Lab 4: T h i n Layer Chromatography Jeffrey D i x o n 2/17/14 Partner: Cedrian H o d g e

Purpose: Utilize thin layer chromatography to analyze and calculate the R f values o f over-the-counter drugs. Introduction: C h r o m a t o g r a p h y is a m e t h o d o f separating a m i x t u r e into its c o m p o n e n t s . T L C is p e r f o r m e d o n a sheet o f glass, plastic, o r m e t a l that i s coated w i t h a t h i n l a y e r o f adsorbent m a t e r i a l s u c h as s i l i c a gel or a l u m i n a . T L C i n v o l v e s t w o phases. A stationary phase i s the t h i n l a y e r o f adsorbent and the m o b i l e phase is the solvent (eluent) w h i c h travels u p the plate. T h e m o b i l e phase travels u p the T L C plate v i a c a p i l l a r y a c t i o n . I f the e l u e n t i s p o l a r i t w i l l adsorb t o the plate w h i l e the rest o f the solvent travels u p the plate.

Table of Reagents: Mixture 1 2 3 Reagent Aspirin Acetaminophen Molar Mass 180.157 g/mol 151.163 g/mol 216.23 g/mol 194.19 g/mol 206.29 g/mol Density 1.40 g / c m ^ 1.263 g/cm^ 1.2g/cm3 1.23 g / c m ^ 1.03 g / c m ^ Boiling Point 1 4 0 C N/A 408.8C 178C 157C Melting Point 1 3 6 C 1 6 9 C 250C 238C 76C

(S)-(+)-Naproxen sodium 4 Caffeine (S)-(+)-Ibuprofen 5 Procedure:

T w o t a b l e t s o f e a c h o f t h e five O T C d r u g s w e r e c r u s h e d u s i n g a m o r t a r a n d p e s t l e . T h e d r u g s w e r e g r i n d e d w i t h f o u r m L o f m e t h a n o l . T h e s u s p e n s i o n w a s t h e n g r a v i t y filtered t h r o u g h a p i e c e o f filter p a p e r . T h e five s u s p e n s i o n s w e r e s p o t t e d o n t r e e T L C p l a t e s . T h r e e t a n k s w e r e filled

w i t h hexane, ethyl acetate, and a m i x t u r e 25:75 e t h y l acetate-hexane m i x t u r e . T h e T L C plates were placed i n these tanks. T h e tanks w e r e then covered to prevent the solvent f r o m evaporating

f r o m the T L C plate. A f t e r the solvent reaches the solvent line, the plates w e r e r e m o v e d f r o m the tank and a l l o w e d to dry. T h e separated spots w e r e then v i s u a l i z e d w i t h a U V light. Results: 25:75 Ethyl Acetate/Hexane mixture d s = 4.7cm Mixture dn 1 Ocm 2 1.4cm 1.9cm 3 4 1.7cm 3.3cm 5 Ethyl Acetate d s = 4.5cm Mixture 1 2 3 4 5 Hexane
dn Rf Rf

0 0.29 0.40 0.36 0.70

2.3cm 3.4cm 3.8cm 0.9cm 3.7cm

0.51 0.76 0.84 0.20 0.82

A l l polar (stayed as a dot o n the baseline). R t = 0 Calculations:

_
'

A _ ^ ^ L i

^vo1^n

'i^asd'^AC t f C A i e l l e d

bi^so'LA-^t

(i^^\<xr\ct

^"la^^ b a s t u A t

t Y a u c l l e f J - loi.;j

iolv/^nf

4.1cm

Discussion: T h e ds w a s d i f f i c u l t t o m e a s u r e because the base l i n e w a s slanted. T h e R f v a l u e relates the distance the substance t r a v e l l e d o v e r the distance the s o l v e n t travelled. I t is based o n polarity. The larger an R r value, the further the substance travelled u p the plate. I n polar solvents, polar

eluents w i l l not travel far since they w i l l adsorb to the plate. T h e spots d i d n o t travel i n the hexane. T h e six m i x t u r e s are i n s o l u b l e i n h e x a n e because it is a n o n p o l a r m o l e c u l e . L i k e dissolves l i k e w h i c h is reflected i n the R f v a l u e s o b t a i n e d f r o m the e t h y l acetate/hexane m i x t u r e and e t h y l acetate solvent. Separation w a s observed i n these solvents. I b u p r o f e n and n a p r o x e n s o d i u m had r e l a t i v e l y h i g h Rfvalues w h i c h m e a n s t h e y h a d the m o s t separation and they are polar. Conclusion: O f the three s o l v e n t s , h e x a n e w a s n o t e f f e c t i v e f o r e l u e n t separation. T h e e t h y l acetate's ester group accounted for the m o l e c u l e ' s polarity. T h e polarity aided i n the m o v e m e n t o f substance up along the T L C plate. E t h y l acetate w a s the m o s t effective s o l v e n t f o r R f c a l c u l a t i o n f o l l o w e d b y the e t h y l acetate/hexane m i x t u r e .