PCE-II UNIT-V

8/18/2019 PCE-II UNIT-V

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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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PCE-II UNIT-V