Isolation of Eugenol from Cloves by Steam Distillation and its Identification by Infrared Spectroscopy Eim A.

Chemist CHEM 303 June 16, 2005 INTRODUCTION Essential oils are the volatile com onents associate! "ith the aromas o# man$ lants.1 %n this e& eriment, the essential oil eu'enol (the main com onent o# oil o# cloves) "ill *e isolate! #rom 'roun! cloves usin' the techni+ue o# steam !istillation, "hich is o#ten use! to isolate li+ui! natural ro!ucts #rom lants.2 ,he rinci le o# steam !istillation is *ase! on the #act that t"o immisci*le li+ui!s "ill *oil at a lo"er tem erature than the *oilin' oints o# either ure com onent, *ecause the total va or ressure o# the hetero'eneous mi&ture is sim l$ the sum o# the va or ressures o# the in!ivi!ual com onents (i. e. -, . -oA / -o0, "here -o is the va or ressure o# the ure li+ui!s). ,his lea!s to a hi'her va or ressure #or the mi&ture than "oul! *e re!icte! #or a solution usin' 1aoult2s 3a" (that is -, . -oA4A / -o040, "here 4 is the mole #raction o# the com onent in the mi&ture). ,he hi'her total va or ressure lea!s to a lo"er *oilin' oint #or the mi&ture than #or either sin'le com onent.2 5urin' the isolation o# a li+ui! natural ro!uct *$ steam !istillation, "ater is one o# the com onents, an! the li+ui! natural ro!uct *ein' isolate! ("hich is immisci*le "ith "ater) is the other com onent. ,he ro!uct can *e steam !istille! #rom the natural source at a relativel$ lo" tem erature (al"a$s less than 100 oC), thus avoi!in' !ecom osition o# the ro!uct.2 6team !istillation can *e carrie! out in t"o "a$s7 the !irect metho! an! the live steam metho!.3 %n the !irect metho!, steam is 'enerate! *$ *oilin' a mi&ture o# the source o# the com oun! o# interest an! "ater. ,he live steam metho! is carrie! out *$ assin' steam #rom an e&ternal source into the !istillation #las8. ,he !irect metho! o# steam !istillation "ill *e use! in this e& eriment an! is carrie! out on a semi9 micro scale usin' the a aratus sho"n in :i'ure 1 *elo"7

Figure

-a'e 1

<roun! cloves an! "ater "ill *e char'e! into the !istillation #las8 sho"n in the #i'ure. ,he mi&ture "ill then *e heate! to *oilin' on a hot late "ith an aluminum heatin' *loc8 an! the !istillate (a eu'enol="ater mi&ture) "ill *e collecte!. ,he eu'enol "ill then *e se arate! #rom the "ater *$ e&traction "ith meth$lene chlori!e. ,he meth$lene chlori!e solution "ill then *e !rie!, !ecante! an! eva orate! to a##or! the li+ui! eu'enol. ,he ercent recover$ #rom cloves "ill *e !etermine! an! the ro!uct "ill *e anal$>e! *$ transmission in#rare! s ectrosco $ (%1) as a neat sam le usin' 4aCl lates5 to con#irm its structure. ,his "ill *e !one in t"o "a$s7 (1) *$ loo8in' at the ma?or a*sor tions in the s ectrum an! com arin' them to a correlation ta*le6 an! (2) *$ com arin' the s ectrum to that o# an authentic sam le. ,he ma?or %1 a*sor tions are e& ecte! to *e 3200 @ 3500 cm91 (AH stretch), 3000 @ 3150 cm91 (s 2 C9H stretch), 1600 @ 16B0 cm91 (al8ene C.C), an! 1;00 @ 1600 cm91 (aromatic C.C)6. Table of C!emical SubstancesC 1ea'ent Cloves Meth$lene chlori!e 6o!ium sul#ate Eu'enol 6tructure=:ormula 999 CH2Cl2 4a26A; 1ole Ather 6olvent 5r$in' a'ent -ro!uct Mol. Dt. 999 B;.E3 999 16;.20 M 999 9EC oC 999 912 to 910 oC 0 999 3E @ ;0 oC 999 25; oC 5ensit$ 999 1.32 '=m3 999 1.06 '=m3

C10H12A2

-a'e 2

Safety InformationC Compounds" #aterial Cloves Meth$lene chlori!e 6o!ium 6ul#ate Eu'enol To$ic% 4o 4o 4o 4o Corrosive% 4o 4o 4o 4o Flammable% 4o 4o 4o 4o Carcinogenic% 4o Fes 4o 4o

Tec!ni&ues7 Dhen heatin' a reaction a aratus, *e sure that it is o en to the air so that ressure *uil! u an! su*se+uent ru ture o# the a aratus !oes not occur. Dhen heatin' li+ui!s, ma8e sure the li+ui! is stirre! (or a *oilin' chi is a!!e!) to revent *um in'. Dhen er#ormin' an e&traction, ma8e sure to vent the centri#u'e tu*e o#ten to revent ressure *uil!9 u . E'(ERI#ENT)* ,he a aratus sho"n in :i'ure 1 "as assem*le! usin' a 259m3 roun! *ottom #las8 as the !istillation ot. ,he !istillation ot "as char'e! "ith 1.032 ' o# 'roun! cloves an! 15 m3 o# !istille! "ater. ,he cloves "ere allo"e! to soa8 in the "ater until thorou'hl$ "ette! (a*out 15 min), then the mi&ture "as !istille!, the !istillate *ein' collecte! at the rate o# a*out one !ro ever$ 2 @ 3 secon!s. A#ter a*out 6 m3 o# !istillate "ere collecte!, the !istillate "as e&tracte! "ith 2.0 m3 o# CH2Cl2 (a8a 5CM), then a'ain "ith (2 & 1.0 m3) o# 5CM. ,he 5CM e&tracts "ere com*ine!, !rie! over 4a26A;, an! eva orate! to 'ive the ro!uct eu'enol as a ale $ello" oil (0.0CC0 '). RESU*TS )ND DISCUSSION 6team !istillation o# cloves ro!uce! 0.0CC0 ' o# an oil "hich containe! in its %1 s ectrum the #unctional 'rou s A9H (at 3560 cm91), s 2 C9H (30B0 @ 3000 cm91), ali hatic C9H (2EB0 @ 2E;0 cm91), an! *oth al8ene C.C (at 16;0 cm91) an! aromatic C.C (at 151; cm91). ,he %1 s ectrum is attache! to this re ort. ,hese !ata are consistent "ith the structure o# eu'enol, sho"n in :i'ure 2 *elo"7

Figure +" Eugenol

-a'e 3

%n a!!ition, the %1 o# the ro!uct #rom the steam !istillation o# cloves closel$ corres on!s "ith that o# an authentic sam le o# eu'enol sho"n in the la* te&t.B ,here#ore, it can *e conclu!e! that the oil "hich "as isolate! #rom cloves is in #act, eu'enol. 0.0CC0 ' o# eu'enol "as recovere! #rom 1.032 ' o# cloves. ,his corres on!s to a ercent recover$ o# C.;6G7 Amt. Eu'enol isolate! 0.0CC0 ' G 1ecover$ . 999999999999999999999999999999 . 99999999999999 & 100 . C.;6G Amt. Cloves use! 1.032 ' Althou'h the G recover$ seems ver$ lo", the e& eriment rocee!e! as lanne!. ,here "ere no s ills or other a*normal h$sical losses. %t is ossi*le that the ratio o# the si>e o# the 'lass"are to the theoretical amount o# eu'enol "hich can *e o*taine! #rom cloves in this e& eriment is lar'e, lea!in' to a!herence o# a lar'e ercenta'e o# the ro!uct on the si!es o# the 'lass a aratus. %# this is so, then steam !istillation o# a lar'er sam le o# cloves shoul! 'ive an im rove! recover$. Ather"ise, it can *e conclu!e! that cloves contain a ro&imatel$ C.5G eu'enol. SU##)R, )ND CONC*USIONS %n this e& eriment, it "as sho"n that a*out C.5G o# an oil coul! *e recovere! #rom cloves *$ steam !istillation. ,his oil "as i!enti#ie! as eu'enol *$ com arison o# its in#rare! s ectrum "ith an authentic sam le. REFERENCES 1. -avia, 5. 3.H 3am man, <. M.H Iri>, <. 6.H En'el, 1. <. Introduction to Organic Laboratory Techniques, A Microscale Approach; 3r! e!.H 0roo8s=Cole7 -aci#ic <rove, CA, 1EEEH . 13E. 2. -avia, 5. 3.H 3am man, <. M.H Iri>, <. 6.H En'el, 1. <. Introduction to Organic Laboratory Techniques, A Microscale Approach; 3r! e!.H 0roo8s=Cole7 -aci#ic <rove, CA, 1EEEH . 663. 3. -avia, 5. 3.H 3am man, <. M.H Iri>, <. 6.H En'el, 1. <. Introduction to Organic Laboratory Techniques, A Microscale Approach; 3r! e!.H 0roo8s=Cole7 -aci#ic <rove, CA, 1EEEH . 665. ;. -avia, 5. 3.H 3am man, <. M.H Iri>, <. 6.H En'el, 1. <. Introduction to Organic Laboratory Techniques, A Microscale Approach; 3r! e!.H 0roo8s=Cole7 -aci#ic <rove, CA, 1EEEH . 62B. 5. 6ee -avia, 5. 3.H 3am man, <. M.H Iri>, <. 6.H En'el, 1. <. Introduction to Organic Laboratory Techniques, A Microscale Approach; 3r! e!.H 0roo8s=Cole7 -aci#ic <rove, CA, 1EEEH . C;3 #or a !escri tion o# this t$ e o# sam le re aration. ,he hol!er !escri*e! in :i'ure 1E.1 "ill not *e use! #or this e& eriment. 6. -avia, 5. 3.H 3am man, <. M.H Iri>, <. 6.H En'el, 1. <. Introduction to Organic Laboratory Techniques, A Microscale Approach; 3r! e!.H 0roo8s=Cole7 -aci#ic <rove, CA, 1EEEH . A1E. C. 5ata ta8en #rom ro!uct !escri tions an! M6562s at the :isher 6cienti#ic "e*site. htt s7==ne".#ishersci.com (accesse! June, 2005). B. Introduction to Organic Laboratory Techniques, A Microscale Approach; 3r! e!.H 0roo8s=Cole7 -aci#ic <rove, CA, 1EEEH . 1;2.

-a'e ;

)NS-ERS TO .UESTIONS 1. Dh$ is eu'enol steam9!istille! rather than uri#ie! *$ sim le !istillationJ Eu'enol has a hi'h *oilin' oint (25; oC), an! man$ or'anic com oun!s !ecom ose at such hi'h tem eratures. 6team !istillation allo"s eu'enol to *e !istille! at a much lo"er *oilin' oint (K 100 oC), thus minimi>in' the otential #or !ecom osition. 2. %n a steam !istillation, the amount o# "ater actuall$ !istille! is usuall$ 'reater than the amount calculate!, assumin' that *oth "ater an! or'anic su*stance e&ert the same va or ressure "hen the$ are mi&e! than the$ e&ert "hen each is ure. Dh$ !oes one recover more "ater in the steam !istillation than "as calculate!J (Hint7 Are the or'anic com oun! an! "ater trul$ immisci*leJ) %n most cases, or'anic su*stances have some solu*ilit$ in "ater. %# this is true, then the amount o# "ater "hich is re+uire! to steam !istill the su*stance in its entiret$ is the calculate! amount lus an amount nee!e! to !istill over the amount o# su*stance !issolve! in "ater.

-a'e 5

1e ro!uce! #rom the 6 ectral 5ata*ase #or Ar'anic Com oun!s (6506). """.aist.'o.? =1%A50=6506=c'i9*in=creLin!e&.c'i (accesse! Ma$, 2006)