OAR Box 1867 

Prepped by Ollie Stewart 

Document Number: 

79) ll-B-133 

Docket Number: 

A-90-19 

Printed 12/2/2008 6:27:24 AM 

0 

Sheet 79 of 95 

p.1 
P.2 

A-90-19 

ll-B-133 

« 

MEMORANDUM 

TO: Process Vents Docket A-90-19 

FROM: Wanda Floyd 

DATE: November 1991 

SUBJECT: HON NESHAP: Industry Characte orobenzoic Acid 

Attached is a product-process summary (PPS) for the production of Chlorobenzoic Acid 

via oxidation of o-chlorobenzoyl chloride and via oxidation of chlorobenzene nitrite. 

This PPS was developed as part of the Industrial Profile project in support of the 

Hazardous Organic NESHAP (HON) regulatory effort. Information in this PPS is used 

as a basis for emissions and cost impact estimates for the HON program. 

Listed below are the key references used in developing the attached PPS. 

Jacobson, C. A., ed. Encyclopedia of Chemical Reactions. Reinhold Publishing Company, 

New York, 1946. pp. 669, 731. 

I e Correspeo£ig filial^ Assrsnse 

x Document is Docket lien 

A-90-19 

ll-B-252 
P.3 

Preparer: r4w (9amt*M 

Oate: '7/3/96 

Reviewer: 

ADMINISTRATIVE NOTES 

Product-Proem Cod! //# tfo fl 

Hours spent on this PPS 

P-P Name CWUroJae/r^i rWA ul« *x !&»>»/« at- tf-cWWiU^fl^U^ 

Incomplete Items (parts of 

form you cannot complete) 

(line » and description) Pate Cleared Initials 

Chemicals missing CAS numbers 

Plant with Citv but no County (plant name, city, state) 
P.4 

Preparer: K^ Q>w< 

Date:

 /-7/? / ^ 

Reviewer: 

ChenrtcaT Nattf 

PRODUCT-PROCESS SUMMARY (PPS) 

AlterftafimC»efl»icj1 

\ •. 'fc v.-«*. s ^ J^wC^fefrffi 

^ oU-rS 

CAST 11211 . 

no ckh 

CHEMICAL SPECIFIC INFORMATION 

1.0 U.S. Production Ref # ., Pg # ., Ref Year 

(Indicate the same reference Information for any answers below from a 

different reference) 

mill ions of kg or millions of gallons 

fir, 3c 

1.7 Product Price 

<<~'0 jcv * 

S/Ko or i/gallon 

f\it d-v-w 

1 .8 Comments 
P.5 

2.0 Chemical End-Use Ref # , Pg # , Ref Year 

l&fi Percent 
3.0 U.S. Producers Ref « .. Pg # ., Ref Year 

Billions vf kg fil minions of gallons 

3.2 Name, Location, aid Capacity 

Process Used 

(use P-P I) Jnlts 

rOo ^«A< / v cM i.. Po C^e>^ 

KJo ciai:Q_ 

Total Capacity' ^ <A*k 

b> 
P.7 

T-PROCESS SPECIFIC INFORMATION 

otentlal Product-Processes (P-P) 

Name 

Ref I , Pg * ) 

Commercially % Nat'l 

Viable (y/n) Capacity 

f.KWrg^Wt* ^ *<••<! 1^3 toekti*/, al *Ma>rs Wra^r. ,A,W * Y $& 

Documentation of P-Ps Excluded 

P-P not 

lerdallv Viable 

/to nil/r\btfi ware. 5>U" / 

C*pttt*^ 

Reasons 

c 
P.8 

tmmm Ref # ar< Pg I T^i. 

Hr Oxidation Reaction 

QxtdatToTl^eacttOTK 

Alkylation Reaction 

Carbonylation Reaction 

Halogenatlon Reaction 

Condensation Reaction 

Dehydrogenation Reaction 

Dehydrohalogenation Reaction 

Esterification Reaction 

Hydrogenatlon Reaction 

Hydrohalogenation Reaction 

Hydroformylation Reaction 

Hydrolysis Reaction 

Nitration Reaction 

Oxyacetylation Reaction 

Oxyhalogenatlon Reaction 

Sulfonation Reaction 

Catalytic Reformation 

Hydrodimerization Reaction 

Generic Reaction 

lain how you selected the reaction type In line 4.3. 
P.9 

4.5 Written Description 

In the left margin, indicate references and page numbers throughout written 

description. 
P.10 

5.0 Process Flow Diagram (attach at end of package) 

5.1 Flow Diagram Reference: Ref # , Pg # 

5.2 Comments on Flow Diagram 

Component Tvoes 

Distillation Columns 

Absorbers 

Strippers 

Reactors 

Condensers 

Vaporizers 

Others 

Ref * ., Pg * 
P.11 

Chemical Data 

Balanced Chemical Reactions 

-ipoda'"*8 " 

2 ||0 <; Wymote rlf (if ^ 

Ref # , Pg # 1 

ffcfMf* :KW,5k 

6.2 Chemical Tree Ref # 

., Pg # 

/uUjf/**^'"81 6/tiA»Ti-* 

^ 5«<<r^ yr^^y ^^ ^ 

u <XV$ ckloT&r*. 
P.12 

\ 6.4 ^Stoichiometry 

X,^ J I 

Ref # ECU Pg # T£L 

Show calculations and assumptions and then summarize 1n table on next 

page. 

1 ' /si-r? ' 

t,i? • '4 i 

r , 7* y 

,iV? 

Qr\*r*\ttKma\ .Ck|»ii^rf 

£.37 . > i2i- '/ 

pkft*p1vor^s f)CAT*cklor>Jt 

I 

- /. //, 

= A n / 

% 

P^'f 

<-*1 vV y tfO.»/ 

' •• i — 

~ . zrc 

* > • 

.?#* 

* 
P.13 

6.4 Stoichiometry Conversion Factors 

a) *» ^ * 

b) wwmm¥m*f<r&*nmmm 

c) cwm\myw»* 

d) Conversf off F « 

e) 

f) Conversion Factor Comments 
P.14 

6.4.1 Product 

6.4.2 Raw Material (si 

#1 Ueilv* ^1,'ftrAk 

#2 pko^6/V<p fr\tATa\cr\1.rJt 

#3 t^. U hj.^roiirf* 

#4 

#5 

6.4.3 Co-Products 

#1 

#2 

#3 

#4 

#5 

6.4.4 Bv-Products 

#1 faXei^m rkUfiJ* 

#2 t^ U k, «<»«>* f-

#3 ph^A^s &** ckUn'J 

#4 

#5 

6.4.S Intermediates 

#1 CkiarUffhtj/ cklon'ck 

#2 

l/BVx 

tbot(* nB 

Pr*—r>»^a-

)°o 25" £7 J 

\\k\o\S 

Aoz3 

M l / 

» *?7 

?«? 

,A« 

. ?* 

/. //f 
P.15 

?-* mmmm^^mmm^n ^ _ (Y/N) Ref # P9 # 

7.7 

7>$ WmM^t%WwSVt' victhw 

7.9 Comments Ref # , Pg # 
P.16 

7.0 Process Vent Emission Sources 

7:1 /mmmwtota**1** e»^«o»$^ 

7.2 Air Oxidation vent emissions? _ 

(Y/N) 

(Y/N) Ref # ., Pg # 

7.3 Comments Ref I ., Pg # 

7;«r (Y/N) Ref I ., Pg # 

7.5 Comments Ref I ., Pg # 
P.17 

9.0 Storage Emission Sources Ref # , Pg # 

9.1 Ar*:ap»FfaT-$ stored? (Y/N) 

9.2 What materials are stored? 

Storage Service 

1

 Ty Pe 

9,2,1 Product 

9.2.2 Co-Products 

9.2.3 Raw Materials 

9-2,4 Intermediates 

9.4 Comments 
P.18 

8.0 Transfer Emission Sources Ref # , Pg I 

8.1 A¥^^|pfcW^PI^clucts^aftSfei ^ (Y/N) 

8.2 What materials arei transferred! 

8.2.1 Product 

8.2.2 Co-Products 

8.3 Comments Ref # , Pg # 
P.19 

Stream #3 

Organics _ 

HAPs 

Water 

Other _ 

10.4 Comments Ref # , Pg # 
P.20 

10.0. Wastewater Emission Sources 

io;i u'vmRirtw'prfeMftt! _ 

10.2 Describe wastewater 

Ref I ., Pg * 

(Y/N) 

Stream Equipment Component 

Number Producing Wastewater Comments on flow 

#1 

#2 

#3 

10.3 Stream Composition 

(provide only 1f readily available) 

Stream #1 

Ref I 

Steam #2 

., Pg # 

Organics Organics 

HAPs HAPs 

Water 

Other 

Water 

Other 
P.21 

Preparer: 

Date: 7/.^ /?o 

Reviewer: 

ADMINISTRATIVE NOTES 

Product-Process Cods I/J1/2& 

Hours spent on this PPS 

P-P Name fci!Ur&m\Wi(L A-cU ui« JXJMH A AT ckLraWir?^^ mViU. 

Incomplete Items (parts of 

form you cannot complete) 

Mine # and description) Pate Cleared Initials 

Chemicals missing CAS numbers 

Plant with C1tv but no County (plant name, city, state) 
P.22 

Preparer: £•&> <V\fftf<\ 

Date: -/ w 

Reviewer: 

Chemical mm 

PRODUCT-PROCESS SUMMARY (PPS) 

(\° 4*** 

CAS # f' a+a 

** l*r* 

CHEMICAL SPECIFIC INFORMATION 

1.0 U.S. Production Ref # ., Pg # ., Ref Year 

(Indicate the same reference Information for any answers below from a 

different reference) 

| millions of ko or millions of gallons 

o 

1.7 Product Price 

fa«UU 

S/Ko or S/oallon 

*o &W 

1.8 Comments 
P.23 

2.0 Chemical End-Use Ref I , Pg I , Ref Year 

use Percent 
3.0 U.S. Producers Ref # ., Pg # ., Ref Year 

Millions Of kg QL millions of gallons 

3.2 Name, Location, and Capacity 

Process Used 

(use P-P I) KITE" 

0\o cta\c, fvo c*cV* fit, d-ciy; Ae J'+1 

O 

Total Capacity f\' M 
P.25 

T-PROCESS SPECIFIC INFORMATION 

ptentlal Product-Processes (P-P) 

Name 

Ref # , Pg I 

Commercially % Nat'l 

Viable (y/n) Capacity 

r\\oCJbtr\-£ati txsU i^U /iXJ^fcHafi »E cVUobt*l*,\ Aittiik V fir 

\\ H 

o u .^JUKQA »v ckWaieH^ntftvW^ y f» 

Documentation of P-Ps Excluded 

P-P not 

lerclallv Viable Reasons 

c^rebAf't c ft.6i^ </m <b<lAft.V\otv A rklora ^rcgftfML rviVrAe 
P.26 

11 r Oxidation Reaction 

Oxidation Reaction J ) 

Alkylation Reaction 

Carbonylation Reaction 

Halogenatlon Reaction 

Condensation Reaction 

Dehydrogenation Reaction 

Dehydrohalogenation Reaction 

Esterification Reaction 

Hydrogenatlon Reaction 

Hydrohalogenation Reaction 

Hydroformylation Reaction 

Hydrolysis Reaction 

Nitration Reaction 

Oxyacetylatlon Reaction 

Oxyhalogenation Reaction 

Sulfonation Reaction 

Catalytic Reformation 

Hydrodimerization Reaction 

Ref # H L , Pg # 21L. 

Generic Reaction 

lain how you selected the reaction type in line 4.3. 

|,V*T-* ^<vc*k*. o*yT><» * *<f«W r» re«<fr*t 
P.27 

4.5 Written Description 

In the left margin, Indicate references and page numbers throughout written 

description. 
P.28 

5.0 Process Flow Diagram (attach at end of package) 

5.1 Flow Diagram Reference: Ref # , Pg # 

5.2 Comments on Flow Diagram 

$.*", Ref # ., Pg # 

Component Types 

Distillation Columns 

Absorbers 

Strippers 

Reactors 

Condensers 

Vaporizers 

Others 
P.29 

6.0 Chemical Data 

6.1^ Balanced Chemical Reactions Ref # ______ Pg # 

CkW* biAtt-A ivV-ld Chl«r.eic^%«Vc «o / 

t<M.fn*t\,«iks 

BCrl 7>, 

6.2 Chemical Tree Ref # , Pg .# 
P.30 

\ 6.4 \to1chiometry Ref # £CH 

., Pg # 2IL 

\^yshow calculations and assumptions and then summarize 1n table on next 

page. 

r , 57? 

4.*.*t«t(«m S**IT*|-« 

0 7 • /• 

/ z ,*n-

*/*K<~ 

631 • ^/ • && 

1

 1 

- . tl<> 

^ifuTl C A-G ^ 

t.u- %•** ' .yy 
P.31 

6.4.1 Product 

6.4.2 Raw Materials! 

#1 _ 

#2 

#3 

#4 

#5 _ 

r.WUrehtn-rrtne motile 

S>t,/Lr\i «c J • 

UJA.\tf 

6.4.3 Co-Products 

#1 

n 

#3 

#4 

#5 

< 

§,4,4 BY-ProgMcts 

#1 <w* 

#2 . 

#3 

#4 

#5 

y -

6.4.5 Intermediates 

#1 

#2 

I/8V1 

LXo—flLin. fa'*—• ,37? 

J^l. 
P.32 

6.4 Stoichiometry Conversion Factors 

a) BH^^aWf^rY*^ 

b) tm&w%^&$» 

c) Ceri^r^lon/r^ct^^r^Co^miRfi 

,1c r\cWl 

f) Conversion Factor Comments 
P.33 

7.0 Process Vent Emission Sources 

7.1 pricesj vent emissions! 

7.2 A1r(^^lff<»i>fiiire»fssfonst| __ 

(Y/N) 

(Y/N) Ref I 

., Pg # 

7.3 Comments Ref I ., Pg # 

(Y/N) Ref # ., Pg # 

7.5 Comments Ref # 

., Pg * 
P.34 

r.8? *m 

7.7 

74T Jfi 

7.9 Comments 

(Y/N) Ref # 

Ref # 

., Pg # 

., Pg # 
P.35 

8.0 Transfer Emission Sources Ref # , Pg # 

5.1 tm^^p/m-mtiicts Transferred (Y/N) 

8.Z What iateriaTs are transferred? 

WWwWWWiWfl*, 

9x2-1 Product 

9,2,2 Co-products 

8.3 Comments Ref # , Pg # 
P.36 

9.0 Storage Emission Sources 

9-1 A>*ii|£t*tt stored? _ 

9.2 What materials are stored? 

Ref # ., Pg # 

(Y/N) 

Storage Service 

Type 

9.2.1 Product 

9.2.2 Co-Products 

9.2.3 Raw Materials 

9,2,4 Intermediates 

9.4 Comments 
P.37 

10.0. Wastewater Emission Sources 

NT.1 r$%$pjpfflt»r- present? __ 

10.2 Describe wastewater 

Ref # ., Pg # 

(Y/N) 

Stream Equipment Component 

Number Producing Wastewater Comments on flow 

#1 

n 

#3 

10.3 Stream Composition 

(provide only if readily available) 

Stream #1 

Ref # 

Steam #2 

., Pg # 

Organics Organics 

HAPs HAPs 

Water 

Other 

Water 

Other 
P.38 

I 

Stream #3 

Organics . 

HAPs 

Water 

Other 

10.4 Comments Ref # , Pg # 

l3 '. 
r 

-^ t ft.:'. -A 

OF 

CHEMICAL REACTIONS 

COMPILED AND EDITED BY 

C. A. JACOBSON 

I'rtitt'Hxnr of ('hiiiiixjry, West Virginia Univemity 

REINHOLD PUBLISHING CORPORATION 

m WEST FORTY-SECOND ST., NEW YORK 18, U. S. A. 

1<)4(> 
m n-2642 

i t cell is 

'in excess 

^ . : "•-• " ' 

^ NaNO, 

KCN 

HC1 

se 

H-2643 

of 1 part of 

: led into a 

les of cyan20 

^ r 

CHLORINE 

C1C.H4NH, 

669 

11-2845 

To produce o- or m-chlorobenzoic acid, 13 parts of copper sulfate crystals dissolved in 50 parts of water, and 14 parts of potassium cyanide 

in 25 parts of water arc mixed and added slowly to 5 parts of o- or 

m-chloroaniline dissolved in 12 parts of hydrochloric acid and 35 parts 

of water heated on a water bath. While cooling, 3 parts of sodium 

nitrite in 20 parts of water are added. The nitrile formed is steam 

distilled and crystallized from petroleum ether. It ia converted to 

the acid by heating with sulfuric acid. 

(a) C1C,H4NH, + HCl + NaNO, 

-+ C1C0H4-N,C1 + H20 + NaOH 

(b) C1C,H4- NiCl + KCN — C1C.H«-CN + N, + KC1 

(c) 2C1C,H4 • CN 4- 4H20 + H2S0< 

-*2C1C.H4C00H + (NH4)jS04 

P. J. Montague, Rec. trav. chim., 19, 50 (1900) S7 

CIO 

Light 11-2646 

In the photodecomposition of chlorine monoxide, the chains are terminated by the following reactions: 

(a) 2CIO-»Clo + 0 , 

(b) CI + CIO-• C1,0 

(c) CI + C10, - CU + O, 

A. G. Brown and J. W. Spinks, Can. J. Res., B15, 113 (1937) 69 

11-2644 

ler in molar 

itrogen are 

CIO, 

Br, 

Light 

H-2647 

The bromine-sensitized photodecomposition of chlorine dioxide 

appears to take place after the following mechanism: 

(a) CIO, + Br* -* CIO* + Br, 

(b) CIO* + CIO, — CIO, + CIO 

J. W. Spinks and H. Taubc, Can. J. Res., B15, 499 (1937) 69 
i III,<»|; I ..!•. 

ftL 

731 

11-2886 

I if 

Klv 

SS 

11-2886 

r .is possible 

irate. The 

crystallized 

34 

11-2887 

-us hydro116 

11-2888 

iberation 

the voli.ilysis of 

N:i(»('I 

Na-SjO;, 11-2889 

Sodium hypochlorite reacts with a solution of sodium thiosulfate 

according to one of the three following reactions depending upon the 

molecular ratio of the two reacting substances. 

(a) 2Na,S,0, + NaOCl + H,0 — Na^40» + 2Na()H + NaCl 

(b) Na,S,0, + 4NaOCl + H,0 — 4NaCl + Na,S04 + H»S04 

(c) 3Na,S,0, + 5NaOCl -+ Na,S40« + 5NaCl 4- 2Na,S04 

Virgil A. Willson, Anal. EH., 7, 44 (1935) U 

NaOCl 

Ni(OH), 11-2890 

In alkaline hypochlorite solutions and in the absence of ammonium 

salts, hypochlorites are removed by nickelous hydroxide and the solution changes in color from light green to black. Excess alkali can then 

be titrated with acid. 

NaOCl 4- 2Ni(0H), + H80 — NaCl 4- 2Ni(OH), 

A. Wachter, J. Am. Chem. Soc, 49, 791 (1927) 16 

02H6C104 

H,S04 11-2891 

Oxonium pcrchlorate is formed by the action of hot concentrated or 

fuming sulfuric acid on a solution of dioxonium perchlorate. 

0,H6C104 4- H,S04 -^ OH3C104 4- H2S04 • H20 

G. Frederick Smith, Anal. Ed.; 6, 229 (1034) U 

PCU 

118 

HO CH 4 COONa 

Ca(OH), 

o-Chlorobenzoic acid can be prepared by distilling sodium salicylate 

with phosphorus pentachloride and treating the resulting o-chlorobenzoyl chloride with calcium hydroxide. 

(a) HO-C«H4 COONa + PCI, 

-» CI • C6II4 • COC1 4- POC1, + NaOH 

(b) 2Cl-C«HrCOCl 4- Ca(OH), -> 2C1 C,H4 COOH 4- CaCl, 

P. J. Montague, Rec. trav. chim., 19, 51 (1900) 

11-2892 

27