S YNTHESIS OF 1-PHENYLAZO-2-NAPHTHOL J. V. DE GUZMAN DEPARTMENT OF DEPARTMENT OF CHEMICAL CHEMICAL ENGINEERING , COLLEGE OF ENGINEERING OF ENGINEERING UNIVERSITY OF THE OF THE PHILIPPINES, DILIMAN QUEZON CITY , PHILIPPINES DATE PERFORMED :
APRIL 15, 2015 INSTRUCTOR ’S NAME: ALLAN KENNETH REGUNTON
ABSTRACT Synthesis o !"o #o$%o&n's is si(ni)#!nt in the *ese!*#h #o$$&nities !n' in'&st*ies sh !s te+tie !n' oo' -e#!&se o thei* intense #oo* sh th!t they #!n -e &se' !s syntheti# 'yes. The e+%e*i$ent o#&ses on the synthesis o /0%heny!"o0 10n!%htho o* S&'!n0/ *o$ the !$iy o S&'!n 'yes -y e$%oyin( 'i!"oti"!tion *e!# *e!#ti tion on in !ni !niine ine to o*$ o*$ %hen %heny y'i 'i!" !"on oni& i&$ $ &n'e* &n'e* ! 'i!" 'i!"ot oti" i"!t !tio ion n *e!# *e!#ti tion on $e#h!nis$. The o*$e' %heny'i!"oni&$ &n'e*(oes 'i!"oni&$ #o&%in( *e!#tion 2ith 2ith 30n! 30n!%ht %htho ho. . Re#* Re#*ys yst! t! i" i"!t !tio ion n !n' !n' $et $etin in( ( %oin %ointt 'ete*$ 'ete*$in in!t !tio ion n !*e !*e !so !so e$%oye' e$%oye' to !ssess the %&*ity o the o-t!ine' %*o't. %*o't. The e+%e*i$ent e+%e*i$ent !so !i$s to in4esti(!te the %*o%e*ties o S&'!n0/ !s !n in(*!ine' 'ye. Res&ts sho2e' th!t the in(*!i in(*!ine' ne' S&'!n0/ S&'!n0/ 'ye is #onsi' #onsi'e*e e*e' ' !st !st !n' &nio* &nio*$ $ in the #otton #otton !-*i# $!5in( it ! (oo' 'ye. The synthesis *es&t to 6.6/ ( o S&'!n0/ !n' ! $etin( %oint o /76 8C 4e*y #ose to the theo*eti#! 4!&e o /7/ 8C. The #oseness o the $etin( %oint 4!&es i$%y the hi(h %&*ity o the )n! %*o't 2hie the !$o&nt o synthesi"e' %*o't i$%ies the s#ess o S&'!n0/ %*e%!*!tion !n' e!si-iity o the $etho' in synthesi"in( !"o #o$%o&n's. _____________________________________________________________________________________________ __________________________________________________________________________ ___________________ _________________________________
INTRODUCTION Amin Amine e !"e !"e #$m% #$m%$& $&n' n' #$n( #$n(!i !ini nin) n) ni("$)en *i(+ ! $ne %!i" (+!( i !((!#+e' ($ !n !-. $" !"$m!(i# )"$&%/ T+e %"een#e %"een#e $ (+e $ne %!i" m!-e !mine !mine $(+ $(+ !i# !i# !n' !n' ne$ ne$%+i %+ii# i#// Amine !"e !$ #!e' $")!ni# 'e"i!(ie $ !mm$ni! !n' (+e. +!e (+e (+e )ene" ene"! ! $" $"m&! &!34 34 RN RNH H 2 $" %"im!". %"im!". !mine, !mine, R 2NH $" e#$n' e#$n'!" !". . 617 !mine !n' R N $" (e"(i!". (e"(i!". !mine / P"im!". !mine #!n "e!#( *i(+ ni("$& !#i' $" ni("i(e !( in !#i'i# me'i&m ($ .ie .ie' !( ( #!e !e' ' 'i!8$ i!8$ni ni& &m in !
%"$#e %"$#e #!e' #!e' 'i!8$(i8 'i!8$(i8!(i$ !(i$n n "e!#(i$n "e!#(i$n// Di!8 Di!8$( $(i8 i8!( !(i$ i$n n "e!#( e!#(i$ i$n n #!n #!n $##& $##&"" in !min !mine e #$n( #$n(!i !ini nin) n) ei(+ ei(+e" e" !!-. $" !"$m!(i# )"$&%/ H$*ee", !-.!mine 'i!8$ni&m %"$'( !"e e". "e!#(ie (+!( (+e. #!nn$( e i$!(e'/ T+&, (+e me(+$' i &&!. em%$.e' in %"im!". !".! ".!m mine ine $n. $n. !n' i( i( )ene" ene"! ! 617 "e!#(i$n i +$*n in Fi)&"e 1/ N!NO2, H9,
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Fi)&"e 1/ Gene"! 'i!8$(i8!(i$n "e!#(i$n $" !niine A"ene'i!8$ni&m !"e e". (!e !( !n' (+e. !"e e%e#i!. &e& e#!&e $ (+ei" 'i!8$ni$ )"$&% 3N;N4 617 *+i#+ #!n e "e%!#e' . ! ne$%+ie in ! (.%i#! ee#("$%+ii# !"$m!(i# 6<7 &(i(&(i$n &(i(&(i$n "e!#(i$n / An e=!m%e $ (+e ee#("$%+ii# !"$m!(i# &(i(&(i$n "e!# "e!#(i$ (i$n n (+!( (+!( !"ene !"ene'i! 'i!8$n 8$ni&m i&m !( !( &n'e")$ i 'i!8$ni&m #$&%in) "e!#( e!#(i$ i$n n *+e" *+e"e e !#(i !#(i! !(e (e' ' !"$m !"$m!( !(i# i# "in) + ! %+en$ !n' !".!mine e#! e#!me me !((! !((!#+ #+e' e' ($ (+e (+e 'i!8$ i!8$ni ni$ $ )"$& )"$&% % ($ .ie .ie' ' "i) "i)+( +(. . #$$ #$$""e' !8$ !8$ #$m%$&n'/ A )ene"! "e!#(i$n +$*in) +$*in) 'i!8$ni& 'i!8$ni&m m #$&%in) #$&%in) "e!#(i$ "e!#(i$n n "$m "$m (+e !"ene !"ene'i! 'i!8$n 8$ni&m i&m $"me' $"me' in (+e 'i!8$(i8!(i$n "e!#(i$n in Fi)&"e 1 i +$*n in Fi)&"e Fi)&"e 2 e$*/ e$*/ > !"ene'i!8$ni&
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Fi)&"e 2/ Gene"! 'i!8$ni&m #$&%in) "e!#(i$n A8$?#$&%e' #$m%$&n' +!e e=(e e=(en ni ie e %"!# %"!#(i# (i#! ! !%% !%%i# i#!( !(i$ i$n n in !"i$& !"i$& in'&(" in'&("ie ie !n' in "ee!" "ee!"#+e #+e e#!&e $ (+ei" in(ene #$$"/ T+ee #$m #$m%$&n' $&n' !"e !"e "i) "i)+(. +(. #$$" $"e' e#!&e $ (+e !8$ in-!)e 3N@N4 (+!( "in) in) (+e (+e (*$ (*$ !"$m !"$m!( !(i# i# "in) "in) ($ #$n&)!(i$n/ T+ei" e=(en'e' #$n&)!(e' B ee#("$n .(em en!e (+em ($ !$" in (+e iie %e#("&m $ (+e (+e ee# ee#(" ("$m $m!) !)ne ne(i (i# # %e# %e#(" ("&m &m )iin) )iin) (+ei" (+ei" #+!"!# #+!"!#(e" (e"i( i(i# i# #$$" #$$" (+!( (+!( 617 *e $e"e' / A8$?#$ A8$?#$&% &%e' e' #$m%$& #$m%$&n' n' +!e +!e een een *i'e. *i'e. &e' &e' ! !#i'? !#i'?! !e e in'i# in'i#!($ !($" " + ! me(+. "e' e$"e (+e '!. $ (+e %H me(e" in (+e !$"!($"ie/ Di!8$ #$m%$& #$m%$&n' n' !"e !"e !$ !$ &e' &e' e$" e$"e e !
$$ $$' #$$" $$"iin) !)en( )en( , i$ i$$) $)i#! i#! (!inin) !)en( !n' (e=(ie '.e/ One $ (+e !miie $ 'i!8$ #$m%$&n' *i'e. &e' ! '.e i (+e &'!n &'!n// 617 S&'!n '.e !"e ! !mi. $ #$m%$&n' #!e' i%$%+ii# !8$ '.e (+!( +!e een e=(enie. &e' in (+e in'& in'&( (". ". !n' !n' in #ie #ien( n(i i# # "ee! ee!""#+ #$mm #$mm&n &ni( i(ie ie/ / S&'! S&'!n n i #$mm #$mm$n $n. . $&n' in *!=e !n' $i !n' i( +! ! #+!"!#(e"i(i#/ #+!"!#(e"i(i#/ S&'!n '.e *e"e *i'e. &e' &e' ! ! (e=( (e=(i ie e '.e/ '.e/ S&'! S&'!n n '.e, '.e, %!"( %!"(i# i#& &!" !". . S&'! S&'!n? n?1, 1, i !$ !$ &e' &e' e$ e$""e ! ! $$' $$' #$$ #$$"! "!n( n( in #&" #&"". %$*'e" !n' "e' #+ii %!(e, !n' $(+e" !& !e #e +$*e *ee", e", (+e. +e. +!e +!e een een !nne' e#!&e $ (+ei" 67 #!"#in$)eni#i(./ S&'!n? S&'!n?1 1 '.e '.e '$e '$e n$( 'i"e 'i"e#( #(. . $n' $n' *e *e *i(+ *i(+ #$(( #$(($n $n in# in#e e #$(( #$(($n $n !#!#- &n#(i$n! )"$&% #!%!e $ #+emi#! in(e"! in(e"!#(i #(i$n/ $n/ T+&, T+&, &'!n &'!n?1 ?1 '.e '.e !"e !"e 'i"e#(. 'ee$%e' in (+e #$(($n !"i# in $"'e" ($ #$$" i( in ! %"$#e #!e' in)"!in '.ein)/ In)"!in '.ein) em%$. .n(+ei8in) (+e '.e ini'e (+e !"i#/ T+i e=%e"imen( e=%e"imen( $#&e $n (+e .n( .n(+e +ei i $ ! (.%e (.%e $ S&'! S&'!n n '.e, '.e, S&'!n?1 #$mm$n. -n$*n ! C So4ent Yeo2 /9 !n' So4ent O*!n(e R !n' +! ! .(em!(i# n!me $ 1? %+en.!8$?2?n!%+(+$ %+en.!8$?2?n!%+(+$ 657 . em%$.in) 'i!8 i!8$(i8 $(i8! !(i$n (i$n "e!# e!#(i$ (i$n $ !nii niin ne $$* $$*e' e' . (+e 'i!8$n 'i!8$ni&m i&m #$&%i #$&%in) n) "e!#(i$n $ (+e $"me' !"ene'i! !"ene'i!8$ni 8$ni&m &m *i(+ ?n!%+(+ ?n!%+(+$ $ in ! (*$?%$( .n(+ei me(+$'/ I( %"$%e"(. ! ! 'ee$%e' $" in)"!in '.e *i !$ e ine(i)!(e'/ Ai'e "$m (+e %"$% %"$%e" e"(i (ie e $ (+e (+e .n( .n(+e +ei i8e 8e' ' !8$ !8$ #$m% #$m%$& $&n' n',, (+i (+i (&' (&'. . !$ !$ !im !im ($ &n'e"(!n' (+e me#+!nim e+in' (+e .n(+ei .n(+ei "e!#(i$ "e!#(i$n n $ 1?%+en. 1?%+en.!8$?2? !8$?2? n!%+(+$/ 2
METHODOLOGY S&'!n?1 '.e $" 1?%+ ?%+en.!8$?2 $?2? n!%+(+$ *! .n(+ei8e' . em%$. em%$.in) in) (*$?%$ (*$?%$(( .n(+ .n(+ei ei !n' i( %"$% %"$%e" e"(i (ie e ! ! 'ee 'ee$ $%e %e' ' '.e '.e *! *! !$ $ ine ine (i)! (i)!((e' . %e" %e"$" $"min) in)"!in '.ein)/ A. Prepara! Prepara!"# "# "$ rea%e#& rea%e#& T+e nee'e' "e!)en(, "e!)en(, %+en %+en. .'i 'i!8 !8$n $ni& i&m m #+$ #+$"i "i'e 'e !n' !n' ? n!%+(+$ $&(i$n *e"e "( %"e%!"e'/ %"e%!"e'/ P+en.'i!8$ni&m #+$"i'e $&(i$n *! %"e% %"e%!" !"e' e' . mi=i mi=in) n) 0/2 0/2 m !ni !niin ine, e, 0/5 m *!(e" !n' 0/5 m #$n#en("!(e' HC in ! 50?m E"enme.e" !-/ T+e "e&(in) "e&(in) mi=(&"e *! %!#e' in !n i#e? !(+ ($ #$$ i( ($ < C (+en 1 m $ i#e? #$' 'i(ie' *!(e" *! mi=e' ($ i(/ A %!(& %!(&!? !?& & $ N!NO N!NO2 #".(! #".(! *e"e (+en !''e' ($ (+e #$' mi=(&"e !n' i( (em%e" (em%e"!(& !(&"e "e *! m!in( m!in(!in !ine' e' e$* e$* 5 C/ On (+e $(+e" +!n', ?n!%+(+$ $&(i$n *! %"e%!"e' . 'i$in) 0/5 ) ? n!%+(+$ in 5 m 5 !&e$& N!OH $&(i$n in ! 50?m ?m e!-e"/ T+e mi=(&"e *! !$ %!#e' in !n i#e !(+ ($ #$$ i( ($ < C/ B. I#%ra! I#%ra!# # '(e!#% '(e!#% In)" In)"!i !in n '.ei '.ein) n) *! *! %e" %e"$" $"me me' ' . $!-in) ! 2= #m #$(($n !"i# in (+e #$' ?n! ?n!%+(+$ $&(i$n, (i &me")e' in (+e i#e !(+ $" min&(e/ T+e !"i# *! (+en "em$e' !n' %!((e' '". e(*een (e" %!%e"/ T+e !"i# *! ne=( imme"e' in (+e %+en. %+en.'i! 'i!8$n 8$ni&m i&m #+$" #+$"i'e i'e $&( $&(i$n i$n// A(e" (e" 0 min& in&(e, e, (+e !" !"i# i# *! "em$e' "$m (+e $&(i$n !n' i( *! "ine' *e *i(+ "&nnin) *!(e"/ C. S(#)e&!& S(#)e&!& "$ S*'a#-1 S*'a#-1 '(e T+e "em!inin) "em!inin) %+en.'i!8$ni&m %+en.'i!8$ni&m #+$" #+$"i'e i'e $&( $&(i$n i$n *! *! !''e' !''e' $* $*. . *+ie *+ie (i"" (i""in) in) ($ (+e #$' #$' ?n!%+ ?n!%+(+$ (+$
$& $&(i (i$n $n// T+e T+e "e!#( e!#(i$ i$n n mi=( mi=(&" &"e e *! *! (+en (+en !$ !$*e *e' ' ($ (!n (!n' ' !( < C $" 5 min& min&(e (e/ / T+e T+e %"$' %"$' (( $" $"me' *! *! (e"e' (e"e' !n' *!+e' *!+e' (+$"$&)+ (+$"$&)+. . *i(+ m! %$"(i$n $ #$' 'i(ie' *!(e"/ T+e #"&'e %"$'( %"$'( $(!ine' *! "e#" e#".(! .(!i8e' i8e' . %e" %e"$"m $"min) in) +$( +$( (" ("!( !(i$ i$n n !n' !n' &in &in) ) e(+! e(+!n$ n$ ! (+e (+e $en( $ "e#".(!i8!(i$n/ T+e e(?&% &e' &e' in +$( ("! ("!(i$ (i$n n i i& i&("! ("!(e' (e' in Fi)&"e e$*/
Fi)&"e / H$( ("!(i$n e(?&% T+e $(!ine' "e#".(!i8e' "e#".(!i8e' %"$'( *! %!#e' in ! %"e?*ei)+e' i! ($ 'e(e"mine i( *ei)+( !n' (+e %e"# %e"#en en(! (!)e )e .ie .ie' ' $ (+e (+e .n( .n(+e +ei i/ / Sm! Sm! !m$&n( !m$&n( $ (+e "e#" "e#".( .(! !i8e i8e' ' %"$'( *e"e &e#(e' in (+e me(in) %$in( 'e(e"min!(i$n/ T+e e(?&% &e' $" (+e me(in) %$in( 'e(e"min!(i$n $ (+e .n(+ei8e' S&'!n?1 '.e i +$*n in Fi)&"e < e$*: e $*:
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Fi)&"e Me(in) %$in( 'e(e"min!(i$n e(?&% RESULTS AND DISCUSSION A. I#%ra! I#%ra!# # '(e!# '(e!#% % S&'!n '.e $" 1?%+en.!8$?2?n!%+(+$ #!nn$( 'i"e#(. $n' *e *i(+ #$(($n !"i# !"i# + + (+!( (+!( in $"'e" $"'e" ($ e#$m e#$me e &e& ! ! '.e, i( m&( e in)"!ine' $" 'i" 'i"e#( e#(. . .n( .n(+e +ei i8e 8e' ' ini ini'e 'e (+e (+e !"i#/ !"i#/ T+e %+en.'i %+en.'i!8$n !8$ni&m i&m i$n *! "( %"e%!"e' . "e!#(in) !niine *i(+ N!NO2 #".(! in (+e %"een#e $ !n !#i' !#i'// S$'i S$'i&m &m ni(" ni("i( i(e e !n' !n' HC HC *e" *e"e !''e' !''e' ($ %"$' %"$'e e ni("$ ni("$!( !(in) in) !)en( !)en(,, %e#i#!., ! ni("$. #!(i$n *+i#+ in (&"n (&"n *i *i "e!#( e!#( *i(+ *i(+ !ni !niin ine e ($ .ie .ie' ' %+en.'i!8$ni&m i$n/ T+e me#+!nim ?H O +$*n $" (+eH O.n(+e .n(+ei i H "e!#( "e i$n i +$*n O !#(i$n e$* in Fi)&"e 5/
2
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34
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Fi)&"e 5/ Me#+!nim $" (+e 'i!8$(i8!(i$n "e!#(i$n
Ni("$. #!(i$n 3 >N@O4 *+i#+ *i e"e ! (+e in#$m in#$min) in) ee#( ee#("$ "$%+ %+ie ie $" (+e "e!# "e!#(i$ (i$n n *i(+ *i(+ !niin !niine, e, i "( "( $"me $"me' ' "$m (+e !''e' "e!#(!n(, N!NO 2 !n' HC 3!4/ 3!4/ T+e ni( ni("$. $. #!(i$ !(i$n n (+en (+en !((!#- (+e !i# ni("$)en $ !niine ($ $"m ! #+!")e' %e#ie 3<4 *+i#+ *i (+en (!ii8e i(e . $in) ! %"$($n 354/ T+e ne&("! %e#ie $"me' 354 $" N?ni("$$!mine (+en (!&($me"i8e ($ ! 'i!8$+.'"$=i'e 3J4 in ! imi!" !+i$n ! -e($?en$ e($?en$ (!&($m (!&($me"i e"i8!( 8!(i$n i$n 67/ T+e +.'"$=i +.'"$=i'e 'e )"$&% )"$&% i (+en !((!#-e' !((!#-e' . !n ee#("$%+ie, H >, ($ .ie' ! #+!")e' %e#ie 34 *i(+ ! )$$' e!in) )"$&% 3?OH24/ T+e ni("$)en in (+e NOH 2 $n' *i '$n!(e i( ee#("$n ($ $=.)en in $"'e" $" (+e )"$&% ($ e!e )iin) ! %$i %$i(i (ie e. . #+!" #+!")e )e ($ (+e (+e ni(" ni("$) $)en en// e#!&e $ (+e %"een#e $ (+e 'e$#! 'e$#!i8 i8e' e' %i ee#(" ee#("$n $n, , (+e (+e #+!" #+!")e )e *i *i 'i("i 'i("i& &(e (e i(e i(e ($ "e& "e&(( ($ (+e (+e !"i$& "e$n!n#e $"m $ (+e in(e"me'i!(e 3#4 (+en )iin) (+e n! %"$' %"$' (, (, (+e (+e %+en %+en. .'i 'i!8 !8$n $ni& i&m m i$n/ i$n/ Re$n!n#e e$n!n#e $ (+e in(e"me in(e"me'i!( 'i!(e e (!(e (!(e e=%!in (+e )"e!( (!ii(. $ !"en !"ene' e'i! i!8$ 8$ni ni&m &m !( !( #$m% #$m%!" !"e' e' ($ !-! -!ne' ne'i!8 i!8$ni& $ni&m m (+! (+!( #!nn #!nn$ $( e i$!(e'/ H$*ee", (+e ni("$)en )"$&% 3N;N 3N;N44 $ !n. !n. 'i!8 'i!8$n $ni& i&m m i ! )$$' )$$' e!in) )"$&%, !n' ! + %+en.'i %+en.'i!8$n !8$ni&m i&m #!n !$ 'i$#i!( 'i$#i!(e e in($ in($ ni("$ ni("$)en )en !n' !n' !"ene !"ene #!"$# #!"$#!(i !(i$n $n *+i#+ in (&"n #!n !$ "e!#( ($ .ie' &n'ei"!e &n'ei"!e %"$'(/ %"$'(/ F"$m (+e (+e !"ene #!"$#!(i$n, (+e 'e#$m%$e' %+en. %+en.'i! 'i!8$n 8$ni&m i&m #!n .ie' .ie' 'ie" 'ie"en( en( -in' $ &(i(&(e' en8ene %"$'( <
+ ! #+$"$en8ene "$m (+e "ee #+$"i'e i$n in (+e $&(i$n !n' %+en$ . !''i(i$n $ *!(e" in (+e !"$m!(i# #!(i #!(i$ $n/ T+ee ee i'e "e!#( e!#(ii$n $n !"e i&("!(e' in Fi)&"e J/
Fi)&"e J/ Si'e "e!#(i$n $ T+e"e$"e, T+e"e$"e, (+e "e&(in) "e&(in) "e!#(i$n %+en %+en. .'i 'i!8 !8$n $ni& i&m m i$n i$n .ie .ie'i 'in) n) mi=(&"e *! -e%( !( ! (em%e"!(&"e $ %+en$ !n' #+$"$en8ene <C in $"'e" ($ %"een( 'e#$m%$i(i$n $ (+e $"me' $"me' %+en. %+en.'i! 'i!8$n 8$ni&m i&m i$n i$n !n' $"m!( $"m!(i$n i$n $ !n. i'e i'e %"$'& %"$'( #( (+!( (+!( *i i 'e#" 'e#"e! e!e e (+e (+e .ie .ie' ' $ (+e (+e .n(+ei/ On (+e $(+e" +!n', i (+e .n(+ei $ (+e (+e %+en %+en. .'i 'i!8 !8$n $ni& i&m m i$n i$n i +e' +e' !( !-!ine !-!ine me'i&m, me'i&m, (+e 'i!8$ni&m 'i!8$ni&m !( *i "e!#( *i(+ OH ? !( +i)+ #$n# #$n#en en(" ("! !(i$ (i$n in (+e (+e $&(i &(i$ $n ($ %"$' %"$' e e (+e (+e "e!( e!(i ie e. . &n" &n"e!#( e!#(i ie e 'i!8$+.' 'i!8$+.'"$ "$=i'e =i'e ! +$*n +$*n in Fi)&"e i)&"e e$*/
67
Fi)&"e / Di!8$+.'"$=i'e Di!8$+.'"$=i'e $"m!(i$n "$m 'i!8$ni&m !( !( +i)+ %H me'i&m T+e $"me' %+en.'i!8$ni&m *i (+en &n'e &n'e") ")$ $ #$&% #$&%i in) n) "e!# "e!#(i (i$n $n *i(+ *i(+ ? n!%+(+$/ T+e ?n!%+(+$ $&(i$n *! %"e% %"e%!" !"e' e' . 'i 'i$ $i in) n) ?n! ?n!%+ %+(+ (+$ $ #".(! in 5 !&e$& N!OH $&(i$n/ T+i i '$ne e#!&e (+e #$&%in) "e!#( e!#(i$ i$n n $##& $##&" " "!%i "!%i' '. . !( i) i)+( +(. . !-!ine #$n'i(i$n/ T+e !i#i(. $ (+e me'i&m, e%e#i!. (+e %"een#e $ OH?, !$* (+e !((!#-in) ne$%+ie, ?n! ?n!%+ %+(+ (+$ $,, ($ e &"( &"(+e +e"" !#(i !#(i! !(e (e' ' (+& "e'in) (+e !#(i!(i$n ene"). $
(+e "e!#(i$n !n' )iin) ! !(e" "!(e $ #$&% #$&%i in) n) "e!#( e!#(i$ i$n n 67/ H$ H$*e *ee e", ", i ? n!%+ n!%+(+ (+$ $ i 'i$ i$ e' e' in !n !#i' !#i'i# i# me'i&m, me'i&m, (+e %"een# %"een#e e $ +.'"$ni& +.'"$ni&m m i$n *i 'e!#(i!(e (+e "in) m!-in) i( e "e!#(ie ! ! ne$%+ie e#!&e (+e %$i(ie. #+!")e' +.'"$ni&m i$n (en' ($ en#$e (+e %!"(i!. ne)!(ie #+!")e' ?n!%+(+$/ T+&, (+e "!(e $ "e!#(i$n e#$me $*e"/ T+e #$(($n !"i# ($ e '.e' i $!-e' in (+e (+e #$' #$' ?n! ?n!%+ %+(+ (+$ $ $& $&(i (i$n $n !n' !n' !(e"*!"', (+e !"i# i (+en imme imme" "e' e' in (+e (+e %+en %+en. .'i 'i!8 !8$n $ni& i&m m #+$"i'e $&(i$n in $"'e" ($ .n(+ei8e S&'! S&'!n? n?II 'i" 'i"e#( e#(. . in (+e (+e !" !"i# i#// T+e T+e !"i# (&"n "e'?$" ?$"!n)e in #$$" im%.in) (+!( (+e 'ei"e' S&'!n?1 '.e i .n(+ei8e'/ T+e #$$" $ (+e '.e' !"i# *i n$( !$ e "em$e' *+en (+e !"i# i *!+e' in#e (+e !8$ '.e m$e# m$e#&e &e !"e !"e !"e!' !"e!'. . een een ((- in (+e !"i#/ In (+e #!e $ (+e #$(($n !"i#, in)"!in '.ein) i m$"e %"ee"!e (+!n 'i"e#( '.ein) &in) S&'!n?I '.e/ C$(($n e" i m$( $(. #$m%$ %$e' $ #e& e&$ $ e 3Fi)&"e4 , !n' $$-in) !( (+e ("(&"e $ #e #e& &$ $e, e, i( +! +! n$ %$! %$!"i "i8! 8! e e )"$& )"$&% % (+!( (+!( #!n #!n $" $"m ("$ ("$n) n) $n' $n' *i(+ i$n !n' *i(+ ! i) m$e#&e + ! S&'! S&'!n? n?I/ I/ T+& T+&,, *+en *+en (+e (+e 'i" 'i"e#( e#( me(+$' i &e', (+e '.e *i e e!i. *!+e' !*!. m!-in) i( e %"ee"!e/
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#$in #$in#i #i'e 'e *i(+ *i(+ (+e (+e %"$% %"$%e" e"(. (. $ (+e (+e S&'!n? S&'!n?1 1 '.e ein) ein) "e' "e' in #$$" #$$"// T+e #$$ #$$"" $ (+e (+e S&'! S&'!n? n?1 1 i '&e '&e ($ (+e (+e +i)+. +i)+. #$n&)!( #$n&)!(e' e' .(em .(em #!%!e #!%!e $ !$"in) i)+( in (+e iie %e#("&m/ T+e $(!ine' %e"#en(!)e %e"#en(!)e .ie' i 1/< 1/< im% im%.i .in) n) (+!( (+!( (+e (+e .n( .n(+e +ei i "e!#(i$n m!. +!e !$ een !e#(e' . $(+e" $(+e" i'e "e!#(i$n "e!#(i$n %"een(e' %"een(e' in (+e "e& "e&( ( !n' 'i#& 'i#&i i$n/ $n/ T+e T+e n! n! %"$'& %"$'( #( i !$ !$ &e# &e#(e' (e' &n'e" &n'e" (+e me(in) %$in( 'e(e"min!(i$n e(?&% ($ ! !e e (+e (+e %&"i( &"i(. . $ (+e '.e/ '.e/ T+e e=%e" e=%e"ime imen(! n(! me(in me(in) ) %$in( %$in( i 10C *+i *+ie e (+e (+e (+e$ (+e$""e(i# e(i#! ! i 11 11 C/ T+e T+e #$ #$en ene e $ (+e (+e !& !&e e $(! $(!in ine' e' im%i im%ie e (+!( (+!( (+e %"$' %"$'( ( $(!i $(!ine' ne' i ne!". %&"e !n' ! +, (+e e""$" (+!( )ie ! e". $* %e"#en(!)e .ie' m!. +!e een $n. '&e ($ me!&"emen( !n' in("&men(! e""$"/ REFERENCES
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M#M&""., / 32004/ O")!ni# Ch!%te* 19: C+emi(". C+emi (". (+ e' e'/ Ch!%te* A$ines !n' Hete*o#y#es / "$$-C$e, Cen)!)e Le!"nin): em$n(, %)/ 1J?<5
627 Re!ne, R/, Lei($, I/, &"#+en-$, S/ He"$'e, K/ 2010/ A *e4ie2 o !n!yti#! te#hni;&es o* 'ete 'ete*$ *$in in!t !tio ion n o S&'! S&'!n n I
6<7 F"i)e" "i)e"i$, i$, N/A/ N/A/ 133/ The #o&%in( o 'i!" 'i!"on oni& i&$ $ s!t s!ts. s. =. Che$ Che$.. E'. 45, 1<2?1< 6<7 Gii, R/ G/ 164/ The $e#h!nis$ o 'i!"oti"!tion. =. Che$. E' / 51, <
De%!"(men( $ C+emi(". C+& C+&!$ !$n) n)-$"n Unie" ie" i(. i(./ S.n(+ei $ S&'!n?IV/ 6Onine7/ Re("iee' "$m: +((%:***/#+emi("./#/#+&!/! #/(+!#O")20C+em 20L!_2012E=%/11617/%' 3!##ee' A%"i 2, 20154
6J7 C!"e., / 3200J4/ O")!ni# C+emi(". Ch!%te te** 11: 11: A$ A$in ines es/ J (+ e' e'/ Ch!% M#G" M#G"!* !*Hi Hi ?C ?C$m $m%! %!ni nie e:: Ne* Ne * $"-, $"-, %%?5?/ 67 S$$m S$$m$n $n,, G/ T/ Q/, F".+e, ".+e, C/ 320114/ O")!ni# C+emi(". 10(+ e'i(i$n/ $+n Qie. S$n In#/: USA 67 O-!n$, M O)!(!, / 165/ >ineti#s o the Di!"oti"!tion o Aniine. =. Che$. E' / 6, %%? 515?51/
I7a%e S"*r8e&
6!7+((%:***/&/e'&/!&_S#+$$_S#ien 6!7+((%:***/&/e'&/!&_S#+$$_S#ien #e_Le$n1J/#+/GIF 67+((%:***/e%!n(#ien#e/#$min'e= 67+((%:***/e%!n(#ien#e/#$min'e= 'e!nim!)e1/1/%) 6#7+((%:***/$")!ni#? #+emi("./$")n!me'"e!#(i$n' i!8$(i!(i$n/+(m
10
APPENDI9
C!#&!(i$n $ Pe"#en(!)e ie' wt of vial vial with with pdct pdct −wt of empty vial=16.19 g− 16.209 g =0.01 g : wt of Sudan Sudan−1 obtained
0.35 g of
β −naphthol x
0.20 mlof
aniline x
248.28 g of
Sudan Sudan−1 =0.602 g suda sudan n 1=theo yield 144.17 gof β − naphthol
1.02 g
mlaniline
x
248.28 gof
Sudan −1 = 0.544 gof sudan −1=theo yield =¿ Ther Theref efor or e , anili anilineis neis aniline 93.13 g aniline
A#(&! .ie': 0.01 g amt of Sudan Sudan−1 obtained .84 : Percentage x 100 = x 100 =1 .84 Percentage yield theore theoretica ticall amt of Sudan −1 yield 0.544 g