Racemic mixture separation
-
Upload
madhura-chincholi -
Category
Science
-
view
46 -
download
2
Transcript of Racemic mixture separation
![Page 1: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/1.jpg)
RACEMIC MIXTURE SEPARATION(MENTHOL)
Madhura N. Chincholi
14CHE2032
1
![Page 2: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/2.jpg)
RACEMIC MIXTURE?
A solution in which both enantiomers of a compound are present in equal amounts
Racemic mixtures can be symbolized by a (d/l)- or (+/-)- prefix in front of the substance's name.
The separation of a racemic mixture in to dextro and laevo components is termed resolution.
Due to identical physical properties their separation cannot be effected by simple physical methods.
Usual methods used for resolving racemic compounds are Mechanical Separation, Biochemical separation and by means of salt formation. 2
![Page 3: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/3.jpg)
RESOLUTION BY CRYSTALLIZATION
The racemic compound is reacted with a resolving agent
So the mixture contains three chiral compounds: the two enantiomers and another chiral compound.
At this time the more stable diastereoisomer crystallizes and it can be separated from the
non racemic enantiomeric mixture by several methods.
3
![Page 4: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/4.jpg)
4
The essential processes of enantiomeric separation starting from the racemic compound
![Page 5: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/5.jpg)
MENTHOL
5
(+)-Menthol (-)- Menthol
IUPAC name : (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
•Menthol has local anesthetic and counterirritant qualities.•Widely used to relieve minor throat irritation.
![Page 6: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/6.jpg)
RESOLUTION OF RACEMIC MENTHOL(MEN)
1. Crystallization without any solvent The mixture of resolving agent(RA) and
racemic compound should be warmed until it melted
Then it should be cooled while one of the diastereoisomers crystallizes from the melt.
RA : O,O’-dibenzoyl-(R,R)-tartaric acid ((R,R)-DBTA).
The crystalline molecular complex (diastereoisomer) contains the (1R,2S,5R)-menthol (the Lmenthol(L-MEN))
While the remained melt is enriched in the other enantiomer.
6
![Page 7: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/7.jpg)
7
Crystallization without any solvent
![Page 8: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/8.jpg)
2. Crystallization with solvent
RA : (R,R)-DBTA. Solvent : Hexane The crystalline molecular complex
(diastereoisomer) contains the (1R,2S,5R)-menthol (the Lmenthol(L-MEN))
While the other enantiomer reamined in the solvent.
8
![Page 9: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/9.jpg)
Crystallization with solvent (hexane)
9
![Page 10: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/10.jpg)
REFERENCE
E. Pálovics, F. Faigl and E. Fogassy, "Separation of the Mixtures of Chiral Compounds by Crystallization", Journal of Advances in Crystallization Processes, Page 1-37.
10
![Page 11: Racemic mixture separation](https://reader035.fdocuments.net/reader035/viewer/2022071902/55c356f8bb61eb0a7e8b46b7/html5/thumbnails/11.jpg)
THANK YOU!
11