ESTERIFICATION Iwin Soossay Sathianathan Period 5 Mr Andrew Wong CPU Chemistry Grade 12, Taylors College Subang Jaya

Campus, No. 1 Jalan SS 1 !", #$ %% Subang Jaya, Selangor &arul 'hsan.

ABSTRACT

The produ tion o! ester in s"a##$s a#e is %ery i"portant as a #a&oratory e'peri"ent in organi he"istry( The purpose o! this e'peri"ent is to pro%ide a pra ti a# e'a"p#e o! the

synthesis o! an ester through esteri!i ation( A ar&o'y#i a id whi h is the ethanoi a id and an a# oho# whi h is the ethano#) wi## &e heated in the presen e o! on entrated su#phuri a id as the ata#yst to !or" the ester( The synthesis o! pure ester wi## undergo three stages in the esteri!i ation pro ess* esteri!i ation through re!#u') e'tra tion and disti##ation( The esteri!i ation through re!#u' pro ess set up apparatus is as shown in Figure 1( The e'tra tion pro ess set up apparatus is as shown in Figure +( The disti##ation pro ess is as shown in Figure ,( Esteri!i ation a hie%es e-ui#i&riu" at e%ery step in the rea tion.s "u#ti$step "e hanis" there are re!#u') e'tra tion and disti##ation( The rea tion is "o%e to the right) towards the end produ t( /ased on 0e Chate#ier.s prin ipa#( In this e'peri"ent) a #arge e' ess o! one o! the rea tant is used( Su#phuri a id a ts as ata#yst and used in this e'peri"ent &e ause ha%e a strong dehydrating apa&i#ity and he#p 1soa2 up. the rea tion( Water is a#so assisting in pu##ing the rea tion to the right( The o&3e ti%es o! this #a&oratory are to tea h us how to "a2e an ester as we## as to en!or e an understanding o! the pro ess o! esteri!i ation( This e'peri"ent is a#so ondu ted to pro%e that esters an &e produ ed !ro" ar&o'y#i a ids and a# oho#s(

INTRODUCTION

Esters are deri%ed !ro" ar&o'y#i a ids( The produ tion o! esters !ro" ar&o'y#i a ids and a# oho#s or &y ondensing a ids with a# oho# is 2nown as esteri!i ation( A ar&o'y#i a id ontains the $COO4 group) and in an ester the hydrogen in this group is rep#a ed &y a hydro ar&on group o! so"e 2ind( S ientists ha%e o"e up with "ethods to reate esters through esteri!i ation whi h is a #assi synthesis o! the Fis her esteri!i ation( This in%o#%es treating a ar&o'y#i with an a# oho# in the presen e o! a dehydrating agent( This pro ess has three steps( The steps in #ude esteri!i ation through re!#u') e'tra tion o! "i'ture and disti##ation o! produ t( The who#e pro ess in%o#%es the intera tion o! a o"pound possessing a hydro'y# group with an a id) with the e#i"ination o! water(

Sin e esteri!i ation is a re%ersi&#e rea tion) the a"ount o! the yie#d &e o"es in onsistent throughout the entire pro ess( There!ore)the a"ount o! ester p#anned to o&tain is not a urate( This is the "a3or pro&#e" !a ed in esteri!i ation te hno#ogy whi h arises !ro" the !a t that in the "a3ority o! ases a re%ersi&#e rea tion is in%o#%ed( To partia#ity the e-ui#i&riu" to the produ t side) one o! the rea tants "ust &e used in e' ess or one o! the produ t "ust &e re"o%e onstant#y during the rea tion( Ester synthesis rea tions are usua##y ondu ted with the he#p o! a id or &ase ata#yst( Progress has &een "ade to o%er o"e this pro&#e" in esteri!i ation rea tions(

A si"p#e esteri!i ation pro ess an &e arried out in a #a&oratory( The "anu!a turing o! esters &e o"es %ery use!u# in our dai#y #i!e( They are in%o#%ed in "a2ing per!u"es) os"eti s and arti!i ia# !ood !#a%ourings( Esters are a&undant in nature( They o ur natura##y in p#ants and ,

ani"a#s( In o"&ination with %o#ati#e o"pounds) ester an produ e p#easant aro"a o! !ruits( In ondu ting the e'peri"ent o! esteri!i ation) students are su&3e ted to &e intrested on studying organi dai#y #i!e( he"istry "ore deep#y( They are a&#e to understand the ro#e he"istry p#ays in their

EXPERIMENTAL

SUPPLIES. /utano#) ethanoi a id) on entrated su#phuri a id) sodiu" &i ar&onate) water) 566 "# &ea2er) a #u&ri ant78ase#ine petro#eu"9) &oi#ing hips) round$&otto"ed !#as2) 0ie&ig ondenser) wire gau:e) /unsen &urner) tripod stand) ru&&er tu&e) !i#ter !unne#) oni a# !#as2s and retort stand(

HAZARDS. The "ateria#s pro%ided "ust &e hand#ed with are( /e are!u# with the usage o!

on entrated su#phuri a id as it is orrosi%e( A#ways wear sa!ety g#ases &e ause the disso#ution o! su#phuri a id in water is %ery e'other"i and any onta t with it an ause per"anent &#indness( The 1"a#e and !e"a#e 3oin. ha%e to #u&ri ated to pre%ent it !ro" stu 2( Fina##y) when the so#ution is "i'ed with sodiu" ar&onate pre%ent the stop o 2 to !a e any person(

PROCEDURE. First) the pro ess o! re!#u' was arried out( 56"0 o! a# oho# and 56"0 o! ar&o'y#i a id was prepared in two di!!erent &ea2ers( The so#ution was then p#a ed into a round &otto" !#as2( 1"0 o! on entrated su#phuri a id was then added using a dropper together with so"e &oi#ing hips( The set up o! the e'peri"ent as shown in Figure 1 was then arranged and the "i'ture was re!#u'ed !or ,6 "inutes( A!ter ,6 "inutes and the "i'ture oo#s down) the "i'ture was trans!erred into a

separatory !unne# are!u##y a%oiding the &oi#ing hips to !#ow together with the "i'ture( 56"0 o! disti##ed water was then added into the separatory !unne#( The !unne# was swir#ed gent#y( The 5

!unne# was sha2en gent#y on e or twi e and the stop ode was opened on e in a whi#e to re#ease the pressure that was &ui#ding in the separatory !unne#( The !unne# was sha2en unti# no ar&on dio'ide gases e%o#%e when the separatory !unne# was %ented( The #ower a-ueous #ayer was re"o%ed and the e'tra tion was repeated with 56"0 o! Na +Co,) sodiu" ar&onate so#ution( The #ower #ayer was re"o%ed) and the a&o%e e'tra tion was repeated again with 56"0 o! disti##ed water( A!ter a## the a-ueous #ayer was re"o%ed) the top #ayer that was now #e!t was then trans!erred into a &ea2er( The &ea2er was then added with CaC# +) dry a# iu" h#oride( The "i'ture ontaining CaC#+ was !i#tered !ro" a !i#ter !unne# into another round &otto" !#as2 with the use o! !i#ter paper( The o##e ted !i#trate was heated unti# it rea hed a te"perature o! 166;C so that the water wi## e%aporate) separating it !ro" the deter"ining produ t( The water that was disti##ed !ro" the "i'ture was o##e ted into a &ea2er at the end o! the 0ie&ig ondenser( When the "i'ture hits the te"perature o! 1+6;C) a new &ea2er rep#a es the pre%ious &ea2er ontaining the disti##ed water as pure ester was &eing disti##ed at that te"perature( Pure ester was o##e ted at the end o! the pro ess(

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RESULTS

OBSERVATIONS. First#y) the produ t is o#our#ess( The produ t has a sweet s"e##( Produ t is #ess dense than water( Fina##y) the produ t !or"ed is inso#u&#e in water(

DISCUSSIONS

Esters are o#our#ess) !ragrant in s"e##) #ess dense than water and inso#u&#e in water( The produ t !or"ed is ethy# ethanoate( Ethy# ethanoate is o#our#ess( It has a !ragrant s"e## and ethy# ethanoate is inso#u&#e in water( It !#oats on top o! water) "a2ing it is #ess dense than water( There!ore) ethy# ethanoate has the physi a# properties o! an ester(

The esteri!i ation rea tion is a s#ow and re%ersi&#e( The he"i a# e-uation !or the rea tion &etween an a id RCOO4 and an a# oho# R>O4 is shown &e#ow( CN4+N?1COO4 ? CM4+M?1O4 CN4+N?1COOCM4+M?1 ? 4+O O R C O 4 ? R.O4 R C O R. on entrated O ? 4+O

In e'a"p#e) ethanoi

a id and ethano# are heated in the presen e o!

su#phuri a id as a ata#yst) ethy# ethanoate is produ ed( The e-uation is shown &e#ow( C4,COO4 ? C+45O4 C4,COOC+45 ? 4+O O C4, C O 4 ? C4,C4+O4 C4, C O C4+ C4, O ?4+O

Pure ester an &e on entrated &y the pro ess o! disti##ation( It is gathered at the te"perature o! 1+6 ;C( This is &e ause through the pro ess o! disti##ation) the so#ution o##e ted is water when the te"perature a hie%ed 166;C( The &oi#ing point o! ester is 1+6;C(The re!#u' pro ess

is to ensure that a# oho# rea ts o"p#ete#y with the ar&o'y#i a id( /esides) e'tra tion pro ess is to ensure a## the water and waste produ ts are re"o%ed( Su#phuri a id represent as the ata#yst or dehydrating agent to speed up the rea tion(

CONCLUSION

Pure ester an &e "ade &y using the re!#u') e'tra tion and disti##ation on the "i'ture o! a# oho#) ar&o'y#i a id and on entrated hydro h#ori a id( Esteri!i ation an &e arried out in the #a&oratory &y "i'ing ar&o'y#i a id and a id and heating the" in the presen e o!

on entrated su#phuri a id as the ata#yst( Pure ester an then &e separated !ro" the "i'ture &y disti##ation and o##e ted at 1+6;C(

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REFERENCES 1( Beus h) Peter( CA id Cata#y:ed Esteri!i ationD uni(regensburg.de( n(p) n(d( += No% +616( We&( +( C#ar2) Ei"( CEsteri!i ationD )hemguide.)o.u*( n(p) +66,( +@ No% +616( We&( ,( CMethod and Apparatus !or Esteri!i ationD +a,s.org( n(p) n(d( +@ No% +616( We&( 5( CFra tiona# Fisti##ationD u)dsb(on( a( +@ No% +616(We&( 5( CEsteri!i ationD )hemguide( o(u2( +A No% +616( We&(

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