;
Hallett, Andrew J. ;
Winkelman, Jozef G. M. ;
de Vries, Johannes G. ;
Heeres, Hero J. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (05) :950-955
[26]   Equilibrium Studies on Enantioselective Liquid-Liquid Amino Acid Extraction Using a Cinchona Alkaloid Extractant [J].
Schuur, Boelo ;
Winkelman, Jozef G. M. ;
Heeres, Hero J. .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2008, 47 (24) :10027-10033
[27]   Influence of process parameters on extraction equilibria for the chiral separation of amines and amino-alcohols with a chiral crown ether [J].
Steensma, M ;
Kuipers, NJ ;
de Haan, AB ;
Kwant, G .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2006, 81 (04) :588-597
[28]   Identification of enantioselective extractants for chiral separation of amines and aminoalcohols [J].
Steensma, M ;
Kuipers, NJM ;
De Haan, AB ;
Kwant, G .
CHIRALITY, 2006, 18 (05) :314-328
[29]   Analysis and optimization of enantioselective extraction in a multi-product environment with a multistage equilibrium model [J].
Steensma, Maartje ;
Kuipers, Norbert J. M. ;
de Haan, Andr B. ;
Kwant, Gerard .
CHEMICAL ENGINEERING AND PROCESSING-PROCESS INTENSIFICATION, 2007, 46 (10) :996-1005
[30]   Modelling and experimental evaluation of reaction kinetics in reactive extraction for chiral separation of amines, amino acids and amino-alcohols [J].
Steensma, Maartje ;
Kuipers, Norbert J. M. ;
de Haan, Andre B. ;
Kwant, Gerard .
CHEMICAL ENGINEERING SCIENCE, 2007, 62 (05) :1395-1407