I'

-0
>1;'

;./b 000 ~00 ( f)/b !

"

:/

:l
Thu dro.ini.n;:s oor:.inc ")lff at the lowor tetlpGrnturcs nrc of no use nnd !",rc c'..isc.:'..rcled but Dl\ terkl of C.rt. 22-29.5C. is

reused in the next 'brysta.llisr--tion.

1fr-.kri['.13
U5J.[;CI

The'i.JUrifiml D.. f\tcri:1.l is then L-eltec1 [\ll.1 run out: 1.B57 tonne 2:4-dichloronitrol)enzeoo
tonne 2;4-Gich18rcnitrobenzenB pure

crude/

. Overnll yielc.1. fro.:l 1:.3 <.1iohloro~cnzene = 52.1% tho

Arolytioc.1
dt'..o?:. t

1.

2:4-c.iClhloronitro~cnzem

endes

2. 2:4-d"iohlorol'..itrc,bcnzem pure : c.Pt.

c.rt. 27.'ce ..

net 1e33

-th.-;.n .3OcC .

!...~l

i)ro<'i.ucti:m:

15.37
1943
22,00e
}.-..g.

I " G

"D-r;:>QP"j;'Di . \..T!~~u.o.4J:

H.W. 192

4-500 ks.
5500

1~dich1crcbe~GneDCltc~ is char[cQ to the nitr~tcr n~

rUXC(: <,-ci,', (35;~ illK) [tsitntion ~ .. CGc1i?~.

kg.

GO% H2ro4-)

Nitrat~on

[t(.ldcr;" with ~t.:'..rts nt 700.

Dl1r1.. than tenper:>.turo is rc(luc0:"~ to 4D-45C. after l~ hr. ""

ap:;.-;rox.

After ill
650.

the

~i:1

hrt.3

~con

a.ddec.1..

the 'h8.tch i.s rniscd

to

eJrl held

a.t this

tCL~)erE1.turefor 2 hrs.

The 1~tch is then cuole~ to 55-C~oC. Ciluted with 440 1. W<,.ter nn'l o..l1ovreJ. -to settle. The lower lo..yer of 70% acid is then eTc.\1n Gff nn:l to the sulphuric [1.cic-: C(.,nccntr~tion p:4'U1t.

sent

Thu nitrcbo{-:y ll\Ycris

wn"-::-rr:1

w[l.shec.'t
n."

with

Wc.IT.1

_'r.:\tcr, then
f::i.n..n.lly \.lIl.(.ler vacUl..U:1.

wi th' 'YlD.:tcr contt1.ini~: lit ~le socl"'.n.n,~ wi th Warn vr.:\ter until roe froD aciCl..
The procluct

is fiJll\ll,y Jriecl

1:(y hen tine

I
r

162. "

l~i~s

co~~tiorv'.tonnc
t.-dichlorooonzone

of 2:5-(lichloronitrobcnzonc

1..
2.

llixoc1 ncid

35%

0.79 tOMes, yiold = 9710 theory. 1Nl3 60% H~S04 1.0 t..

Serv iocs conaur.r.l?'ti_c_nLtonnc f' 2 :~-dichl(~roni tro ~cnzonc o

Elootd.ci ty
Stean
Wn.tor

Air

p-dichl<.~robc!L.!;eno C.l~t. Nut lesoS thc.n 2: 5-c;'ichlo7.'(J'ti. tro lJcnzcnc C.lJt. n..:,t less

52.50.
than 52.8cC. 1)rc(~uct3t <"'..s for

~D.nllcr

lL:5-1.50 tcmje!j_i(Jnt~_~f vr'X_kus nitro l-clllc,r.;-2: 4-chni troh:nZC1't) i. c.

1 x 8 h.3 C.I. ni tr~ltor

1x 12 l.~jH.S. VD.cuun 'l.'1~h vO~3cl 1 x 20

1:.

c1ryln~: vessel.
ltl~' ,COO kg.
354}OOO leE.

(lJr~ck-1incl:)

NO. 101

Cru(~G
T.li..'Cture

- M.W. 161

(or chiorin.~ichlorctoluone C1 nt 10-::'50 .. ".toc with dry frnctiunation un.J.U ~:"'e!1.5l-".r. .. ~ ';' hr 1 025 a t 150 lS reac he,-,. 2 .. ~

dr.J p-ohlorotoluene forerunnin"S) are

'At thi~ point chlorL~ti0n

13 sto~JO~ and the oil is

rrn~hctl neut~l rrith mter in a YJouden vut .. The :\.'\tch io then hO:'.te:J. in 3.ll iron ves.sel with 10% 'caustic 3ccb liqu,Jr for 24 hr. nt 1100. to Q<;';ConpCBEJ ~i(:''::-ch.'i.ill chlorin.:.tcQ 'J:1Iu(lucts. The aqu,~oU3 CD.ustic In)rer i.'5 th..:m (ira\m off C'..nJ. .
the tn!ude .l.1ixturG o:f 2:4-dichlorotoluenG (1:iJ1hl;f.rotQ~),.vmo u~<Jc1_f..:;;r ..:istill.<'..ticn. anc1
.3

:1,,-

,
I

The chlorination
frct) cor.c.i tiol1.9.

r.~ustbe onrrie~. out un8.er nois turc-

[>-chkrotclueno

o. SSI tor..
"10

.l7chlorotclueno

c.r. not less th~n 7C.

(UohlO1'ctclucru Svrvices

cruci.a:

Density 1.220 r.t 19C.

of
Cl'1.lC.~C

ccnsul1pticns/toru1e

c'.ich1orotolucnca

E1Gctricity

idr

iltltcr

st~c.r.l

2GI.. K.~;.H. 0.7 tooncs L.~. )O"vO H) 1;D M3

Plnnt (f:r 24 tcnne/nonth_~_~'ul

trichlorobcnzcnc

cruCe

ci1lorinaticn products) see

1. 2.

x 4H3 C.r. chlorinntors

15J.r3 wCu<lcn V8. for

1 x

'r-'.shillG

ncu

tn'.l with

VIa ter.

NO.

102

CH

G:>{

Q3C1 c
:.sC'r.lcrs

M.N. 161

CL
C1
Ul1J::ler vncu1..2Irr;.'

?hc cruce chlGri~ti~n product contGL~32:4-dichlorotoluenc

:.:.ncl 4-("'.ichlc rot olucnc in the pro;;ortions of 100 to .30, .3: i.lesicks lr'chlcrotclucnc and polych19rimtOd toluenes. The
Cl.:-Csei.XlI':1 ted by fraction2.tion No.
Frncticn

Pr:-'.ctiun 1.

conl~siti~

Fr~ction Jisposal

Forcrunnin~s

(22% of charce) -

used for subsequent

chlorimtions.
n.dued to

.2.

r~chlorQtoluonc ~rJ 2:4~

!nternc<liates I

fr~ction.'1.tiOM

subsequent

c.1.ichl~rotoluene

164., .
..

Fraction
No

3
4.
.5

Fraotion 6orJJ?Os:i;.~i2!:
2:4-aichlorotoluene pure

Frrtction disj?csnl

.Intcrued~cs II

2:4-Cichlorotoluenc~a 3:4-cliohlorotoluenc

accuoul~ted fo~ ref'rC'.ctiomtion ,

<1itto
C.IlC1

!~sic1ueI

3: 4-~"\.ichlorotolucne

hi,:.:hcr chlorir..:J.tec:''!.x,l'..ics Tc cbt<:'..in3:~cliahlorctoluenc pure the t\;,: fr.::cti'_'l13(4) c. Inter:Jedio..te5 II rm'l ~esF.uc; I 2.re sel-":'.r<:'..tcly and (5) distil1e~ yield: collectca

i.

<:'..n2

to

Fracticn
Ne.

Fcrcru.nnin:~s: rich ~n 2:~-Gic;ll8rotolucne

CCT:'lbined with Interscdio..tes I fur

re-

fracticr.<:l.

hen.

2['

Intem<.;'liatc fr:'.cti,:,n r..;f 8:'.1.10 ccnposi tion ClS

ikfrc..ctiol".atocl with
Intc:rD.;clio.tcs II

in ten:1CdL1.tes

tile l:3t fr:-.cti;:'lnr.. icm. t 3<:'...

4D..

II fro[1

3:4-~ichlorotolucno
ACCUDUb.

rcfr2..cticmtLn.

t e(j, fo r

Use(l for pento..chlllro toluene for Crp.!)hi to electrode L~re0n~tiGn

la:...9.

tcrio..l:s ccn3u.'"J.pti;cns/t~nn9_oJ:~4-dichlcratoluene 2:

~urc

Mixed 2:4 cna 3:4 Cichlorotoluene TIy-prccuct 3:~fiohlorotcluen6 n:s

1. 926 tomes.

The by~cduct a solvent.

.3:4-il~er

(0.310

tit

0.310

toIll1CS

iSCf.1er) i3 U3eG.

Tho abGVB ir;norc the ruxunt of' p-chlorotcluen.e present in . ~ the fore:c-..umi..'"lSS retu...-red to the cr..lorirw.tion. ~suni.n,:; fraotion I frcn the first .frL'.ctionaticn to be pure P-OhlOl"0tcluene 'ret-uxned to the chlorin:'1 tion the yiel:i3 becOL1c:
. 2:3

2:~dichlorotoluene dichlorotoluona

64.4~ the t'ron p-ohlcmol\:.C~

19.8)fo tho . iG5.

----

__

_-~

IJ1l1lyticcU...

(1,'.t~

density 1.220
.:It

Diohlorotoluone cruQc: 2;4-diohlorotolucne l~c: .3;4-c.ichl(\I'Ctcluenc IUI'(;:

c.rt .
C.Pt.

.) 15 C.

-11.ce.

-15.7CC.

Servic os
stann
"\l.:1.tcr.

oonsur:rpticns

Electricity

1670 K."\7.H. 1700],1

,.38 tgnnc

H.P.

1[0.

103

1. G.

G1U:LSilEIH

---M.W. 181

Iron ;rt.c1..uction Gf nitro tcc\y (He. 163) Iron reJiuoticn tr,)e .3 wi th, no..:11th.''.. oxtr:'.c ti0n d'

l",'lsC

4CDO kg.

1500 1. 15 kg. 4000 k8.

nitrchJrclruquin:.mu

hrouljht tCI the lX',iL Reili.1ction is c-U'riccl. out' r.t the. '<-)d:l by r\.J.c1iti8n cf iron 1x.JriI\3S n t such ..~ r.:<.to ~"S to r.nint;:in the roquired rnte of rtJductL'n. After a,:;'J.ition of

wn.ter r.rrl .. fornic ncic1 and the nixturc

dictJurl

ether

i3

.:::ho.r:~cll

to

eoo

1.

2000 kg. iron 1Jorin.:~s) or r;hGn the rc:--.ction tends to 310YI (:arm, 15 kg. fOITlic [lei:} i;;l c..Jc.ec.. iu'ter cor:IiJloticn of rClluction
nnphtha is addce, the r~tch n~itr\.to~ nnd then

yrith

o.llcwed to settle fcr 15 Din. 'Ihc n'1phth.~ lc.yer is c1rmm off IU1dt he iron sludGe extraoted two or three tines \1ith na~Jhthn (DO 1. per cxtrr.otion). The 11.:lphtl'1.~ e:ctr['.ots qrcJ oODbiru)d 'o.nd fil tcred for renov['~ of iron e].u:l:.:c; rL..'\I)hthCl. is distilled. c.;ff

live

stc~n nncl then the

The iron

auine distilleJ. Dver

under

n.CUUf1.

slud.:.;c s frce;d f1'ol.l i

mphthr\. by

stO['J:l

(1istill.o..tion.
IGG

Material

.QoruruI'Jj?tiondtonne of 2: 5-diethcxyo.nilinc

1.

Ultrohyc1roquinoncdiethyl

ether

1.27
1.24 0.01 1.00

t. t. t.
t.

YieLllI: 91.8J~ tho

I .

Ir.J~
FOI"inic ncid

lhph th.'\

(gro 63)

(r~ccvc~ not given)

, S(~rvice c()l1.tur-'9ti()~tonne
21ectricity
stC:\r.1

2: 5-di.cthc~a.nilino (
540
JC,W.H.

14.6

t.

L.I'.
H.P.

4CC M

l25~.

21

Nihor.,:rdroquinuno (~iethylethcr 5-p.ie thoxy.'lIliline as i\-,r 4-chkro-o-a.ni~idine

M.Pt.

c.Pt.
::f

Plant:

all ~Jiros roquirin~ solvent extr:'..oticn,

(No .30) for 12 tonres/f1onth

19.37
1943

'lr3

73 ,000 .1~R ,000 l~B.'

StaN:! lli.::;tillntion Total cycle t:L"7lC

A3i:.i tion

I..if

nitro

cOrJp0urul

12 hr.

40 hr.

~ hr.