7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Purpose:(e purpose of tis experiment is to extract an) iso*ate caffeine from an o+er,te counter stimu*ant
)ru- +ia *iui),*iui) extraction recr!sta**iation an) +acuum fi*tration of te )esire) compoun).
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
"pproac:ei- te i+arin ta3*ets an) So)ium car3onate wit te e*ectronic 3a*ance to )etermine te mass.
Prepare eat an) )ecant i+arin an) So)ium Car3onate so*ution. 4se te *iui),*iui) extraction
meto) wit )ic*orometane to extract an) iso*ate caffeine from te aueous i+arin/so)ium car3onate
so*ution. ")) "n!)rous so)ium su*fate to te extracte) caffeine so*ution. ")) co*) acetone an)
petro*eum eter to recr!sta**ie te )rie) samp*e. Dr! furter +ia +acuum fi*tration. "ir,)r! for one
wee. Determine te mass of te purifie) caffeine samp*e 3! wei-in-. Ca*cu*ate te percent reco+er! fo
te purification. 4se te %e*(emp apparatus to )etermine te me*tin- point an) assess te purit! of te
fina* samp*e.
6eferences(ext
• S*a!)en S. Sta*ic . 6ot 6 201' r-anic Cemistr! 8a3orator! %anua* 2n) E)ition:
Pearson Custom Pu3*isin-: pp. '7,'9
• Pa+ia D.8. 8ampman .%. Kri .S. En-e* ..6. 2011 ;ntro)uction to r-anic 8a3orator!
(ecniues " Sma** Sca*e "pproac %4 E)ition Cem &15/&1< Cen-a-e 8earnin-: pp. 2' 7&,
<'
e3 Site 468
• Dr Scornic=s e3site: ttp:/mason.-mu.e)u/>?scorni/caffeine
• $@ce*=s 6u*e: ttp://-oo.-*/rA;28
4nnown or S!ntesie) Compoun)
• &7,Di!)ro,1&7,trimet!*,1 H ,purine,2B,)ione Caffeine C"S No. 5<,0<,2 C6C $an)3oo of
Cemistr! P!sics <'t E)ition 8i)e D.6. E)itor,in,cief 200&,200' C6C Press #1B92 p. &,
90.
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # 1 %ass 6ea-ents 6esu*ts 4n No.
%ateria*s Euipment%ass i+arin
%ass wei- 3oat &.2<5-
%ass 3oat F ta3*ets '.1<0-
%ass ta3*ets '.1<0 , &.2<5 0.<95-
Caffeine/pi**0.200-
G Caffeine/pi** H.200/0.<95/2Ix100 ''.7 G
%ass Na2C&
%ass wei- 3oat &.2B5-
%ass 3oat F Na2C& 11.51B-
%ass Na2C& 11.B15 J &.2B5 <.251-
• 2 i+arin
ta3*ets
• <- Sodium
Carbonate Na2C&
• 2 ei- 3oats
• E*ectroni
c 3a*ance
L0.001-
• Ca*cu*at
or
Desc:
• (are te 3a*ance.
• 6ecor) te mass of te empt! 3oat
to te nearest 0.001-.
• 6ecor) te mass of te ta3*ets in te
wei- 3oat to te precision *imit of te
3a*ance.
• Ca*cu*ate te G acti+e in-re)ient
3ase) on te -rams of caffeine per pi**.
• 6epeat steps 1,& usin- <- of
Na2C& an) recor) mass to te nearest0.001-.
Euation Setup:
%ass of i+arin ta3*ets:
%ass ta3*ets in 3oat - J mass empt! 3oat -
M mass ta3*ets -
Percent caffeine per pi**:
HCaffeine per pi** - / H%ass of 2 ta3*ets - /
2II x 100
%ass So)ium Car3onate
%ass samp*e in 3oat - J mass empt! 3oat -
M mass samp*e -
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # 2 Prepare So*ution 6esu*ts
%ateria*s Euipment3ser+ations:
• i+arin ta3*et was eas! to crus.
6esu*te) in a fine wite pow)er.
• Na2C& was te same co*or as te +i+arin
3ut was a) *ar-er cr!sta*s an) more -ranu*ar
appearance.
• (e co*or of te so*ution can-e) from
co*or*ess to !e**ow as it approace) a 3oi*.
• 2 i+arin ta3*ets
• B0m8 D.;. $2
• <- Sodium
Carbonate Na2C&
• (ef*on 3oi*in-
cip
• *ass woo*
• %ortar
pest*e
• 2 150m8
eaers
• Spatu*a
• ra)uate)
c!*in)er• $ot p*ate
• *ass
funne*
• C*a!
trian-*es
• ;ron rin-
• 6in- stan)
• 125m8
separator! funne*
Desc:
• Pu*+erie te i+arin usin- te mortar
an) pesta* into a uniform pow)er.
• (ransfer te pow)er to a c*ean )r!
150m8 3eaer
• 4sin- a -ra)uate) c!*in)er measure
B0m8 of D.;. $2
• ")) to te 3eaer.
• ")) pre,wei-e) <- Na2C& to te
3eaer.
• ")) (ef*on 3oi*in- cip.• $eat so*ution on a otp*ate. oi* for
2min.
• 6emo+e 3eaer from eat. "**ow mixture
to sett*e.
Euation Setup:
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # & 8iui),*iui) Extraction 6esu*ts
%ateria*s Euipment3ser+ations:
• 8a!ers of separation witin te so*ution
3ecame apparent as te so*ution sett*e) an)
coo*e).
• 4pon te a))ition dichloromethane an)
-ent*e a-itation a co*or*ess *a!er of *iui) te
dichloromethane/ or-anic *a!er accumu*ate) at
te 3ase of te sepearator! funne* an) a c*ou)!
!e**owis *a!er containin- wite se)iments
inso*u3*e aueous *a!er accumu*ate) a3o+e it.
• i+arin Na2C&
So*ution
• 2' m8
Dichloromethane
• ra)uate)
c!*in)er
• 1 150m8
eaer
• *ass
funne*
• C*a!
trian-*e
• ;ron rin-
• 6in- stan)
• 125m8
separator! funne*
an) stopper
Desc:
• Pac te wa**s of a sma** -*ass funne*
wit a sma** amount of -*ass woo*.
• "ssem3*e seprator! funne* apparatus.
• Decant samp*e so*ution into te seprator!
funne*.
• 6emo+e te -*ass funne*.
• Sea* te seprator! funne* wit te -*ass
stopper.
• Coo* so*ution to room temperature.
• ;n a -ra)uate) c!*in)er measure < m8
of Dichloromethane.
• ")) to mixture in seprator! funne*.
• Stopper in+ert an) swir* te seprator!
funne* -ent*! for 10,15 secon)s.
• it te funne* in+erte) open te
stopcoc to re*ease an! 3ui*t up pressure.
• C*ose stopcoc.
• 6epeat swir*in- in+ertin- an) +entin- &
times.
• 6ep*ace separator! funne* in rin- stan).
"**ow to sett*e.
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
• ;n a c*ean )r! 150m8 3eaer co**ect tec*ear or-anic *a!er of f*ui) 3! openin- te
stopcoc
• 6epeat extraction 2 times wit 2 more <
m8 portions of Dichloromethane.
Euation Setup:
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # ' Dr!in- , "n!)rous So)ium Su*fate 6esu*ts
%ateria*s Euipment3ser+ations:
• (e cr!sta*s of Anhydrous Sodium Sulfat
were *ar-e wite an) inso*u3*e in te so*ution.
• Extracte)
Dichloromethane
so*ution
• Anhydrous
Sodium Sufate
• 50m8
3eaer
• 150m8
3eaer
Desc:
• ")) Anhydrous Sodium Sulfate toextracte) samp*e so*ution.
• Stir an) a**ow to sett*e
• ;n a c*ean/)r! 50m8 3eaer s*ow*!
)ecant te so*ution a**owin- te cr!sta*s of
Anhydrous sodium sulfate to remain at te
3ottom of te first container.
• 6inse 150m8 3eaer wit a sma** amount
of Dichloromethane to transfer remainin-
se)iment to te 50m8 3eaer.
Euation Setup:
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # B E+aporation 6esu*ts
%ateria*s Euipment 3ser+ation:
• So*ution was -ent*! eate) an) a**owe)
to 3oi* for 10 minutes stirrin- occasiona**!.
• Aina* pro)uct of e+aporation was wite
an) cratere) in appearance.
• Extracte) an)
)rie) Dichloromethane
so*ution
• 50m8
3eaer
• $otp*ate
• $oo)
Desc:
• $eat so*ution on a otp*ate settin- &
un)er te oo) unti* )r!.
Euation Setup:
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # 7 6ecr!sta**iation 6esu*ts
%ateria*s Euipment3ser+ations:
• %ore tan 15m8 of co*) acetone was
necessar! to fu**! )isso*+e te )rie) samp*e
&0m8.
• So*ution went from c*ear to c*ou)! upon
te a))ition of petroleum ether.
• "))itiona* eatin- was necessar! to
e+aporate excess acetone from te samp*e.• "n ice 3at for a few minutes to ai)
cr!sta* formation.
• Drie) samp*e
• 12,15m8 Co*)
Acetone
• ;ce 3at
• Petroleum ether
• $otp*ate
• P*astic
pipet
• eaer
Desc:
• ")) 12,15m8 Co*) Acetone to )rie)
samp*e.
• $eat so*ution on otp*ate.
• ")) acetone in 2m8 increments 20m8
maximum as nee)e) to )isso*+e comp*ete*!.
• 6emo+e from otp*ate an) coo* s*i-t*!.
• ")) petroleum ether )ropwise swir*in-
te mixture unti* te so*ution as a c*ou)!
appearance.
• Coo* in ice 3at to assist cr!sta*
formation.Euation Setup:
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # < acuum Ai*tration 6esu*ts
%ateria*s Euipment
• Ai*ter paper
• 20m8
Petroleum ether co*)
• Acetone co*)
• Caffiene
so*ution
• 125 m8
Er*enme!er f*as
• 1 ucner
funne*
• 1 Ai*ter
f*as
• 6u33ertu3in-
• acuum
• 6in- stan)
an) c*amp
• Dropper
• Spatu*a
Desc:
• "ssem3*e te fi*tration apparatus see
)ia-ram on ri-t.
• P*ace te fi*ter paper in te ucnerfunne* an) moisten wit a few )rops of co*)
petroleum ether .
• (urn on te +acuum to ti-t*! affix te
fi*ter paper to te funne*.
• Dispense te purifie) f*uorene so*ution
on top of te fi*ter paper.
• 6inse te Er*enme!er f*as wit a sma**
amount of so*+ent an) swir* to transfer
remainin- so*ution to te funne*.
• Ai*ter unti* no more *iui) can 3e seen
passin- into te fi*ter f*as.
• ")) 5m8 of co*) so*+ent to te cr!sta*s
to remo+e an! remainin- impurities.
• as cr!sta*s & times usin- te co*)
so*+ent waitin- unti* te fi*trate stops
)rippin- 3etween eac was.
• 4se a spatu*a to transfer te purifie)
cr!sta*s to a pre wei-e) +ia*.
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Euation Setup:
Proc # B Dr!in- J"ir Dr! 6esu*ts
%ateria*s Euipment
• Extracte) an)
)rie) Dichloromethane
so*ution in +ia*
Desc:
• 8ea+e te *i) to te +ia* s*i-t*! a?ar to
a**ow air to enter.
• "ir )r! samp*e for one wee in
instructors )rawer
Euation Setup:
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # 9 %ass Pure Samp*e 6esu*ts
%ateria*s Euipment%ass Pure Samp*e
%ass wei- 3oat 2.7&B-
%ass 3oat F samp*e &.11B-
%ass samp*e &.11B J 2.7&B M 0.&<0-
3ser+ations:
• Aina* pro)uct a) a *oose texture/)i) not
c*ump was )u** wite an) a) a fi3rous
appearance.
• Dr! purifie)
caffeine samp*e in
wei- 3oat
• E*ectronic
3a*ance L0.001
• Ca*cu*ator
Desc:
• (are te 3a*ance
• Pre wei- a c*ean )r! wei- 3oat. 6ecor)
te mass.
• ei- te samp*e. 6ecor) mass to tree
)ecima* p*aces.
• Su3tract te pre+ious*! )etermine) mass
of te empt! wei- 3oat from te mass
measurement to )etermine te mass of te
purifie) caffeine samp*e.
• 6ecor) a** mass measurements to te
precision *imit of te 3a*ance L0.001.
Euation Setup:
%ass of wei- 3oat an) samp*e - Jmass of empt!wei- 3oat M mass of purifie) samp*e -
7/25/2019 Chem 315 -Extraction of Caffeine
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc # 10 Percent 6eco+er! 6esu*ts
%ateria*s EuipmentPercent 6eco+er!
G reco+er! M 0.&<0/0.'00 x 100 95G• Ca*cu*ator
Desc:
• Simi*ar in teor! to percent !ie*).
• 4se) wen no cemica* reaction taes p*ace.
• Determines uantit! of pro)uct !ie*)e) from
te uantit! of pro)uct use) in te fi*tration process.Euation Setup:
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Proc #11 %e*tin- Point 6esu*ts
%ateria*s EuipmentPurifie) Caffeine
1st %.P.
oC
2n) %.P. oC
2&& 2&B
2&' 2&7
"+-oC: 2&&.5 2&B.5 2&5
• Purifie) caffeine
samp*e
• Capi**ar! tu3es
• %e*,(emp
"pparatus
• atc -*ass
• Spatu*a
• (ermomet
er
• *asstu3in-
Desc:
• 4se a watc -*ass an) spatu*a to crus a
sma** amount of purifie) caffeine samp*e.
• (ap te samp*e wit te open en) of a
capi**ar! tu3e to *oa) 2mm
• Drop te capi**ar! tu3e c*ose) en)
)own trou- te -*ass tu3in- so te samp*e is
at te 3ottom of te tu3e.
• ;nsert te capi**ar! tu3e c*ose) en) )owninto te %e*,(emp )e+ice.
• $eat te samp*e increasin- te
temperature 2,&oC/ min to )etermine te rou-
me*tin- point.
• 6ecor) te 1st %.P. wen te compoun)
3e-ins to me*t.
• 6ecor) te 2n) %.P. to wen te samp*e is
c*ear *iui).
• 6ecor) temperatures to one )ecima*
p*ace.• Coo* te samp*e unti* so*i).
• 6eeat samp*e unti* approximate*! 10oC
3e*ow te rou- me*tin- point.
• Continue to eat te samp*e at a s*ower
rate 0.5oC/min.
• 6ecor) a secon) %.P. ran-e.
Euation Setup:
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Summar! of 6esu*ts:
(e mass of te i+arin ta3*ets was 0.<95-. (e percent caffeine per pi** was ''.7G. (e mass of te
purifie) caffeine samp*e was 0.&<0-. (e percent reco+er! for te extraction was 95G. (e a+era-e
me*tin- point of te purifie) caffeine samp*e was 2&5oC.
"na*!sis Conc*usions:
" po*ar mo*ecu*e wit a si-nificant !)ropo3ic portion te ox!-en an) nitro-en atoms witin te
caffeine mo*ecu*es= structure are stron-*! e*ectrone-ati+e an) )raw e*ectrons in teir co+a*ent 3on)s wit
car3on towar)s temse*+es. (is uneua* sarin- of e*ectrons resu*ts in an une+en )istri3ution of
e*ectrone-ati+e car-e witin te mo*ecu*e or po*arit! were car3on carries a s*i-t*! more positi+ecar-e an) nitro-en an) ox!-en carr! a s*i-t*! more ne-ati+e car-e.
en com3ine) wit water tis po*ar mo*ecu*e is easi*! )isso*+e) +ia te formation of !)ro-en 3on)s
wit free e*ectron pairs on te nitro-en an) ox!-en atoms an) is tus water so*u3*e. en com3ine) wit
a nonpo*ar so*+ent *ie Dichloromethane te !)ropo3ic se-ments of te Caffeine mo*ecu*e interact wit
te Dichloromethane. (e increase) so*u3i*it! of caffeine in Dichloromethane 3! comparison to tat in
water faci*itate) te extraction an) iso*ation of te caffeine from water inso*u3*e constituents of te ta3*et
en com3ine) wit an aueous so*ution of caffeine in a separator! funne* an) -ent*! a-itate) te
caffeine separate) into te or-anic )ic*orometane c*ear *a!er. ecause Dichloromethane is )enser ta
water tis *a!er san to te 3ase of te f*as. & tota* a))itions of Dichloromethane were use) to extract asmuc caffeine as possi3*e from te so*ution.
" sma** amount of Anhydrous sodium sulfate was a))e) to remo+e excess water from te extracte)
so*ution. "n!)rous compoun)s attract an) form stron- 3on)s wit water mo*ecu*es ai)in- in teir
remo+a*. "n! Dichloromethane tat remaine) in te so*ution was ten e+aporate) 3! -ent*! eatin- te
samp*e on a ot p*ate.
"s a fina* means of purification acetone an) petro*eum eter were use) to recr!sta**ie te iso*ate)
caffeine. (ese so*+ents are i)ea* for te recr!sta**iation of tis compoun) as caffeine is on*! so*u3*e in
tem at e*e+ate) temperatures. " minima* +o*ume of so*+ent was a))e) to te cr!sta*s an) te so*ution
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
was -ent*! eate) unti* omo-enous. acuum fi*tration was ten use) to ar+est te cr!sta*s from temoter *iuor an) te samp*e was transferre) to a wei- 3oat an) a**owe) to air )r! for one wee.
" wee *ater te purifie) samp*e was wei-e) usin- an e*ectronic 3a*ance to assess te fina* mass 0.&<0-
(is in)icates teoretica**! tat 95G of te tota* caffeine in te 2 i+arin ta3*ets 0.'00- was reco+ere) in
te extraction an) on*! 0.020- was *ost.
(o +erif! te i)entit! of te compoun) an) assess its purit! te me*tin- point was )etermine) usin- te
%e*(emp )e+ice. (e a+era-e me*tin- point recor)e) 2&5oC was witin & )e-rees of te *iterature +a*ue
2&B.1oC in)icatin- tat te compoun) extracte) is re*ati+e*! free of impurities.
" potentia* source of error in tis experiment is swir*in- te so*ution too +i-orous*! in te seprator! f*as)urin- eac extraction. (is can cause an emu*sion to form main- iso*ation of te )esire) materia* from
te so*ution more )ifficu*t an) in turn te resu*tin- compoun) *ess pure.
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Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
8iterature Summar! 4nnowns S!ntesie) Compoun)s
4nnown No.
C"S No. 5<,0<,2
Name ;4P"C
&7,Di!)ro,1&7,
trimet!*,
1 H ,purine,2B,
)ione
S!non!ms
Caffeine
%e*tin- Point
oC
8it 2&B.1oC
Exp 2&5.0 oC
8it
Exp
8it
Exp
8it
Exp
oi*in- Point
o
C
8it 17< OC
Exp
8it
Exp
8it
Exp
8it
Exp
6efracti+e ;n)ex
nD20
8it 1.B79
Exp
8it
Exp
8it
Exp
8it
Exp
So*u3i*it!
6e* to ater
8it 2 -/100 m8
6.(. / BB -/100 m8
3oi*
Exp
8it
Exp
8it
Exp
8it
Exp
Densit!
6e* to ater
8it 1.2& -/cm& at20 OC
Exp
8it
Exp
8it
Exp
8it
Exp
%o*ecu*ar
Aormu*aC<$10N'2
7/25/2019 Chem 315 -Extraction of Caffeine
http://slidepdf.com/reader/full/chem-315-extraction-of-caffeine 18/18
Experiment: Date:
Extraction of Caffeine 10/27/15
Name Partners Drawer No. Course / Section
Kater!n Soto N/" #21C$E%
&15/20'
Structura*
Aormu*a