Chem 315 -Extraction of Caffeine

7/25/2019 Chem 315 -Extraction of Caffeine

http://slidepdf.com/reader/full/chem-315-extraction-of-caffeine 1/18

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).



Experiment: Date:




&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.



Experiment: Date:




&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 -



Experiment: Date:




&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:



Experiment: Date:




&15/20'

Proc # & 8iui),*iui) Extraction 6esu*ts


• 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.



Experiment: Date:




&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:



Experiment: Date:




&15/20'

Proc # ' Dr!in- , "n!)rous So)ium Su*fate 6esu*ts


• (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:



Experiment: Date:




&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:



Experiment: Date:




&15/20'

Proc # 7 6ecr!sta**iation 6esu*ts


• %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:



Experiment: Date:




&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*.



Experiment: Date:




&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:



Experiment: Date:




&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 -



Experiment: Date:




&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:



Experiment: Date:




&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:



Experiment: Date:




&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



Experiment: Date:




&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.



Experiment: Date:




&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



Experiment: Date:




&15/20'

Structura*

Aormu*a

Chem 315 -Extraction of Caffeine

Documents

Transcript of Chem 315 -Extraction of Caffeine