synthesis of important dyes

8/18/2019 Synthesis of Important Dyes

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SYNTHESIS OF IMPORTANT DYES

BY: 14BCH06114BCH062

14BCH063

14BCH064

14BCH065


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INTRODUCTIONWhat is a dye?

A !"!#ed s$%sta&e ha'i&( a)&ity t!*a#ds s$%st#ate+

,ai& -$&ti!& !- dye:. T! i/a#t !"!# t! %#e !&e#/a&e&t %asis+

It !&sists !- 2 /ai& !/!&e&ts+ They a#eCh#!/!h!#es a&d A$!h#!/es+

C!/!$&d !&tai&i&( h#!/!h!#es is a""ed

h#!/!(e&+A$!h#!/es e#-!#/s 2 /ai& -$&ti!&s: /!di-yi&(

!"!# i&te&sity a&d i&( h#!/!(e& !& -a%#is+


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!/e i/!#ta&t

Ch#!/!h!#es


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!/e i/!#ta&t A$!h#!/es


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A"ia#i& Dye


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TRUCTUR


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Che/ia" a&d hysia" #!e#tiesIUAC Na/e: 172.dihyd#!y.8710.

a&th#ae&edi!&e

Othe# Na/es: 172.dihyd#!ya&th#a9$i&!&e7 T$#ey #ed7 ,!#da&t #ed 117 A"ia#i& #ed+

Che/ia" ;!#/$"a: C14H


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y&thesis !- A"ia#i&


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A"iati!&s !- A"ia#i&It is $sed as a H i&diat!#+

It is $sed as a %i!"!(ia" stai&+ It is *ide"y

$sed t! stai& a"i$/ i& %!&es a&d i& !the#tiss$es+

It is $sed i& /edia" sie&e -!# the st$dy !-%!&e (#!*th7 %!&e /a##!*7 !ste!!#!sis a&d

(e&eti e&(i&ee#i&(+It is $sed as a i(/e&t i& ai&t i&d$st#y+


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It is a dye *hih e/its !"!# *he& eited*ith a "i(ht s!$#e !- s$)ie&t *a'e"e&(th+

Tyes !- @$!#ese&t dyes a#e:.1 A#idi&e dyes

2 Cya&i&e dyes

3 ;"$!#!&e dyes

4 Oai&e dyes5 he&a&th#idi&e dyes

6 Rh!da/i&e dyes


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U&i9$e -eat$#es !- ;"$!#ese&tDyes

Hi(h *ate# s!"$%"e

Hi(h"y deteta%"e s!/e e'e& %e"!* 1 a#te# t#i""i!&

t#e/e"y "!* t!iity #ati&(s

Hi(h !"!$# st#e&(th

e""e&t -ast&ess #!e#ties

Dis"ays (!!d sta%i"ity


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;"$!#esei& Dye


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t#$t$#e


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Che/ia" a&d hysia" #!e#tiesIUAC Na/e:. 376.

dihyd#!ysi#!is!%e&!-$#a&.13H78.8HEFa&the&E.3.!&e

Othe# &a/es: Res!#i&!"htha"ei&7 s!"'e&tye""!* 847 A&(i!@$!#7 Gaa& ye""!* 2017 s!aye""!*

Che/ia" -!#/$"a: C20H12O5 ,!"a# /ass: 332+31 (=/!"

,e"ti&( !i&t: 314. 316 C

De&sity: 1+602 (=/


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y&thesis !- ;"$!#esie&


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A"iati!&s !-

;"$!#esie&It is $sed -!# #a deteti!& +

It is $sed i& -!#e&si "a%!#at!#y t! detet %"!!dstai&s+

It is $sed i& dye "ase#+

Its s!di$/ sa"t is a""ed U#a&i&e a&d eye d!t!#s$se it t! di"ate thei# atie&ts $i"s+

It is $sed t! dye !tt!& a&d *!!"+

;"$!#esei& is a"s! $sed as a -!!d dye7 i& *hih it(!es %y the &a/e Ye""!* N!+ >+

It is a"s! $sed t! dye d#$(s7 !s/etis a&d /a#e#s+


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zo Dye

A! dyes !/!$&ds that !&tai& twoaromatic fragments !&&eted %y a N=N d!$%"e %!&d+

A! dyes a#e #ea#ed i& a two stepreaction+

The #st %ei&( the sy&thesis !- a& Aromatic

diazonium ion -#!/ a& a&i"i&e de#i'ati'e+ The &et ste is !$"i&( !- the diazonium

salt *ith a& a#!/ati !/!$&d+


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;i#st ste:

Resonance


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;e* I/!#ta&t !i&tshe&y" a/i&e #eats *ith a s!"$ti!& !- s!di$/&it#ate a&d hyd#!h"!#i aid at a te/e#at$#e%e"!* 5!C t! #!d$e %e&e&e dia!&i$/

h"!#ide+ This tye !- #eati!& is &!*& as diazotization+

I- the te/e#at$#e is a""!*ed t! #ise a%!'e5oC7 the %e&e&edia!&i$/ h"!#ide

de!/!ses t! -!#/ phenol a&d nitrogengas is (i'e& !J+


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e!&d te: Attah *ith

s$ita%"e K#!$s

A&i"i&e


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Malachite Green

Dye


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t#$t$#e

IUAC Na/e:. 4.L4.di/ethy"a/i&!he&y"E he&y"/ethy"ide&eM. N7.di/ethy"y"!hea.275.die&.1.i/i&i$/ h"!#ide


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Che/ia" a&d hysia" #!e#ties,!"e$"a# -!#/$"a:. C23H25C"N2

,!"e$"a# Wei(ht:. 364+811 (=/!"

C!"!#:. K#ee& #ysta"s *ith /eta""i "$ste#

!"$%i"ity:. I& A"!h!" 'e#y /$h s!"$%"e

I& *ate# 4 /(= at 25 C

a!# #ess$#e:. 13 // H( at 25 C

H:. 1P s!"$%"e i& *ate#7 1+4,a a%s!#ti!&:. 616+8 &/

O& heati&( Q it e/its 'e#y t!i (as Nit#!(e& Oidea&d HC"


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;!#/ati!& 1 The "$! -!#/ !d /a"ahite (#ee& *as #st #ea#ed %yHa#/a&& ;ishe# i& 1> %y !&de&si&( enzaldehyde a&ddimethyalaniline i& the /!"e$# #ati! 1:2 i& the #ese&s !-$"-$#i Aid+

C6H5CHO 2 C6H5NCH32 C6H5CHC6H4NCH322 H2O

This !"!#"ess luco !/!$&d 7 a #e"ati'e !-

t#ihe&y"/etha&e7 is !idied t! ati!& that is ,a"ahiteK#ee&+

C6H5CHC6H4NCH322 HC" 1=2 O2

C6H5CC6H4NCH322EC" H2O


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,eha&is/


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;!#/ati!& 2

,a"ahite K#ee& *i"" %e -!#/ed %y #eati!&%et*ee& p!dimethyl aminophenylmagnesium romide a&d methylenzoate+


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A"iati!&,ai&"y $sed as a Dye+

As a a&ti%ate#ia"+

As a a&ti-$&(iide+,K has -#e9$e&t"y %ee& $sed t! ath thie'es

a&d i"-e#e#s+ The %ait7 $s$a""y /!&ey7 iss#i&"ed *ith the a&hyd#!$s !*de#+ A&y!&e

ha&d"i&( the !&ta/i&ated /!&ey *i"" &dthat !& $!& *ashi&( the ha&ds7 a (#ee& stai&!& the si& that "asts -!# se'e#a" days *i""#es$"t+


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Crystal "iolet

Dye


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t#$t$#e

IUAC Na/e:. T#is4.

di/ethy"a/i&! he&y"


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Che/ia" a&d hysia" #!e#ties,!"e$"a# -!#/$"a:. C25H30C"N3

,!"e$"a# Wei(ht:.

40>+8>8 (=/!"

,e"ti&( !i&t:. 205 C 401 ; 4>< V


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;!#/ati!& 1We a& #ea#ed this dye %y !&de&sati!& !-formaldehyde a&d dimethyalaniline t! (i'e a"$! dye+

CH2O 3 C6H5NCH32 CHC6H4NCH323 H2O

This !"!#"ess !/!$&d is !idied t! the !"!#ed

ati!&i -!#/+

CHC6H4NCH323 HC" 1=2 O2

CC6H4NCH323EC" H2O


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;!#/ati!& 2

C#ysta" 'i!"et *i"" %e -!#/ed %y #eati!&%et*ee& p!dimethylaminophenylmagnesium romide a&d ethyl

enzoate+


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,CHANI,: .


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A"iati!&sUsed t! dye ae#

As a !/!&e&t !- &a'y %"$e a&d %"a i&s-!# #i&ti&(7 %a"" !i&t e& a&d i& et #i&te#s+

A"s! $sed t! !"!#ie di'e#se #!d$ts s$h as-e#ti"ie#s7 a&ti-#eees7 dete#(e&ts7 a&d"eathe#+

It has a&ti%ate#ia"7 a&ti-$&(a"7 a&tihe"/i&thi7a&tit#ya&!s!/a"7 a&tia&(i!(e&i7 a&da&tit$/!# #!e#ties+


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BT #i!h#!/e

B"a TDye


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t#$t$#e

#e-e##ed IUAC Na/e:.!di$/ 1.1.Hyd#!y&ahthy"a!E.6.&it#!.2.&ahth 4.s$"-!&ate

yste/ati IUAC Na/e:.!di$/ 4.2.1.hyd#!y&ahtha"e&.2.y"hyd#ai&.1

y"ide&eE.>.&it#!.3.!!.374.dihyd#!&ahtha"e&e. s$"-!&ate


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3<

y&thesis !-#i!h#!/e B"a.T


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A"iati!&It is $sed as a& i&diat!# i& DTA t#itai!&+#i!h#!/e B"a T has a"s! %ee& $sed t!

detet the #ese&e !- #a#e ea#th /eta"s+


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BI,ARCV BROWN DY


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TRUCTUR


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RORTICH,ICA ;OR,UA. C21H24N<

,!"a# /ass Q 3


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YNTHI O; BI,ARCV BROWN

DY


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AICATIONUD IN HITOOKY ;OR TAININK TIU

HO OIH+

DYINK WOO AND COTTON COTH+


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,THY ORANK


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TRUCTUR


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RORTICH,ICA ;OR,UA . C14H14N3NaO3

,OAR ,A Q 32>+33 (/=/!"

,TINK OINT Q X 300 CNTRIKRADOUBIITY IN WATR Q 0+5 K,= 100 ,


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YNTHI O; ,THY ORANK


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AICATION,AINY UD A H INDICATOR

IT I FTR,Y COOURD CO,OUNDUD IN DYINK

AO UD IN RINTINK TFTI+


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,ORDRANT DY+ This dyes #e9$i#e a /!#da&t -!# a"iati!& asa dye+

Dye !& !/%i&( *ith a /!#da&t i/a#tsi&s!"$%"e !"!# !& s$%st#ates+

,!st !//!&"y $sed /!#da&t dyes a#e Q

He/atei&&at$#a" %"a 17#ih#!/e ya&i&/!#da&t %"$e a&d a"ia#i& #ed/!#da&t #ed3+


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sse&tia" -eat$#es !- /!#d#a&t

dyes+,!st"y they !&tai& hyd#!y"s a&d a#%!y"

(#!$+

They e&s$#e "i(ht a&d *ash -ast&ess+

Has a%i"ity t! %#i(hte& ha&(e s!/e dye !"!#+

#e'e&t !"!# %"eedi&(+


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I&di(! Dye

Hist!#y:

The &a/e #ND#G$ !/es -#!/ the K#ee te#/ I&di!&7 *hih /ea&s a #!d$t!- I&dia+

I&di(!7 !# i&di(!ti&7 is a dyest$J !#i(i&a""y et#ated -#!/ the 'a#ieties !- thei&di(! a&d *!!d "a&ts it has %ee& -!$&d i& A-#ia7 I&dia7 I&d!&esia7 a&d Chi&a+

I&di(! *as hi(h"y #ied !//!dity !& the si" #!$te a&d i& 18th e&t$#yBe&(a" *as the %i((est #!d$e# !- i&di(! i& the *!#"d+


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N!* as the#e is !&t#!""ed s$"y !- i&di(!7 he/ists %e(a&

sea#hi&( -!# sy&theti /eth!ds !- #!d$i&( the dye+

"a&ts s$h as #ndigo tinctoria a&d #ndigofera a#e the /!st!//!&+ I& a&ie&t ti/es7 i&di(! *as#ei!$s !//!dity %ea$se "a&t "ea'es !&tai& !&"y a%!$ts/a"" a/!$&t !- the dye a%!$t 2.4P+

The#e-!#e7 a "a#(e &$/%e# !- "a&ts

a#e #e9$i#ed t! #!d$e a

si(&ia&t 9$a&tity !- dye+


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The ,a&$-at$#i&( #!ess

Nat$#a" et#ati!&:

1+ "a&t et#ati!& !- i&di(! #e9$i#es se'e#a" stes+

. The he/ia" -!$&d i& "a&t "ea'es is i&dia& a&d it is !&'e#ted it

t! i&di(! a&d the #!ess has #e/ai&ed $&ha&(ed -!# th!$sa&ds!- yea#s+

.I& this #!ess7 a se#ies !- ta&s a#e a##a&(ed i& a ste *ise -ashi!&+ The $e#./!st ta& is a -e#/e&tati!& 'esse" i&t! *hih the -#esh"y$t "a&ts a#e "aed+

.A& e&y/e &!*& as i&di/$"si& is added t! hyd#!"ye7 !# %#ead!*&7 the i&dia& i&t! i&d!y" a&d ("$!se+ D$#i&( this #!essa#%!& di!ide is (i'e& !J a&d the /it$#e i& the ta& t$#&s a/$#y ye""!*+


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A-te# a%!$t 14 h!$#s7 the #es$"ti&( "i9$id is d#ai&ed i&t! ase!&d ta&+ He#e7 the i&d!y" #ih /it$#e is sti##ed *ithadd"es t! /i it *ith ai#+

This a""!*s the ai# t! !idie the i&d!y" t! i&di(!ti&7

*hih sett"es t! the %!tt!/ !- the ta&+ The $e# "aye#!- "i9$id is sih!&ed a*ay a&d the sett"ed i(/e&t ist#a&s-e##ed t! a thi#d ta& *he#e it is heated t! st! the-e#/e&tati!& #!ess+

The #es$"ta&t /it$#e is "te#ed t! #e/!'e i/$#ities a&dd#ied t! -!#/ a thi i&di(! aste+


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y&theti #!d$ti!&

He#e the sy&thesis #eati!&s a#e !&d$ted i& "a#(estai&"ess stee" !# ("ass #eati!& 'esse"s+

These 'esse"s a#e e9$ied *ith aets t! a""!* stea/ !#!"d *ate# t! @!* a#!$&d the %ath as the #eati!&s#!(#ess+

Bea$se !- the !/"eity !- these he/ia" #!esses7 thedye is $s$a""y /ade i& %ath 9$a&tities+

H!*e'e#7 &!* /eth!ds i&'e&ted -!# !&ti&$!$s #!ess/a&$-at$#i&(+


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1+ ,!#e e)ie&t7 sy&thesis $ti"ies a&th#a&i"i aid+

. This #!ess *as !$"a# *ith /a!# /a&$-at$#e#s7s$h as BA; a&d H!ehst7 -!# !'e# 30 yea#s+

. He#e I&di(! is !%tai&ed -#!/ a&th#a&i"i aid a&dh"!#!aeti aid+

. He#e *e (et N.he&y"("yi&e.!.a#%!y"i aid7i&d!y"i aid7 a&d i&d!y" as a& i&te#/ediate as

sh!*& i& the ($#e+


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2+ C$##e&t"y $sed /eth!d is %y t#eati&( N.he&y"("yi&e *ith

a /!"te& /it$#e !- s!di$/ hyd#!ide7 !tassi$/hyd#!ide7 a&d s!di$/ a/ide+ This hi(h"y se&siti'e /e"t#!d$es i&d!y" at 200C+ *hih is s$%se9$e&t"y !idiedi& ai# t! -!#/ i&di(!.

A-te# the #!ess is !/"ete7 the &ished dye is *ashedt! #e/!'e i/$#ities a&d the& d#ied+


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A"iati!&s The #i/a#y $se -!# i&di(! is as a dye -!# !tt!& ya#&7 *hihis /ai&"y -!# the #!d$ti!& !- de&i/ "!th -!# %"$e ea&s+

He#e -!# a ai# !- t#!$se#s #e9$i#es 3.12 ( !- i&di(!+

It is a"s! $sed as a -!!d !"!#a&t+

;!# t#eat/e&t -!# i""s i&"$di&( s!#i!& %ites a&d st!/ah

a&e#+


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$"-$# Dyes$"h$# dyes a#e s! a""ed %ea$se s$"h$# dye !&tai&

dis$"hide s.s "i&a(e i& thei# he/ia" st#$t$#e+

$"h$# %"a is /!st i/!#ta&t "ass !- s$"h$# dyes+

C!//e#ia""y s$ess-$" %"a s$"h$# *as #st #ea#edi& 1


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Che/ia" t#$t$#e This dye is -!#/ed s$"h$#isati!& !- !#(a&i i&te#/ediates!&tai&i&( &it#! a&d a/i&! (#!$s7 B$t sti"" theeat he/ia" st#$t$#e !- s$"h$# dyes is &!t &!*&+


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%roperties of Sulfur Dyes

These a#e *ate# i&s!"$%"e dyes a&d ha'e &! a)&ity -!# thee""$"!sis as s$h+

B$t s!"$%i"ised *he& t#eated *ith a *ea a"a"i&e s!"$ti!& !-

s!di$/ s$"hide !# a&y !the# #ed$i&( a(e&t t! -!#/ a "e$!!/!$&d+

They a#e a%s!#%ed !& the %e# s$#-ae+

These "e$! !/!$&ds a#e *ate# s!"$%"e a&d ha'e a)&ity -!# the

e""$"!si /ate#ia"s s$h as !tt!& 7 $te+

A&d *he& !idied %y s$ita%"e !idii&( a(e&ts 7 (!t !&'e#ted i&t!i&s!"$%"e dye+


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Dyei&( The dye s!"$ti!& is the& added th#!$(h a "te# "!th

s"!*"y !'e# 15.25 /i&$tes at 40.50 !C7 the& te/e#at$#eis #aised t! 60 !C

"et#!"yte a&d the sa"t is added dee&di&( !& shade %$th!*e'e# a /ai/$/ 9$a&tity d!es &!t eeed /!#etha& 15 (#a/ e# "ite#+

The te/e#at$#e is the& #aised t! a%!'e


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,a&y #!%"e/s taes "ae d$#i&( dyei&( s$h as.

Te&de#i&(: ,ea&s "!ss !# de(#adati!& !- e""$"!si /ate#ia"*ith ti/e+

It is d$e t! -!#/ati!& !- aid -#!/ -#ee s$"h$# #ese&t i& dye%y ati!& !- /!ist$#e !# ai#+

This a& %e (i'i&( t#eat/e&t *ith aid &e$t#a"ii&( a(e&ts$h as s!di$/ aetate+ It !&'e#ts ha#/-$" s$"h$#i aid t!ha#/"ess aeti aid+

B#!&i&ess: $"h$# has a te&de&y t! sh!* %#!&e !"!$#+

This a& %e s!"'ed %y $si&( s$)ie&t #ed$i&( a(e&t "ies!di$/ s$"hide a&d #!'idi&( %ette# !idati!&+


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A"iati!&s$"h$# B"a is a& i/!#ta&t dye !- this "ass+

It dyes a"" the e""$"!se %e# %$t a#ti$"a#"y "i&e& a&d $te t! dee %"a !"!$#+

,ai& ad'a&ta(e !- $si&( it is that s$"h$# dye is heaa&d easy t! a"y+

$"-$# dyes a#e !//!&"y $sed -!# %"a7 %"$e7 %#!*&7hai a&d (#ee& !"!#s+

C!&s$/ti!& !i&t !-


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C!&s$/ti!& !i&t !-'ie*


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A(#i$"t$#e I&d$st#y#i/a#i"y the#e a#e th#ee /ai& tyes !-a(#i$"t$#a" i&d$st#ies that $ses the dye+ They a#ethe crop protection industry7 fertilizer

industry a&d the seed dressing industry+ The$#!se !- the dye $sed he#e is -!# !"!$#i&( !-a(#i$"t$#a" he/ia"s !# i& the ide&tiati!&#!ess !- a(#i$"t$#a" he/ia"s+ The %asise"eti!& #ite#ia dee&ds $!& the -!""!*i&(:.

Dye !"!$#

C!"!$# sta%i"ity

!/ati%i"ity !- the dye *ith the a#ti$"a# a(e&t


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C!s/eti I&d$st#yDyes ha'e -!$&d a *ide 'a#iety !- $ses i& the!s/etis i&d$st#y+ Be it the hair dyes !#lipstic&s !# nail polish' shampoo

e'e#y*he#e the#e is *ide $se !- dyesDyes a#e $sed i& /ai&( !- hai# dye+ The dye

he/ia"s that a#e $sed $s$a""y !&sists !-a/i&! !/!$&ds7 "ie (!amino!)!

hydro*ytoluene a&d /.A/i&!he&!"+


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Heat T#a&s-e# #i&ti&( The #!ess !- heat t#a&s-e# is faster' durale a"!&( *ith %ei&( #!ta%"e+ The aa#e" i&d$st#y$se heat t#a&s-e# #i&ti&( teh&!"!(y+ They $se it

as a& a"te#&ati'e *ay -!# #i&ti&( -a%#is+I& this #!ess !-te& the desi(&ed (ets t#a&s-e##ed

-#!/ a #e.#i&ted ae# !&t! the &eessa#y-a%#i %y the /eth!d !- !&tat heat7 th#!$(h

*hih the dyes (et a%s!#%ed i&t! the -a%#i+It is 'e#y 'ita" that the dye st$Js se"eted a#e

aa%"e !- s$%"i/i&( $&de# heat a&d #ess$#e!&diti!&s


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C!&#ete et!# The#e a#e a "ass !- dyes that a#e $sed i& !&#etea&d a#e !""eti'e"y &!*& as C!&#ete Dyes+

They a#e esse&tia""y the *ate# a&d s!"'e&t.%ased

dyes that !/e i& a *ide a##ay !- !"!$#s7 a&d!/es *ith $&i9$e 9$a"ities+ Wate# %ased dyes a&#!d$e s!-te# h$es *hi"e %!"de# h$es a#e !ssi%"e*ith s!"'e&t %ased !&es+

A"iati!&: T! +eel gaps *ith !"!$# !/!$&ds+ T! (et a (!!d te&si"e st#e&(th a&d epo*y colour

,ooring *ith the he" !- dyes+


75/80

Dyei&( ,ahi&e

B$" dyei&( ,ahi&e


76/80


77/80

!&!/is i& I&dia

#!d$ti!& a&d


78/80

#!d$ti!& a&d

!&s$/ti!&


79/80

,a!# #!d$e# i& I&dia


80/80

synthesis of important dyes

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