pce-ii unit-v
TRANSCRIPT
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Aromatics-BTX derivatives
Petrochemical Engineering –II
Unit - V
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BTX-DERIVATIVESIsophthalic acid
Benzoic acid
Benzyl chloride, Benzal chloride,Benzotrichloride
Benzaldehyde
Nitrotoluenes
Cresols
Nonyl phenolDiisopropyl Benzene
ydro!uinone, "nthro!uinone
p-diethyl Benzene
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Isophthalic acidC6H4(COOH)2
Process #echnology$ #%o step process
&i!uid phase o'idation o( m-'ylene )y use o(ammonium sulphate*
+Cheron process $ #emp-./0 C pressure is 10-230 atm
It is an important deriatie o( m-4ylene and is usedin the manu(acture o( unsaturated and saturatedpolyesters, al5yl resins, plasticizers, and in 6)res*
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Various process technologiesChe!o" pocess#
It utilizes sulphur )ased o'idation o( m-4ylene in a!ueousammonia at a)out ./00C 710-230 atm to produce amide %hichis then hydrolyzed %ith sulphuric acid to produce Isophthalicacid*
Aco che$ical pocess#
"ir o'idation o( m-'ylene in acetic acid, catalyzed )y a co)altsalt and promoted )y acetaldehyde at temp* o( 200-2800C*
&i!uid phase o'idation o( m-4ylene in the presence o( co)alt saltactiated %ith )romine in acetic acid at /000C 7 /9*/ :g;cm/
pressure*
A$co che$ical pocess# #he o'idation o( mi'ed 'ylenes on a co)alt-manganese-)romine
catalyst system
D%po"t pocess#
#he o'idation o( m-'ylene )y nitric acid at moderated
temperature and pressure conditions*
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U
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Be"&oic Acid(C6H'COOH)
?hich is used in the manu(acture o( caprolactum, phenol andterephthalic acid and used as mordant*
ocess tech"olo*$
&i!uid phase catalytic o'idation o( toluene in the presence o(co)alt acetate at 2@80C 7 22*/ atm pressure*
#he maAor processing steps in the manu(acture o( )enzoic acidconsists o($
Catalytic li!uid phase air o'idation o( toluene
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B e a
c t o r
Conden
ser
D i s t i l l a t i o n
c o l u
m n
=i'er
ilter
Vent gases
?aste%ater
#oluene
Catalyst
"ir
ot %ater
eay ends
Benzoic
"cid
BENIC "CID >= #&UENE
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Benzoic acid is also produced )y o'idation o( toluene in
acetic acid solution in presence o( )romide ionsUses$
It is used as a =ordant, seasoning o( to)acco, indenti(rices +De"ti+ices are agents used along %ith atooth)rush to clean and polish natural teeth* and
medicines* #he gro%th o( Diet so(t drin5s mar5et has increased the
demand o( )enzoic acid as sodium and potassium)enzoate*
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Be"&*l chloide (C6H'CH2Cl)Be"&al chloide (C6H'CHCl2) ,
Be"&otichloide(C6H'CCl)
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ocess tech"olo*#
#oluene can )e chlorinated )y thermal orphotochemical chlorination to get yield a mi'tureo( Benzyl chloride, Benzal chloride,Benzotrichloride*
Chlorination is at @8-2000
CIn case o( Benzyl chloride 2*2 mole o( chlorine per
mole o( toluene*
In case o( Benzal chloride /-/*/ mole o( chlorine
per mole o( toluene*>urther chlorination at 200-2300C %ith UV light
yields
)enzotri chloride
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Deriaties o( commercial
importance o( )enzyl chloride are)enzyl phthalate, )enzyl alcohol,)enzyl chloride deried !uaternary
ammonium compounds, )enzylacetate, )enzyl cyanide, )enzylsilicate and )enzyl amine*
Deriaties o( Benzal chloride are)enzaldehyde, %hich is used in themanu(acture o( per(ume, Faorchemicals, dyes and intermediates*
Deriatie o( Benzotrichloride are
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Be"&aldeh*de (C6H'CHO)
Various Process technology are$Benzyl alcohol route
Benzal chloride route
Uses
It is an important chemical used in themanu(acture o( Per(umes, dyestuG, drugintermediate
=anu(acture o( cinnamic acid, )enzoic acid,pharmaceuticals and photographic chemicals*
It is used to produce ariety o( aldehydes suchas cinnamic, methyl cinnamic, amine cinnamic
and he'yl cinnamic*
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Be"&al chloide o%te# #his process inoles chlorination o( toluene to
Benzal chloride, %hich on hydrolysis yields)enzaldehyde and Cl*
Be"&*l alcohol o%te# #his process inoles o'idation o( )enzyl
alcohol %hich is turn, is o'idized to)enzaldehyde*
>urther o'idization o( )enzaldehyde yields)enzoic acid*
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.ITRO TO/0E.ES=ono nitrotoluenes +o-7p-nitrotoluenes are
manu(actured )y direct nitration o( toluene inthe presence o( mi'ture o( N. 7 /
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#oluene diisocyanate is used in the manu(acture
o( polyurethane*
Dinitration o( toluene yields /,3-and /,@-dinitrotoluene important (eed stoc5 in the
production o( diisocyanate*
Nitration is carried out in the presence o( a
mi'ture o( N. 7 /
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#rinitrotoluene %hich is %idely used in )othmilitary and industrial e'plosies, is manu(actured
)y nitration o( toluene in a mi'ture o( N. 7/
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Cesols - CHC6H4OH>irst stage o( the production o( cresol ismanu(acture o( toluene sulphonic acid )ysulphonation o( toluene*
#he second stage inoles reacting o( moltencrude sulphonation product %ith molten causticsoda containing 3-8H o( caustic potash at
.800C (ollo%ed )y leaching o( sodiumcresylates %ith %ater and decomposition %ithgaseous sulphur dio'ide to gie crude cresols%hich is 6nally separated )y distillation*
o( her)icides, dinitro-o-cresol, /-methyl 3-chloro pheno'y acetic acid*
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Ad!a"taes#
-Cresol is used in the manu(acture o(her)icides, dinitro-o-cresol, /-methyl-3-chloropheno'y acetic acid, /-methyl-3-chloropheno'y )utyric acid* It also 6nds application in
the manu(acture o( plasticizers, antio'idants*p-Cresol is used in the manu(acture o(
)utylated hydro'ytoluene %hich is used in themanu(acture o( antio'idant in edi)le (ats, in
plastics, ru))er and petroleum products*m-Cresol is used in the manu(acture o(
insecticide, (ungicide, industrial )actericide*
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.o"*lphe"ol(CH3C6H4OH)Nonylphenol is made )y reacting nonylenes, usually propylene
trimer, %ith phenol using /
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H*do%i"o"e (C6H4(OH)2) #he maAor use o( hydro!uinone are as an antio'idant,
antiozonant in ru))er manu(acture and in chemical(ormulation (or the deelopment o( photographic 6lms*
It is also used as a polymerization inhi)itor*
It is used as a sta)ilizer in paints and arnishes, motor(uels and oils*
#he maAor process technologies are$
ydro'ylation o( phenol
Bisphenol route"cetylene route
Electrolytic o'idation o( )enzene
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"nthra!uinone+C@3+C/C@3It is an important dye intermediates and pigment*
#he maAor process technologies are
hthalic a"h*dide a"d 5e"&e"e o%te#
St*e"e o%te#
Dimerization o( styrene to methyl phenylindane%hich on o'idation in the apour phase yieldsanthra!uinone*
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Friedel-Crafts reaction$ It is also prepared )y the>riedel-Cra(ts reaction %hich inoles a reaction )et%eenthe organic compounds )enzene and phthalic anhydride in
presence o( aluminum chloride* #he resulting o-)enzoyl)enzoic acid, an organic acid, then undergoes(urther reactions, (orming a"tha%i"o"e #his reactionis use(ul (or producing su)stituted anthra!uinones*
Diels-Alder reaction$ #he Diels-"lder reaction o(
naphtho!uinone +class o( natural phenols and )utadiene+hydrocar)on (ollo%ed )y o'idatie dehydrogenation+remoal o( hydrogen %ill also produce a"tha%i"o"e
BASF: Baden "niline and actory+B", the largestchemical company in the %orld and is head!uartered in
Kermany, has deeloped a process that proceeds ia theacid-catalyzed method o( styrene, an organic compound toproduce antha!uinone*
http://www.innovateus.net/content/what-are-organic-compoundshttp://www.innovateus.net/content/what-bisphenolhttp://www.innovateus.net/science/what-metallic-hydrogenhttp://www.innovateus.net/content/what-are-organic-compoundshttp://www.innovateus.net/content/what-are-organic-compoundshttp://www.innovateus.net/science/what-metallic-hydrogenhttp://www.innovateus.net/content/what-bisphenolhttp://www.innovateus.net/content/what-are-organic-compounds
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p-Dieth*l Be"&e"e(DEB)
Important high alue, lo% olume, specialty
chemically deried )enzeneIt is used as desor)ent (or separating p-'ylene
(rom 'ylene isomers*
#he conentional process inoles al5ylation
o( )enzene %ith ethylene and thendehydrogenation o( ethyl )enzene, %herestyrene and mi'ed diethyl )enzene is (ormed*PDEB can )e separated (rom mi'ed diethyl
)enzene stream )y adsorption
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