FACULTAD DE QUÍMICA E ING. QUÍMICA E.A.P. QUÍMICA 07.1 DEPARTAMENTO ACADÉMICO DE QUÍMICA ORGÁNICA CURSO DE QUÍMICA ORGÁNICA AII
PRÁCTICA 04: ESTERIFICACIÓN HORARIO:
Miércoles 13:00 – 17:000 (Laboratorio B)
PROFESORA:
Gloria Eva, Tomas Chota
FECHA DE REALIZACIÓN: 03 e ma!o e "01# FECHA DE ENTREGA:
10 e ma!o e "01#
INTEGRANTES:
1$07000% – Ceballos &livera, Carlos 'mar Lima – er*
201 ! I
1.R 1. RESUMEN Esta +rctica se reali-. co/ el obetivo e esarrollar / +roceso e estericaci./ aecao +ara la s2/tesis el acetato e isoamilo 'ems se
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bsc. se+arar el +rocto tili-a/o téc/icas e se+araci./ 4actibles +ara la s2/tesis Los ésteres so/ erivaos e cio m! com/es +rese/tes e/ +la/tas ! a/imales, co/ sos 5e va/ ese 4ra6a/cias ! cera hasta 4rmacos ! isolve/tes i/striales e si/teti-a/ 6e/eralme/te co/e/sa/o / cio carbo82lico co/ / alcohol, +roceso 5e se +ee ar +or Esterifcación de o Esterifcación Fischer o Esterifcación con destilación azeotrópica E/ esta +rctica se si/teti-. el acetato e isoamilo, 4ra6a/cia e los +lta/os, sa/o la estericaci./ e 9ischer 9ischer ra/te la +rctica, se hi-o reaccio/ar el alcohol isoam2lico co/ e8ceso e cio acético sa/o el cio sl4*rico como catali-aor cio La reacci./ se llev. a cabo e/ ebllici./ co/ re;o ra/te /a hora, observ/ose coloraci./ mbar mbar , i/ica/o 5e el +roceso 4e eca-
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TA"LA DE CONTENIDO 1 esme/ esme/ " " A/trocc A/trocci./ i./ $ 3 ri/ci+ios ri/ci+ios te.ricos te.ricos % $ etalles etalles e8+erime/t e8+erime/tales ales # $1 $1
Materia Materiales les # #
$"
eactivo eactivos s # #
$3
roceim roceimie/to ie/to e8+erime/ta e8+erime/tal l # #
% esltao esltaoss e8+erime/ta e8+erime/tales les = # Clclos Clclos = 7 '/lisis '/lisis ! iscsi./ iscsi./ e resltaos resltaos = Co/clsio/ Co/clsio/es es 10 ecome/a ecome/acio/es cio/es 10 10
'/e8 '/e8os os 11 11
11
e4ere/c e4ere/cias ias 1# 1#
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2.IINTRODUCCIÓN 2. Los ésteres co/stit!e/ / am+lio 6r+o e com+estos or6/icos 5e +osee/ la 4orma FC&F&F, 5e sr6e/ 6e/eralme/te e la co/e/saci./ e / alcohol ! / cio carbo82lico, libera/o a6a Los ésteres est/ e/tre los erivaos e cio ms com/es +rese/cia e/ la /atrale-a est am+liame/te e8te/ia ! cm+le/ /a 6ra/ ca/tia e 4/cio/es 'l6/os e los eem+los ms com/es e ésteres la e/co/tramos e/ la 4ra6a/cia e al6/os 4rtos ! ;ores, como +or eem+lo el acetato de isoamilo e los +lta/os, el butirato de metilo e la ma/-a/a, el acetato de acilo e la /ara/a, butirato de etilo e la +iHa ! mchos otros ms E/ estos casos se sa/ como $%&'$()*$+(,- Ca/o los ésteres se 4orma/ a +artir e cios carbo82licos e cae/a m! lar6a, los com+estos reslta/tes so/ s.lios i/miscibles e/ a6a co/ocios como ,%$-, las cales se e/ce/tra/ e/ a/imales ( palmitato palmitato de cetilo e/ balle/as), e/ +la/tas o so/ +rocias +or i/sectos ( palmitato palmitato de miricilo o cera e abea) Ca/o estos cios carbo82licos e cae/a lar6a se /e/ a / 6licerol (1,",3F+ro+a/otriol) se 4orma / ti+o es+ecial e 6rasas +rese/te e/ los or6a/ismos vivos co/ocia como (%)/)%)&- Ca/o so/ c2clicos se e/omi/a/ $(&+$- ! cm+le/ iversos roles biol.6icos como las 4eromo/as e iversas es+ecies e i/sectos ! mam24eros 9i/alme/te +oemos e/co/trarlos acom+aHaos e otros 6r+os 4/cio/ales esem+eHa/o 4/cio/es biol.6icas como es el caso e la 3)($')+$ C o cio LFasc.rbico ' /ivel i/strial tambié/ +osee/ /a 6ra/ variea e a+licacio/es Los ésteres ms +e5eHos, como el acetato de etilo , se sa/ como )-&,+(,- ! com+o/e/tes e iversos +roctos La nitrocelulosa es / solve/te e resi/as E/ 5$%'$6()$ cm+le/ 4/cio/es como a/tisé+ticos, o/e e/co/tramos al +o+lar cio acetilsalic2lico o as+iri/a 9i/alme/te, ca/o se +olimeri-a/ los ésteres, se 4orma/ los &)-(,%,-, 5e so/ +ol2meros termo+lsticos am+liame/te saos +ara e/vases escartables ! te8tiles si/téticos como el rayón
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#.P #. PRINCIPIOS TEÓRICOS Los ésteres 4rece/teme/te se obtie/e/ a +artir e / cio carbo82lico ! s alcohol corres+o/ie/te e/ /a reacci./ e e5ilibrio como la si6ie/te:
H9
FIG. 1. Es5ema 6e/eral e /a reacci./ e estericaci./
El +rot./ sobre la ;echa i/ica 5e los cios catali-a/ el +roceso Ge/eralme/te se em+lea como catali-aor / cio mi/eral, salme/te cio sl4*rico otro cio (+oco voltil) E/ la reacci./ e estericaci./ se elimi/a /a molécla e a6a El a6a 5e se +roce te/er a i/vertir el e5ilibrio, es ecir, a hiroli-ar /evame/te el éster ! iri6ir la reacci./ hacia los +roctos e +artia ara mi/imi-ar esto se tili-a/ iversos métoos +ara es+la-ar el e5ilibrio hacia los +roctos, como 4e me/cio/ao e/ la rctica 03 , +or sim+le elimi/aci./ el a6a se6*/ se va 4orma/o La ecaci./ 52mica 5e escribe la 4ormaci./ el acetato e etilo +or reacci./ el cio acético co/ el eta/ol es: J"&$ CJ3C&&J K C"J%&J
CJ3CJ&&C"J% K J"&
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4.D 4. DETALLES EPERIMENTALES $1 M'TEA'LE • • • • • • • • • •
Matra- es4érico e "%0ml robeta 6raaa e "% 0% ml o+orte /iversal " i/-as ! /eces Ma/6eras e4ri6era/te Liebi6 " aso e +reci+itaos "%0 ml era e eca/taci./ e 100 ml la/cha e Cale/tamie/to Bala/-a i6ital
$" E'CTA& • • • • •
Dcio acético 100> 6rao a/al2tico 'lcohol isoam2lico Dcio sl4*rico co/ce/trao ",=> 6rao reactivo 'C erlas e virio Clorro e soio 6rao reactivo 'C
$3 &CEAMAE?T& ENEAME?T'L 1) E/ os os vasos e +reci+ita +reci+itaos os se miiero/ miiero/ "% ml e cio cio acético acético ! "0 "0 ml e alcohol isoam2lico +or se+arao ! se +recale/taro/ saveme/te e/ la +la/cha e cale/tamie/to ") e aHaier aHaiero/ o/ "% ml e cio cio acético acético ! "0 ml e e alcohol alcohol isoam2lic isoam2lico o +recale/taos e/ el matra- es4érico ! se a6it. hasta me-clar ambos com+estos e 4orma homo6é/ea 3) e aHaiero/ aHaiero/ % ml e e cio sl4*rico sl4*rico co/ce/t co/ce/trao rao e 4orma 4orma 6raal 6raal a6ita/o a6ita/o el matra- co/sta/teme/te mie/tras se aHa2a el cio
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$) '+e/as '+e/as se a6re6. a6re6. el cio, cio, Ose aHaier aHaiero/ o/ las +erlas +erlas e virio, virio, se i/stal. i/stal. el re4ri6era/te ! se e/ce/i. la +la/cha e cale/tamie/to Mo/ta/o el e5i+o como se a+recia e/ la ima6e/ %) e cale/t. cale/t. a ebllici./ ma/te/ie/ ma/te/ie/o o el re;o ra/te ra/te a+ro8 a+ro8imaame imaame/te /te 1 hora Le6o e este +erioo se e. e/4riar hasta tem+eratra ambie/te
#) e colocaro/ colocaro/ %0 %0 ml e a6a e/ la +era +era e eca/taci./ eca/taci./,, le6o se a6re6. a6re6. too el l25io el matra- ! se a6it. +ara le6o eca/tar la 4ase acosa 7) Le6o, Le6o, se aHaiero/ aHaiero/ /evame/ /evame/te te "% ml e a6a a6a estilaa, estilaa, se a6it. ! se se eca/t. eca/t. se+ara/o la ca+a i/4erior (acosa) =) ' co/ti/ac co/ti/aci./ i./ se +re+ar. +re+ar. /a solci./ solci./ e e bicarbo/ato bicarbo/ato e soio soio al 1%> ! se lav. la ca+a or6/ica 3 veces co/ "%ml e solci./ e/ caa ocasi./
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8.R 8. RESULTADOS EPERIMENTALES El volme/ obte/io e acetato e etilo es: olme/ obte/io:
22 '
.C . CÁLCULOS rimerame/te se etermi/. la ecaci./ bala/ceaa e la s2/tesis e acetato e isoamilo
&bservamos 5e +or caa mol e cio acético o alcohol isoam2lico, se obtie/e / mol e acetato e isoamilo E/to/ces calclamos los moles tili-aos e reactivo 'lco lcohol isoa soam2lic 2lico o: +re-a 20 ml ×
0.81 g 1 ml
×
Dcio acéticoR a/al2tico 25 ml ×
1.05 g 1 ml
M P ==1% 6Qmo Qmol
1 mol 88.15 g
1 mol 60.02 g
'sm smie/ e/o 100>
e/sia P 1,0% 6Qml
100> 6rao
0.1838 mol
=
M P #0,0" 6Qmol
×
e/sia ia P 0=1 6Qml
= 0.4374
mol
&bservamos 5e el cio acético se e/ce/tra e/ e8ceso ! el alcohol es el reactivo limita/te Como caa mol e alcohol isoam2lico +roce / mol e acetato e isoamilo,
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m m+ 25 g
= 0.15 ⟹
m= 4.417 g
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7.A 7. ANÁLISIS = DISCUSIÓN DE RESULTADOS RENDIMIENTO DE LA REACCIÓN
El +orce/tae e re/imie/to e la reacci./ 4e co/sierableme/te alto, =0#>, +or lo 5e la reacci./ 4e .+tima 'tribimos la ecacia e la reacci./ al e8ceso e /o e los reactivos, 5e es+la-. el e5ilibrio e la misma hacia el lao e los +roctos se6*/ el +ri/ci+io e Le ChItelier ChIteli er 'ems, al haberse +recale/tao los reactivos a/tes e me-clarlos, esto +o haber ame/tao s solbilia, ismi/!e/o el ries6o e 4ormaci./ e /a emlsi./ ! ame/ta/o la l a ecacia e la reacci./ DISMINUCIÓN DE LA ACIDEZ
ra/te la +rctica, se lav. la 4ase or6/ica ra/te % veces +ara ismi/ir la acie-, observ/ose 5e el +J /alme/te ismi/!. hasta 10 Esto se +ee e8+licar ebio a la reacci./ 5e se a e/tre el cio sl4*rico e/ solci./ ! el bicarbo/ato e soio: "?aJC&3 K J"&$ ?a"&$ K J"C&3
Como se a+recia, se 4orma sl4ato e soio ! cio carb./ico El cio carb./ico es i/estable ! r+iame/te se escom+o/e e/ a6a ! i.8io e carbo/o "J"C&3 F "C&" K "J"&
e esta 4orma +oemos e8+licar la ismi/ci./ e la acie- 'mbas reaccio/es /alme/te se +ee/ resmir como: "?aJC&3 K J"&$ ?a"&$ K "C&" K "J"&
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;.C ;. CONCLUSIONES •
•
•
•
La estericaci./ e 9ischer es /a reacci./ 5e +ermite obte/er / éster a +artir e / cio carbo82lico ! / alcohol co/ catlisis cia E/ esta +rctica se hi-o reaccio/ar el cio acético co/ alcohol isoam2lico +ara obte/er acetato e isoamilo, / éster 5e a el aroma maro a los +lta/os ra/te esta +rctica se +o com+robar 5e la estericaci./ e 9ischer es / métoo a+ro+iao +ara lo6rar /a s2/tesis e alto re/imie/to e co/cl!. 5e la reacci./ es / e5ilibrio 5e se es+la-a hacia el lao e los +roctos +or el e8ceso e /o e los reactivos El cio acético es el reactivo e/ e8ceso e observ. 5e el +recale/tamie/to e los reactivos ame/ta s solbilia ! hace 5e la reacci./ sea ms eca-
<.R <. RECOMENDACIONES •
•
•
e recomie/a +recale/tar el cio acético ! el alcohol isoam2lico +ara lo6rar /a isolci./ ms e4ectiva ! evitar 5e se 4orme /a emlsi./ 'l mome/to e reali-ar el lavao e la ca+a or6/ica co/ a6a estilaa, es recome/able 5e la solci./ e bicarbo/ato se calie/te li6erame/te ! se ha6a r+iame/te +ara evitar 5e el bicarbo/ato +reci+ite ta+o/ea/o la bo5illa e la +era e eca/taci./ Tambié/ Tambié/ es recome/able cale/tar saveme/te la solci./ acosa e bicarbo/ato hasta 5e se iselva too el bicarbo/ato e soio ?o obsta/te se ebe te/er ciao e /o cale/tar e8cesivame/te la solci./ +es el bicarbo/ato se escom+o/e térmicame/te se6*/: "?aJC&3
?a"C&3 (s) K C&" (6) K J "& (6)
e +ee a+reciar la esi/te6raci./ ca/o la solci./ em+ie-a a liberar brbas e C&"
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10. ANEOS 1) e/a e/a e i/i5e las +ri/ci+ales +ri/ci+ales i4ere/c i4ere/cias: ias: 4/ame/to 4/ame/to,, e5i+o, reactivo reactivoss e /a estericaci./ a-eotr.+ica ! /a estericaci./ 9ischer 9ischer
9/ame /to
E-(,%)>$)?+ F)-@,% Este +roceso co/siste e/ la 4ormaci./ e / éster a +artir e / cio carbo82lico ! / alcohol e/ /a reacci./ catali-aa +or / cio mi/eral tili-a/o / e5i+o e re;o El e5ilibrio e la estericaci./ se es+la-a hacia el lao e los +roctos a6re6a/o /o e los reactivos e/ e8ceso 9i/alme/te el +rocto se lava co/ bicarbo/ato e soio +ara elimi/ar el catali-aor catali-aor e tili-a / e5i+o e re;o 5e es bsicame/te / matra- es4érico co/ectao a / re4ri6era/te 5e co/e/sa r+iame/te los va+ores salie/tes
E-(,%)>$)?+ A*,&(%?)$ Este +roceso co/siste e/ la reacci./ e / éster a +artir e / alcohol ! / cio carbo82lico si/ el so e catali-aores El e5ilibrio e la estericaci./ se es+la-a hacia el lao e los +roctos elimi/a/o el a6a 5e se 4orma, +ara esto, se a6re6a a la me-cla i/icial / tercer com+o/e/te 5e 4orme / a-e.tro+o e +/to ebllici./ m2/imo co/ el a6a, elimi//ola +or estilaci./ e tili-a e/ e5i+o se+araor, co/ocio como ea/FtarS, el cl elimi/a el a6a e/ la 4orma e / a-e.tro+o, se+ar/ola
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") Escriba Escriba el meca/ismo meca/ismo e reacci./ reacci./ e esteric estericaci./ aci./ 5e 5e ha obte/io obte/io e/ la +rctica +rctica
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El +ri/ci+io e Le ChItelier sostie/e 5e si / sistema 5e est e/ e5ilibrio se somete a / cambio e8ter/o, como cambio e +resi./, tem+eratra, volme/ o co/ce/traci./ e al6/o e los reactivos, el sistema se astar e ma/era 5e +ea co/trarrestar +arcialme/te el cambio al cal est sometio ' co/ti/aci./ se me/cio/ar/ os eem+los: E,'& 1: ra/te esta +rctica, la estericaci./ es /a reacci./ e/ e5ilibrio, es ecir 5e los +roctos +or2a/ volver a ser reactivos ara 6ara/ti-ar 5e se 4orme too el +rocto +osible se a+lica el +ri/ci+io e Le ChItelier, +ara esto ha! os o+cio/es: 1) e a6re6a / e8ceso e /o e los reactivos (e/ este caso el cio acético) lo cal ame/ta s co/ce/traci./ ! el sistema e/ e5ilibrio ismi/!e icha co/ce/traci./ ame/ta/o la 4ormaci./ e +roctos ") e e8trae e l a6a 4ormaa, lo cal ismi/!e s co/ce/traci./ ! hace 5e el sistema e/ e5ilibrio 4orme ms +rocto +ara re+o/er el a6a e8tra2a E,'& 2: E/ la 4ormaci./ e ?J3 se hace reaccio/ar / mol e ?" 6aseoso co/ 3 moles e J" 6aseoso e/ /a reacci./ 5e tambié/ 4orma / sistema e/ e5ilibrio i al reci+ie/te e reacci./ le ismi/imos el volme/ a la mita (ame/ta/o s +resi./ al oble), el sistema e/ e5ilibrio 4ormar ms +rocto +ara ismi/ir la +resi./
#) Calcl Calcle e el > e re/im re/imie/ ie/to to Esto se res+o/e e/ la +arte CÁLCULOS e este i/4orme
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Tri6licério Tri6licério
El meca/ismo e reacci./ es:
'lcohol
'c Grasos (bioiesel) (bioiesel) 6licerol
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ESTRUCTURA
NOM"RE = OM"RE = FUNCIÓN FUNCIÓN A,($(& , ,()&: isolve/te i/strial e baa to8icia eca- +ara /a 6ra/ variea e com+estos Tambié/ Tambié/ es aitivo a itivo e/ lim+iaores, +e6ame/tos, etc 'm+liame/te tili-aos como "6()%$(& , ,()&: isolve/tes +ara +i/tras ! acabaos.
) Me/cio/e Me/cio/e % com+estos com+estos eshira eshirata/tes ta/tes ! i6a i6a cl es el ms ms eco/.mico eco/.mico C&%6%& , B)& $+@)%&: e tili-a mcho +or ser e 6ra/ ca+acia ! relativame/te barato i/ embar6o, es basta/te le/to ! moeraame/te eca- •
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P$')($(& , ,()&: Co/ocio como es+erma e balle/a, es / éster tili-ao +or las balle/as +ara re6lar s ;otabilia e/ el a6a ZJ7&,,+) $,($(&: Es / im+orta/te com+o/e/te e las 4eromo/as se8ales e iversas es+ecies e +olillas ',() 2$')+&,+*&$(&: 'roma caracter2stico e la va
11)C.mo se +ee com+robar la obte/ci./ el ésterU A/vesti6e reaccio/es e com+robaci./ Ja6a las reaccio/es co/ s éster obte/io A/i5e los reactivos 5e se sa/ e/ estas com+robacio/es