# OAR Box 1867

Prepped by Ollie Stewart



### Document

Number: 

# 79 ) ll-B-13 3 Docket Number: 

# A-90-1 9

Printed 12/2/20086:27:24 AM 0

Sheet 79of 95 p. 1P. 2 

## A-90-1 9 ll-B-13 3 «


## MEMORANDU M TO : Proces s Vents Docke t A-90-1 9 FROM : WandaFloy

d DATE : Novembe

r 199 1 SUBJECT : HON NESHAP : Industr y Charact e orobenzoi c Aci d Attache di s aproduct-proces s summar y (PPS ) fo r th e productio n o

f Chlorobenzoi c Aci

d vi aoxidation o

f o-chlorobenzoy

l chlorid e an dvi aoxidation o

f chlorobenzene nitrite . Thi s PPS wa

s developedas par

t o f th e Industria

l Profile project

in suppor t o f th e Hazardou s Organi c NESHA P(HON) regulator

y effort . Information in thi s PPS i s used as abasi s fo

r emission s an

dcost impact estimate s fo

r th e HON program . Listedbelow are th e ke

y reference s usedin developing th e attache dPPS . Jacobson , C . A. , ed . Encyclopedi ao f Chemica l Reactions . Reinhol dPublishing Company , Ne w York, 1946 . pp . 669 , 731 . 

# I e Correspeo£i g filial^

Assrsns e xDocumen ti s Docke tlie n A-90-1 9

ll-B-25 2P. 3

Preparer : r4

w(9

amt * M Oate : '7/3/9 6 Reviewer : ADMINISTRATIVE NOTE S Product-Proe m Cod ! // # tf o fl Hour s spen t o n thi s PP S P- PNam e CWUroJae/r^ i rW

A ul« *

x !&»>»/ « at - tf-cWWiU^fl^U^ Incomplet e Items (part s of for m yo u canno tcomplete

) (lin e » an

d description ) Pat e Cleare d Initial s

Chemical s missin g CA S number s

Plan t wit hCit v

bu t n o Count y

(plan t name , city , state )P. 4

Preparer : K ^ Q>w< Date : /- 7/ ? / ^ Reviewer : Chenrtca TNattf PRODUCT-PROCES S SUMMAR

Y(PPS ) AlterftafimC»efl»icj 1 \ • . 'f

c v.-«* . s ^ J^wC^fefrff i ^ oU-r S CAST 

### 11211 . n o ckh 

### CHEMICA L SPECIFI C INFORMATION 1. 0 U.S . Productio n Re f # . , Pg # . , Re f Yea r (Indicat e th e same referenc e Informatio nfo r an y answer s below

fro m a differen t reference ) mil l ion s o f k g o r million s o f gallon s fir, 3 c



### 1. 7 Produc t Pric e <<~'0 jcv * S/K

o o r i/gallo n
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T-PROCES S SPECIFI C INFORMATIO N otentla l Product-Processe s (P-P )

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Preparer : Date : 7/. ^ /? o Reviewer : ADMINISTRATIV E NOTE S Product-Proces

s Cod s I/J1/2 & Hour s spen t o n thi s PP

S P- P Nam e fci!Ur&m\Wi(L A-c U ui « JXJMH AA TckLraWir?^ ^ mViU . Incomplet e Item s (part s o f for m yo u canno t complete ) Min e # an

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Preparer : £•&

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### Chemica l mm PRODUCT-PROCES S SUMMAR Y(PPS ) 

### (\° 4*** CA S # f ' a+a 

### ** l*r* CHEMICA L SPECIFI C INFORMATION 1. 0 U.S . Productio n Re f # . , Pg # . , Re f Yea r (Indicat e th e sam

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### 2. 0 Chemica l End-Us e Re f I , P g I , Re f Yea r



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# Re f # H L

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# CHEMICA

L REACTIONS
COMPILE D AN D EDITE D B Y C . A . JACOBSO N I'rtitt'Hxnr

of ('hiiiiixjry, West

Virginia Univemity

REINHOL D PUBLISHIN G CORPORATIO N mWES T FORTY-SECON D ST. , NEWYOR K 18 , U . S . A . 1<)4( >m n-2642

i tcel l i s 'in exces s ^ . : "•-• " '

^ NaNO , KC N HC 1

se

H-264 3 o f 1 par t o f : ledint o a le s o f cyan 20 

# ^ r CHLORIN E C1C.H 4 NH , 66 9 11-2845 T o produc e o - o r

m-chlorobenzoi c acid , 1 3 part s o f copper sulfat e crys tal s dissolve di n 5 0 part s o f water , an d1 4 part s o

f potassiu mcyanid e i n 2 5 part s o

f wate r ar c mixe dan dadde dslowly t o 5 part s o f o - o r m-chloroanilin e dissolve di n 1 2 part s o f hydrochlori c aci dan d3 5 part s o f wate r heate do n awate r

bath . Whil e cooling , 3 part s o f sodiu m nitrit e i n 2 0 part s o

f wate r ar e added . Th e nitril e forme di s stea m distille dan dcrystallize dfrompetroleu mether . I t i aconverte dt o th e aci db y heatin g withsulfuri c acid . (a ) C1C,H 4 NH , + HC l + NaNO ,

- + C1C 0 H 4 -N,C 1 + H 2 0 + NaO H (b ) C1C,H4 - NiC l + KC N — C1C.H«-C N + N , + KC 1 (c ) 2C1C,H4 • C N 4 - 4H 2 0 + H 2 S0 < -*2C1C.H 4 C00 H + (NH 4 )jS0 4 P . J . Montague , Rec . trav . chim. , 19 , 5 0 (1900 ) S7 CIO Light11-2646 I n th e photodecompositio n o f chlorin e monoxide , th e chain s ar e ter minate db y th e followin g reactions : (a) 2CIO-»Cl o + 0 , (b ) CI + CIO- • C1, 0 (c ) CI + C10 , - C U + O , A . G. Brown an d J . W . Spinks , Can . J . Res. , B15 , 11 3 (1937 ) 69 11-264 4 ler i n molar itroge n ar e CIO , Br , Light H-264 7 Th e bromine-sensitize dphotodecompositio n o f chlorin e dioxid e appear s t o tak e plac e afte r th e following mechanism : (a ) CIO , + Br * -*CIO * + Br , (b ) CIO * + CIO , — CIO , + CIO J . W. Spink s an d H . Taubc , Can . J . Res. , B15 , 49 9 (1937 ) 69i III,<»| ; I ..!• . 

# ftL 73 1 11-2886 I i f Kl v SS 11-288 6 r .is possibl e irate . Th e crystallized

34 11-288 7 -u s hydro 116 11-288 8 iberatio n th e vol i.ilysi s o f N:i(»(' I

Na-SjO; , 11-288 9 Sodiu mhypochlorit e react s wit hasolutio n o

f sodiu mthiosulfat e accordin g t o on e o

f th e thre e followin g reaction s dependin g upo n th e molecula r rati o o f th e tw o reactin g substances . (a ) 2Na,S,0 , + NaOC l + H, 0 —Na^ 4 0 » + 2Na() H + NaC l (b ) Na,S,0 , + 4NaOC l + H, 0 — 4NaC l + Na,S0 4 + H»S0 4 (c ) 3Na,S,0 , + 5NaOC l -+ Na,S 4 0 « + 5NaC l 4 - 2Na,S0 4 Virgil A . Willson , Anal . EH. , 7 , 4 4 (1935 ) U NaOC l Ni(OH) , 11-289 0 I n alkalin e hypochlorit e solution s an di n th e absenc e o f ammoniu m salts , hypochlorite s ar e remove db y nickelou s hydroxid e an dth e solu tio n change s i ncolo r

fromligh t

gree n t o black . Exces s alkal i ca n the n b e titrate dwithacid . NaOC l 4 - 2Ni(0H) , + H 8 0 — NaC l 4 - 2Ni(OH) , A . Wachter , J . Am . Chem . Soc , 49 , 79 1 (1927 ) 16 0 2 H 6 C10 4 H,S0 4 11-289 1 Oxoniu mpcrchlorat e i s forme db y th e actio n o f ho t concentrate do r fumin g sulfuri c aci do nasolutio n o f dioxoniu mperchlorate . 0,H 6 C10 4 4 - H,S0 4 - ^ OH 3 C10 4 4 - H 2 S0 4 • H 2 0 G . FrederickSmith , Anal . Ed. ; 6 , 22 9 (1034 ) U PCU

118 HO CH 4 COON a Ca(OH) , o-Chlorobenzoi c aci dca n b e prepare db y distillin g sodiu msalicylat e withphosphoru s pentachlorid e an dtreatin g th e resultin g o-chloro benzoy l chlorid e withcalciu mhydroxide . (a) HO-C«H 4 COON a+ PCI ,

- » CI • C 6 II 4 • COC 1 4 - POC1 , + NaO H (b ) 2Cl-C«HrCOC l 4 - Ca(OH) , - > 2C 1 C,H 4 COO H 4 - CaCl , P . J . Montague , Rec . trav . chim. , 19 , 5 1 (1900 ) 11-2892

27