Organic Chemistry Laboratory-First Term A.Y. 2016-2017
Extraction o Caeine rom Tea Lea!es Tana" #emarie$ %." Tig&$o" Ce$ina Ysabe$ %." ' Yon(on" Ange$a Cath$een )*.+ #e,artment o io$ogica$ )ciences" ni!ersity o )anto Tomas" /ani$a" *hi$i,,ines #ate )&bmitte )e,tember 20" 2016 Abstract
This ex,eriment ea$s ith the extraction o caeine rom tea$ea!es. The sam,$e that as Li,ton tea. The ,rocess in!o$!e re,eate extraction ,rocess an ,&riication !ia to methos" s&b$imation an crysta$$i(ation. To test the ,&rity o the caeine" it me$ting ,oint m&st be irst etermine. The ,ercent yie$e o caeine as 1.034 hi$e the eight o the extracte caeine as 0.1171 grams. 5eyors 5eyors extracte extracte caeine caeine rom tea$ea!es" s&b$imati s&b$imation on an crysta$$i(a crysta$$i(ation" tion" me$ting ,oint" ,ercent yie$. Introduction:
Caeine" 1""7 trimethy$xanthine" is an a$8a$oi stim&$ant common$y o&n in tea" coee an co$a be!erages. 9t &s&a$$y tastes bitter an has a stim&$ating eect to the brain an centra$ ner!o&s system" he$,ing h&mans to be ,hysio$ogica$$y acti!e. )e!era$ actors s&ch as !ariety o coee bean or tea$ea" $ocation o the ,$ant:s groth an metho o breing may aect the amo&nt o caeine in coee or tea. ;1< e$onging to the a$8a$oi c$ass o com,o&ns" caeine are nitrogeno&s basic com,o&ns an can be consiere to be constr&cte rom the ,&rine ring system. ;2<
Fig&re 1. Leis )tr&ct&res o ,&rine an caeine. =etrie!e rom htt,>>em,$oyees.oneonta.e&>8na htt,>>em,$oyees.oneonta.e&>8na&erbr>chem226 &erbr>chem226
9so$ation o caeine may be one thro&gh extraction herein the sam,$e is istrib&te beteen to or more ,hases. ;< Extraction is a metho &se or se,arating an organic com,o&n rom a mixt&re. 9n this techni?&e" one or more com,o&ns o&$ be isso$!e se$ecti!e$y into a ,artic&$ar so$!ent. The extract o&$ be the so$&tion o the isso$!e com,o&ns. ;@< A$tho&gh" tea $ea!es contain another com,onent that may be co-extracte s&ch as tannins" the ierentia$ so$&bi$ity o caeine an tannins in ich$oromethane CB2C$2 a$$os the se,aration o the to &ring extraction. To &rther &rther ,&riy a nat&ra$ ,ro&ct an iso$ate it rom &nesire com,o&ns" the s&b$imation metho may be &se. 9n this ,rocess" the ,ro&ct i$$ &nergo a irect ,hase change rom so$i to !a,or itho&t ,assing the $i?&i state. ;D< This ex,eriment aims to iso$ate" ,&riy an characteri(e caeine rom tea $ea!es" an etermine the ,ercent yie$ o caeine in the sam,$e. Results and Discussion Table Table 1. Tabulation Tabulation of experimental results Brand of Tea
Li,ton Ye$$o Labe$
Weight of Tea Leaes
10.3@6 grams
!olume of " #$ used
1D0 mL
%olor of a&ueous tea extract
#ar8 bron
!olume !olume of dichloromethane used
60 mL
!olume !olume of '( )a$" used
20 mL
Amount of anh*rdrous )a #+$,
1 s,at&$a
%olor of dichloromethane extract
co$or$ess
Weight of empt* eaporating dish
11D.@131 grams
Weight of eaporating dish and extracted caffeine
11D.DD2 grams
Weight of extracted caffeine
0.1171 grams
-ield of extracted caffeine
1.03
%olor appearance of extracted caffeine
hite so$i
9n the ex,eri ex,erimen ment" t" caei caeine ne is extrac extracte te rom rom Li,ton Li,ton Ye$$o $$o Labe$ Labe$ tea $ea!es $ea!es ater ater s&bGecting s&bGecting it to boi$ing" boi$ing" extraction" extraction" an s&b$imatio s&b$imation. n. The com,o&n" com,o&n" an a$8a$oi" a$8a$oi" is ,o$ar an is so$&b$e in boi$ing ater at 666 mg>m$ ;6<. Ater coo$ing the tea extract" it as transerre to a se,aratory &nne$ or extraction. 9n this" ich$oromethane or methy$ene ch$orie CB2C$2 as ae. CB2C$2 is a !o$ati$e $i?&i" ith a ensity o 1. g>cm. This $i?&i is a$so ,o$ar ith the ,resence o to more e$ectronegati!e ch$orines against to h yrogens" creating a i,o$e moment Fig&re 2. Caeine" a$tho&gh high$y so$&b$e in ater at high tem,erat&res" is more so$&b$e in CB2C$2 at room tem,erat&re. The coo$ing o the tea extract beore the extraction as one &e to this. #ensities o $i?&is are at or8 in the extraction set&," ith CB 2C$2:s 1.g>cm higher than ater:s ensity o 1.00g>cm. Th&s" caeine i$$ be isso$!e isso$!e in the $oer CB2C$2 $ayer Fig&re @" $ea!ing the &,,er ater $ayer ith $ess an $ess caeine as the three 20 mL extractions are inishe. A$tho&gh caeine is the s&bstance o interest in this ex,eriment" tea $ea!es a$so contain a com,o&n ca$$e ga$$ic aci" a ,heno$ic aci. This com,o&n is better 8non or its antioxiant ,ro,erties" ith the ,otentia$ to initiate a,o,tosis in ce$$s ;7< an ,romote cancer cancer ce$$ ce$$ eath eath ;3<. ;3<. 9n the extracti extraction on set&," set&," both both caeine an ga$$ic aci are ,resent in the $oer $ayer
Fig&re 2. )tereochemica$ raing o CB 2C$2.
to be extracte. #&e to this" a ashing ste, in!o$!ing the the ai aiti tion on o 6/ HaOB HaOB so$& so$&ti tion on is one one.. The The a$8a$ine so$&tion" hen ae to the CB2C$2 $ayer" i$$ react ith the ga$$ic aci to orm ater" carbon ioxie" an a ga$$ic aci sa$t Fig&re .
Fig&re . =eaction beteen ga$$ic aci an HaOB.
hen the ashing as con&cte in the se,aratory &nne$" b&bb$es reai$y e!o$!e Fig&re @" hinting the ,resence o carbon ioxie gas. The aition o the soi&m ion increases the ,o$arity o ga$$ic aci" increasing its so$&bi$ity in ater. 9n theory" theory" the ga$$ic aci in the orm o its sa$t m&st no be in the &,,er ater $ayer" an the $oer CB2C$2 $ayer m&st contain the caeine to be extracte.
Fig&re @. Act&a$ extraction set &, ith $abe$e ,arts. Extraction o caeine ith CB 2C$2 $et an ashing ith HaOB" i$$&strating i$$&strating b&bb$e ormation right. right.
Ater rying the s&bstance thro&gh aing anhyro&s Ha2)O@" the ,ro&ct as s&b$ime an eighe. The eight o the cr&e caeine obtaine rom the ex,eriment as 0.1171 grams" $eaing to a ,ercent yie$ o 1.034 Tab$e 1. This as com,&te by i!iing the ex,erimenta$ yie$ o cr&e caeine by the tota$ grams o tea $ea!es &se" hich is 10.3@6 grams. Th&s" the ex,erimenta$ res&$ts sho that a tea bag o Li,ton Ye$$o Ye$$o Labe$ b$ac8 tea has a,,roximate$y
2.@2 mi$$igrams o cr&e caeine. 9ea$$y" 3 $&i o&nces o Li,ton Ye$$o Ye$$o Labe$ b$ac8 tea a,,roximate$y one tea bag has DD mi$$igrams o caeine. ;< +ample %omputations
weight weight extcd . caffein caffeinee = wt .of eva evap p .dish .dish ∧extcd extcd . caffein caffeinee − wt . of eva evap p . dish ish weight extcd . caffeine caffeine
=
yield of caffeine =
yield of caffeine
=
115.5352 g − 115 115 .4181
g
weig weight ht extc extcd d . caff caffei eine ne
=
0.1171 g
weight weight exctd . caffein caffeinee × 100 weight weight of tealeaves 0.1171 g extc extcd d . caffe caffeine ine 10.8469 gtealeaves
× 100
¿ 0.108 × 100
yield of caffeine
=
1.08
caffeine caffeine per tea bag =
caffeine caffeine per tea bag =
weight weight extcd . caffeine caffeine number of teabags extcd d . caffe caffeine ine 0.1171 g extc 5 tea bags bags
caffeine caffeine per tea bag = 0.02342 g per bag ≈ 23.42 mg per per bag bag
The $oer yie$ o 2.@2 mi$$igrams com,are to the iea$ DD mi$$igrams can be attrib&te to some errors in the &ration o the ex,eriment. 9n the in&sion set&," the tea $ea!es ere bree or i!e min&tes &nti$ the extract as ar8 bron. A ar8er co$or co&$ ha!e been achie!e i the teas ere in&se or a $onger ,erio o time. A ar8er co$or signiies a stronger caeine extract" th&s" a $arger yie$. An increase in the tem,erat&re contro$$e by the &nsen $ame co&$ a$so ,otentia$$y increase caeine yie$" since the $atter:s so$&bi$ity in boi$ing ater is
signiicant$y high. #&e to the ex,eriment:s restrictions" the ,&rity o the obtaine cr&e caeine as not teste. /xperimental
Fi!e Li,ton tea bags ere &se in this ex,eriment. The combine eights o the tea $ea!es ere recore an ret&rne in the bags an ere sec&re ith a sta,$e ire. The teabags ere boi$e in 100 mL ater or D min&tes. The sie o the $as8 as coo$e in r&nning ater or 2 min&tes an an ice c&be as mixe ith the tea extract to coo$ it to room tem,erat&re. The tea extract as transerre in a se,aratory &nne$ containing 20 mL o CB 2C$2 #icho$oromethane. The sto,coc8 o the se,aratory &nne$ as o,ene to re$ease the ,ress&re constant$y. The $oer $ayer as raine into a c$ean $as8 an the extraction as re,eate tice. The remaine bron $ayer as iscare an the se,aratory &nne$ as c$eane. The CB2C$2 $ayer as then ret&rne to the se,aratory &nne$ an 20 mL o 6/ HaOB as ae. The HaOB $ayer then as iscare. The CB2C$2 $ayer as raine into a c$ean" ry 12D mL Er$enmeyer $as8 containing ha$ s,at&$a o anhyro&s Ha2)O@ an as sir$e &nti$ the Ha2)O@ sett$e. The mixt&re as ecante in a ,reeighe e!a,orating ish. The e!a,orating ish as ,$ace on to, o a 2D0 mL bea8er to a$$o it to e!a,orate &nti$ & nti$ the hite resi&e as obtaine. The hite resi&e eighe an the ,ercent yie$ as ca$c&$ate. The extracte caeine as then transerre into an em,ty ,reeighe !ia$.
References
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